Wisdom for a Fluid Career: Coach Melissa Wong

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“The question is, how do you… retain a sense of core self? What are the immutable qualities about yourself… that are going to stabilize you throughout all of the motion and the change?””

— Melissa Wong

This week on the Sunlight Tax Podcast, I’m joined by Melissa Wong, career coach and author of The Fluid Career, to explore how creatives, freelancers, and knowledge workers can navigate today’s changing world of work. We talk about building a fluid career, transitioning to self-employment, managing multiple income streams, and creating a career that can adapt as your life and priorities change.

If you’re considering self-employment, balancing multiple types of work, or looking for a more intentional approach to your career, Melissa shares practical insights for building a flexible career path without feeling like you have to choose just one thing.

Also mentioned in today’s episode:

00:02 Introduction to Melissa Wong and her work

02:04 Challenges of transitioning from employment to self-employment

04:11 Strategies for starting a self-employed career without data

08:00 The importance of articulating your unique offer

15:08 Practical steps for operational setup and legal considerations

23:00 Evolving passive income streams in the AI era

28:01 Building relationships and trust in a self-employed ecosystem

32:57 Managing multiple income streams and risk tolerance

39:53 Emotional and mental aspects of financial management

43:50 The core message of Melissa's book and its impact

44:59 Closing thoughts and how to connect with Melissa

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About Melissa Wong

Melissa Wong is a writer, thinker, and coach for creatives. At Coherence Studio she offers 1:1 coaching, group programs, and podcast conversations designed to help multi-talented creatives identify their unique worth and get into a place of intentional action.

For the first decade of her career, she worried about how her many roles and interests would ever coalesce into an intelligible, unified place. Now she helps creatives and knowledge workers articulate and share a coherent story of their work and design their career into an integrated multi-income system.

The Fluid Career synthesizes insights, stories, and tactics drawn from thousands of client sessions, offering a practical framework for designing modern careers to meet this moment of heightened complexity. 

Melissa lives with her family in Portland, Oregon where you can likely find her attending or hosting some kind of event or elbow deep in her latest creative project. 

Check Out Melissa Wong’s work: 

The Fluid Career Book

Get a FREE download of The Fluid Career book introduction here⁠

Website: Coherence Studio

Instagram: @coherencestudio 

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Order my book: Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed

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Transcript:

Hannah Cole (00:00)

everybody feels that way. The people who you look at their Instagram, you know, we look at people's part that they've curated for us. And in a way, what the money side is, it's the guts of the business. It's the actual thing. And it can often be so messy and so much more untidy, unstreamlined, unexamined than the front door.

And

People feel deeply self-conscious about that.

And

they're very

worried that everybody else knows something that they don't know.

And

Melissa (00:25)

Mm-hmm.

Hannah Cole (00:25)

everybody feels that way.

Melissa Wong is a writer, thinker, and coach for creatives. At Coherence Studio, she offers one-on-one coaching, group programs, and podcast conversations designed to help multi-talented creatives identify their unique worth and get into a place of intentional action. For the first decade of her career, she worried about how many roles and interests would ever coalesce into an intelligible, unified place. Now she helps creatives and knowledge workers.

Articulate and share a coherent story of their work and design careers into an integrated multi-income system. Her new book, The Fluid Career, synthesizes insights, stories, and tactics drawn from thousands of client sessions, offering a practical framework for designing modern careers to meet this moment of heightened complexity. Melissa lives with her family in Portland, Oregon. Welcome, Melissa, to the Sunlight Tax Podcast.

Melissa (02:05)

Thank you. Thanks for having me.

Hannah Cole (02:07)

I'm so happy you're here. And I was so pleased when you reached out because you really are talking to a very similar audience to, the Sunlight Tax podcast audience. so I'm just curious how you got here. How did you get into this work?

Melissa (02:22)

Yeah, I mean, I'll quickly say I was also very excited to get your response back because you've been on my radar for years. I feel like, truly, like when every any client comes to me and is like, I need some help with anything tax related, like you've been my go-to person to direct them to. I honestly couldn't remember when I first encountered, but I think it was maybe like a webinar or workshop. But my sense is just like a lot of my clients know about you. and so this opportunity to kind of

Talk live was you know, extra exciting. I think it's a classic, you tend to support the kind of person that you've been and you are or have been in a certain life. And I think

Hannah Cole (02:59)

Yeah.

Melissa (03:00)

I'll try summarize quickly, but I felt like I was drawn in many different directions for a long time and I felt a lot of, you know, existential angst of like, what am I meant?

to be doing with my work. And I've also just an ideas person. And while I didn't kind of like formally identify as like a creative or artist, I quickly realized when I started my coaching business that I tended to really enjoy conversations with people who were centering creativity. not just in for their income, but just in the way that they spend their time and and how they want to identify. So

I worked for companies like SoundCloud and Kickstarter in my past and kind of realized my own kind of theme and thread of helping project creators bring something to life. And I think what drew me to coaching was I've always liked supporting other people and proud prided myself in being a good listener. But with coaching, you get to be a thought partner too and kind of actually help them move forward and actually not just kind of,

like hear and digest and process emotions, but really think about okay, so what are gonna do with this now?

Hannah Cole (04:05)

Yeah, yeah. I love that. I love that. And I you know, I have touched into coaching a little bit myself. I find it very hard. So it's always like wonderful to learn from a great coach.

Melissa (04:16)

Hmm. Thanks.

Hannah Cole (04:19)

Well, I'd love to hear just like one of the things I'm particularly interested in about the people that you serve is like

When you talk about people moving from like full-time work, full-time employment into working for themselves, you know, I read the money chapter of your book, which was wonderful. And you know, it's notable, and I struggle too in my book, Taxes for Humans. I really struggled with like, okay, this is a much easier project when you have some data points, you have some months of work or years of work behind you that you can look back and see patterns.

But when you make that transition from employment to self-employment, you don't have that data. And it's really tricky to kind of move forward with any sense of confidence and vision there. So can you kind of talk to me a little bit about that particular challenge, kind of what you see and how those clients in particular feel moving into the world that you teach them about?

Melissa (05:16)

yeah, well, I feel like we could take the whole episode to talk about this. I mean, I think starting with the empathy and the emotional experience of like for some people, jumping off into self employment something they've wanted to do for a long time. It kind of is wrapped up in a lot of dreams and it's something they're actively seeking, even if it's scary. And I think for a lot of other people, you know, on the other side of the spectrum, it's like, I didn't

feel like this was my choice. Like I lost my job or I got, you know, whatever, laid off or something like that. And now this is sort of the plan B. So just kind of recognizing that there everyone's bringing in a different set of attitudes to self employment. But I think the same general tactics I would recommend for anybody, what no matter what you know part of that spectrum you fall on. and I guess maybe

As a clarifying question, do you want me to kind of talk about this in terms of like the financial side of things or just kind of general, like how do you get started?

Hannah Cole (06:15)

Well,

let's start with a general question there. yeah, how do you get started? And

Melissa (06:19)

Yeah. Okay.

Hannah Cole (06:20)

of course, because I talk about money, then I wanna land towards the money side.

Melissa (06:25)

Yes. So if anyone's heard of the idea of design thinking or the design process, I really lean on that a lot in my coaching sessions and thinking about how do we test things out, how do you prototype something and iterate on it when you don't have data? That's all you can do. You can do research from other people to see how it's gone for them. And I think that's smart. Both

Hannah Cole (06:49)

You

Melissa (06:51)

you know, whatever you can kind of learn online and also just very much talking to people doing informational interviews, which can be tricky for lack of a better word, sometimes right, where you're like, you know, for example, if we we're using you and saying, you know, say you had this full time job, now you're like, I'm gonna do my my own s business to support self employed people with taxes, right? What you do now, you might wanna understand like how have other

People who've done this price their work or how do they orchestrate and structure their offerings, right? And you can like do that online research without talking to them to a certain point. But then there's like the rich, juicy, kind of qualitative data that comes from talking to someone. And that's where it's sort of like, am I their competition? How do I reach out, you know, to people who are doing kind of the exact same thing as me? And I think that's where you can kind of like talk to other people who might be adjacent and working in partnership with those people to say, how did how did they work?

or if your business happens to be pretty like localized, I think that's another way to kind of reach out to people and not have it feel like a direct competition of like, okay, I'm building my practice in Asheville instead of like

Hannah Cole (07:58)

Yeah.

Melissa (07:58)

a New York clientele or something like that. and once you get people talking, I think they tend to be pretty open to share. Okay, this is what's worked for me, this is what what hasn't. and I see it as sort of this dance of research and trying to kind of like

not reinvent the wheel, but kind of model yourself on what you see out there. And then also

Hannah Cole (08:17)

Mm-hmm.

Melissa (08:18)

having moments where you're sitting w, you know, with yourself with a pen and paper and trying to clarify what am I really offering? Like what is at the heart of what I want? And I reference this kind of iki guy concept that I think many people are familiar with. But if you're not, it's like a Japanese concept of like, what is it

the intersection of what you're good at, what you enjoy, what people come to you for, what the world needs. And and kind of at the intersection in theory is sort of like what you should be offering. I think once you kind of like figure it out, like that's step one is like what can I actually offer and present to people that they think that they might pay for, then

Hannah Cole (08:58)

Yeah.

Melissa (08:59)

we need to kind of like test it out and see, people biting? Can I get practice clients? Do I like doing it?

I was just on a call with a client before we hopped on. and we were talking about how do you get testimonials and kind of show case studies of what you've done because when you're newly self-employed or trying to get new work, people tend to want to know like what you've done in the past. So I think another go-to component of this is like packaging and messaging what you've done in the past to

Hannah Cole (09:27)

Mm-hmm.

Melissa (09:28)

show.

truth trust and proof points to other people.

Hannah Cole (09:32)

Yeah.

Yeah, all of that so important. it's funny because even as you're saying this, I you know, I have worked for myself for a long time and everybody I serve works for themselves at least partially. But this summer my husband quit his job and went from full time W two stability into what I do, total self-employment. And it's so it's really actually funny to like

kind of with fresh eyes be going through it all absolutely again. of course now healthcare is involved since both of us are self employed. so yeah. it's on my mind. It's on my mind.

Melissa (14:59)

Yeah. Definitely.

That's so interesting. Like and and what a a much more intimate look you get when you're with this person, you know, day in and day out and

Hannah Cole (15:09)

Mm.

Melissa (15:10)

you know, have all the relational complexity between you and your your romantic partner. what are you remembering about this process just by witnessing him go through it again?

Hannah Cole (15:21)

Well, that initially there's all these questions of like just operational setup that are like, do I need a license to be doing this? do I have to register somewhere? Like, do I do I owe sales tax on what I'm doing? Like like that kind of question. Do I need an LLC? should I get a bank account? Like those little practical questions can feel agonizing if you don't know where to go. I say this because

These are the questions that I answer, and I hope to be that resource for people. but it is interesting to see how everybody has to cross those in some way or another. and and personally in my own work, I have found that people's anxiety about these things is at very different levels. People do not have one setting, and some people will operate on the fly.

And have the IRS chasing them down for unfiled taxes and like have a level of like, I'm okay with the mess here that another person is like, I am not going to take one payment until everything is nailed down, right? and the range is huge in between there. so it's just it's fascinating where people, you know, like if people could see each other, it would be fascinating to them.

yeah.

Melissa (16:40)

Right, right. Yeah.

I mean, and if I reflect on what how what I shared, it's almost this first phase of articulating and clarifying what you do. But you you're right, you inevitably hit the moment of trying to operationalize and think, what do I need to have structurally in place to legally be sound to receive income? you know, and and totally such a range of how people respond to this. But

What it makes me think of is another, know, recommendation I generally have as a person is like to feel connected to other people who are doing this so

Hannah Cole (17:14)

Mm-hmm.

Melissa (17:14)

that you don't feel so siloed. Or if any part of you is like trying to get a temperature check to say, like, do I really need this? Should I be agonizing over this? Right. Cause even

Hannah Cole (17:23)

Mm-hmm.

Melissa (17:24)

along that spectrum, there's a lot of doubt and questions along the way. So that's again why it's

So great that you offer what you offer is this kind of confirmation and reassurance of okay, worry about this, don't worry about this. But a lot of people I think feel intimidated to reach out to a professional to work with for a myriad of different reasons.

Hannah Cole (17:44)

It's so true. Do you find that people feel that way about reaching out to you?

Melissa (17:49)

I think know, coaching was on my radar like a decade before I started it and I think I arrived at it at the moment where I felt like

Culturally, the people were more open to coaching. And it just felt as commonplace, almost as commonplace as thinking about seeing a therapist or something like that. So I think there's been great strides in people's comfort level with reaching out to think about support, but it's intimidating. It's still an ambiguous process to people, I think, who don't fully understand like what is coaching. And so usually at the top of a new engagement, and we just chat for a little bit about.

this is kind of my version of it or this is how to set your expectations about it.

Hannah Cole (18:28)

Mm-hmm.

Melissa (18:28)

but I think for probably for both of us in our businesses, there's different access points that we've created and those come with also different financial levels of investment. And that's another place of course where a little bit of fear can show up.

Hannah Cole (18:41)

absolutely. And you know, and especially early days, like if we're talking about this person, this theoretical person who, you know, goes all in from total employment to total self employment, that's a very hard transition.

Melissa (18:54)

Mm-hmm.

Hannah Cole (18:54)

the unknown there can be so intimidating that you feel fearful, you can feel really fearful about spending anything. And this like mindset of making investments in your business, even seeing yourself as a business. I find that can be a challenge.

Melissa (19:09)

Yeah. And one thing I really loved about, I mean many things about just checking out your site again last night ahead of our our conversation today was you have these customized visuals and and guides for different kinds of creatives that might help direct them towards certain different structure based on what kind of services they provide, right? Like a doula versus a designer versus a I don't know, a photographer or something like that.

Hannah Cole (19:37)

Mm-hmm.

Melissa (19:38)

And it's it's nice to think about how do you create a first touch point with people to build trust with you that is customized. It isn't like a blanket statement. how have people responded to those do you call them? Guides or visuals, charts?

Hannah Cole (19:50)

yeah, my visual

guide to to your tax deduction.

Melissa (19:54)

Mm-hmm.

Hannah Cole (19:55)

they've been popular. I feel like it's a nice I mean I I made it from a practical need. mean, I feel like I sort of got into this work because I was interested in linguistics, as weird as that sounds. I'm interested in like cross-cultural communication and

I'm really transl like I'm a translator between the culture of creativity and like you know vision to the culture of accounting. Which is so they are so different from each other. And so I find it really fascinating and the personality types are so different from each other that I actually find that this like quality that I have as a human of being able to kind of like move between worlds is like that is sort of

the actual work that I do. So making

Melissa (20:41)

Yes.

Hannah Cole (20:42)

that, I feel like that's a translator. Those guides are like a translator.

Melissa (20:46)

Mm-hmm.

Hannah Cole (20:46)

meant to call in a visual person. Yeah.

Melissa (20:50)

That makes a lot of sense to me. I think, and that's probably why you've been in business as long as you have and and found the success you have is like artists and self-employed people, creatives who are speaking a certain language. I mean, out of all the languages out there, I think like taxes and the IRS language is like probably up there in terms of like intimidating to to break down. so it's yeah, it's a real service to kind of create that accessibility point.

You also offer a intensive, like a live offering. Is that

Hannah Cole (21:21)

Yeah.

Melissa (21:21)

pr pretty new or

Hannah Cole (21:23)

It's brand new. Yeah. I'm absolutely going through what I assume a lot of your clients do in just like testing, making sure I stay focused on like the minimum viable, thing that people will walk away with and not get too fancy too early. price discovery, like all these, you know, it's it's scary. but I'm

What

I find is just having some experience doing this, some track record, it's much less scary when you've done it before.

Melissa (21:54)

Yes.

Yeah. It's this the cool thing about self-employment, right, is like everything's kind of a creative sandbox and playground and you can kind of be spinning up new things and and it behooves you. It's a to your advantage as things shift, right? Like, I know something w maybe we were gonna talk about was like

Courses was one example of like a a go-to passive income structure for a lot of, you know, self-employed people who were trying to build a brand around kind of teaching people how to do something, with AI, or kind of just after that like peak moment of the pandemic and people putting out and subscribing to courses. I do think that there has been a trend of like people wanting humans, right, to

guide them through something. and that's an example of like, I'm not sure if you've like consciously thought, okay, I need to like in addition to my recorded course, do a live thing. But I think you're right on the pulse of and especially with money, right? Someone who's like, okay, I see you. I'm literally an expert talking to you live and I'm giving you this sort of custom feedback. that's kind of the ultimate reassurance they could get versus a a course that's just not going to talk back to them.

Hannah Cole (23:01)

I so agree. Well, you had a, you know, you spoke about this in your book you have a a wonderful section on creating multiple sources of income, which is a thing I'd like to bookmark anyway. But particularly that mention of passive income sources and those, you know, like a a download, a worksheet, a package, a an online course. I am curious if you're seeing that evolve because I mean I'll just say

In all honesty, in my business I've certainly seen like on online courses sales just nosedive with I think AI and people's wanting to not be on a screen as much as they can. So I'm curious what you see.

Melissa (23:42)

Yeah. You know, I don't I have anecdotal response to this, right? I'm not just so to caveat

Hannah Cole (23:48)

Mm-hmm.

Melissa (23:48)

it, like I'm not looking at big reports of of this too, but I think that checks out and just even kind of content that I listen to as well, other people who are just like you, kind of transparently sharing about how they're shifting their business. I and I think it's really important that you listed not just like a the onset of AI.

But really like people just wanting to not be on their screen as much and wanting to experience, you know, local or IRL things. I I feel that in myself.

So

Hannah Cole (24:15)

Mm.

Melissa (24:17)

it is, I can imagine, for people who have been in this business for years and seen something work and suddenly to sense, this isn't working in the same way is I don't know, destabilizing for for a moment at least to say, like, okay, what's going on?

But I think, know, what I say in my book is that passive income streams I think are always really alluring. It's like, cool, what I can put a thing out there and just keep getting, you know, sales from it. and I just try to remind people that like it does take work to manage this, to keep marketing it, to sharing it out. You gotta like direct people's attention to it. and

Hannah Cole (24:51)

Yeah.

Melissa (24:52)

maybe a question in return for you is like, we're kind of talking about

I don't know what the right language is, but sort of like

People in our field who are kind of like I guess like B2C, like having individual customers and clients come on. There's like a certain kind of like not template or cookie cutter formula, but sort of like, okay, here's the pathways we have. It's like we've got your one-on-one clients, you've got a course, maybe, you've got a community. and then there's all these other passive income streams.

you know, maybe outside of that, like licensing. I mean, ri I don't I don't know if real estate, if you would lump that in there. When you work with your clients, I guess, or people that kind of subscribe to your programs, do they tend to like mirror us, like you and my kind of style of business, or do you actually see some creative sources of passive income stream that other people might not be thinking about?

Hannah Cole (25:42)

That's a that's an interesting question. I have to think about it a little bit. I would say a lot falls into those categories that you mentioned. You know, coaching, one-on-one work, one-to-many classes, maybe like workshops. and then with that one-to-many stuff, you know, if you can record it and then sell it. And again, I think those are really nice to have, and when they're high quality, they continue to

make sales, but I do think in this environment when people are like sitting with Chat GPT open, they just ask it their questions and if they get a passable answer, it's hard for your paid offering to compete with that. so it you've really got to be offering something either custom to that person or valuable or, you know, protected by a license. I say this as a licensed tax professional that even though my work

is protected by a license, Chat APT and Claude are perfectly happy to answer your task questions. They're making things up, but the client

Melissa (26:38)

Right.

Hannah Cole (26:38)

actually it doesn't appear that way to the client. The client doesn't actually know how bad that information can be because it is offered so confidently. So that's a weird one.

Melissa (26:49)

Right. Which probably imagine

where my mind goes is like there's an interest interesting choice point on your end of like how loudly do I try to like educate people that like they shouldn't blindly follow what a Chat GPT says, right? Like I could almost envision a series of like, okay, I asked Chat GPT this question and this was the answer, and actually like this is the answer I would give, right, as the expert, or this is why this is an incomplete or maybe like an off base answer. but because we don't

really have like a unified, I know, like qualitative board helping filter out what is good advice or or not. It truly is kind of left down to the individual level to figure out how much trust they're putting in these LLMs.

Hannah Cole (27:30)

Yeah. I mean it is kind of interesting because my license, there is a due diligence requirement to my license. Anyone with a tax license, whether it's like me an enrolled agent or a CPA, you have this due diligence standard. You cannot just say something you think is true. You have to have done the due diligence to know that it is true. and typically you'll sign all kinds of things with an accountant saying like a verbal thing doesn't count as that.

Because my brain can I can have a brain fart. Like it can I can accidentally misspeak sometimes. So like if an accountant gives you something written down and you've signed an engagement letter, that's like locked in, licensed, reliable tax information. And basically short of those, you know, licensing requirements, you're not getting that. And so it is kind of weird that you can just ask these questions of this machine.

And it tells you stuff so confidently that no accountant is ever gonna behave like that. I imagine doctors might be pulling out their hair over similar reasons. Like, okay, we can

Melissa (28:36)

Yes.

Hannah Cole (28:36)

draw from Web und D and like, you know, there may be some stuff that's good out there, but maybe we're drawing from conspiracy websites and talking about drinking bleach.

Melissa (28:46)

Right.

Well, I think everyone, know if you're hearing this in your circles, right? It's just talking about trust and maybe that's where I'd I'd pull back in relationships where it's like, even if you're new, starting out with self employment, I brought up informational interviews. That's one kind of relationship. Then I also brought up like peers, right? Like other

Hannah Cole (29:06)

Mm-hmm.

Melissa (29:07)

people who are kind of doing the self employed thing for you. And maybe one other

layer to that or manifestation of a peer is someone who can be kind of like an advocate, like a a partner. whether that's

Hannah Cole (29:18)

Yeah.

Melissa (29:18)

to actually do referrals, how can you plug into other groups or partnerships that have a built-in trust already established? So whether

Hannah Cole (29:29)

Mm.

Melissa (29:30)

that's like you look up that there's like an don't know.

a summit going on and you like pitch a certain workshop for something that has like a little bit of a bigger draw or a kind of energy. or just kind of reaching out to someone who's doing something comparable, right? Like you and I are a really great example actually, because we're not offering the same thing, but our our target client is more or less the same. And so it you know, we can I refer people out all the time when I myself am not the best person.

for the task.

Hannah Cole (30:00)

Yeah. Yeah. I really love that. And also and I just have to say that that idea of the informational interview was not fully on my radar in this mode. It's hilarious because I tell my daughters to do this about career stuff all the time, but I've never thought about it like as an adult mid-career. it's so smart. but I'm curious, I wanna kind of circle back to this like theme that kept coming up in your book and in your work.

at

large, which is like the multi-income stream, multi-hat wearing component.

Melissa (30:30)

Mm-hmm.

Hannah Cole (30:30)

I'm curious about that because I sometimes with the brain that I happen to have, focus can be a challenge. And so like I do a lot to cultivate my focus and to not split it. and so sometimes I see multi on something and I'm like, ugh I can't. I can't do two things at once.

So I'm just curious,

Melissa (30:49)

Yes.

Hannah Cole (30:50)

like if you've had experiences like some people do well with that, some people do not. These are who you do think should do that kind of thing or not. Like tell me a little bit

Melissa (30:59)

Mm-hmm.

