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A
I recently figured out how to articulate why I travel. It's because I want to inhabit philosophies viscerally instead of theoretically. To go to Brazil and be tossed around on the presentism of the Brazilian way of life is a visceral experience. Being in Japan and experiencing that way of life just in one small town in Akron, you can have people with vastly different value systems that say, if you value my place here at work, you'll run everything by me. And somebody else would say, if you value my place here at work, you won't bother me with these details. People have these clashing value systems even just in one location. I think it does help us to realize that we are not right and they are not wrong.
B
Welcome to the Work for Humans podcast. This is Dart Lindsley. I often refer back to this episode with Derek Sivers because here on Work for Humans, we've heard dozens of perspectives on what people want from work, and so many of them are different. What makes work great for one person is often pure suffering for another.
A
Why?
B
At least some of that difference lies in what each of us thinks defines a good life. In this episode, Derek and I talk about what he discovered writing his book how to live, which describes 27 often mutually exclusive perspectives on the right way to live a life. If you listen closely to how people talk about their work, you'll hear many of these beliefs running beneath the surface. Derek is an author, entrepreneur, and TED speaker known for founding CD Baby, once the largest seller of independent music in the world. He's also a former musician himself and circus performer with over a thousand completed shows. When Derek sold CD Baby for $22 million in 2008, he donated all of the money to a charitable trust and turned to writing on business, creativity, philosophy, and personal development. In this episode, Derek and I talk about how beliefs direct actions, some of the 27 Ways to Live found in his book, and the importance of crafting a company's personality. We also discuss using beliefs in the good life as a listening tool at work, nature versus Nurture when it comes to what we want from our jobs, data models as philosophical experiences and other topics. All right, if you enjoyed today's episode, hit that subscribe button so you never miss out on future episodes. And without further ado, I'm very pleased to bring you my conversation with Derek Sivers. Derek Sivers, welcome to Work for Humans.
A
Thanks Dart.
B
I spent a lot of the last week reading your book how to Live, and it's the weirdest experience. It is. I've got to tell you it's like 27 cult leaders talking in my ears.
A
Yes. Yes. Great comparison. You're the first person that's ever said that. I love that. Thank you.
B
So it's 27 descriptions of how to live in the voice of the people who might be telling you to live that way. It's a bewildering and almost disorienting thing because many of these beliefs about how to live are so ambient that you don't notice them when they're blowing by you and making you feel bad or good or like you should be something that you're not. So we're going to get into them a little later in the show, but I want to start with what you're doing right, like now. I don't want to know where you're going. I don't want to do what you're doing next, but I want to know the way you do business. The way you exist in the world is very different from anybody I've spoken to. It feels like you're creating yourself in public, and I can feel you gardening your digital presence to match and in particular to match your philosophy and your belief system. Is that perception accurate?
A
Yeah. That's amazing. Yeah, that's very, very accurate.
B
You said something that I thought was really powerful. I'm going to talk for the whole show. Let me just say this is going to be a very easy podcast for you because I'm talking about me.
A
I'm enjoying this. Thank you.
B
I'm just going to tell you about you. But you said business is creative. You can do things any way you want. There's no need to adhere to norms. Norms are for businesses without personality. So pour your personality and philosophy into the way you do business. People actually appreciate it when you do things in a surprising way. So what is your personality and your philosophy that you're pouring into your work right now? Oh, or how does it manifest in your work, I guess is the better way to ask it.
A
I'm going to answer that in a second, but you just reminded me about the personality of a company. If I go to the origin of why I started thinking that way, I think it was as a consumer first I noticed that I really felt more loyalty for companies that exuded personality. So bicycles. There is a company in Minnesota called Surly Bikes. S U R L Y Surly Bikes. And their website just exudes personality. They like to do things kind of like muddy and dirty and just the way they talk about their bikes. Yeah. Well, Jim said that our previous Ogre model Wasn't tough enough for him. So we just made the new, you know, whatever snot ogre bike. And you know, if this isn't tough enough for Jim, I don't know what is. And I just love these guys and I feel this incredible brand loyalty for surly bikes. I won't consider buying any other bike even if rationally maybe I should. But I just feel loyalty to them because they exude personality. So even something as wonky as DNS, I was using Cloudflare for my DNS because they had the fastest ping times in the most locations around the world and I used them. But like eh, I never felt great about that. It was just Cloudflare, whatever. And then I saw bunny bunny.net from Slovenia and they exude personality. So as soon I just poked around for maybe like 20 minutes on their site and I saw they could do everything that Cloudflare does. Maybe not quite as well, but probably just as well, but I felt better about it. So it's like you know what, I did it. So it's like I took the 90 minutes of work and I moved all of my domains off of Cloudflare over to Bunny DNS. And I'm really happy about that because it feels better. So those are just two silly examples. But then when I accidentally started my own company, the accident is just circumstance. I didn't mean to start a company. I was selling my own CD and then it grew. But when I realized, oh shit, I've just started a company, I thought, well, I could just do it the normal way. But then why bother? I want this thing to exude personality the way that businesses I love exude personality. So that's where it all began. That's maybe why I started thinking this way. I thought we should mention that first before we get into what I'm doing. Now on that note, for example, formalities. We've all probably been to a very casual business at some point. Like if you go to a beach somewhere in the Caribbean and you want to get a snorkel and fins, there's just a guy in a grass shack that you just give $5 to and he'll give you a snorkel and fins. And business can be that simple. So when people try to do things in an extremely complex and formal way in order to impress investors, everybody and you know, they have these dreams of becoming the next Google. I think it doesn't have to be that complicated because I've rented a snorkel and fins on the beach before. I know how simple it can be. And so at every stage of my business, even inside the workplace, I just chose the simple, casual way. So I remember after years of having employees, I think after I got to 40 or 50 employees, somebody came by