SEASON 2 - EPISODE 0056 - MAR 22, 2023

Taking a Sabbatical as a Business Owner

In this episode of REWORK, Jason Fried and David Heinemeier Hansson, co-founders of 37signals, join host Kimberly Rhodes to discuss the power of taking sabbaticals as business owners.

Jason recently returned to work after taking his first sabbatical in nearly 23 years. He and David share their experiences and insights on the benefits of taking extended breaks from work.

They cover the challenges of stepping away from a business you’ve built, the importance of trusting your team to handle things in your absence, and the value of returning to work with a fresh perspective.

Listen in to hear their practical advice for business owners considering taking a sabbatical and the positive impact time away can have on both individuals and the company.

Show Notes

00:43 - Jason shares why he took his first sabbatical in nearly 23 years and how disconnecting completely from work gave him a new perspective.
01:49 - David shares his forced sabbatical experience when he had to move to Denmark. He shares his opinion that it’s healthy for the organization’s resiliency to have its founders step out.
04:41 - Why feeling like you can’t take a vacation is unhealthy.
05:46 - Disconnecting during a sabbatical: Jason shares his experience that portrays the importance of taking time off and what he did during reentry to avoid overwhelm.
08:08 - David emphasizes the importance of taking a REAL break and trusting others to carry on, so you can return to work with a clearer mind and a better perspective on what truly matters.
09:57 - Jason shares why, if anything had to wait for him to return to be decided, it might be a symptom of overreliance on any one individual.
10:30 - Kimberly shares why there’s usually a scramble to get things done before a regular vacation and asks how preparing for a sabbatical differs.
11:27 - Jason shares the writing he did before taking off.
12:23 - David shares his realization that there are big foundational tenants of how they work that will stay the same, even if one of the principles is out for an extended time.
14:00 - Shifting the work to get projects where more people can independently drive them.
16:38 - Don’t fear the sabbatical: remember, you are not as important as you think. Jason advises people to trust their team.
17:53 - The importance of enjoying boredom: David shares how sabbaticals allow the mind enough space to work on the business in your head and remind you why you do what you do.
19:47 - It’s time to answer those questions! Kimberly announces that next week’s podcast episode will answer listener questions. Leave your voicemails at 708-628-7850 or send an email with questions about a better way to work and run your business.

Links & Resources

Do you have a question for Jason and David? Send us an email or leave us a voicemail at 708-628-7850.

Transcript

Kimberly (00:00): Welcome to REWORK, a podcast by 37signals about the better way to work and run your business. I’m your host, Kimberly Rhodes. A few weeks ago I sat down with 37signals’ principal programmer Jeff Hardy, to talk about the power of time off and how taking extended breaks from work can make you more productive and effective. Today I’m back with 37signals co-founders Jason Fried and David Heinemeier Hansson, to talk more about this concept of taking time off, but from the perspective of a business owner as Jason recently returned to work after taking his first sabbatical in nearly 23 years. I have questions for you both, but I think the first place to start Jason with is with you. We know you love sabbaticals or the concept of it for your team. Why, why did it take you so long to take yours?

Jason (00:43): I don’t know. I mean, it’s sort of embarrassing and irresponsible, frankly. I mean, for everybody. Like you gotta set a good example, first of all. And second of all, I probably really needed to take one. Um, so anyway, can’t change what happened. Here we are. I just took one and it was, uh, really worth it. So it reminds me of how valuable they are and, uh, how often we should be doing them. And it kind of actually made me think, uh, I’m probably gonna get myself in trouble, but that they should be a little bit longer than four weeks. So I think we have a, a four week policy, uh, every three years. Four is a little tight. Six might be better, but that’s not a decision, just saying out loud. Um, but anyway, it was, it was very valuable, mostly just to disconnect. I, I mean, what I did almost didn’t matter. It was just that I didn’t work at all. I didn’t check in at all. I didn’t do anything at all that had to do with work. And it was reassuring that the company can run without me as I knew it could. But it’s good to see that it does or it could even better perhaps in some areas and just to, you know, clear your mind and, and, uh, come back to work with, uh, with some fresh perspective.

