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Greetings from Mojito Island

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Basecamp co-founder and CTO David Heinemeier Hansson has been on a not-totally-intended sabbatical from both work and Twitter, and on an entirely intended break from living in the U.S. He checks in from Europe to talk about how he’s managing his time off as the boss, and what developments back at Basecamp briefly pulled him back into work.

The Full Transcript:

[00:00:00] Broken By Design by Clip Art plays.

Shaun: [00:00:01] Welcome to Rework, a podcast by Basecamp about the better way to work and run your business. I’m Shaun Hildner.

Wailin: [00:00:07] And I’m Wailin Wong. Shaun, have you noticed Twitter has been like a little quiet lately. Almost too quiet.

Shaun: [00:00:15] No. Twitter is still a garbage fire, Wailin. But I think I might know the reason for the absence you’ve been feeling. There has been a significant lack of David Heinemeier Hansson.

Wailin: [00:00:25] Oh, that’s what it is. For the last six weeks, Basecamp’s CTO, David Heinemeier Hansson, has been on sabbatical. We’ve heard barely a peep from him around here and what seems like ages.

Shaun: [00:00:35] And for reasons we’ll get into in this episode, David hasn’t been able to work for weeks. But I recently managed to catch up with him half a world away to talk about taking time off, company emergencies, and esoteric Danish commercial law.

David: [00:00:50] I am actually in Berlin right now.

Shaun: [00:00:53] How did this work out?

David: [00:00:54] It worked out the sabbatical was not really, A, I want to do a sabbatical. It was, hey, I want to go to Denmark, because we had just been in lockdown for five months. The kids had been out of the house, I think maybe five times in five months, I mean, not out of the house, literally, we have a yard. They’ve been out in the yard, but they hadn’t gone places, essentially, more than about five times, five, six times over five months.

Shaun: [00:01:19] Or like seen other human beings.

David: [00:01:21] There’d been a very limited amount of seeing other human beings. I think like three times seeing other human beings, maybe. But that just felt like it wasn’t going to end. What actually settled it for us was our school was planning to open. And then we got the notice, we’re not opening. And we’re like, we’ve just gone through five months of this, can’t. Well, not can’t. You can, you can do a lot of things. Humans are resilient creatures who can learn to live with a lot of things, but we didn’t want to. We didn’t want to live with another X unknown months of isolation, essentially.

[00:02:00] I mean, again, we really should not complain. But even if you have the nicest place to be under house arrest, and Malibu is a very nice place, the weather’s… well, was good. Now, there’s also the wildfires to throw in. We kind of missed out on those. But prior to that, it’s very nice place to be under house arrest. But house arrest sucks. I completely understand the impulses and the rebellion against that, because it really sucks. That doesn’t mean it’s not necessary and it’s not the right thing to do. Those things are all true. But we have an opportunity, given the fact that I am a Danish citizen, and so are all the three kids and Jamie, my wife can hop on board that train and we could go to a place that wasn’t like that. That was not under house arrest, right?

[00:02:48] Denmark, in March, had a complete shutdown. For I think about six weeks, where, like, all the streets are empty, nothing is happening, complete shutdown. And that worked, surprise, surprise.

Shaun: [00:03:01] And just six weeks.

David: [00:03:01] And it took six weeks. In fact, most of the schools, they were closed for one month, and then they they started opening back up. So a very different approach to handling a pandemic than what was being rolled out in the US, and it meant that society was impacted in a very different way. And in particular, for families, this whole thing of kids just being home for five months was not was not happening there. Kids were home for about a month and then they started filling in. I mean, some cases a little longer, but in all the cases much less.

[00:03:39] So, we thought we’re not gonna miss anything. Right? Like we have this opportunity to do this, go live in Denmark for a little while or a longer while, as we’ll perhaps see. But what are we going to miss? We’re gonna miss homeschooling. Okay. Not a big miss, as of five months, however, limited fun that was in some regard.

[00:04:01] So it just seemed like this was something we should do. So that’s what we did. And then the complication came in. For a variety of reasons, I couldn’t work in the period of time when we’re in Denmark. So that’s all of a sudden forced, like, okay, I also got to take a sabbatical.

