Case against retirement

`3:02:05`

when you look at who the people like you, like really smart, creative humans, who they actually are and what happiness entails. It actually entails working your whole life a little bit. It's like because you actually love the programming, you love the building, you love the designer and you don't want to exit. And that's something you've talked about really eloquently about. So like you actually want to create a life where you're always doing the building and doing it in a way that's not completely taken over your life. — Mojito Island is a mirage. It always was. There is no retirement for ambitious people. There is no just sitting back on the beach and sipping a mojito for what? For two weeks before you go damn crazy and wanna get back into the action? That's exactly what happens to most people who have the capacity to build those kinds of exits. I've never seen, I shouldn't say never. I've almost never seen anyone be able to pull that off.

`3:03:05`

Yet so many think that that's why they're doing it. That's why they're sacrificing everything. Because once I get to the finish line, I'm golden. I've won, I can retire, I can sit back, I can just relax. And you find out that that kind of relaxation is actually hell. It's hell for creative people to squander their God-given creative juices and capacities. And I was really lucky to read the book "Flow" by Mihaly Csikszentmihalyi early on — Nice, the pronunciations, spot on. — You know what? I had to practice that with AI over the last few days because I knew I was gonna cite him and I butchered his name several times. So AI taught me how to pronounce that, at least somewhat correctly. But his main work over his career was essentially the concept of flow that came out of a search for understanding happiness. Why are some people happy?

`3:04:05`

When are they happy? And what he learned was quite illuminating. He learned that people aren't happy when they sit on Mojito Island. They're not happy when they're free of all obligations and responsibilities. No, they're happy in these moments where they're reaching and stretching their capacities just beyond what they can currently do. In those moments of flow, they can forget time and space. They can sit in front of the key board program a hard problem, think 20 minutes have passed and suddenly it's been three hours. They look back upon those moments with the greatest amount of joy. And that is what peak happiness is. If you take away the pursuit of those kinds of problems, if you eliminate all the problems from your plate, you're gonna get depressed. You're are not gonna have a good time. Now there are people who can do that, but they're not the same kind of people who built these kinds of companies. So you have to accept the kind of individual you are. If you are on this path, don't bullshit yourself. Don't bullshit yourself into thinking,

`3:05:06`

I'm just gonna sacrifice everything, my health, my family, my hobbies, my friends, but in 10 years I'm gonna make it all up because in 10 years I can do it. It never works out like that. It doesn't work out on both ends of it. It does not work out if you're successful and you sell your company, because you'll get bored out of your mind after two weeks on retirement. It doesn't work out if the company is a failure and you regret the last 10 years spent for nothing. It doesn't work out if it all works and you stay in the business because it never gets any easier. So you're gonna fail on all metrics if you just go, there's only work and nothing else. And I didn't want that. I wanted the happiness of flow. I understood that insight was true, but I wanted to do it in a way where I could sustain the journey for 40 or 50 years. — And there's another other interesting caveat that I've heard you say is that if you do exit and you sell your company and you wanna stay in, you wanna do another company that's going to usually not be as fulfilling. Because really your first baby, like.

`3:06:08`

— You can't do it again or most people can't do it again. A, because their second idea is not gonna be as good as the first one. It is so rare to capture lightning in the bottle like we have, for example, with Basecamp. I know this from experience because I've been trying to build a lot of other businesses since. And some of them have been moderate successes, even good successes, none of them have been Basecamp. It's really difficult to do that twice. But founders are arrogant pricks, including myself. And we like to think that, do you know what? We succeeded in large part because we're just awesome. We're just so much better than everyone else. And in some ways that's true some of the time. But you can also be really good at something that matters for a hot moment that door is open. The door closes now you're still good at the thing, but it doesn't matter. No one cares. There's that part of it. And then there's the part of it that going back to experience things for the first time only happens the first time. You can't do it again. I don't know if I have it in me to go through the of the early days again.