The Learning Leader Show With Ryan Hawk - 205: David Heinemeier Hansson - Falling In Love With Your Work & The Future Of Work: ReWork

Episode Date: May 21, 2017

Go To www.LearningLeader.com For more information on DHH and this episode Common themes of leaders who sustain excellence: "For me it's falling in love with the work itself..." Being excited to do the actual work everyday... The actual day to day work "I don't have a need to think "What's Next?" -- "I'm thrilled to do the thing I've fallen in love with." How did he become DHH? What percentage of your job do you love and what percent do you dislike? DHH works to minimize the parts he doesn't like Managing others is low on his list of what he loves. "The thought that you can't be innovative if you aren't in the same room is bullshit." -- You can do that remotely, in fact better in most cases. DHH shares why the open office concept is horrible for creative people who like to "get shit done." Remote work gives peace, tranquility, quality Commuting to work can be a wasteful, drain on your life The future of work -- More remote work, more contractors, less full time employees "The office is something you choose to have, you don't need to have it." "The Day I Became A Millionaire" What DHH learned that day... What changed? What didn't "The things that brought happiness were the things I was already doing. I love writing, programming, reading." Will a certain amount of money ever be enough? Ray Kroc said "No." "The human condition does not end because you get rich."  You'll still have problems. Best advice to give to people early in their careers? "Be careful what you wish for.  Managing other people is not in my top 5 things I like to do." "Prove you can execute.  That's the way to get to the executive level. Just simply make shit happen, you get shit done." You have to weigh shipping vs quality Take measured risks, and don't be afraid to make mistakes    David "DHH" Heinemeier Hansson is the creator of Ruby on Rails, founder & CTO at Basecamp(formerly 37signals), best-selling author, Le Mans class-winning racing driver, public speaker, hobbyist photographer, and family man. He is the best selling author of ReWork and Remote: Office Note Required.  You can also read his wildly popular writings on Medium.com/@dhh

that you can't be innovative or other bullshit terms unless you can get everyone together in a room. And I just went like, that is clearly just false on its face. We are just one out of, I don't know how many examples of companies that others certainly would qualify as innovative or whatever. And we're doing extremely well and we're doing remote. So this is clearly false on its face. It's false on its face that magic or innovation can only happen when people are saying, sitting around the same table at the same time.

Not that it can happen in that scenario, just that it can also happen in plenty of other scenarios. Proud to say that this episode of The Learning Leader Show was brought to by Roan, R-H-O-N-E, Rone.com, premium activeware, engineered with principle, performance, and progress for the modern man. They build clothing around three main tenants, cutting-edge performance, premium comfort

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And as you're checking out, type in the code Hawk. Simply Hawk, H-A-W-K to get 15% off. Now, Rohn does not typically do discount codes, so this is a special one. It will expire within a few months, but type in Hawk, H-A-W-K at Rone.com. Hey, and welcome to the Learning Leader Show. I am Ryan Hawk. Thank you so much for being here. I love doing this.

My featured leader tonight is David Hennemeyer Hansen, better known as D-H-H-on-Line. He's a creator of Ruby on Rails, founder and CTO at Basecamp and he's the best-selling author of a few books one titled rework as well as remote office not required he is thoughtful interesting and thought provoking love this talk with DHH a few of the topics we got into the future of work what will it look like will we all work remotely will we be contractors fascinating part of the talk and then how his life changed or didn't when he became a millionaire based on the investment personally from Jeff Bezos in their business.

And then his best piece of advice to those early in their career. Be mindful of this part of the conversation. It will be helpful. Ladies and gentlemen, without further ado, it's D.H.H. David, David,

thanks so much for being here on the Learning Leader show. Welcome. Thank you. To get us going, I've been looking forward to this one for quite some time. I've studied your work. I've read a lot of what you've published and seen the success you've had in your career over an extended period of time. I'm curious from your perspective,

what are some of the common themes of those who sustain excellence over an extended period of time? Sure. I think it's probably as diverse as the people who get to be at that level. We all have our own tactics and stories that I think we tell ourselves for why we are, where we are, and how we ended up here. but I can just answer for me. And for me, sort of getting and staying at this point has been a big part about falling in love with the work itself, not just the idea of the work, not just the idea of success, but the actual doing of it somewhat eight hours a day for 10, 15 years in a row. I find that the people I meet who fall in love more with sort of the concept of what they're doing

rather than the actuality of what they're doing or fall in love with the notion of success, they either get bored or just don't have the stamina to keep running in the same direction. So for me, as it comes to Basecamp, which I've been doing for, what, close to 14 years now, and Ruby on Rails close to 15 years, a lot of that has just been, I really just enjoy it.