Kimberly (01:43): So David, what’s your sabbatical history? I mean, have you taken sabbaticals since founding this company?

David (01:49): I had a forced sabbatical, uh, about two years ago, two and a half years ago when we moved to Denmark for a variety of, uh, tax and organizational reasons I couldn’t work while in Denmark for about two months, and that basically meant, uh, a sabbatical because, um, if I couldn’t work then I was going to be out anyway, I knew it was coming. So I set it up essentially as a sabbatical and it ended up being about the same time, about six or seven weeks. And what’s so funny about the, the six weeks is I felt exactly the same thing as Jason at four weeks. I was like, no, I could do this a little longer. And then interestingly enough, exactly at six weeks I’m like, okay, now I’m bored. Now I want to get back to stuff now I want to get back into it.

(02:37): So there is something magical right around that time, I think. But I also just really enjoyed it and I thought, as Jason said, it’s so healthy for the organization to have the founders, the executives step out of it and just like, okay, well you gotta make your own decisions now. I’m not here to answer your stuff. You have to figure it out. And of course you can, but you need the opportunity to really prove it. I think both to yourself, to the rest of your organization show that resiliency that you know what, the ship runs just fine without us, which is a general point I think is sometimes difficult for all employees, including Jason or I as sort of employees of the company that, you know what, everyone is kind of replaceable, at least on a relatively long basis. Do you know what if I had taken six months sabbatical instead of six weeks, it probably also would have been fine.

(03:37): And this comes back to what is actually the differential value that, that someone like Jason or I bring to the table, the kind of decisions that only Jason or I can or will make. They are and certainly should be very rare. They are the Titanic big shifts where Jason’s like, okay, I got a new idea for a product, um, that comes in as a, a full vision. And then boom, we go off work on that and that’ll take years. Like the last time Jason had a fully formed idea for a product was four years ago. I mean, that’s when we started working on Hey. And I think for example, my involvement with our cloud exit, if you thought of like, when was the last time I took a major CTO kind of decision on that, it was probably getting into the cloud like six years ago. So I think that’s just good and humbling to know all the way up and down the chain. Like regardless of what you do, if you are not replaceable for at least six months, something is not right. The organization is actually misconfigured.

Jason (04:41): Especially at our size. I mean, it’s, it’s a bit different of course, if you’re four people, right? So someone who’s listening to this as a three or four person company and you only have one programmer and that programmer’s gone, like, that’s a different story of course. Um, I just wanna kinda round that out because people always find those examples like, but what if, you know, fair enough. But yeah, we’re, we’re 80 people now and one of the reasons we’re 80 people is to have some redundancy, to have some slack in the system, to have some space so people don’t feel like they can’t step away for a bit because that’s actually the, the, the heavy part of it was when you feel like you can’t leave for some reason or you you can’t take a vacation for some reason, that’s an unhealthy position to be in. So even if you don’t take one for whatever reason, feeling like you can’t is far worse. So we wanted to make sure that, uh, that we had some room and um, we do.

Kimberly (05:31): Okay. So for both of you and Jason more specifically for you, since it’s so recent, did you have a hard time disconnecting when you were leaving? Did you unplug everything, disable every app that you had, and was it hard to come back?

Jason (05:46): So for me it was not hard to disconnect at all. Um, which probably means I’ve been craving that for a while and I finally got it. I basically, what I did was I, I didn’t take anything off my phone, but I, I don’t have notifications on anyway. Uh, the only notifications I have on are for Basecamp for pings, basically. And uh, at mentions I think is the option. So, um, I turn that off, that part of it off. Otherwise though, I don’t get notifications on my phone. I don’t have my badges on. I check things whenever I would normally want to. So that’s kind of how that happened. So that still wasn’t really much of a change, but I did, you know, have to break the instinct of like going to see what’s going on, but it really wasn’t hard. It, it really wasn’t.