[00:04:15] If you are a executive at a American company and you also happen to be a Danish citizen. And you then move to Denmark, and you do work as an executive for this American company, this American company creates nexus in the country, which essentially says like, this is now partly a Danish company, which has a ton of ramifications in all sorts of things, from legal structure to taxes to whatever, whatever, whatever. And that was just not a reasonable thing to do. I wanted to take my family to Denmark.

Shaun: [00:04:49] Don’t want to take my company to Denmark.

David: [00:04:51] Exactly. Yeah, to some extent was not the best timing. It also wasn’t the worst timing, right? Like we had just gone through this exhausting launch of HEY.

Shaun: [00:05:01] Yeah.

David: [00:05:01] Where I’d worked, I don’t know, 14 hour days for two weeks or something. And I was feeling the after effects of that, feeling pretty worn down. And also, it’s been 20 years for me at Basecamp. And usually employees at Basecamp are eligible for a sabbatical of one month, every three years, and I have not taken a single one in 20 years.

Shaun: [00:05:26] In 20 years.

David: [00:05:26] So I thought, like, you know what? I kind of worked up some credit here.

Shaun: [00:05:30] I’ve earned this one.

David: [00:05:32] It wasn’t entirely of my choosing in terms of the timing or how it was going to happen. But it felt like this was an acceptable, “sacrifice”. I mean, that even sounds conceited. But we were going to do this as a family. This was what was required to make that happen. And okay, then let’s do that. And I’ve been on a sabbatical for the past, what is that going to be like, five weeks now, six weeks, almost maybe? Which has been interesting, really, because I kind of I pulled the plug on everything at once. I pulled the plug on work, I pulled the plug on the US. And I pulled the plug on Twitter.

Shaun: [00:06:12] Wow.

David: [00:06:13] Which, all three factors at the same time. I mean, they played a pretty large part of my life, obviously. And I kind of just yanked it all at one time. And we went up to Denmark, I didn’t open my laptop, I didn’t check Twitter, I didn’t do any of these things for a long time. And that was really nice, at least for a good portion of that time. And now I’m getting to almost the stage that I’ve been warning entrepreneurs about in regards to selling your company.

[00:06:48] Okay, so you’ve been sitting on mojito Island for six weeks, and just relaxing, kicking back not doing anything, really. I mean, I’ve been doing stuff, but I haven’t been working. And you get to the point where you’re like, okay, this can’t last. I got to do something. It’s one of those things where like, it’s not bliss, either, to just kick up your feet for unlimited amounts of… For the first two weeks, in particular, it was just like, maybe even three weeks straight, it was just fucking wonderful not to open a Twitter feed, not to have anything to do with work, not to be in the US, to kind of just like, isolate fully. And you could almost just… I could feel the battery recharging. Every day, you’re just feeling a bit better. And then you get to, I mean, probably not 100%, but you get to 80% on your battery. And you go like, okay, I’m ready to do some stuff.

[00:07:43] And, and then the situation is just for right now, I’m still on the sabbatical. This is the conditions of being in Denmark for a bit, that just can’t work while in Denmark. Trying to figure out where that’s gonna go and set that up in such a way that that can happen. But it just takes a little while.

Shaun: [00:08:02] You told me off the air as we’re trying to set this up, that you had been really good about not checking in at work. Did you delete Basecamp from your phone? Have you not been checking emails? How have you sort of, especially at the beginning of your sabbatical? How did you manage to unplug that well?

David: [00:08:18] It was much easier than I thought. In fact, I thought since we’re using HEY for Work with Basecamp, I thought I was just gonna get like a barrage of emails. But I unplugged from the Basecamp Daily Recap, such that I didn’t get any of that. And I designated the programming work, the GitHub notifications and so on to the Paper Trail. Then I just didn’t open the Basecamp app. That was it. It wasn’t that hard. I thought—I actually, I thought when we were about to do it, I thought I had to do more technical stuff. I thought I had to disentangle the the Basecamp account and my HEY account. And it turned out it just wasn’t necessary. I filed everything that I got that was work-related, which wasn’t that much because I announced this quite broadly that, hey, I’m off. Don’t bug me. Unless it’s a fucking emergency.

