The Person You Want to Be
host: Eric Teplitz
childhood influences, luck and opportunity, inspiration and creativity, spiritual beliefs and questioning
listen: (download)
watch: (download)
Transcript:
Eric
Derek Sivers, welcome to The Person You Want To Be.
Derek Sivers
Thanks, Eric. I really appreciate it.
Eric
I’d like to open this actually with a quote from your first book, Anything You Want, because I think it in a way sums up your philosophy still to this day, even though the book was originally published in 2011. So here’s what you wrote, “Most people don’t know why they’re doing what they’re doing. They imitate others, go with the flow and follow paths without making their own. They spend decades in pursuit of something that someone convinced them they should want without realizing that it won’t make them happy. Don’t be on your deathbed someday having squandered your one chance at life, full of regret because you pursued little distractions instead of big dreams, you need to know your personal philosophy of what makes you happy and what’s worth doing.” No question there. I just thought that was a good opener. And to me, that really kind of sums up the sum and substance of your work. You are always challenging norms. You’re always even questioning your own preconceived notions of things and trying to see things from another angle, another perspective, and trying on different beliefs and outlooks, which is endlessly entertaining. For those of us who read your work. And it’s endlessly thought provoking as well, because it naturally makes us, as your audience or readers or listeners reflect on how this may apply to our lives. How are we not seeing things in ways that might be more helpful? So for this interview, I like to begin at the beginning and have you think about your earliest childhood memories. And specifically what I’m looking for here is your earliest sense that you had as a kid of who it was or what it was you wanted to be, maybe what you felt you were here to do or what you were naturally drawn to. And if you could also provide a little bit of context about your childhood environment in which you grew up.
Derek Sivers
Sure. I think my earliest thing worth mentioning is I was super into cats that when I was five years old, we got a cat named Sally and I got so into cats for the next five years that when I was 9 or 10 the teachers called my parents into school and said, “We’re a little concerned that all Derek talks about and writes about and makes about his cats.” And any time there was a project I would make a cat, they ask us to write a story. I write about cats. They ask us to draw, I would draw a cat and my parents just said, “Yeah, he just likes cats.” But it was like my obsession for five years. I got super, super, super into cats and I would tell you anything you wanted to know about cats. And then when I was 11, maybe ten, my dad brought home a computer. It was one of the first personal computers, the RadioShack TRS 80. And I got super into computer programming for the next five years. Forget cats. I got so into computer programming for five years. I was just head down. I just obsessed on this thing. I found it fascinating. All I wanted to do was program computers until I was 14. And I heard Iron Man by Black Sabbath. And I went, “Ooh, I want to make that sound.” And a friend of mine told me, “That’s an electric guitar.”
Derek Sivers
I was like, “Yeah, that’s what I need.” So I got an electric guitar when I was 14, and then that obsession lasted for 15 years from age 14 to 29. All I cared about was music. I didn’t want to do anything else but music. Head down on that craft. I just obsessed with how to be the best writer, guitarist, performer, even producer. I got a home recording studio and just learned how to record my own music myself and wanted to be the best at that I could be. At the age of 29 is when I started CD Baby. So then for ten years I was head down focusing on making that the best it could be and helping musicians. And since then you can say, at age 38, 39, I sold CD Baby, and now it’s been 15 years or 14 of focused on seeing the world from another perspective. That seems to be like my ongoing mission now. So I think the going all the way back to when I was five, the common thread is I tend to get really into one thing at a time and it feels like an unfinished project, you know, like you can’t just leave something unfinished. But then because I’m so into it, it just always feels unfinished. And so for years and years and years, I’ll just be into one thing. Yeah. That really guides my life and defines who I am.
Eric
I had a couple of thoughts listening to that. The first was, I don’t know if you ever saw the film Adaptation, but--.
Derek Sivers
Oh my God are you going to quote the fish line?
Eric
Done with fish.
Derek Sivers
Wow. I can’t believe you just quoted that. I was thinking that as I said it. Yes. Dude, when I saw Adaptation, I got such a great laugh out of that where he was just like, “Fish, fish, fish, man. I was just raising fish. I had this kind of fish. And one day I’m like, fuck fish, done with fish.” I was like, “Yes, my man. I can relate.” I’m amazed that you just quoted that. Nice.