Hannah Cole (30:59)

more about like multiple income streams, like you

Melissa (31:02)

Sure.

Hannah Cole (31:03)

engage that.

Melissa (31:04)

Well, first I'd wanna maybe add to the complexity here to say like you have a focused business and it has a very, I think, clear mission statement essentially and and like a clear focus on who you're supporting. But even within your business, you have multiple income streams, right? Like

Hannah Cole (31:21)

That is true.

It's absolutely true.

Melissa (31:24)

So you're have a focused multiness and then there's someone else who could be take more or less what you have and then another universe on top of it. And then their complexity gets even more you know, advanced or or or complex. So think it would go back to this sort of like risk tolerance and trying to understand not only how your brain works in terms of how you're managing.

your to-do lists and your tasks and how distributed and broad you want to be versus focused.

Hannah Cole (31:51)

Mm-hmm.

Melissa (31:52)

when it comes to money too, it's like part of the premise of the fluid career is a little bit of heartening back to the the portfolio career idea, which is portfolio like a financial portfolio. It it benefits you to diversify your assets so that you're

protecting, you know, hedging against risk. If one of in the in in the career context, right, if one of your jobs goes away, income streams, you're not left in the lurch and you don't have this bigger moment of upheaval because you've got these other things going. You know,

Hannah Cole (32:21)

Yeah.

Melissa (32:22)

the the sacrifice of that is the energy it takes to, you know, kind of be up holding that multiness in a regular basis. So I guess I'd say like

from a risk standpoint, if someone likes to be focused with their brain, but maybe they have one or two clients and then that big client goes away for s for whatever reason, I think they just have to know that they're gonna have know, a bigger p percentage of their income that they need to replace. And

Hannah Cole (32:48)

Uh-huh.

Melissa (32:49)

that might be more stressful for them overall. So that could mean like hopefully they're making enough from these

a couple different concentrated income sources to be saving enough and you create enough of a buffer so that you can, you know, float yourself to the next bigger client. But for

Hannah Cole (33:05)

Yeah.

Melissa (33:06)

someone like me, for example, like if I have 20 to 30 clients at any given time, if one client just stops, just, you know, wraps up with me, it doesn't jeopardize my whole system. Like, you know, if I start getting maybe like five or six clients canceling or

stopping kind of unexpectedly all at once, then I'm like, okay, gotta, you know, do a push on the marketing front. so I think it kind of comes down to how your brain works combined with a bit of risk tolerance. And then of course interacting with what you are so ex hopefully excited to offer and the b structure that that kind of naturally links to, right? Someone who's

And I'd say maybe there's flexibility there. I was gonna use an example of like someone who's like an illustrator, for example. They might

Hannah Cole (33:45)

Mm-hmm.

Melissa (33:46)

think, okay, I need to get know, a lot of different or I'd I'd love to get a retainer. Like I'd love to get like one client that's always needing like, you know, illustrations from me month monthly or something like that. But if they recognize, that's that's too much risk and concentration in one place, then they might think

Okay, how do I add this other passive income stream? How do I maybe again license my my illustrations to a textile designer to use or, you know, getting creative from there?

Hannah Cole (34:12)

For sure.

Melissa (34:13)

but it is, I think that's kind of where the crux of my book is like.

helping create proposals of systems and structures that help contain the fluidity actually. So from a

Hannah Cole (34:23)

Yeah.

Melissa (34:23)

multi income standpoint, it's like, can it be as simple as maybe when you're starting out, it's a weekly end of week financial check-in just to kind of look at your streams, how are they doing, and log them in a spreadsheet? Then it can move suddenly to like every month, right? We don't want you to have to look at it every single

week.

Hannah Cole (34:42)

Mm-hmm.

Melissa (34:43)

But just that kind of initial practice of spending the time paying attention and charting, know, almost like collecting the data points to then later assess, I think is a huge part of it.

Hannah Cole (34:54)

Agreed. Yeah. I have a couple things to add to that. One is this this woman who I've done some collaborating with who has a great substack. Her name is Anna Burgess Yang. she works more on with a tech audience, but it's all about like solopreneurship. And she has this really interesting thesis from her personal experience, which is that having a job is the ultimate lack of

multiple income streams and and way riskier in her estimation and much riskier than having your own like 30 clients where one client goes away, you're fine, five go away. Okay, you have some work to do, but you're still okay, because she was laid off. And know, that's all of it gone overnight. So

there is something

Melissa (35:40)

Right. And

Hannah Cole (35:41)

to be said for that, like multiple you know, self-reliance.

Melissa (35:44)

And I I try to kind of call out this at the beginning of my book, which is this book is gonna resonate a lot with people who are already building fluid careers. But I think even people who are in a nine-to-five job and not very diversified could benefit from listening to

Hannah Cole (36:00)

Uh-huh.

Melissa (36:01)

it. And it the hard message to hear might be, okay, you're comfortable now, but how can you

Doing some of the practices that help you be primed, even for diversification. So for example, from a relationship building standpoint, like maybe it's tempting to just be working with the people on your team. But what if you took 10% of your sort of like social interpersonal networking energy at work and tried to make connections with people on different teams, people

Hannah Cole (36:33)

Mm-hmm.

Melissa (36:33)

at different companies who are on simpler teams?

Not because you're looking for a new job necessarily, but you are a in a moment of stability. You are fortifying your relationship ecosystem so that if you are laid off, you're not in a situation that a lot of clients come to me with, which is I have to like rewarm my relationship network and it feels a little forced or I don't want to come across as authentic of like I'm only reaching out because I need something, but that's kind of the situation.

Hannah Cole (37:02)

Yeah, it's hard. It's really hard.

Melissa (37:04)

Mm-hmm.

Hannah Cole (37:05)

Huh.

Melissa (37:05)

But it all takes time. So that's kind of this this trade off of like I understand if you have a full time job, many people have so much on their plate already. So to think about like, don't need another job right now, but I'm suddenly gonna be doing all these different actions that actually tee me up to do a job, like that's that's an energetic ask, right? So I

Hannah Cole (37:23)

Sure.

Melissa (37:23)

I'm aware of that and it's and it's it might not be possible for everybody.

Hannah Cole (37:27)

Yeah, heard. Actually, even just on that notion of like the multiple income streams and the sort of like focus of that, it's funny I see you doing a good job coaching like right here with me. Because pointing out that I do this thing that I'm saying I I can't imagine doing, it makes me realize that actually like my my philosophy is like, well, y you can have it all, you just can't have it all at once. And so it's

kinda like you do one focus area and then another and then another. And so you may have this accumulation of things behind you that exist and may still be working for you, even if your focus is over here.

Melissa (38:05)

Yeah, it makes me wonder, I don't know if this has come up in any kind of your intensive or or even just kind of one on one conversations with clients, but it's interesting to kind of understand the perspective that we carry with us and sort of the bias of that. Like when you almost say, like for me, it's it's really nice to feel like I'm at least focused.

Hannah Cole (38:24)

Mm-hmm.

Melissa (38:25)

So if you were to have a client come to you and saying, Hannah,

I have all these ideas and I'm so excited and I'm really diversified, but I'm also incredibly overwhelmed. And I I feel when it comes to taxes, like, is this a good idea for me? Like, should you think even though I'm in my heart of hearts, I want to be diversified, what I'm noticing is like it's being it is a kind of adding stress in terms of financial management and and a concern about how that's gonna show up at tax time. how might you

Counsel that person.

Hannah Cole (38:52)

Yeah. in a way liked what you said before that you gather data points even if you n don't necessarily analyze them till later. But you know, all those transactions kind of like building a system to capture the data, to me, that is priority number one. When you do that, you don't have to sort it out today, but you know that it's there for the day that you are gonna sit down to sort it out.

Melissa (39:17)

Mm-hmm.

Hannah Cole (39:18)

The problem comes when you don't have any tracking at all. Cause then now you really do have a beastly project on your hands. You have to go on a hunt for stuff, so I think in a really concrete way, it's just like hooking up that bank account, having a separate business bank account, making sure that every transaction is going through that and you're not using stray personal cards for business items that you'll later have to track down.

Yeah, it's it's more like a habit muscle and like a structure that you operate within. And once you do that, you really can have a lot of freedom inside that. which I think is not how people tend to think of like money management. They tend to think of it as only a chore and totally horrible. but I think of

Melissa (40:01)

Mm-hmm.

Hannah Cole (40:02)

like once you have that structure in place, it gives you a lot of mental freedom.

Melissa (40:06)

Mm-hmm.

Hannah Cole (40:06)

Yeah.

Melissa (40:07)

I I admittedly ran a group program called Savvy, which was a I ran it two times. Once was just kind of general, I'd say like personal finance with all the caveats of like I'm not a certified certified financial planner and all of that. But and then the second time I ran it, it was more specifically for people with variable income. And I think

Hannah Cole (40:27)

Mm.

Melissa (40:27)

probably the biggest takeaway I had from that experience was just how emotional.

money is. Right. I I think I just kind of naively didn't expect that part of like being in this, you know, somewhat intimate like six to twelve people container

Hannah Cole (40:42)

Mm-hmm.

Melissa (40:43)

and feeling

energy shift in the room and different people's opinions and and kind of know maybe certain people like not vibing with each other in a group because think it was just such a charged it is such a charged topic. and

So I guess I'm curious with you. So much of it is, as you said, and we both have echoed like the structures that you keep. What have you found with your self-employed or even multi-hyphenate clients that can kind of on the mental and emotional side kind of be these reminders, maybe pep talks along the way of like, okay, what if I haven't been tracking or what if I didn't start off doing it the the quote unquote right way to the begin Like

Hannah Cole (41:22)

Yeah.

Melissa (41:23)

What

do you notice yourself maybe like assuring them or trying to remind them before they get into the actual tactics?

Hannah Cole (41:29)

I think one of the most important things that I try to say as often as I can is every single client that I have, almost every single conversation, initial conversation I've ever had with a client starts with, I don't know anything about this, I'm totally behind. Which is like saying every kid in the town is above average. It's just not possible.

You can't all be behind. so everybody feels that way. Like that's a thing. The people who you look at their Instagram, you know, we look at people's outer, you know, the the part that they've curated for us. And in a way, what the money side is, it's the guts of the business. It's the actual thing. And it it can often be so messy and so much more untidy, unstreamlined, unexamined than the front door. And

People feel deeply self-conscious about that. And they're very worried that everybody else knows something that they don't know. And everybody feels that way.

Melissa (42:28)

Mm-hmm. Mm-hmm. Yeah,

that's such a nice reminder of like I'm normal or I'm not the only one.

Hannah Cole (42:37)

Yeah, so so normal. And there's no tax education in this country. So we we all end up feeling that way. Yeah.

Melissa (42:44)

Mm-hmm. Mm-hmm.

Hannah Cole (42:45)

so Melissa, I wanna ask you kind of a bigger question about your book. before we end our conversation. it's a really beautiful guide. I love how you kind of you do walk into the emotional

side and I love and agree with you that you know like knowing what your like fair, good, better scenarios financially help you understand, like, I have some time to figure this out. It like actually gives you some space to do the work. I wanted to just ask you on a larger level, like who you're really hoping to connect with with the book and like what you want like

If

you had a vision, a dream for what somebody takes away after they read your book, what that what that is to you.

Melissa (43:29)

well, I appreciate the kind words and it very much is a book, but it could also be called a handbook. Like I really it it there's a density to the book that and I'm be curious how you relate to this with your book as well. Yeah.

Hannah Cole (43:41)

Well, I wanna jump in. When you say that

I feel that people may be scared, but I wanna say it's very readable and these are exercises

Melissa (43:48)

Mm.

Hannah Cole (43:49)

that actually and I find this very humane. They say like, Well, this will take you twenty minutes, this one will take you an hour, this is five minutes. You know, it's like it's you say that it's dense and it is 'cause there's like exercises, but they

Melissa (44:01)

Mm-hmm.

Hannah Cole (44:02)

feel gentle to me.

Melissa (44:03)

Thank you. I appreciate that. Yeah. My goal in writing this book was like, I didn't want a book someone to end like finish reading the book and say this could have just been a short blog post and you just kind of like put flesh on it with like ten different case studies. Like I didn't want to follow that very go-to format, which I understand is a go-to format for a reason. I do have case studies that I thread through to try to like illuminate the concepts and practice, but I did, you know, the coach in me really wants it to be actionable. So I want people to

You know, you could read it first pass and not do the exercises, but the change it's gonna happen is actually doing the exercises and mapping it onto your own experience. So my high hopes are that it doesn't have to be every single chapter of the book. It's divided into five kind of main domains: identity, skills, relationships, time, and money.

You can just choose even one of them. And if you move one of those things forward and feel a little bit more structured or interconnected because of that, then I would say, Great, amazing. but I think the final chapters where my mind goes in answering your question, it's called center. And it's and it is more of the emotional and kind of existential side of this, which is anyone who wants to be in motion.

Have more variety, have more multiplicity, I want them to feel validated that that's totally wonderful. And it comes with challenges for sure. the question is, how do you kind of retain a sense of core self? What are sort

Hannah Cole (45:34)

Mm.

Melissa (45:34)

of the immutable qualities about yourself, whether that's values, whether that's certain relationships you kind of commit to uphold, whether that's certain rituals and practices that are going to

stabilize you throughout all of the motion and the change and can you

take a moment to say that those are just as important as figuring out how to prioritize your to-do list or figuring out your money income system because if you don't feel stabilized from the inside out, like it's all gonna feel shakier.

Hannah Cole (46:02)

Couldn't agree more. That's beautiful.

Melissa (46:04)

Mm.

Hannah Cole (46:06)

Yeah, I really appreciate that. I feel I feel your coaching. I feel I felt as I read the part of the book that you sent me, like I I felt that voice, that like guiding hand, and I felt the experience.

Melissa (46:15)

Mm-hmm.

Hannah Cole (46:16)

It's really, I think it's lovely. I hope it does really well. Is there

Melissa (46:19)

Thank you, Hannah. I really appreciate it.

Hannah Cole (46:21)

anything, is there anything you want to leave the listeners with and just tell people how they can find you?

Melissa (46:26)

Yeah, I think just on my website coherence.studio/fluid you'll find book. And if you want to poke around to different offerings I have, great as well. I do have a self-paced course. I do ha offer one on one coaching, and have like a couple one off trainings. But yeah, thanks so much if just for tuning in and thanks Hannah for giving me this space to share a little bit more about my book and and the exchange that we had today. It was

It was a pleasure.

Hannah Cole (46:52)

Awesome. Thanks for being here.

Stacy Ennis: The Power of Nonfiction: How a Book Can Advance Your Business Mission, Leadership & Values

Listen and Subscribe Here

“If you really focus on the reader and creating something meaningful and impactful and excellent... it has longevity and shelf life and continued work to do out in the world well beyond you.”

— Stacy Ennis

In this episode of the Sunlight Tax Podcast, I sit down with Stacy Ennis to explore what it really takes to write and publish a nonfiction book that grows your business, strengthens your brand, and creates lasting impact. We discuss the publishing process, book coaching, traditional publishing vs. self-publishing, and why integrity, strategy, and a clear message matter more than simply getting a book into the world.

Stacy shares practical insights from years of helping authors craft books that not only sell, but also make a meaningful difference—offering valuable guidance for anyone considering writing a business book or becoming a published author.

Also mentioned in today’s episode:

00:10 Introduction to Stacy Ennis and her background

01:00 Stacy's journey from childhood reading to publishing expert

02:36 Her experience in publishing and ghostwriting

03:24 Working with authors with a bigger mission

04:49 The ROI of writing a book and trust building

05:56 Trusting Stacy's expertise after a trust-breaking experience

07:43 The importance of mission and impact in writing

09:04 The strategic value of a book for influence and marketing

10:33 Shelf life and longevity of well-done work

12:24 Reflections on the author journey and publishing routes

14:36 Exploring traditional, self, and hybrid publishing

16:36 The evolving landscape of publishing and author education

18:24 Why hybrid and self-publishing are viable options

20:28 The role of a book in business, trust, and influence

24:18 The transformative process of organizing ideas

27:37 The impact of writing on personal and business growth

28:58 The importance of creative health and deep thought

31:16 Rebuilding self-trust through the writing process

32:44 The societal and professional importance of authorship

33:01 Stacy's resources and podcast

If you enjoyed this episode, please rate, review and share it! Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.

About Stacy Ennis:

Stacy Ennis is a best-selling author, book coach, and speaker on a mission to help leaders clarify their ideas and harness their unique story to make an impact. Her background includes impacting more than 100 books in her 17-plus years in publishing; ghostwriting for a Nobel Prize winner in medicine; and leading as executive editor of Sam’s Club’s Healthy Living Made Simple, a publication that reached around 11 million readers. Stacy’s work and writing have been featured in Yahoo!, Inc., Insider, Publisher’s Weekly, Katie Couric, and the TEDx stage. Stacy is also the host of the podcast Beyond Better and holds a master’s in writing and editing from the University of Cincinnati.

Check Out Stacy Ennis’ Work:

10 Things You Should Know Before Writing a Nonfiction Book free resource

Author Influence Circle

Direct link to book a call with Stacy to chat about their book

Instagram @stacyennis

LinkedIn: Stacy Ennis

Study mentioned on the episode

Episode Links:

Check out my program, Money Bootcamp

Get my Tax Help on Substack

Get your FREE visual guide to tax deductions

Order my book: Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed

Watch YouTube video version

Transcript:

Hannah Cole (00:07)

Stacy, welcome to the Sunlight Podcast. Stacy Ennis is a best-selling book author, book coach, speaker on a mission to help leaders clarify their ideas and harness their unique story to make an impact. Her background includes impacting more than a hundred books in her 17 plus years in publishing, ghostwriting for a Nobel Prize winner in medicine.

And leading as executive editor of Sam's Club's Healthy Living Made Simple, a publication that reached around 11 million readers. Stacy's work and writing have been featured in Yahoo! Inc., Insider, Publishers Weekly, Katie Courick, and the TED X stage. Stacy is the host of the podcast Beyond Better and holds a master's in writing and editing from the University of Cincinnati. Stacy, welcome to the Sunlight Tax Podcast.

Stacy Ennis (00:56)

Thanks, Hannah. I've been really looking forward to talking with you.

Hannah Cole (01:00)

Yay, me too. What a delight. Will you just give us a little bit of the journey? Like how we've we've heard your bio and where you are now. Can you tell us a little bit about that journey and how you got to where you are today?

Stacy Ennis (01:15)

well, like most people in publishing, I have a a love story with books and writing that started when I was seven. with reading The Chronicles of Narnia. That was my like fall in love with books series. of course The Babysitters Club, all kinds of different books that at the time I didn't really realize this, but growing up in Boise, Idaho, which people call Whiteho, it's 87% white, very affluent.

It was a very homogeneous space to grow up and my books gave me a sense of the world. It helped me develop a mindset beyond where I was, empathy through other people's stories. So it was kind of my first world exploration was through reading books. And you know, fast forward a long time, I went and got my bachelor's in in writing. And then shortly after that, my husband and I moved to the Dominican Republic. We weren't

married at the time, but we moved to the Dominican Republic and then Vietnam, came back and went to grad school for writing and editing. And along the way I was I started working in publishing. I as you mentioned I I ghostwriter for a Nobel Prize winner for four years. I also used to run Sam's Clubs magazine, Healthy Living Made Simple. We had about 11 million readers. I was executive editor of that publication, which of course was a a huge and important role and taught me so much about the publishing industry.

and so I've spent most of my career in well, I spent all of my career, I should say, in the written word in some capacity, and as an editor, as a ghostwriter, and today as a book coach. So I I work with authors or future authors who want to write a nonfiction book. That's a space that I operate in. And I would say, you know, particularly in work with authors that have a vision beyond the book. So

The book is not their end all be all goal. They have a reason they're putting this book out into the world, whether it's a business goal or a social mission or something that's bigger than the book. And I get to work with really amazing people. It's it's the coolest work.

Hannah Cole (03:24)

I love it. I agree with you. It is. and I've noticed because I am in your membership program, the author's influence circle, and the other people in there are really cool. Like everybody is trying to make the world a better place in their from

Stacy Ennis (03:37)

Yeah.

Hannah Cole (03:37)

their specific vantage point and that makes me thrive.

Stacy Ennis (03:42)

Yeah, and the and they're actually doing things to do that. You know, like they're out there, you know, doing their good work, whatever shape that takes in the world. And I think that is a a real hallmark of the kind of clients that I love to work with. They're action takers, they're big dreamers, but they're not just talking about what they'd like to do. They're actually taking action toward toward their dreams and their bigger vision.

Hannah Cole (04:07)

Mm, I love it.

So Stacy, I did mention this in our session together, the ROI of writing a book. But I do wanna just say for those people who are listening to the podcast and weren't in that session, by the way, if you wanna get

the recording for that ROI of writing a book. If you just join my Substack, it's free for subscribers. So you can either send me a note through Substack that you're a subscriber and you'd like that recording, or you can send an email to hello@sunlighttax.com So everybody who missed the ROI of writing a book session with Stacy, you're so welcome to have it. Okay, so what I wanted to say is just like I had this experience with you, Stacy, that I want to say to everybody because

It made it really made me trust in your expertise, like trust in your deep wisdom. You're n not only are you an incredible writer, I mean you cannot how many books have you written? Seventeen.

Stacy Ennis (05:01)

Yeah, eight

eighteen. Yeah. I'm working on the nineteenth right now. Yeah.

Hannah Cole (05:05)

Good Lord. yeah, you can't do that without being

of a not just a good writer, but somebody who's really mastered the process, right? but I had this experience because I had a book deal, I suddenly had a book deadline, super exciting, and I went out and I hired a book coach just on somebody's recommendation. She was kind of new and a little green, I think.

and I had an awful experience. I'm not gonna name her, but I had an awful experience, very trustbreaking, very yucky. and I called you Stacy because you know, you you had a lot of experience, and I just I had like an SOS call with you. And I just want to say for everybody listening, like Stacy's generosity was unbelievable. She was just like, just there to kind of hold my hand through one of frankly many.

book crises. and it was so evident to me that not just is she a fantastic writer, but that she really knows the publishing world and the book writing journey and process and also the strategy around like placing your book in the world. and I just can't tell you how held I felt by just that SOS call with her, which is why I then joined her membership. And like, so I just wanna, I just want to put that out there because I really think you're

Work is incredible, Stacy.

Stacy Ennis (06:24)

Thanks, Hannah. I don't even know what to say, but thank you. That was so kind.

Hannah Cole (06:30)

yeah, no, I think it I think it's important. I mean, I know y you have to build your own trust with people, but I really do feel like, wow I I like saw you when it was hard for me, through a crisis and and it mattered. It made a difference.

Stacy Ennis (06:44)

Maybe, you know, one thing I'll I'll layer into that experience. yeah, I'm sorry that you had experience with the the first coach and I think that like this is a problem in our industry that we have a lot of people out there that are not qualified really to be guiding people on these journeys or make kind of big

promises or just give bad advice. And that's not the standard. Like like most places, most people have really good intentions and care a lot. But it is it is tough when you have those experiences and

I think that that's why conversations like this and the episode that you did also on your journey, Hannah, which you you published a little bit earlier, these types of things that we're doing are so important for people that are considering this journey so they can avoid some of what you went through. But then I also just wanna lift up your resilience and like ultimately with your work.

you came back to your service through your work. And I think that's what really held you through that period because this is why I mentioned at the top, I work with authors whose end goal is not the book. The the the go the book is a a vehicle, a catalyst to do something in the world.

