Derek Sivers, author, entrepreneur, TED speaker, and founder of CD Baby, joins us for another wide-ranging conversation about parenting a teenager who is ready to leave home, why he moves countries on purpose, why nihilism is underrated, and much more! It is his first podcast after more than a year of saying no to every request.
We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.
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Links
Show Notes
Derek Sivers & Jim O’Shaughnessy
Derek Sivers: Author, entrepreneur, and TED speaker, and founder of CD Baby, once the largest seller of independent music online. Derek’s website
Derek on X: Where Derek shares his writing. Follow Derek on X
Derek’s TED talks: Including “How to Start a Movement,” his most popular talk. Watch Derek’s talks
Jim O’Shaughnessy: Host of Infinite Loops, founder and CEO of O’Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X
Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter
Derek’s Books & Projects
Useful Not True: Derek’s book on skepticism and choosing beliefs because they are useful, not because they are true. Useful Not True
How to Live: 27 conflicting answers on how to live, which Derek calls his masterpiece. How to Live
Hell Yeah or No: Simple mental models for deciding what’s worth doing. Hell Yeah or No
Anything You Want: Derek’s bestselling book of 40 lessons from starting, building, and selling CD Baby. Anything You Want
Tech Independence: Step-by-step instructions and a setup script for running your own server and email instead of depending on big tech. Tech Independence
Books & Ideas Mentioned
Personal Development for Smart People by Steve Pavlina: The book whose idea about seeking surprise sent Derek around the world. Derek’s notes
China’s World View by David Daokui Li: Derek’s pick for understanding the Chinese government’s point of view. Derek’s notes
Maverick by Ricardo Semler: The book behind Derek’s short-lived profit-sharing plan at CD Baby. Maverick
Why Greatness Cannot Be Planned by Kenneth O. Stanley and Joel Lehman: Jim’s reference on why new vantage points change where you want to go. Why Greatness Cannot Be Planned
The Beginning of Infinity by David Deutsch: The book Jim calls a definitive look at how he sees the world. The Beginning of Infinity
Nothing & Everything by Val N. Tine: The book on nihilism Derek recommends, with his advice to read only the first half. Derek’s notes
Highlights
“Someday I’ll be able to spin the globe and every little part of the world will feel like home.”
A major turning point in my life is when I read this little idea deep in a book by Steve Pavlina called Personal Development for Smart People […] he said, no, the extreme way to be surprised is to move somewhere far away from home, to a culture that’s as different as can be, where everyday life will surprise you on a minute-to-minute basis. I’m obviously not quoting that word for word, but that was the idea. And I read that idea and it was like an inception, right? I couldn’t get that idea out of my head. And so about nine months later, I was getting into the process of selling my company, and I realised I don’t need to be here in Portland, Oregon, any more. And I had just broken up with my girlfriend, and I was just completely free and unattached to anywhere and anything. And that idea came back. I said, that’s how I want to spend the rest of my life.
I was almost 40 years old, and I thought, “I’ve spent the first 40 years of my life in the US. I want to spend the next 40 out.” And ideally, I want to keep going to more and more difficult places, and each one, stay long enough until it really feels like home. Until it’s like, this is my place, these are my people, this is absolutely my home. And then move on and do it again. And the ideal, the big lightning bolt of a vision in that moment, was that someday I’ll be able to spin the globe and every little part of the world will feel like home. From Kazakhstan to Peru to Saudi Arabia to whatever. Finland will feel like home. I’ll have friends there. I will have spent significant time there. I’ll feel really deeply connected there before I die.
What a cool mission. So that’s what I set out to do. It was 2008, 2009. I had just sold my company. I went off into the world. I went to London for six months, five months, and it really felt like home. So much home that I almost bought a house there. I was like, “Oh, that’s it, I’m done. This is my favourite city in the whole world. I’m gonna buy a house.” I put an offer on a house. Luckily, that offer was refused, because I had to slap myself and go, “Wait a minute. What am I doing? It’s just the beginning of my journey.” And sure enough, over and over again, over the last whatever number of years it’s been since then, I get to a place, I live there for a while, I feel really attached. So attached that I say, “Never mind, this is it. I want to buy a home here. I’m going to live here for the rest of my life.” And again, I have to slap myself and go, “Hold on, wait. This is what I’m supposed to feel. And when I feel this, it’s time to move on again.”
From Manager to Consultant
So every culture, or even microculture, has its own moment where the boy is considered a man, where somebody goes from childhood to adulthood. Some have a bar mitzvah. In my case, I felt it when, just a few months ago, he flew by himself from Wellington to Auckland to Singapore, did the immigration and everything by himself, flew on the plane as an adult, and I just met him in the airport in Singapore. And I went, “Wow, you did it.” And I just noticed internally, something in me shifted. I’m like, you know, he’s really not a kid any more. He’s a young man now. He’s 14 and a half. Wait, no. Anyway, he’s turning 15 in a few months.
And so in my head, I had to adjust that. For kids, I think parents might need to be more of a manager and help make decisions for them. But at a certain point, you have to change the mindset from being a manager to being, like, a consultant. To put it more bluntly, they fire you as a manager, and you just have to hope that they will hire you back as a consultant.
Edited Transcript
Jim O’Shaughnessy
Derek, you are absolutely one of my favourite polymaths, one of my favourite people in general. And I read…
Derek Sivers
You too. Sorry, I have to interrupt you to say, yeah, you too. So, audience listening: I took a year-long podcast break. Actually, it’s been a little more than a year. I’ve said no to every podcast request for over a year. And then Jim emailed and asked. I said, “You know what, for you, yes.” I really loved our conversation a few years ago. I just adore you and what you’re doing. And so yes, no to everybody else and yes to you.
Jim O’Shaughnessy
Thank you so much. It truly does mean a lot to me. I want to hit you with something you said, because it resonated so deeply with me. And again, I think it’s one of the reasons why we vibe so well together. You said, “I want to make articles, books, websites, music, companies, systems, apps, and especially new ideas.” And I read that and I laughed and I said, “Me too.” But then I thought, you’ve talked a lot about your son, and I’ve been really incredibly impressed with your commitment to him. 30 hours per week, giving him your completely undivided attention. I mean, I don’t even touch that league, and I have three kids. By giving him that 30 hours a week, did you get lots of things out of it as well?
Derek Sivers
Perspective. I think that’s a huge one. When everybody’s freaking out over an election, over AI, over something in the news, over whatever, I’ve got the perspective that my kid and I are out in nature, or he’s fascinated with a book, whatever it may be. It keeps the world events in perspective for me. I never forget what’s most important here.
Jim O’Shaughnessy
Absolutely. And if you could put yourself in his shoes, does he realise how unusual that type of commitment from a father is and was?
Derek Sivers
In his words? He said, “I seem to be the only kid that has a dad.” He said, “You know, all my friends at school, they either literally don’t have a dad or their dad is kind of barely in the picture.” He said, “I’m like the only friend I know that has a dad.” So to me, the thing I wanted to communicate in action, not just words, is that he is more important than anything that might come through any screen.
Jim O’Shaughnessy
I have the greatest of admiration for that. I remember... I was young when I had my first child. I was 24.
Derek Sivers
Wow.
Jim O’Shaughnessy
And my parents were saying, “You don’t know what unconditional love is, Jim. You really don’t.” I was like, “Yes, I do. Yeah. I mean, I have unconditional... Mom, I have unconditional love for you. Dad, maybe not as much. But Mom, certainly for you.” And then I held my son Patrick, and I started to cry, and I realised in that instant that they were right. I really didn’t know what that feeling was. And it’s an emotion. We’re going to get into that a little later, because I think we both agree that, for the most part... well, I think it was... my friend Rory Sutherland says, “We think that our brains are the Oval Office, when actually they’re the press office.” We make many of our decisions emotionally and then pepper them over with rationality. I used to put a GIF up on Twitter that says “Because of reasons.” But your son is making a big move right now. He’s decided to move to Singapore. And you quipped that you’re trying to figure out how to move from being his manager to being his consultant. How’s that going?
Derek Sivers
That’s a new change. So, sorry, to be clear, he’s not planning on moving to Singapore. That was just our moment. So every culture, or even microculture, has its own moment where the boy is considered a man, where somebody goes from childhood to adulthood. Some have a bar mitzvah. In my case, I felt it when, just a few months ago, he flew by himself from Wellington to Auckland to Singapore, did the immigration and everything by himself, flew on the plane as an adult, and I just met him in the airport in Singapore. And I went, “Wow, you did it.” And I just noticed internally, something in me shifted. I’m like, you know, he’s really not a kid any more. He’s a young man now. He’s 14 and a half. Wait, no. Anyway, he’s turning 15 in a few months.
And so in my head, I had to adjust that. For kids, I think parents might need to be more of a manager and help make decisions for them. But at a certain point, you have to change the mindset from being a manager to being, like, a consultant. To put it more bluntly, they fire you as a manager, and you just have to hope that they will hire you back as a consultant.
Jim O’Shaughnessy
And I love that point because it is so true. The idea that it’s horrible for a child not to fire you as the manager. I kind of see that as a failure to launch.
Derek Sivers
Yeah.
