“The purpose of humans” - David Heinemeier Hansson

00:00

Caring about your legacy is caring about what other people think of you, which is, in my opinion, a flawed place to do any evaluation of your life. You should look back upon your experience and see, did I live a good life? Was this life long enough? On the last day, do I actually have any of those regrets? Did I waste my 20s and my 30s chasing work, maybe, to the detriment of everything else? Did I miss the childhood of my children because I was stuck in the office? Those are the kind of things that I think could seed you with regret. I strive to die on the last day feeling content about the time I spent here on this little blue dot.

00:52

How has the work of your parents influenced your work?

01:00

Wow, that's a good question. I think that has anchored in where that work was done and what kind of societal context it was done. I think perhaps that has a bigger influence than their particular jobs, but it's intertwined. I grew up in Copenhagen in the 80s, in a country that was and continues to be incredibly egalitarian, equal, where a class consciousness was not part of my experience until I was way, way older. It was not something I grew up with, and I think that really left a mark on my belief of who can do what, what kind of credentials do you need to check before you recognize whether they are doing the work that you are looking for or not.

01:49

I grew up lower working class with parents that worked for a living and had the opportunity to access great schooling, great healthcare, all the key factors of growing up in a... I was about to say civilized society. Maybe that's a little too pointed. But the opportunity that I was afforded through that experience meant that, when I showed up at Copenhagen Business School, age 21, was that right? Something like that. I felt like I was on the same level playing field as someone who had gone through a much fancier upbringing than I had, had gone to perhaps fancy private schools, had begun whatever fancy, fancy a certain class or financial position could have afforded them. It felt like it didn't matter at all, which is of course not always true in all domains, but it did feel true at Copenhagen Business School. Which actually be one of those places where you'd think that would matter, that there would be the mark of class, the separation of class, yet there wasn't.

03:04

So I made it all the way through, not just my primary school, my high school, but through college, my university degree, without feeling held back by the fact that I grew up where I did and from the economic circumstances I did. Which fundamentally left me with this belief that talent is evenly distributed. When I was then in a position to examine such talent, as, say, for hiring people, I was very keen to reflecting my experience. That was in somewhat of a contrast at 37signals to many other tech companies, especially in the U.S., especially the so-called premier ones, the Googles and so forth of the world, who seemed very eager to check credentials. It was very important to them whether you'd gone to Stanford or MIT or whatever.

04:02

Never important to me, obviously. And I think that really colored my way of engaging with other people on what terms we engage, that we engage, when it's about the work, on the work. And that's it. I don't care where you came from. I care in a human sense that it's nice to know your story, but I don't care in a gatekeeping sense as in whether you are worthy of, I don't know, my attention, our employment, anything else like that. I think the open-source movement really cemented that ever further. Open-source is this wonderful space where you meet people from all over the world, from even more diverse backgrounds than I did in Denmark in our relatively egalitarian society. I would work from people from Japan, from South America, from wherever, and if they showed up with a great patch, with a great PR, we would engage, we would have fun, and we would improve this framework we were working on together. So, yeah, it absolutely left a huge mark growing up like I did in the society that I did, and I continued to take that forward. Informs everything we do, informs how I think about work. I think that's probably true for most people, whether they acknowledge it or not, that the place they grew up left a mark, in some times positive and other times negative. But you are defined by how you spent the first years of your life. Of course you are.

05:40

Having heard you say some of the things that you said there before, I never realized that they might have come from your personal experience when you were younger. It wasn't something that I clocked necessarily.

05:54

I think it's also taken me some time to unravel that. I'll admit to that. I moved to the U.S. in 2005, and that was just a couple years after graduating. Actually, it was the year I graduated from Copenhagen Business School. Coming out of that, having only experienced living in Denmark, not all of these things were obvious, that they had left the mark the way they did. The obviousness did not appear until I experienced a different society with different values. The American one was very different, incredibly different, shockingly different, even, than the Danish society on a whole host of issues.

06:33

Even though, on the surface, on the veneer, it looks like, hey, we're part of the same cultural hemisphere, we're part of the same pop culture, we're part of a lot of the same circles, but, on some very fundamental points about how society is structured and what is the purpose of humans, we differ to a surprising degree. That really helped clarify to me what I stood for, why I stood for those things, what I liked about Denmark, and what I didn't like so much about Denmark. That contrast illuminated both my relationship to Denmark, to the United States, but also to work and to life.

07:21

Your reflection there is a consequence of your moving and being in a different culture. Have you proactively looked to reflect on your past and where your motivations come from at any point?

07:38

To some degree. I think mostly in form of a systemic analysis. What motivates me? What gives me drive? What gets me excited about things? How do I learn? Because I've applied those generalized principles to several domains. One of them is programming, another of them is business. Then, within business, there's marketing, there's organization. There's a lot of different domains all the way over to my hobbies, such as race car driving or photography. A lot of the same principles apply.

08:13

For me, some of those key ones are the role of flow, the ability to enter flow, the ability to enter this state where you're stretching your capacity and your competence just beyond what you can actually grasp. That's how you progress to the next level. A sense of a beginner's mindset, that I don't care to look foolish if I'm learning. That you learn much faster if you're willing to accept that others are better than you, they know more than you, they are faster than you, they take better photographs than you, they have gone further in business than you. On all domains, I have accepted, not just as a mode of learning but as a mode of being, that I'm never going to be the best at any individual thing because the odds of that are just so small. There's just one person who's the fastest race car driver in the world in any given field. There's just one person who's the richest man or woman in the world at any given one time.

