Tax Season Blunders to Learn From and Avoid episode artwork

EPISODE · Feb 9, 2026 · 42 MIN

Tax Season Blunders to Learn From and Avoid

from Retired-ish

If you're doing your own taxes or working with a tax preparer who doesn't specialize in wealth accumulation, financial planning and retirement, there's a good chance you're leaving thousands of dollars on the table every single year. We're talking four and five-figure mistakes that happen because nobody's looking at the details. In this episode, Cameron walks you through six of the most expensive tax blunders he sees wealth accumulators and retirees make - from losing track of IRA basis to triggering Medicare surcharges you didn't see coming. These aren't theoretical problems. These are real mistakes costing real people real money. Learn about these potential issues before they arise so you don't make the same mistakes! More specifically, Cameron discusses: 1. Losing Track of Form 8606 and Non-Deductible IRA Basis 2. Estimated Tax Payment Disasters 3. The IRMAA Time Bomb & Medicare Premium Surcharges 4. QCD Mistakes 5. Missing Cost Basis on Old Stock Positions & Paying More Taxes Than Necessary 6. State Tax Exempt Interest and Dividend Mistakes Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up See if you're a good fit for our Free Tax-Optimized Retirement Playbook™ Key moments: (00:00) Tax Season Blunders to Learn From and Avoid (05:33) 1. Losing Track of Form 8606 and Non-Deductible IRA Basis (12:28) 2. Estimated Tax Payment Disasters (18:10) 3. The IRMAA Time Bomb (22:56) 4. QCD Mistakes (28:16) 5. Missing Cost Basis on Old Stock Positions (32:30) 6. State Tax Exempt Interest and Dividend Mistakes

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