in Oregon and said that we needed to have some kind of notice posted up in the workplace by Oregon law. And that was always my question, by the way, if somebody said you have to do this for your business, I said, will I be arrested if I don't? This isn't just a should or best practice, right? If it's best practices, I'm not going to do it. Only if you're telling me it's absolutely the law, like I will be fined and may be arrested if I don't, then I'll consider it. And there is one thing, I forget what it was. Some kind of notice that, yes, by law in the state of Oregon, any business with some number of employees needs to have this posted somewhere in the office. I said, can it be anywhere in the office? They said, yes. So I put it on the ceiling of the bathroom, I got a ladder and I went up to the ceiling of the bathroom and I tacked it up. I said, there. We have now officially posted our notice. Stupid rule. So then you mentioned my website. I do these same things with the website. I learned HTML and what, long ago. I mean, that takes two hours to learn. I learned some basic programming in my spare time. And I make a website that's really just about getting my ideas from my brain into yours. And of course, you see, some people use these web frameworks that just have hundreds of thousands of lines of code just to get a paragraph from their brain into yours. And I look at that and I think, God, that's a lot of bloat. That's really not necessary. So I try to just strip everything down for the same reason. Like I said, like buying a surly bike. It just makes me happier when I see a really lean, handmade site that doesn't have the bloat. It feels like the product of somebody living a thoughtful life. The cliche that we've all heard, right, of just, well, you know, you just live a normal Life. You have 1.5 kids and a dog and a white picket fence in a house, right? We've all heard that line. It's a cliche, but some people do that with their website. They're like, well, you just fire up WordPress and you do da da da da da. And it loads in a hundred thousand lines of PHP and 12 includes of JavaScript files and 6 CSS files and blah blah, blah, and you get your thing, but then you get your paragraph of text from your brain to theirs, but all you really wanted to do is get that paragraph of text. And it feels like you're just going through the defaults without questioning them, just living the default life. Yeah, maybe I care too much about websites or something. That's why I do things in a non standard way.
B
It's all through your aesthetic, I think. I think your writing, if I was going to say, is without bloat. And so one of the things that your writing does is it's the exact kernel of information that you want to get across without any extra. And that information that you want to get across happens to be something from down close to the operating system of the world. It so happens that kernel of truth that you're after is usually like, no, this is fundamental. So it's fun and it's fast to read.
A
I wish more books were like that. Again, that came from a pain point of reading other people's books going, ugh, get to the point, or enough with the examples. I got it, I got it. Okay, Shut up. Come on. 300 pages to say what you could have said in 20. I wish I could buy a book that would just say it in 20. I tangented first because I wanted to set the scene. You asked, what am I doing now? Well, right now I. For the last two years, I've been completely focused on one idea which is useful, not true, which is my book. And I'm not saying this to promote it, but I noticed that this was my unspoken assumption behind my beliefs and the way I think. So you said when you're looking at workplaces, people have this unspoken assumption that, well, yeah, this is how to live. This is what a workplace should be. And somebody else thinks, well, yeah, well, this is what a workplace should be. But it's very different from what this person thinks. And hence the clash. So we all have these things that seem so obvious that we don't even say them. And so to me, something that was so obvious that I wasn't even saying it was that I choose my beliefs because they're useful, not because they're true, but because believing this creates an emotion which creates an action that is the action I want. So I choose the belief that generates the emotion that generates the action that I want. And that's why to believe something. And every now and then somebody in my comments would say, but that's not true. I'd say, I don't care if it's true. What do you mean, true? Who's going to say what's true or not based on what measure? I mean, yes, there are some factual things like there I'm clapping my hands, that's true. But, God, all things that are in the mind are debatable whether it's true or not, by what measures? So why would you use true as a measure? No, no, no. I choose my beliefs because they're useful, not because they're true. And I'd been saying this for a couple years without diving deeper into it. So then two years ago, I thought, you know, this is an interesting subject. So I spent the last two years learning more about it and now writing
B
about it it is. And I haven't read or thought about it much either, except for occasionally writing paragraphs where I say, I'm not saying this because I think it's fact. I'm saying it because it opens the next can on the shelf like it's a can opener or something.
A
On that point, Brian Eno, the record producer, he said, wants that his job as a record producer is mainly just to have strong opinions so that if the band is sitting there in the studio and they're not sure whether this or that A or B, he'll say, what about Zed? And they'll go, what? That's crazy. No way. No, that's an awful idea, Brian. And he'll go, okay, great, it looks like I've just helped you decide. So he wasn't proposing that idea because it was the right answer. He was proposing it because of the effect it had on their decision making. And that's his job as a producer, is to just have the strong opinions that help the artist better realize what they actually want.
B
Yeah, and sometimes you can do that to yourself.
A
Exactly. Like you just said with the can opener. I really like that. I'd never heard that metaphor.
B
Well, one of mine is that in terms of experience design, when you're thinking about experience, you should ask, what's experience? And I've come up with a set of rules for what experience is. One is all experience is in the present. If you're remembering something from the past, you're remembering it in the present. And if you're thinking about it in the future, you're remembering it in the present. And by the way, I heard this in one of your how to lives. I did hear this. I heard you say that. And all experience is internal, which is that by the time you actually experience it, it's gone through all the filters and it's gone through all of the processing, immense processing that happens before something from the outside world makes it to your internal world. And it's mediated during that passage. And so it's important as a designer to know these things because then you know what you're acting upon. All you're acting upon is that person's. Now, that's a very useful framing for me. And I don't know if it's true. It's a conceit.
A
Conceit. I like that. I agree with you. And it's a very useful way to look at it because it keeps you focused on the now instead of ruminating about the past or trying to predict the future, to just. Let's just keep this to the here now.