(06:24): Um, it was just, don’t do that. I’m not gonna do that. Um, I did check Basecamp about three or four times during the six months to erase my, uh, Hey menu because my, my or my, my notifications in the app we’re gonna get super, super, super, super long. I just wanna reset them a few times. So they didn’t get like ridiculously long. David never reached out. Elaine never reached out, nobody reached out, which was really nice. So no one pulled me back in and I just did other things. It was very nice. In fact, I barely opened the computer. I mean, one of my little fantasies is like, if I ever stop working on computers, I would not open a computer for a year. Like I, I don’t need to open the computer like to, to do my day, you know? So I kind of did that for six weeks.

(07:05): I mean, I looked a few things up here and there, but mostly, uh, I didn’t use the computer at all, which was really nice. Um, and uh, it, it was, it was not hard. And coming back though, I did start to feel that itch, like David mentioned like about a week prior, I’m like, I’m getting bored. I’m finally getting bored. It’s good to be sort of bored for a while, but now I’m too bored. And so I was excited to dive back in and uh, one of the things I did though was I, I did some catch up, but I didn’t try to go back and read up everything I missed. That’s just sort of a ridiculous thing to do. I just kind of jumped in and there’s some things that some people brought to me or that I kind of had seen that I looked at more closely.

(07:41): Um, but uh, I did not try to catch up from day, the day one I missed. I basically just kind of hit the ground running and whatever happened without me was, I didn’t need me anyway. So don’t involve yourself, don’t jump back in. And the other thing is that you’re gonna find out what was important anyway, you know, in a few days or in a week or so. And that’s great. So that was another technique. I didn’t, uh, uh, I didn’t do that. I did check in with people, catch up with individuals, but I didn’t try to read up on everything I missed.

David (08:08): I think that’s the key leap of faith you have to do if you want a real break. This is actually something I’ve heard even from people just taking vacations that the reason they check in on a daily basis or semi-daily basis while they’re out is such that they don’t have to do the whole thing when they come back. But that’s just such a broken notion. I mean, how are you going to have any time off? If you have to constantly catch up on all of it, then you’re just taking that work burden and saying like, okay, I’m not doing it for this week, but then I’m gonna add it on to the week when I’m back and think about that with six week add, six weeks of catch up on top. I think that’s a real leap of faith that shows that you trust your organization and that happens at all levels.

(08:50): It’s not just about executives taking time off, it’s just as much about in your team. You trust the rest of your team to carry on, make good decisions and, and move on with things. And I think the thing I’ve found coming back after six or seven weeks was just what a relatively low number of things I needed to know and the things I needed to know, I would catch up as Jason said, with someone on a one-on-one or otherwise it would bubble back up. There’s like a handful of things maybe at most over the course of six weeks, which was again, another reminder that so much of all the busyness that we feel at work all the time, even for us and, and we are quite good, I’d say at cutting that out is self-made. It’s invented. It is because you want to keep up on everything all the time with everyone and know everything that’s going on yet it adds very little value. There’s, you just don’t need to know. There’s so much of the work where you just don’t need to know. You can trust the people working on it, making sound good decisions and just forget about it.

Jason (09:57): The other thing I would say that I really liked was that there were no decisions that were waiting for me to be made when I came back. I wouldn’t have liked that where other people like, well, let’s put this on hold till Jason’s back or what, I don’t, I don’t want that either. So any decision that needed to be made was made. Things were, things were tried. Normally I would weigh in on certain things, things were tried, I didn’t weigh in. 'em was great. That’s just how it should be. That’s exactly how it should be. If anything has to wait for you, I think it’s kind of a bit of a problem. Also, it’s another symptom of, uh, of you know, too much reliance on any one individual.

Kimberly (10:30): So was there prep work you had to do before taking off six weeks? I mean, I feel like any, I’ve taken a vacation. It’s like that scramble to get things done before you’re gone. Did you have that feeling leading up to it?

Jason (10:42): Yeah, a little bit. I caught up with David before I left. I caught up with Elaine before I left. I caught up with Brian, who’s our product strategy person here because he, he and I are most similar in terms of the work that we do on a day-to-day basis, which is planning for the next cycle’s worth of work, reviewing projects that are in flight. So we caught up a lot and, and sort of talked a little bit about, cause I was gonna be gone for the beginning of cycle two, which is in the next batch of work we were doing. So we talked a bunch about ideas that he might put on the plate for cycle two. So we worked some of that stuff out ahead of time. And then I caught up with, um, with Scott, who’s, um, one of our principal designers, um, and asked him to sort of take over my role a little bit while I was gone working with Brian on product development work.