And I

Hannah Cole (08:00)

Mm.

Stacy Ennis (08:00)

think part of why you were able to, you know, dust yourself off and find your way forward is because you had a mission that was bigger than that road bump.

Like you were going to traverse that road bump because you cared deeply about the reader on the other side of that. And you cared so much about making it useful and excellent. And that's the that is really what

makes a great book at the end of it. Of course there's people that support you and guidance you can get, but I think that the mindset that you had is ultimately why your book ended up becoming great at the at the when all is said and done.

Hannah Cole (08:41)

I appreciate that so much. you know, I really I felt like going in. You tell me how good this strategy is, but my strategy going in was like, I'm not Michelle Obama. I do not have a massive platform. It's gonna be uphill the whole time to kind of get the word out about this book. PS is still available and it's still great. Everybody.

Stacy Ennis (09:04)

Yeah.

Hannah Cole (09:05)

but I just figured like

really my best friend in this process, the only way this book was really gonna do as well as I think it deserves to do is if it was so good that people would want to tell their friends. And so I

Stacy Ennis (09:20)

Yeah.

Hannah Cole (09:20)

really felt focused on this has to be the best book to teach a self employed person how to manage their taxes, like how to set up their business and like not get tripped up by the IRS. so that

Stacy Ennis (09:32)

Yeah.

Hannah Cole (09:33)

that really was my vision and

Yeah, it just was like I wanna be able to also like when you're marketing and doing the sales stuff, if like me, that's not your favorite part of the company you run.

Stacy Ennis (09:47)

Why ever not?

Hannah Cole (09:50)

I feel like I do a much better job marketing something that I know is actually the best, right? And so I just wanted to be able to feel that way about my book, which I'm ha happy to say that I do. But I don't know, you

Stacy Ennis (10:05)

That's huge.

You gotta be in love with the the work or else you're not yeah, you're not gonna wanna show up. And I think just to feel really proud of what you did is important, an important result of all of this. And your book, I mean, I know tax code changes, so there's probably gonna be updates and iterations that you'll provide, probably also on your website, which is a great way to keep people engaged with your platform. But even, you know

Even books that have some aspect of them with a shelf life can serve you for so long. I just, my co-author Ron Price and I just won an award, I think it was either earlier this year or the end of last year, for a book that we published in 2018. So I mean it gives you a sense of

Hannah Cole (10:51)

Wow.

Stacy Ennis (10:52)

the the longevity of well done work. If you really focus on the reader and creating something meaningful and impactful and excellent.

Like it has longevity and shelf life and, you know, continued work to do out in the world well well beyond you.

Hannah Cole (11:09)

Hm. Yeah, I appreciate that. Also, congrats on your award. How exciting.

Stacy Ennis (11:13)

Thanks. It was so cool. I was like,

wow. You know, it was very unexpected.

Hannah Cole (11:18)

That's awesome. Yeah, I did a lot of strategizing about how to write an Evergreen tax guide. I didn't I knew I didn't want it to go out of date in a year and it does not. I

Stacy Ennis (11:26)

Yeah. They need some shelf life.

Hannah Cole (11:28)

yeah, it needs shelf life. So I put QR codes to get the updated number on every single thing where I actually name a number. I give ballparks where it's not necessary to give an exact number. So it is evergreen.

Stacy Ennis (11:41)

It's wonderful.

It's so smart. And I it's especially in the financial space, that's very hard to do.

Hannah Cole (11:47)

Mm-hmm.

Stacy Ennis (11:47)

but you you know, you approach that really thoughtfully. It also brings people into your ecosystem so you can serve them better through, you know, a future book or future offerings or anything that comes up.

Hannah Cole (11:59)

For sure. So tell me, I it y I know you listened to my episode where I talked about how I broke down the like the author journey of publishing a book. And you know, of course I'm an I'm an experience of one and you have experience. You have so much more exponentially more author journey experience. So I'm kind of curious reflecting on my interpretation of that journey, what you would what you would add to it.

Stacy Ennis (12:24)

Hmm. I listened with great interest. I was very interested in hearing your experience and you know, insights from there there is something to be said also about having been in this so long and having such a wide range of experience that I n will never get to approach it for the first time again. Like you get to have that experience. So I also get to learn from you in in your journey and your experience. It helps me help.

other authors as well. So I got a lot out of it. I highly recommend everybody to go listen to that. I think that the layer that I would maybe add to your experience is that you took the traditional publishing route. And that is definitely not all that's available for authors to to consider as their pathway to publishing. And I would particularly highlight underrepresented authors. We have a very white

not very diverse industry that gatekeeps books. And although there's been a lot of growth and change within publishing, it's still a very antiquated industry like many are, and has a lot of room to grow. So, you know, authors of color, queer, disabled authors, you're just gonna have a harder time than like a white female or a white male who's out there

Trying to get picked for these opportunities. And so I I think that it's really important for authors to know that the gates can be opened by you through different routes. And yet, while we have more access through self-publishing and hybrid publishing, you as an author, especially if you're not working with a really reputable publishing partner like a hybrid publisher.

you now need to take on many of the things that Hannah talked about, that Hannah that you talked about in your episode, around your positioning, really understanding your reader, your market research, your planning. And where I see a lot of authors frankly quit or fail is that they don't do a lot of that early planning outlining. And part of what a book proposal can be really useful for is that planning process.

Hannah Cole (14:36)

Mm-hmm.

Stacy Ennis (14:36)

It's not

always necessary to do that f in the way that you did it, Hannah, if you're going the self-in hybrid publishing route, but you do components of that to prepare yourself for the writing process. So I think that that's just one layer I would add is that there's other routes that you can take. It doesn't have to be the traditional route. Certainly there are pluses to that. There's also minuses to the traditional route, pluses and minuses to self-publishing and hybrid publishing, which is

You know, if that's a new term for people, that's like a kind of middle ground between traditional publishing and self-publishing, where you pay a partner publisher to produce your work. So they are really creating the product, often engaged in the marketing. so there's a lot of routes and I I think that that might be something that's an interesting layer to dig into.

Hannah Cole (15:27)

Yeah. you know, that wasn't my experience, but a lot of people in the author's influence circle which you run are are approaching it that way. And you have a lot to share on that. So I will like those of you listening who resonated with Stacy's message about, you know, if you're hi in a historically marginalized group or just maybe the economics or time, of a book feels

scary to you, I definitely recommend that you go look on Stacy's website and poke around at what she offers because she's really good at this, like, you know, laying out what the journey looks like for the different types like hybrid and self publishing, which are definitely viable viable options and becoming more viable. Would you say

Stacy Ennis (16:09)

Mm-hmm.

Hannah Cole (16:09)

that's correct?

Stacy Ennis (16:11)

yeah. I I recently did a an interview on my podcast, which you've been on, Hannah, Beyond Better. And I interviewed Emma Lowe, who's the director of the London Book Fair, which is one of the largest industry conferences in the world. And one of the things that I thought was really interesting about this fair that I attended back in March, and we talked about on the episode, is that they they have this whole author education.

Component of the London Book Fair. And as part of this kind of wider trade show that they do, they provide author education and they had a lot of authors on stages. They had a lot of education around publishing. What I thought was really interesting is that they had many self-published authors on stage alongside traditionally published authors. Many of them had started traditional and went self-publishing, which I thought was very interesting that they

Hannah Cole (17:03)

That

is.

Stacy Ennis (17:04)

And I really appreciated the way that they gave the space to vr a variety of publishing routes because, you know, especially with a trade show like that that's for it's a deal making conference for traditional publishers. Like that is the the heart of it, especially for translation rights. So by all, you know, accounts, they have every right to highlight and focus on traditional.

But self-publishing, hybrid publishing had a big imprint there. Like imprint, I I guess is a publishing term, but I mean like in a different way. you know, they had

Hannah Cole (17:37)

Yeah. Yeah.

Stacy Ennis (17:40)

a big footprint and were very visible. And in fact, Ally, which is an independent authors organization, ran that whole stage. So I I think that it's, you know, it it's growing, but it's also becoming a preferable route, actually, especially for

genre writers, which Emma mentions in that podcast episode, but for nonfiction, definitely, because a lot of the authors I work with have an integration in their business. And there's a lot of things that you don't get to control in the traditional route. And the time to market is very, very long. So if you have some, you know, business or brand or social impact growth goals, they might not want to wait three years to get the book out into market. They'd rather

you know, take it into their own hands and work on more of like an 18 month timeline, let's say. So there's, you know, there's again always pros and cons. And there's never one right route that I could say is like, this is the way I recommend for every single person. Budget comes into play, goals come into play. you know, do you have like the interest in exploring the traditional route? And like,

Hannah Cole (18:49)

Mm-hmm.

Stacy Ennis (18:49)

is that exciting to you?

And and

Hannah Cole (18:51)

Yeah.

Stacy Ennis (18:52)

if it is, then and you want to go that route, that's wonderful. But I also recommend that people put parameters around that and have a mindset of I'm gonna do this no matter what, like I'm gonna get this work out into the world no matter what. Because if we're always just waiting for somebody else to deem us worthy or to give us an opportunity, like what? We have so much availability to us now to be able to create our own opportunity and and to put our own work out into the world.

Hannah Cole (19:21)

Yeah.

Stacy Ennis (19:22)

so I I just like authors to know that that there's a lot of routes and one is not better or more worthwhile than another. and that you can explore all the different ways to get a book out.

Hannah Cole (19:37)

That's awesome. So to the person who's listening to this who doesn't identify as a writer, but who's, you know, a thought leader, somebody who's built some expertise in their business, presumably serving a population, kind of like me, right? I didn't identify as a writer, but I do a lot of writing and I do have a mission and a thing to teach. Like I think there's a lot of people like that where they might play with the idea of a book, but they feel very uncertain kind of

Does this make any sense? Does it make any sense financially? Does it make any sense like audience wise or business wise? So one of the things I love about you, Stacy, is how you are able to kind of place that within the ecosystem of a business, of somebody who is kind of a leader in their field. Can you talk a little bit about like what kind of a role a book can play and and ROI in terms of yes, money, but audience or other benefits?

Stacy Ennis (20:28)

Yeah, yeah. it's interesting. I I'm prepping for presentation I'm going to provide a speakers group tomorrow. And as

Hannah Cole (20:36)

Mm-hmm.

Stacy Ennis (20:37)

part of that prep I I always like to see what data points I can bring in because that can be really useful. And I came across this report, the name of the the company that did the the

analysis is escaping me, but I can send it to you later, Hannah. Maybe we can link to it if you if you want to. But it's

Hannah Cole (20:53)

Yeah, I thought.

Stacy Ennis (20:54)

on visible experts. So the idea of a visible expert is it's somebody that is, you know, out there creating in a visible way. So they're becoming known in their space. You would be a visible expert, I think, from their definition. And they had these two charts. One chart is most popular marketing things that they do. So it's like

this list of, you know, social media, speaking, referrals, all of these things. And at

Hannah Cole (21:22)

Mm-hmm.

Stacy Ennis (21:23)

the very bottom is writing a business book. Like that was or writing a book on their topic or something like that. The bottom of popularity. But then they had a chart of most effective marketing strategies. And number one was speaking and number two was writing a book on your topic.

Hannah Cole (21:44)

Amazing.

Stacy Ennis (21:44)

and the referrals

were three, I think, in that list. And so while I think in the original list it was like social media was pretty high up, and these other these other things that are maybe a little easier, a little more accessible, they are not the necessarily the most effective when they surveyed this group. I think it was two hundred and fifty visual visible experts. And I thought that was such a cool

data point because it's like anything else. Often the thing that is the effort, it's the bigger thing that's the heavier lift. they're really unpopular. Not everybody wants to do it or will do it. Maybe they want to, but they won't follow through. we know that, you know, about 80% of people want to write a book, but less than 1% of people actually do. And so I think that, you know, a book is such a

Completing and publishing a good book, I think that that's a really important note there. It has to be a good quality, well-done book, can be

Hannah Cole (22:44)

Mm-hmm.

Stacy Ennis (22:45)

such a powerful differentiator for you as whatever you are, a coach, a consultant, a creator of some kind, a service provider, you know, whatever you're out there doing in the world.

so there's there's that one piece from a

just simply a marketing perspective. We know that it's effective and it's long-term effective. It's it has a much higher shelf life, as you know, we talked about that earlier, than a viral reel or even a s a a really great workshop or talk. You have to keep delivering those over and over again as marketing strategies. But a book,

Hannah Cole (23:17)

Mm-hmm. Yeah.

Stacy Ennis (23:19)

of course you have to market it, of course you have to do the work of getting visibility around it, but it's completed and it's out in the world.

And so there's these pieces that we know a book can deliver. Status, I hate I hate might be a strong way, I strongly dislike that this is part of our human experience, but it is. And we as humans take in signals about people to decide if we can trust them. And a really strong trust status symbol is an author, because you've done that work. it is an access point to rooms and stages that

would previously be hard to get into because you lack that status. there it can be used as a marketing tool, a lead gen tool, you know, podcast pitching tool. Like there's all these things that you can do to really leverage it. And we know

Hannah Cole (24:04)

Yeah.

Stacy Ennis (24:04)

all that stuff, but I I think that the thing that gets talked about less or maybe is less well known is that the experience and journey of organizing your ideas

Not just to organize your ideas, but then translate those in a way that other people can understand, remember, and use. That is a process that you grow in such a deep and profound way and you arrive on the other side of this changed. You you're clearer, you're more confident.

Hannah Cole (24:38)

yeah.

Stacy Ennis (24:39)

Yeah, I'd love to hear from you, Hannah, if that was your experience with your work.

Hannah Cole (24:43)

Yeah, I mean it's the workout of your life. I mean, I kept thinking of it

Stacy Ennis (24:46)

Yeah.

Hannah Cole (24:47)

in terms like that. Like I I I do weight training. I've been like

Stacy Ennis (24:50)

Love that.

Hannah Cole (24:51)

and it it is that it is like you can't do it all in one day. It is a way bigger project. Like you're kind of building your strength over daily writing or or weekly, you know, I mean your pace is your pace. But yeah, it's it's strengthens what you are already expert in. It strengthens and clarifies and

I think I remember a business coach, somebody huge, like Alex Hermozzi or something, was talking about like a little metric of like what you should do in your business. There's like high impact, easy to do, high impact, hard to do, low impact, easy to do, low impact, no impact. you know, doesn't do anything for you. So obviously we forget that quadrant altogether. And he's like, Well, as a business owner, what's left for you?

You've already done this stuff that's high impact and easy to do. The only thing left is either to go to things that won't move the needle or to start doing the hard stuff. Like, and so like

Stacy Ennis (25:49)

Mmm. that's so good.

Hannah Cole (25:51)

high impact, hard to do is something that separates you from the pack. I mean, it is easy to put up an Instagram reel, relatively speaking. And it is not easy to write a book. So of course it's a differentiator.

of course it tells people you're serious, you're committed, because you you can't, you cannot write a book without that. Not to mention the book process itself makes you better at what you do.

Stacy Ennis (26:19)

Yeah, a hundred percent all of what you said. And I and I I think that, you know, because also it's a long journey of introspection and and particularly in this time that we're in globally with the you know AI and all of that, I won't I'm not gonna take us down that rabbit hole. But you know, it is a trained intentionality. Like you have to really show up in deep thought.

And you have to sit with your thoughts and you have to work through those thoughts. And and this is if you do it with with integrity, if you go through this process with integrity, because we now have tools that can steal some of your integrity and your creative process. but if you go through this process with integrity and with a real quest of service and creating something lasting and meaningful and useful and

You know, Hannah, in your episode that you recorded, you talked about, you know, not wanting it to be a big long sales book that's like just sending people to all the things you sell, really making

Hannah Cole (27:19)

Mm-hmm.

Stacy Ennis (27:19)

it an all all contained useful thing. Like that is hard work. That is not an easy thing to do. It requires so

Hannah Cole (27:28)

Mm-hmm.

Stacy Ennis (27:28)

much thought. And so that process of thinking and organizing, I imagine that also impacted other things that you do in your business.

Talks that you're giving, interviews you're giving, maybe I don't know if you've grown any new products or any new like service items out of some of that thinking I I or maybe will. but

Hannah Cole (27:47)

Yeah, a little.

Stacy Ennis (27:48)

that's like it's a seedbed for growth for other personal and and business and brand growth.

Hannah Cole (27:54)

Yeah, absolutely, absolutely true. I think you know what, like just to speak to this moment that we're in right now, one, I think we're in a trust recession. I didn't invent that term and I can't attribute it, but the internet says this.

Stacy Ennis (28:10)

Okay.

Hannah Cole (28:11)

I think a book is a really nice antidote to the trust recession. Like it just takes so much commitment to write one and integrity. I mean, yes, if you if you do it the right way.

That it is in part an antidote to that trust thing. Like you build a trust with someone as they read your book. and I also just want to say on a personal note, like as AI creates all this slop and shallow thinking, I think this is why I feel so attracted to authors and writers lately. I'm a mega reader. Anyone who is

follows my substack knows that I like recommend a book every week and you can tell I'm reading a book a week. But like I'm so attracted to reading and to authors because it's a place for deep thought. It's a place for integrity.

Stacy Ennis (28:58)

Mm, mm-hmm.

Hannah Cole (28:59)

It's a place for like deep, deep human connection. and I don't know about you, but more than ever right now, the AI era is making me more into books because of that.

Stacy Ennis (29:10)

yeah, for sure. And I've definitely the last six plus months I've really moved away from a lot of I mean, I'm still on all the platforms and doing all the things, but I the the the what was it? You said trust recession? Is that what you said?

Hannah Cole (29:25)

Trust your session.

Stacy Ennis (29:26)

That's so good. interestingly, I'm I've been I'm prepping for

a conference later this year here in Portugal. It's called Book 2.0. And I'm moderating a panel. And I was just chatting with Matt of, he founded the London Writers Salon, and he brought up this term called creative health, which is not a term that I'm familiar with, but it's something that apparently a lot of people are curious about and studying and interested in.

And I I love that as a concept because I think as we, you know, we think about all of these areas, mental health, physical health, spiritual health, creative health, it's a real thing. Having space in your day and your life for creative, thoughtful work, I think to your point now more than ever, and as we, you know, it's also like

I think that some authors, future authors, aspiring authors, are are also in maybe a self-trust recession because they're outsourcing so much of their thinking and creative work that they don't trust themselves to create with their own brains anymore. And

Hannah Cole (30:32)

You're so right.

Stacy Ennis (30:34)

So this is something that I'm I'm I'm having calls with a lot of authors who are really nervous about the way that I work and the my guidelines around AI. I and I on pretty much every call, I'm like, listen, not every call, but a lot of them. Listen,

Hannah Cole (30:50)

Mm-hmm.

Stacy Ennis (30:51)

you've been using your brain and only your brain for decades. We have been writing books and creating we've been telling stories for 30,000 years. And we are

capable of creation and in fact your beautiful human brain is completely powered to do this all on its own. And I think that

Hannah Cole (31:15)

Mm-hmm.

Stacy Ennis (31:16)

some of this process of writing a book or whatever it is, creating whatever it is in the world, we're rebuilding that self-trust, like that is just a foundation of self-belief. And yeah, it's important. It's important.

Hannah Cole (31:32)

That's

that's beautiful. I mean, again, strength training has is my metaphor for everything in life, but I would you go to the gym and put your weights on a forklift and have the forklift lift the weights for you? Like you can recognize how that

Stacy Ennis (31:43)

No, no, you wouldn't you'd atrophy. Yeah.

Hannah Cole (31:46)

is not going to build muscle for you. Like

Stacy Ennis (31:49)

Yeah.

Hannah Cole (31:50)

the way to build the powers of your brain is to do the powerful work. Like and it's hard. Like that's the whole point. That's why not everybody does it.

Stacy Ennis (31:59)

And the people that do are the people that are going to outlast all of the

kind of hardships that we are seeing in AI. I think the people that will stay the course and do

Hannah Cole (32:10)

I agree.

Stacy Ennis (32:10)

the thinking, they're going to lead what will be, and I think already starting to be a creative revolution. So I think that there's not just, you know, the virtue of the work, but I think there's a real like professional imperative, a societal imperative, like this is all

it's important. And I think that a book is a very practical expression of that. Like it's a project that you can do that taps into all the things that we're talking about and it also moves your business forward. Like it's

Hannah Cole (32:44)

Yeah.

Stacy Ennis (32:44)

kind of the perfect project in my view. it contains a lot of things.

Hannah Cole (32:47)

my gosh, Stacy creative revolution, the antidote to

what ails society right now. Like, let's leave it there. We can't do better. Amen. I love it.

Stacy Ennis (32:53)

Yeah.

Hannah Cole (33:01)

I I so agree with everything you said. I don't feel like I can do any any better than you just did. So thank you.

Stacy Ennis (33:08)

Ha ha

Hannah Cole (33:10)

Beautiful. And I agree. I'm on this team. Stacy, I I want to point to the session that we did together, and let people know that if if you're interested in hearing Stacy's wisdom, getting down into the nitty-gritty numbers, into the self-publishing thing, to the actual writing journey, if you're starting to think, maybe this is like something I wanna look at.

They can get that the recording of our session by just you just have to be a subscriber. You can just be a free subscriber or paid to my Substack Taxes for Humans. Send an email to hello@sunlighttax.com and just say you want the recording or send me a note on Substack. But with that said, knowing that people can get that, I also want people to just hop on your website, take a look at what you offer because you're really brilliant in many areas.

And I think you've definitely given people a taste of why maybe they might be interested in that. So Stacy, where can people find you?

Stacy Ennis (34:06)

thank you, Hannah. You can find me at stacyennis.com at Stacy with no E. and if you go to stacyennis.com/10things that's the number 10, I have a free guide that you can download, fully created by me with no AI.

that really will give you an overview of things that you need to know before writing your nonfiction book. And this is a guide that has helped so many authors. Even if you don't work with me, I would love for you to get this because it's gonna give you, you know, a really solid foundation. It's like a quick and dirty download of of 10 things that you should really know go before you go into this journey. and I'm also on Instagram at Stacy Ennis and on LinkedIn.

Hannah Cole (34:45)

Lovely. And also your podcast is great, Beyond Better. lots of

Stacy Ennis (34:48)

Yes, and I had a great

episode with this amazing woman named Hannah Cole. So they can go listen to that one.

Hannah Cole (34:54)

Yeah.

Lovely, lovely. It's a great place to explore topic by topic. Stacy, it's just you're brilliant and wonderful. I love the work you're doing. And also like you're serving people who have a mission in this world, help them get their voice out there. That's what I think of myself as doing on the money side. And so I feel very aligned with you and I love the work you're doing. So thanks for being with us today.

Stacy Ennis (35:18)

Thank you, Hannah. I really appreciate the opportunity to connect with your people through this podcast and just through your partnership and collaboration and helping make the world a better place.

Hannah Cole (35:30)

Yeah, let's make great people help great people do great work. Awesome. All right. Well I will see you again in your in your membership and thanks for being here.

Stacy Ennis (35:41)

Thanks, Hannah.

Tessa Fontaine: BTS on Writing Fiction: Money, Career, and Why Writing Matters

Listen and Subscribe Here

“The parts that allow me to feel connected to other writers... that’s not a conversation I can have with many people in my life.”