B
It's a very good example, I think, of the kind of kernel of truth that you pursue, which is that you are pursuing these essential, again, I want to say, operating system kind of questions, which I found really compelling. And so how did you in particular come to write how to Live? And I should read the whole title. It's how to live 27 conflicting answers and one weird conclusion.
A
It's an homage to. To a book called Sum S U M by David Eagleman. So I read Sum by David Eagleman. Loved it, read it again a year or two later, felt, wow, I think this might be one of my favorite books of all time. Some. Its subtitle is 40 Tales from the Afterlives. And it's fiction ish, where it's 40 little short stories, fables about what happens when you die. But each chapter disagrees with rest. So it's basically 40 different answers to the question, what happens when you die? And each one takes a radically different take on it. So one will say, when you die, you're alone in this giant mansion and you wander around for days. There's nobody else there. And finally you see another person who tells you, this is God's house. But God is a creator. He's not a manager. So he created life billions of years ago. You know the first time that an amoeba split into two and then four and then eight cells? He was done and he's off doing other things now. He forgot we exist. He doesn't know about human life. He created life, not humans. So then another chapter will say, when you die, you sit in a waiting room and you have to wait there until the last person on earth that knows who you are dies. And only then are you allowed to go on to heaven. And then another one's like, when you die, you find out that in your last life you chose to be a man. But in your next life you can choose to be any animal you want. So you decide to be a horse. And that one has a beautiful ending. But these are all just these little two to three page long short stories. But I love the format. I love that every chapter disagrees with every other chapter. But each one is so confident to say, here's what happens when you die, this is what happens. And then just three pages later it says, here's what happens when you die, that happens. And it's completely disagrees with every other chapter. So I love the format so much that one day I was driving down the road and I just went, I want to write a book called how to Live in that exact format where it's going to have these opinionated answers. Or like you said, would you say cult leaders? Yeah, as if written by like originally I was going to aim for 40 because it was an homage to the book Sama. It's 40 tales from the Astrolabes. I was going to try to have 4040 ways to live where each chapter makes its best argument. Why this is the way. This is how you should live. Live for the future. You know, everything must be done for the future. Everything you're doing in the present is serving your future self. And this is why this is the best way to live. And everybody should be living this way. And the next chapter will say, live for the present. The future doesn't exist. All that really is is the present moment. And the next chapter will say, follow pain. Pain is the compass that leads you to the right thing to do. The right thing to do is always the difficult thing to do. And I thought, God, that would be wonderful. Oh my God, I want to write this book. So yeah, with that flash of inspiration, it took four years to make it happen. It was also shortly after my son was born. And I had that thing that a lot of parents have, which is I want to teach him everything I've ever learned in life. And what if I die before I get the chance to do that? I want to write it all down. I've heard a lot of other parents have the same idea. So I combined these where it's like I wanted to put everything I'd ever learned in life into this book. But I'm never going to tell people to read a thousand page book. So my rough draft was 1300 pages, but there was no way I was going to publish 1300 pages. That's inconsiderate. So then I spent two years, whittling it down to these short, little poetic sentences that communicated all of the ideas I wanted to communicate, but as succinctly as possible. And the final book is 112 pages.
B
It's incredibly condensed considering that it started off at 1300. And just as an example of the internal conflict, the first one is, here's how to live, be independent, depend on nobody. It's about cutting time. The second one is here's how to live, commitment, and it's all about connection. And a lot of them are paired that way. It's like, do this, do the opposite of this. Many of them are equally compelling, but a lot of them are repulsive to me. But the reason that I wanted to have you on the show is that I've been doing research for a long time about what people want from work, and I hear strains of these beliefs about how to live flowing through how people feel they should work because it's so closely related. So it struck me that this might be a very powerful listening tool. And also the people that I have on the show. So one of them is think super long term. I had Ari Wallach on the show a little while ago. He's a futurist. He wrote the book Long Path, and he has the company called Long Path Labs, and it's all about how to live that way. And so it's a perfect example of that. So people come on the show, people I talk to. So as you developed this book, what surprised you?
A
Ooh. Every chapter completely convinced me that it was, in fact, the right answer. Even though I knew what book I was writing, and even though I had just been working on the other chapter yesterday and the next chapter tomorrow, every day I worked on that book, I felt, yeah, you know what? This really is the answer. I know the format. I know there are 26 other chapters, but come on, this one really is it. Let's just say, follow the pain. This really is the best way to live. That would be the most amazing life. If at every life's choice, you went towards the more painful option, you would constantly grow like nothing else. I know I need to finish this book and write the other 26 chapters, but this one really is it. And then the next day, I'd be writing the chapter that's just like, fill your senses, taste it all, do it all, hear it all, go everywhere. And I'd say, you know what? This really is the answer. This really is it. Never mind those other chapters. This truly is how to live. And it surprised me that every chapter had Me convinced while writing it that this was truly right answer. But then the next day I'd be on the next chapter and feel the same.
B
How did you research it?
A
It's the culmination of everything I'd ever learned in my life up to this point. It's hundreds and hundreds and hundreds of books. I mean, hell, I've taken notes on over 450 books I've read since 2007. That's when I started taking notes. But I probably read a few hundred books before that. Conversations with friends, diaries, insights. I went through them all. I reread all of my notes from every book I'd ever read. I reread all of my diaries since I started keeping a diary. I revisited every interesting insight ever had about life. And I squeezed them all into that little book, but then had to of course categorize them. Pick any random thought, whatever scares you, go do it. One of my life mottos and I have to think, well, which one of the 27 chapters does that really fit into? Is more along this kind of philosophy, isn't it? Yeah. So I didn't do specific research to write the book. It was just the culmination of everything I had learned up to that point. Which, by the way, I hope everybody gets the. The title is ironic.
B
Yeah. It's not an instruction manual.
A
Not at all.
B
No.