I really just enjoy sitting down in front of the computer working on Basecamp, writing Ruby and Rails code and continuing to push that forward. So in that regard, I don't have this need to think what's next. What is the thing I'm going to do after this thing? I'm just thrilled to be able to do the thing that I've fallen in love with. And that just makes it easy. That makes it the default, actually, for me to just continue on the path that I'm on.

And of course, that's all the easier given that the fact that path, has turned out pretty all right so there's not a lot of pressure for that to to necessarily change given the fact that I just really enjoy the work itself and I really enjoy getting better at that work itself I really enjoy continuing to hone the craft of programming continuing to work on base camp the company as our best product continuing to work on base camp the product itself because I use the product myself all the time every day multiple hours a day So those are some of the factors that sustain me.

Wow, a really thoughtful answer. I appreciate that. For the people who don't know what Basecamp is, could you describe it for us? Sure. So at Basecamp, we help small and medium-sized companies deal with changes, with growth, with managing people, projects, and work. Basecamp started out solely as sort of a project management system. We created Basecamp for ourselves back in 2003 to manage. client projects. Basecamp before it was called. Basecamp was called 37 signals and it did

work for hire design work. And that kind of work involved clients and it involved trying to do project management over email. And as most people have tried to do that, that seems easy to get going and then it quickly turns into a mess. So we made a piece of software that brings together a bunch of different tools that most people need most of the time to get a handle on work and on projects, things like tracking assignments and responsibility of the work, having one place to put all your files as they relate to the project, having one place to announce things, having an ephemeral chat to check in on things, having these questions we have to follow up on the state of affairs and so forth. And we put all this together into one software package that people buy on a monthly service basis. We have one product, one price. It's $99 a month with a small discount if you pay for a year in advance.

But that's basically it. We just sell this one thing to help small and medium-sized businesses make sense of it all. Get on the system and perform better. It's amazing. I've studied a lot about Basecamp. I read Rework. And so there's a lot to dig into in regards to your work because this show is focused on, David. And by the way, I know online for those who are new to you, even though I'm also imagining you bring quite an audience in your wake as well.

But you go by DHHH on Twitter and just about everywhere I've seen. And I think it's interesting. I was talking to my wife about this earlier. I said that I love that David's almost brand himself D.H. Obviously, it's your initials, but not everyone goes by their initials. How did that become your brand, so to speak? I think it just started back in when I first got online and this notion of having a unique name just makes it easier to know exactly who you're referring to. I don't know how many David Hansons there are in the world, but quite a few.

It's an extremely common Swedish last name. So when you combined it to David Heinemar Hansen, to the best of my knowledge, at least, just one person with that full name. So that just seemed like having a unique identifier for something is helpful. And then shortening it up to at DHA just sort of came natural when I realized that nobody knew how to spell Heinemeyer norhansen. Just having that simple moniker and I can use that in all sorts of contexts where it's convenient to have a short handle. That was how it came to me. getting a little bit back to your first answer to my response and sustaining excellence, David, a question that I have been asking a lot of mentors and people that I meet with,

whether I'm the mentor or mentee and potentially a lunch, is what percentage of your job do you love and what percentage of your job do you strongly dislike slash hate? And I find it one, that's interesting that a lot of people haven't thought of that. And two, their answers are anywhere from, well, it's 50-50. or I don't know, 75, 25, 25 meaning love to hate. And for me, it feels like yours is either at or near 100%. Is that accurate? No, in one word.

I certainly have aspects of the work that I do that I don't do because I love it. I do it because it needs to be done. Okay. Or it enables other things that I do love and it facilitates those things. there's a lot of factors and aspects of running a company of 50 people that I think it'd be hard pressed for anyone to say that they loved every aspect of that. What I do try to do is to be conscious of that fact. The fact that I know I don't particularly enjoy this aspect of the work and then I seek to minimize or eliminate as best as I know possible. Sometimes that's simply a

matter of delegating, finding the people who do love this part of the work and getting them involved to work on it. Sometimes it's simply realizing, hey, we don't need to do this work at all. Let's just stop doing it. I find that to be uniquely gratifying. It's kind of one of my favorite aspects of working on code is the leading code, taking code out that's, you've come to a realization is no longer necessary. You can get there through another path. And there's just endless amounts of that stuff in the running of a business. And then focusing more and more on the things that that you do enjoy and finding those things and what they are and crystallizing those. And some of it, of course, is also just learning to love some aspects of the business.

