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

Startups For the Rest of Us

Rob Walling

Management, Entrepreneurship, Business, Marketing

4.8 • 792 Ratings

🗓️ 3 June 2025

⏱️ 29 minutes

🔗️ Recording | iTunes | RSS

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Summary

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! Subscribe & Review: iTunes | Spotify

Transcript

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0:00.0	Welcome back to another episode of Startups for the Rest of Us. I'm your host Rob Walling, and in this
0:05.0	episode, I talk with Derek Coburn, the co-author of the book, Let's Retire Retirement, How to
0:11.1	Enjoy Life to the Fulest, both now and later. And we cover a bunch of topics, one of which is why
0:17.6	retiring might be the worst goal for entrepreneurs.
0:23.8	I really enjoyed my conversation today with Derek,
0:27.4	and it relates to things that I often talk about on this show where we're not just about building the biggest startup for all the money
0:31.8	and sacrificing your life and your health and your relationships.
0:35.0	We're about building a startup that provides you freedom,
0:38.8	purpose, and the ability to maintain healthy relationships. And that really is a big part of the
0:44.2	focus of my conversation today with Derek. But before we dive in, I want to let you know.
0:50.4	Late September of this year, I'm going to be an Istanbul Turkey for MicroConf Europe.
0:55.1	We're going to have a handful of amazing talks. We're going to have amazing excursions and, of course, our world-class hallway track.
1:03.8	Speakers so far include Michelle Hansen, the founder of Geocodeo and the author of Deploy Empathy.
1:10.3	Mark Thomas, the founder of Positive Human. James Mooring, the founder of Geocodeo and the author of Deploy Empathy, Mark Thomas, the founder of positive
1:12.2	human, James Mooring, the founder of Astalti, and of course, yours truly.
1:17.5	MicroConf.com slash Europe, if you want to buy your ticket, tickets are as inexpensive as they
1:23.7	will ever be. If you want to get a ticket and don't want to miss the event
1:27.6	because the event will sell out,
1:29.4	we've sold out all the microcoms
1:30.8	for the past couple years,
1:32.4	you should go to microcomf.combe.
1:34.5	And pick up your ticket
	...

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