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March 17, 2025 21 mins

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Most people plan for retirement by focusing on their savings and investment returns—but what if some of the most important decisions happen after you stop working? 

In this episode, I sit down with Jeremy Keil, also known as Mr. Retirement, to discuss the three biggest mistakes retirees make—mistakes that can cost them financial security, tax savings, and peace of mind. 

From misunderstanding the best time to take Social Security to underestimating how long retirement will last, we break down the key oversights that can derail even the best-laid plans.

Jeremy and I dive into why retirement age and Social Security claiming don’t have to go hand in hand, how to accurately gauge your longevity to avoid outliving your money, and the crucial difference between optimizing for next month’s income versus planning for a lifetime of financial security. 

Whether you’re a few years away from retirement or already in it, this conversation will challenge the way you think about your financial future and equip you with strategies to make smarter decisions. 

Outline of This Episode

  • (0:00) Intro
  • (1:19) Mistake #1 – Tying retirement to Social Security
  • (4:05) Mistake #2 – Underestimating longevity
  • (8:41) Planning for an earlier retirement than expected
  • (13:50) Mistake #3 – Optimizing for short-term income over long-term security
  • (19:20) Where to find more from Mr. Retirement

Resources & People Mentioned

Connect with Jeremy Keil

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Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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