— Tessa Fontaine

This week on the Sunlight Tax Podcast, we go behind the scenes with writer Tessa Fontaine as we explore the realities of building a fiction writing career. We talk about money, publishing, creative community, balancing art with financial stability, and why most authors rely on multiple income streams to keep writing.

We also discuss the deeper purpose of writing—how stories help us make sense of the world, why art matters beyond profit, and what it means to create work that truly connects. Whether you're a writer, artist, or creative entrepreneur, this conversation is an honest look at the intersection of creativity, career, and purpose.

Also mentioned in today’s episode:

00:10 Introduction to Tessa Fontaine's Writing Journey

03:18 The Role of Income and Writing as a Creative Outlet

04:18 The Joy of Reading and Audiobooks for Writers

06:36 Balancing Practical Career and Artistic Spirit

11:36 Building Community and Accountability in Writing

22:34 The Fickleness of Writing Income and Artistic Freedom

27:54 The Incompatibility of Capitalism and Art

36:36 The Gift Economy and the Purpose of Art

46:06 Why Do You Write? Personal Motivations

50:40 Diverse Careers and Income Streams for Writers

54:29 Misunderstandings About the Financial Side of Writing

01:00:02 The Enduring Power of Art and Literature

If you enjoyed this episode, please rate, review and share it! Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.

About Tessa Fontaine:

Tessa Fontaine is the author of  THE ELECTRIC WOMAN: A MEMOIR IN DEATH-DEFYING ACTS (FSG 2018), a New York Times Editors' Choice; Barnes & Noble Discover Great New Writers pick, and best book of the year by Southern Living, Refinery29, Amazon Editors', and The New York Post.  

THE RED GROVE (FSG 2024), her debut novel, was named a best book by Amazon Editors’ and People Magazine, and was currently longlisted for the Center for Fiction’s First Novel Prize.

Other writing can be found in Outside, The New York Times, Glamour, AGNI, The Believer, People, LitHub, Creative Nonfiction, and more. Raised outside San Francisco, Tessa is a former professor and has taught in jails and prisons. She co-founded and teaches the Accountability Workshops with writer and pal Annie Hartnett, and lives in Asheville, North Carolina, with her daughter, goofy dog and sassy cat.

Check Out Tessa’s Work:

Tessa’s Website

Accountability Workshops website

Instagram: @accountabilityworkshops 

Episode Links:

Check out my program, Money Bootcamp

Get my Tax Help on Substack

Get your FREE visual guide to tax deductions

Order my book:Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed

Watch YouTube video version

Transcript:

Tessa Fontaine (02:14)

Thank

you. Thanks, Hannah. Thanks so much for having me. I'm so delighted to get to talk to you here.

Hannah Cole (02:20)

Me too. True confession, all I ever want in life is to talk about books and when I when we met

Tessa Fontaine (02:27)

Ha ha ha.

Hannah Cole (02:28)

at a mutual friends party, I was like, I just wanna corner Tessa at every party and talk about books, which I have actually followed through on sometimes.

Tessa Fontaine (02:37)

Yeah, but it you know, the reason that we got along is 'cause it's all I also want to talk about. I just wanna

Hannah Cole (02:42)

Yeah.

Tessa Fontaine (02:43)

like geek out with people about how good books are. And so that's we're kindred spirits.

Hannah Cole (02:48)

I love it. I also like I remember we had a drink one time and I remember asking you about books and talking about books and realizing that you are reading so much like I get the luxury of reading whatever I like because it's just pleasure for me. And you as a professional writer and coach and editor have so much student work that you have to read that you have less time than I do for like novels.

Tessa Fontaine (03:14)

Yeah, I just had this funny experience actually where someone someone was like, what are the top three books you read that you loved in the last year? And I am reading all the time, but I was like, I don't even know if I've read three books I would say I love. Not because I haven't read three great books, but I just like as you're saying, so much of my time is like reading for blurbs or reading for an event I'm gonna do with someone, or reading student material, or you know, doing an editorial project. And so

It's all great and I love it, but my mind really goes blank in those moments. I still do get to read a lot for pleasure. And actually the thing that my reading pleasure crossover is I'm a huge audiobook fan. And

Hannah Cole (03:51)

Hm.

Tessa Fontaine (03:52)

like at the end of a day, sometimes I'm like, I don't think I can read more. My eyes are too tired. And so I'll listen to a book while I'm like doing the dishes or doing something in the garden or something. And that feels like I can still be swept away with the story without having to sit still or

trained my eyes in and so that's my like little pleasure zone of reading these days.

Hannah Cole (04:12)

I love that. Yeah, that's really cool. audiobooks do feel like a gift to the world. They unlock so much.

Tessa Fontaine (04:17)

Yeah, yeah. Thank you. Thank you, people who've

I know. It's so great.

Hannah Cole (04:21)

Yeah. Like being

able to yes, like pull weeds or wash dishes, pack lunches. It's so good.

Tessa Fontaine (04:27)

I know. While while

someone just t like really beautifully narrates a story to you, like, it's just like it's like childhood dreams coming true. It's the best.

Hannah Cole (04:35)

Kinda

kinda is. Also like the New Yorker fiction podcast is also that is life to me. there

Tessa Fontaine (04:39)

Yes, totally, totally.

Hannah Cole (04:43)

I don't love every story, but sometimes one just hits me so hard I feel like my whole day gets turned on its head.

Tessa Fontaine (04:50)

Yeah,

I'm with you. And that you get to hear what other writers geek out on that you're like hearing you kinda get two different brains in on it 'cause it

Hannah Cole (04:58)

For sure.

Tessa Fontaine (04:58)

it's like a writer who's like, Here's my favorite story.

Hannah Cole (05:01)

I think part of what I love about that so much is exactly that part, like where the writers saying what they were attracted to in the story and pointing out moments they thought were genius. It just helps me appreciate the craft of writing so much. Yeah.

Tessa Fontaine (05:15)

Totally. Yeah.

Hannah Cole (05:17)

I think I would go back to school and try to get an MFA in fiction writing, like just so that I could talk about books all the time if practical reality was not a factor in my life.

Tessa Fontaine (05:28)

Yeah.

It is so fun. Yeah.

Hannah Cole (05:32)

so I wanna kind of sandwich this conversation. Like this is a podcast people come to for practical stuff and the career side of creative life. but I wanna talk about the spirit too. So I wanna ask you actually a practical question up front. I wanna orient people to kind of I mean I read your official bio, but I'm really interested in like

just the facts kind of of like, well you run this coaching group, you have this retreat like what is your kind of writing life career look like? And then maybe talk spirit and then go back to practical. So nuts and

Tessa Fontaine (06:07)

Yeah.

Hannah Cole (06:07)

bolts, spirit, nuts and bolts again.

Tessa Fontaine (06:10)

Great. Yeah. You know what? It's it's funny actually, as you were reading that bio, I was thinking like, this is the bio I send when I'm doing like a literary event, but it's actually not the bio that has my actual larger work life in it really. because

Hannah Cole (06:23)

Mm-hmm.

Tessa Fontaine (06:24)

it doesn't mention what I actually do most of the time, which is writing related, as you say. So so my life so I have done a lot of things, I think as many creative folks have. And I I kind of first went down the academic road and so I was a

professor of creative writing and always honestly knew that that was not the right road for me. I I love teaching, but not really in academia that that traditional undergrad academia wasn't exactly the right fit. And so I left that and so I started real like kind of immediately after leaving that, I started something I had a I had a writing partner, really who she was just a friend, Annie Hartnett. And we had been writing

writing partners really for years and and the way that that started is we both had our first books come out and then we both got really, really, really stuck writing our second books. I think it was a little bit of the Cheryl Crow like the first cut is the deepest. Like we had written our first books and we were both kind of like, well we've said everything there is to say like what how do you write another book? How do you do this? And so she had found this Amy Bender essay.

That was published on Oprah.com, which I recommend to everybody, where she basically talks about, I think it's called the way to get productive is to make rules. And it was about making this kind of contract, this like binding legal contract with another writer friend, where they agreed to certain stipulations, like I'm gonna write a thousand words a day, four days a week. Here, you know, if I'm traveling, here's what I'm gonna do instead. Here's how much reading I'm gonna do. Here are some things I need to remind myself, here are the conditions I'm gonna.

Keep the internet off. I'm gonna have light a candle, whatever. And so they put all these things in this contract. Then when you do it for the day, you just simply tell your writing partner, done, and then they write back check. So you're not ever turning anything into them. You're just sort of saying, I did my contract for the day. Annie and I started doing that years ago with each other. And it really, really, really helped. It really helped to have an accountability partner. It really helped just to have somebody

Who I didn't have to sort of explain all the things to, but I could kind of be in my weird world and then have a little touchstone to the outside with her. And so we started that together. And then that at at one point years in, we were like, What do you think other people would like this? should we try to like invite a few people in and see if we can like make it a business? We you know, we were like artist people were like, we don't have businesses, we don't even know, you know, who has a who has a bank account, right? Anything.

Hannah Cole (08:50)

Yes.

Tessa Fontaine (08:50)

But we're like, okay. And we started

it and that was in 2022. And it has since grown and grown. And so this is really the the center point of my working life is I run accountability workshops. And they are I think we have eight cohorts right now of about 15 people each, and they're folks who want to be finishing their books and want to be working on their projects, and so they meet in individual cohorts.

And then we have a lot of other systems of support around them monthly speakers, book clubs, online cave writing sessions. Everybody makes this contract and does the daily check ins. So this is a big part of my work life right now, of my business life. that came just out of something that I had been doing for myself. So that's a big piece of my puzzle. I also teach in an MFA program now in Warren Wilson's MFA program. and that I like

a lot that is a better fit for me than kind of teaching in traditional undergrad classes. I'm working with older writers who are kind of more serious and more excited and that that that feels really fun. and then I do some kind of editorial work sometimes on the side and I run, as you kind of mentioned, a writers camp every fall, which

has about forty participants and four faculty and two agents and we do it in New Hampshire among the fall leaves and it's like five days of intensive writing time and craft classes and meetings with agents and and faculty and it's so fun dance parties fires it's great. So my working life and then I write. So my working life is very much like lots of puzzle pieces moving together and I'm really grateful for it.

Hannah Cole (10:32)

Yeah. Wow. It does it sounds like a lot, but I the community sounds to me wonderful.

Tessa Fontaine (10:39)

Yeah. Yeah. The community is amazing. I think like I think, you know, this isn't it isn't true for every creative practice that you are alone. But there are a lot of creative practices that you c you kind of do the thing alone. Like I feel really jealous sometimes when I talk to screenwriter friends who are in a writer's room and are like in this kind of collaborative space all the time. But like that's not what I do as a novelist or memoirist or essayist or when I'm writing for the paper and stuff. I I'm I'm like in this little

I don't know, I it just like this little cave. And so the parts that allow me to feel connected to other writers and to I mean, kind of what we were just talking about at the beginning, like geek out on books, like where we're like, my gosh, here's this life-changing thing, here's why it's life-changing. Like, that's not a conversation I can have with many people in my life. Mm, you know, not a lot of people feel that same way. And so it does feel really special to be part of it and to kind of I guess have also helped just create the space for

a lot of folks to get this kind of connection that they didn't have before. It it's felt really great.

Hannah Cole (11:42)

That's beautiful. I mean, you know, honestly, the analogy to visual art is perfect. you know, I I other visual artists mostly make work alone in a studio. And you need a critique group I mean, I think there is objectively kind of more expert work.

But it's also subjective and you don't always see everything that's in your own work and it really does. It is so helpful. Like just that same way that you need to talk about your writing with other writers. You also need to

Tessa Fontaine (12:11)

Mm-hmm.

Hannah Cole (12:12)

analyze and sit with artwork, I think, in a in a group setting and hear the way other people react to it to know if you're getting across what you mean to.

Tessa Fontaine (12:21)

Yeah. Yeah. Totally. And and and so I have also like my own writing group. So I have accountability workshops that I kind of run for a lot of other writers. And then I have my own writing group that is three other writers and I that's maybe,

Hannah Cole (12:33)

no.

Tessa Fontaine (12:33)

you know, similar to the critique group too, where we do exchange full drafts and but even more than really the thing that I think is the most valuable, you know, on top of like exchanging full drafts is we just meet and just talk about

like norm things with each other. It was the first time I ever, I mean, here we are in a creativity and money podcast. So this is perfect. We got we got together and we're like, let's be honest with each other about all of it. Like let's say how much money we got for advances, which I had never happened. I had never encountered anyone being forthright about money or about what your contract was like. There's like this veil of secrecy that I think really benefits the publishers. And I think this is true

Hannah Cole (13:13)

yeah.

Tessa Fontaine (13:14)

in

you know, many areas of of art or the capitalism. and so it was like revelatory just to norm things, to be like, where am I? And, you know, what does this amount of money mean? And what is it, what and what did that amount of money mean for you? And like just the norming

Hannah Cole (13:29)

Yeah.

Tessa Fontaine (13:29)

of that, the openness of it was has been really, really helpful, really great.

Hannah Cole (13:33)

my gosh,

that's awesome. I mean, I I'm also an author, I mean a a baby author, but I I published a book and a work.

Tessa Fontaine (13:40)

Yes.

Hannah Cole (13:41)

So I feel like I get to I get to call myself part of this club a little bit.

Tessa Fontaine (13:44)

Hundred percent. You're not a baby, you're a whole grown up author, Hannah.

Hannah Cole (13:49)

Thank you for that. I but I I do feel absolutely sort of dropped down into a dark forest. Like, here you go, here's your money, here's your timeline, we hope you sell books. And I'm like

Did I do good? Like I just don't even know.

Tessa Fontaine (14:04)

Yeah. Yeah. Totally.

Yeah. And like like w w what were we expecting to happen and did it happen? And should like there's just there's so much yeah, you get these little pieces of information and then they're like and then you just are off in the world and and that's kinda it. It's it's really bizarre. And I think like the people who are selling, you know, a million copies of their book know they're doing well because they have a billboard up of the book. But I think

Basically everyone else is kinda like, what where am I? How how's this going?

Hannah Cole (14:37)

Yeah. Well can I a okay, so I was gonna ask these later, but I'll ask you now. Like, is there a big difference between a first time author deal expectation versus it's your fifth book, you have a track record? Like does it does it really shift?

Tessa Fontaine (14:54)

Kind of in two ways that are sort of oppositional actually. there there often is like people love a debut. People love the story of a first time writer. So there so oftentimes people may get a bigger chunk of money and more attention for their debut, for the sort of promise of the new new talent on the scene. at this but then there's also

the beauty of sort of being an author who has put out a handful of books already. You have a readership built in. You have fans who are excited about your book. and so there can be more to build on at that point. So there's sort of like a, you know, sometimes you get more sort of more attention, more support later on.

Hannah Cole (15:38)

Mm-hmm.

Tessa Fontaine (15:39)

But it also is always so dependent on how your last book sold. So there's always this sort of and I think that's like part of why the first book can

be such a big splash because they don't have any data yet on how well your books are selling. And then later, you know, you you might be beloved, but if you didn't, if your blast book didn't do that well, they're like cr they're putting that into the magical number system behind the scenes where they're figuring out how much money and support to give you.

Hannah Cole (16:07)

That's interesting. You know, Taylor Swift has a line about that. You're only as hot as your last hit, baby. She gets it.

Tessa Fontaine (16:12)

Yes, Tay-Tay, she gets it. She's just one of us. I knew it. Yeah.

Hannah Cole (16:22)

I do imagine if you are Tay Tay that the pressure feels pretty intense when you put out an album.

Tessa Fontaine (16:27)

my god. Yeah, yeah.

Hannah Cole (16:29)

so like I do I do respect that, you know, people people at Olympian levels still do have problems.

Tessa Fontaine (16:35)

Yeah, I do too. I would maybe

like choose those problems over these ones, but yeah. It's real.

Hannah Cole (16:40)

Yeah, I know. People are mad

when you have Mount Olympus problems, but you know.

Tessa Fontaine (16:46)

Yeah, that's right.

Hannah Cole (16:48)

so yeah, I was speaking to this nonfiction book coach who I'm in her like she has a I don't know, an author circle. And she was talking about authors who I just attended like a session she did on writing your second book or you know, second plus, and she

Tessa Fontaine (17:06)

Mm. Mm-hmm.

Hannah Cole (17:08)

was saying that nonfiction

authors, she had just read a study who live entirely off of writing their books have on average like between nine and thirteen books out in the world. That's the point

Tessa Fontaine (17:21)

Mm.

Hannah Cole (17:22)

at which they start living off of the book sales.

Tessa Fontaine (17:25)

Wow.

Hannah Cole (17:27)

I yeah, I that one really kind of got me in the gut. I was like,

Tessa Fontaine (17:32)

a lot of Ucks.

Hannah Cole (17:33)

that whole three year process I just went through that was like felt like much more than a marathon.

maybe more like an Iron Man like that. I have to do that nine to ten times before we start getting But does that

Tessa Fontaine (17:45)

To th to thirteen, yeah. But just go ahead and I

Hannah Cole (17:50)

track that was for nonfiction. I have no idea if that relates. I I have come to learn that nonfiction and fiction are two very different worlds.

Tessa Fontaine (17:57)

They are different worlds and even within nonfiction, there are so many different kinds of nonfiction books. So like a self-help book is a really different beast than a a memoir or a collection of essays. So I'm curious about if that's just nonfiction as a whole or if there's a subgenre within there. But I don't know I have no idea what the n what the number would be if we're tracking it to the average

point at which a a fiction writer could live entirely off of their books. But I I'll just say that I barely know anyone who does it. and

Hannah Cole (18:31)

Hmm.

Tessa Fontaine (18:32)

I know a lot of pretty successful writers. And and there are people who do and there are people who have many books out or who have hit it really, really big really quickly. And there are a couple of people for whom that's true. or people whose books get optioned and made into movies or TV.

And then they get the sort of Hollywood money that comes with it.

but yeah, it's it's hard. And I think the and I guess the one of the reasons that it's hard to like put anything specific on this is like, you know, So say say your friend is like, Hey, I just published a novel. You're like, so great. That could mean anything from someone self-published it on Amazon and is paying for it to come out to

Hannah Cole (19:13)

Mm-hmm.

Tessa Fontaine (19:14)

Going through a vanity press, which means it's an independent press, but you are paying them to put your book out, to going through a small press, which is you are not paying them, but but they're maybe giving you either nothing or $500 or $1,000, and the print run is really small, to being at a major publisher with something like a $10,000 advance, to being at a major publisher with like a million dollar advance or or above. So the range is just it's incomparable, right? Like like someone who's

Putting out a small press book and someone who's putting out a book with a $500,000 advance, the just the difference in the number of books that you're gonna sell in your kind of financial life, like it's just it's such an enormous thing. And as we all know so well, like it does not necessarily track on the genius of your book. It, you know, like there are

Amazing works that come out with tiny presses. There are amazing works that never come out at all. I I have like so many writer friends who have projects that are just still living in their computers. And and there are amazing books that come out and get a ton of money, and really not so amazing books that come out and get a ton of money and you know, all of the things in between. So I guess that's all to say like I that's such an interesting number to know that average for nonfiction. And I

Hannah Cole (20:31)

Is that

Tessa Fontaine (20:32)

have no idea what it is for fiction, but I'll say like even my most successful

fiction writing friends, almost everyone is doing multiple things. Everyone's doing

Hannah Cole (20:42)

Mm-hmm.

Tessa Fontaine (20:43)

a a couple kinds of stuff. And I think part of it is like probably just the like little bit of anxiety a lot of us have that like like what tremendous luck. For me I feel this all the time, like what tremendous luck that I get to make a good portion of my income on writing. It is so incredibly lucky. It is not

Hannah Cole (21:00)

Mm-hmm.

Tessa Fontaine (21:01)

the majority of my income, but it but it, you know, it's a it's a significant portion.

And I'm also so aware of how fickle it is. Like all it would take is for me not to sell the next book, which feels as possible as anything else, for that to go away or for it to, you know, go to a small press or something else. And so I think like and I'm a solo parent and I have a four-year-old and you know own a house and all these things where like I actually don't have I can't have my life ha take have my income go away. It's not a possibility for me.

Hannah Cole (21:30)

Yeah. Yep.

Tessa Fontaine (21:30)

You know, and

this is true for most of us in in, you know, unless we were really smart and married really rich, which I regret every day not doing. But that

Hannah Cole (21:37)

Yeah.

Tessa Fontaine (21:39)

my mom was right. but but like so so having other income streams, in some ways it just like frees up the anxiety, the heart clenching anxiety to be like, actually I can kind of write what I want to write right now.

And

I really, really, really hope that it gets published and I really hope I get a good check that goes along with it, but I will not starve and I will you know, my child will have a roof over her head if that doesn't

Hannah Cole (22:07)

Mm. Wow. You know, writing and visual art are really twins. Like they're that that

Tessa Fontaine (22:12)

Mm.

Hannah Cole (22:12)

is the same story. I fe I feel every bit of that as an as a visual artist. I I actually like made a very conscious decision at a certain point. It was actually the point where I had a baby. I was living in New York City, I had my first of two kids, and you know, shit's expensive.

Tessa Fontaine (22:30)

Yeah.

Hannah Cole (22:30)

everywhere, but in New York very especially.

you know marriage and finance kind of hit the fan. we had a lot of fights over money and so I it was like it was clear the writing on the wall was clear to me I needed to make more money. Like just point blank. That was the issue. So I like went on this journey trying to find another source of income. Like do I triple down on my art career and try to like make this go? And ultimately I just kept coming up with exactly what you just said. Like I could hit it big

for one, two, three, five years. And then it all collapses. And this also

Tessa Fontaine (23:02)

Yeah.

Hannah Cole (23:03)

didn't feel like kind of a a steady foundation to raise a child with. It was not like you can

Tessa Fontaine (23:07)

Mm.

Hannah Cole (23:09)

not have the child anymore. Like it just it was justn't gonna work. I was like, I can't

Tessa Fontaine (23:13)

Yeah.

Hannah Cole (23:13)

do that. So I made a conscious decision to separate, you know, to start sunlight tax and to keep it separate from my art practice. And my art has never been better. I mean, I'm I made

Tessa Fontaine (23:24)

Hmm.

Hannah Cole (23:25)

less of it. Like time is finite.

but you know, the last show that I had in twenty twenty-four, I think, twenty twenty three, I had a show at my gallery and the Tracy Morgan gallery, and it's the best show I've ever put on. It's like the best art I've ever made. And I'm so proud

Tessa Fontaine (23:39)

Mm. Mm.

Hannah Cole (23:42)

of it. And it was partly because like I did not need those pieces to sell. That's why they're

Tessa Fontaine (23:47)

Yeah.

Hannah Cole (23:47)

so good.

Tessa Fontaine (23:49)

Yeah. Yeah. That's right. And it it's such a I I love that story. It's such an interesting paradox that there is it's like it's so lucky and amazing. And I try to remember this part too. It's so lucky and amazing to have a creative career where there is money involved, as in people do sometimes spend money because they believe that your art has a certain value to it. Like I don't

I don't want to say like I only create art and I don't care about money and there's no relationship to selling my books. Like I write books and I hope people read the books and that is transactional and there is money involved, you know? sometimes, not always, but but there also is this thing about being unattached but being not dependent on, not entirely dependent on the sort of income that you're making from it, that yeah, I think it just like it it opens up your

I mean, not to sound so cheese ball, but it kinda like opens up your heart a little bit or opens up something inside you to be able to just kind of be like, what is it that I really want to write and make right now? And like there's all these jokes among writers about like I can't even think of the word romanticy. Everyone's just like, I just should write a romanticy, because you know, the like sexy fantasy books are just like those who the people are writing those are just swimming in it right now, swimming in the money.