Jim O’Shaughnessy
And my wife was more emotional about it than I was, but I was incredibly proud when each of my children (I have a son and two daughters) came in at roughly similar ages and said, “You know, Dad, I really appreciate your advice and what you’re telling me I ought to do, but I’m going to make this choice. I’m going to decide what I want to major in. I’m going to decide where I want to live.” And I was like, yeah. Because, as I mentioned, we were young, right? We were 24 years old. But we talked a lot about how we wanted to raise our children, and the line that we could both agree on was: we want them to be great adults.
Derek Sivers
Yeah.
Jim O’Shaughnessy
And when you make that your watch phrase, right, it precludes all sorts of things that people naturally go to. “My house, my rules.” “Because you’re living under my roof, you’re going to follow my direction.” And that doesn’t make a great adult. That makes a compliant, sheepish, non-curious individual. And in a similar fashion, I have a pretty good memory for anything I read. And so my kids (this is pre-internet for the most part, or early internet) would use me as Google. “Hey, Dad, you know who was the French representative at the Congress of Vienna?” Talleyrand, in case you’re curious. But we had a massive bookcase, and I would just look at them and say, “Look it up in there.”
And we had the whole family together, which doesn’t happen too often, because one of my three, my daughter, lives in California and the other two live out here on the East Coast. And we were reminiscing about it, and all three kids basically said the same thing. When we were... when they were saying, like, well, what did you like about the way... you know, “How did we damage you, first off? But what did you like about the way that Mom and I raised you?” And all three said that what it instilled in them was that voracious curiosity. Because inevitably, if you’re trying to find out that it was Talleyrand at the Congress of Vienna after the Napoleonic Wars, you’re going to run into some other material if you’re actually looking it up in books.
And one of my kids was like, “Yeah, I read for like a couple hours. I was fascinated by the French Revolution, and that led to my curiosity about other things.” And so I think it’s a measure of your success, in my opinion, as a dad, that he wants you to be a consultant now and he’s asked for that, and you’re absolutely willing to go that way. What do you think are going to be the main differences, acting as a consultant as opposed to a manager?
Derek Sivers
I’ve been slowly prepping him for this for years. So let’s take a little example of whenever he has a school holiday. Here in New Zealand they have two-week holidays three times a year and then a one-month summer holiday. So whenever it’s a two-week holiday, I let him decide what he wants to do with it. His mom has a full-time job, but I don’t. So all the school holidays are on me to take him around or do something, or whatever he wants. So there have been school holidays where he says, “I don’t want to do anything. I just want to stay home and do nothing.” I said, “Okay.” And then he’ll pay the consequences of that if halfway through he regrets it and wishes that he would have gone somewhere else.
Jim O’Shaughnessy
Right, I have to stop you, because that goes against every fibre in your being.
Derek Sivers
How so?
Jim O’Shaughnessy
You’ve often said that you want to take action. You don’t want people who just want to Netflix and chill, right? So did you flinch a little when he said that?
Derek Sivers
Oh, of course. Yeah. So I could give more examples. Like, if he said, “I want to go to Europe,” I’m like, “Really?” Or three years ago, he said, “I want to go to China.” And I had only been to China once before in my life, and it was rough. It was not pleasant. It was 2010 and I went to Guilin and it was pretty nasty. And so when he said he wanted to go to China, I said, “Why?” And he said, “You know, Kung Fu Panda. It just seems interesting.” And I went, “All right. You know, in the name of your education, you lead the way. You go plan the trip. You decide where we’re going to go.” And so he did.
And it ended up blowing my mind, you know. So now I love going to China, and I’ve made a bunch of friends there, and I’ve been a bunch of times since, but it was because he was leading the way. But it can work either way. There have been times, even on a day-to-day level, where he will choose to say, “Let’s go have an adventure. Let’s go sleep in the woods, but without a tent. Let’s just bring the sleeping bags and a tarp. I want to sleep in the woods tonight without a tent.” I’m like, “Okay, if that’s what you want.” And halfway through, he really regrets it. In the middle of the night, he’s like, “Dad, I hate this. Let’s go in.” I’m like, “I thought that would happen.”
But the important thing for each of these examples is that I want him to feel the consequences of his choices, so he leads the way. I’m his faithful assistant, but I want him to get lots of experience leading the way, feeling the consequences of his choices first-hand, so that, yeah, he feels the pain of a bad choice or the joy of a great choice of his own, instead of me making those choices for him.
Jim O’Shaughnessy
Yeah. I have some grandchildren who are approaching the tweener category, and I was talking to my son, who’s their dad, and one of the things he said, which was very adjacent to what you said... we were talking about how much you’re going to allow them to make up their own minds and do their own thing. And he said, “As much contact with reality as possible is what I’m going to advocate.” And I was just like, God bless you. Because in this era where everything is just, you know, helicopter hovering, “Don’t do that. Do this.” I mean, that’s a horrible way to turn out a good adult. You are constricting them and putting them in a straitjacket. It’s just, don’t do that. Don’t do that. Let them make mistakes.
Let them come into contact with reality, because that’s understanding the consequence of your own actions.
Derek Sivers
I think one of my favourite parenting sentences was “Broken bones heal faster than fears.”
Jim O’Shaughnessy
They really do.
Derek Sivers
Isn’t that great? Like, you see your kid climbing on the edge of a cliff, and everything in me is just saying, “Watch out.” But instead of, like, “Wait, no, watch out,” I’m just gonna sit and observe, and if he falls, he breaks an arm, so be it.
Jim O’Shaughnessy
Didn’t Hemingway say we are stronger at the point of the healed bone fracture? Something along those lines. We are much stronger after it heals, at the point of fracture. And so I think that as difficult as that impulse, not to... “Don’t do that,” is. I mean, obviously, I have very young grandchildren, too, and, you know, the first couple of years, you’re essentially trying to stop them from killing themselves. But when they get to a point where they are able and capable to make their own decisions, I am entirely in your camp. Let them do that, because that’s the only way that they’re going to be able to really learn, you know, exactly the way the world works. Moving on. I’ve heard that you yourself are thinking about moving.
Derek Sivers
Yes.
Jim O’Shaughnessy
Which, when I first saw it, I was surprised, given what we... In our previous conversations, you were like, “New Zealand is it.”
Derek Sivers
Oh, really?
Jim O’Shaughnessy
Yeah, yeah. You were like, “This is the place. This is, like, the perfect environment for me.” It didn’t surprise me when I read it. I’m like, of course Derek is going to move. But elaborate on that. What...
Derek Sivers
Yeah.
Jim O’Shaughnessy
Why? Why move from New Zealand to Bangalore?
Derek Sivers
Okay, so, context. I should write about this soon. This was a real key moment in my life. A major turning point in my life is when I read this little idea deep in a book by Steve Pavlina called Personal Development for Smart People. It was an okay book, a little too verbose. And this brilliant idea was like 300 pages in, where it said, if you want to keep growing and learning, you need to be surprised. And one of the best ways to be surprised... no, sorry. He said a good way to be surprised is to read a bunch of books about subjects you know nothing about, and try to do things in your community that you ordinarily wouldn’t do, join groups that you ordinarily wouldn’t join, do hobbies you ordinarily wouldn’t do. And he said, no, the extreme way to be surprised is to move somewhere far away from home, to a culture that’s as different as can be, where everyday life will surprise you on a minute-to-minute basis. I’m obviously not quoting that word for word, but that was the idea. And I read that idea and it was like an inception, right? I couldn’t get that idea out of my head. And so about nine months later, I was getting into the process of selling my company, and I realised I don’t need to be here in Portland, Oregon, any more. And I had just broken up with my girlfriend, and I was just completely free and unattached to anywhere and anything. And that idea came back. I said, that’s how I want to spend the rest of my life.
I was almost 40 years old, and I thought, “I’ve spent the first 40 years of my life in the US. I want to spend the next 40 out.” And ideally, I want to keep going to more and more difficult places, and each one, stay long enough until it really feels like home. Until it’s like, this is my place, these are my people, this is absolutely my home. And then move on and do it again. And the ideal, the big lightning bolt of a vision in that moment, was that someday I’ll be able to spin the globe and every little part of the world will feel like home. From Kazakhstan to Peru to Saudi Arabia to whatever. Finland will feel like home. I’ll have friends there. I will have spent significant time there. I’ll feel really deeply connected there before I die.
What a cool mission. So that’s what I set out to do. It was 2008, 2009. I had just sold my company. I went off into the world. I went to London for six months, five months, and it really felt like home. So much home that I almost bought a house there. I was like, “Oh, that’s it, I’m done. This is my favourite city in the whole world. I’m gonna buy a house.” I put an offer on a house. Luckily, that offer was refused, because I had to slap myself and go, “Wait a minute. What am I doing? It’s just the beginning of my journey.” And sure enough, over and over again, over the last whatever number of years it’s been since then, I get to a place, I live there for a while, I feel really attached. So attached that I say, “Never mind, this is it. I want to buy a home here. I’m going to live here for the rest of my life.” And again, I have to slap myself and go, “Hold on, wait. This is what I’m supposed to feel. And when I feel this, it’s time to move on again.”
So I have not been doing that mission as planned, because I was in a one-year relationship with a woman, and after we broke up, she got pregnant, and oops, that’s where my son comes from. And unfortunately, she hates travel, and she’s his mom. So here we are in Wellington, New Zealand, where Mama works for the government in Wellington. And I’ve been here for 14 years, pausing my mission. But now my boy is also kind of one foot out the door.