Eric
Yeah, that definitely is what I thought of. And it is interesting, right? There are times in life where we just don’t look back. We’re just done with something. We move on and there’s literally no looking back. But I know I’ve had I’ve had that experience, but I’ve also had the experience of having something still sit in my psyche as feeling unfinished or unresolved, even if I may have gone on to do something else. Have you had that experience?
Derek Sivers
Well, I did come back to computer programming many years after, you know, I was 14. I still occasionally think about making music, but I’ve just found over and over again from experience that it’s like my fifth or sixth priority now, which means it just doesn’t happen. You know? So I’ve bought a nice musical instrument and had it sitting right next to me and I just don’t pick it up. It’s just not my mode of expression anymore, you know?
Eric
Yeah. Was that difficult to accept or?
Derek Sivers
Not difficult, just slow. I keep doing it. Including a month ago Ableton came out with an instrument called the push for number four, which has aftertouch on the pads and each pad has a bend up, down, left and right. And I always thought that the Ableton push or similar kind of touch pad instruments, are the instrument of the future because it’s so open and definable. No need for the piano style, white and black keys, no need for this kind of diatonic scale. I really like the eight by eight grid. In fact, I think if I were to recommend one instrument to a new young musician, I’d say start with this, like master this instrument. Because if you get great with the pads, you can do anything. But I was like, except, you know, you can’t bend a string. You can’t get the aftertouch of like a flute has or you can blow. And then but then the Ableton push for added aftertouch in the bends. I was like, “Ooh, now it really is the best instrument.” So it’s like, I want to get one. Then I was like, “Wait, Derek, stop, stop. You’ve done this before. It’s going to be your fifth or sixth priority. You’re not going to touch it. Just stop. Just be glad it exists.” So, yeah.
Eric
I hadn’t even heard of that instrument, so I’m going to definitely read, search it and look it up. But that requires the word that comes to my mind. Is maturity, right? To know yourself well enough that you know you’re being honest with yourself. Yeah. Um. You mentioned that you came back to computer programming when the show cats came out. Did it hold any appeal to you at that point? Oh, no. God, no.
Derek Sivers
Oh no, no. God, no. Cats are fine. So are dogs. So are most animals. No, no fascination there.
Eric
But now you have pet mice. I understand.
Derek Sivers
Oh, yeah. Yeah. Mice are a surprisingly good pet. They’re easy. They’re cute. You can stick them and stick one in your pocket and take it out for the day.
Eric
Okay. So there are so many directions that we can go in. And so I’m going to just do my best to pick and choose some and see where they take us, knowing that we likely won’t get to everything. But just randomly. I’m going to ask you about the subject of luck. Because I think this is really interesting. And Kevin Kelly he put out a book recently about advice just like a lifetime advice that he’s accumulated. And in various interviews I did one with him, but I also listened to so many that I can’t remember whether he said it in mine or elsewhere, but he said that as he’s gotten older, he has realized increasingly how lucky he’s been and that initially in his younger days, he felt that all of his success was very much well deserved and earned and all of that. But with the passage of time, it occurred to him or he realized how luck played a part in his journey because he noticed that there were people that worked harder than he did or maybe were more naturally gifted than he did, or both, and yet maybe didn’t get some kind of lucky break that he may have gotten.
Eric
I think that’s a very interesting subject. And I want to quote you from a couple of things you’ve written about that mention luck, and then ask you specifically about your perspective on luck. So you wrote in Hell Yeah or No. You said, “After I sold my company I felt ready to do something new. So I started to learn. But the more I learned, the more I realized how little I knew and how dumb lucky I had been.” Another quote from--. This is actually you did a blog post that was called “Ancestors Luck and Descendants”. And in that post you say that a friend had asked you why you’d been successful in life and you said, “I’ve just been ridiculously lucky.” And he said back to you, “No, your success has come from choices, not luck.” And you said, “I disagree. What about being born in America? That wasn’t a choice. That’s luck.” So I’m curious to know how you view luck, what your perspective is on it. And then, more practically speaking, how can we become luckier? Is there anything we can do to influence that X factor in life of luck?
