Tax Planning Without Tears: Artist and Expert Hannah Cole’s Guide

Welcome back to Don’t Retire… Graduate! For our season six finale, I was thrilled to talk taxes in a way you’ve probably never heard before. Today’s episode features a conversation with Hannah Cole, tax expert, author, founder of Sunlight Tax, and a practicing artist who is on a mission to demystify tax planning for creatives, freelancers, and small business owners. Not only does Hannah Cole bring a wealth of knowledge from both the art and tax worlds, but she also brings a bit of humor and a whole lot of practicality—just check out her new book, "Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self Employed," and her PG-rated "Tax Dominatrix" character! In this episode, Hannah Cole and I dig into why tax education is so hard to find for creatives and what inspired her to blend a career as a professional artist with expert tax advice. We talk about her journey—staying an artist while becoming a tax pro—and why that dual perspective matters for artists, freelancers, and anyone trying to turn a side hustle into a sustainable business. We get into the weeds on the distinctions between LLCs, S Corps, and sole proprietorships, but with an approach that isn’t just technically sound—it’s grounded and totally accessible. Hannah Cole breaks down concepts like her "Power Triangle" (tax-smart saving, tax planning, and investing), discusses the difference between tax planning and tax filing, and explores the shades of gray between tax avoidance, evasion, and truly strategic tax moves. We also don’t shy away from big issues: the structure and complexity of the U.S. tax code, how to find a good and ethical tax pro, the realities of audits and IRS letters (why they’re scary for everyone!), and why a fairer and simpler system could benefit us all. We even debate the merits of estate taxes, VAT taxes, and the potential for a flat tax—always with respect, openness, and a sense that, with a little creativity, we could do more to make the tax system equitable and human friendly. Whether you’re an artist with a side hustle, a small business owner, or just allergic to the idea of tax planning, this episode will leave you feeling empowered and maybe just a little bit more optimistic about taxes. 5 Key Takeaways:Creatives Need Tailored Tax Help: Hannah Cole identified a huge gap for artists and freelancers, who are often stereotyped as being "bad at money," and built resources to help them thrive, including her book and visual guides.Tax Planning, Not Just Tax Paying: Tax planning is about making the system work for you—not just paying what you owe. It’s about grabbing “the coins in the couch cushions” and using the tax code’s incentives to your advantage, which is very different from the pain of cutting a check.Choosing the Right Tax Pro Matters: Not all CPAs are created equal. Hannah recommends prioritizing respect in your tax adviser relationships and being wary of anyone who’s aggressive to the point of danger. A good adviser makes you part of the decision-making process.Myths About the IRS and Enforcement: The societal fear of the IRS is often fueled by those who benefit from weakened tax enforcement. Hannah contends that, in practice, IRS agents are often kinder and easier to deal with than their reputations suggest—and that real “tax terror” often serves the interests of high-net-worth rule breakers.Calls for a Fairer, Simpler System: We debate estate taxes, sales tax, VAT, and even the promise of a flat tax. Regardless of where you stand politically, we agree: a fair, equitable tax code—one that doesn’t require an army of CPAs and endless stress—would benefit everyone. Join us for this engaging and lively conversation that will leave you rethinking what taxes can mean for your life and work. As we wrap up season six,...