He really wants to go away to boarding school somewhere. He’s also got this travel lust. He feels like a world citizen. He was born in Singapore. He’s a citizen of four countries. His mom’s from India. We’re both citizens of India as well because of her. So he’s yearning to get out into the world. So that’s the background context. Do you want to ask anything about that before we go to Bangalore in particular?
Jim O’Shaughnessy
Yes, I do.
Derek Sivers
Okay.
Jim O’Shaughnessy
And, big surprise, right, your son... where would he like to go to boarding school? Does he have a particular place that he wants to go already, or is...
Derek Sivers
He just, like... I don’t know. Jim, can you pull some strings somewhere? What do you got?
Jim O’Shaughnessy
The honest answer is yes, I probably could.
Derek Sivers
He just wants to get out of here, honestly. There’s a school in Kobe, Osaka, a Canadian school in Kobe, Osaka, he likes. There’s a school in Tamil Nadu, India, he likes. There’s the United World College in Phuket, Thailand, that he likes. He just wants to get out of here. He just wants to travel.
Jim O’Shaughnessy
He’s got good taste. Those are... I’ve been to all of those places.
Derek Sivers
Wow.
Jim O’Shaughnessy
Okay. Yeah, yeah. Those are all sweet, sweet spots. And you’re going to let him... Are you going to act like the consultant, or are you going to act like the manager when he comes in?
Derek Sivers
Oh, come on, take a guess. Yeah, no, this is totally his doing. His choice. The applications and everything, he’s doing them himself.
Jim O’Shaughnessy
Yeah. What does he think about you wanting to move to Bangalore?
Derek Sivers
Oh, he loves it. He would do it in an instant, too, if Mama said okay.
Jim O’Shaughnessy
Yeah, yeah.
Derek Sivers
He loves it there.
Jim O’Shaughnessy
It’s interesting to me that she hates travel. She seems to be maybe the other... My wife once joked that she made me a regular, normal human being, so maybe that’s what’s going on. It sounds like he inherited your love of travel and novelty and everything else. Yeah. How does Mama feel about that?
Derek Sivers
Totally against it.
Jim O’Shaughnessy
Yeah.
Derek Sivers
So here we are. Yeah, it’s, you know, it’s interesting. We all probably, at some point in our past, especially when dating, have felt this feeling of trying to be who you think the other person wants you to be. And so I think when she met me, and she saw that I was quickly passing through America on my big international journey, she basically brought out that side of herself and said, “Yeah, I can’t wait to leave America. Let’s get out of here forever.” Even though, in hindsight, that was probably, you know, 1% of her felt that way. She brought out that 1% and presented it to me as who she is. So we were dating under that mindset.
And then as soon as we actually did leave America, like, literally as the plane is taking off, she freaked out and said, “I want to go home. I want to go home.” And so it turns out that she didn’t actually want that. She thought she did. And I was critical of that at first, of course, because it affected my plans very deeply. But in hindsight, I realised, yeah, we’ve all done versions of that. You meet somebody and you bring out the side of yourself that matches who they are. Maybe even just in the name of making friends. Yeah. You meet somebody that can relate to a side of you that’s rock and roll, into heavy metal or whatever. So you kind of bring out that one thing.
Even if there’s just one heavy metal band you like, you’re like, “Oh, heavy metal, yeah, I love Iron Maiden.” You bring out that side of yourself in order to have a bond or connection with this person. And then you meet somebody else that’s really into quiet and poetry, and so you bring out that side of yourself. “Oh, yeah, E. E. Cummings is one of my favourite poets.” You know, we know how that feels. And so you can’t fault somebody for doing it, especially when dating. But, yeah, that’s what happened. That’s why I had a kid with somebody that hates travel.
Jim O’Shaughnessy
You know, as you were talking about how we change ourselves for people that we love, I recently reread a thing by Tony de Mello. I don’t know whether you’ve read any of his work. He was an Indian guy. He unfortunately died way too young. He was a Roman Catholic Jesuit priest who got enlightened in an afternoon he spent with a rickshaw driver who was dying. And he said, “Can I just pay you for the rest of the day and talk to you?” And the guy was like, “Yeah, absolutely.” Anyway, that’s a much longer story, but it got me into all of his books. And the thing that I reread was about love, especially for a spouse or a partner. And Tony’s view was pretty hardcore. It was this: if you cannot say to your beloved (and that’s the term he used, “your beloved”), “I leave you free to be yourself, to seek out what interests you, to follow your own passions, to follow your own interests. And if we still are together, that’s lovely, but if we aren’t, that’s going to be lovely too.” He goes, you don’t actually truly love that person if you can’t say that to them. He said, because then what you’re doing is a transaction. It’s conditional. “If you do this, then I will give you, or do, this.” And it made me really think quite a bit about just the nature of intimate relationships, et cetera.
And kind of do an inventory on how many in my own life were, you know, if you were being just really blunt about it, are they transactional or not? And unfortunately, I found that too many of them actually were transactional. Now, lucky for me, I found a lot that weren’t. But it’s natural for us. I mean, you know, we’re memetic creatures, and mirroring, and especially if we really want to get with somebody, or want to date them or marry them, we’re going to make a lot of concessions. And then what happens? I’ve been married 44 years to the same woman, but what happens is, generally speaking, that goes on for the first, oh, seven years, if you’re lucky, and then you start reverting back into, you know, the real you. And that’s when the challenge comes, right? If you can make it through that.
If you can make it through “But you always said you loved...” “Actually, no, I fucking hate it, and I just really don’t want to do X, Y or Z any more.” If your wife or husband can say, “Okay, that’s fine. That’s great,” things are going to look pretty good for you. But I hear you, and it’s actually quite true. I was reviewing our last conversations, and you put us both in the Miles Davis, David Bowie camp, right, where we just want to try new things. A lot of people are happy to just kind of get good at something and then just do it, right? Just, like, same shit, different day. I hate that. I know you hate that. What do you think it is about people like us who just... “No, I don’t want to keep doing that same thing. I want to try new things.”
Derek Sivers
Okay, wait. I’m feeling that discomfort of a loose thread that we didn’t tie up, because I started to answer your question about why Bangalore, and then I got on my long tangent about how I wanted to...
Jim O’Shaughnessy
Let’s do Bangalore and then we’ll come back.
Derek Sivers
I feel I should close that loop. So, yes, Bangalore. Anybody, if you’ve not been there: the city itself is awful. It’s terrible city planning, terrible infrastructure, but the people there are so wonderful. Kind of in the same way that when I met you three years ago, as soon as we started talking, I was like, “Oh, I like this guy. You’re one of my favourite people to talk with.” And that’s really rare, right? So it can happen with places. So to me, Bangalore is the number one spot in the world where almost everybody I meet is such a great conversationalist. I don’t know what it is about that place, but the people I met there are just so fun to talk with. And I just feel such kindred affection and intellectual stimulation. I just love the people there.
So that, to me, is why Bangalore is top of my list of where I plan to live next, as soon as I can leave New Zealand. I don’t mean to make it sound like there is somehow a move against New Zealand. That’s why I had to give the bigger context. When you said, “Why do you want to move to Bangalore? You said you love New Zealand,” that’s why I had to say, yeah, I want to love everywhere. I also loved Santa Monica, living on the beach. I also loved Oxford, England, and I’d probably be living there still if Covid didn’t send me back. I also loved Woodstock, New York. God. I also loved living in Union Square in New York City. I lived there for a few years.
There have been a bunch of places that I loved, and now Bangalore adds to that list. And don’t be surprised in the future if you also hear me say, “Okay, I am moving to Shanghai.” “Okay, everybody, announcement: I am moving to Istanbul.” You know, I hope to continue to move to places and stay there for a while and fall in love and move on. So there’s the context for Bangalore.
Jim O’Shaughnessy
And just to have my end of sewing that thread up: that’s what makes life fascinating, interesting, enjoyable. I can’t imagine not wanting to experience something new, not wanting to learn something new. I would be beside myself. It would really just bum me out. Before I sold my company, an asset management company, I’d really grown tired of just the same speech, the same questions, the same, the same. And so I would try anything to mix it up, right? So I’d make sure I read the local newspaper so that I could change what I was saying to people.
I would look for something interesting that was way outside of asset management, that you could nevertheless weave in, and get people to go, “Oh, I looked at it that way.” But it just got to the point where it’s like, just doing the same thing, it just turns your brain off, I think. Well, yeah, you’re nodding. And I know that you are a very similar mentality to my own.
Derek Sivers
Yeah. Well, I assume that you brilliantly just transitioned back into the next topic that we left, that you were just about to open, which is that... completely accidentally. Oh, really? So some people can just dive deeper and deeper into one thing. This is maybe the comparison we made last time, of AC/DC versus David Bowie. Some people just want to really perfect that one thing, you know? I don’t know Georgia O’Keeffe’s whole career, but it feels to me, from what I know of Georgia O’Keeffe as a painter, she was trying to get deeper and deeper into this one style of painting. Whereas Picasso went through many different phases and tried different approaches. Got famous for his Cubist thing, but that wasn’t his only thing. So it is possible, I think, to not stagnate while still doing one thing.
