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Tax and Money Education for Creative People, Freelancers and Solopreneurs

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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.

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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.

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Hannah Cole Hannah Cole

How To Issue Your 1099s

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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. 

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Stress Stopper: Plan For Your 1099s

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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. 

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1099 vs W2 Income and Why it Matters

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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. 

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