I think perhaps I've always sort of liked writing, but I've grown to love it a whole lot more as I've done more of it. And I find that that's often true as well, that you sort of like, you don't like a particular activity, perhaps because you don't do it as much or because you're not as good at it, but if you change those two parameters, if you get better at it and if you do it more, there's a whole lot of things that turn out to be actually quite interesting. I find this is another example where this is true is in sort of the statistics of the business or the data of the business. We have someone dedicated to be a quote-unquote data scientist at base camp, but I've dug into that domain a lot over the years and I find it just fascinating.

interesting in ways that I didn't find putting the numbers together that interesting at the beginning of the business because I hadn't thought about it that much I hadn't gotten that good of it I hadn't developed an eye for it but now that I have I do enjoy it so another aspect of the uniqueness of your business is that your workers primarily or if not all of them I believe are remote correct meaning they're all they could be they could live anywhere and I'm curious from a management slash leadership perspective. What's the cadence? How does that work? There's a lot of questions there I have when it comes to remote work and the future of work. But I'm curious to learn about how it works at Basecamp for you, as well as I know you work with

Jason Freed in regards to Basecamp as far as how you guys lead. But curious to learn about the remoteness of it. Sure. So part of the remote story of Basecamp, camp is it's always been the story of base camp. Unlike perhaps most of the companies that have been around for a while, we didn't convert to remote. We were founded on remote. When I started working with Jason back in the early 2000s, I was working from Copenhagen, Denmark. We built a base camp with me in Copenhagen, Denmark, seven time zones away from Chicago, Illinois. And that sort of, that was just how things were founded. So we took that a little bit as just a founding concept, which meant that we didn't really in the early days, perhaps, give it that much thought that this was a different way of

working compared to how most people were doing it, that they were buying office space and forcing everyone to commute into the same central location. We just never did that. So over the years, this initial approach just grew more refined, I suppose, because we just kept on doing it. To the point where I fell into a little bit of the illusion that this was going to be. a completely well-understood domain for most people. And if they weren't doing remote, they at least examined the opportunity and carefully decided why they weren't doing it.

Well, that obviously, not obviously, clearly not obviously. The surprise for me was that that was not the case at all, that most business people I talked to had not considered remote very deeply at all and had sort of a reflexive, a position to it that was based on sort of handwavy shit like, oh, the magic needs to happen when we're all sitting together and talking.

That, like, you can't be innovative or other bullshit terms unless you can get everyone together in a room. And I just went like, that is clearly just false on its face. We are just one out of, I don't know how many examples of companies that others certainly would qualify as innovative or whatever, and we're doing extremely well, and we're doing remote. So this is clearly false on its face. It's false on its face that magic or innovation can only happen when people are sitting around the same table at the same time. Not that it can't happen in that scenario, just that it can also happen in plenty of other scenarios. So that led to actually

writing a whole book on the subject. We wrote a book called Remote Office Not Required a few years back where we collected all the main arguments for why going remote is a good idea and then enumerated all the tactics we use at base camp to make it work. And the sort of short recap of that is that things have changed. A lot of people have formed ideas and perceptions about what remote is or isn't based on, for example, what technology looked like 10 years ago, which just aren't true. Lots of things have moved forward at such a pace where, for example, video conferencing and talking face-to-face via that has gotten really, really good. If you were to buy a video conferencing system in, like, let's say, the late 90s or the 2000s,

weren't that great, right? Bandwidth wasn't good enough. You needed all sorts of dedicated hardware. These days it's really easy. And not only is it really easy, the quality of that interaction is damn near close to what it is to sit face to face. So if that's the main thing that you're sort of like, well, I need that detail of the facial expressions and the interaction that comes from sitting face to face, well, first of all, you can have a 95% as good of a version just doing it through any modern

tool or Skype or hangouts or whatever. The second part of that is realizing just how often that's not needed at all. And not only not needed, but directly harmful. I find that, the modern office, particularly the dreadful version that is the open plan office, it's just an assault on concentration and dedicated work. It chops up the work day into these work moments and it makes it really hard to get serious thinking done, which is the cornerstone of creativity and productivity and all these other aspects of work that we, that everyone keeps saying, oh, this is so important. We need more creativity. We need more innovative. We need all these things.