Shaun: [00:09:06] Right.

David: [00:09:06] Which we have one of, we had one fucking emergency. And I’m like—

Shaun: [00:09:10] We’ll get to that.

David: [00:09:11] —back on an emergency for that. But for everything else, it just, it was easier than I thought, actually. It’s just that you get to the point, as I said, where your batteries are recharged. At least for me that that’s about the amount of time it takes. It was funny. Just when I kicked this off the School of Life had an article about the existential dangers of taking extended amounts of time off work. It was funny because it really hit spot on and it is one of those things when when you don’t have work or something else that engages your being for eight hours a day or whatever you have a lot of time left over to think about the state of the world and your place in it and that can be challenging.

Shaun: [00:09:57] Especially right now.

David: [00:09:59] Yes, especially right now, where you just—

Shaun: [00:10:00] Spending all that brain energy on the state of the world sounds awful right now.

David: [00:10:06] In some ways, I think it is, right? It is not this paradise like, that’s the whole narrative that we’ve been trying to tell other entrepreneurs who are like, Oh, I should sell my company, because then I can do all the things I really wanted. Yeah, you know what, some people that works, and they do it and they find a new calling. And that really occupies them. And then for other people, they just lose the thing they have, and then they’re left with not enough, right?

[00:10:30] It’s not that you can’t have things in my day, I have plenty of things in my day, it’s… you can make 16 hours pass. It’s just that there’s, for me, and the kind of work that gets me fired up, there’s not enough. And I think the other factor of this was just, it’s… even if you’re working remotely, even if you’re not seeing each other, it’s fun to work with other people.

Shaun: [00:10:52] Yeah.

David: [00:10:53] And I’ve definitely missed that. I missed being part of a group of people working on something that fires all your capacities at one time to do stuff. So this is, in many ways, it has been a reaffirmation of everything we’ve been talking about for the past 20 years about having some balance in your life, right? I felt like I really needed the three weeks break after launching HEY, because we had just run so far into the red for quite a long time, that it was just exhausting. I was exhausted. There’s not enough left in the battery. And then you go through the process, and you recharge and you get back up and you’re like, it’s not balanced either not to have any work, at least for me. And the things that I like to do, right? I’m not in balance, when I just do the things that humans do when they don’t have work. It’s not enough, and you end up missing it and actually creates a lack of balance.

[00:11:57] So anyway, I fully understand how plenty of people would perhaps love to experience what that is like, “Oh, I have too much free time. How awful. That’s a—”

Shaun: [00:12:06] Yeah, what a problem to have.

David: [00:12:07] Yeah, what a problem to have, I completely understand that. But it’s also one of those things I remember seeing before I jumped off Twitter, there was a thread about, again, awkward connections here. I think it was about Jeff Bezos and someone making the connection of like, dudes, the richest man in the world. If I was so rich, I would just quit my job and do nothing. Right?

Shaun: [00:12:28] Sure. Yeah, you hear that a lot.

David: [00:12:30] You hear that a lot from from people who like have a desire to like, “Oh, man, if I could afford it, I’d love to just do nothing all day.” And it’s one of those things that I think, for most people, is an unexamined knee jerk reaction that would pan out very poorly. Right? It’s one of those things that feels like a thing you should say about people who can afford to do it. Right?

Shaun: [00:12:55] Yep.

David: [00:12:55] When you wouldn’t actually want that. Work does provide a deep source of meaning for a lot of people, perhaps even most people. Certainly not all people, I know plenty of people are wired in a way where they don’t need to work to find meaning. And in some ways, I’m envious. And in other ways, I’m not. Like, it’s not like this is such a cross to bear that I like to work. I like to express my potential and faculties in pursuit of making things. This is not a bad thing. The game or the setup, for me at least, is to find that balance where you’re doing the work because you like to use your capacity to make things. And then you also do other things, right? Essentially, what we’ve been preaching for the 20 years about, HEY, 40 hours is enough. But zero hours is too little. At least that’s how I come out at it. Even 10 hours is too little for me. 20 hours, probably, too. About 30 to 40 hours a week. That sounds great.

