Don’t Let Taxes Terrify You w/ Hannah Cole #1064

14 snips

Nov 19, 2025

Hannah Cole, a tax educator and founder of Sunlight Tax, aims to demystify taxes for the self-employed. She shares her mission to empower creatives to embrace deductions, bookkeeping, and filing without fear. Hannah discusses the forgiveness of the IRS, the importance of organizing receipts, and understanding when a hobby becomes a business. She also highlights the advantages of starting a business in the U.S. and why DIY taxes can be a smart choice for many. Tune in for practical tips and a refreshing take on tax worries!

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ANECDOTE

Artist Tax Humiliation Turned Lesson

Hannah described a humiliating visit to her dad's accountant who treated her art practice like a hobby.
She had missed a $4,000 mileage deduction because the accountant didn't recognize her work as a real business.

INSIGHT

1099 Work Is Officially A Business

Many people don't realize 1099 income counts as a business under U.S. tax code.
That status allows self-employed people to deduct ordinary business expenses and access meaningful tax benefits.

INSIGHT

Losses Are Built Into Startup Tax Logic

A Schedule C reports profit or loss from business, not just profit.
Reporting a loss can reduce household taxable income and intentionally supports new businesses.

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“Taxes for creatives” could have also been the title of this episode, giving the more entrepreneurially minded the boost they need to officially launch a little business they’ve been considering. But for most folks the topic of taxes isn’t comforting, it’s straight up terrifying… even though it shouldn’t be. Today’s guest, Hannah Cole, is on a mission to create fearless folks who launch into the world of deductions, bookkeeping, tracking, tax filing, and all the other terms that strike a little fear in your heart, with full confidence. Her new book, Taxes For Humans, acts as a field manual for self-employed folks to simplify their taxes and take the bull by the horns. Topics covered today:

Taxes can be intimidating, but understanding them is empowering
Creatives often struggle with the business side of their work, including taxes
The IRS is more forgiving than many people think
Receipts, tax forms, and bookkeeping are the key three systems
Deductions are available for ordinary and necessary business expenses
When and how much in quarterly estimates, in order to avoid penalties
A visual guide to tax deductions
And much more!

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:

Be sure and check out Hannah’s new book, Taxes For Humans, or just get it on Amazon. And her visual guide to tax deductions is especially cool for folks looking to organize their business expenses, who also hate IRS forms ;)
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