09:13

If I define myself on a totem pole against that, it's always going to suck. No matter how high I climb, there's always someone who's going to be higher up the ladder than I am, so why even bother doing that? Instead, simply accept, hey, I am where I am and, if I want to progress, it's in a comparison to myself. It's being better than I was yesterday. It's accepting that I don't know everything, that I have so much to learn. Then find the people who do know more and learn as much as I can from them as quickly as possible such that I can progress and look back upon a year's worth of effort and go, "Oh, man. I'm better. This feels great." Because this is one of those things, that being addicted to improvement is a wonderful way to level up quick.

10:04

There are aspects of that that can turn too much. You can be addicted to improvement in such a pathological way that there's nothing else in your world than just improvement on a single track. That, too, I rejected quite early on both in life and my career. Again, acceptance that we're never going to be number one, not interested in chasing it. But I'll be good at a lot of things. You can become good at a lot of things if you don't allow one single pursuit to dominate everything forever, which again comes with that trade off that you're not going to be the best. There's only going to be one Michael Jordan.

10:42

All he did for that period of time that he was active was freaking go to the court and shoot baskets, right? The whole life and everything around was optimized for that. And I've gone, "I don't want that." I want to be good at running a business, so I'm going to do that diligently for about 40 hours a week. Then I'm going to spend my weekends at a race track, or traveling, or with my family or friends, or any of these other things that provide in my assessment a well-rounded existence that is something where, if any one of those individual things should falter, the business starts going sour or I can't progress in my racing or whatever, I have other legs to lean on here. It's not going to be the only one. I'm not going to tip over just because there's a single pursuit in life or single factor of my existence that if not falls apart, then falls sideways.

11:39

So building a resilient existence like that, that's based on multiple pillars of interest and time spent and so forth, that's something that I'm highly motivated and eager to keep up with, and something I learned quite early in my career that that mattered. As anyone probably has, I've gone through all sorts of shit over time, and you go, "Oh, man. This really sucks. Well, let's just go to the racetrack," or, "Let me go out and take some pictures. Let me do something else and help flush this out of the system, rather than just sit and ruminate over how terrible everything is."

12:23

To get to the point that you've got to, to these insights, it takes someone who really questions things, has ambition, who wants to know the truth and get to the heart of it. And that person typically is associated with ambition. So then it's very hard to come to terms with the trade off that you've got to make there, and the hedonic treadmill just keeps on going and keeps on going, and you don't know when to jump off. When did you know when to jump off?

12:56

It is a bit of a paradox. On the one hand, I am a highly ambitious person when it comes to my own self-improvement. But I try to curb that ambition by measuring myself against myself, not against this global thing. I think that, as I said, the hedonic treadmill is so much harder to jump off if you're constantly chasing someone else. If you're, quote, "just trying to improve yourself," I think it's easier to see that progression. It's easier to feel good about the station you're at. "Yes, I am the best me today that I ever was." It's like whenever Apple introduces a new iPhone, they're like, "This is the best iPhone we've ever made." I'd like to think that I can wake up every day and go, "I am the best me I could ever be."

13:49

That's not always true. There are certain steps back you take, but, on the long arc, that should be the direction things are heading. Versus, again, if I was comparing myself to other people in other domains, that would not be true most of the time. I would be a lot worse than a lot of other people. That sense of psychological safety there is in measuring yourself against yourself was something I discovered quite early on, I think. One of the reasons, for example, that I don't like individual sports very much, I don't like this sense that it's just me against the other person. There's just this sting if you lose. I don't like direct competition. I like asymmetrical competition. That, I love.

14:40

One of the reasons why I love business is I can run 37signals in a way where I feel great about it, even though, in terms of, say, market share, Google's kicking on our ass. Not just kicking our ass, we don't even exist. We're a gnat on the ass of that elephant, right? It's just not even there. We're not playing the same sport. Even though there are definitely entrepreneurs who are like, "I wake up in the morning to crush the competition." I'm like, "I don't" That seems to me like, again, you're going to keep meeting competition that is bigger and badder than you. Eventually, you're going to feel like, "Well, I wasn't good enough." When I could wake up in this asymmetric comparison and think, "I would not trade 37signals for Google." If you gave me the straight trade-up, I'd say, "No, thank you." That is a, in part, useful delusion in perhaps the minds of others that I employ to live a happy life.

15:39

Some of that was, for whatever reasons, just thoughts that were popping up in my head early on. This aversion to individual sports and so forth was something I had quite early. But, in my mid-20s, I then found, and this sounds like I'm ringing your doorbell here and I'm about to sell you a little book, stoicism. Where I really found a resonance in the ideas and thoughts of everyone from Marcus Aurelius, the emperor of Rome, to Seneca, an advisor and a philosopher, to Epictetus, a former slave. All these people who had developed this coherent philosophy of life 2000+ years ago. And I went, "Yes!" I had a poorly designed version of that program. Let me install a little bit more of the 5.0 of the good life into my brain.

16:42

It really just gave me the of the confidence that, do you know what? This magic tingling I'm feeling in my fingers, this direction I've been on, on my own, I'm not the only one who thinks this. There are other people who think this. There are other people who see the life and their satisfaction in the things that they can affect and try to not let outside circumstances dictate how they think about things and feel about things. This is good. This is helpful. So it came early on, it was reinforced by the discovery of stoicism, and it continues to be something that I practice on, essentially, a daily basis. Because I think the draw, particularly in our culture, is towards one of the hedonic treadmill, is towards one constantly of comparison to other people. On everything from how well is your business doing, to how many likes is your tweet getting, to how far is a blog post traveling, or all these other things that you can measure against others instead of just focusing on yourself.