Shaun: [00:13:57] Mm hmm. So what is the perfect length of vacation for you? I’m sure this is different for everyone, and you know, this is something everyone has to dial in. But two weeks was great. Three weeks was great. Six weeks is too much.

David: [00:14:08] Yes.

Shaun: [00:14:09] Have you sort of nailed down the perfect amount of time away?

David: [00:14:13] I think for me to just go a place and be a place and not do anything like 10 days to two weeks is enough. That doesn’t mean you can’t take more, do vacation and just like sort of hang out house or whatever. Three weeks, then I’m definitely at my limit. By week four, I want to start doing things again. That’s for sure.

[00:14:34] Which is interesting, because it also maps very well that we talked about Basecamp has this idea of the sabbatical, one month, every three years, right. At one month mark, I think it’s actually it’s a pretty good portion. Again, it maybe—

Shaun: [00:14:50] It seems to fit for most people, right?

David: [00:14:53] Yeah. A lot of the feedback that I’ve heard from people coming back from sabbatical is, wow, that was really great. Now I feel like, as I explained, that I’m recharged and energized. And also, I’m kind of eager to get back to work.

Shaun: [00:15:07] Yeah, yeah. Well, you had to come back to work a little unexpectedly. Can you tell me about that?

David: [00:15:13] Yeah. So, I think it was about… I mean, as we talked about, time is this weird… It’s like last week or two weeks ago, maybe, something like that.

Shaun: [00:15:21] Four weeks into… three or four weeks into your sabbatical.

David: [00:15:24] Right. I don’t really set up that like, hey, try not to bug me.

Shaun: [00:15:30] Do your best.

David: [00:15:32] But if there’s an emergency, I mean, I’m gonna come. I’ll help. Right.

Shaun: [00:15:37] Yeah.

David: [00:15:37] I’ll come back. And I’ll help. And then we kind of had an emergency. And we had a series of short-ish outages, but not short enough, right. Like they weren’t two minutes, they were more like 15 minutes or 20 minutes.

Shaun: [00:15:48] Let me jump in for one second to let you know that if you would like some more info on these Basecamp emergencies, check out our episode from September called Something’s Broken. Okay, back to David.

David: [00:16:00] On the second outage, I’d already texted with Troy about, like, do you need my help? Do you need some assistance? Should I come back here? I noticed the—I still get the SMSes. So that was the thing. I hadn’t actually turned those off. So the SMSes we get a Basecamp is, hey, there’s a problem. And it blasts out anyone who’s on the list. And I was I was on the list. So I got the SMSes, and the first time I was like, they got it. All good. Then the second time I got one of like, I better just have a quick look and check in if there’s any ways I can be helpful with this. And then when we had the third thing, I was just like, okay, I’m just gonna come back for a day. It’s not a big deal. I’m not sealed into some box I have to break out of. It is literally just I have a computer and I can open it. It’s not that big of a deal. So I came back for one day. Well, not even a day. An evening, to help sort out some issues that we had and help us think through and work through some of those problems.

[00:17:07] And then I went back like the very next day and like, alright, call me again, if things are burning, and I’ll come back to help, but otherwise, I trust that you all got it. And they did.

Shaun: [00:17:16] I’m surprised that you can sort of switch your brain back off after that so quickly. Like it sounded like it was easy for you to get back into sabbatical mode.

David: [00:17:27] Yeah.

Shaun: [00:17:26] You know, after one day of work.

David: [00:17:30] I’d say that was pretty easy. Partly because it wasn’t so much about it being a technical thing, it was more about being a confidence thing. I just want to know, like, hey, I hadn’t been in it, right? So I didn’t know what our deliberations were.

Shaun: [00:17:42] Sure.

David: [00:17:44] I just saw the effects. And I’m like, I just want to have confidence that we got this.

Shaun: [00:17:48] Well, now you’re in a hotel room in Berlin, working for at least part of the week. What spurred that on?