A
It's meant to confuse you. And then of course, the challenge was how to end it. You can't just give the 27 and then say the end. Did you get a takeaway from that punchline at the end?
B
I did. Do you want me to talk about it on the show or do you want people to find the punchline themselves?
A
Let's just say there's a punchline at the end. Anybody who reads this book, email me if you want to talk about it. It doesn't fit into what we're talking about on the show, so never mind. Ooh, unless maybe it does and not. Or alright, without going into the actual two pictures at the end for the workplace and not or. So right before we hit record, I mentioned this example of the introvert versus the extrovert where I was comparing notes with a friend of mine that likes co working spaces. Even though she could work at home, she pays money to go to another place to be surrounded by people she doesn't know willingly. And that shocked me. You've got a beautiful home, couch with a view, and you could just sit here and work for free, but you pay money to be around other people. And she finally explained that she gets drained and exhausted if there are no other people around and if she's just in a place that has even strangers that she's not communicating with, just their presence in this room or even in the same building, even if she can't see them, just knowing that they're there gives her energy. And that's why she chooses to go to a co working space. And I went, wow, I'm so glad you narrowed it down to that or put it that way, because I'm the exact opposite. If I'm all alone, I can work indefinitely. There's no friction. I can just go forever if I'm completely alone. As soon as you put one other person in the same building with me, even if I can't see them, but I know there's another person in this building, then part of my brain is thinking about that person and thinking about their well being. And if I'm being a bad person for not interacting with them more or how they're doing or something, and it drains me. So I just keep trying to find scenarios where I'm completely alone with nobody else around, then I can really work and get my work done. And I think, man, workplaces are tough because you have both types in the same workplace. So the clashing views on how to live. The conclusion at the end of the book, in short, is and not or there's no one right answer. It's you have to find the combination, the intersection, the orchestra.
B
That's right. And by the way, that is a central design problem in the experience of work, which is that there are some people who like to work alone and some people who say that they want to work with teams, they want to work with other people. They like the ambience of the buzz around them of people like, I know people who work in sales offices, they're not salespeople, they just like the buzz. And then other people who like to work in engineering offices because they're like mausoleums. So you know these very differences. Well, it's challenging to actually satisfy a team of people where they have such different interests. And so you're right. And that's like a surface detail compared to what you're talking about in how to Live. So listeners, I'm going to read some of the how to Live because we've been hopping around a little bit. But I'm just going to say what some of them are be independent. And I'm going to do them as a bulleted list. So how to live? Be independent. Next one. Commit. Next one. Fill Your senses. Next one. Do nothing. Next one. Think super long term. Next one. Intertwine with the world. Make memories. Master something. Let randomness rule. Pursue pain. Do whatever you want. Right. Now, when I read that one, by the way, while I was interviewing you, just now, while I was talking to you, I was like, yeah, I want to do that one. Be a famous pioneer. And actually I'm going to stop on that. This list obviously goes on for 27 different ones, but I want to stop on that one because it really made me think about where our urges to follow one of these lives comes from, which is, I mean, I suppose they can be taught. In fact, I know they can be taught because one of them is follow your book. I know that one can be taught because churches have taught that one forever. But I almost feel like this is what people use to explain what they are already compelled to do.
A
Yes.
B
So on the one hand, my parents were scientists, and so it was all about discovering the unknown. And so it was about being a famous pioneer. And I have that too. Now. I don't know if I learned it from them, but man, it feels compulsive as hell. So. So anyway, do you feel like these can be learned or do you feel like they're more like compulsions?
A
Do you have kids?
B
Yeah, I do.
A
How many?
B
Two twins. A nice study.
A
Perfect. Are they very different, personality wise?
B
Radically.
A
I love this. Identical twins.
B
No, not identical. Okay, all right.
A
I'm talking way out of my pay grade here, as they say. I'm no expert in this stuff, but we've heard the examples of identical twins that were separated at birth. You know, World War II, whatever, a hospital in Poland. Identical twins. One is sent away to Argentina and one grows up in Germany. And then 30 years later they find these two identical twins and find that they've made the same life decisions all the way through and have the same preferences. They have the same beard, they smoke the same pipe. They both married a woman named Maria. They're both really into model trains, whatever. Even though they grew up unaware of each other in completely different cultures, their DNA seems to have somehow shaped their life preferences. But we've also seen, say, whether it's two kids, fraternal twins, or say, even pets. I used to have two cats, now I have two rats. Never more than a yard apart from each other growing up, but yet have these very different personalities, even though they were treated exactly the same. One is so timid and the other is so brave, and one is so sleepy and the other one's always a Bundle of energy. And so I think our DNA or whatever, our nature. I didn't used to believe in nature, but now I do. I believe that we have a nature that pushes us a certain way, that we can do anything and we can live by any belief system or value system, but some ways are going to feel better than others. And I just had a case of this myself last year where during COVID here in New Zealand in lockdown, I was trying to be domestic. I thought, okay, well, we can't travel. I need to try to be a good domestic person. And I tried that, but it was so against my nature. Every day felt hard trying to be like a homebound, domestic person. And as soon as I got out into the world again, you know, intertwined with the world, I was like, oh, my God, this feels so much like now I'm so full of energy. It just feels so good to be connecting with other people in other cultures that aren't just right here and just. It felt so much better. And I was actually just this morning. Yes, at six in the morning, talking with one of my best friends in Bangalore, India, comparing notes on this, how she can't understand how some people want to spend their lives doing one thing. She said her greatest joy is to do lots of things a little bit just so that they're like, enough. And she likes the broad balance of doing many things. She thinks it would be horrible to pick just one and do it all the way. And I went, oh, God, no, I totally disagree. I love the deeper reward, the deeper satisfaction of going all the way into one thing and proudly cutting off the other options. And every thing I say no to is like dropping a sandbag out of the hot air balloon. It just like sends me higher and higher. And it was funny comparing notes on this because we were saying, like, do you think this is a learned value thing? And like, no, I just think this is just in my nature somehow. And I went, yeah, same here. Like, I think this might be a nature thing. It wasn't just that you grew up reading different books. Actually, we read most of the same books. We can live any way we want. But I think our nature pushes us
B
one direction or three or five, depending. Right. Because there's a lot.