Some people just have that personality type. They can just dive deeper and deeper into one thing or one place. They can stay in one place. I feel it’s almost a fault of mine that I can’t imagine staying in one place for more than a couple years. But some people get really into one place, really commit, and they’re able to completely thrive and flourish in that one place, or in one career, one expertise, going deeper and deeper into classical piano or whatever it may be. To me, I think my value system, of what it means to live a good life, a full life, is to do lots of different things. I just have this idea of being on my deathbed, looking back and going, “Wow, look at all those places I lived. Look at all those different things I did. Look at all those different lives I lived in my one life.” That’s what I’m aiming for. I want to live lots of different lives in my life. And hence my last book, called How to Live. It has, like, 27 different opinionated versions of “Here’s how to live. Here’s what to do.” “Live for the future.” “No, no, live for the past.” “No, no, live for the present.” “No, no, just get rich.” “No, no, no, do nothing.” And that book was really a reflection of my soul, because that’s how I really think. I want to live many radically different lives in my one lifetime. So that also leaves me very non-judgemental about any given philosophy or approach to life.
I could imagine living a very greedy life for a while, and living a very altruistic life for a while, and living a very hedonistic life for a while, and living a very diligent, prudent life for a while. Like, why not embody all of these different approaches to life, non-judgementally, to see how they feel, and just try them out, to know that you did it?
Jim O’Shaughnessy
Amen, brother. Because I love the addition of the non-judgemental. I think that so many people get it in their noggins that, you know, this is the one true path. If you deviate from this one true path, you’re either a heretic or, you know, an other. I mean, one of the things that’s really bothered me about, oh, maybe the last 10 years is just all of this tribalism, and all of this othering, and all of this labelling, and all of this, you know, God, “If you’re not with us, you’re against us.” And no, try to understand the other point of view. I’m hugely into AI, right? I’ve kept journals since I was 20, actually younger. I don’t have many good quotes in the earliest ones, but from 20...
I have been waiting for AI. I called it synthetic intelligence in a 1984 journal. I’ve been waiting for it all my adult life.
Derek Sivers
Before it was cool. Just say it. Come on, just say it.
Jim O’Shaughnessy
Before it was cool, I really was into it. And so now that I have it, I’m like a kid in the candy store. One of the things that I do is I just routinely take something that I think I’m really vehemently opposed to, and then I go to the large language model and say, “I want you to steelman this point of view.” And then I read it, and I think there hasn’t been a single time when I haven’t thought, you know, they actually have a point with this particular thing here. And it’s, to me, so liberating, because it’s just like putting it in a bin and labelling it and saying “bad” and “I’m opposed.”
Because when you do that, you shut down your reticular activating system and you don’t see any of it. Your brain literally just makes you blind to it. I could send you the text, I could send you the link to the article, and if you had put it in that bin and labelled it as bad (I’m not saying you specifically), yeah, it just goes away. And so I think that the non-judgemental part of it is the key. And, you know, it also feeds into, like, Claude Shannon’s information theory, right? Information theory. Basically, he posits that information is novel. And he says, if you’re looking for the information coefficient, or how much information is in a given thing... and then he gives the example: a poem is filled with information; a political speech has none. Because one is simply trying to get you, through repetition, to go, “Yes, that is the right path. Yes, that particular policy is the one that people like me are going to support.” The people like me, right? And I like people who aren’t like me. I like to talk with people who are completely different than me, because I always learn something. I mean, I had a profound conversation. I was in Miami, and my wife and I were walking along, and there was a very rough-looking character, clearly a member of a motorcycle gang, sitting in the place a bouncer would sit in front of a club. And so I figured he’s the bouncer, and he’s tatted up and he’s smoking, but he’s not smoking, he’s vaping. And this is back when vaping was brand new.
And I looked at my wife and I go, “Look at this. He’s vaping, he’s not smoking a cigarette. I gotta go ask him.” She’s like, “Don’t go. Leave him alone. Don’t go over there.” Anyway, I go. And I’m like, “Hey, I just got to ask, what’s the deal? Why are you vaping and not smoking?” And he’s like, “My old lady said she’d throw me out if I didn’t quit cigarettes. So this is the next best thing.” Anyway, that was our introduction, but we got into, like, a 45-minute conversation...
Derek Sivers
Oh, I love that.
Jim O’Shaughnessy
...about, like, how do you know who you’re going to let in and who you’re not? And he started giving me all the tells for people that he knew were going to bring the energy down, versus the people who would bring the energy up. And actually, I put that into my toolkit, because he was right about a lot of the things he said. And so it’s just like, if you’re willing and you’re able to, those kinds of conversations can be just filled with gems that you yourself are never going to think about.
Derek Sivers
I love that. That’s what I’ve been trying to do with reading books like Understanding China’s Worldview by David Li, which is a wonderful book that tries to explain, from the Chinese government’s point of view, here’s how they see things, here’s why they feel that what they’re doing is the right thing. And you could do the same with any culture on earth that you think is wrong, or the people are bad, or it’s evil, if you try to see it from their point of view. It’s fascinating, because countries themselves, in my mind, are embodied philosophies. Every country, or even some cultures inside a country, are embodying a certain approach to life.
Jim O’Shaughnessy
Yeah.
Derek Sivers
Through governance. And so, for the most part, unless it’s a complete disaster, it is a valid working philosophy. It might be a messy one. It might not be your favourite in the world. But it’s valid, and it’s great to understand somebody else’s working philosophy.
Jim O’Shaughnessy
And what did you take away from... Actually, since the last time we talked, which was three years ago, in ‘23: what would 2023 Derek think... If you could think of an example that 2023 Derek would be shocked that you did in 2026. Like, “Oh, I can’t believe he did that.”
Derek Sivers
Ooh, that’s a good question. Huh. I have one, but it’s one that I promised not to tell, so I can’t tell that one yet. Ask me again in a couple of years and I can tell. But let me think of what I can say. Actually, let’s go back just one year, to 2025 Derek.
Jim O’Shaughnessy
Okay.
Derek Sivers
All right. I don’t know if this doesn’t need to be secret. I really want to live in China, partially for a few reasons. Wait, have you been there? Or where have you been in China?
Jim O’Shaughnessy
I’ve only been to Hong Kong. I’ve not been to the mainland.
Derek Sivers
Wow, okay. Oh, Jim. Okay. Such a huge difference between Hong Kong and even just... you could walk across the pedestrian bridge and you’re in Shenzhen, and it’s just a night and day difference. Amazing. So I really, really like the quality of life in Chinese cities. I haven’t been to the countryside much, but the cities are so nice. It’s almost like the way that we used to think of Switzerland, this kind of top-of-the-Human-Development-Index kind of quality of life, where everything’s amazing, everything’s perfect, everything’s beautiful, everything’s clean, everything’s great. That’s what the Chinese cities are like now. So, number one, comfort. But number two, the kind of thing we’re talking about, you talking to the bouncer: trying to really deeply understand somebody else’s contradictory worldview.
Contradictory to the one that you grew up with, the one that comes naturally to you. Trying to deeply understand that different worldview. As I said earlier, I want to do that by living in places. Not just visiting, not just reading the books. I really want to try living there until it feels like this is home. So China, OMFG. Hell yeah, I want to live in China. So one of the best ways to do that, besides going and hoping that some company hires me to get a work visa, is to incorporate a company. While I was there, I met a Serbian woman who was in the same position. She moved to Shanghai to work for a Shanghai company, but then when Covid hit, the company fired her. But Shanghai was home at that point. She has a husband and a son in school. She didn’t want to leave. And so she found out that you can (this is what I was getting to) incorporate a company in Shanghai for just a few hundred dollars, and pay a local agent to take care of everything, all of the annual filings and renewals and taxes. Total price will cost you about $1,000 a year. And now you, as the owner of a Chinese company, can sponsor your own work visa that turns into a resident visa. So I now...
Jim O’Shaughnessy
Loophole!
Derek Sivers
Yeah, I now have a Chinese name. My Chinese name is Shen Si Wen. And my Chinese company is named, like, Shen Si Wen Consulting Company, where I’m the owner and director. And again, as soon as I am able to leave New Zealand, I will also be moving to Shanghai to live there as the owner of my Chinese company.
Jim O’Shaughnessy
Very cool. Are you going to split time between there and Bangalore, or...
Derek Sivers
That’s my plan.
Jim O’Shaughnessy
Yeah, that’s the plan. I think that for a lot of people listening to this, one of the things that holds people back is this, in my view, sort of irrational desire for certainty, right? The way I look at the world, only a madman is entirely certain, right? I was talking to a colleague before we jumped on here, and he’s like, “Well, there is the sun rising tomorrow.” And I said, “It’s a probability. It’s a very high probability.”
Derek Sivers
I’ve said the exact same one. I love that. I’ve told people before, you know, “It’s not certain that the sun’s rising tomorrow.” And they’re like, “Shut up.” I’m like, “No, I’m serious.” Yeah, okay, thank you. I love that you just said that.
Jim O’Shaughnessy
He goes, “You take things just too far.” And I went, “No, I mean, it’s true. It’s true. It’s a very high probability.” I don’t get worried about it because, again, if it doesn’t come up tomorrow, I won’t be around to feel that anxiety, right? But I think this illusion of control (and I use that term specifically, it is an illusion of control), I think people cling to it and become almost desperate when they can’t feel a sense of certainty about things. And I think that has caused more problems, in my opinion, in a variety of human societies than almost anything else. This idea that... well, you express it very well in your books. Like, is it true? What’s true? Right?
