THE SUNLIGHT TAX BLOG:

Tax and Money Education for Creative People, Freelancers and Solopreneurs

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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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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.

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How to Fix an Incorrect 1099

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Today, I’m talking about the common problem of receiving an incorrect 1099 as an entrepreneur, including what you need to look for and how you can make the corrections to avoid any problems with filing your taxes. 

Join me in this episode to get all of the details needed for correcting any 1099s that may have errors and what you can do to avoid any issues with filing. 

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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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