17:47

It strikes me that all of that completely relies on a clear sense of self, whether it's stoicism or David or 37signals. You have to have such a deep understanding of your starting point in order to keep that outlook.

18:06

Yes, I think the power of introspection is incredible, and this is one of the things I not only just found in stoicism, but also in all sorts of other philosophies of life, Eastern philosophies. A lot of this Buddhism and meditation, and these techniques, and ways of thinking of allowing thoughts to enter your head and just see them float by without acting upon them. There are a lot of ways you can take greater control of your own mental processes. This is what I found to be the key appeal of stoicism. A way to wrestle control over these processes and deal with that in a more productive way, in a more conscious way.

18:54

So I deal with these emotions as anyone else do. I deal with whatever the uncured ambition, the jealousy, the disappointment, the anger, the resentment, all the human emotions we all have, to a larger or smaller degree, they pass through me as they do anyone else. But how you react to those things, especially in the long term, that's quite different, and you can absolutely learn to become better. Defined as being more in control and more aligned with, what are you looking for, what do you want? And not letting these impulses dictate your responses.

19:38

It's almost as if, to use the treadmill analogy, the treadmill is taking you somewhere, but that thing is not defined by you. And you have to introspect far enough to know what you're optimizing for. And at the moment you understand that, you're able to stop running towards the place the treadmill's taking you and you can jump off and go your own direction.

20:03

This is why in 20 years of running 37signals, together with Jason Fried, the most important aspect of that work, or the most important parameter or boundary, has been independence. Because all the introspection in the world is limited if you can't act upon it. I can notice things about my work situation that I, for example, go like, "You know what? This isn't great. I don't like this. I don't like where we're going. I don't like how we're doing it."

20:37

And then this incredible independence that we have enjoyed for two decades at this company allows me to, not just introspect on that fact, but to affect change. We can do things differently. We can change how we're doing things, we can change how we work, we can change the culture of the company if need be. And that is afforded to us by this independence, which has had tradeoffs, and some would call it sacrifices. That we have kept the company relatively small, entirely independent, without the rocket fuel of venture capital or any of the other accelerants you might have poured on something like us, and some would look at that and go like, "You have no ambition. Why didn't you take on Google? Why didn't you try to become a unicorn?" But then you do all these other things.

21:27

And for me, it wasn't worth the trade. If I lost this fierce independence we're able to have at 37signals, what is all the material rewards in the world going to do for me? I was not interested in that trade. So setting up conditions such as that we were able to exercise the conclusions that we would derive from this introspection is the thing that really just feels blessed, to use a religious term here. Because it is one of those things that I also think is a reinforcing agent. Now, I am being rewarded with dopamine when I have an insight into different ways of working, and I'm able to put that into practice. Sometimes immediately after having the idea. That is a immensely gratifying way of working that I would not trade for any other arrangement of work.

22:32

I guess you've got two identities. You've got your identity that you're learning about over time, and you've got your company's identity that you're learning about over time. Is there ever a contradiction?

22:48

There has been over the years, but I'd like to believe that whenever there is, that introspection notices, it notices the incongruence, and it tries to correct. Now, all those corrections don't always happen immediately. They don't always happen. I would personally just prefer in my ideal version to see, I share the ownership of this company with Jason Fried. And even though we see eye to eye in almost everything, it's not everything. So there are times. That's with anyone in any circumstances, where there are degrees of compromise or even discontent. But to a large degree, I am able to, together with Jason, to draw conclusions from the introspection when there is incongruence between how the company's running and what we believe to be right, and just, and good, and all the other virtues you could stack on that, to change course. And we've done that several times over the years.

23:54

We had a really big change of course in 2014 when we decided that our product portfolio for thriving successful products were taking the company in a direction we didn't want it to go. That we were, at the time, 40 some people. We're realizing with a product portfolio of four applications, we couldn't do them all justice to the level of quality and dedication that we wanted. So we needed to either become a much larger company or let go of some products. And for most companies, what are you talking about incongruence? Of course, you should just hire more people. If you have the business to support it, you should grow, grow, grow, grow. And because of that incongruence and because of the independence, we were able to take a very counterintuitive, perhaps even controversial, choice to say, "Nope, do you know what? Instead of growing, let's just let go of three of the products, even though they are thriving growing businesses, and focus on the one that's doing the best. We can manage the one with the team we have and we can stay roughly about the size that we are until we should decide otherwise."

25:09

And that's a level of freedom in the execution of business that is precious. And I recognize this is one of those things where it's asymmetrical. Could Google, for example, decide that, do you know what? Ads on search results, that's actually not where we want to be. Let's let go of that. No, you can't. You can't change the direction of most things once they're in motion, once there's so many other people who depend on it and have stakes in it and interest in, and so on. And we've managed to keep our company, 37signals, small enough that it is amenable to change if we discover incongruences between how we are and where we want to go.

25:51

It's interesting how our personal identities, if we can understand deeply enough, do compound interest. So the more that you do that introspection, the deeper you can get, the more you understand about yourself. And as you're talking there, you almost sound exactly the same with 37signals. As if the more time that goes on, you are able to compound more and more identity that gives you an even clearer sense of what direction you should go in the future.