And and like, you know, and there's all you know, there's like I get occasional moments where I'm like, maybe I should just take a few months and just bang out some, you know, some commercial book and like I, you know, maybe I will at some point, who knows? But but I also just like really, really value being able to follow my own weird brain down its own weird projects and to feel like, yeah, I really, really hope that this gets to go into the world in a way that my other books have. And

All will not be lost if something else happens.

Hannah Cole (25:37)

Yeah, I really appreciate that. By the way, you did you did get a little weird in the Red Grove, I will say. And I it's that's a compliment. It absolutely is a little weird. And I love it about it.

Tessa Fontaine (25:42)

Yeah. Yeah, it's a little weird. Thank you. Mm-hmm.

Hannah Cole (25:49)

It feels like there's something that feels like free and real and cool about that. It's not predictable.

Tessa Fontaine (25:56)

Yeah, it's a little weird. My my next book is I I think it's like somehow it's weirder. It's weird. It's really weird. And it I mean, I think it's like I hope it feels readable and like has a a wide readership. But it also like I just was rereading it 'cause I'm about to get notes from my agents and I was just like, You are a f you are a funky person, Tessa Fontaine. What are you what is your brain doing here? Who why why

Hannah Cole (26:20)

No.

Tessa Fontaine (26:21)

are the beavers having this conversation? Like what are we do what's happening?

Hannah Cole (26:26)

that makes me really happy.

Tessa Fontaine (26:28)

Okay.

Hannah Cole (26:29)

I've really been thinking about this. Like I think we I previewed for you that this is on my mind, but I'm having a real moment. all my life I have reckoned with this, the spirit of art versus the economics of art. you know, even sunlight tax, though it's meant to be my bread and butter and largely is, like it's still dealing with that.

I deal with it both ways. But

Tessa Fontaine (26:50)

Mm-hmm.

Hannah Cole (26:52)

but this recent, you know, in Asheville that they had this big grant that went out and you know, it's like a government block grant distributed through Mountain Bizworks. And it it forced me so I lost my studio, as you know, and twenty years of work. And the grant forces you to put it into a capitalist lens.

And first

Tessa Fontaine (27:12)

Mm-hmm.

Hannah Cole (27:13)

of all, I didn't qualify on the face of it because my art didn't make enough income. I make my art makes maybe almost enough income, but it really didn't. they told me I should apply anyway, just to be fair to them. but ultimately I still didn't apply for this grant because all the questions are about your capitalist case. And I was like, there isn't one. Like honestly.

They wanted me to show comparative months showing the loss in income that I have because of Hurricane Helene. And like honestly, my numbers don't s tell that story. Like

Tessa Fontaine (27:45)

Yeah.

Hannah Cole (27:45)

my income has always been in art pretty unrelated to my effort and my output. It's like, sometimes I hit it big and I make a great sale. I had in one of, you know, in a recent year I sold twenty-five pieces to a corporate c collection and had like a delicious payday.

Tessa Fontaine (28:00)

Gosh. Yeah.

Hannah Cole (28:02)

And then I'll have three years where it's, you know, close to crickets. Like

Tessa Fontaine (28:06)

Yeah. Yeah.

Hannah Cole (28:07)

Hurricane Helene did not particularly do anything to that dynamic in my art. So basically I found that this like kind of last pot of money is floating down the river without me because

Tessa Fontaine (28:19)

Mm.

Hannah Cole (28:20)

like my art doesn't fit in a capitalist metric. and you know, to lose twenty years of work and just kind of feel

I know this is not true, but in my bad moments I say like it's not valued. and I'm not worthy of getting any money to rebuild. Like it's just it's it's hurt. It's hurt my heart.

Tessa Fontaine (28:39)

Of course it has.

Yeah, of course it has. I mean, it's so awful to have to make the case for why it matter. I mean, it's awful to have to make the case for why it matters at all. But to to to say like the only way to assess it is to find this the the sort of like regular system of money is I mean it like on a much, much tinier scale. It's making me think about like I got

divorced last year and had co-owned a house with my ex-husband and I was buying him out of it. Like I'm so lucky to have the money to be able to do that. And I got denied because my income is not consistent. It's pr it's high enough. It's well high enough, but it it

Hannah Cole (29:23)

Mm-hmm.

Tessa Fontaine (29:23)

isn't exactly consistent year over year because it varies, because, you know, and it doesn't vary by it doesn't go below any any markers of alarm. But it just I think it's like

We are in this incompatibility, which is capitalism and art, and it shows up in so many complicated ways all the time. The example that you're giving is such a devastating version of this. I had this professor in my MFA program who kind of amazingly, given the context, was was always like

Hannah Cole (29:54)

Right.

Tessa Fontaine (29:57)

again, he was teaching in an MFA program, and he was like, We should not be teaching writing or any art.

in school at all because school is a place like you're here and you're paying to be here. So there's necessarily this this financial transaction that's associated

Hannah Cole (30:13)

Mm-hmm.

Tessa Fontaine (30:14)

with it. And so his approach was to say on the first day of class he said, okay, everybody in the class, you have an A. You have an A. Doesn't matter what you do. Like semester closed. If you want to never show up again and never, never be present, fine. I don't care. Art is not transactional in this way. So you have an A, forget about it.

Now, given that the, you know, the financial part is like you're you're not gonna fail out of this class and have a sort of financial consequence, you're gonna get

Hannah Cole (30:42)

Mm-hmm.

Tessa Fontaine (30:42)

a good grade. So given that, what how do you choose to spend your time in this semester? What I and he's like, what I'm gonna do is show up every week and we're gonna, you know, discuss fiction, we're gonna write stories, we're gonna critique it. If you wanna participate that in that solely for the sake of the writing and the stories, wonderful. And if you

Hannah Cole (31:01)

Mm-hmm.

Tessa Fontaine (31:01)

don't want to.

I could care less. Go do anything else that you want. And I thought it

Hannah Cole (31:05)

Yeah.

Tessa Fontaine (31:06)

was so such an interesting reframe. And I mean, I've heard this a lot, like in I mean that, you know, this connects to like sort of higher education and art too, where you're sort of like trying to slam like of course there are hard skills you can learn in visual arts and in writing, there's hard skills. And also there's so much of this that's like esoteric and and really hard to explain or just comes from practice or rhythm or whatever it is. And so I

Like I just think we're always trying to make sense of art and an artistic career in a way that is really hard to track onto like this sort of social systems that we already have in place.

Hannah Cole (31:42)

Yeah.

Yeah. I have multiple thoughts here. Like I think

this very week, like I was in a bit of a dark place because of this. And I I literally had to coach myself, like, well, why is my work valuable? Why does it matter? Why does my last

Tessa Fontaine (31:57)

Mm-hmm.

Hannah Cole (31:57)

20 years matter? which is ridiculous. but I was just I was thinking like I was trying to explain it to my husband. I was like, What tell me your favorite song? Like this a song that like moves your heart.

Like you feel feelings whenever you hear this song. Now tell me how much money that that songwriter made from that song, how much, you know, income they derive from their music. Does it have a relationship to how that song moves you? And like, what's the answer? Of course not. It has no. It's not even a little bit of relation, it's zero relationship. And like

Tessa Fontaine (32:34)

Yeah. Yeah.

Hannah Cole (32:35)

sometimes it's Taylor Swift who moves my heart. And you know what?

Like good job, Taylor, for making money off of it. Like a congratulations.

Tessa Fontaine (32:42)

Yeah.

Hannah Cole (32:43)

I have I have no bad feelings. Like, please. But

Tessa Fontaine (32:46)

Same, same. Great.

Hannah Cole (32:48)

sometimes it's this little indie songwriter busking on the streets of Asheville who I'm sure makes nothing, right? Or very, very close to nothing. And it does not matter. Art is not about we have to eat, we have to put a roof over our children's heads.

But art is about moving the spirit. Art is about connecting to our fundamental humanity. Like

Tessa Fontaine (33:10)

Mm hmm.

Hannah Cole (33:11)

that's its purpose.

Tessa Fontaine (33:12)

Do you do you know the book The Gift by Lewis Hyde?

Hannah Cole (33:17)

not only do I know that book, I s I did

Tessa Fontaine (33:19)

Ha ha.

Hannah Cole (33:20)

a I did like a project where I sent someone a twenty dollar bill in the mail based on his gift circle idea. And and it was like a you know, so you and it was like you have to now send something to somebody else. This is all artists, so someone painted a beautiful painting on the twenty dollar bill and then someone

Tessa Fontaine (33:38)

Mm.

Hannah Cole (33:38)

wrote a poem. So we had this like you know what, I had it all

document it online at some point, but that website is twenty-five years old. Anyway, yes, the gift.

Tessa Fontaine (33:48)

I love that you did that. That's so cool.

Hannah Cole (33:50)

Tell us about the gift. It is an amazing book.

Tessa Fontaine (33:53)

Yeah, it is an amazing book. I mean y maybe you remember it better than I do now. I read it a long time ago, but it comes up in my mind a lot. And and I think so it's sort of about this question of art meeting I mean, kind of art meeting capitalism and and the relationship between money and making things. And

Hannah Cole (34:14)

Mm.

Tessa Fontaine (34:14)

and he from what I remember and correct me or add in here, but what from what I remember, he's kind of like positing

this idea that actually like when you're making something, it should be and is part of a gift economy. It's like this free, it it has to be this sort of free exchange. It has to be this in this kind of world of gift giving. And that unfortunately right now it's in a world that has money associated with it. And, you know, I I think he like calls for this sort of like radical change in how we're considering creative work entirely, which, you know, ha hasn't happened and I don't know if it will, but

Hannah Cole (34:50)

Mm-hmm.

Tessa Fontaine (34:51)

But what

my takeaway from that book was from so many years ago is like, consider this, like when I'm writing something and making something, to consider it as something that I am putting freely out into the world, like this little bird that you're letting go out into the

Hannah Cole (35:05)

Mm-hmm.

Tessa Fontaine (35:05)

world as a gift to be like, how can this connect with other people? How what will other people think about and be moved by? Or, you know, what will they take from it? And that just I think is just like this fundamental reframe of

the purpose of what we're doing and the kind of human connection piece of it that is outside of the money connection piece.

Hannah Cole (35:27)

That's beautiful. I haven't thought about that since I did that project and I needed it. So thank you. I'm gonna go

Tessa Fontaine (35:32)

Mm.

Hannah Cole (35:33)

buy myself a copy if I can't locate one. So

Tessa Fontaine (35:35)

Yes Yes

Hannah Cole (35:38)

right. I've I've thought of it before as a spiritual practice, but I

Tessa Fontaine (35:42)

Mm.

Hannah Cole (35:42)

like the gift because this is another like twisted knot that I have been in since losing my studio and my work. Is like, why do I feel such a need for acknowledgement? Like

Tessa Fontaine (35:57)

Mm.

Hannah Cole (35:57)

I can tell myself my work has meaning and worth, but why do I feel so strongly that I need others to tell me that? But I do. my god, I'm gonna cry. But

Tessa Fontaine (36:06)

Mm, mm-hmm, mm-hmm. It's okay.

Hannah Cole (36:11)

it's because it is not like I may make it solo, I may make it in isolation, but it is meant to be received. Like

Tessa Fontaine (36:18)

Yeah, yeah.

Hannah Cole (36:19)

it's not w who who is it who said this? Marcel Duchamp. I think the work of art is completed by the viewer.

Tessa Fontaine (36:25)

Mm, I love that.

Hannah Cole (36:26)

And I think in writing you would say the same if you don't have a reader like it's completed by the reader received.

Tessa Fontaine (36:32)

Yeah.

Well, and at the time when it it's like sort of how I would feel about losing every draft of everything I've ever written, right? Like at the time that all of your work is in the studio, it's still pure potential. It's like all still the potential to connect. Not not the potential like it's the potential to connect. So there's always just like an act of connection, that act of giving that can happen from it. And with the loss of the studio, it like I'm imagining if I lost every draft of everything I've ever written, it's like

that potentiality goes away because the work is gone. And like that, you know, it I don't know, the the the idea of that is so hard to reckon with that like all of this so much of yourself like it it has reached an endpoint and its end point was just with you. And I don't know, that seems I'm sorry. Yeah,

Hannah Cole (37:22)

It's too lonely. It's unbearably lonely.

Tessa Fontaine (37:26)

yeah, that's right. That's right.

Hannah Cole (37:29)

so it makes me want to ask you though, because 'cause really this purpose, like it is that that song that moves you, that that piece of art that you cannot shake out of your brain. It is that novel that like changes your life. But like

Tessa Fontaine (37:44)

Mm.

Hannah Cole (37:44)

do you have a book like that in your life, Tessa?

Tessa Fontaine (37:48)

One that I've read that has moved me in that way. Gosh, yeah.

Hannah Cole (37:51)

Yeah. It could be a small weight.

That was a heavy pressure question. It could be a little weight.

Tessa Fontaine (37:57)

You know,

s so many books really is the answer. So many books. I'll just like I'll I'll say one that came to mind when you asked that, and it's one I haven't actually reread in quite a few years. I think I actually read it when I was in my MFA, and it's it's a book by the writer Michael Undachi, who's a

Canadian Sri Lankan writer. He's best known for The English Patient, which got turned into a movie. But he has this book called Coming Through Slaughter. It's a really brief book. And it is imagining it's it's a novel. It's fiction. And it's imagining the life of this jazz singer or jazz a jazz musician, not singer, a trumpet player, I think, from New Orleans in like, I want to say it was like the twenties-ish. And

the the actual facts known about this trumpet player Buddy Bolden are this he was really young, like 17 or 18. He just sort of showed up out of nowhere. No one knew him or knew anything about him. He just showed up like in in one of the marching music parades and forgetting the name of it. And just showed up in the middle of the parade, started playing and everyone was just like, this is the most amazing musician we've ever heard. It like shook New Orleans.

And there is just there's like there are snippets of documentation about this guy. There is one photo that exists. And so he he was there. He would like new all of New Orleans just like, who is this most amazing musician who's ever been born? He very quickly started to maybe lose his mind a little bit, and then he

Hannah Cole (39:39)

Mm-hmm.

Tessa Fontaine (39:39)

disappeared completely. And that is all we know about like maybe the greatest musician who ever lived, who just appeared so briefly in New Orleans. And so this book by Michael Ondachi.

imagines this entire life around him and sort of like fictionally fills in all the gaps. And and I remember, I mean the writing is incredibly lyric and poetic and it's so interesting. But what I remember so much was like this feeling of the possibility of like, you know, I I had already been writing some nonfiction essays. I had been writing fiction, I'd been writing poetry

And here is this sort of blended moment of kind of taking

Hannah Cole (40:19)

Mm-hmm.

Tessa Fontaine (40:20)

something from real life that we don't know about and lending your imagination to build out the story and doing it in this really beautiful and evocative way. And it just felt so so moving. And here is a book. I mean, when I when I tell people about this book, I have to say, by Michael Andachi, the guy who wrote The English Patient, because that is the that is the book that has money attached to it, right? It was made into a movie. That's how he pay he's legit, he's legit, he's a real writer.

Hannah Cole (40:42)

Yep. He's legit. Yeah.

Tessa Fontaine (40:47)

And this is and this brilliant book is very unknown. Like it is not a book it is not it's hard to find. It's not one of his popular books. And and it but it you know, it was the song that floored me and and has probably very little money attached to it. I don't know, but it doesn't matter. Yeah.

Hannah Cole (41:04)

Fascinating. Interesting. Will you

repeat the name, the title again?

Tessa Fontaine (41:08)

Coming through slaughter. Slaughter is like the name of a town somewhere maybe where he came from or something. Coming through slaughter. Yeah.

Hannah Cole (41:14)

Mm, okay. It

was very evocative though.

Tessa Fontaine (41:18)

Very

evocative, very sort of scary title. But yeah. What about you?

Hannah Cole (41:21)

Yeah. Wow.

Tessa Fontaine (41:22)

What is what is that book for you?

Hannah Cole (41:25)

I've a million, truly a million. I will say that like of late Elizabeth Strout, hardly unknown. though I've met her.

Tessa Fontaine (41:38)

Ooh.

Hannah Cole (41:39)

my my dad runs an author series in Maine, like it's called An Evening with Maine Authors. So I've read I've met and read a lot of Maine authors, and that is how I discovered Elizabeth Strout. But once I started reading her, I was like holy shit, this woman is a

Tessa Fontaine (41:54)

She kills

me. She's a genius, yeah. Yeah.

Hannah Cole (41:57)

She's a genius.

her way of like getting into getting you into somebody else's head, which I think is what like some of our human empathy is attributed to the invention of the novel, because it was really

Tessa Fontaine (42:10)

Mm.

Hannah Cole (42:11)

the first time you could engage that deeply into somebody's interior life. Although I though I've heard that, I actually think if you read letters like old letters between historic figures, like hmm.

say people were writing a lot of deep internal stuff in their letters. So I'm not sure that's true.

Tessa Fontaine (42:28)

Yeah. Yeah. Totally.

Hannah Cole (42:32)

But she's she's incredible. Just the way she describes like the little secrets that spouses keep from each other in a marriage. like the little assumptions you make that are wrong about people. I just love her. Like I

Tessa Fontaine (42:48)

I agree with you. Yeah. Yeah. I I think she I totally. I think she she help she makes us know the people she's writing about who are make believe people so quickly and so deeply and makes us care about them. And really like I I've tried to describe Elizabeth Strout novels to friends and I'm like they're like, Well what happens? And like, I not a lot I don't know. People go for walks and

Hannah Cole (43:16)

I know.

Tessa Fontaine (43:17)

I don't

someone has a cr secret crush. I don't know. You know, there's like not they're not really plot driven and yet feel so I don't know, they feel so I yeah, I agree with you. Also okay, so this means that your dad also knows Lily King. Is this true?

Hannah Cole (43:32)

Yes, yes. She was actually invited to be the author this year, but she was on she's become so popular. Rightfully, holy cow, that book blew

Tessa Fontaine (43:38)

Yeah, yeah.

Hannah Cole (43:39)

my mind. but she's was on tour in Europe at the critical date. So sh I think she may be next year's speaker, possibly. Fingers crossed. Yeah.

Tessa Fontaine (43:47)

Amazing. Yeah, yeah. Cool. Yeah.

Hannah Cole (43:52)

yeah, but she's amazing. I think I don't know. I c you know what? I think we've established that I could probably spend

three hours on this podcast or p potentially three weeks just telling you about all my favorite books.

Tessa Fontaine (44:04)

That would

be a fun series of episodes. Just Hannah talks books.

Hannah Cole (44:09)

I mean, you know, it

is my newsletter like in my newsletter I do actually just my newsletter itself makes me read more because I try to almost every single week have a book recommendation. I feel crushed when I read a book that I didn't like because I don't wanna I don't put up a book that I didn't like.

Tessa Fontaine (44:27)

Mm-hmm.

Hannah Cole (44:28)

I don't wanna do that to an author. They will speak to someone else. It's just not me. but anyway.

Tessa Fontaine (44:32)

Yeah, yeah. Yeah, I'm with you.

Yeah.

Hannah Cole (44:35)

So I do talk

about books too to my newsletter.

Tessa Fontaine (44:38)

Great.

Hannah Cole (44:40)

but I love it because then people write me back and they're like, have you read this one? I'm like, and so I get to talk books with anybody who hits the hits reply in my newsletter. I'm talking books.

Tessa Fontaine (44:48)

Yes, yes.

Hannah Cole (44:50)

this is like secretly scratching the edge. so this is sort of a maybe a hard question, but do you have a why? Like a why

With why you write.

Tessa Fontaine (45:02)

Yeah, totally, totally.

Hannah Cole (45:03)

Okay. Can we share?

Tessa Fontaine (45:06)

I f from my eart from the time I was really, really little, like as early as I can remember, I have found it difficult to articulate what I think and what I feel. And like in this context where we're we're you know, we're talking here, like I I don't mean to say that I don't think I can like form a sentence or talk to you, but I find

Having emotional conversations extraordinarily difficult. I just I like nothing for me is externally processed. Everything is really deeply internally processed. And it turns out I figured out really, really early that the way that I can make sense of anything the the best is by writing it out. So something about it's not just that I think about it, but something about having to

put words to the scramble of feelings and thoughts inside me and to articulate them on the page, it helps me understand humans, situations, the world in a such a fundamentally deeper and better way. And like I understood it in this like, you know, being young and like having a lot of traumatic stuff happen. I understood it in this way that like I did it when I was young to be like, I think I need a right to like survive childhood.

And then it turns out that that has just been maybe what I always have to do. Like I have to write to f to make sense of anything that's going on. And so it feels so deeply merged to be with how to like be okay in the world, like how to put all of the things that happen into some

sort of coherence and I don't even mean to like make it into I don't mean like that I make it into a clean story, but like in some way that I that it becomes it becomes a story and so it becomes something I can hold on to. Or or I'm able to get past the first layers of how I was thinking about something and get to something that actually something else that feels truer. there there is a there's a Joan Didion quote from one of her essays where she says, I write

entirely to figure out what I'm thinking. And so that's what it feels like to me. It's like

Hannah Cole (47:22)

Mm.

Tessa Fontaine (47:23)

I don't think I would know my own mind or how to navigate the world without like figuring it out on paper. And the the it's it feels so lucky to me to have found that. It also sometimes feels incredibly vulnerable because, you know, it's this thing that I have such deep attachment to and

feel the need for. And I have been extremely lucky that that has intersected with like a professional life. And also it's really weird to have like, I'm like, here, here's this book that's just me like, you know, surviving surviving life and making sense of these things. And then it's a commercial property that is, you know, then it then then everyone is like, great, let me tell you how much I hate it on Amazon because it arrived with a

ripped book cover, one star, you know, and you're like, but but or whatever it is. And it it's okay. Like I understand this is the nature of putting, you know, anything that you make out into the world. And also

Hannah Cole (48:23)

No.

Tessa Fontaine (48:24)

it is just so it's so inherently vulnerable at the same time, you know.

Hannah Cole (48:30)

I guess. I'm sorry. I'm so sorry

Tessa Fontaine (48:32)

You don't. You know.

Hannah Cole (48:34)

for that one star review. I get it. I get it. yeah.

Tessa Fontaine (48:36)

Yeah, yeah. I mean, you know.

Hannah Cole (48:40)

I mean the internet is the worst kind of place to be vulnerable. Writing was already vulnerable. Ugh.

Tessa Fontaine (48:45)

Yeah, yeah, that's right. That's so real.

Hannah Cole (48:49)

so I'm curious if we could shift gears a little bit. though I could talk all day about this part. I'm curious from you just

I maybe like you were talking about sharing honestly with this like writers group that you have and just kind of as a baseline and a little as a compare-contrast because I'm also speaking with a nonfiction author this month on the podcast. So it could you kind of paint what it looks like a writer's career? Like you are one writer and it's lovely to hear how you do it, but also like what's the range? How how do people who are your clients, people who are

Teach with you in your writers' group how how do people kind of put it together and make it work? Like what does a writer's life look like? What's the range?