Derek Sivers
Yeah, I think about place a lot. It feels like there are places where luck happens. You will find more opportunities in New York City than you will in Uruguay. Uruguay is a gorgeous place, nice quality of life, but there are less business opportunities there or just synchronistic. It doesn’t even have to be business opportunities. There are less people there. There’s a less variety of people there. There are things that can make luck more likely to happen. So being in a place where lots of things happen is one. But then of course, you have to go pursue things and do things and go meet strangers. Say yes to weird things, get out of your existing circle of friends and jump into opportunities. I used to just go answer classified ads and just bring my guitar and show up to auditions, sessions. I would say yes to anybody that was looking for a musician for anything. Even if they said, we need a jazz piano player for an art opening, I’d say, “Yep, I can do it. When is it? In three weeks from now. All right.” So the next three weeks, I would quickly study jazz piano. And then I would keeping in touch with people. So as to get the aftershock because I found that a lot of opportunities happen immediately after you’ve randomly met with somebody. You know, you bump into somebody on the street, you have a conversation about something, and then the next day that person calls you and says, “Hey, a friend of mine over at HBO is looking for something.” These things often happen the day after you bump into somebody because now you’re on their mind.
Eric
Their mind. Yeah.
Derek Sivers
Yeah. So I found that keeping in touch with people creates luck. Let me think. What else. And then okay, so you cut off the story of Ancestors, Luck and Descendants. After I told him like, “No, no, it was just it was luck.” Oh, no, sorry. I said, “What about the luck of being born in America? This prosperous country.” His response blew my mind and was actually the reason I wrote that article. He said that wasn’t luck either. He said, “Your ancestors made that happen. They left Poland or Sweden or wherever they were from, leaving everything they knew behind to sit on a boat for three months and endure hardship to get to the land of opportunity so that their grandkids could have a better life. And you are the result of that.” I was like, “Ooh, that’s a really good point.” Because then I started thinking, What can I do to make my kid’s life or my future grandkids life more lucky? So for example, helping your kids have a second passport so that if the country they’re in turns sour to have the legal right to be somewhere else, to have another shot. You know, like I’m sure Germany seemed like a really nice place in 1912 or I should say maybe 1908. And then things can suddenly turn sour. Yeah, even if you look at the documentary called Persepolis, it’s actually a cartoon, but it’s kind of a documentary on what happened in Iran in the 1970s. And a friend of mine is Iranian, and Iran was a wonderful place to be in 1971. And then suddenly in 1976, things turned bad.
Derek Sivers
So it could happen to any of us anywhere. It happened to Argentina, happened to a bunch of places. So getting a second passport for your kids, making sure they have the legal right to be somewhere else, can help their luck in life to give them the right to escape. Yeah. So I do think multigenerational now but I think the most actionable one that most of us can do now is to reach out. To initiate new connections, meeting new people, signing up for courses. That’s another one that had a huge impact on me is a one music business class called. What was it called? I remember the teacher’s name, Peter Kenickles. But this is long ago. He’s not doing it anymore. But he had a weekend course like showed up to a hotel conference room basement on a Saturday, Sunday and took a two day course for $99 from Peter Kenickles in New York City. He’s from New Hampshire, but he did the course in New York City. And that’s where I learned about the college market and how to get gigs at universities. He basically spelled out the recipe of how to do it. And I was like, “Oh, man, this is great. I’ve never heard anybody talk about this.” So I ended up making probably a quarter of $1 million off of gigs in the college market for the next six years, all because of that $99 seminar that I jumped into. So I was constantly pursuing little things like that. And I think that’s where most of my luck came from.
Eric
Interesting. Yeah, the intergenerational thing. Of course, you know, you could still argue back. Well, I didn’t control the decisions of my ancestors, but I can decide, as you were saying, to be an ancestor that can do things to help future generations get lucky, as it were. So when you were 14, you said inspired by Iron Man, Black Sabbath, the electric guitar sound. You got yourself an electric guitar and what was your approach? How did you go from, “Okay, this sounds so cool, I want to make that or something like that”. Where did you begin to become a great musician? What were the things that you did specifically in pursuit of that vision that you had for yourself?