26:16

Yes. But also over the long enough timeframe, it's not just compounding, although that happens, it's also subtraction. Where you realize the things you used to believe to be true, or a direction you used to believe to be good, turns out not to be. And you then say, "You know what? Don't want that. Let me extract that, let me leave that." And that is true on the personal side, and the business side as well. I mean, I've gone through several of phases of my engagement with all sorts of different things. Social media for example, I have a very different engagement today than I did three years ago. And some of that comes from realizing, oh, do you know what? I thought I knew what I wanted or what I liked, but upon further introspection, upon further data and feedback, turns out that I don't.

27:10

What else have you subtracted in your own professional journey?

27:17

For the longest time, opportunity. Since starting working with Jason in 2001, until 2020, I said no to 99.95% of all, "Let me get to meet you. Should we have coffee? I have this great idea. I think you'd be really interested in." All of these opportunities that presents themselves when you're doing something, for that period, to me, presented themselves as distractions. That I could only do these things, I could only do the work that I was interested in doing if I turned down almost everything else, and really just focused on a small handful of pursuits, and then doing those as best as I could.

28:13

Because if you look at my professional career, for example, it's funny, I jumped on LinkedIn earlier this year, and you go to almost anyone's LinkedIn page and you go to experience, and there's all these points, and I did this and I did that. And you go to mine, there's one thing. I mean because there's nothing else that's relevant to list. There's like 37signals, 21 years and six months. Boom, done. That's a level of... You could positively cast this commitment or you could negatively cast, if you will, as a rejection of opportunity.

28:47

Over 21 and a half years, I've had a lot of opportunity do a lot of things, and I said no to all of it, essentially. I focused on ideas that were founded two decades ago, which in itself is sort of weird. Professionally, both in terms of business, but also in terms of my profession programming, I started Ruby on Rails in 2003. I'm still doing Ruby on Rails in 2022, and I'm really damn excited about it. So thrilled with the latest version, Rails seven, that came out. I'm still totally excited about Basecamp. I'm really excited about 37signals. These are things, parts that's been there for so long, and I mean plenty of other people perhaps would've gotten bored, or they would've found the incongruence that would've developed if they weren't constantly adjusting for it, suffocating, and they would've gone on to do something else. And maybe they could have become a serial entrepreneur, or had a big exit, or any of these other trophies you can be awarded as someone who does business. But I wasn't interested in any of that.

29:58

So say no to a lot of things. Probably the main thing that's sort of been cut out.

30:04

How do you know whether you're following loyalty there blindly?

30:10

To me, that's quite clear.

30:11

Tell me how you work it out.

30:12

Yeah, loyalty to me is usually invoked in this sense of a trade off when you're doing something you don't really want to do, but you feel like you have an obligation to it. I'm not at 37signals out of obligation. I'm not working on Ruby on Rails out of obligation. I am not still programming for Basecamp out of obligation. I am doing all these things because I really, really want to. Because it is still a source of intense energy, motivation, self-improvement, betterment. And I think I look at these things than, and I don't think like, "Oh, how could the grass be greener somewhere else?"

30:55

I've read enough tales of entrepreneurs who've either sold their business or chase something else, to have internalized that most people end up, to some degree, regretting it. Not all. There are the Elon Musks of the world who sell a payment service and then start launching rockets into space. And clearly enjoyed the rocket launching more than they enjoyed the payment services. But I think there are far more who had a good idea, who grew up with that challenge, who then thought like, "Oh wow, now I've arrived. I can sell my life's work. And because I'm so fucking good, I'm just going to get another better idea tomorrow. And I'm going to have all this money, and I'm not going to have these constraints, and it's going to be wonderful." And then it's not wonderful.

31:44

I'm entirely at ease and at peace with the idea that I've already had the best ideas of my life. In fact, I've just recently gotten even more convinced of that. I believed that for 10 plus years. But I recently read this wonderful book called From Strength to Strength that covers the evolution in life, the difference between fluid intelligence and crystallized intelligence. This idea of rapidly thinking on your feet, when do certain people in certain professions peak in terms of idea output and synthesis and so on. And I am entering that age. I'm 43. I'm totally at peace with the fact that my most creative breakthroughs that relied on that fluid intelligence may very well be behind me. Great. I've left my mark, I've done my contribution. I don't feel like I owe anything to anyone, including myself, to do more, to do bigger. No, this is great. I'm really enjoying it. I'm not saying that's going to be forever.

32:55

And I have actually, this is why I said for most of the years, up until 2020, I said no to everything. I've started saying yes to some things. I've started saying yes to an engagement in the Danish startup scene, for example. And I've made some startup investments in that scene, something I'd sworn off for the longest time because that was not opportunities that I was going to say yes to. And now suddenly, I am feeling like, well, do you know what? Everyone enters different phases in their life and they can make different contributions at those times. And that's maybe partly where I am. Great. Awesome. I am so happy. Life is a finite journey. I'd hate to live forever.

33:36

Sounds like acceptance. But the tricky part with acceptance is that you have to start off not having that acceptance. You have to have that drive, that determination to get to a certain place, and then you can find that acceptance. But the two feel like contradiction.