And then you're sticking people into a pen where they're all sort of sitting in the same room and constantly being distracted by each other. I don't think that that's a good way to go. Whereas remote, on the other hand, kind of gives you peace, quiet, and tranquility by default. That you're either in your own house or you're in some location where you control your environment to a degree that's just not possible in most offices. Because most offices these days don't have individual doors that lock in the same way that you're, bare bedroom can or whatever outfit else you're using to do remote work with. So I kind of find like there's a lot of the intrinsic attributes of working remotely are just uniquely well suited to doing creative, innovative work that requires long stretches of

uninterrupted time. So we were making that argument. And then there's all these auxiliary arguments such as what a drain it is to commute. Lots of people, especially in the US commute for surprisingly long distances, and it has all sorts of adverse impacts on their health. There are not a whole lot of things that are worse than the road rage that comes from sitting in congested traffic for an hour each way to and from the office. It's just a waste of life. And as we talked about when you look at the pie chart of how you're spending your time, as I was thinking, like, which are the parts of working that I love and which are the

parts working that I hate, most people would probably say that they hate wasting, let's say, an hour or two every single day to commute to and from an office. Not everyone will get these exceptions like, oh, yeah, my commute is my favorite part because I get to read a book or get to bike or whatever. But I think it's fair to say, and the research certainly supports, that most people don't love their commutes. So if you have this magic wand that is remote work, where you can just get away with this huge part of people's lives that they have. hate, you're going to need to pretty strong arguments for why you shouldn't do that. And when I found that under closer examination, most of the argument for not doing remote work,

they were not strong at all. They were flimsy. They were emotional in the bad sense of that word as in not based on careful consideration. And they were just plain false. So remote kind of was our attempt to influence that discussion and make it more informed and then of course also advocate for the fact that this is how we get stuff done. This is how it's worked at base camp for the last 14 years. We have 50 plus people who are spread out all over the world, most of them in the U.S., but people in Canada and the UK and Spain and Hong Kong and Australia all over the place. And it's working out as exceptionally well. It's not nearly as hard as you would think it is. I think there's a lot of fear of like, oh, well, I need to be the sort of specialist to be able to make this work.

I don't think that's true at all. There's certainly things that you need to be mindful of in different ways than you would in an office. But I tend to find that's just because it's the devil you know. There are lots of things you should be mindful about in an office that most people aren't. They're just comfortable with it. What do you think in regards to the future of work? So when talking about remote, and this is fascinating to me just because I think about it for myself, I'm still in my early, early mid-30s and my, my children even, is what will work look

like in 10 years. And like Matt Mullenwig, who has, who founded Automatic, which is the business behind WordPress.com powers about a quarter of the internet. In my personal website, I believe his entire business is all done remote. And he has, uh, many, many employees. But when in regards to full-time employees versus contractors versus being in big buildings, commuting, everything you just talked about in the future, do you, I have to believe more and more will be in the lines of the way you guys do it at base camp, the way automatic does it and many others to where work is done. Basically, you're held accountable to get your work done. And as long as you do, it doesn't really matter where you are, just the fact that you've got your work done. How do you say,

the future of work? I like to predict the future by looking at yesterday's weather. So what are the trends where we're going? And the trends of where we're going are clearly in the court of more remote work. If you look at all sort of statistics on the number of people work either partially or completely remotely, they're all up, up and away. So in that way, it's pretty easy to predict at least a near term future because you just continue the trend out and more people are going this direction.

And I think not only are they going to this direction just because that's the trend where they're going, but because that's a better way to live your life for a lot of people. Now, again, not everyone loves remote work, at least not at first and as many times not in concept if they do, even if they end up doing it in practicality. And perhaps not every bit of work is well suited for remote work either. But I think for most people, for most work, as it falls under these creative endeavors, whether you're writing or you're designing or you're writing code or you're writing emails or you're writing prose, these are all domains that benefit from the simple facts of long stretches of uninterrupted time to get work done. And they're all areas that benefit from wasting less time on needless aspects of life, such as commuting. So, in my opinion, the fundamentals are just strongly in favor of remote work for a lot of domains.

So it's easy to see that over time, these advantages are simply going to compound such an effect that this becomes the default. And in many ways, it has become the default in several regards. If you talk to new companies that are starting today, this whole idea that, oh, to start a company, the first thing you need to do is to get an office and a fax machine and a shredder and whatever else. or else sort of mechanics that people used to think like, oh, this is what's starting a business is like. That's totally off the table, right? Most people are not doing these things when they're first setting out.