Derek Sivers
I signed up for guitar lessons, and I took weekly guitar lessons but I think when you’re obsessed with something it just becomes everything. There’s no one thing. So I started reading every issue of Guitar Player magazine and Guitar World magazine, which were the things at the time. This is before the internet. You know, I went to the bookstore and found every book I could about music, interviews with musicians. I sat there trying to imitate all of my favorite records. I would read interviews with musicians and whenever they mentioned some influence of theirs, I would go find an album by that person that influenced them, and I’d get to know that person’s music. And even just listening to the radio to turn myself on to new things. Yeah, I just did everything. There wasn’t any step by step, one thing, it was just taking it all in.
Eric
Yeah. And you had previous experience as a kid. I understand playing some other instruments. Can you talk about that? Yeah.
Derek Sivers
That might have helped a bit. You could say that. Maybe that was another circumstance that my parents helped create is my mom forced me to take music lessons ever since I was 5 or 6. She said, “I don’t care what instrument, but you have to play something.” And so I played piano for a few years and then switched to viola for a year and then clarinet for about five years. So I actually kept playing clarinet in the high school band. So even as as guitar was my main instrument, I would grab the clarinet for an hour a day for jazz band at school. And I was proficient. I could play.
Eric
Yeah, there’s something about learning multiple instruments as well. There’s a guitarist I love named John Jorgenson. I don’t know if you’re familiar with him, and when I saw him play one of the first times he was playing in a quintet, doing Django Reinhardt style gypsy jazz music, but original compositions, some Django covers, but just absolutely mind blowing guitar in that style. And then about halfway through the show, he picks up a clarinet and he was like, equally good on the clarinet.
Derek Sivers
Wow. Cool.
Eric
And that was a shock. So it’s interesting how you look for different perspectives now in your life in general and different ways of looking at things in the world, and that might be a different, you know, even just within the confines of a single pursuit like music, experimenting with different instruments can give you different perspectives on how sounds are created, how music is created. It’s a physically different process, so it may stimulate different parts of your brain and your nervous system and who knows what else.
Derek Sivers
Yeah. Which could apply to anything you’re doing. Even if you’re a computer programmer and you have your layout perfectly set up using Microsoft Visual Studio on Windows and Python is your programming language. Well then you know, try installing the OpenBSD operating system and learn the language called Rust or SQL or something like just to expand your perspective. Instead of just doing one thing, you can pick up something else, even if it just becomes your minor. Like the way that I played clarinet one hour a day. It can definitely broaden your horizons and help you see things from another point of view.
Eric
Yeah, in one hour a day, I might add, is not insignificant, you know. So as you were delving into this obsession with music and were there any other-- what you would consider pivotal influences, artists, guitar players or otherwise that you took serious inspiration from in pursuing your own craft? And this can be, like I said, either with musicianship on, for instance, with guitar or I know you got obsessed with songwriting and the craft of songwriting. Did you have any like big time heroes in either or both of those veins?
Derek Sivers
Brian Eno has wonderful philosophies about music. I like his music, but I love his thoughts about music. So if you find any Brian Eno interviews he has some wonderfully open minded philosophies about music, some thoughts about making music. He created a deck of cards called “The Oblique Strategies” that are a bunch of directives meant to be shuffled and pulled out at random. So if you’re sitting there working on a song and you’re not sure where to take it next, you shuffle the deck. You pull out the card and it says something like, “Cut a crucial connection.” And you think, “Okay, well, it’s a hip hop song. The beat is everything. I’m going to cut out the drums, see what happens.” You know, it just helps you add some randomness into the creative process. And through Brian Eno, I learned metaphorical things like he found out that perfume companies invent the name and the bottle first. They choose a name in the bottle and they do some test marketing to find out what name and bottle will sell well in the market. And then they add the scent last. And I thought of that metaphorically with music. Like, how could that be? Do we need a song title first? Do you need a band photo first before you decide what kind of music to play? Things like that, I think, opened my mind a lot.