Tessa Fontaine (49:36)

Are you the financially or in terms of of their jobs

Hannah Cole (49:39)

Well

Tessa Fontaine (49:40)

or what?

Hannah Cole (49:41)

I mean I do mean financially, but I mean a little more career wise. Like are they teaching at a university, teaching in an MFA program? Are they writing for a journal? Are they like I mean of course there are these

Tessa Fontaine (49:54)

Yeah, okay.

Hannah Cole (49:55)

people who write for the New Yorker who are like the best writers on the planet and everybody buys their

Tessa Fontaine (50:00)

Mm-hmm. Mm-hmm.

Hannah Cole (50:01)

book and I I bet it's nice to be in that position. But like what are what are what are other writers doing?

Tessa Fontaine (50:08)

Yeah. Yeah. I mean the range is extensive. So a lot of writers in that I know are also teaching and the teaching comes in many forms. So some folks are in academia, like you know, teaching at universities. some folks are teaching in there are lots of like literary organizations, literary nonprofits that are offering classes all the time. So some folks are teaching

in places like that. some folks are working regular human jobs. Like like there's this there's this like horror, literary horror writer named Paul Tremblay, who has had I mean, he might be a great case study because I bet he has

Hannah Cole (50:50)

Okay.

Tessa Fontaine (50:51)

had maybe eight books. he's published a lot of books. And

Hannah Cole (50:56)

Yeah.

Tessa Fontaine (50:56)

he's not like, you know, he's not selling books like Stephen King, but he's like a

well respected, well selling r horror writer. And

Hannah Cole (51:03)

Mm-hmm.

Tessa Fontaine (51:04)

and he has been a high school physics teacher all of this time. And and just now, this like last month, he announced that he was gonna step back from teaching physics. And he's yeah, like I think maybe eight books in.

Hannah Cole (51:19)

No.

Tessa Fontaine (51:20)

and so, you know, so there are lots of people who are just working

work and jobs and you know something like being a teacher, it gives you these big chunks of time off when you're not teaching. And so that can be a really great balance for, you know, having sort of more space to write. in in terms of my clients, like the people I'm working with in the accountability workshop, it really ranges. There there are a lot of people who are kind of working full-time regular jobs. There are also a lot of people who do sort of freelance stuff, a lot of people who do like

communications or marketing or publicity or somehow are in kind of like a writing adjacent field. So they're they're like doing some copy. They're writing

Hannah Cole (52:04)

Mm-hmm.

Tessa Fontaine (52:05)

copy as part of their job, but but not like sort of cr creative writing if you are.

I'll be I feel worried for it, like it's actively happening now that like someone came on a couple weeks ago and is like, well, my job is gone to AI and I don't know how to find any other job. So I, you know what I think some of those jobs are in tricky places with AI now. same with friends of mine who are in journalism, the same thing has been happening to them. Not necessarily because of AI, but just with all of the papers and magazines closing, journals closing and stuff. So

Yeah, it's it's a it I think it's a really wide range. I think like as I mentioned before, I don't know many people who are only writing books. I know a couple, like I know Curtis Sittenfeld and she is only writing books, like Huzzah for her and you know, Queen as she should be. She's doing great. but but like yeah, it most people are are doing a lot of stuff.

Hannah Cole (52:58)

Yeah. Yeah. It's hard. It's hard to do that. Man, throw a kid on top. It's crazy. my gosh.

Tessa Fontaine (53:03)

Whew, yeah, yeah. I know it's a it's a busy life. Yeah. I'm ready for a vacation, I'll tell you what.

Hannah Cole (53:12)

Amazing. so I guess this kind of dovetails with that, but like do you feel like there's something that people misunderstand about the financial side of being a writer?

Tessa Fontaine (53:25)

Yes, I think so. I mean and this kind of I actually kind of from both directions. I know a lot of people who sometimes I'll work with who when they're first getting into writing, they'll be like brand new writers really excited about their novel idea and sort of have this idea that like once they finish the book, they'll be able to publish it and a lot of money will be attached to that process. And

It's it's a possibility, it's always a possibility. But you know, it's like i it's it's a really hard it's a really hard road. And I think it's like, you know, it's kind of like if someone had j was a brand new painter and were like, Well, paintings can sell for a lot of money. All I have to do is make this one great painting and I'll just sell it for a million dollars and it's like I that'll be great. What's the big deal? So it's it's like I there's and it's a hard conversation to have 'cause like of course the stories exist of people who are

kind of new writers and write one book and sell you know and make a lot of money. But

Hannah Cole (54:26)

Yeah.

Tessa Fontaine (54:26)

it that is not the common story. That is not what happens most of the time. And so I think like helping people find the joy and the sort of excitement and the passion for the writing itself and like having that be the thing that drives the engine, drives the boat, as opposed to the like kind of fantasy of the payday.

Because that is out of our control. It is unknowable. so that I think that from the starting point. On the flip side, I know so many people who who I think because of the range I was talking about from sort of like self-publishing to where there's no where, you know, you're not making any money, you're paying some money, to like sort of making a lot of money.

There's such a range and and this isn't part of polite conversation. So we don't talk about, you know, when I tell people I'm a writer, I'm not like, I'm a writer at this level, making this amount of money, right? Like it's not, it's not something I'm saying. So there's also a lot of people, most people in my life, I don't actually think I don't think that they think I make any money from writing. like my family, when I was first getting divorced, was like, You're gonna be destitute. You've what are you gonna do without a husband? And

It like, I have made more money than my spouse for every second we've known each other. Like what d did you not think this was like a biz I so what? Very confusing. And you know, we can read all sorts of other things into there, but but I think there's like I mean, I think it's it's both like it's just a it's a it's a career, it's an art form that has such a r like anything, right? Like musicians, like painters, it just has such a range attached to it.

and it is not something to do because you're like, I would love to just make a bunch of money quickly. Like, let me write a book. It's definitely not that. But it's also not something that like all of us are doing. I mean, many of us are doing it just because we love it. And fuck yeah, excuse me. But like, also some people do make money. So I don't know. It's like you know, it both is and isn't part of the sort of working world and

Yeah, it's it's so nuanced.

Hannah Cole (56:42)

So so nuanced, yeah. And I I was thinking about the there's a art supply company called Daniel Smith. I don't even know if they're still in business, but their motto was Vita Brevis Ars Longa, which means life is short, art is long. And

Tessa Fontaine (56:56)

Mm.

Hannah Cole (56:57)

I think about that all the time. It is one of my favorites because that like my my why feels like that. It feels so much more like connected to like rooting down into the like

fundamental building blocks of being a human.

Tessa Fontaine (57:13)

Mm.

Hannah Cole (57:14)

and like sharing with other humans in these like sometimes what you need it for and the purpose of art is actually for these horrible, difficult moments. Sometimes they're for a great party also, like doesn't have to be sad.

Tessa Fontaine (57:28)

Mm-hmm.

Hannah Cole (57:31)

Curtis Sittenfeld's Romantic Comedy was an awesome, super fun, just gratifying book, right?

Tessa Fontaine (57:37)

Yeah, yeah.

Hannah Cole (57:39)

But there's war and peace too. and I feel like I I have tried to explain to people because we live in a town, you know, in Asheville, it is the the artist model here looks very different from the one that I was trained up in in my MFA program and in New York City, which is

Tessa Fontaine (57:54)

Mm-hmm.

Hannah Cole (57:54)

that, you know, artists here open their doors to

tourists and so people are more familiar with the artists who are working here and like even what that looks like and what their studio means because they open their doors. but also the art you make when you're selling to somebody who's stepping into your studio for the first time and making a quick decision that's worth the money for them to buy that art, it's gonna be a lower price point. It's gonna be a much more accessible subject matter. I say with no judgment, like wonderful. Make your living

Tessa Fontaine (58:21)

Yeah. Yeah, yeah, yeah.

Hannah Cole (58:25)

that way.

Hell yeah. but I'm I'm from and I not because I think it's better, it just happens to be the school I went to, but it I feel like this one that's about like trying to live forever. Trying to like climb

Tessa Fontaine (58:40)

Mm. Yeah.

Hannah Cole (58:44)

Mount Olympus and see if like I can shout loud enough from the rooftops with a painting that is that profoundly moving to someone that

Tessa Fontaine (58:52)

Mm.

Hannah Cole (58:52)

When I'm dead it's still living, you know.

Tessa Fontaine (58:55)

Mm-hmm,

mm-hmm. Mm. What a beautiful way to say that.

Hannah Cole (58:58)

Yeah. I mean, I think I think novels do that too. I think it's why writing speaks to me so particularly. it's like the everyday you know, you have to get to a museum. You have to get to a place to see art as I it's much less accessible. But a book is the art that you can see every day. And I do.

Tessa Fontaine (59:15)

It's true. It's true. It's so fun.

Hannah Cole (59:20)

Yeah, it's awesome. Well Tessa, it's just been

Just a personal joy for me to talk to you. Thank you so much and thank you for sharing about like your world, your work. It's awesome. I definitely

Tessa Fontaine (59:31)

Mm.

Hannah Cole (59:32)

encourage everybody to go pick up your novel, The Red Grove, and also your memoir, The Electric Woman. but can you just tell everybody where they can find you?

Tessa Fontaine (59:43)

Yeah, yeah. And Hannah, thank you so much. This is really such an honor to get to talk to you. and sort of I don't know, I think I I always have really interesting conversations with you about about this very thing, like how we figure out how to be artists in a world and both s you know, hold true in our heart what we want to do and also survive as humans who have to feed their children. So I appreciate that holding that space. yes, you I have a website, Tessafontaine.com.

I am on Instagram, the accountability workshops that I was mentioning also on Instagram and we have a website and so is the camp. It's all all there. All there.

Hannah Cole (1:00:20)

I

love it. I love it. I'm coming to that camp one of these years. I have a novel in me

Tessa Fontaine (1:00:23)

Yes, please, yes, please.

Hannah Cole (1:00:27)

and we're gonna talk when I start to write it.

Tessa Fontaine (1:00:29)

I cannot

wait. That'll be the best.

Hannah Cole (1:00:32)

Awesome. Well thanks

for joining us. Thank you for sharing you. It's been delightful. Awesome. All right.

Tessa Fontaine (1:00:36)

Yeah, my pleasure. Okay.

Bye.

Professor Ray Madoff on How to Tax the Rich

Listen and Subscribe Here

“Somebody who is self-employed and earned sixty thousand dollars will pay about thirteen thousand dollars in income taxes and payroll taxes.”

— Professor Ray Madoff

Why do billionaires often pay lower tax rates than working Americans? In this episode of the Sunlight Tax Podcast, I sit down with tax policy expert and professor, Ray Madoff, to explore how income, wealth, and inheritance are taxed in the United States, and why the current system often favors the ultra-wealthy.

We discuss wealth inequality, estate taxes, billionaire tax strategies, and the most promising proposals for tax reform. If you've ever wondered how the tax code shapes who builds wealth in America, this conversation offers a clear and accessible look at what a fairer tax system could look like.

“Let’s say that you’re Mark Zuckerberg. What he has is a growth in value of his stock. And even though that growth in value of his stock has made him very, very rich, it is not treated as taxable income.”

— Professor Ray Madoff

Also mentioned in today’s episode:

02:30 Background on Professor Ray Madoff and her work

05:40 How the tax system favors the wealthy

07:19 The impact of growth in stock value and tax treatment

09:02 Living off wealth, not income

10:04 Inheritance, gifts, and the lack of taxation

12:15 The estate tax and loopholes

16:20 Public perception and fairness in the tax system

17:21 How the wealthy avoid taxes: borrowing against assets

23:02 Political feasibility of tax reforms

25:46 Wealth taxes and their challenges

29:56 Legal and constitutional issues with wealth taxes

31:46 Potential benefits of well-designed tax policies

If you enjoyed this episode, please rate, review and share it! Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.

About Professor Ray D. Madoff:

Ray D. Madoff is a professor at Boston College Law School and the cofounder and director of the Boston College Forum on Philanthropy and the Public Good. She is the author of Immortality and the Law: The Rising Power of the American Dead and lead author of The Practical Guide to Estate Planning. Her writing has appeared in The New York Times, The Wall Street Journal,  The Washington Post, and The New York Review of Books, among other outlets.

Episode Links:

Professor Ray Madoff’s Book: The Second Estate: How the Tax Code Made an American Aristocracy

My FAQ page on how to Tax the Rich

Get my Tax Help on Substack

Get your FREE visual guide to tax deductions

Order my book: Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed

Watch YouTube video version

Transcript:

Hannah Cole (00:07)

Hello, beautiful. I am so excited to bring you a guest I have really wanted to get on to the Sunlight Tax podcast ever since I read her incredibly readable, incredibly educational book, The Second Estate: How the Tax Code Made an American Aristocracy. So today on the podcast, I am here with Dr. Ray Madoff. She's a professor at Boston College Law School, where she teaches and writes in tax law and policy.

Wills and Trusts Law and Estate Planning. She is co-founder and director of the Boston College Law School Forum on Philanthropy and the Public Good, a nonpartisan think tank that convenes scholars and practitioners to explore questions regarding whether the rules governing the charitable sector best serve the public good.

Hannah Cole (00:55)

Professor Madoff, thank you so much for joining me on the Sunlight Tax podcast.

Ray Madoff (00:59)

Thank you for having me. It's very fun to be here.

Hannah Cole (01:02)

so I'm a tax educator, but I come at it from the practitioner side, kind of boots on the ground with really most of my expertise developed around my clients who are decidedly not the 1%. And so when it comes to higher level things and policy and where, you know, our taxes as self-employed people primarily kind of

Ray Madoff (01:23)

Rosal.

Hannah Cole (01:24)

in to the larger system, I need help. And that's why I was so excited to talk to you.

Your book is outstanding. I hope everyone listening gets a copy of The Second Estate. It is fantastic.

Ray Madoff (01:38)

Thank you so much.

Hannah Cole (01:40)

my gosh. So can you start us off by just giving us a little background on a big question that I think is confusing for people is income versus wealth.

Ray Madoff (01:51)

Sure. so the question is it's sort of it's interesting. Income is the thing that you know, we get from our jobs and we get it from a lot of different places, but it's basically about the flow of money that somebody acquires. And wealth is more of a static number. It's how much how much do you own? So

Hannah Cole (02:14)

Mm-hmm.

Ray Madoff (02:14)

income is what are you taking in and how much do you own?

The reason it's little bit complicated in the tax world is that the word income in income taxes, the definition of income,

Hannah Cole (02:27)

Mm-hmm.

Ray Madoff (02:27)

excludes lots of income that ends up being the income of the wealthiest Americans.

Hannah Cole (02:33)

So you just touched something that really unlocked, think, for me, what I think is going to be the core of.

the learning from your book for people, which is what counts as income is a key to who we actually tax and who pays the most tax. And I think when I'm giving workshops about how self-employed people's taxes work, I'll write the rates on the board, 0 to 37%. And 37%, that looks kind of high. And then you add self-employment tax to that.

it looks even

Ray Madoff (03:07)

Yeah.

Hannah Cole (03:08)

higher. And so people are thinking, well, I guess the wealthy really actually pay quite a high tax rate. So could you kind of share with us, Professor Madoff, like why that is not quite how it works?

Ray Madoff (03:21)

Exactly. So first of all, your clients are right. They are the ones that are self-employed people are hit the heaviest with taxes. So they have income taxes, as you said, up to 37%. And on top of that, they have payroll taxes that are at about 15.3%. And those payroll taxes start right away at the first dollar earned. Unlike income taxes, which have pretty large exemptions.

In addition, payroll taxes can't be offset by things like charitable giving or other deductions. It's a so we call those the hidden taxes because people don't really they haven't really been educated about them. They're very surprised that they have them. They're kind of hidden. And even for employees of somebody else, people who aren't self employed, they are in some ways doubly hidden because they show up not as taxes on your

pay stub, but as these sort of funny FICA and FUTA and they're called contributions. They make it seem like people are saving for their own retirement, but this is actually money that is currently being used to pay for the Social Security and health care of current retirees. And so it is a tax just like any other tax, but it it's kind of hidden from the public. So

so people so somebody who is self employed and earned sixty thousand dollars will pay about thirteen thousand dollars in income taxes and payroll taxes. That's just to the federal government. That's a lot of money for somebody who's trying to get by on sixty thousand and then they pay state taxes on top of that. So

Hannah Cole (05:01)

for sure.

Ray Madoff (05:02)

now to answer your question, let's move over to other Americans, not people who work either for themselves or for others, but people who have

wealth and they've acquired it either through their investments, their investments have gone up in value, or through their inheritances. And here the tax system is very, very different. so for people who have, let's say that you're Mark Zuckerberg, right, who was many times over now centi billionaire, right? He's got the probably more than two hundred billion dollars.

But all of his wealth has not come from salaries, right? He's just a dollar a year guy, so he doesn't pay very much in income taxes or payroll taxes. What he has is a growth in value of his stock. And even though that growth in value of his stock has made him very, very rich, it is not treated as taxable income because we have a rule that gains.

are only subject to tax when they are sold. You have to sell the property and somebody like Mark Zuckerberg doesn't have to sell the property. He can simply borrow against his property and not sell it and therefore not have any taxable income.

Hannah Cole (06:23)

Amazing. Yeah, I think just to underline in case someone was listening and kind of missed the quick hit of that, he isn't paying based on earning, right? We who listening, you, me, everybody listening, we earn the money that we live on. Mark Zuckerberg is doing this other thing and living off the growth of his wealth, right? Yeah.

Ray Madoff (06:43)

Yes. And arguably

it is an earnings, right? But we don't in the tax code we treat it as a nothing until it's actually sold. As if

Hannah Cole (06:51)

Mm-hmm. Yeah.

Ray Madoff (06:54)

as if his life is the exact same as somebody who has nothing because financially, right? Because

Hannah Cole (07:01)

this.

Ray Madoff (07:02)

he because he hasn't sold it. And that's

Hannah Cole (07:04)

Yeah.

Ray Madoff (07:04)

a kind of a weird thing. It gets even weirder when we look at the income tax of inheritance or

Hannah Cole (07:11)

Yeah.

Ray Madoff (07:11)

somebody who

gets money from either a gift or an inheritance or a life insurance policy. If you were given ten million dollars

Hannah Cole (07:21)

...

Ray Madoff (07:22)

you're treated as if you have nothing. You don't have to tell anybody, you don't have to report it. it's just yours. It's your own private thing that somebody gave you ten million dollars. On the other hand, if you and I were to enter into a barter exchange, right? You were to make you know many fantastic silkscreen bags for me and I was to make sourdough bread for you

We would

Hannah Cole (07:48)

Okay.

Ray Madoff (07:48)

each be required to pay income taxes on the value of what we had received for our services.

Hannah Cole (07:57)

Yes.

Ray Madoff (07:57)

We'd have to we'd have to tally and report it to the government. But yet if we're handed ten million, that's just for you to know, private.

Hannah Cole (08:05)

Just unbelievable to me. I have to teach people this and sometimes

Ray Madoff (08:09)

Yeah.

Hannah Cole (08:10)

the example that I give, and it's frankly kind of ridiculous and I feel bad saying that this is how it works, but like a musician, and I've known many who basically like play session music in an Irish pub, like there's one in Boston that I used to go to all the time, the Burren in Somerville.

Ray Madoff (08:26)

Yeah, of course.

Hannah Cole (08:27)

And I was friends with a lot of the musicians there who would basically just pay for pints, right? So

Ray Madoff (08:32)

Right. Yeah.

Hannah Cole (08:33)

those...

Heinz, that beer that they're drinking all night, that's their only pay. That is a pretty meager living for very accomplished

Ray Madoff (08:40)

Yeah.

Hannah Cole (08:40)

musicians. And yet it is taxable income, the value.

Ray Madoff (08:44)

It was taxable, even the beers were taxable.

Hannah Cole (08:46)

Well, what I'm saying is that is a barter exchange. So technically, the tax code, that is barter. Yeah.

Ray Madoff (08:49)

Yeah. Right. Of course. Yeah. That's what it's all taxable to them. That's right. Yeah.

Hannah Cole (08:55)

So yeah, to

a point of ridiculousness, when you compare that to your example, if that's shocking. if somebody gives you $10

Ray Madoff (08:59)

Yes. Yeah. You find ten

you find a hundred bucks on the street, you're supposed to report it to the IRS, but somebody hands you ten million. Well that's your business. Now for the the non-taxation of gifts and inheritances and things like that, the theory

The reason that that exclusion was originally provided was on the assumption that we have an estate tax. An estate tax is a whole separate tax system that was supposed to apply to the richest 1% of Americans. Right now it imposes a tax at a flat 40% rate on all transfers in excess of a pretty big exemption, $15 million. So our $10 million gift wouldn't be captured by it.

Here's the thing about the estate tax. The estate tax so it looks like we have a system that's gonna do some pretty serious damage, right? If all of our rich people paid a 40% tax on everything that they owned when they died or that they gave away, that'd be a lot of money. But the problem

Hannah Cole (10:04)

Agreed.

Ray Madoff (10:05)

is that it has been 36 years since Congress has closed a single loophole in the estate tax. 1990 was the last time. And that's because

The estate tax was really essentially killed through a campaign that was funded by eighteen of the country's richest families. And many of your listeners might know the phrase death tax and a double tax that hurts family farms and businesses, right? There was this very powerful campaign that really turned the public against the estate tax, making them think it was unfair.

Because of course people didn't know about the lack of income tax. They just know, like, maybe this is a second tax on top of it all. And and because it loopholes haven't been closed, the estate tax raise is essentially nothing. And it's really just more something that people have to plan around rather than something people have to pay. And the evidence of it is in the fact that the

the estate tax, so estate tax supposed to apply to the richest one percent. Right now that group owns fifty-five trillion dollars. Fifty-five trillion dollars. This is a time when the total revenue the government takes in in 2025 was five trillion. And the wealth of the richest one percent was fifty-five trillion. Okay. How much estate and gift taxes did that one percent pay? Twenty-eight billion dollars.

nothing. Absolutely. Or point

Hannah Cole (11:37)

So that's moving that.

Ray Madoff (11:40)

zero six percent. Sorry, point zero six percent, yeah.

Hannah Cole (11:43)

Moving that decimal point from 40 % way, way down to under way under 1%. That's

Ray Madoff (11:47)

Yes, exactly. Yeah.

Hannah Cole (11:50)

shocking.

Ray Madoff (11:51)

Yeah. And so in and the reason that we know that the estate tax doesn't impose any harm on people, is that if in case you need any further inf reason than that number, but is the fact that when Trump had it in his full command to enact whatever tax rules he could, right, in the his most recent tax bill,

The Republicans had consistently been running on that we have to repeal the death tax because it's so immoral. He had the chance to do it and he didn't bother. And it's

Hannah Cole (12:20)

That's it.

Ray Madoff (12:21)

because he they know that it provides more cover for the rich because it allows for this very unfair income tax system that otherwise wouldn't withstand scrutiny. People would be like, Well, that's crazy. Why can you receive ten million dollars tax free but we have to tax the Burron guy on the on his pints?

Hannah Cole (12:40)

Yep.

Ray Madoff (12:40)

Doesn't make sense.

so I think that's how we kind of have gotten into that situation of not taxing inheritances.

Hannah Cole (12:47)

Man, it's just shocking that inheritances are not taxed. And I was just rereading the early chapters of your book this morning and reminded myself that a third of Americans on the list of 400 richest families are there simply because they inherited the money. That's not even them working ever.