They may end up in that situation eventually, but it's certainly no longer a requirement to get going. And when it's no longer a requirement to get going, you might well realize, too, that it's not a requirement to sustaining and it's not a requirement for success either. And just that optionality is huge. The fact that an office is something you can choose to have,

not something that you must have, and that plenty of companies are choosing not to have that or not using it as a major component of the work. We actually do have an office in Chicago, but we kind of bought it as a luxury, as a splurge 10 years since the existence of the company. And even to this day, out of the 50 people who work at Base Camp may be on any given day in Chicago, there's five people at the office. So it's clearly not a major factor of how we do work. I think the aspect of this is that our tools,

are just getting so much better. Obviously, we're kind of selling our own book here in the sense that Basecamp is the tool that we use to make remote work for us at Basecamp, right? That if you have a set of tools that allow you to collaborate, to slice up work, to delegate work, to inform workers of what's going on and to collaborate, well, then it's a whole lot easier, right?

You're not comparing doing remote work to how it would be like if you just had a phone line and a fax machine. Yeah, in those cases, they were pretty poor substitutes for getting into a room and, I don't know, drawing on a whiteboard or sitting in front of a computer together. Versus these days, the competition we have, the tools that enable remote are just so much better than what they used to be. And I think that that kind of improvement sometimes just sneaks up on people, that things have gotten so much better just over the last decade that sometimes you just, you don't. don't really realize that you're kind of like the frog getting boiled slowly that you know things that didn't really make sense 10 15 years ago because the fundamental infrastructure was not there all of a sudden it's there and you didn't realize it because it didn't happen in one snap it wasn't like we went from one day of phones and fax machines to next day of base camp and Skype and hangouts and high bandwidth and so forth it happened gradually and those gradual changes are sometimes hard to detect and hard to make the fundamental leaps from, even though the effect in the end is the same, that we have made an absolutely fundamental leap in how we enable remote work these days from where it used to be. What to shift gears a little bit.

You talked about the fact that you have a bigger interest in writing. You've written a best-selling book. You write regularly. I think you're, you can be quite outspoken. You're not afraid to share your opinion, whether it's on social media, Twitter, or, your post that I've read just about all of them on medium or use that as a platform. And one one in particular that I pulled out that I thought was interesting because I think a lot of people listening, maybe they have these types of thoughts.

And that is the day I became a millionaire. And you write about the fact that one day, and I believe it was 2006, Jeff Bezos had taken an interest in base camp and you and Jason sold him a minority no control stake of the company for a few million dollars each and you became a millionaire. And so I'd love to hear from you, you know, a lot of people, I think, whether they verbalize it or write it down and some do, they're on that path where maybe they have a certain dollar amount they want to earn per year or their net worth. and I thought you wrote a really thoughtful post about this and about your upbringing and potentially

what changed or didn't change from the fact that you now are and became a millionaire over 10 years ago. Can you share more about your thoughts on that specific moment in your life? Sure. I think as with lots of people, you have this notion of what's going to happen. You have this expectation of how your life would be radically different if all your worries or most of your worries about money kind of go away. And to some extent, that's true. Like, things do happen when you don't have to worry about rent or buying groceries or whatever.

But there's a baseline where once you crush that threshold, there's some real improvement to we have. I think people underestimate perhaps that threshold. and then they overestimate how wonderful it is to get far, far, far, far beyond that, that their life will be also magical if they can just buy the biggest house they ever dreamt up or all the cars they want or take endless luxury vacations or any of these other trinkets of rich life. And what I found, both from my personal experience and from talking to lots of other friends and fellow entrepreneurs who landed in the same boat was that,

not so much, or at least that these expectations were wildly inflated, that the things that bring us happiness, the things that brought me happiness, were doing the things I was already doing. Like the fact that I went from one day of having X in my bank account and the next day to have X plus a couple of zeros behind it, didn't really change those fundamentals. As we were talking about in the beginning, when I sort of slice up what I like to do and where I like to spend my time,

time, most of these things are actually not things that involve spending lots of money. There are things like writing. There are things like programming. There are things like reading. There are things like creating products. There are things like working with great people. There are things like engaging in fulfilling relationships within communities that I work with. Most of these core elements of where I want to spend my time and what brings me joy

and the flow experiences that come from that, they were the same. I mean, my daily life looks extremely similar to what it did before I became a millionaire. And the things that I derive great joy from are very similar. Now, that doesn't mean that it doesn't open new doors and you can't try some new experiences, and that's not cool. Like, for example, I've gotten the privilege to drive race cars, something that wouldn't have been possible if I haven't reached this notion of wealth. But even that aspect of it, before I started driving real race cars, I drove lots of race cars

on PlayStation, on Xbox, and so on. And they jump from that to there, it's not nearly as large as most people would like to believe. And I think that's really the key point here, is would like to believe that there's a lot of hopes and dreams pinned on this notion, oh, if only I could get X, then I'd be happy. And I'm sorry to say that I think for lots of people, that illusion is going to be, or is shattered pretty hard when you do arrive to that point. That this magical inflection point that was supposed to just bring you endless bliss doesn't really pan out like that. You still have all sorts of mundane human problems, all sorts of mundane human pains and bad experiences and bad days. and life isn't really that different in that regard.

