Retirement Starts Today

The IRS Penalty Retirees Never See Coming (And How to Beat It)

June 29, 2026·21 min
Episode Description from the Publisher

Every year, thousands of retirees pay an extra penalty to the IRS — and almost none of them see it coming. What catches them off guard isn't a penalty for owing too much. You can do everything right — claim Social Security at the right age, run picture-perfect Roth conversions, manage your withdrawals down to the dollar — and still get a letter from the IRS charging you extra. I reworked a framework from an article by Sheryl Rowling at Morningstar into four clean, completely legal ways to avoid getting tax penalties. After that, we've got a listener question: A retiree writes in and says, "I don't want to think about money. My plan is tested, I have enough — so what's a simple checklist I can use to stay on track?"  And to close the show, our Retire To Something segment where Clif traded his to-do list for a garden plot — and found community, leadership, and a whole lot of homegrown vegetables in the process.   Resource: Article by Sheryl Rowling at Morningstar: 5 Ways to Avoid Tax Penalties    Connect with Benjamin Brandt: Subscribe to the This Week in Retirement: http://thisweekinretirement.com Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com Work with Benjamin: https://retirementstartstoday.com/start Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement Follow Retirement Starts Today in:Apple Podcasts, Spotify, Overcast, Pocket Casts, Amazon Music, or iHeart

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