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

Business Recovery After Hurricane Helene

After Hurricane Helene, Hannah relied on community and government infrastructure to recover.
The disaster highlighted the need for funded public resiliency and long slow rebuilding.

ADVICE

Digitize And Keep Receipts Seven Years

Digitize receipts and store them legibly for at least seven years.
Use access-controlled storage so you don't lose records if you change services.

ADVICE

Deduct Ordinary And Necessary Expenses

Deduct expenses that are 'ordinary and necessary' for your business.
Track mileage, meals, travel, and relationship-building costs but follow rules for frequently audited categories.

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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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