Again, I'm talking about going from the plateau of sort of already doing well. Basically, anyone who works in technology with a steady job and the paycheck that comes with working in technology to jump from where they are to this place where I'm sitting right now, I think it's depressingly less than most people would be left to believe. completely different if you're going from like working minimum wage and just trying to keep your shoots on and getting your kids fed and worrying about insurance and so on and so forth. Right. There are these different thresholds where things do break.

But I find at least most of the people I engage with and when I talk about these experiences, which is generally not a popular thing to do. Just about the last thing that most people are interested in hearing is the trials and tribulations of millionaires. It's just not an interesting topic, right? And in some ways, it's kind of off the proper decorum to even talk about it because you're supposed to just shut up and be grateful for your life being perfect. And it just isn't. And to some extent, that makes it more, I don't know, isolating or whatever, that you can't even sort of begin to elaborate on all the ways that things aren't magically perfect just because you have X amount of dollars in your in your bank account

because people are not interested in hearing it and fair enough I'd say as I go over in that post if someone would have told me up front before I got to this point hey by the way by the time you get there like it's not all going to be fucking sunshine and um and rollercoasters I'd be like yeah that's easy for you to say like you made it there and then I got there and I went like oh maybe there was something to that point and is there a point where it's never enough or I don't know it's you get to you it sounds like you do what you love every day for the most part right and we talked about outsourcing or leveraging others for for parts maybe that you don't like as much but is there is there part too when it comes to

certain amounts of money it doesn't really matter because this there's people who just they get a million and they're like oh yeah but it's I want two million I want 10 million I want a hundred million at some point where just it will never be enough for some people. I think that's the natural trajectory. Because I think the natural trajectory is if once you tie your idea to like, oh, things are going to be wonderful once I reach this point, then you reach that point and you realize, well, maybe things are a little more wonderful, but they're not nearly as more wonderful as you thought they were going to be.

The natural protective stance against that is simply just to think like, oh, it's because it wasn't big enough. If I could just make this other leap where, like, not only do I not have to worry about what a dinner cost, if I could just fly private or whatever extravagant things that people think will make their lives bliss, you can keep going on this motion. And in some ways, you can keep striving and you can keep pushing something ahead of you. And you can keep thinking, like, if I just reach this one thing, then I'll be happy. Instead of actually getting down to the hard laborers endeavor, figure out what truly does make you happy. And the fact that in most cases, it's not adding additional cereals to something that already has digits and zeros on it, right? That you have to find your purpose and meaning in other things than just chasing that.

And I think that's scary for a lot of people. I've certainly had all sorts of struggles with that over the years in different ways, but in some ways it's worse. Some ways it's obviously and clearly and on its face better. And in other ways it's worse because there's kind of like a tyranny of choice that comes with the fact of like I don't have to work anymore, right? Like I could quit base camp tomorrow and I could still live a very comfortable life for the rest of my days just often this that I've built up. So that's an option.

Like that's a real option. I could choose to go through that door and I could choose to dedicate myself to all sorts of other different endeavors, right? And now I'm responsible for all those choices. either making those choices or not making those choices, or worrying about those choices, or ignoring those choices. And that's not a, I think, in many cases, a blissful place to be until you find peace with where you're driving your satisfaction

and your happiness and your tranquility and say, like, okay, well, this is me, this is what I do. And to some extent, I mean, as I said in the beginning, I've chosen to do that. I've chosen to come through realization. And I seem to just like the thing that I do every day that I've been doing for the last 20 years, which is a lot of sort of keeping up with the state of the world of technology and programming, doing my bit to try to push that forward in the domains that I have an impact on,

creating an interesting product that people want to pay a fair price for and work with good coworkers. These are all goals and achievements that were true, as I said before. I got to this magic point of being a millionaire, and it's also true for lots of other people. This is a very accessible dream, I would say. But again, lots of people not interested in having that conversation, very interested in clinging to the belief that, yeah, that's easy for you to say. If I just get to this point, then I'm going to, I don't know, what fantasies they have. Like, oh, I'm just going to travel the world. Like, that's one of the things I hear all the time.