David: [00:17:57] This was actually the plan from the get-go. Where I was like, hey, I’m going to take three months off for this sabbatical. But I’m going to try to check in once a month. It turned out to be a little longer than that before the first check in. And originally the plan was, I was going to go to Spain, and spend some time there. And then this pandemic is spoiling plans left and right. There’s a surge in Spain, and that can happen. And that Germany is pretty close. And like, hey. Let me let me spend the little week in Berlin. And then I’m not in Denmark and I can do some work while I’m here and just catch up on some things, just so that there’s not a complete mountain afterwards. And also, just as we talked about, like hey, after six weeks, it’s it’s not an imposition. It’s actually a bit of a desire. I’d like to check up on some things. And we are working on HEY for Work. And the team has been working on getting all that ready. And there were a couple of knots in the architectural debates about which way we should go where I could be helpful. And came back and we had some good discussions about that and unblocked some paths we could take. And that felt good, too, to engage your faculties again on something that matters and something I’m really excited about that we’re going to launch and we promised to do this year and all these other things. So, yeah.

Shaun: [00:19:22] You posted this morning about this issue of interrupting people because of the massive amounts of HEY bugs. Was this something you were thinking about while on sabbatical? Or when you came back, were you like, oh, wow, this is a problem that’s happening right now and I need to address it.

David: [00:19:41] This was when I came back. Over the past few days I have basically been having, I wouldn’t say like all the FaceTime meetings I would have had over a month but like maybe half of them compressed into a few days. So I got to talk to—

Shaun: [00:19:56] Well, thanks for coming on the show, David.

David: [00:19:59] I got to talk to most of the people who report to me, and it was just clear that this was one of those things that was hanging in the air that’s like, hey, we’re working on HEY for Work. It meant that there’s still some bugs in HEY we need to fix. There’s some bugs in every piece of software we’ve ever made since the… There’s bugs in all software, right? And we just needed to—

Shaun: [00:20:20] Not just us, come on.

David: [00:20:23] Yeah, exactly. We needed to just have a little bit of a institutional reminder of that. I think, oftentimes when you work with conscientious people who really want to make great software, bugs can take on almost like a personal moral failing, right? Like, oh, we let someone down because like the software didn’t work like they expected it to work, or how we designed it to work. And that feels really bad, because we want to make great software. And we want people to feel good about using software that doesn’t have bugs, right? So there can be this sense that the most important thing always is to fix bugs, which we’ve just for a very long time have rejected that notion. I think in Getting Real, even, from 2006, we have a chapter that says bugs are not special. Which essentially, is a bit of an overstatement. Some bugs are special, the kind of bugs that will destroy all your data, and so on, they’re pretty special. But most bugs are not that. Most bugs are annoyances or dead ends, or things that don’t render right or things that just like, don’t quite work right under certain edge case conditions. And you can essentially, if you have a sufficiently complicated system, which is almost all systems, certainly all sort of SaaS systems, certainly an email service that’s tried to do as much as HEY, does, right, it’s going to have an unlimited amount of that, right?

[00:21:45] At some point, you’re gonna get to the long tail end where the things that are bugs are really very, very minor, but they’re bugs nonetheless. And you could be working on that forever. You can’t run a software company like that. You have to be able to balance the fact that you should be fixing issues and continuing to improve the quality of your software. But you can’t gold platinum and overshoot on everything either. Right?

Shaun: [00:22:09] Right.

David: [00:22:09] If you do that, you’re not going to be spending any time making new features. And for a lot of customers, you might have something that’s an issue that affects, I don’t know, 50 people, right? The other 30,000 people, they’re not affected by that. But they are affected if you introduce a feature they’ve really been clamoring for, right? You make 30,000 people happy, versus making the 50 people who had this hit this edge case happy.

Shaun: [00:22:36] Like a really low stakes version of the trolley problem?

David: [00:22:40] Yeah, it’s just that you got to realize that it can’t just be all about that. And to realize that and to internalize that realization has to be that bugs are not moral failings.

Shaun: [00:22:52] Yeah.

David: [00:22:53] And this is one of those things that programmers themselves actually end up often reinforcing that, like, they apologize for bugs. And as a general approach, I don’t think that’s healthy. I don’t think programmers should be apologizing for bugs. This is a natural side effect of making software. If you make software, you will be making bugs. Now, of course, there are things where you feel like, oh, I should have known that, right? But you can end up being so self critical that you take it on as a moral failure, which is just not healthy.