Ray Madoff (13:05)

That's right. That's right.

Hannah Cole (13:08)

Unbelievable. So I think the arc of this conversation that I would really love, because I think

I'm seeing culturally so much of a sense of unfairness that people actually begin to check out and nihilistic, which I actually think is the enemy of progress.

Ray Madoff (13:24)

Yeah, yeah. I totally agree. I think that there is reason for hope.

Hannah Cole (13:30)

Yeah, I do too. So I do want to touch on how the wealthy actually avoid tax because I do think, you know, my company is called Sunlight On Purpose. Let's shine some sunlight on that one.

Then I, and I do have some questions for you because there is a midterm election coming up. A lot of people are proposing wealth taxes. There are

Ray Madoff (13:50)

Mm-hmm.

Hannah Cole (13:50)

some out there that may be better than others. And I would love to kind of land the plane near what you think we should do. So if you wouldn't mind just doing the sketch first. So I just want to warn the listener. not going to go down a black hole of how terrible things are and stay there. We're going to come out.

Ray Madoff (14:09)

No. Yes.

Hannah Cole (14:10)

But could you sketch

Ray Madoff (14:10)

Right.

Hannah Cole (14:11)

for us how the wealthy are avoiding paying taxes?

Ray Madoff (14:14)

Yeah. So basically there's just two main things. It's the so when you think about how most people listening to this podcast probably get their money, is they probably work for it, right? That's how most Americans get their money and they're subject to heavy taxes. People who already have wealth, either they were given it or they have been given stock and they you know they or they have stock in their companies. so they don't pay tax as their property goes up in value.

And if they need to access that property, they can borrow against it instead of selling it. So they can you know, many people are in the business of lending money and they are happy to lend money to very rich people who can provide a lot of security for their borrowing. Right? These things are f these loans are fully secured, nobody's worrying about not getting paid back. And so they

Hannah Cole (15:04)

Right, I'm the banker

and I'm looking at all of Mark Zuckerberg's

Ray Madoff (15:07)

Yeah.

Hannah Cole (15:07)

money. I'm not worried about him defaulting, really.

Ray Madoff (15:09)

Exactly.

And you're you're and you're thrilled to lend the money because you get interest and you know you have to offer them very favorable rates, but still the the loan is very strong. So that's that's your business model. So

Hannah Cole (15:20)

Sounds like easy money. Yeah.

Ray Madoff (15:22)

you want to be lending money and these are the perfect people to lend the money to. And so they don't pay any taxes. we call this buy, borrow, die, right? You you have an asset, it goes up in value, you borrow against it, and then you die.

It for those people who pass the property at debt there's like a little added benefit, which is that all the gains get wiped away.

Hannah Cole (15:45)

Yes, can we talk about that? I want to name it. It's called the step up in basis. But

we hide it behind this accounting term that most people don't know. So yes, will you explain that giveaway, step up in

Ray Madoff (15:55)

Yeah. So let's take our ten

million dollar person. Let's say that what I gave you, you got the ten I gave you ten million dollars of stock. I bought NVIDIA stock, Apple stock, something for very low. Now it's worth ten million dollars. And if I die and give it to you, you are treated as if you had purchased it for ten million dollars. So that ten million dollars of gain, I'm never subject to tax on it.

and you're never subject to tax on it. We sometimes call that the angel of death loophole, the step up and basis. But it it's a very, it's a rule that is, you know not really very fair given the numbers of our system, given the amount that can pass tax free, right? but people shouldn't think that fixing step up and basis will solve the problem.

Because that's just the frosting on the cake. The bigger problem is the fact that people have massive amounts of wealth that they've never paid taxes on and they never have to pay taxes on it. So I think a better rule would be the rule that they have in Canada, which says that whenever you transfer the property, whether by gift or at death, you just tally those gains. That's when you pay the gains. So that the person who had the run-up in value.

is the one who pays the gains, the same as the rest of us pay taxes on our other forms of income. Because so that would be that's one proposal for addressing that particular problem.

Hannah Cole (17:30)

Would that be called

a transfer tax?

Ray Madoff (17:33)

No, it would be called a it would basically be saying that it's a realization event.

Hannah Cole (17:39)

Okay.

Ray Madoff (17:40)

and so it's just saying that you realize gains not just when you sell, but also when you give the property away. Whenever you no longer own the property, that's when you tally those gains. Yeah. Yeah.

Hannah Cole (17:52)

Got it. Okay. Yeah, that sounds really fair. And they do it.

I love hearing that they already have this rule in Canada. It's hard to make

Ray Madoff (18:00)

Yeah. And

Hannah Cole (18:01)

it, but it's impossible.

Ray Madoff (18:02)

and there's also something kind of fun about this rule, which is that it was proposed both by President Obama and by President Richard Nixon. Yeah. It's

Hannah Cole (18:15)

Interesting. Huh.

Ray Madoff (18:16)

a it's really something that's kind of like a basic fairness thing, like why should we never tax those gains when we're taxing the barter exchanges? We're taxing found money on the street.

Right. So we should tax it to that person, we should tax it upon transfer. The other issue is about people who inherit money or receive it by gifts or because lots of this money is some of it is received at death of somebody, but a lot of it is that money is put into trusts. These trusts are huge. The trusts make distributions and basically much of those distributions are received entirely tax free. And why should that be the case?

Why should we say that somebody that is given five million dollars a year from their trust, why should they be treated as the same as somebody who has nothing? It doesn't make sense. So so

Hannah Cole (19:07)

Agreed. Agreed.

Ray Madoff (19:09)

that's what we should do and we and and we should get rid of the estate tax because it's not doing anything. And

Hannah Cole (19:15)

Hm.

Ray Madoff (19:16)

yeah.

Hannah Cole (19:17)

I have a question for you about that. So I agree with you. It is providing cover to the more educated person who even is aware that it is there for tax fairness, or in theory is there for tax fairness. It provides some cover for an unfairness elsewhere in the system. But do you think politically that it would be possible fix the estate tax?

Or is it an easier fight

Ray Madoff (19:43)

No.

Hannah Cole (19:43)

to get rid of it?

Ray Madoff (19:44)

The reason I don't think it's possible to fix the estate tax is that

Hannah Cole (19:48)

Mm-hmm.

Ray Madoff (19:48)

there is a little bit of incoherence built into the estate tax. For somebody who has worked their whole life and has had a lot of taxable income, right? Let's say Paul McCartney, right? He's probably he's very, very rich, right? But he's probably paid a lot of taxes on that money because

It's from, you know, things that are all taxable, I assume, mostly. and the way the estate tax is structured, the way it it is, and so the way it looks to the American public is now you're dead and now we're slapping on an additional tax. It just doesn't it feels weird in that situation, right? To be taxing that person. Now, of course what people don't focus on is who really is.

Getting the economic benefit of it, and that's whoever is receiving this property. But the tax is imposed based on the amount of wealth that the person has, right? As opposed to the amount of wealth that of the people who receive it. An income tax system is a much more coherent system and one that people can understand because now we're not talking about double tax. We're talking about the fact that an entirely different person has been handed.

you know, couple of million dollars. And

Hannah Cole (21:09)

Mm-hmm.

Ray Madoff (21:10)

we should decide how much people should be able to inherit entirely tax free. If we want to have a preference for inheritances, that's fine. I understand that we want people people want to have, you know, they people want to be able to provide for their families. And so it makes sense

Hannah Cole (21:27)

Of course.

Ray Madoff (21:27)

that we can say, fine, we'll have a preference for a certain amount of inherited income, but we should recognize that it's a preference. And then when we say

How much should inherited income be preferenced over income from work? Then we we'll get a different type of number rather than this other discussion about well how much should the second tax be on somebody who's already paid a lot of taxes? Does that make sense?

Hannah Cole (21:51)

Yeah. Yeah, I

feel like in the tax code, you see this a lot. Look over here, not over here. And it kind of falls in that category.

Ray Madoff (21:57)

Yes, exactly. Exactly.

And that's why I think that by simplifying the system, right, and bringing it all into the income tax, then everybody can understand a little better how the system works.

Hannah Cole (22:11)

Yeah, I like it. I like it. And it makes it simple, and it makes it feel fair. So there's a lot of buzz. California has a wealth tax proposal. Everybody's talking wealth taxes. And

Ray Madoff (22:23)

Yeah.

Hannah Cole (22:24)

I think that's the easy kind of go-to phrase that makes you understand what the project is. But there's some issues with the wealth tax. Can you kind of talk about what the issues are, and maybe talk about if you are able?

What do you think of the California wealth tax? What do you think of Mamdani's Pied-a-Terre tax in New York City? And what would work better?

Ray Madoff (22:47)

Right. Okay. So the wealth taxes, we first heard about them from Elizabeth Warren and Bernie Sanders, right? We should have wealth taxes. A wealth tax is a tax on the amount of wealth that a person has. So it in some ways makes a lot of sense, right? Because we have a lot of very, very rich people. Many of them have not have been able to avoid taxes on them. Some people have paid taxes on it, right? But most of them

haven't. So the idea is, well, let's just tax the wealth if that's the problem, that they're able to acquire the wealth tax-free. And the problem is that when you it it's sort of like a lot of answers that like, well this makes sense, like I call these kind of round one answers, you know, it's the one that makes the most sense and let's just do it. They often

When you push them a little further, they often are a little less satisfying. And so the wealth tax has some pretty significant problems. on the state level, the problem is that very it's very, very easy for people to leave states. And so I live in Massachusetts, you know, Massachusetts, New York, California, we've all lost population to Texas, Florida, you know, tax free states. There's competition among the states. So it's very hard.

for states to impose these sort of taxes that are disproportionate to their sister states. It's just a fact that people can easily move out of a state. Not

Hannah Cole (24:19)

Yeah.

Ray Madoff (24:19)

everyone's gonna move, but I think it could still have an effect on decisions of others whether to set up shop there or in another state. You know, we have to I live in Massachusetts, I love Massachusetts, I'm happy to pay Massachusetts taxes. But

I appreciate that not everybody's gonna feel that way. And so we probably lose business to New Hampshire, you know, and so

Hannah Cole (24:42)

Yeah, for sure.

Ray Madoff (24:43)

and so that's a problem for states. Yeah.

Hannah Cole (24:46)

Yeah. You're speaking

to someone who is the product of the Massachusetts public school system, for which I'm very grateful. It's actually who I dedicated my book to, is the taxpayer But I do,

Ray Madoff (24:55)

Wow, that's great. That's wonderful. Yeah.

Hannah Cole (25:00)

as an accountant, someone who's very aware of how my industry profits off of people's lack of education about how their taxes work, I picture such a ballooning mega industry of wealth calculation.

wealth valuation from accountants,

Ray Madoff (25:16)

Well there's another yes.

Hannah Cole (25:18)

know, valuing the amount of wealth you have is quite a heavy burdensome task. That's kind of a lot to ask much harder than meets the eye.

Ray Madoff (25:27)

I totally agree. It's also, I think, going to feel even to the people who aren't subject to it, it's going to feel invasive. Because

Hannah Cole (25:36)

Mm-hmm.

Ray Madoff (25:37)

we are h as a country, we have not been used to doing annual assessments of people's wealth. We do certain things, we assess the value of their homes and their cars, but that's very different than tell us the value of everything that you own. And so it has a type of an intrusive aspect of it. I think

I'm not sure the public is there yet in supporting it. one other thing to note is that on the federal level, we have an even bigger problem, which is that the federal are the constitution has a provision against direct taxes and there's some question about whether wealth taxes would violate this provision. And the Supreme Court had a case in a couple of years ago where they basically said, Yeah, we might very well find this unconstitutional.

They didn't say it in so many words. So I think given the makeup of the current Supreme Court, if we spent all of our political capital to get a wealth tax, it could be a very sad end if a year later the Supreme Court found it unconstitutional and then we had not solved the problem through other means.

Hannah Cole (26:43)

Bingo. I couldn't agree more. And I love your solution, which feels inherently fair to bring income into the income tax system that is currently just given a pass as though it's not income. Yeah.

Ray Madoff (26:55)

Yeah. Right. Exactly.

Hannah Cole (27:00)

I love it. So in a little lightning round, do you have any kind of pros or cons about the California wealth tax, the New York City tax?

Ray Madoff (27:09)

Yeah, so

I mean the Califor you know, look, I'm there's certain things about the California Wealth Tax that I love, which is that I feel that it's educated the public about this issue.

Hannah Cole (27:16)

Mmm.

Ray Madoff (27:17)

And so, you know, I'm I'm a fan of that. And I think that one thing I learned from my book is how good tax reform proposals came about when there was fear by others that worse proposals would take place. So in the time it was like really so when

When socialism was a very big threat in this country in the early part of the twentieth century, and when communism was a very big threat in the nineteen thirties, right? That's what enabled us to get the modern day income tax, estate tax, and then the whole system of Social Security. So, you know, so in some ways I'm all in favor of more aggressive proposals being out there because I think that they increase the likelihood of having more sensible.

practical proposals actually being adopted. So

Hannah Cole (28:08)

Agreed, agreed. I

love it. Any thoughts on the New York City tax?

Ray Madoff (28:13)

the Pied Terre tax?

Hannah Cole (28:15)

Yeah.

Ray Madoff (28:15)

Yeah. Not I mean that's you know, people like to live in New York and so it's a little and it of course it's and it's just housing. Housing is already subject to tax. So you know Right.

Hannah Cole (28:24)

And it's only second houses. It's not primary residences, which.

Ray Madoff (28:28)

Right. So it seems like it's it's fairly well targeted for the thing they're trying to get at, which is people who don't live in the state, so they're generally not paying taxes in the state, but they want to enjoy the benefits of New York City. So

you know, I don't I don't have really strong feelings about it, but it certainly seems like something that's less likely of course it's not gonna raise the revenue of the California wealth tax. So it's a little bit of a s it's a kind of a a small a small bore item, but you know, but it seems like it's could work for something.

Hannah Cole (29:01)

Yeah, I hear you. Yeah, and I like, you said well targeted. And I do want to kind of double click on that term because I do think there's this idea out there that, we're going to do some ham-fisted, really unintelligent tax proposal. And actually, you can make a well-tailored tax law that hits the right people.

Ray Madoff (29:19)

Absolutely. Absolutely.

Hannah Cole (29:21)

We have a capital gains exclusion when you sell your primary residence on purpose because people have to do that. But if you sell a

second home, third home, fourth home, that's when bigger taxes kick in. So you can tailor things. Yeah.

Ray Madoff (29:35)

Right. Absolutely. Yeah.

Hannah Cole (29:38)

I love it so much. So first, I just want to thank you so much, one, for taking the time, Professor Madoff, being with us today. And also just this book, The Second Estate, How the Tax Code Made an American Aerosocracy. You know, I don't have the visual. But I read it twice.

Ray Madoff (29:50)

You have a do you have the book there or you or you're looking at a piece

Hannah Cole (29:56)

I read it twice. It's only five hours And it's so enjoyable.

Ray Madoff (29:56)

He thought wonderful. Yes. It's very short, yeah.

Hannah Cole (30:00)

I think a lot of people are scared of a tax book. So let me just say

Ray Madoff (30:04)

Yeah.

Hannah Cole (30:04)

to the listeners, it's so pleasant, enjoyable, accessible. It explains things. And so it's a great way to get educated. I could not believe in that more. So thank you for your effort on that. I feel like you've really put some great ideas out there into the ether. And now I want people to eat them up.

Ray Madoff (30:23)

Thank you

so much. It's wonderful meeting you and thanks for all the great

Hannah Cole (30:26)

Awesome.

Ray Madoff (30:26)

work you're doing.

Hannah Cole (30:27)

Thank you so much. I really appreciate And keep in touch. Maybe we'll see each other in Boston sometime. All right. Thank you so much. Take care.

Ray Madoff (30:31)

Yes. Wonderful. Okay. Bye bye. Okay.

Yeah.

Hannah Cole (30:37)

I hope you enjoyed that conversation with Professor Madoff as much as I did. I really highly recommend her book, The Second Estate. I read it twice. It's only five hours on audio format and super readable. So highly recommend. And I also want to just point you once again to my Tax the Rich Quick Facts website. So if you want to

Push the needle forward, build a movement with me, with Professor Madoff. go to sunlighttax.com/taxtherich. And I have a bunch of quick facts in case you want to pull out nuggets from today's conversation to talk to your friends about, just to have at the ready some some stats, some knowledge, some quick facts, and some next steps. I have put that all together for you on a website, sunlighttax.com/

taxtherich. Also, while you're there, if you want to sport the message to your friends, as you know, I live in Asheville, North Carolina, and my studio was completely destroyed in all 20 years of work that was inside it during Hurricane Helene. And I am running a small fundraiser selling tote bags that say tax the rich. You can buy one.

For $25, or you can buy five for a hundred dollars and be mega super studio supporter, and that will help me buy the supplies that I lost and get started making art again. I've had a lot of friends buy the five tote bags, and I have seen people on Instagram tagging me as they give the totes away to people on the school board, people at the arcade as a prize for game night.

so it's really exciting to me to start seeing those tote bags out in the world. They're really fun. And I printed them by hand right here in my office at Sunlight Tax. So if you want one of those and you want those tax facts to share with your friends, please share this website with anyone and buy a tote bag if you feel moved to support me rebuilding my studio at sunlighttax.com/taxtherich. Thanks.

Anna Burgess Yang: Why Self-Employment May Be More Secure Than a Traditional Job

Listen and Subscribe Here

“It's stressful to work for an employer and it's stressful to work for yourself. It's just like choose your stress.” – Anna Burgess Yang 

In this episode of the Sunlight Tax Podcast, I sit down with Anna Burgess Yang to discuss her journey from corporate banking to solopreneurship. We explore the skills that helped her make the leap, how she approaches business decisions and financial management, and what it really means to navigate risk as a self-employed business owner. Anna also shares practical insights on freelancing and building a sustainable solo business while having effective financial planning. 

Also mentioned in today’s episode:

00:10 Introduction to Solopreneurship

06:01 Transitioning from Corporate to Freelance

10:25 Common Mistakes Solopreneurs Make

12:26 The Risks of Employment vs. Self-Employment

17:10 Current Economic Landscape for Freelancers

22:20 Navigating Career Pivots

28:04 Financial Management for Solopreneurs

If you enjoyed this episode, please rate, review and share it! Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.

About Anna Burgess Yang:

Anna Burgess Yang is a freelance content marketer and journalist specializing in B2B SaaS and fintech. She is also a solopreneur educator focused on back-end business operations. A former corporate executive, she now writes long-form content for clients. She also maintains her own blog, newsletter, and a tutorials site. Within her content, she teaches other solopreneurs and marketers how to use AI and automation to work more efficiently.

Check Out Anna’s Work:

FREE RESOURCE: Budget Health Check

Anna’s Instagram

Anna’s LinkedIn 

Anna’s YouTube Channel

Episode Links:

Join the Workshop:Save Like a Millionaire: Using Tax-Smart Accounts

Get my Tax Help on Substack

Get your FREE visual guide to tax deductions

Order my book: Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed

Watch YouTube video version

Transcript:

Hannah Cole (00:00)

Anna Burgess Yang, thank you so much for being on the Sunlight Tax Podcast. Welcome.

Anna Burgess Yang (00:05)

Thank you so much for having me.

Hannah Cole (00:07)

I'm super excited to talk to you. I feel like we have a lot in common, but I really wanted to start by just asking you to give the listeners of the Sunlight Tax podcast a little bit of your story. Will you tell us kind of what the journey is that brought you into solopreneurship?

Anna Burgess Yang (00:25)

Sure. and it's not a traditional path or or the place

Hannah Cole (00:28)

Yeah.

Anna Burgess Yang (00:30)

or the place that I really thought I would end up. so

Hannah Cole (00:32)

Yeah.

Anna Burgess Yang (00:33)

I started my career in banking. I actually worked at a bank for six years. and then

right out of college went to work at a financial technology company that worked with banks. So I was still in the space, but working as a technology provider and helping banks and credit unions across the US implement enterprise software. And I stayed at that company for 15 years. So long time.

Hannah Cole (00:59)

Wow.

Anna Burgess Yang (00:59)

Right around or during the pandemic, like many people, I was kind of thinking, what else could I do with my life? and it really wasn't something I had considered up until that point because the company, it was small, it was very had very flexible work. that was it was just a great fit for me that way. But during the pandemic, I really started to just rethink like what do I want to do? Is this is this what I want to be doing? Is this the company I want?

to be at. The answers to all those things were no. I didn't want to do that anymore. And so I started thinking what else can I do? Because I that was my first job out of college. I hadn't done anything else. So I don't know how exactly, but I somehow landed on content marketing that people would actually pay me to write for companies. So I got a job at a marketing agency and quit my tech job.

And so I was writing mostly for other technology companies in kind of a variety of spaces through this agency. I was only at the agency for about eight months. The agency just was not a good fit, and I got a job at a different agency, but in more of an account manager role. So doing different type of work and not writing. And I was at that company for about a year and got laid off. And

At that point, I had been considering going out on my own. Something I'd really never thought about at any point in my life, because with a banking background, I'd always been told that self-employment was risky. But

Hannah Cole (02:33)

Mm.

Anna Burgess Yang (02:34)

at the time that I got laid off, it seemed like full-time employment was risky. in the tech industry in particular, people were getting laid off right and left. And so

I thought I'd I'd started thinking, like, what would this look like if I went out on my own and and did that? And so when I got laid off, I'm like, well, here's the chance. The

Hannah Cole (02:56)

Yeah.

Anna Burgess Yang (02:57)

opportunity has presented itself. The timing wasn't my decision, but I think it was a direction I was headed anyway. So I started

Hannah Cole (03:03)

Mm-hmm.

Anna Burgess Yang (03:04)

my own freelance writing business, writing for technology companies. And on the side, I

Create resources for fellow solopreneurs

because that is something that I'm just very passionate about. I feel like my background coming from company they came from and the the banking experience and things like that give me a really unique perspective on starting a business. I didn't I didn't make some of the same mistakes I think some solopreneurs make just because I had that background. And so I really wanted to kind of

provide education, talk a lot about tools and technology and things to make work easier. So I create resources and host webinars and workshops and things like that for fellow solopreneurs.

Hannah Cole (03:51)

I love it. I really love the way that it does feel like you are helping to kind of lead people through the terrain of solopreneurship. Like this article, gosh, there's so many that I want to ask you about. But I was just reading this article you wrote about skills that you got from working in a corporate environment and how helpful they were in being a solopreneur. And you just reference like the mistakes that you see people make. So

Can you just outline some of those mistakes that you see solopreneurs make or just struggles that people have when they strike out on their own? because I think your kind of experience is really has a lot to bring to

Anna Burgess Yang (04:27)

Yeah. and yeah, and one one thing

one thing in particular that I'll that I'll add to my corporate experience was when I left, I was an executive. So not I wasn't an individual contributor anymore. I was part of the team that was making decisions about the finances of the company, about the strategy of the company. And so one of the things I see solopreneurs struggle with is decision making. Like suddenly you are in charge.

And everything falls on you, which has benefits. You can change direction. You can try something new. You're not stuck in like red tape that often comes with corporate decision making, but also you're assuming all of the risk. And so some things I see solopreneurs struggle with is they're just not comfortable making decisions, so they don't act quickly, or they just take too long, or they don't make it at all because they're afraid. or that they make decisions like kind of

too quickly and then they're constantly shifting and they're not letting like a decision settle and really decide is that the right thing and getting data. They're just they're constantly bouncing between decisions. So that's something I think solopreneurs struggle with a lot. Another one

Hannah Cole (05:39)

Yeah.