33:55

Well, I think the acceptance that I've borne with me, I mean I've tried diligently to prove upon, is the kind of acceptance that the stoics preach. That what you control is mainly what's inside your skull. You control your outlook. You control your responses, but you don't control what you get out of that. I can show up and I can do my best possible work, and the world can go, "Meh." Then I can show up, which has happened plenty of time, I do something haphazardly, a bit sloppy, and the world goes, "Wow, this is amazing." I go like, "Wait, what? You didn't like that other thing that I poured my heart and soul into. Then this thing, this is the thing you think is great."

34:44

I had one of those experiences when we wrote Rework, which is our best selling book from 2010. It sold over half a million copies. I think it's translated into 19 different languages. We once ran this survey on what's your favorite chapter? I remember looking at that list and going like, "Yeah, that doesn't match my favorite list at all." Some of those essays that are on the list of people's favorite essays is some of the ones I hate the most in the book. I've heard something similar from musicians where sometimes the hits they make, they go, "I don't knowwhy that was a hit. I don't even necessarily particularly enjoy this song. I would like to move on, but for whatever reason this is what the universe has responded to."

35:29

This acceptance that I control what I put in, I control how I engage, I control how I respond, But everything else, no. I should just accept it. Not just accept it, I should love it. This is the wisdom of amor fati. Love your faith because what else are you going to do? You're going to just sit and complain about things that are happening outside of your control. In which way is that going to improve your life? In which way is that going to make you better?

36:00

In fact, it's not often this happens, but on TikTok recently I was exposed to this brief thing. TikTok is this mindfuck in many ways that I'm still trying to wrap my head around. But this particular one was one of these things, yes, this just crystallizes it, which was one of these quote things that come up. The quote was, "Don't wish for things to be easier, wish for you to be stronger," or, "Work for you to be stronger." That idea that you should not wish for the world to be any different than it is, that's outside of your control. You control your response to that. You control your reaction to that, both short term and long term. You're like, "Shit. This was difficult. Man, I better get stronger so the next time it comes around, I'm better." It won't be difficult. In fact, it will be easy. This is one of the lessons I've learned over and over again in every single domain. These things that seem like insurmountable challenges early on when you're just getting started, they will be nothing once you're a little further.

37:15

It's funny because in racing, for example, I'll sometimes take someone out in a race car, in a two-seater race car. Because I have a passenger and whatever, I dial it back. I drive at 90%. Driving at 90%, for me, means I have time for all sorts of other things. We can be chatting about where we're going. I can be pointing things out on the track. I'm not using 100% of my capacity to drive the car as fast as I can, but invariably I take someone out and they're all mortified. They think we're just about to crash at every turn. They think the car's totally out of control. They're getting dizzy. Their head starts bobbing back and forth. I come in, I'm like, "What? This was nothing." They go like, "Please stop the car." This was insane, right?

38:01

It reminds me every single time that this was how I felt the first time I was in a racing car. I felt like this. Everything was just coming at me so fast. I can't even think. Then you do it more and you get better. You develop your eye, you develop your reflexes, you develop your synapses such that they literally run at a higher clock frequence. When they do, all the inputs slow down and now it's easy. Imagine playing tennis with a Federer or something, but you slow down the ball 100 times. That's not a difficult tennis match. That's an easy tennis match. So much of learning is the capacity to slow down reality in real time just that you're no longer dealing with such difficult problems.

38:49

I think about this quote, "Don't wish for things to be easier. Wish to be better," and then work to be better because in almost all pursuits, in almost all domains, you can't be, again, you can't be the best in the world. Only one of those. It probably won't be you. Them are the odds, but you can become better and you can slow things down and you can increase your clock frequence.

39:12

You said that you should be stronger too. This is a real challenge because if the path to meaning is paved with responsibility, when is too much responsibility the path to unnecessary suffering?

39:41

That's a calibration you have to continue to make. It's entirely possible that you're trying to take too big leaps too soon. Happens all the time. If I had, as my second week of race car driving thought, "Do you know what? I should show up at the grid at Le Mans. I'm ready. I've done this for a weekend. How hard can it be?" I would've shown up to something not only would I have been unqualified, I would've been dangerous in the bad sense of the word, right? I could have put myself and others at severe risk when we were traveling 350 kilometers an hour in a race car in the dark while it's raining. Not something you do after a weekend's worth of practice.

40:24

But, at the same time, I could also have spent the first weekend going around the track and maybe the next weekend and the one after that, and then reached some plateau where I was just comfortable and safe. Then like, "Ah, this is good. I'm good here. I'm good for my local little track. I'm good for the competition that's just, whatever, within a short drive from Chicago." That, to me, felt like unambitious and not trying to let the difficulties of the world improve me.

41:00

Putting yourself in positions where you're constantly thinking, "Eh, it's a little too much, little too much." Not so much that you get destroyed. Same thing with training. I mean, I do a training program three times a week. I've done this on and off for a very long time. What I always find is if I've been off the wagon, so to speak, I haven't been training for six months or something and go back into the gym, if I just start reaching for that 20 kilo dumbbell and try to do the same moves as I did when I was really on it last time, I'll just freaking pop a muscle or something. I'm not ready. You got to work up to it.

41:40

But at the same time, if I'm at the gym and I just keep lifting the same thing week after week after week, I'm not improving. I'm not getting stronger. I'm not getting better. You need to be pushed. Most of the times you need to be pushed slightly beyond your comfort zone, slightly beyond your competence level because otherwise you're not breaking anything. You're not breaking your neurons, you're not breaking your muscles, and they won't rebuild stronger and faster.

