I Retired at 55 — 8 Regrets I Refuse to Have at 80

Early Retirement Roadmap · Oct 12, 2026 · 19m

I retired at 55, and I’m thinking about the retirement regrets I want to avoid by 80. These 8 early retirement lessons cover spending, taxes, cash, health, travel, marriage, and changing the plan as life changes.

I could make sound financial decisions and still regret how my wife and I used our years. After hearing about regrets people shared in their 80s, I asked myself which ones could become mine—and what I can do about them now.

In this episode, I talk about eight regrets I’m working to avoid:

Saving the best years for later

Making a permanent move too soon

Planning taxes one year at a…