You know what, over the past maybe five years, I've been on, what, 150, 200 flights? I've traveled the world. It's not always what it's cracked up to be. lots of times I look at my calendar and I go like I fucking just wish that there was six months of nothing like I have six weeks coming up where I don't have to go anywhere and not engaged in any of these other things and I just go like oh man this is bliss this is so great like six weeks where I just can focus on on these few things that I really like writing or programming or whatever wonderful I can't wait to embrace that so part of that is of course it's always greener on the other side right

but it's easier to see or delude yourself just to how green it would be on the other side when it's in an upward motion again no one's interested in hearing like oh i wish my life was more boring and i mean that's even a misnomer in itself that's a mischaracterization it's not that my life would be more boring if i didn't travel a bunch i think in in many regards it would just be plain better spending these long stretches of uninterrupted times making progress on technology and product or some of the things that I like the most in this world of everything that I could do, right? I go over this in the post too, this notion of you. You never seen a unhappy person in a Lamborghini or writing first class or whatever. You know what? You've just not talked to

enough people who've been in that situation. There's plenty of unhappiness to go around. It's just maybe expressed in a different way and maybe it's more optional, blah, blah, blah, I don't know. but the human condition does not end just because you get rich and the human condition is simply full of sorrow and regret and missed opportunities and anxiety and all these aspects of living life and they're there all the way around. They're not physical in the same sense and I mean, again, as I say,

it's a tough conversation to have because it's such an easy position to attack from like, oh yeah, again, easy for you to say, well, what about the people who are striving just, to make ends meet. And I have endless respect from that because as I also elaborate, like I did not come from a place of wealth at all. Like I think from sort of just the lowest rungs of middle class,

if you could even call it that growing up in Denmark. So I certainly have a quite intimate experience about what it is of being, like there's a week left of the month and like there's no money. There'll be money at the beginning of the month because that's when my Parents got paid, whatever they got paid. But right now there's just no money. And that's just the situation that we're in. And I sympathize with that deeply.

I'm just trying to caution people from thinking like, oh, well, all this bliss and happiness awaits at the end of a large check. Yeah, there's a movie I recently just came out called The Founder. It talks about Ray Kroc, a guy who was a successful businessman who took over McDonald's. I urge people to watch it. It's interesting, especially if you like true stories. of nonfiction events. And his wife, there's one moment in the movie, his wife pulls him aside. And this is after Ray's had immense success, a lot of financial, a lot of wealth.

And she pulls him aside and she said, well, Ray, will it ever be enough? And he kind of paused and he thought and he said, no. And he was just being honest. And that's the way he lived his life. And he did have immense success. But he had a lot of, there's a lot of bumps in the road along the way. And I think it's probably some highs and lows without knowing the guy. And I think that's illustrative of what you're,

disgusting. Another aspect, David, of your life, I would imagine. And I briefly described you the type of people who are listening to the show. These are people who are professionals who are looking, who are striving to either are already or looking to move into leadership roles, whether it's in a big company or the company of their own. And I would imagine you get asked for advice quite often, a number of different questions. And so when somebody who is who has that, thought and they say, David, what would be a great piece of advice you could share with me, a professional person looking to lead, potentially manage people, whether it's in a big or small company, it doesn't matter. But what's the best piece of advice you would deliver or maybe that you do deliver to those types of questions? Well, the first thing I'd say is it's kind of similar to the discussion we just had about wealth.

Be careful what you wish for. If I think of all the aspects of the work that I do at Basecamp or even Rails or anything else, managing other people is not on my top three, not on my top five. There's certainly rewarding aspects of that, but I think there's just an implicit notion that, oh, if you can climb the ladder and if you can sort of get into a leadership role, like, that's great. That's just by default, that's a level of success. What I've found is that that's very often not true, that there are lots of people who are far better off being what the sort of management lingo called individual contributors, people who are just really good and get better at what it is that they do, that you can climb a ladder of expertise and competence that's not about a ladder of managing more people. And that alternate ladder in many ways is far more rewarding and has far less stress in it. Again, some people are just obviously very interested in just getting leadership roles and management is what they do. But if you take the caricature of someone who's a manager and you contrast that caricature with just someone who's really good at what they do,