And I have conversations with people who are super bright, super switched on, everything, and then I hit that wall, what I call the wall of their certainty.
Derek Sivers
Yes.
Jim O’Shaughnessy
And I make an effort to try to chip away, but I think it almost is an emotion rather than a rational belief. Am I just babbling here?
Derek Sivers
No. Okay, I want to try to join you in this topic. I’ve never talked out loud about this, so I hope I’m able to communicate this. Okay. I’m picturing one of those little sliders. Say you have a bar graph that’s a set width, and say two thirds of it is blue and one third of it is orange. But you can move the little slider over so it becomes, say, three quarters orange and one quarter blue. Right. Okay. So, to me, let’s say that orange and blue are a desire or a need for certainty, and the other one is the need for uncertainty. I think some people, in their nature, have a desire for more certainty than other people. And I think that’s just a DNA nature kind of thing. Who knows where it comes from?
But just like you have three kids... if you’ve ever had two pets, you know that even little pets have different personalities. Even if they’ve never been more than a few inches apart their whole life, there is this nature. And some people do just have a nature that wants more certainty, and some of us have a nature that wants more uncertainty. But the reason I’m thinking of it as a slider is it can move. In times where, say, you’re feeling sick, like, you get really sick and you don’t want any uncertainty right now. “I don’t want any adventure. Cancel those plans. I just want to be home in my comfortable bed. Never mind this whole adventure. I’m sick.” I’ve felt that, too.
I was off adventuring far away, and then I got Covid while travelling, and suddenly I was just curled up into a ball. It’s like, “I want to go home.” And it was interesting to feel that. I didn’t want to meet anybody new. I didn’t want to try anything new. I just wanted to go back to my familiar, because I was feeling so helpless or weak.
Jim O’Shaughnessy
Yeah.
Derek Sivers
But then that gives me compassion for people who feel that way a lot of the time. And some of them I’ve been very close to, that just their whole outlook on life is like, “I’m barely hanging on here. I’m barely making it through the day. I don’t want to hear any of your crazy big ideas, Derek. I don’t know. I do not want to go to China. I do not want to go to India. I want to go to my favourite restaurant, and I want to watch my favourite show, and I want to go sleep in my bed. That’s all I want.” You know, maybe because they’re feeling weak, they’re feeling a desperate need for more certainty. And okay, I can understand that now. I have felt that myself.
But some people go through life like that. Maybe their slider’s over at 90%, that they want 90% uncertainty, and just a tiny little bit of, you know, “Two weeks a year I’ll go to Europe for a holiday” kind of uncertainty. That’s enough for me. Yeah. But we can’t fault somebody for having that slider in another place, because it might be their circumstances. You could imagine, like the movie Trading Places, that if suddenly they were flipped into a different position, they suddenly win the lottery of life, they’d feel full of confidence. They wouldn’t feel helpless any more. They’d feel full of daring, risk and adventure. And they’d say, “You know what? My slider has moved. I know I used to be that way, but yeah, let’s go to Afghanistan. Give me a rifle. Let’s see what happens.”
You know, they might be full of adventure, the same person, same DNA, but their circumstances can change them too.
Jim O’Shaughnessy
So I actually love that, because you’re absolutely right. Having been there, getting Covid... I was lucky enough to get Covid. I was one of the patient zeros. I got Covid before anyone knew that it was called Covid.
Derek Sivers
Once again, before it was cool.
Jim O’Shaughnessy
Well, this is an area where I was desperate to not be cool, because, literally, I was alone in my apartment in Manhattan, and I called my wife, and I said, “I’ve got the worst flu I’ve ever had. My temperature is 105, and I haven’t eaten anything. Will you please come take care of me?” And she was like, “Let’s see how you’re doing in a couple of days.”
Derek Sivers
Wow.
Jim O’Shaughnessy
And it’s funny that it’s the same illness, because I felt exactly like you did. I was like, “Oh, man.” Normally, if I’m sick, I’ll read a bunch of books, I’ll watch TV, I’ll do something, watch a movie or documentary that I never got to, et cetera, to keep my mind occupied and to, you know, learn something new. Man.
For the first four days of that, nothing. All I had to drink was water. Didn’t eat anything. The fever ultimately went down, and obviously I got better. And then, of course, when I re-emerged, then the lockdown starts. I’m like, “Oh, great. I just spent 14 days on my own, and now we gotta do it.” At least I’ll have other people. But I do... In fact, I think you could take that even further, right? People who are in very chaotic circumstances. I have some people who work for me who are from the Ukraine, and they still have family in the Ukraine. And it’s hard for me to conceive when they tell me the average day of their parent who’s living in Kyiv. And I just tried to model that in my own head.
And I’d be like, I would be so out of there. And so that’s an area where I would move my dial over to “I want much more certainty.”
Derek Sivers
Yeah.
Jim O’Shaughnessy
Yeah. So I like that distinction. I think that makes a ton of sense. You know, the last time we talked, we were also talking about the idea that ideas were wonderful multipliers, but execution is where you create the value. Now, now we have AI. Okay.
Derek Sivers
I hadn’t thought about this.
Jim O’Shaughnessy
Yeah. And one of the things that I’ve thought about is, we can now get a competent first version of a company, of an app, of anything. And then where do we find the scarce part of execution? If we can press a button and have it one-shot a beautiful website that meets all of our specifications, right, so it’s our taste, it’s everything that we want... where is the scarce part that execution brings? Is it in judgement? Is it knowing the audience that you’re making it for? Is it taste? What do you think?
Derek Sivers
My only real answer is, I don’t know. Yeah.
Jim O’Shaughnessy
That’s a great answer, though.
Derek Sivers
I had not thought about this at all. So I could spout some crap off the top of my head, but it would not be worthy of your audience’s intellectual...
Jim O’Shaughnessy
One of the things I’m actually proudest of from my prior asset management career: I had a guy come up to me as I was leaving the firm that I sold and starting my new adventure. We were at a party, and he said, “You know what I really like about you?” And I said, “No.” And he said, “You’re one of the few guys that I ever saw on CNBC who said ‘I don’t know’ so many times.” He goes, “One time I was watching you, and you said ‘I don’t know’ maybe three or four times.” And he goes, “I turned to my wife and I said, ‘I trust this guy.’”
Derek Sivers
Nice.
Jim O’Shaughnessy
Because we all feel so compelled, right, to have an answer. Right, right? And for the most part, Derek, we don’t know yet. The honest answer, if you’re going to be completely candid: “I don’t know. We’ll see.”
Derek Sivers
Do you think it’s related to this? The stereotype of the quiet person that’s sitting at the table full of opinionated people, that hasn’t said anything the whole time, and then when they do speak up, we pay attention, because, “Oh, really? Now they’ve got something to say?” I think pretty universally across the world, people admire the person that only speaks when they’ve got something important to say. But isn’t it interesting that the algorithms reward content creators that spew constantly, whether there’s something to say or not? And I, of course, rebel against that idea. So that’s why people on my mailing list... I have an email list. One of the problems is, if I don’t have anything to say, I don’t say anything. So sometimes they don’t hear from me for 10 months, and then I send out the first email in 10 months.
And sometimes people go, “Who are you?” Like, “Oh, you signed up to my mailing list a year ago. Sorry, I had nothing to say for the last 10 months.”
Jim O’Shaughnessy
You know, I find that is inconceivable to me. It would be inconceivable that you would have nothing to say for 10 months.
Derek Sivers
Well, nothing public to say. I don’t know. I’m still working on my stance on this, but, you know, there’s a bunch of stuff, like I brought up earlier: “I don’t know. Should I move to China? Should I move to Bangalore? Should I start a company in China? Should I do this?” Decisions around building my house. I mean, there’s obviously lots going on in my head the last few years, but it just didn’t feel like it had any public value. You know, it felt like it was all just really internal stuff, and I hadn’t yet distilled or extracted some universal life lesson from it.
Jim O’Shaughnessy
Yeah. Well, and, you know, I was thinking about it too. We are a lot alike in so many regards, but if you have a company, like I do and you did, where you had employees, it can make it a challenge for the people who work for you. By that I mean they’re seeking direction, they’re seeking stability, right? And I’m willing to pivot on a dime, and a lot of people really resist that. And so I wondered, maybe I’m just a horrible leader. Because in many respects, who gets elected, right? And this isn’t just a phenomenon in the United States. It’s kind of everywhere. The person who gets elected is the one who seems the most certain. He or she is the one who... “Yes, of course we’re going to do this and this. This is my programme. And I will never back... I will die on that hill.” Again, I was talking with my colleague earlier, and I personally take the George Patton view of: I want the other poor dumb bastard to die on his hill.
Derek Sivers
Nice. I hadn’t heard that. I like that.
Jim O’Shaughnessy
I don’t want to die. Every time I see “I’ll die on this hill,” I’m just like, “Oh, what a waste. Why? What if you’re just completely wrong?”