[00:23:27] And part of this is because bugs are such a concrete example of like, okay, you could have done better. Do you know what? That’s in all—like customer service. Every customer service person will send out replies with bugs. If you define bugs as like, hey, we could have done this better, right? You could phrase this better, you could have spoken to the customer in exactly the right arguments that really would resonate with them. Everyone has bugs, like imperfections, in their work. And those imperfections are part of what makes us human.

[00:24:01] And in software development, those imperfections often get expressed in bugs. So we just got to take it as, hey, this is what it takes. This is what software development is. So what we were doing was just resetting those expectations. In particular because we had been in this mode, right after the launch of HEY, where everyone who was working on a technical level at Basecamp. They’re were all just mostly on [unclear], right?

Shaun: [00:24:20] Right.

David: [00:24:24] When you launch V1 of anything as involved as something like the HEY email service, it’s gonna have a ton of issues when you launch it. Tons of things you hadn’t figured out. And for eight weeks, I think, we just attacked those things like the top issues, the things that were mangling data or rendering them wrong, or a bunch of these things that were really impacting a lot of people and we took the top of all that and then we still had a long list. And then we said okay, we also got to move forward on some of the other commitments we’ve made. When we launched HEY, in general, number one thing was can I use this for work?

Shaun: [00:25:01] Right?

David: [00:25:02] Right. I really like the thing you made, can I use it for work? And we made the same mistake we’ve made a handful of times over the 20 years Jason and I have been making software together. We made public commitments. Which is the absolute worst thing you can do as a software company, because it is so easy and cheap to say you will do something in the future. And it’s such a source of regret when you run in against that. Because actually, if we had to do it again, perhaps we would have stayed on, polished things a little bit longer, in some cases. I don’t know, maybe not even, but it would have been nice to have the option. Right now, we do feel a little, like, hey, we said we were going to do hate for work this year, which is going to bring custom domains and these other things in there. And it’s gonna be the end of the year, pretty soon. So we kind of have to be working on that. So that’s what we switched over. And now we’re just realizing, okay, some of these bugs that are getting getting reported, they’e just gonna have to sit for a little bit.

[00:25:57] Again, if they’re critical, or they’re destroying data, or they’re mangling things, that’s a different matter, and we will get someone on it. But as we talked about, the majority of bugs are not that and that majority of bugs will go on to a list, someone will assess them and make sure they know the criticality and the scope of it. And then we’ll fix it at a point when we’ve gotten HEY for Work out.

Shaun: [00:26:18] So what is next? You have a two and a half more months of sabbatical, or sorry, one and a half more months of sabbatical. You spending the rest of the time back in Denmark?

David: [00:26:28] We’ll see how the exact timing goes out. I’m working on a setup where I can actually stay in Denmark for much longer. A set up where we create a Danish subsidiary that can be responsible for employing me and whatever else we set up in Denmark and could do some work from Denmark under the established rules for how that is supposed to work and paying proper taxes on that part of the work and so forth. And once that’s in place, I’ll be able to work from Denmark and do development for Basecamp again.

Shaun: [00:27:02] Well, I think that just about does it. It’s been really great to talk to you again, David.

David: [00:27:08] Likewise.

Shaun: [00:27:08] Again, it feels like it’s been a couple years, but I understand it’s only been five weeks.

David: [00:27:13] Yeah. So after this trip to Berlin, I am about to go back into sabbatical mode at least until the middle of October when I’ll then check in work again, so.

Shaun: [00:27:22] Yeah, I’ll see you in another few years in October.

David: [00:27:27] Exactly. Another two years collapse into a month.

Shaun: [00:27:29] All right, David. Thanks again for doing this.

David: [00:27:30] My pleasure.

[00:27:33] Broken By Design by Clip Art plays.

Wailin: [00:27:35] Rework is produced by Shaun Hildner, and me, Wailin Wong. Music for the show is by Clip Art.

Shaun: [00:27:40] You know what? We also haven’t heard from Basecamp CEO Jason Fried in ages and certainly plan to rectify that immediately. So this week, we’re bringing you a twofer with a special bonus episode in a couple of days.

Wailin: [00:27:52] David is on Twitter at @dhh. We are on Twitter at @reworkpodcast and you can find show notes for this episode at our home,