A
Yeah, we light up in some ways of being light us up and some ways of being drain us.
B
And so what I want to explore is this as a listening tool. And I wonder if it has changed writing the book, how you listen when other people say what they're doing. I mean, you just told a story that's like that, where in fact the two things you just described are two things on the list of 27. One of them is change all the time. And one of them is go deep. Go deep in your community, have one job, establish mastery, you know, all those things. So it's very much about stability. And so I'm not even going to say change. Does it make how you listen more perceptive or subtler or different?
A
Yeah, not the book itself, but I think traveling did that for me. I recently figured out how to articulate why I travel. It's because I want to inhabit philosophies. I want to experience a philosophy viscerally instead of theoretically. And so to go to Brazil and be tossed around on the presentism of the Brazilian way of life is a visceral experience. Whereas to go to Japan and experience the deep, almost too much consideration for everyone else, where you're socially rewarded, it's culturally valued to hold back what you're really thinking and only say what the other person needs to hear or what you think is best for the social harmony. That's a completely different way of being. So being in Japan and experiencing that way of life, being in Brazil, experiencing that way of life and giving into it and not judging them as right or wrong. We all instinctively do that at first. We grew up in a certain way. And then you experience another way and you think, ugh, you're doing it wrong, you're weird, you're wrong. It takes a little while to see it their way. I used to think it was so weird that Russians never smile. And finally, like three different Russian people explained to me separately why smiling makes you look like an idiot by their value system. And if you smile, it just shows you're a stupid fool because life is hard and nuanced. And if you're not smiling, it shows that you've understood life, whereas if you're smiling all the time, it makes you look like you're an idiot. That is imperceptive and a fool. And I went, wow, okay, I'm starting to understand that way of seeing things. So even if we're all just working in an office in Ohio, just seeing that we don't have to go all the way to Brazil and Japan and Russia, but just in one small town in Akron, you can have people with vastly different value systems that say, if you value my place here at work, you'll run everything by me. And somebody else would say, if you value my place here at work, you won't bother me with these details. People have These clashing value systems, even just in one location, even if on the outside they look exactly the same and they're both named John, but they can have very different value systems. So I think it does help us to realize that we are not right and they are not wrong.
B
Yes. And I suppose one way I'm going to use it to listen when I ask people about what they want from work is that sometimes there's a say do gap between what people say and what they do. And sometimes what people say, including me, is what I think I should do as opposed to what my nature is. And so your thinking, by the way, aligns very much with my own, which is that people are incredibly diverse. And actually, I have data on it now, which I've identified some 35 different things that people want from work. And I asked people, I turned it into a survey and I sent it out and I asked everybody which of those things they wanted. And out of a hundred people, 120 people, only four picked the identical pattern. So even while you're having differences between two things, like you just named two dimensions. Right. If you add people up into all of the different things that they want, they turn unique really fast. Mathematically, it's not a surprise because 35 different things, there's over a billion combinations you can have. But from a design perspective, it's still a design problem, which is how am I going to satisfy a universe of unique people? How am I going to actually make something that works? And the answer may be you can't, or it may be you set up systems that can't. I don't know.
A
This is out of my realm. But I wonder about the effectiveness of trying to help each person in a workplace realize that their way is neither right nor wrong, that it's just how they like to work, and that they need to understand that everybody else has a different set of preferences, that it's neither right nor wrong, but that's how they like to work. And to understand that, we need to interface between these separate desires.
B
Yeah, I like that as just a true thing, which is your way is one way, it's not the way to live. It's one of at least 27 or whatever it is. I'm going to jump into some closing questions because I know in your particular case this is going to launch into some wide variety of things. A lot of times I do this 15 minutes toward the end of the show, but I'm doing it half an hour before because I know we are going to have a half an Hour of things to talk about. What I ask at the end of every show is, what do you hire your work to do for you? And I'm going to go back and I'm going to say that again a different way, which is your work. This is especially true if you have a job. Your work hires you to do something for it. What do you hire it to do for you?
A
You're just asking for me personally.
B
Yeah, you.
A
Okay. If we define my work as writing these days, then it's the combination of learning myself by diving deeper into something. And I love the empathetic communication challenge of how to best get this idea from my brain to yours. But then in doing so, I have to really. I get better at defining what is this idea that I'm trying to communicate from my brain to yours. And maybe that's why I love writing so succinctly, is because the default way I did this and still do with friends on the phone is we go for hours and hours and hours around an idea, and somewhere along the way, we hit these occasional insights where we go, ooh, wait. So I think what you're saying is da, da, da. And the person will go, oh, wow, I never thought about it like that. I think you're right. That is the way I think about it. And we got there through hours of blather. But because I don't want to put hours of blather into the world, I do the blathering myself or on the phone with a friend or just in my rough drafts, and then I just take out those little tiny gems, those little pearls from all the muck in the oyster, and just put those out into the world. And that's why I'm hiring this work. Funny way to put it. I would do this even if it never made a dollar. I would do this even if I had to pay to do it. I would do this if I was the last person on Earth. Although there'd be a little less motivation to communicate to others. But maybe I'd etch it into a stone tablet somewhere and hope that future aliens would find it. Yeah, I find that the process of figuring out how to succinctly communicate something makes you realize what your own thoughts are. And that's what I'm using my work for.
