Mon Aug 18 2025, by Tyler Gardner

Retirement PlanningFinancial LiteracyEmotional HealthPersonal FinanceInvestment Strategy

What No One Tells You About Money in Your First Year of Retirement

I'm Tyler, a former financial advisor and portfolio manager. If any of this is helpful, sign up for my free newsletter by clicking the link in my bio.

1. The Freedom is Accompanied by Anxiety

You thought you'd feel free, but now you feel anxious. Why? Because your entire adult identity was tied to productivity, and now your calendar's empty.

2. Second Guessing Withdrawals

You’ll second guess every withdrawal after having saved for 30 years. Spending your own money can feel downright illegal.

3. Focus on Repurposing, Not Just Returns

The first year isn’t about returns; it’s about repurposing. Find routines, meaning, and structure. Otherwise, retirement can become unemployment with hobbies. So don’t just plan to stop working; plan for what starts next.

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