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Hannah Cole 1/27/26 Hannah Cole 1/27/26

1099 Problems (and How to Avoid Them)

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In this episode of the Sunlight Tax Podcast, I explain what 1099 forms are, why accurate 1099 reporting matters, and how mistakes can impact your taxes if you’re self-employed. I break down common 1099 problems and how to avoid them. I also share what to do when a 1099 is wrong and how to make sure all your income is properly reported to the IRS. We also cover key 1099 deadlines and practical bookkeeping tips to help freelancers, contractors, and small business owners stay compliant and avoid costly surprises at tax time.

Listen and Subscribe Here

In this episode of the Sunlight Tax Podcast, I explain what 1099 forms are, why accurate 1099 reporting matters, and how mistakes can impact your taxes if you’re self-employed. I break down common 1099 problems and how to avoid them. I also share what to do when a 1099 is wrong and how to make sure all your income is properly reported to the IRS. We also cover key 1099 deadlines and practical bookkeeping tips to help freelancers, contractors, and small business owners stay compliant and avoid costly surprises at tax time.

Also mentioned in today’s episode:

01:12 Understanding 1099s: An Introduction

03:21 The Importance of Accurate Reporting

06:25 Common 1099 Problems and Solutions

08:57 Tallying Your Income Effectively

12:03 Some Tips for 1099 Management

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.

Links:

Join my free class on 1/27 at noon EST: Make Taxes Easier and Stash an Extra $152k in Your Savings

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

Watch YouTube video version.

Hannah Cole 1/20/26 Hannah Cole 1/20/26

What’s New for Your Taxes This Year: Key Tax Changes You Need to Know

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In this episode of the Sunlight Tax Podcast, I break down the most important 2025 tax law changes in clear, jargon-free language. I explain the new Schedule 1-A and its temporary deductions, including no tax on tips, overtime, car loan interest, and enhanced senior deductions, plus what the latest tax bill really means for your wallet.

You’ll also learn about “Trump accounts” for children born 2025–2028, updated 1099 reporting rules, retirement catch-up contribution changes, and the higher standard deduction. This practical episode helps you understand key tax changes, which tax benefits apply to you, and how to avoid missing important deductions this tax season.

Listen and Subscribe Here

In this episode of the Sunlight Tax Podcast, I break down the most important 2025 tax law changes in clear, jargon-free language. I explain the new Schedule 1-A and its temporary deductions, including no tax on tips, overtime, car loan interest, and enhanced senior deductions, plus what the latest tax bill really means for your wallet.

You’ll also learn about “Trump accounts” for children born 2025–2028, updated 1099 reporting rules, retirement catch-up contribution changes, and the higher standard deduction. This practical episode helps you understand key tax changes, which tax benefits apply to you, and how to avoid missing important deductions this tax season.

Also mentioned in today’s episode:

03:39 New Tax Forms and Deductions

06:44 Understanding the Schedule 1A

10:31 Trump Accounts: A New Initiative

13:14 Changes in 1099 Forms and Reporting

15:52 Updates on Standard Deductions and Child Tax Credit

18:47 Join my Upcoming Free Class

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.

Links:

Join my free class on 1/27: Make Taxes Easier and Stash an Extra $152k in Your Savings

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

Get my 1-hour course: All About 1099s

Hannah Cole 1/13/26 Hannah Cole 1/13/26

It’s 1099 Time: Here’s Your Checklist for Stress-Free Filing

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In this episode of the Sunlight Tax Podcast, I break down everything self-employed business owners need to know about 1099s – what they are, why they matter, and what’s changed under current 1099 reporting rules. If you work with independent contractors, I walk you through a clear, step-by-step 1099 checklist to help you file correctly and on time. We cover why accurate bookkeeping is important, when and why to collect W-9 forms, and how to avoid common 1099 mistakes that can trigger IRS penalties.

I also explain the different types of 1099 forms (including which ones apply to freelancers and small businesses), what each form is used for, and the penalties for failing to file or filing incorrectly.

Listen and Subscribe Here

In this episode of the Sunlight Tax Podcast, I break down everything self-employed business owners need to know about 1099s – what they are, why they matter, and what’s changed under current 1099 reporting rules. If you work with independent contractors, I walk you through a clear, step-by-step 1099 checklist to help you file correctly and on time. We cover why accurate bookkeeping is important, when and why to collect W-9 forms, and how to avoid common 1099 mistakes that can trigger IRS penalties.

I also explain the different types of 1099 forms (including which ones apply to freelancers and small businesses), what each form is used for, and the penalties for failing to file or filing incorrectly.

Also mentioned in today’s episode:

01:00 Understanding 1099: The Basics

04:31 The Importance of 1099s

10:53 The kinds of 1099s you are going to be dealing with

18:20 Checklist for Issuing 1099s

25:45 Other Resources for filing 1099s

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.

Links:

Join my free class: Make Taxes Easier and Stash an Extra $152k in Your Savings

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

Get your free January Checklist

Hannah Cole 1/6/26 Hannah Cole 1/6/26

January Tax Setup: Make Your Taxes a Breeze in 20 Minutes

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In this episode of the Sunlight Tax Podcast, I’m breaking down my most effective tax prep strategies to help creatives and entrepreneurs start the year organized, confident, and ahead of the game. I share my January setup to make your taxes a breeze. I'll give you the exact systems I recommend for simplifying tax season without overwhelm or guesswork – like tracking mileage and mileage logs, setting up a simple document filing system, knowing your 1099 requirements, and a receipt management workflow that’s easy to maintain all year long.

If you want to avoid costly tax mistakes and move through tax season smoothly, this episode gives you actionable tools you can implement right now. Whether you're self-employed, earning 1099 income, or running a creative business, you’ll walk away with a clear plan for staying compliant, reducing stress, and setting yourself up for a better money year.

Listen and Subscribe Here

In this episode of the Sunlight Tax Podcast, I’m breaking down my most effective tax prep strategies to help creatives and entrepreneurs start the year organized, confident, and ahead of the game. I share my January setup to make your taxes a breeze. I'll give you the exact systems I recommend for simplifying tax season without overwhelm or guesswork – like tracking mileage and mileage logs, setting up a simple document filing system, knowing your 1099 requirements, and a receipt management workflow that’s easy to maintain all year long.

If you want to avoid costly tax mistakes and move through tax season smoothly, this episode gives you actionable tools you can implement right now. Whether you're self-employed, earning 1099 income, or running a creative business, you’ll walk away with a clear plan for staying compliant, reducing stress, and setting yourself up for a better money year.

Also mentioned in today’s episode:

01:12 New Year, New Tax Strategies

03:13 Essential Tax Preparation Tips

09:44 Understanding 1099s and Deadlines

14:01 Setting Up a Business Bank Account

15:54 Organizing Receipts for Tax Season

19:28 Other Resources

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.

Links:

The Sunlight Tax Podcast EP4: Mileage: the best deduction you're missing

Join my free class: Make Taxes Easier and Stash an Extra $152k in Your Savings

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