B
Can we talk a little bit about the phases of that? So there are certain patterns of what people want from work, which are I call narrative patterns. And that's because they have a start, beginning and middle. One thing that people hire their jobs for is to solve Puzzles. Well, that starts off with a knot and it ends with a denouement, you know, where the knot is untied. And in the middle there's this suspension of can I untie this knot? And what's wagered, usually my ego. And it has to be a puzzle that is hard but not impossible. And it has to have incremental wins. And so there's all these things about the ark. Now you've named a couple of them. One of them is I don't know what the beginning is. Actually, I care about that. The end is I found it. This is the kernel of truth that I've discovered through this process in me. How does it start? Actually, I know how it starts. You're driving along in the car and you say, oh my gosh, I have to write his book.
A
But no, but yeah, that was a rare homage, inspiration. But no, usually I think it's confusion, upset, dissatisfaction, unease. You know, a year and a half ago I broke up with a long term girlfriend and I had really mixed feelings about it. I mean, I could tell it was the right thing to do, but it wasn't a hundred percent. It was like 95%. And so that other 5% here, a year and a half later, I'm still looking at that 5%. Friends and I talk about that, what is that? And the lessons Learned from that 5% and thinking about how many of us maybe follow that 5% and plug our ears and close our eyes to shut out the 95% because our parents told us we should be doing this thing. But then I feel this unease inside myself at something not being solved, or I feel like there's more there to look at, or I'm just feeling a little lost or confused and I try to sort out my thoughts. So that's what I first use a diary for, is I just spend hours and hours and hours in a journal. What am I doing? What is this? Why is this upsetting? You know, what's the real point of that? Why do I think that? Well, what if it was another way? Well, what if I did try to do this? Well, when have I done that in the past? And I just ask myself so many of these questions and just write for hours. And then if along the way I come up with a little gem that I think would be useful to others, then I share that. Yeah, that's where it starts, I think, is with the unease.
B
On Work for humans. We've been exploring the principles of multi sided management, which is the belief that work is a product that every Company designs, builds and delivers to employees. Along the way, people started asking how they could put these ideas into practice. So I founded the work design firm Elevenfold to help your company create the kind of work that makes teams feel alive and engaged instead of dead and dull. So you can reduce turnover and build commitment. We're doing something revolutionary here. Learn more@11fold.com that's 111F O L D dot com. That's really interesting. And what's also interesting is that your method is largely internal. And so a part of your experience, which by the way, makes a lot of sense why you might want to be alone for this internal work. A part of your experience is the working your way through it toward the idea, the ultimate kernel. That's really interesting. Do you have any other jobs? Any other works?
A
Yeah, we could talk about programming, but before we do, I just heard an interesting idea yesterday related to this, which is, okay, use the computer program metaphor for a second. Imagine that you are a computer program that's been given an amount of data and you need to process it somehow. And it's a long process. It's going to take you, let's just say, then gonna take the program an hour to compute the data. Protein folding or something like that, compute the data it's been given. As soon as you drop one more bit of data into, has to start all over again. And I think about how many procrastinators I hear from that say, I listen to so many podcasts, I read so many books, and I just don't get anything done. And then I thought about this program. It's like, well, of course, every time you listen to another podcast, every time you take in more data, you've got to start all your calculations all over again because you've just taken in more information. And that's. I think it's so valuable to stop with the inputs when you know that it's important to output. Now at a certain point you think, all right, I know there's always more inputs. I'm just going to stop now. I'm just going to do the output based on the inputs I've got.
B
That makes a lot of sense.
A
Sorry, I don't remember exactly how that fit into what we were just talking about, but it's interesting.
B
Well, no, no, it does. It's that I was saying that your process is internal, and I'm looking at that as sort of a phenomenological thing, which is, what's it like to do that? And how would someone who's designing work for you design it so that you could do that better, so that you could experience that more often. And I say this to you as a musician, which is that experience design is an art and it's an aesthetic pursuit that is followed with an artistic mindset. But usually what you're working on with experience design is not a physical thing, like a sculpture or music. It's the system that people live in.
A
Yeah, yeah.
B
And so now you're having to think analytically about a system and how it's going to create a work experience that people want. So anyway, that's the reason I ask these questions, is because it's from that perspective.
A
Nice Rube Goldberg machine. Usually when I think a system, I think of like a beautifully running engine. The metaphor of an old fashioned car engine and the gears and this and the pistons and it's leading this and like, ooh, what a beautiful engine. It's funny to think of the small version that could start as like a little Rube Goldberg machine. Right? Like, okay, well, when I touch this, it begins. And the ball rolls here, which lands on this, which makes the hammer hit that, and then this. But those things can be fun to make. It can be just a challenge, like putting a car back together. Meaning anybody with a screwdriver and a crowbar can take a car apart. But can you put one back together? And then if you've seen enough cars, could you actually, from scratch, using just a 3D printer and no preset templates, could you go make a car from scratch? And that's what programming feels like to me, is starting from scratch to build a store or a website generator or a login form or whatever. I just start from scratch. I always start with a blank document, no color by numbers, paint by numbers, frameworks and templates. I always start from scratch because that's my biggest joy is it's philosophical. By starting from scratch, it makes you go, what is a store really? What are we really doing here? What's this really about? And I know this is going to sound really shallow, but it felt profound to me at the time, is I was trying to model a cart, a shopping cart, and I was making a cart, a separate thing that at a certain point, when you pay for what's in the cart, it becomes an order. And I was realizing, like, oh, man, then I have to write all those rules all over again. I thought, well, hmm, why do I have to write all those rules all over again? Wait a minute. It's the same rules, isn't it? An order needs to have the Same rules as the cart. The cart needs to know all the rules of the order. I was like, wait a minute, A cart is an order. It's just an unfinished order. An unpaid order is the cart. Oh, my gosh, why didn't I see this before? It's just because we have a different name for it that we call it a cart, but actually modeled in the computer and all the functions that need to know about inventory and, you know, the price has to be above zero. If this and that. It's just an order. Oh, wow. That felt like a huge insight, and it felt philosophical. Even though it's just something as shallow as just a little storefront.