Anna Burgess Yang (05:40)

is like investing in your business. And that it's but I what I mean by that is I pay for a lot of tools

that make my work more efficient because I recognize trade-off is more time for me to do higher value work or spend time with my family or take a nap or whatever you know, but but I think a lot of times solopreneurs they're so they they want to keep their money, right? You know, they and so paying for tools seems like they something that seems like a risk or they just don't want to, they want but they don't recognize that that lets them do other things that could bring more money into the business.

and a third thing, which I know you talk a lot about is just being uncomfortable with money.

Hannah Cole (06:19)

Mm-hmm.

Anna Burgess Yang (06:20)

and not knowing how to budget around unpredictable income or not even sure like how to keep track of like income and expenses and some things. If you've never done it before, there's not a good foundation for it. So those are some of

Hannah Cole (06:34)

Yeah.

Anna Burgess Yang (06:34)

the big things that I kind of talk about a lot is, you know, kind of those executive skills, kind of those

operations skills and then financial skills.

Hannah Cole (06:45)

Yeah, I appreciate that a lot. I think both you and I have served some time as a project manager and I feel like

Anna Burgess Yang (06:51)

Yes.

Hannah Cole (06:52)

that's a really useful I've never been an executive, but I I mean except of my own company, but that project management was so difficult and so valuable. Like I really appreciated managing other people timeline and budget and that being so clearly something that I needed to keep careful control of. because man, is it helpful.

When you work for yourself.

Anna Burgess Yang (07:16)

Yes. And I was a a

product manager, which is a lot of project management as part of my job. And so I knew when I started my own business, like the day I had two clients, I'm like, I need to figure out how to project manage more than I need to build a system that can handle more than one thing. And it has to be able to continue

Hannah Cole (07:36)

Wow.

Anna Burgess Yang (07:36)

to grow with me. You know, I can't just wing it anymore with making sure that things are done on time and, you know, keeping track of

multiple client preferences and ways of delivery and all of that. So for sure, project management is a whole big thing that a lot of people, if you've never done it before, it's it's a very kind of foreign concept.

Hannah Cole (07:58)

For sure, for sure. I was just also reading another one of your articles. By the way, I haven't mentioned your sub stack. It's called Work Better. and it's great and anybody who's listening should definitely subscribe to it. but one of the articles like a headline that really grabbed me was the that people don't talk enough about the risks of employment.

Anna Burgess Yang (08:19)

Yes.

Hannah Cole (08:19)

and I just

I found that so interesting. I I mean, I am an artist and I'm not just an artist by training, but also like in my heart and soul. And I think like the strictures of a corporate environment have always graded on me. But it seemed like to me personally, like when studio time was this thing I really preserved fiercely that the timelines of corporate environment, like just a day job,

And it especially as a woman, things like maternity leave and the complete lack of it. w it seemed like the only way I would ever get the kind of leave that I really thought was, you know, fair and good was to have my own company. So would you be willing to just sort of talk a little bit about those the risks as you see them in having a job?

Anna Burgess Yang (09:10)

Yeah, so because

I worked in banking for a long time and I was a mortgage un I was a mortgage underwriter really early and so I was part of

assessing risk in borrowers in banking it is drilled into you that self-employment is inherently risky. And to a bank it is because you can't, you know, you want W-2 income because then you know how much the borrower is earning. And it's hard to tell with self-employment. So that that had always just been part of the framework that I grew up with or that I learned as a young adult was that self-employment is risky because the income is unpredictable.

But when the but the day I got laid off, I lost a hundred percent of my income. I went from salary to zero.

And you know, unemployment in this country is a joke. it was I had it was a a painstaking process to file for unemployment in my state. it was a fraction of what I had been earning. And and as soon as I

got a freelance role that paid me one week, they kicked me off of unemployment. Even though the next week I was back to having zero again. So it was just

Hannah Cole (10:23)

So awesome.

Anna Burgess Yang (10:24)

it was a real you know, it's not built for that type of thing. It's built for you get another job and now you're done with unemployment. So any but that aside, the risk of employment is that you're at the mercy of the employer.

there we have you know at will employment in the almost every part of this country where they can get rid of you for any reason. And so when I lose a client, it's a fraction of my income. It's it still stinks. You know, my clients their budgets change, their needs change, all kinds of things change. And sometimes without a lot of warning

you know, I I may they may just be like that, you know, we're indeed the eng engagement at the end of this month. it's just a f it's just a portion of my income. It's not my whole income. And so that's part of the reason why I prompted that article is because, you know, from my former banking perspective, I was like, well that's the more stable income

is when you only lose maybe twenty percent or some something like that rather than all of it. and you know, with with getting laid off for most people, I mean it it's immediate. There's no notice period. In a vast majority of cases, there's no notice period. And so even providing a two weeks notice, the employer doesn't have to honor that. You I've told people before you have to be prepared that your employer may say, Well we're just gonna be done today.

And that's the it and that's it. You have no recourse and you have no protection. so self-employment to me puts me in more control.

I have to save, you know, to plan for things like f lower client months, but I can choose to do that. And that's just part of how

Hannah Cole (12:04)

Yeah.

Anna Burgess Yang (12:04)

I run my business.

Hannah Cole (12:06)

Yeah, for sure. Whew, yeah. I'm we my husband has worked for startups for his whole career and he just just this year was at a company that closed overnight. Like in the morning everybody had a job and at five PM nobody had a job anymore. The company ended and there was no notice and no severance. I was like, that was scary. we're okay, nobody needs to cry for us, but

Still, it was it was terrifying and I felt really bad for everyone at the company.

so I am curious, like, just because I think that your I don't have a great sense of like what part of the f of the world your clients are operating in, kind of like what their concerns are and stuff, but I I have been just speaking of that like risk of self employment versus employment, is like the job landscape really feels like it is in a lot of flux right now.

and I think that is true if you are an employee and you're just looking at these LinkedIn posts of like massive amounts of layoffs at larger companies. Or if you're self-employed and you're just like your clients are all kind of suffering from work that's drying up from AI replacement as as mine are. so I'm just kind of curious from you, Anna, like

Do you have a sense of like the lay of the land? Like what does it look like from where you stand right now? What are you seeing in the economy based on who you serve?

Anna Burgess Yang (13:30)

so I work mostly with tech companies.

and

Hannah Cole (13:33)

Uh-huh.

Anna Burgess Yang (13:34)

you know, their their work

What they do for their customers, I think, is changing. It hasn't really impacted me and the type of the type of work that I do for them, because I do a lot of like interview-based work. So I talk to people and like write, you know, write up a journalist style article about it and things like that. So there's still, I think, a need for that type of writing. but I I I do kind of wonder, you know, at what point some of the things that are I'm seeing from other people are going to

Trickle down and hit me in some shape or form. A lot of my friends are in similar writing type of roles, but maybe internal at a company. Many of them have been laid off, or their roles have changed substantially as the company itself has pushed employees to use more AI. So they're like, this isn't what I signed up for. And I

a little bit feel like I'm waiting for the other shoe to drop and maybe it's going something's gonna hit me at some point, but so far it hasn't. and which is great. But I

Hannah Cole (14:42)

Yeah.

Anna Burgess Yang (14:43)

it's it's hitting so many people I know in so many ways that are heartbreaking because again if you're working for an employer

it's just you know, the impact is kind of immediate if if something happens to your job and then, you know, some some freelancers I know are struggling to find the type of work that they were doing before.

Hannah Cole (15:05)

Mm-hmm.

Yeah. Yeah, it's interesting. what I have been noticing is it's so individual. Like there are people who are doing fine and the maybe they're in an industry that's relatively untouched and they kind of aren't noticing all of this stuff. And then there's people like me, like my income dropped very dramatically this year, and I have just been like, What's happening? What's going on?

And it's hard to even get the data about it, you know. My brother works in Washington DC at a he worked at a large nongovernmental organization funded by the State Department and you can you can imagine what happened to him six months ago. He he lost his job because of Doge. he was actually personally doxxed by Elon Musk.

Anna Burgess Yang (15:47)

Out more.

Hannah Cole (15:49)

His name and salary tweeted, by Elon Musk. So that that was a little voyage for him. So like yeah, I mean there's like people in government, people in the creative economy, it's just tech workers. It's it's interesting how it's spotty,

Anna Burgess Yang (16:03)

And it puts everyone on edge, I think, because you

Hannah Cole (16:06)

Yes.

Anna Burgess Yang (16:07)

wonder, I one one of my siblings works for a very large tech company that kind of has rolling layoffs and every single time I have to send a text message like, are you okay?

Hannah Cole (16:19)

Wow.

Anna Burgess Yang (16:19)

Because it just kinda and it just kind of keeps everybody scared all the time, wondering if they're gonna be in the next round of cuts, maybe if they made it through this round. And so we're all operating I I actually wrote about this recently too. We're all kind of operating in a culture of fear and like

Hannah Cole (16:39)

Yeah.

Anna Burgess Yang (16:39)

that we can't quite settle, or it's hard to make plans like even in your personal life, because you're worried about what your professional like is your professional.

Hannah Cole (16:54)

Yeah, yeah, I agree. and yet, you know, I do find as especially as a as a business owner, I want to approach the world and my work with a sense of optimism. it's getting harder. It's like actually kind of hard to be optimistic. I think it's not unreasonable and it's absolutely possible, but I'm just noticing that in myself. There is a gloom like around us and a fear. yeah.

Anna Burgess Yang (17:18)

And I I talk to people quite a bit who are maybe considering starting, you know, going out on their own. Maybe they lost their job or they just can't take it anymore. And you know, I'm very upfront about you know, the ups and downs of running a business by yourself. but also try to say like your your current employer is

causing you a lot of stress. It's just a different type of stress. Like it's it's stressful. It's stressful either way. It's stressful to work for an employer and it's stressful to work for yourself. It's just like choose your stress.

Hannah Cole (17:51)

For sure. Yeah. Choose what you want to have control over. Yeah. Yeah, for sure. So I know you have like a download that you offer that's about career pivots, helping to coach people through that. You have certainly been through s a pretty major one yourself. I'm curious if you just have some wisdom to share about pivoting.

Anna Burgess Yang (18:13)

Yeah, the the resource you're referring

to, I kind of break out what are different ways that people end up pivoting. 'Cause I consider that I had several pivots. You know, I pivoted from the industry, you know, there's a cold like I'm gonna just do something completely different and got out of a direct tech job and started writing. there's kind of the boredom, like you feel like you've reached

the top of maybe what you can do at a company. And I think that partially led to me leaving the company that I was at for 15 years was just I there wasn't anywhere else for me to go.

Hannah Cole (18:46)

Yeah.

Anna Burgess Yang (18:48)

you know, there's kind of curi curiosity, like I I just really want to grow and change and just see what I can do. And that's maybe what leads people to self-employment.

and then there's there is a fear based pivot. Like I'm not sure that this job or this type of work is going to be there anymore. And maybe I need to upskill or get into a different field or something

Hannah Cole (19:17)

Mm-hmm.

Anna Burgess Yang (19:18)

before it hits me. And I don't know that we can all predict that and certainly not everybody's in a position to do any of those things and I recognize that as well. Like I had to take

pretty large cut in salary moving from an executive at a tech company to basically the lowest level writer at a content agency.

Hannah Cole (19:37)

Huh.

Anna Burgess Yang (19:37)

and had to plan for that. Like can't is that even feasible? What do I need to earn

Hannah Cole (19:43)

Mm-hmm.

Anna Burgess Yang (19:44)

versus what can I earn in like a year or two, which is much different.

Hannah Cole (19:49)

What an interesting decision making process to go through. Cause I think a lot of people would just take those two data points. What am I earning right now? What will I be earning tomorrow when I start this venture? But you're wise to think it through a year, two years down the line. How did that look different from day one?

Anna Burgess Yang (20:07)

And I told my husband when we when I made that, you know, 'cause we knew what the offer was and what I was going to be making. and then when I went self employed, I said, Give me six months.

Like if I can't not not to replace my salary, but to have enough momentum that this seems possible. But if

Hannah Cole (20:25)

Yeah.

Anna Burgess Yang (20:26)

I hadn't been able to get clients or like that seemed like that it this wasn't gonna work, I would have gone out and found another job. Like, you know, we have a mortgage and we have kids and things like we have things to pay for.

Hannah Cole (20:36)

Yeah.

Anna Burgess Yang (20:36)

but I knew that what I was going I had to I we had enough cushion or we kinda planned enough to kind of float the difference until

Until my earnings got back up to what they were previously. So but you have to think about that math, right? Like w what can you f if you can of if you can afford to take less, how mu how long can you afford to take less?

Hannah Cole (20:58)

Yeah.

Yeah, and I think planning those timelines is really I've been thinking a lot about predicting the future. Partly 'cause the whole world is trying to do it right now with AI and nobody can. And yeah, just like

Okay, well realistically in three months will I have figured out this problem that I'm currently working on. And like, you know, I think the first year you try something, that's really hard math. But once you've kind of been in it, like I have had my company for ten years now, I kind of have a good sense of like how long a project might take me. that's getting easier, I guess, is my point. Yeah.

Anna Burgess Yang (21:35)

Yeah. And I always tell

people also when I talk to them about that math of of changing from corporate to solopreneur is like

Hannah Cole (21:44)

Mm-hmm.

Anna Burgess Yang (21:45)

what you need is not the same as what you're earning today. Like what are your what are the non essential things that you can cut for

a period of time and still be okay to kind of get you

Hannah Cole (21:58)

Yeah.

Anna Burgess Yang (21:58)

through that initial six months period or or however long it might be. And it's not saying cut these things forever. It's saying what could how how much could you scale back? And

Hannah Cole (22:10)

Uh-huh.

Anna Burgess Yang (22:10)

what do you absolutely need to pay for until

Hannah Cole (22:14)

Yeah.

Anna Burgess Yang (22:15)

your business kind of picks up and you find your rhythm and your clients and things like that.

Hannah Cole (22:19)

For sure. Yeah, that is really it's a good exercise to do. I mean, we we have done it as a family in these last few months, just like cut things as much as we can. and it's not at a place where we absolutely need to be doing it, but it actually feels really good to do anyway. to just be like because we've both been having this conversation of

What what is happiness? You know, like we we can't not earn money. That's off the table for us. But we don't have to

Anna Burgess Yang (22:46)

Right. Shoot capitalism.

Hannah Cole (22:50)

Yeah, right. It would be nice. But I feel and I I love I love my work, really, truly I do. Sometimes I just need like a little rest. But, you know, it's to me like it's a dosing problem, you know. I don't wanna have to work so hard that I don't get to sleep or enjoy weekends. But you know, if I

work a reasonable number of hours. I love what I do. So I think it's a really interesting question of like, well, what is actually I find that digging into your budget can actually be a real question, a real discussion about what brings you joy. And that is a really good conversation to have, whether it's, you know, alone

Anna Burgess Yang (23:28)

Yeah.

Hannah Cole (23:29)

w with yourself or with a partner. because man, it's

Funny how much you can kind of autopilot

on your spending and then not really think about, well, is this actually bringing joy and value to my life? Or is like, I don't know, grinding my coffee beans and having a really wonderful coffee at home every day rather than out co totally pleasant.

Anna Burgess Yang (23:52)

Yeah. And I because I've come from, you know, banking background and I worked in that space for so long, both

Hannah Cole (24:00)

Mm-hmm.

Anna Burgess Yang (24:00)

like for my business and for my home life, I basically have three budgets, like a worst case scenario. And then kinda

Hannah Cole (24:06)

Wood. Uh-huh.

Anna Burgess Yang (24:09)

like here we operate all the time and then like well what happens if

I have a really good month in my business. Like what w what might we do with extra money? Do I do something in my business? Do I do we do something as a family? but that way I'm not making decisions

out of like snap decision or an emotional reaction. I'm like, okay,

Hannah Cole (24:28)

Yeah. For sure.

Anna Burgess Yang (24:30)

if I lose a big client and I can't get one I right away, I just move down to the bare minimum, you know, budget and operate on that for a while, but that's already planned out for me. so that it's

Hannah Cole (24:40)

That's really smart.

Anna Burgess Yang (24:42)

yeah, so they just I have this spreadsheet of like low, medium, high, operating on medium all the time, and then could easily move to low or high and just know exactly

Exactly what I need to cut or what I need to change if I'm in that s situation.

Hannah Cole (24:56)

Mm-hmm. That's

great. That's great. I love it. I actually wanna you know, it's it strikes me as I was reading through some of your posts on Substack that you really do feel

comfort in the financial realm. Like you were talking about one of the skills you had in your corporate job was reading a profit and loss statement. And a lot of people that I work with don't know, maybe don't even know what a profit and loss statement is. It's one of the three financial statements that you get from accounting software. the one that tells you how much profit you made.

in a given period. So I'm just curious, where you learned how to do that?

Anna Burgess Yang (25:40)

So some of it came from working at

a bank, even though I was on mortgage, which is on the consumer side, but I often

Hannah Cole (25:48)

Mm-hmm.

Anna Burgess Yang (25:48)

had to look at a borrower's tax return. And so if they were self employed, I was looking at the part of their tax return that was base, you know, income and versus expenses. So I had

Hannah Cole (25:58)

Yeah.

Anna Burgess Yang (25:59)

kind of a baseline understanding of what a self employed person reported on their taxes. And then when I started working for the financial technology company, part of the software was entering a profit and loss

statement. So was the bank taking the tax return from their borrower, plugging the numbers into the product that I was teaching them how to use, and then getting

Hannah Cole (26:22)

Mm-hmm.

Anna Burgess Yang (26:23)

all the numbers. So they were analyzing commercial borrowers, so all business. And so I was I was teaching bankers how to they knew how to analyze. I was teaching them the data entry part to get it into the product so that they could you know look at ratios and things like that. So through that I kind of backwards learned it. Like I knew

how the software worked. The bankers

Hannah Cole (26:45)

Yeah.

Anna Burgess Yang (26:45)

knew how the bankers knew how to teach the profit and loss. And just in conversation with them and in having to teach the product, I learned about balance sheet, profit and loss, different cash flow statements and things like that. and so by the time I went out of my own, you know, I knew I managed my own finances for several years before I finally hired a bookkeeper, but I was comfortable doing it because I'd seen it

hundreds and hundreds of times before.

Hannah Cole (27:14)

Wow. Yeah, that's awesome. It's so good. I mean, it's really powerful. It's like a really great knowledge base to have. so mentioned or you've you've come close to mentioning a few times mortgages and self employment being risky to the bank.

And I just from the opposite side of that equation fits me, somebody who, you know, used to do taxes. I now I teach taxes exclusively, but I used to also do the taxes for self employed people. And there's this really interesting conversation that would really shift the way that people orient towards their taxes and their deductions when they were interested in getting a mortgage.

And it was because of how yes, conservative banks are and that you they're, you know, maybe you just started your business this year, you are not getting a mortgage with only one year of

Anna Burgess Yang (28:06)

Two years.

Hannah Cole (28:07)

Yeah. And it's like much more conservative timelines that you need to show the bank when you're self employed. Like I s I've seen banks that required three years of profit and loss statements. and of

Anna Burgess Yang (28:18)

'cause us usually

they'll want two full years. So nobody starts their business on January first. So you

Hannah Cole (28:24)

There you go. Mm-hmm.

Anna Burgess Yang (28:26)

that's why it ends up usually trickling into three years, because you don't have two full years of returns. So

Hannah Cole (28:33)

Yeah.

There's a real temptation when you're self-employed to more or less get your income reportable, taxable income as low as humanly possible. And of course, we all understand why that temptation is there. You want to pay lower taxes. Life is risky when you're self-employed and you want to, you know, report as little income and pay as little tax as you can. But there is another side there. When you want a mortgage

When you want to draw on your social security and Medicare, you need to have been paying into the system at a higher rate, at a higher level. You need to have been reporting a higher amount of income in order to get a mortgage or a bank loan. And so it is not always the right answer. Sometimes it feels like the right answer is only report maximum expenses, put everything on that Schedule C that you possibly can. And that isn't always the right answer. This is the time where you want to be really cautious and sometimes be like,

you know, you have some leeway in how many expenses you actually report. You don't have to put every expense you had on your tax return. You can report a higher

Anna Burgess Yang (29:40)

Yeah. And I was very

Hannah Cole (29:41)

Thousand.

Anna Burgess Yang (29:42)

lucky. My husband and I had just refinanced our house like a couple of months before I got laid off. So at the time I

Hannah Cole (29:50)

wow.

Anna Burgess Yang (29:51)

was a W two employee and

Hannah Cole (29:53)

Whoa.

Anna Burgess Yang (29:55)

because that was when interest rates were really low. They're not so much anymore, but we really got lucky in that regard 'cause it would have been probably a non starter.

for to put our house on just my husband's income without any real support from me because I we would have had to wait years to be able to show that.

Hannah Cole (30:14)

Yeah.

Man. It's so it's so good to know and it's really like it's not that many people who know three years in advance that they're going to in three years be applying for a mortgage. But it is just good. If we can if Anna and I right now, dear listener, can put that tickle in your brain. It's good to be aware of it.

Anna Burgess Yang (30:35)

Yeah, or if you're thinking about leaving your job and also thinking about refinancing or buying a house, maybe do that before you become self-employed. Because the bank can't do anything once the loan is closed. Like you can do whatever you want, they'll never they don't follow up. you don't have to reprove your income at all ever again until you refinance. So you're fine. You could literally lose your job the next day and the bank won't know.

Hannah Cole (30:59)

Wow, that's kind of incredible, isn't it?

Anna Burgess Yang (31:02)

And it's so different for consumer versus business because part of the reason I saw so many tax returns is businesses have to reprovide income or their profit and loss and all that every year to the bank.

Hannah Cole (31:13)

Mm-hmm.

Anna Burgess Yang (31:14)

it's part of their loan agreement, it's not for consumer for more personal mortgages. You you whatever it is on the day of close, that's it. So unless unless you're financed to

Hannah Cole (31:25)

Wow. That's so interesting.

Anna Burgess Yang (31:27)

buy a different house, you don't have to do it again.

Hannah Cole (31:29)

Wow, that is kind of incredible. Wow, this has been so interesting to me. I I really think there are some juicy things, especially about the financial side of managing your self-employment. And I encourage everyone to go check out Anna's Substack, which really has some great pieces about the journey of self employment and some real skills that you can obtain. Anna, can you tell people where they can find you?

Anna Burgess Yang (31:55)

Yeah, so my Substack, as you mentioned, I'm sure you'll link in the show notes, but that's work better not media. I'm on LinkedIn, Anna Burgess Yang. There's only one of me. So I'm easy to find there. and my website, Annabyang.com, has links to everything. I've got a blog on top of I write kind of an obsessive amount. And so I have a blog, I have a newsletter, I have a Substack, I have a tutorials website, I have a YouTube, like there's a lot.

I produce a lot of content.

Hannah Cole (32:24)

It's amazing. It is really amazing. Wonderful. Well, thank you so much for sharing your wisdom with us here on the Sunlight Tax Podcast. It's a pleasure to have you.

Anna Burgess Yang (32:32)

Yeah. Great to chat with you.

Hannah Cole (32:34)

Bye.