THE SUNLIGHT TAX BLOG:

Tax and Money Education for Creative People, Freelancers and Solopreneurs

1099 Problems (and How to Avoid Them)

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.

1099 Problems (and How to Avoid Them)

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

Get my short course: All About 1099s

Check out my program, Money Bootcamp

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

Get your free visual guide to tax deductions

Watch YouTube video version.

Read More

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

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.

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:

Get my 1-hour course: All About 1099s

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

Check out my program, Money Bootcamp

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

Get your free visual guide to tax deductions

Watch YouTube video version

Read More
Hannah Cole Hannah Cole

How To Issue Your 1099s

Listen and Subscribe Here

Today, I’m going over the importance of issuing 1099 forms if you’re self-employed, including who needs to receive them, the deadlines and penalties involved if you miss it. 

Tune into this episode to get an understanding of the 1099 process and to get strategies to simplify issuing 1099s, so you can stay organized and avoid any penalties. 

Listen and Subscribe Here

Today, I’m going over the importance of issuing 1099 forms if you’re self-employed, including who needs to receive them, the deadlines and penalties involved if you miss it. 

 

Tune into this episode to get an understanding of the 1099 process and to get strategies to simplify issuing 1099s, so you can stay organized and avoid any penalties. 

 

Also mentioned in today’s episode: 

 

  • Types of 1099 forms and their uses 5:30

  • Who needs a 1099 and who doesn’t 6:56

  • Action checklist for issuing 1099s 19:00

 

If you enjoyed this episode, please rate, review and share it! 



Links:

Blank W9 for you

My course on issuing 1099s

Check out my program, Money Bootcamp.

Watch YouTube video version.

Read More

Stress Stopper: Plan For Your 1099s

Listen and Subscribe Here

Today, I’m talking about the importance of preparing for tax season specifically when it comes to issuing 1099 forms, including when you need to issue one and the deadline. 

Join me in this episode to learn how and when you need to obtain your W9 forms and issuing your 1099’s from your contractors. 

Listen and Subscribe Here

Today, I’m talking about the importance of preparing for tax season specifically when it comes to issuing 1099 forms, including when you need to issue one and the deadline. 

 

Join me in this episode to learn how and when you need to obtain your W9 forms and issuing your 1099’s from your contractors. 

 

Also mentioned in today’s episode: 

  • 1099 requirements 4:10

  • Compiling contractor payments 4:43

  • Gathering W9 forms 6:50

  • Preparing for 1099 issuance 9:53

 

If you enjoyed this episode, please rate, review and share it! 

Links:

FREE LIVE CLASS: Make Taxes Easier and Stash an Extra $152k in Your Savings 

Watch YouTube video version

Read More

1099 vs W2 Income and Why it Matters

LISTEN AND SUBSCRIBE HERE
1099 vs W2 Income and Why it Matters

Today on the podcast, I’m going over the key differences between 1099 freelance income and W-2 employee income when filing taxes and how you can simplify your taxes as a self-employed individual. 

Join me in this episode to learn how to file your taxes correctly to avoid penalties and keep your finances simple. 

LISTEN AND SUBSCRIBE HERE

Today on the podcast, I’m going over the key differences between 1099 freelance income and W-2 employee income when filing taxes and how you can simplify your taxes as a self-employed individual. 

 

Join me in this episode to learn how to file your taxes correctly to avoid penalties and keep your finances simple. 

  

Also mentioned in today’s episode: 

  • The main differences between 1099 and W2 income when it comes to taxes 2:30

  • The importance of bookkeeping when you’re self-employed 5:45

  • The importance of keeping records and being prepared for IRS inquiries 14:53

If you enjoyed this episode, please rate, review and share it! 

Links: 

FREE MASTERCLASS: Make Taxes Easier and Stash an Extra $130k in Your Savings

sunlighttax.com/deductions

Watch the Youtube video version

Read More

What are your money concerns?
Suggest a blog topic for Hannah here.