Derek Sivers
I like that. You know, if I could do it all over again: at my last company, I was also a bad leader. And I’ve thought a lot about this. I was experimenting and exploring, but still, quote unquote, leading. Okay, sorry. I picture the classic 1800s British explorer with the pith hat on, going in with the machete into the jungles of Africa to go to some land that the British had never been to before. And that’s all about the exploring, right? “Let’s go up here. Let’s try this. Oh, let’s go in that. Oh, that’s a cave. Let’s... no. Okay, we’ll come back out of that. What if we go up here? Nope, that’s nothing. What if we go over here?”
So you and I have an exploratory approach to life, which is fine and wonderful and valuable and fun, but what a pain in the ass to follow an explorer. Imagine the troop of people carrying the chests, following that British explorer into every little crevasse and then back out again. “Oh, no, that’s quicksand. Reverse.” But the way I think it would happen is that explorer would find a great harbour through, you know, exploration number 97. He finally finds something valuable, and so he notifies the Queen: “Hey, we found a great harbour. I think this would make a great port.” So then the Queen appoints a bullheaded leader with blinders on. He goes, “Right, we’re going to that port. Here’s why. Here’s the benefit. Here’s the outcome. Here’s where we’re... let’s go.”
And it’s a straight line that’s easy to follow.
Jim O’Shaughnessy
Yeah.
Derek Sivers
So whereas it was a drag to try to follow the explorer, it’s actually kind of fun to follow a straight-line leader. You know exactly what you’re in for. You know exactly where you’re going. No surprises. Hey, it’s like that certainty-uncertainty thing we talked about, right? Most people want more certainty. So you get a lot of certainty by following the straight-line guy. And then he just goes straight to that harbour and sets up the port there. That’s it. If you tried to say, “Hey, you know what, what if we tried going this way instead?” he’d say, “Shut up.” Yeah. Okay. Now, in hindsight, if I could do it all over again, knowing that I have an explorer, experimenting personality, I would keep my explorations and experiments private. I would not tell my staff about them, because your staff are not your friends.
I mean, even if you’re friendly, they’re not... you know, there’s a conflict of interest.
Jim O’Shaughnessy
Yeah. The agent principal problem.
Derek Sivers
Right. So I would keep my explorations private. And only when I had, metaphorically, found a harbour that could be a great port, then I would publicly play the straight-line leader to my staff and say, “Everybody: made a decision. This is where we’re going. This is how to get there. This is why. This is what you can expect at the other end. It’s a straight line. Let’s go.” I would have to delineate that side of myself. Yeah, I’d make straight lines for my staff to follow.
Jim O’Shaughnessy
Yeah, I did that ultimately with most of the companies that I founded, just because it worked, right? It works much better. It didn’t stop me from being me and doing all of the above. And I didn’t keep it entirely private, let’s be honest. I shared it with several of the people I knew who could handle it. But yeah, that was one of the things that I learned. And then when you put it on yourself, well, of course you don’t want somebody up there: “You know what we’re gonna do? No, wait, no, we’re not gonna do that. Wait, hang on. No, actually, we’re gonna...” You’re gonna go, “Get the fuck out of here, man.”
Derek Sivers
“I read this interesting book last night. What if we tried this?” I get the feeling you’re laughing out of recognition, because, yeah.
Jim O’Shaughnessy
Oh, totally. Recognition.
Derek Sivers
I did that too. It was literally like I read the book Maverick and I was like, “Hey, what if we had profit sharing?” “What if we just split up the company equally between the number of employees? I just read this book last night. What if we tried that?” And like two months later, I’m like, “Never mind, change my mind.” They’re like, “You fucking asshole. You asshole. You told us that the company was part ours.” I’m like, “It was a good book.”
Jim O’Shaughnessy
I changed my mind.
Derek Sivers
Changed my mind. There was nothing... that was quicksand that way.
Jim O’Shaughnessy
The other thing that we talked about last time was the barcode biz. And essentially, just to refresh your memory and our listeners’ memories, that is something that can be very difficult for an individual to do. In the instance of our conversation, it was musicians and barcodes, if I’m correct. But when somebody comes together and collectivises, it becomes very easy for that individual to get what they need. What do you see today as a barcode opportunity?
Derek Sivers
Ooh, I’m biased, because it’s the thing I was literally working on yesterday, this morning, and today after we hang up the phone: my page called Tech Independence. I don’t know if you’ve seen this. The URL is sive.rs/ti, as in Tech Independence. For 30 years I’ve had a very anti-corporate approach to technology. I kind of... I have a punk approach to this. Very anti-business. I hate it when big businesses try to turn tech into something very corporate and over-engineered and awful, full of formalities. Oh, to me, the spirit of the mid-90s, the brand new World Wide Web invention, was this rebellious...
Jim O’Shaughnessy
Punk rock anarchy.
Derek Sivers
Yes, it was, it was like punk tech.
Jim O’Shaughnessy
It was amazing.
Derek Sivers
And so I want to keep that punk tech approach. I like it, and I think a lot of people don’t even know about it. They don’t even know that this is a possibility: to take a punk approach to tech, and to use it as the antidote to the corporate formalities that you’re usually surrounded with. So Tech Independence, at a shallow level, is just teaching people how to get off the cloud. How to delete your Gmail account and run your own mail server. How to delete your Dropbox account, because you just don’t need that if you have your own server. Just get your own domain. It’s 5 bucks or 15 bucks to get a domain. Point it at a server that costs you a few dollars a month.
Here’s how to run your own server, so that all of these, quote unquote, “we’ll do it for you” services can be kicked to the curb and ignored, because you can do it all yourself with a little server for $4 a month. So I ended up writing all of these instructions onto a page on my website called Tech Independence. And version one was a long, detailed “Do this. Here’s exactly what to do. Type this, go here, click that, copy, paste this, put this into the command line. Now make your SSH keys and do this.” And it was like a hundred steps. But if you follow these hundred steps, you’ll have your own server. Version two was me putting 50 of those steps into a script that you could run on your server.
So now it’s 50 steps, and copy this script and just run the script, and it will set up your mail server, your web server, your con... your calendars and contacts. What else? Your Dropbox-style file thing. Anyway, just the last two days I’ve been working on version three, which is taking care of even more of it for you, but giving more education at the same time. So the script will do it for you to save the typing, but it will also give you a plain-text description of what we’ve just done, to copy and paste, so that you can paste it into an AI now and say, “I am running OpenBSD 7.9, using relayd and the HTTP server. I’ve got an SSH account that’s locked in for my user only. The server is hosted here. I have root on this server. And now my problem is that the SMTP mail server is not relaying mail.” So it lets you copy-paste some context for your situation. And then you could ask the AI to either solve the problem, or even, “Can you teach me some more about what I have just created?” Because all I wanted my Tech Independence script to do is to quickly give you the experience of having your own server. I didn’t want to lay out a hundred different options. It’s just very paint by numbers. Go exactly here. Go to vultr.com, get a domain. We’re going to set up the OpenBSD 7.9 server. We’re going to use this web server, this mail server, this concert calendar... I keep saying “concert” by accident. I mean contacts and calendar server.
And just, bup-bup, do exactly this, and within minutes you will have your own server, so that you can be tech independent and shut down your Gmail and whatnot. But I also want people to understand what they’ve done. So I think it’s interesting that AI can make us more dependent on it if we’re not careful, but it can also make us more independent, because with the exoskeleton of AI to strengthen our abilities, we can replace things like Gmail, or replace things like Dropbox, that we were previously dependent on. You can learn how to set them up yourself.
Jim O’Shaughnessy
Yeah, I like that idea, and I completely agree with you. I have this idea that almost everything is a dual use, right? Like, you know, we discovered fire. Amazing, amazing things fire did for us. We started to cook our meat and we got the prefrontal cortex that we hadn’t had before, and that was, yeah, yay, prefrontal cortex. But fire is also incredibly dangerous, and used the wrong way can be incredibly destructive. We didn’t ban fire. We invented fire alarms, fire departments, fire warnings, fire extinguishers, fire everything. And so whenever I hear either of the extremes, right, like, “No, AI is going to bring us into a utopia”... no, it’s not. Nor is it going to turn us all into paper clips, right?
We will learn. When bad things happen (and bad things will happen; they happen with any new and powerful invention or technology), we will learn. “Oh, huh. We better put up, you know, much more of a strong firewall, so this can’t just escape through from its sandbox.” And so I definitely agree with your notion that, depending on the way you use it, it’s either going to dumb you down, because you’ll just say, “Oh, all I got to do is press this button and I get everything I want,” or teach you. And all of a sudden you take all of these... Ken Stanley wrote a great book called Greatness Can’t Be Planned. And he basically talks about the fact that once you get to a certain place, you see things differently, obviously, right?
Because you’re changing your location, you’re going to see things differently and experience things differently. And when you get to that new space, it’s good that you see things differently, because you’re like, “Well, I had intended to go up there, but now I see, oh yes, that’s very inhospitable up there. There’s a lovely meadow over this way. Let’s go this way.” And so I think something where people, like you’ve just described, can use it in a fairly easy-to-use manner, but also learn... Oh, because guess what? The minute you learn that new thing, you’re like, “Hey, wait a tick. I could also do this and this.” And that’s how you grow. That’s how you get new things. Thank God for the tinkerers, in my opinion, right? Because... yeah, no, go.