42:08

But I think this insight about responsibility, it was actually one of these other things that was a real aha moment for me because I've often struggled with the sense of responsibility and often wanted to feel like it's a curb on my independence. If you're responsible for not just yourself, but a company and other people and so on, you can't just always do everything that you want entirely hedonistically according to your own whims and wishes. I've always thought about how can I escape that? Can I get out from under this responsibility?

42:42

The way you put it reminded me about how Jordan Peterson puts it. That if someone is deprived of meaning, you shouldn't make it easy on them. You should make it harder. In the sense of responsibility, that oftentimes this lack of meaning comes from a lack of responsibility. That it doesn't come from it being too heavy. It becomes from be too light. I find this too in terms of motivation and energy. I worked early on in my career at a number of companies where I, for long stretches of time, were uninspired. That I would go to work for eight hours a day and I would not be exercising the maximum of my capacity. I would not be stretching and reaching and firing my neurons in a way that would rebuild them faster. I was just plotting, or not plotting. That sounds devious. Just muddling through, and that muddling through I thought, "Do you know what? Work isn't super interesting right now. Work isn't super motivating, but then when I come home, I'll have all this extra energy."

43:48

That's not how it works. You can't save energy like that. In fact, you get energy by using energy. You get stronger by exercising your muscles. You get smarter by exercising your brain. It doesn't work to reserve it. I can't save the day. I was like, "Oh, I'm going to take it really easy today and then tomorrow or the next day I'm going to have that extra day." What? No. That day has passed. That energy just gets flushed. It gets wiped out. That sense of taking on responsibility, even when it's uncomfortable, even when you'd rather not is the source of meaning. I think for perhaps even most people most of the time, but it's such a difficult one to realize, particularly when you're starved for it. When you are in the dumps of it and there isn't enough and the energy is low, the last thing you think of is, "How can I spend more? How can I take on more," but that's exactly what you need to do.

44:52

It sounds similar to your flow state because you don't want to have none of it, but you also don't want to OD on responsibility.

45:00

Yes, and this comes back to also the way you learn. Don't show up to Le Mans the weekend after you started racing. Work your way up, but you have to keep progressing through slightly uncomfortable phases. "I don't know if I can do it." Great, do it. If you're sure you can't do it and you're like there's no freaking way. Okay, fine. That's not the right one, but it's the, "Ah, I don't know if I can do it." Oh, absolutely. You've got to do it.

45:28

When have you taken on something that was way too much and how did you learn that it was too much?

45:38

That's a good question because if I've over-indexed on anything, it's been the opposite, this steadfast refusal to opportunities, even when they seemed interesting or promising or whatever over a very long period of time. This commitment to just a handful of things I was going to both get good at and pay attention to. In that, has there been anything that's really clocked out where I've had to scale back? I don't know. If anything, I'm in that phase now because I've allowed all the automatic nos to become yeses for a period of time. I am feeling a little bit of that. That I've said yes to too many things over the past year-ish or something like that, which is great feedback because sometimes I got to feel like I got to run to the other side of the line to find out where the line is.

46:32

I had so long stayed in this very comfortable place of just anyone enticing me with any opportunity at all, I'd just say like, "Oh, yeah. Thank you for the opportunity, but no. No." Now I switched back a bit and thought, "What would happen if I said yes a bit more?" Then just started saying yes to a bunch of things. I had a ton of coffee meetings and all sorts of other things that I never in a billion years would have done before. I felt like there was something cool about that. But ultimately, now that I have actually overdosed on that, I'm absolutely going to pull back and go back to having this glorious calendar where there's nothing on it for an entire week. That is, in many ways, my ideal state because I find that my creativity is most easily provoked when I'm bored.

47:26

This boredom, for me, arises when there's nothing on the calendar for a whole week. I have to come up, in part, with a self-driven agenda for where I want to spend my time. I'll spend one or two days and I'll just clean everything up. I'll respond to all the emails that've been pending. I'll check everything. Then it'll be like, "Ah, okay." Now I've read all the stuff I'm going to read on the internet. I've answered all my emails like da, da, da, da, da. All right. Let me dive into some work. Then I get into something and then that's really meaningful and it's the things that push things forward and make the big leaps and blah, blah, blah, but I need that level of boredom. If my calendar is packed, I'm not finding any creativity.

48:07

It feels like those two parts responsibility and finding the time to be bored are on two different planes. How can you search for greater responsibility, but at the same time find the space to be bored?

48:21

That's a great dilemma. I think part of that dilemma comes from divorcing responsibility from busyness. A lot of people equate the two, especially when it comes to running a company. That responsibility means being involved with everything all the time, doing all the work that isn't getting done to your satisfaction of pace and urgency. Those are traps, both of them, that I fall in often. But I have learned to set boundaries around, for example, with things like a commitment to not working more than 40 hours a week on average. There are occasional weeks where I work more and then there are weeks where I work less. But if you take a whole year, it's about 40 hours a week.

49:09

You just can't do everything. Not only is there more than 40 hours a week of work that I could possibly involve myself in and feel like my responsibility perhaps some level obliges me to involve myself in, but there's also 120 hours of work a week. There's also 200. There's an unlimited amount of stuff that I could feel like, "Well, I should do that because I have the obligation to do that." Sometimes the responsibility that you hold comes with a serving of just sit back and shut the fuck up. Are we on a good path right now? Great. Don't mess with it. Don't tinker it. Keep your hands off. That's responsibility.

