The Stacking Benjamins Show What Retirees Wish They'd Known 10 Years Ago (SB1758)
10 snips
Nov 7, 2025 
Join Jill Sirianni, co-host of Frugal Friends and author on values-based spending, Jesse Kramer, a personal finance podcaster and CFP-adjacent expert, and Doc G, host of Earn & Invest, as they delve into the five biggest retirement regrets people face. They discuss the pitfalls of poor investment strategies, tax blunders, and the importance of estate planning. The guests share valuable insights on enjoying your money rather than hoarding it, making this a must-listen for those planning ahead!
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Gradually Adjust Asset Allocation
- Shift your asset allocation gradually 5–10 years before planned retirement to avoid last-minute risk exposure.
- Consult a CFP for a tailored glide path and cash needs before decumulation begins.
Too Aggressive Right Before Retirement
- Jordan recounts being too equity-heavy when his wife unexpectedly retired within months.
- They were fortunate markets were high, but the rush exposed the risk of last-minute reallocations.
Hire Help Near Retirement
- If you're 5–10 years from retiring, pay for one-time financial advice to set allocation and cash targets.
- Use a planner to design a transition that meets income needs and reduces sequence-of-returns risk.