I think actually the caricature of both those roles would inform a lot of people to believe that the person, who's just really good at what they do, that's the more attractive role to be in. So this notion of just climbing the ladder for the sake of climbing the ladder and that that's going to be great, I put huge question marks next to that. I get that most people see that, oh, this is how I can make progress in my career, whatever. And then we're back to the discussion again we had before. So what does that progress mean? Is that because like you want a bigger paycheck or what are these aspects of it? What is it that actually makes you happy on a daily basis. How is it you want to spend the eight hours out of the day did you get five times a week

to work on? Is it trying to chase down other people and follow up with them and whether they did the work or assign them work or mitigate sort of interpersonal conflicts or any of these other things that is the work of management? I think if you looked at the actual list of responsibilities that most managers have and the work that they do every day, I'm not sure that there's that many people would go, oh yeah, I'd love to do that for eight hours a day. That sounds glamorous. No, they like the idea of it. In many ways, they like the idea of like, oh, it'd be great if I was higher up in the hierarchy and there's some prestige to that and there's all these other trinkets and goodies from that. The actual work of doing it every day, I think far fewer people than

desire to become managers are good at doing that work or interested in doing that work. So first question dearly whether that's what you want to do. Second part of that is, okay, say you've decided that is what you want to do. I find that, at least that our organization, maybe this is not true everywhere, the way to get to that point is to prove that you can execute. That's basically sort of a truism of being an executive, right? That you can take a problem and you can arrive at a solution

through whatever means that it sort of requires to get to that. So you can demonstrate that ability at the, level of individual contributor. You get a vague, fuzzy problem, which is usually the shape that most problems take into creative domain. And then you can simply just make shit happen on your own,

by yourself, or, I mean, in collaboration with others, but showing that you execute, you get shit done. That is the fastest way up that ladder. Because that's the thing that's in very short supply. Very few people are able to take fuzzy, vague problems

and then pull together all the either individual resources and capabilities that they have to complete that task or coordinate with others as they need to, to get that all the way to conclusion and get it shipped. Why aren't people good at that? You said very few people. Why is that the case? I think it's because it's, as I said, it's vague. It's fuzzy. It's not concrete. You have to make all sorts of tradeoffs that feel uncomfortable in the moment. You have to weigh shipping versus overall quality, you have to strike the right balance between these things, which means that you have to go out on the limb and you have to make judgment calls, and those judgment calls

may well turn out wrong. Lots of people don't like to be wrong in these ways, so they set themselves up in all sorts of defensive positions to guard against being wrong, and these defensive positions take on a life of their own, and then before you know it, weeks or months have just gone by when you haven't made material progress on the things you were trying to do because you were kind of to afraid in a very wide definition of the word afraid to do so. It feels like you got to, it's a lot of people, especially if you're working at big corporations,

do things to, I'm generalizing, but I think you can read about this anywhere. You do things to not get fired. And so you just take the safe route and you and don't really innovate, as you'd say. And so that's why the smaller, faster moving agile companies that give some impact.

people, give them freedom to potentially make a mistake, can accomplish big things much quicker and get everything done more so than a lot of people who don't want to get fired. Absolutely. And nothing but respect for people who don't want to get fired. Usually they don't want to get fired for all sorts of really good reasons. They need the money. So that just means that for lots of people, this goal of management is not that rewarding. You can wish for it and then you can end up being in this place where you have to do eight hours a day is manage, and then you can quickly realize, like, shit, this is actually not what I was interested in doing. The only interest I have in being largely, in being a manager, is as a leverage for getting

shit done. More of my ideas into the world, more impact imparted onto that world. And being a manager and leader, whatever you will, it's just one of the necessary evils of doing that. I mean, seriously, if I could get all the ideas that I had into fruition and into this world, just through my own two hands, I'd much rather just do that. That's an interesting perspective. And I appreciate, again, how outspoken and honest you are. And David, I really appreciate the fact that you've invested your time with me and my audience. And so I want to thank you and acknowledge the great work you've done.

It's impacted me in a big way. When I first read rework, I thought, I want to talk to these guys. I mean, I immediately reached out to both you and Jason. And so thank you for being here. Where would you send my listeners to learn more about you online? Thank you, first of all. Yeah. It's very kind of you to say.

Second, I'm on Twitter at DHH. It's a fairly high volume feed of all sorts of opinions. and politics and whatever. So even if you do like what I had to say here, you may very well not like that Twitter feed. Secondarily, I've written a number of books. Rework is sort of our biggest success, more than half a million copies sold worldwide

on how to run a better company, how to get more done in all the principles and tactics that I kind of alluded to here and that have guided us over the past 15 years of running base camp and then the book remote as we talked about principles and and ideas and how to run a remote company. And then I'm on Medium, also at DHHH where I write a whole lot about technology and venture capital and all sorts of other ideas.

So there's the three good places to start. Perfect. Well, thanks again. David, I appreciate it. And I absolutely want to continue this dialogue as we both progress, man. All right. Thank you. Thanks for having.

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