I Retired at 55—Why It Felt Wrong

Early Retirement Roadmap · Sep 21, 2026 · 12m

I retired at 55, but early retirement still felt wrong. In this episode, I explore why retiring before 65 can bring guilt, social pressure, and the uneasy feeling that you haven’t worked long enough.

Being financially ready for early retirement doesn’t mean your work habits and sense of responsibility disappear overnight. After decades of being rewarded for staying productive, making yourself useful, and showing up for others, stepping away from work can feel uncomfortable—even when your retirement plan is sound.

I share why age 65 has become such a powerful dividing line, how friends and…