The Retirement Trap — Should You Really Stop Working at 65?
The Art of Manliness
The Art of Manliness
4.7 • 14.9K Ratings
🗓️ 23 June 2026
⏱️ 40 minutes
🔗️ Recording | Apple Podcasts | RSS
🧾️ Download transcript
Summary
The modern idea of retirement was built on a bet that turned out to be wrong. It assumed people would spend most of their lives working and only a relatively short period of time retired. Instead, many Americans now reach 65 healthy, active, and with an entire third of their life ahead of them. Yet we're still using a retirement model designed for a world in which old age was shorter and fewer people expected decades of life after leaving the workforce.
My guest says that outdated assumption creates some unfortunate unintended consequences. It causes people to stress excessively about money, postpone meaningful experiences with family and friends, and sometimes sacrifice the very things that make life worth living in the first place. He argues that by rethinking retirement — not necessarily eliminating it, but reimagining it — we can enjoy more of our lives now while actually feeling more secure about the future.
His name is Derek Coburn, and he's a financial advisor and the author of Let's Retire Retirement. Today on the show, Derek explains why the traditional retirement model came about, why it may no longer make sense for many people, and how working even a few years past 65 can dramatically change the math of retirement planning. We also discuss the surprising psychological challenges many people face after they stop working, why purpose matters more than leisure, and how thinking differently about retirement can free you up to spend more time on what matters most right now — whether that's traveling, strengthening your marriage, or making the most of the limited summers you have left with your kids.
Connect With Derek Coburn
- Derek's website (including his retirement calculator)
- Derek on IG
0:00 - Introduction
1:22 - The Outdated Origins of Retirement (Bismarck's 1889 Social Insurance Plan)
4:12 - Why the Traditional Retirement Model Creates Stress and Anxiety
6:13 - The "Arrival Fallacy" — Why Retirement Isn't What You Think It Will Be
8:42 - The Psychological Crisis of Stopping Work Cold Turkey
11:05 - The Math: How Working 10 More Years Cuts Your Savings Requirement by 96%
13:21 - Enjoying Life NOW Instead of Deferring It to Retirement
14:22 - Maximizing the Limited Summers You Have with Your Kids
19:48 - Sponsor Break
20:07 - What If You Hate Your Job? Find One You "Don't Hate"
22:37 - Side Hustles as an On-Ramp to Work You Love
24:09 - Physical Jobs and Mandatory Retirement — What Then?
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Transcript
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| 1:33.7 | Brett McKay here and welcome to another edition of the AOM podcast, |
| 1:37.0 | which since 2008 has featured conversations with the world's best authors, |
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