49:52

Now, this is one of the ways we've essentially institutionalized at 37signals with our way of working, which is something we call Shape Up. It's a software development methodology. You can read about it at Basecamp.com/ShapeUp. Its central thesis is that we work in six-week cycles. At the beginning of a cycle, we'll determine what we should work on. Once we start working on that cycle, we will work on the things we said we were going to work on and then we will otherwise sit on our damn hands. All the good, great ideas we're going to come up with, they're not going to just flow into the work right away. They have to wait until it's time to decide again. That level of tying your hand behind your backs in some ways, not being able to react on every gut instinct of urgency when you get a new idea of you hear a new idea, is a way to fuse responsibility with a reservedness. That responsibility doesn't mean just being hyperactive all the time, that these things actually go hand-in-hand. The best thing, and I still struggle with this from time to time, the best thing you can do for your team that you're responsible for is to leave them the hell alone. I like to be left alone a lot of the time. So you can combine those things and say like, "Do you know what? I'm going to step in with responsibility, be part of setting it in direction." And once the direction is set, leave the people to simply travel that direction and then spend the time between checkpoints getting bored, getting creative, coming up with my own damn stuff to do.

51:36

These narratives so clearly enable your work. What narratives have you held about yourself that might have worked against you?

51:53

Oh, there's so many. Well, I think I had a more... How to put it? Bat out of hell approach to things early on in my career. This drive to, I don't know, accentuate or affect change at my timetable in a way that clearly rubbed a lot of people the wrong way. It continues to rub people the wrong way. I don't know though, is it that something I regret? I try to again, embrace the amor fati. Embrace that you know what? I wouldn't have been this person getting to this place unless I'd done the things that I did. It's sort of a truism of that. I don't sit in a chair built on regret at all.

52:45

There are very, very few things that I regret in my life and not because I was always right. In fact, some of the things I cherish most were the things where I was wrong or had poor outcomes or whatever because it ties back to things we just talked about. Don't wish for things to be easier, wish for you to be stronger. And to get stronger, you have to at times make some mistakes that have consequences. And then just, again, this is just the way my brain integrates experiences. Choose to look back upon that mistake in almost all cases with a sense of gratitude. I'm really happy I got that wrong. What a great opportunity to learn more. What a great opportunity to pick a new course.

53:31

What a great opportunity to see the world in a different way through a different lens. I wouldn't have gotten any of those things if I wasn't wrong. Wonderful. I love being wrong because being wrong is a recognition that you still have something to learn. If I knew everything about everything, holy shit, life would be boring. What is there left to do is one of the reasons, again, I don't want to be an elf living to 2,000. I'd know too much about too many things. Part of the joy of life is the novelty of figuring out you don't know it all. Being puzzled, being befuddled, being embarrassed. Wonderful parts of the human experience.

54:21

What do you regret in your working life?

54:30

I mean, I accept the question in the collegial sense of regret, right? Because I don't actually accept it in my personal definition of regret because as I said, I don't regret anything. Now, are there things that were in the moment had consequences I did not foresee? And those consequences were hard or difficult? Oh, absolutely. All the time. But again, I look at those hard consequences. I go like, "Wow, that was great. What a gift to be able to have that." So no, I don't like to look at experiences in life through that lens. And if I try to, it's because I'm sort pretending to be someone else looking at my actions and their consequences and then trying to derive meaning from them under this paradigm. But it's not how I process the world, which again, maybe that's the big regret or others regret about my lack of regrets that this inability to just be filled with shame and regret. These are not emotions that I evoke or that even drift past my experience most of the times.

55:48

And I think this is perhaps just where people's dispositions are different. I keep reading about people being filled with anxiety and shame and regret and so on, and I empathize with that, but not from a position of I feel that too. And again, maybe this is just... I mean, we're all born differently and I'm happy and glad, and it's probably great for civilization that we're not all this. That we have members of the broad world who do experience greater degrees of shame and regret because that's part of the counter weighing balances that ensure we go in an overall good direction. But if anything, I feel like I see too much of it and I see too much of it holding back people who could have gotten further and better without that much of it.

56:43

It strikes me that there must be a relationship between your stoicism and the way that you don't feel that anxiety.

56:56

Now, it should be fair to say that I certainly have had moments in my career where there's been anxiety in them, but that's about in the moment. I don't have anxiety about past regrets or trying to replay in my head how could I done things differently or whatever. That's not how I process things. I only process them forward. But this sense of anxiety is certainly something I've had in my career. I mean, we've had times, for example, where things has been down for hours and hours where I go like, holy shit, this could potentially be a company ending event. If we can't figure out a way to get these servers back online, all the good will in the world is going to eventually burn off and customers are going to leave and we will have nothing. But as I experience that anxiety in the moment, I try to couch it against the practice that I've been doing for many years with negative visualization.

58:00

These is one of those core stoic practices that I hold incredibly dear, and I use it every week. It's negative visualization and it's about imagining all the worst things in the world that could possibly happen to you up front, process them in such a way that you're okay with the outcome. So let's take the services down and they stay down. We don't come back up, or we lost all the backups and somehow you can't recreate them. Whatever. The business is over, and let's just say it happens right now, November 7th, 2022. That would obviously be a monumental event. Plenty of people would call it catastrophe. I would choose to look at that as an eventual natural ending. This company's going to end either today, five years from now, 20 years from now, on the case of some Japanese family run businesses, a thousand years from now. Eventually it's going to end.