Derek Sivers
And then using musicians histories metaphorically. The way that Bob Dylan was all about the acoustic folk until he showed up at the Newport Folk Festival with an electric band and pissed off everybody. But that was necessary for his personal growth. Same thing with Miles Davis leaving bebop behind and even, you know, people like Paul Simon, David Bowie, that changed their public persona often and changed their musical style in the name of growth. They could have just stayed with what everybody knew them for, like ACDC, but pushing them selves to take on new styles. I think Paul Simon did it the most deliberately the way he was like, “All right, I’m going to make a South African album now. I’m going to make a gospel album now.” That can be a great personal growth challenge, even if it means you’re going to lose some audience. It’s taking care of the goose that lays the golden egg instead of just spitting out more eggs.
Eric
Right. So it sounds like that was something that you were after even back then as a teenager that you were interested in sort of growth and expansion and not just like repeating yourself, but constantly pushing yourself and learning new things and growing as a as a musician. And so I know that you went to Berklee College of Music in Boston, and I would love to hear about how you chose to go there. What was involved in getting accepted and then what what your experience there was like. Did it satisfy what you know? Did it give you what you were looking for?
Derek Sivers
Oh, Eric, I love how much research you did. I don’t know if I should say flattering or honoring that, it’s amazing what you’ve researched. I’ve done many interviews where I get on the interview and they say, “Okay, Derek Sivers, Sivers is it Silvers? So what was this company you started?” I’m like, “Oh, really? Okay, sure. We’re recording. I’ll tell you my whole history and how to say my name.” So I’m really honored that you researched a lot. Thank you. So, Berklee College of Music. I don’t think I’ve ever publicly told the story of how I decided to go there. But you specifically asked this. So the bassist in my band and I, at the age of 16 or 17, were drunk at a party at a friend’s house. Ian Narcissi and the Chicago Tribune had just published an article about Berklee College of Music and talked about the music echoing through the halls. He and I had both seen that article in the Chicago Tribune and both separately kind of went, “Wow, that sounds cool.” So we were at this party, Ian Narcissi’s house drunk, and he’s just like, “Dude, we should go to Berklee.” I was like, “Yeah, let’s go to Berklee, man.” He’s like, “Fuck it, Let’s go. And just me and you will go at the same time. Yeah, let’s go.” So we did. We. kike the next week told our parents and we want to apply to Berklee College of Music and our parents said okay. And yeah. Mark Striegel and I both attended Berklee and now Mark Striegel is the host of the very popular podcast called Talking Metal. And I think he’s even on it as it’s serious. Is that the satellite radio? Is it.
Eric
Sirius XM, Sirius XM, all the mergers.
Derek Sivers
All right. So he also hosts a radio show on Sirius XM. That was my friend Mark Striegel, who I can bust his identity too. I later produced an album by him. He called himself Captain T, and there’s a chapter in my book called Your Music and People about Captain T, That’s my friend Mark Striegel from Hinsdale, Illinois, with whom I got drunk. And he suggested we go to Berklee College of Music. So Mark Striegel is the reason I went to Berklee College of Music. We went to Berklee College of Music. So then you asked about getting in. That was just easy, I think at least at the time, anybody could get in.
Eric
Audition, no, anything?
Derek Sivers
Barely. My roommate my first year was just terrible that didn’t know a damn thing on guitar and he got in somehow. So I think maybe they want to give the impression that it’s hard to get in, but. Or maybe it is now. I don’t know.
Eric
I didn’t get in myself. I had applied.
Derek Sivers
Are you serious?
