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

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Podcast: Startups For the Rest of Us (LS 58 · TOP 0.5% what is this?)
Episode: Episode 777 | Why Retiring Might Be the Worst Goal for Entrepreneurs
Pub date: 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 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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      The podcast and artwork embedded on this page are from Rob Walling, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.
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