(11:27): And then, um, talked about some other stuff we’re working on, but it was basically, uh, three or four people that I really caught up with prior, otherwise I just left. And um, you know, those are basically my, essentially my, not even direct reports, but peers and people I work with on a day-to-day basis on very similar work. And so just kind of wanted to line up a couple things so everyone was clear and uh, help where I could and then, and then step away. That was it. I also wrote, I wrote a message to the whole company prior, about a month prior or something, just saying I was gonna be taking off. I haven’t done it before. And it was kind of a, uh, an admission that this is a long time coming and just wanted to get everyone a, a headstart on that. So I didn’t just like drop off the map and be like, what happened? So I did that too, but that was, you know, that took 10 minutes to write.

Kimberly (12:13): And then David, question for you, did your role change with Jason being gone or was it just like, Nope, I kept doing everything that I was always doing before.

David (12:23): I don’t think it was that different. I think, um, Elaine and I would just meet on the weekly basis. Usually that’s the three of us, and then it would just be the two of us. And it was the same sort of order of business. Now, part of the reason why this kind of worked was to accept that even though Jason was stepping away for six uh, weeks here, there were certain things that were already in motion. Like, well, we, we weren’t going to start a new product, for example. That wasn’t gonna happen while Jason was away and it didn’t need to happen. First of all, we’d already laid some foundations and there was some people working on that new product we’re working on, so that could run in itself. And just realizing that there were certain kinds of projects that it didn’t make sense to take on, but there aren’t that many.

(13:07): And as we talked about, they’re quite infrequent. Just like probably if, if I was, when I was out for, for six weeks, I’d probably be a little surprised if I came back and like, hey, by the way, we’re off the cloud. Like we just, um, we set that up or, or, uh, Ruby, we’re not using that anymore. We changed to JavaScript. That’s what we programing now. Um, so there are some of those sort of big foundational tenants of how we build or how we work that you’re not gonna change when one of the principles is, is out for that amount of time. But those are also the kind of things where even if we wanted to change it, it wouldn’t matter if that had to wait two months or even if it had to wait six months. Some of those big Titanic switches are like ones every few years kind of stuff. So if they have to wait a little further, it’d be just fine.

Jason (14:00): The other thing I want to add is one of the, the one other change we made was to shift from exploration to production on some ideas we’ve been working on. So we’re working on a new product right now and uh, we’ve been working on it for just a few months and during that, those few months we’ve just been exploring ideas and then I thought when I was gone and I’ve been leading that charge, and so I thought when I was gone, it’d be a good idea to shift into like let’s build some of those ideas out so when I come back we have a basis of something that’s actually working. And so that was also a nice change and a good shift and a good timing for that. But we needed to do that anyway, so it was just a matter of sequencing it at the right time and I felt like that was a pretty good time to do that. So that was one other small change we made, but otherwise, um, everything was basically the same.

David (14:44): It’s funny because we had something similar here with our cloud exit. We had to build some technology to facilitate how we were gonna run our applications in the cloud. This, this thing called MRSK that I knew I had a two month slot to focus all in where I had no distractions and no travel lined up at all. And I knew there was a deadline coming up where I’d have about three weeks at least worth of traveling. Then I would have a bit of a punctured schedule after that. So sometimes it’s almost like you have the inverse, do you know what, I’m going to take the inverse of a sabbatical right now. I’m gonna ultra focus on this one thing for two months, such that, as Jason said, you can get the project to the point of where it can go downhill. And we have this feature in Basecamp called the Hill Chart, and I really love the metaphor of the hill chart.

