Tue Jul 08 2025, by Tyler Gardner

Retirement PlanningFinancial RegretsHealth Care CostsQuality of LifePodcast

3 Regrets from People Who Retired Early

If this sounds like you, check out my new podcast, Your Money Guide on the Side, by clicking the link in my bio.

1. Underestimating Health Care Costs

I see you! Medicare isn’t free, and private insurance at 62 can be a horror show only rivaled by used car dealerships.

2. No Plan for Their Time

They had no plan for their time. It turns out you can only play so much golf before you start missing all-hands meetings. I promise that’s going to happen. Retirement isn’t just about leaving work; it’s about replacing purpose.

3. Waiting Too Long to Practice Spending

Many retirees didn't practice spending soon enough. We're rewarded and applauded for saving for decades, which teaches frugality. But spending requires a whole new muscle. Many retirees are rich on paper but emotionally broke.

Conclusion

If any of this is helpful, check out the new podcast where we’ll explore this in more depth.

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