Episode 777 | Why Retiring Might Be the Worst Goal for Entrepreneurs

2025-06-03

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What if the traditional dream of retirement is actually a trap for entrepreneurs? In this episode, Rob Walling talks with Derek Coburn, author of Let’s Retire Retirement: How to Enjoy Life to the Fullest, to challenge the long-held belief that early retirement is the ultimate goal. They explore why many entrepreneurs feel unfulfilled after retiring and how shifting toward purpose-driven work can create more freedom, meaning, and longevity. Topics we cover: (2:17) – Why traditional retirement often lead...

What if the traditional dream of retirement is actually a trap for entrepreneurs?

In this episode, Rob Walling talks with Derek Coburn, author of Let’s Retire Retirement: How to Enjoy Life to the Fullest, to challenge the long-held belief that early retirement is the ultimate goal. They explore why many entrepreneurs feel unfulfilled after retiring and how shifting toward purpose-driven work can create more freedom, meaning, and longevity.

Topics we cover:

(2:17) – Why traditional retirement often leads to boredom and regret
(6:44) – How working longer can drastically reduce your savings burden
(11:05) – The power of $50K moments and appreciating time with loved ones
(17:03) – Prioritizing health and well-being as a long-term strategy
(21:42) – Smarter and more flexible alternatives to full retirement

Links from the Show:

MicroConf Europe – September 28–30 · Istanbul, Türkiye
TinySeed – Invest
Let’s Retire Retirement – Book on Amazon
Derek Coburn’s Website
Derek Coburn | LinkedIn
Derek Coburn (@cadredc) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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