Thinking Solo

Estimating Taxes


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Self-employed? Then listen up: revenue is not profit, and profit is what really matters.


In this episode of Thinking Solo, Ryan breaks down one of the biggest financial traps business owners fall into: getting paid, feeling flush, and forgetting that taxes are coming. If you’re running your own business, estimated taxes are not optional planning fluff. They are part of running the business like an adult.


Ryan walks through why self-employed professionals need to start with expected profit, account for self-employment tax, set aside money consistently, review their numbers quarterly, and actually pay estimated taxes on time.

Because nothing crushes momentum faster than thinking your business is doing great, only to get hit with a tax bill you were not prepared for.


What You’ll Learn


✅ Why revenue can give business owners a false sense of success

✅ Why profit matters more than top-line sales

✅ How self-employment tax can surprise new business owners

✅ Why setting aside a consistent percentage for taxes can help avoid panic later

✅ The importance of quarterly reviews and updated estimates

✅ Why actually paying estimated taxes may give you a clearer picture of business cash flow

✅ How penalties and interest can make an already painful tax bill worse


If you are self-employed, taxes need to be built into your business process from the beginning. The goal is not to guess perfectly. The goal is to avoid surprises, stay consistent, and understand what your business is actually producing after expenses and taxes.


Also in This Episode


Ryan wraps up with a review of the 1984 cult classic Repo Man, starring Emilio Estevez and Harry Dean Stanton. It is strange, scrappy, funny, and weirdly fitting for anyone who appreciates the chaos of trying to make your own way.


Connect with Ryan Derousseau, CFP

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/ryanderousseau/

Website: https://thinkingcapfinancial.com/

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Thinking SoloBy Ryan Derousseau, CFP®, EA