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TBPN · 7 min · Jul 13, 2026

Financial independence is about choosing your problems

Morgan Housel says founders can lose purpose and identity after selling, even when they have financial security.

In this episode

Full analysis
  1. 1:58:39Apple’s lawsuit may slow OpenAI before it reaches court8 min
  2. 1:28:49Rising home prices don’t always make homeowners wealthier7 min
  3. 51:15Live events can endure because human experience mattersPro pick 4 min
  4. 2:05:57OpenAI held a stake in IO before acquiring it4 min
  5. 2:09:38Apple plans to pass memory costs on to iPhone buyers3 min
  6. 57:51Nebraska women’s volleyball outsells men’s football in cards4 min
  7. 1:40:49Financial independence is about choosing your problems7 min
  8. 1:08:33Ohanian favors peer-to-peer markets over house-edge gambling5 min
“I always think the purpose of financial independence is to get to choose your problems”
Morgan Houselat 1:40:54 · TBPN
1:40:54

Takeaways

  1. Some founders regret selling when their business was their purpose.
  2. Housel sees boredom as harder than hard work.
  3. Financial independence can expand your choices without removing all problems.

About this segment

Morgan Housel says founders can lose purpose and identity after selling, even when they have financial security. He argues that meaningful work matters more than simply having enough money to retire.

Morgan Housel

Partner, Collaborative Fund

Wrote The Psychology of Money and Same as Ever, bestselling books on behavior, investing and how people think about money.

  • John Coogan, Host · Co-host, TBPN

    Co-founded Soylent and Lucy; OpenAI bought his show TBPN in April 2026.

  • Jordi Hays, Host · Co-host, TBPN

    Founded Branded Native; co-founded fintech Capital, which Rho bought.

From “Apple vs OpenAI, Mustard Controversy, Mark Gurman, Alexis Ohanian, & Morgan Housel Join”, Jul 13, 2026. Watch the full episode

Transcript

From the transcript TBPN publishes with the episode.

  1. 1:40:57

    Do you ever plan to retire? I think it depends. I always think the purpose of financial independence is to get to choose your problems Mhmm. Because you're going to have problems either way. And I was talking about this with someone earlier, of people who sold their business. I don't know if you guys know two people who sold their business recently. I don't know. But the number of them who went on to regret it, and the reason is this apply to you guys is because they left their business and they realized on day one, like, that was their purpose.

  2. 1:41:27

    That was their purpose. And once they loft it, that was their identity. And they woke up the next morning with tons of money and no purpose. Mhmm. And I would say, if you think work is hard, try boredom. It's way harder. Mhmm. It is way more psychologically taxing than hard work. People want good problems in life. Yeah. And so retire no. I I'll I'm I'm doing I I work very differently now and do a different level of Yeah. Less work than I did five years ago, but I'm still doing things to keep myself busy because if I didn't, I would slip into boredom and then probably depression very quickly. So I guess to answer your question now.

  3. 1:41:57

    Yeah. Yeah. There's some formula. It's like how much you should invest in bonds is like your age minus one one hundred minus your age or something. It's like how much free time you should have should be like 100 minus your age. So when you're 20, you're working 80% of your waking hours. But when you're 50, you're taking half the time off or something. I don't know. There there there's some, like, you know, you wanna have some sort of balance. You probably can't go hundred hour weeks into your eighties unless, I don't know, maybe somebody will, but

  4. 1:42:26

    It's a big problem because in finance, we spend so much effort making sure people have enough money to retire Yeah. And focusing on that number. Yeah. And no time whatsoever asking the question, what are you going to do once you're retired? Sure. And for a lot of people, they retire, they got plenty of money, they saved their whole life. They don't know what to And then after two weeks of retirement, they wake up and like, who am I? I I don't even know what I am anymore. What's my identity? What's my purpose? And if they retire at 60, they might have another forty years to live.

  5. 1:42:51

    Yeah. Like an entire extra life to live doing nothing. Yeah. Long time. Nurburgring Track time. Sub seven minutes. Make it happen. That That'll be John. That is

  6. 1:43:03

    It'll be the it'll be the 80 year old on the on the track. He's shaving off milliseconds. Alright, grandpa.

  7. 1:43:08

    I don't think it's put you to bed. Think I'd have a disadvantage forever. I don't know. Maybe I

  8. 1:43:13

    I'm glad Let me let me flip that around to you guys. Young guys, successful, sold your business, do you think you'll ever retire?

  9. 1:43:18

    No. Absolutely not. I saw my my my late grandfather was sharp as a tack until about three months after he retired. And I think that I think that the daily habit of just putting putting in work, you know, using his mental capacities. Yeah. I would like to was contributing to his longevity. And to me to me, the you know, building companies is like an act of creation and there's nothing as as satisfying or enjoyable to me in this whole world than creating. Yeah. And so to me, it's like it's like Not going anywhere. You're asking an artist like, do you think you'll ever stop like, you know, making art?

  10. 1:44:07

    Yeah. Yeah. You might you might dial it back, you might do these different things, but No. I'm I'm so fascinated to I I I like I like to imagine, like, if I was 80 years old right now, living the same life, what what would I be choosing to work on? What what ideas? And I I think they'll be quite I think they'll be quite different than the things that are interesting to me now. Yeah. But I look forward to

  11. 1:44:37

    figuring would say, out like, there are some fields that I really admire when people quit while they're ahead. Whether it's like Seinfeld in 1998 shows On Top of the World and he's like, no, we're done. That's I've given it all to our team. We're out of here. But he didn't retire. He's still on tour today doing a million other things. Yeah. And so the ability to say, I could probably squeeze more juice out of this career, whatever that career might be, but I'm proud of what I've achieved and now I'm going to go do something else. It's not retirement, but I admire that versus you could easily imagine a history where Seinfeld went another ten seasons, it sucked, and it just kind of, like, died on the vine. Can easily imagine that history, which is kind of what the Simpsons have done over the last twenty years. Right? And so I I I really like when people quit while they're ahead.

  12. 1:45:21

    Think it's really admirable. Yeah. There's also something there's like a kind of business that can only be started by someone who doesn't need it to work, basically. And you see this with startups where, like, you know, an entrepreneur will have an exit and they'll start working on something and then they'll just be toiling in obscurity for years and and, you know, and and eventually they can build something valuable out of it. But a young entrepreneur wouldn't necessarily do that because they're like, have to I have to make the SaaS so that I can raise the next round, so I can, you know, do all these different things. And so, I also think it just changes when you when you have like if you can set yourself up to be able to take more risk, there's interesting businesses to be built.

  13. 1:46:08

    Yeah. I forget who said this years ago. May have been Mike Salana. I might be getting that wrong. But he said, like, the number of founders founders that he's met who sold their business, cashed out, and then they said, I'm gonna take two or three years off to just chill Mhmm. And ski with my family and hang out, and then I'm gonna come back. And they come back after three years, and I think the way he phrased it was, like, every one of them is so smooth brained at that point. Like, you just lost it. Like, you just atrophyed. They lost the edge of what you had.

  14. 1:46:33

    And so the idea too that it's a muscle that you got to keep going or else it's just going to wither away is important too.

  15. 1:46:40

    Yeah. Yeah. It seems like the there are there's, like, a different set of challenges that the post exit founders can take on that that that works. But if the if the business requires, like, having really, you know, like like, firm contact with, you know, a large swath of consumers and you haven't been to the store in four years because you now have a personal shopper, like, you might be out of touch there. But if you're solving some sort of problem on the, like, geopolitical level marshaling billions of capital and it's like that was an opportunity that was only open to you after you exited, then that becomes something that's you can accelerate into a little bit better.