B
I don't think it's shallow at all. At all. I think data models are a completely unrecognized philosophical experience. Yeah, they are absolutely ontological. What is there? It's very deep. And I'm not even sure that those structures exist because of how we think or if they're actually a part of the universe. And I think that when deep data models are close to the part of the universe of what is there. And so I don't think it's shallow at all. It's a small example of a deep thing.
A
Yeah. Thank you. Yeah, well put. It's a small example of a deep thing. I think it's fun to do that with programming almost anything. I mean, obviously it helps if it's something I care about. I don't know if I'd want to be a paid programmer where somebody just says, all right, we need you to get these. You know, move this money from here to there. Now figure out how to do that. Okay. Actually, I have enjoyed lots of that in the past, but it helps if I have a greater motivation all those years. At my Last company, in 2008, I started a company called CD Baby that was originally just me selling my CD on my band's website, but it was at a time before PayPal, before Amazon. Well, Amazon was just a bookstore at the time. And so my friends in New York had nowhere to sell their music. There was literally no business anywhere in the world that would sell your music unless you were on a record label. So they asked me if I could please sell their music on my band's website. And so I did that as a favor for about, I think, four or five friends, until I realized that I had accidentally started a business. So I gave it its own domain name. I made it cd baby.com, and for quite a few years, from 99 through 2006 or so, it was the largest seller of independent music anywhere online. And all those years, I was the sole programmer. I did it all myself. I never had a team because I just enjoyed so much this process of using this sandbox, this playground, to figure out how to make all these things from scratch. Even once we started distributing music to Apple, itunes and Spotify and Yahoo. Music or whatever, each time they'd send me this spec sheet saying, okay, we need to receive your data as such. And I think, ooh, all right, how can I do this? How can I get my data into their data? What's the real point here? What are we really trying to do? Maybe there's a creative solution if I think of it from first principles and what this is really about. It's just fun being able to rethink all of these, but especially if you've got some kind of intrinsic motivation to do so.
B
Here's another closing question. What does your work cost you if
A
you just have a boss? And that's how you see your life as like, I work from 9 to 5, and that's what I do. It helps compartmentalize it. And actually, I'll give a real example here of a sculptor I know here in Wellington, New Zealand, that she was a sculptor out of passion. She's just a very visual person and just liked turning a blob of clay into a ballet dancer. And did it so beautifully that Weta, the company that produced the Lord of the Rings movies here in Wellington, just a mile down the road from me, hired her as a professional sculptor to make all of their figurines. Well, not all. She's one of a few sculptors that do the figurines. So you can buy a, you know, Lady Galadriel this tall that takes her months to make each one. And what blew my mind is that she's been working there for 11 years now. She goes into work every morning at 8:30, comes back every day at 6. And she has not done a single sculpture of her own in the last 11 years since she got that job. And then when I asked her why, she said it's because I'm eight hours a day working as hard as I can, sculpting all day. I get home and I just want to read a book or play some music or just sit with a friend. Last thing I'd want to do is sculpt. I've been doing it all day. I think that is the answer of, what does it cost you? For me, is it because I don't have a boss? And everything I do is for Intrinsic motivation. It means that I'm completely unbounded. So I get out of bed at 4:30 in the morning and I immediately start writing. And then I'll stop to do a call like this. And then when we're off the call, I'm gonna go back to writing and I'll sit there until 11 o' clock at night when I feel my head start to bounce. And then I'll go to sleep for five and a half hours and wake up and do it again. It's obsessive because it's unbounded. I've set up an environment that lets me obsess on getting every little word right because I don't have a boss saying, come on, Derek, we need it. By this deadline, I can obsess. That's what it's costing me. But I choose it. I like it. Same with the solitude. I like it. It has the occasional downside of loneliness, but to me it's worth it. And the obsessing, working 18 hours a day has the occasional little downside, but to me it's worth it. So there's my cost. That's what it's costing me. But I'm happy with it.
B
Yes, it's worth the cost. It's worth the cost. I get an answer more like that from people who have created their own work life. People who have managed to create their own work life will say, it costs me nothing. There's nothing I'd rather be doing. But I think yours is more right, which is, it costs me something, but it's worth it.
A
Hey, you know how to live. That book upsets some people because they want simple answers. I've got just a few emails, people that aggressively disliked that book and said, that book really messed me up for months. And I go, ha, ha, thanks. And they go, no, dude, I'm serious. No, I mean really messed me up. Like you've really harmed my life in a way. Like you started to make me see these other things. Like I now, at every given moment, I feel like I'm always at a fork in the road. There's 27 forks in the road at all times. This is not good, Derek. And I think, well, again, this is, to me, that's a price I'm happy to pay. I think it's fascinating and fun to realize that there's not one answer. There are many, many, many options and none of them is the answer. It's a choice. Again, that's a pain that I like.
B
Yeah. One of the things I thought reading it was that Some people pick one to avoid the cognitive load of having to choose between them because that's hard. And so you pick one. Some of them are still hard, but some of them are not that hard. I mean, just by having slogans that you can say to yourself, you reduce the cognitive load of decision making.
A
Yeah, right. Which doesn't have to be an entire ism. You don't have to buy into an ideology. You could keep a bunch of little slogans and nutshells in your pocket.
B
Yeah.
A
And just use those moment to moment in life when you're presented with any kind of option. You think, I'm going to use this
B
nutshell, this works, which is not the sort of thing you enjoy, hence the book, but that reader. I'm curious. You really expose yourself very broadly to the public. You're like, email me. And you have some very nice filters in front of that. You have to be a human, you have to be various other things. How does that feedback affect your work?