Eric
I’m serious. I remember. So I had started college at Penn State. Which was-- I didn’t put much thought into that decision. It was a state school. My parents basically said, We’ll pay for anything that’s a state school if you want to go anywhere beyond that, you know, that’s all we can afford. So then you have to figure out how to how to finance it.” So I thought, well, Penn State meant I live away from home. That was about as much thought as I went into it. But immediately when I got there, I loved living away from home. I did really well in my classes, but I was like, “Yeah, this is so not the environment for me.” And Berklee College of Music was, I remember the catalog. It was like Disneyland for people like me. It was like you can major in songwriting. Like, “Oh, like you’re kidding me.” And so I applied. And I remember from my second semester at Penn State, all the courses I took were just because they would easily transfer over because I was like, “This is what I’m doing.” And I didn’t get in. It was all based on your application. There was no demo tape, there was no audition. And the reason they gave was that for my rejection was lack of formal music training.
Derek Sivers
Wow.
Eric
Yeah. And I thought, “Well, that’s why I want to go there.” I had AP music classes in high school, so I did have a good background in theory. And so initially I was crushed. And then I realized that, you know what? All of my heroes, if they bothered to go to college at all. They dropped out. Yeah, and you know what I mean? So I took some consolation in that and anyway, but yeah.
Derek Sivers
What year was that?
Eric
I was a freshman in college, 1990 to 91. So it would have been it would have been in that time right after you graduated. Right.
Derek Sivers
I graduated in 1990. Yeah. Yeah. Wow. Well you didn’t miss much. Berkeley did not have great teachers. It had some great musicians. That also got a gig teaching that would show up but weren’t necessarily great teachers. I was really disappointed in the level of teaching I found there. So much so that after my first year, I almost dropped out until I looked at what the alternatives were. I looked at going to Northwestern University for music and they didn’t teach jazz or pop. It was just all classical. I was like, “Oh, I don’t want to study classical music.” So I went back reluctantly, and instead I just decided to treat it like a library. Like, okay, here within these halls there is a bunch of wisdom. I’m just going to have to go get it myself because nobody’s giving it to me. You know, nobody can teach you anything. You have to have to get it yourself, ultimately. So that’s what I did. I made the best of it and it was all right. I spent a lot of time in what they call the Career Resource Center, where they had stacks of books about the music business and audio courses or recordings from conferences where people were at up on those podiums being interviewed, talking about how to make it in the music business. And I would sit there during my lunch, every single lunch hour. I was like the only kid in there.
Derek Sivers
I would just go to this sad, quiet little room that nobody ever went to. And I’d put on the headphones and listen to these recordings of record company presidents talking about how to get in the music business while I was eating my lunch for an hour and then I’d go back to classes and practicing. Also, one of my favorite things I did is that they closed the piano rooms at midnight and you could have them for a maximum of two hours. So every single night, without fail, I never missed a single night every night at 10 p.m. or more like 9:55 p.m., I would get a large Diet Coke, a little box of Junior Mints, and I would go into the piano room at 10 p.m. and I would practice for two solid hours in the piano room from 10 to 12, working on my singing, working on my piano, playing, because the other hours, of course, I could practice guitar in my room any time, but to play on a real piano, I needed that piano room. So yeah, never missed a night. I loved that seven days a week. So it was a good environment, but I highly discourage people from going. Now, when I get emails saying, “Hey, I’m thinking of applying to Berklee College of Music, I know you went there. What do you think?” I say, “No, no, no, no, no, no, Do not go.” The thing is, like you, I was there in the 80s.
Derek Sivers
There was no internet. And now with the internet, the best teachers in the world are not in Boston at Berklee College of Music, the best teachers in the world are in front of a camera in Romania or Louisiana or Mexico. And they’re teaching you everything you need to know on YouTube for free or sometimes for a $50 or $99 course. But there is no need to spend $35,000 per semester or whatever it costs now to go to Boston to do that. I tend to think that the people that are at Berklee College of Music now are those that are not resourceful. I think if you have any resourcefulness at all. You can find a much better way to learn better and faster and even put yourself in a new environment. Even if you want to be around other musicians, then you move straight to New York City or London or Los Angeles where everything’s happening and put yourself into the real scene instead of this kind of tiny little bubble of a scene or just even exactly where you are right now. There’s a way to reach out and find other musicians, and that’s how to be resourceful. And therefore, those that are paying $35,000 a year to sit at Berklee, I think by definition are not resourceful. And I would not recommend going.
