DIY Taxes: Smart Move or Costly Mistake?

Tax software makes it easier than ever to file your return on your own, but just because you can do your taxes yourself, doesn’t mean you should. In this episode, Wade explores when DIY tax filing makes sense and when it could lead to costly mistakes. If you’re a W-2 employee with no extra income streams, doing your own taxes might be just fine. But add a rental property, a home sale, a K-1, or retirement distributions, and the risks start to grow quickly.

Wade shares the most common errors he sees in self-filed returns, from misreporting investment income to missing out on valuable deductions. He also explains the key difference between tax preparation and true tax planning, and how financial advisors and CPAs can work together to spot opportunities before they expire. If you’ve ever used DIY tax software and found yourself wondering if you did it right, you’re not alone. Find out how you can make more informed choices for next year’s tax season.

Here’s some of what we discuss in this episode:

🧾 When DIY taxes actually make sense

🚨 Common self-filing mistakes that trigger IRS letters

💡 The difference between tax prep and tax planning

🤝 How advisors and CPAs team up for better outcomes

🧠 Missed deductions = missed opportunities

Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 

The opinions voiced in The Money Knight podcast with Wade Chessman of Chessman Wealth Strategies are for general information only and are not intended to provide specific advice or recommendations for any individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing.

Investment advisory services offered through CWM, LLC, an Investment Advisor. Carson Partners, a division of CWM, LLC, is a nationwide partnership of advisors.