Derek Sivers
And it’s also just so fun. I’m so glad that you could relate to the punk tech thing I said earlier, because what I’ve had so much fun using AI for lately is to teach me how to replace the bits where I was still dependent. So, okay, since you said the tinkerers, that’s why I had to interrupt here. Imagine this. You have a domain name. Is it osv.llc, right?
Jim O’Shaughnessy
Yeah, that’s right.
Derek Sivers
Okay, so osv.llc. You registered it somewhere, at a domain registrar. And DNS is the name of the thing at the registrar that makes it so that when somebody types osv.llc in their browser or their email client, it knows to send the web traffic to IP address number 123.45.67.8, and to send the email traffic to mail.google.com, or whatever you’re using for mail. So that’s called DNS. And I’ve been online for 30-something years, and I’ve always just used the DNS that was built into my domain registrar. So recently I started moving my DNS to a separate DNS server called bunny.net, which I was very happy with. It’s a company out of Slovenia. I’m very happy with them. They’re great.
But along the way I said, “But I’m still using some external company to do this thing. It’s just low-level tech. How hard could it be?” So I was like, “Dear ChatGPT, teach me how DNS works and how I can set up my own DNS server.” And so it guided me towards creating something that is actually more secure than using some other company, which is called the hidden DNS master. So on a private server that has nothing pointing to it, that’s secret, but at a data centre, I built my own DNS server. Sorry, I’m using a standard, secure OpenBSD DNS server, but basically it’s super low-level, doing it myself, running the same software that these other providers run, but I learned how to administer it myself. So now, for all of my domains, I am the DNS master.
And then I use a company called ClouDNS that just pulls from my master, and they’re like the public CDN, firewall type thing. So the public gets it from them. But I’m the sole source of DNS, so doing it this way, it’s actually way more hack-proof. Worst-case scenario, if somebody hacks into my account at ClouDNS, I go... it’s just a shrug, because I’ve got the secret hidden master that nobody can get into. So that was an interesting low-level thing to learn, because along the way I learned how DNS is working at a very low level. And it was so educational. Same thing with running your own mail server, running your own web server. Instead of just going, “I don’t know, it’s at WordPress somewhere,” you can have the AI... “Hey, show me at a very low level how I can create, like, a hello world type basic service here, and do it myself.” And what I love the most about this (and I just found that I was elated for days while I was working on this) is that it is so non-commercial. I’m just there in a black terminal with the code, and nobody’s pushing, you know, upselling at me, or whatever. It’s just so beautifully non-commercial that it reminds me of that punk tech joy that I got out of this in the first place.
Jim O’Shaughnessy
I love it. I love it. You know, as far as the whole punk thing goes, I look at the scientific method as kind of pure punk rock anarchy. And by that I mean, take no one’s word for it. “No, no, that’s not the correct answer. I think there might be a better answer, and we’re going to keep looking until we find a better one.” I think that it’s a function of just the insatiable curiosity which... back when the whole Age of Reason began, the Enlightenment, there was this thing called the Republic of Letters. Are you familiar with the Republic of Letters?
Derek Sivers
No.
Jim O’Shaughnessy
So it’s really cool. Back in, you know, the 1700s, educated people all around Europe were discovering all these interesting things, and they would write very long letters to one another that got passed on. What would happen is, I would write you a letter and you would think, “Oh, this is a pretty good idea. Oh no, Jim really screwed the pooch on this one. This is not a good idea.” And you would annotate. You would say, “Derek here. No, I don’t think this one works, and here’s why.” And the one you liked, you’d say, “Yes. And what you forgot to mention was this.” And then you’d forward that to another friend who also had the interest. This was a real thing, and that’s how a lot of the news of when calculus, for example, got invented... You know, Leibniz was saying, “I invented calculus,” and Newton was saying, “No, I invented calculus.” And part of that controversy was because all these people were sending letters back and forth to each other. “See what Newton did?” “Well, yeah, but did you see what Leibniz did?” And so that was this explosive, almost Cambrian-like explosion of knowledge, from this interaction in the Republic of Letters. And then the Royal Society institutionalised it. Institutional capture. They formed the Royal Society. And guess what? Societies that want to go on and have authority and all that, well, they’re going to have a lot more rules, they’re going to have a lot more protocols, they’re going to have a lot more “This is acceptable. This style is not acceptable.” And it’s not that at that time it fell off a cliff.
But much of, say, peer-reviewed science today, it’s just so incremental. It’s so... “Are you kidding me?” And so I think that the true scientific method is very much of the ethos that we’re talking about here.
Derek Sivers
I love this. I’d never thought about that, but I think you’re so right. And Richard Feynman is so punk.
Jim O’Shaughnessy
My favourite physicist.
Derek Sivers
But think about it. He was really outspoken in saying, like, “I don’t care who you are. I don’t care what your degree is. You verify your work against the experiment. Show me your work. I don’t even care how beautiful your theory is. Do the experiment.”
Jim O’Shaughnessy
That’s all. If your theory is the most beautiful theory in the world, it’s more elegant than any theory that I’ve ever seen in my life, and the facts say it’s wrong, it’s wrong. Get over it.
Derek Sivers
Yeah. You know, I’ve tried... I want to dive into this punk subject. Anybody listening to this, if you please, email me if you have any insights into punk philosophy. Because whenever I’ve tried to look into it, I just keep getting steered into punk music. And I’m like, okay, well, I don’t like the music. I like the ethos, the ethics, the mindset, the rebellion, the something, the lack of formalities. And I love that you just brought science into this. Science as punk. That’s a beautiful example.
Jim O’Shaughnessy
Yeah, because it is. And that’s what true discovery is. And, you know, whenever you get an institution that wants to capture attention, wants to capture value, wants to capture all of that sort of stuff, a lot of that fun stuff, the stuff that got them there in the first place, stops happening. And that’s a mistake if you want to forever learn more, expand more. You know, I’m a huge fan of David Deutsch. I don’t know if you’ve read his book.
Derek Sivers
Yeah. Okay, wait. You know what? We’re deep into the podcast. Who knows if you... I dated his goddaughter in Oxford. And so every night after our dates, I would drop her off at David’s house. And so...
Jim O’Shaughnessy
Oh, my God.
Derek Sivers
I didn’t meet him, because we broke...
Jim O’Shaughnessy
Not an envious person by any stretch of the definition of the word, but that makes me envious.
Derek Sivers
I just assumed that... I thought we were going to keep dating. I liked her a lot. I thought we were going to keep dating, and I just assumed that I would meet him. But then we broke up and I didn’t meet him, and then Covid hit and that was that. Another reason I loved living in Oxford. Sorry, I just have to smile with sweet memories when I hear the name David Deutsch.
Jim O’Shaughnessy
His book The Beginning of Infinity is a sort of a definitive look at how I look at the world.
Derek Sivers
Nice.
Jim O’Shaughnessy
I read it when it came out in ‘12, and then I reread it in ‘23 or ‘22. I can’t remember. I got so much more out of it the second time.
Derek Sivers
Oh, good. I should read it a second time. I really also loved it the first time.
Jim O’Shaughnessy
It’s worth the second read. Let’s do something fun. I’m going to put you on the spot, for once.
Derek Sivers
Okay.
Jim O’Shaughnessy
I love the fact that you take... I am, right now, just to give you context, I am writing... I’ve written four books, but they’ve all been non-fiction books. So I thought, you know what? I’ve always wanted to write this, and this is true. I’ve always had this idea for a fictional thriller-type novel, for the last 35 years, and now I’m writing it. And the first thing I learned was fiction’s got hands. By that, I mean it’s a hell of a lot harder than non-fiction. And I always admired you for the care you gave each sentence, right? You would write a sentence and then you’d write it 10 different ways. Can I put you on the spot?
For our listeners and viewers, give me a sentence, and then show me all the ways that you got to that sentence from other ones. If you could do it from memory.
Derek Sivers
Ooh.
Jim O’Shaughnessy
Because you’re so good at this.
Derek Sivers
I wish I could. I don’t remember the final sentence. Damn it. In my book How to Live... I just don’t have it right here, man. If I was one of those guys that... if I was sitting at the computer while we were talking, I would just pull it up. But okay. But I remember there was this one idea that was a combination of something I read in a book, that then was combined with a conversation with a friend, and then enhanced by a conversation with a different friend. And all these sources together had this big idea. Kind of like you and I have talked around a few ideas, like straight-line leadership, or punk tech, or the scientific method as punk. We’ve talked around an idea.
But for my book How to Live, I was writing so succinctly, like poetry, that I just kept... I took a paragraph and made it four sentences, and I took those four sentences and made it three. And I took those three and I made it two. And then I took that two and I made it one, but it was still too long. And I cut out all the unnecessary words. And finally, what I was left with was this one sentence. It was like ten words. And I looked at that going, “God damn, that really does sum it up.” What a nice feeling. And even the choice of words: I’m constantly reading things out loud and choosing the words that sound nice in the mouth, that roll well off the tongue.
Because ideally, I still have this songwriter in me that wants things to be catchy. So with my newest book, Useful Not True, the goal was to make it so catchy that, in theory, if I were to practise for just, say, a few weeks, I would be able to stand up on stage and, word for word, tell you the whole book from memory. Because it’s only 88 pages. The average chapter length is 22 sentences. And I should be able to memorise that book word for word, and stand on stage like one of those people that puts on a one-man show on Broadway. I should be able to do that book word for word.