Eric
Well, that is fascinating. And it begs the question about college in general. How how useful, important? Obviously, there are certain professions where you have to right, like if you’re going to be a doctor. Well, you have to go to med school. You can’t just like learn off the internet. But I don’t know, what are your views? You know, your son is what, 11 now? So he’s a ways off. But you know, he’ll be of age at some point in the not too distant future and I don’t know what are your thoughts about, how essential is college, how do you feel about the importance of it and the is it a worthwhile investment? I think that given the costs of college now. It’s a legitimate question. Not that the sole purpose of college is to get a high paying job. Right. But I mean, ideally, it’s a place to explore and learn and grow. Yeah. But, you know, we’re in a reality now where the cost of it is such that the stakes are so high that there is a legitimate expectation of some kind of ROI for this investment, especially if you’re going to end up in serious debt. Right. So what do you think?
Derek Sivers
Well, for one, there are places where you can go to college without serious debt. So colleges in Germany are free. Colleges in other parts of the world can be much cheaper than they are in America. I mean, basically everywhere is cheaper than the American universities. So I think it’s very worth expanding your horizons to look worldwide. If you do think you want to go to college or if your parents insist you need to go to college. But it is an environment, isn’t it, like I think about I was there in Boston. Which is an inspiring city because Boston has this message. That you should be smarter. So sorry. Let me explain this there. Paul Graham, who founded the VC company called Y Combinator. He wrote an article years before that saying that cities have a whispered message. And he said the whispered message of Boston is you should be smarter, that the city of Boston, the culture of Boston seems to value intelligence. So he says, like just being there, there’s a kind of whispered message, maybe not even spoken, but you feel it, that it’s like you should read those books on your shelf. In fact, you should go down to the library and read other books. You should expand your mind. Whereas he said the whispered message of New York City is you should make more money. That he felt. By the way, I don’t necessarily agree with all of his takes on it, but they’re a good start.
Derek Sivers
He said the message of London is you should be more cosmopolitan and the message of San Francisco or sorry, the message of Silicon Valley is you should have more impact. He said it’s not necessarily about the money. It’s about having an impact on the world. And you live in LA now?
Eric
Yes.
Derek Sivers
Okay. So, yeah, i lived in LA for years and I loved it. And his take on LA was he said the whispered message is you should know more people. You should be more connected. That it’s a city of freelancers and you’re as good as your next gig. And we get our gigs from the people we know. And that agreed with my experience being there for six years. And so the place you are can really affect your outlook on life. Yeah. Did I live in all the places I just mentioned? I guess I did, didn’t I? Yeah. I lived in all those places and I did feel affected. Oh, that’s right. I disagree with the New York City and the money one. Maybe it’s just the circles I was in. It wasn’t all about the money in the circles I was in New York City. It was about, maybe it was about making a name for yourself. Maybe it was about like making something happen, getting something started. Yeah, that could have just been the time and the age I was there and the circles.
Derek Sivers
But definitely San Francisco. I thought I was going to love, but I ended up hating it because everybody just wanted to talk about their investments and investors and their angel investors and their series A round something and their Q3 results. I was like, “Oh, it’s all about investors here. Yuck. I have no interest in this.” But I really love the Los Angeles spirit. Where again in my circles, everybody was doing something creative and so creative expression, storytelling. Creativity was the most valued thing. So it was who, you know. But then what are you making? And I felt that even the level of conversations people were having were creative conversations. It was people like asking questions and digging into things and questioning the creative process or optimizing their lives around. The creative environment that they were in. And I found that so refreshing and easier to relate to than, say, when I moved to Singapore. And creativity is just looked at with a furrowed brow like, “What do you mean, creativity? How does that make money?” Because they’re coming from a different mindset. Yet creativity is not a fountain of profitability in Singapore. The profits in Singapore, where people are culturally and financially rewarded in Singapore are for following instructions and getting a good paying job at the multinational corporation. So creativity is not rewarded there. But an advantage of being in Singapore was suddenly meeting some of the best and brightest from China and from Indonesia and from India because it’s like a melting pot in the middle of three massively populated countries.