59:06

So the exact moment that happens, do you know what? I should not get too attached to that. What I should instead is to look back upon the fact that over the past 21 and a half years, I've had the time of my life literally running this company. What a great opportunity to work with some truly amazing people. To serve some customers who really got value out of what we had to offer, to sell them base camp, to teach them better ways to run their project, to sell them hey.com, to turn a loathing of email into a love of email. Wow, what more could you wish for? And now it's over and you're going to cry about that? Why not celebrate the 21 and a half years that you just went through? Or if it had happened 10 years ago, the 10 years when that happened, right?

01:00:00

Love your faith. Get comfortable with the fact that eventually bad things will happen. On a long enough time horizon, we're all dead. And keeping that front of mind, which is this other stoic principle of memento moiri remember death, really helps you... Really helped me, I should say, instill a sense of calmness about this or at least counterweight it because the anxiety arrives anyway. When the services are down, maybe you're... Or not maybe, my heart at times would beat hard or fast. I've used this sleep ring, the aura ring for many years, and whenever I've gone through something stressful at the company, I could see it in my sleep. You'd like baseline beats per minute of your heart, of my heart would just be higher. So I don't think, or I have certainly not arrived at a Buddha level sense of calm that prevents me from experiencing the in the moment levels of anxiety.

01:00:59

But I managed to counterweight that intellectually with this stoic belief and practice of everything from negative visualization to a gratitude for a life lift up until this point. This is what I also think was so often about where do you know what? I could have been born in the 1800s. If I was born in the 1800s at the economic level that I entered the world at. Holy shit, life would've been miserable in comparison to the absolute splendor and wonder that I grew up under, even if that was lower middle class or lower working class even in Copenhagen at the time. That we are almost all of us so eternally fortunate on the long arc of history to be here right now being us. So it kind of feels like, "Oh, that's just gravy again." Maybe someone will say, "Well, easy for you to say. You seem to have it pretty sweet. A lot of things worked out well for you. Congratulations. That's not the lived experience of everyone else."

01:02:09

And I'd go like, "Yeah, absolutely. No, it's not." Which is one of the reasons why I'm such a fan of stoicism is that it has found resonance with people at all levels of the hierarchy, from a slave in Ancient Rome to the emperor of Rome. It doesn't get much bigger than that, like the span of human experience. And through that, the realization that we're far more alike in how we process the world and how we deal with the world than we are apart, and that the material circumstances of our existence do not control how we choose to live life. Life is full of miserable billionaires

01:02:50

When it is all over, how will you calculate your legacy?

01:02:57

First of all, by not tallying it at all. I mean, caring about your legacy is caring about what other people think of you, which is in my opinion, a flawed place to do any evaluation of your life. You should look back upon your experience and see, did I live a good life? Was this life long enough on the last day? Do I actually have any of those regrets? Did I waste my twenties and my thirties chasing work? Maybe to the detriment of everything else? Did I miss the childhood of my children because I was stuck in the office? Those are the kind of things that I think could seed you with regret. I strive to die on the last day feeling content about the time I spend here on this little blue dot.

01:03:50

And what is David optimizing for at work now?

01:03:58

It's a good question. In many ways, it's the same thing I've always optimized for. The possibility of entering a flow state. I'm still addicted to the flow state. I'm still in love with Ruby, the programming language. I enjoy exercising that programming language often, frequently, and working the company and operating in such a way that we are respectful of the uncommon, if not outright rare level of independence that we have, that we should be doing all the things no one would ever give us permission to do. We should be saying all the things no one would ever give you permission to say. Things that wouldn't get a sign off through three layers of management. We are not beholden to anyone else in terms of a boss than ourselves and each other when it comes to Jason or I. And that affords us a level of freedom that we have an obligation to exercise.

01:04:59

So I'm always on the lookout for these kinds of opportunities to exercise that freedom, to do the kind of things that no one else, if not could, than would do. Now, that's not... I mean, there's all sorts of awful things that people won't do, but to exercise all the things they wish they could. Let's put it like that, right? Oh, I wish I could do that if only, but I won't because A, B, C, D, and E. That shrinkage of the incongruence that you talked about between who we are and what we do, I love fiddling at that, getting that as tight as possible, simply only working on the things we're deeply excited about working on, working in a way we're deeply excited about working and being accountable primarily to ourselves.

01:05:50

And not only... I mean, we're accountable to our customers and ourselves. I include our employees in that. But at the end of the day, for me to still go to work after 20 plus years in this business, and I know it's the same for Jason, is like, do you know what? First I have to put my own mask on. If I'm not breathing an oxygen that has a deep sense of meaning, satisfaction, if not outright or at least occasional happiness, yeah, we're going to go down, right? We are in the cockpit, so if we don't put on our mask first, we will go down. It's not the only mask that matters, but it is the first mask that matters. If we end up running a company that we fundamentally don't like or don't enjoy the day to day work of, it's over.

01:06:46

I so enjoyed today, David.

01:06:50

This is great.

01:06:52

Thank you so much, and thank you for being so personal and willing to go so deep.

01:06:58

It's the only thing I find interesting these days, right? Why talk in just the airy platitudes? I've said plenty of them. Now what's left is to talk about things that actually fucking matter.

01:07:14

Love it. Thanks so much, David. That was amazing.

01:07:16

Yeah, that was a pleasure. All right, man.

01:07:17

All right, man.

01:07:19

Thanks, Ben.