Why $4M Still Doesn't Feel Like Enough to Retire (Listener Q&A)

Why $4M Still Doesn't Feel Like Enough to Retire (Listener Q&A)

June 25, 2026 · 43 min · Episode 289

About this episode

The episode explores the psychological barriers to retirement despite having sufficient savings, featuring insights from a behavioral finance expert.

At 63, David has $4 million saved. Two advisors have told him he's ready to retire, and every Monte Carlo simulation agrees... but he still can't bring himself to do it. "I'm no longer being smart," he admits. "I'm just scared to pull the trigger." The uncomfortable part is that no number may fix this, because what's holding David back was never on the spreadsheet. In this episode, I'm joined by Daniel Crosby, Ph.D. — a psychologist and behavioral finance expert — to answer listener questions about the part of retirement the math can't solve. You'll learn: → How to spend in retirement so the enjoyment doesn't wear off so fast → A 3-part framework for putting your money where it creates the most happiness → When changing your plan is wise, and when it's just reacting to noise → The 2 questions to ask when you're financially ready but still can't pull the trigger → What actually moves the 40% of your happiness that's within your control By the end, you'll have a clearer way to separate a plan that works on paper from a retirement you actually feel ready to live. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare…

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