A
It is a constant reminder who I'm writing for. I only write for my existing fans. I'm never writing for the New York Times Bestseller list. I'm only writing for people that have already reached out to me. I read and reply to probably about 50 emails a day and it takes me one to two hours a day. And I enjoy it though it's work. So what did it cost me? 2 hours a day and the occasional like ugh. When people ask me a question like, hello, my name is Abhishek. What should I do with my life? I'm like, hi Abhishek. I don't know. Have you read everything I've written and
B
notice that I'm not telling you what to do with your life? That's not my point at all.
A
Right. But most emails I get are just nice. They're somebody reaching out because they read my book and they liked it. And I can relate to that because most times I love a book, I make a point of emailing the author. Even if they're hard to contact, I go search the web and I try to find their email address. In a few cases I've gone and emailed their agent instead. Same thing. Even when I hear music that I love, I go to the New Zealand Symphony Orchestra and every concert they do, they always include one or usually include one contemporary work by a new composer. If I love it, I make a point of finding that composer and telling them how much I loved their piece because I heard it tonight at the New Zealand Symphony Orchestra. And most of these authors that I contact, and most of these composers never get back to me, and I just forget about it. But every now and then, somebody gets back to me and says, wow, thank you. That means a lot to me that you found me. And I think, oh, cool. Like this person who I just spent, like, 12 hours reading their book, now they're replying to me. That's so cool. That's such a thrill to me that I think, well, I want to be that for other people. Just this morning, before we talked, I answered an email from a woman in Bahrain telling me how much she loves my writing. And then she showed me her writing. She writes on a website, and I really like her writing, too. And she was so thrilled that I replied, and I was thrilled that I know a writer in Bahrain. How cool. And I do actually meet with these people. So when I travel, there's a blog on my website. I could give you the exact URL, but it's Sivers meet chbg, which stands for Chennai and Bangalore. So a year ago, I went to Chennai and Bangalore in India, and I met up with 50 people that I had been emailing with for years, all of them only people I'd been emailing with for years already. And I knew that they would be interesting to talk with. I think I knew over four or five hundred people in Bangalore and Chennai, but I only had time to meet with 50. So I had to go through and look at my email history and pick out 50 people I wanted to meet with based on our email history. And then we meet up in person. And now my best friend that I told you I was talking with this morning is somebody that I met because of that. And who knows? Maybe this woman in Bahrain will be a future best friend. So I do like the real people, connections I get from it. It gives me a huge sense of security knowing that I have reciprocal friends around the world. People that if I found myself adrift in Bahrain or Kazakhstan or Uruguay, that I have people I could call on to say, you know, hi, Jose, my hotel is closed. I don't know if you remember me. We emailed last year. Can I come stay with you? These kind of scenarios have happened before, and I love meeting up with people that have reached out to me. They've told me where they live, we've been in touch, we've emailed many times. And suddenly I find myself in Helsinki, Finland, sitting naked in a sauna with somebody that I'd been emailing with for years. And I just love those moments, you know? So that's why I keep my email inbox wide open and it's really one of the greatest joys of my life.
B
Along those lines, where can people learn more about you and your work?
A
Only my website. I'm just not really into social media. So S I v e r s everything is there, even all of I'm books. And yes, I'd like it if you buy my books. I give all the money to charity, but even if you want to just read how to Live for free, you can sit there and read the 27 chapters for free on my website. So S I v e dot r s it's all there.
B
It is a very easy to use website and everything has a purpose. There's nothing extra. It's really nice. It's really a nice place to go. So thank you very much for coming on the show today.
A
Thanks Dart. I loved your questions. That flew by faster than I think almost any interview I've done in years. There's some that after 30 minutes I'm going, oh God, how long are we going to talk for? This was like I can't believe we've been talking for an hour and a half. So thank you for your wonderful questions and such fun insights.
B
Well, if you ever need a place to stay and you're in Santa Cruz, California and Santa stop by.
A
Cool. Thank you.
B
Thanks for joining me for another episode of Work for Humans. If you enjoyed this episode, please give us a five star rating. Wherever you listen to podcasts and share the show with one person you think would get value from it, believe it or not, this really helps us grow the show and reach more people who want to build the kind of work that people really want. As always, thank you to my producer Jason Ames at 9th Path Audio for his insights insights into content and is high standard for quality. Final note, the opinions shared here are my own and not the views of Google or Cisco Systems. Thanks again for listening. See you next time.
Episode: Why People Want Conflicting Things from Work | Derek Sivers, Revisited
Host: Dart Lindsley
Guest: Derek Sivers (author, entrepreneur, TED speaker, founder of CD Baby)
Release Date: April 28, 2026
This episode explores the fundamental reasons why people want such different—often conflicting—things from their work. Dart Lindsley revisits his conversation with Derek Sivers, whose book How to Live distills 27 mutually exclusive life philosophies, mirroring the irreconcilable ways people approach work and fulfillment. Together, they discuss how beliefs shape actions, the origins of personal and workplace values, and what it means for managers, employees, and company culture. Practical applications for listening and design in the workplace are explored, along with philosophical musings on identity, motivation, and meaning.
“This list obviously goes on for 27 different ones, but I want to stop on that one because it really made me think about where our urges to follow one of these lives comes from...” — Dart Lindsley [27:19]
“You can sit there and read the 27 chapters for free on my website. So S I v e dot r s it's all there.” — Derek Sivers [62:20]
Conversational, philosophical, deeply personal, and lightly irreverent. Both speakers approach the problems of work and life with curiosity and intellectual playfulness, constantly inviting listeners to question their own assumptions and designs.
For anyone designing workplaces, managing teams, or wrestling with questions of life and meaning, this episode is an essential listen—and a reminder that sometimes, the answer is ‘and’, not ‘or’.