And, audience, we paused for me to go find the sentence that I was so proud of: “Pain’s power relies on surprise. If you expect it, it’s weaker. If you choose it, it’s gone.”
Jim O’Shaughnessy
Wow.
Derek Sivers
It just made me so happy. That was, like, hours of conversations and rambling ideas. Yeah. “Pain’s power relies on surprise. If you expect it, it’s weaker. If you choose it, it’s gone.” And that’s in the context of the chapter called “Pursue Pain”. So the whole idea is, if you decide to deliberately follow the painful path, because you know it’s better for self-improvement, or learning, or greater rewards, then the pain is gone, because you’re choosing it.
Jim O’Shaughnessy
It’s like Jung saying that as long as you try to fight your demons, you will only strengthen them.
Derek Sivers
Oh, and Oscar Wilde said, “The way to resist temptation is to yield to it.”
Jim O’Shaughnessy
Yield to it. I love Oscar Wilde.
Derek Sivers
Yeah, he’s always good for the classic quip like that, reversing the expectation of the line. But, I mean, so, writing fiction: are you following any structural best practices, like an outline that they say makes a great story? Or are you just fully immersing in the...
Jim O’Shaughnessy
I read Joseph Campbell at length. I read a lot about how to write good fiction. I have kept journals forever. I’ve been a writer all my adult life, so... But I’m not following the hero’s journey. I’m immersing. I’m immersing after having read, or in many cases reread, those books. And I figured, since we have the publishing company, I’ve got an amazing group of writers working for me. So we’re also using a writers’ room, and we’re putting AI editors and writers in the writers’ room. We want to give the whole thing a whole different take. We’re going to try a very different way to get a really cool story. And it’s been ridiculously fun, because when you start, you’re just an idiot. I would have my colleagues say, “Well, what do you think of this?” And, you know, they try to be nice. It’s like, “Well...” So what I finally did... we also have our own AI stack. We have our own hardware, our own software, everything. And so it’s not nerfed. It’s much more helpful than some of the commercially available ones, because you’re not lobotomising it. Anyway, what I found the AI was best at was actually criticism. So I would put a chapter in, and it would give me all the pluses and minuses. And then I’m like, AI is... even our own AI is a bit sycophantish. So I wrote a very long prompt that created one of the best-educated, most erudite critics, who is going to hate every chapter that I write. And Derek, I gotta tell you, that was the best of any of the feedback I got. Because it was vicious. It was beyond vicious.
And at first, you don’t get mad, because it’s a machine.
Derek Sivers
Yeah.
Jim O’Shaughnessy
If a human being that you were fond of sat opposite you and said those incredibly vicious things, you would be so hurt that you just couldn’t function, right? When it’s a machine, you just read it. You’re like, “Well, that’s kind of picky. That’s kind of...” Then you read it again, and then you’re like, “It’s absolutely right. I’ve written this character completely in the wrong tone. I’ve got to completely rethink the way I think about this.” And then it just started getting better and better. So my vicious critic prompt in AI proved to be, like, the absolute best feedback I got anywhere.
Derek Sivers
I love this. I wonder how the AIs... I could totally imagine them having the structure frameworks in mind. I’ve never written fiction, but I find it fascinating. I’m a film buff. I didn’t even realise this about myself until a film composer told me what a film buff I am. I’ve read maybe three or four of these books now that talk about story structure and film structure, and how to make a plot that keeps you hanging and keeps you involved and makes you feel like you’ve arrived in a different place than where you started. And who is the protagonist? The protagonist is the one that changes the most. You know, things like that. And I find them fascinating, even though I’ve never used them. But I have written over 120 songs with the same approach. You could call it formulaic, but it’s taking the lessons from what have made the best songs so good, and using those techniques to write your own song, using them as inspiration. And so my favourite phrase about this is “Restrictions will set you free.” If you’re just given a blank page and someone says, “Make something. Go,” you’re stuck. But if somebody says, “Okay, start here, then after this change to that, but then double-time it in the middle, and then go to this, and then end higher. Use these three instruments and these six notes. Go.” Well, now those restrictions set you free.
Jim O’Shaughnessy
Absolutely.
Derek Sivers
Because now you’ve got so many ideas sticking within the structure. So if I was to write fiction someday, I think I would probably get so inspired to write, like, 10 different stories using some given framework, that ideally nobody would see the framework underneath.
Jim O’Shaughnessy
Yeah, definitely. And I’m lucky, because we’re using this writers’ room approach. I have some great people for structure, just as you’ve been outlining. And they’re reading it now, and they’re like, “Okay, what you... you had a... the cortisol spike. That’s a thriller. And then it spiked again in a different thing, and it’s the same chapter. No, no, no, no. You got to let each of those spike independently. You got to make this two chapters, not one.” And basically, I was saying the same thing, except in one chapter it was two cortisol spikes, and that was somehow less jolting than the big one in the first chapter and the big one in the second chapter. So I’m very lucky to have a very talented team that can give me that kind of feedback.
But it’s fun because, you know, it’s something that I had wanted to do since I was in my mid-30s, and now I finally got a chance to do it, so that’s exciting.
Derek Sivers
I love this.
Jim O’Shaughnessy
Another thing you did for your book Useful Not True was you studied philosophy for two years, and I love that. I love philosophy. I took a few classes in it, but I’ve read most of the major philosophers. And what I wanted to ask you is: after you studied the philosophy, what could you be confident in saying... that you were fairly confident of an idea before you started studying the philosophy, and then after you did, you’re like, “Yep, that one doesn’t work at all”?
Derek Sivers
I actually have an anti-answer for you, because it made me less confident about my definition of true. I’m still a little surprised that I only agree with the nihilists. And nihilism has such a bad name. It’s used as almost synonymous with Satanism or something. When people say, “Well, you don’t want to be a nihilist,” you know, they just use that as the worst thing that anybody could be. But there is a beautiful little book called Nothing & Everything. Actually, sorry, the first half of the book is beautiful. The author uses a pseudonym, Val N. Tine. And the book is split into two halves. I don’t know what happened in the second half, but the first half is so beautiful and so well written, and just had me yelling out loud as I was reading it, like, “Yes!” And then it’s like, “Part Two,” and I’m looking at this, like, “Ew, what spilled on the page here?” Anyway. But this definition of true that I find most useful... because of what you said earlier, your biggest problem is other people’s certainty. When they get so damn certain, their mind is closed. “That’s it. This is a finished matter, not up for discussion. That’s it.” To me, you should reserve that only for things where there really is no other answer. A square has four sides, and that’s that. There is no other answer. That’s certain. That the sun is going to come up tomorrow, you know, like you said...
Jim O’Shaughnessy
Highly probable.
Derek Sivers
Not certain. Let’s reserve the things we call true for only the things where there is no other answer. And unfortunately, even pragmatism, which a philosophy professor steered me towards... I described it to her, and she said, “It sounds like you’re talking about pragmatism.” So I went and read five different books about pragmatism, and unfortunately, no. I wish that my thoughts would have fit into the philosophy called pragmatism, and I would have said, “This is the school of thought I subscribe to.” But no, it also wasn’t quite right. So, sorry, the only answer to your question is that it made me more uncertain. Which I guess was ultimately my point. I think that Useful Not True is ultimately a book about scepticism. It’s about doubting everything.
Jim O’Shaughnessy
Well, sure. And I wrote a thread on Twitter about my own journey there. And I said, when you go through all of the thinkers, the philosophers, et cetera, most people end up at nihilism. And one of the things that I learned, at least in my life, was you’ve got to walk across the bridge of nihilism. And by that I mean, you get to the other side and you realise, if life has no external inherent meaning, if there is no truth with a capital T, how lucky are you? You’ve got a blank canvas. You can paint your life on that blank canvas. You can make an incredible life, with meaning, with purpose, with all of those things that you decide. It’s entirely bespoke to you. But you gotta walk across the bridge.
Derek Sivers
I love that. You might, you know, even just for the smile and the joy... I don’t know if it’ll teach you anything, but this little book called Nothing & Everything, by...
Jim O’Shaughnessy
I wrote it down. I’m gonna get it.
Derek Sivers
Okay, good. And just stop at the second half. When it gets to the second half, just call it done. But yeah, it’s the only book I’ve ever found that fully dives into what you just said.
Jim O’Shaughnessy
I just love talking to you. I hope I can hooks you on yet again, because I didn’t get to half the things I wanted to talk to you about. You are such a wonderful conversationalist. I always really enjoy talking with you. It’s just so much fun. A lot of people... I don’t know if this happens to you, but a lot of people sometimes look at me and they’re like, “What?” Yeah, we’re weirdos. Yeah.
Derek Sivers
I think last time, didn’t we do a Part One and Part Two right away? So I’d be up for that, if you’d like to.
Jim O’Shaughnessy
Oh, I would love to. I will have Ena send the invitation for the second one, and we’ll get this one out as quick as we can.
Derek Sivers
All right, audience, we’ve just turned this into a Part One, Part Two to be continued.
Jim O’Shaughnessy
Part One, Part Two to be continued.
Looking forward to the conversation. Laughing at the Derek’s heat miser background.