(15:33): The hill has two sides, it has the uphill side. That’s when you’re still figuring things out. You’re not quite sure how the pieces are gonna work together. You’re not quite even sure how many pieces there are. You’re still uncovering things. Then once you reach the top of the hill, that means you figure things out. Now the downhill part is the production part as Jason says. It’s, we have a lay of the land. We may still discover a few things here and there, but generally speaking we know which way we’re gonna go so we can just roll down the hill. That’s where I wanted to get with this meers project. I wanted to get on the top of the hill such that once I then said like, you know what, for three weeks we still have to go just as fast for our own internal deadlines of when we wanna get out of this damn cloud situation. But now way more people can be involved and it can be way more independently driven. We’re not trying to figure out the whole vision or what have you of, uh, of how the thing is supposed to be.

Kimberly (16:24): Okay. Before we wrap up from both of you, any like big takeaways about sabbaticals? I know there’s a lot of people who are listening who are like, yeah, this sounds like a dream world. It is hard to even take a week off. What is your kind of advice for those folks?

Jason (16:38): Well, what’s funny is when I announced to some people I was taking six weeks off, a bunch of the Europeans just said, you mean vacation? You mean holiday? Right? Um, so most people, most people around the world actually get some more time off. I know most, I mean most is probably not accurate, but plenty of people around the world, uh, uh, take around six weeks off a year and things run okay. So I think that the big thing is, is don’t fear it. That’s gonna be fine. You’re not as important as you think you are. It’s just a good thing to get through your head anyway. And, uh, trust in the people you work with to do a great job while you’re gone. And also when you come back, come back with curiosity. Like, yeah, I didn’t check back and read everything that happened, but I’m curious about what did happen, what decisions were made that I wouldn’t have made or whatever.

(17:22): I just, that’s how you have to approach these things. Um, the organization ran differently when I was gone to some tiny little degree. What was that degree? What can I learn from that? Great, I’m not that important. That’s great too. You know, that, that kind of stuff. This is healthy. It’s a healthy time to get away and a healthy time to come back and realize a few things about yourself and what you do. I, I think that’s the most important thing as far as like what to do. I putted around the house, did a bunch of stuff, you know, whatever. It didn’t matter what I did, didn’t matter. What I didn’t do is what mattered most is, is I didn’t work, I didn’t think about work.

David (17:53): I think what’s really key too is first of all, enjoying the boredom. Like that was the big one for me. Like, I was not bored for the first three or four weeks. I just, there was enough stuff, enough interesting things catching up on the world. And then there was the boredom phase and I, I actually, that was the most important part for me. The two weeks where I was like solidly bored, um, was the almost the main recharging phase where like when I get back in, I am really fired up to do some cool stuff, dive into some real challenges, and then that pairs with this fact that when you come back in, it’s kind of like stepping out into the light after being in the cinema in the middle of the day. You’re like, this is really bright. Like your aperture almost needs to readjust or not kind of readjust.

(18:41): It has to readjust because the light comes in differently and you just see things very differently. When you’re in it every day, every week you fall into just a rhythm where it is difficult to question the underlying assumptions of why you do what you do. I mean, when Jason came back, we had some wonderful discussions about big picture things that we perhaps wouldn’t have discussed if it had just been like another Tuesday meeting after the one we had last week, that the separation itself gives space for the broader thoughts, the further distance and and so forth. I think actually by the way, Jason, the last time you took a longer vacation in '14 was when we became Basecamp. Yeah. So sometimes that dis distance to the business is really crucial for being able to give your mind enough space to work on the business in your head. Like, what do we really want? Why are we doing the things we do? You come back and you’ll find some of them, oh, wonderful, let’s keep doing everything we’re doing in that department. Then other things you come back and say like, do you know what now with the distance mm, something new here is needed.

Kimberly (19:47): Well, we are all glad that you’re back and glad that you were well rested and next week we’re gonna be answering some listener questions on the podcast. You guys know I’ve been saying that I wanna do this for a long time and it’s happening. Um, we’re, I’m hoping that we’re gonna do this a couple times a year. So if you have any questions for Jason or David about a better way to work and run your business, leave us a voicemail at 708-628-7850 and we just might answer your question on an upcoming show. You can also send us an email to rework@37signals.com. REWORK is a production of 37signals. You can find show notes and transcripts on our website at 37signals.com/podcast.