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Why Knowing When to Retire Feels So Hard

Some days, deciding when to retire feels obvious. Other days, retirement suddenly feels risky even though nothing has changed. In this video, I talk about why that back-and-forth happens when you’re tired of working but still afraid to retire. It’s not really about money or dates. It’s about what work gives us structure, identity, sense of being needed and what happens internally when that starts to loosen. I share how understanding that pattern can stop you from second-guessing yourself every time it returns. If you’ve been thinking about retirement and wondering why it feels clear one moment and uncertain the next, you’re not alone. Timestamps: 00:00- Intro 00:28- Identity Wrapped Up In Work O1:06- Retirement Clarity Isn’t Always Permanent 01:46- Identity Gap 02:01- When Retirement Feels Clear 02:32- Uncertainty Creeps In 02:49- Micro-mission Suggestions 04:45- It’s Ok To Be Scared