Derek Sivers
So that expanded my circle of kindreds. It was kind of amazing to be sitting there feeling very kindred with somebody that grew up in Bangalore or grew up in Jakarta, and I’m feeling like we have everything in common, even though we don’t by other measures. So that was really good for me. But wow. Sorry, we were talking about college and environments that I think that going to college you get to choose an environment where being smart is rewarded and that’s where it matters which college you choose. Because there are some colleges where the main thing that’s rewarded is sports, and maybe you choose it for that purpose, if that’s your thing. Right. And there are other colleges where I’ll bet there’s a lot of focus on getting a good job, you know, like especially like Insead, MBA schools where you’re there to get a good job as a consultant afterwards. And that’s the main focus. Whereas there are other universities or colleges that are focused on you expanding your mind and trying something new. And hey, you should try reading this poetry and let’s dig into the the anthropology of the rainforest or whatever, you know, things that have no goal of profitability but are good for expanding your mind. So I think it is it’s choosing an environment like choosing a city.
Eric
I think this is such a rich topic. I agree that places have often an unspoken value system that you absorb, whether you’re conscious of it or not. And I also agree that it makes a lot of sense to be intentional about putting yourself in an environment because you’re looking to grow in a particular way. So for instance, when I was done with college, I lived in Nashville, which was just so stimulating musically. Everybody in Nashville, at least when I was there, was a musician. I mean, everybody. So whatever day jobs I had, I met other musicians and it was people of all levels and abilities and even all genres. And, you know, styles of music could be heard in Nashville on any given night between the local musical population and and acts passing through. So it was highly, highly growth for me to be in just immersed in music when I lived there. And I think that also, of course it’s a generalization to say that everybody in New York is all about ambition or whatever it is. While there can be a kernel of truth to it. You mentioned your circles when you talked about LA. At least in my circles, the focus was on creativity. So there’s a couple messages, I think, in what you shared, which is, you know, wherever you happen to be, do what you can to create a circle that is simpatico with you. And if you live in a big city like I do, there are lots of experiences you can have of this city depending on kind of where you place yourself and who you hang out with. And if you can’t find what you’re looking for, maybe it is a good idea if you are able to deliberately put yourself in a completely different environment. But yeah.
Derek Sivers
Yeah, which may be signing up for a course. Or something like a songwriters circle or something like that. Like intentionally putting yourself into an existing community that values what you want to value if you want to spend more time songwriting, yeah, go find a songwriters group or circle or something like that and join it. Because then right now you’ll be around 12 other people who also value this too. And yeah, intentionally putting yourself into these sub communities like that can help.
Eric
I also think there’s value in being in an environment that doesn’t feel right or at least there’s value you can extract. So, I was sort of reluctantly at Penn State, and every semester I would say, that’s it, I’m out of here. And I would have like a moment where I’m gone. I’m on the first Greyhound to San Francisco tomorrow, you know, and for each semester it was a different reason that I was like, all right, I’ll go back until I finished. Right? But you can glean a lot from being in an environments that aren’t your thing. You just learn about other people, other values and also it maybe helps you tune in to what you do care about by seeing how much you don’t care about what everyone else cares about. But this idea of intentionality, so I’ve heard it said that environment is stronger than discipline, I love that quote. And I think therefore be intentional. Put yourself in environments that encourage whatever it is you want to grow in yourself, whatever it is you want to learn about, whatever it is you want to explore or become. I agree with you that environment is everything. It sounds like Boston was a positive environment for you and you decided to make the most of it. Even if Berkeley, the school, disappointed you.
Derek Sivers
Yeah. And now I live in New Zealand, which is honestly almost exactly like what you saw in Lord of the Rings at the beginning when they go to the Little Hobbits Shire and they’re just a bunch of people out in the garden and you know, Gandalf pulls into town and they frown at him like, “What are you doing here? Troublemaker?” And he says like, “Let’s go on an adventure.” And the general consensus is, “Nope, nope, I’m just happy here. No adventure. Thank you. We just want to be here.” And that feels like New Zealand to me. It’s a really good place to raise a young kid. The freedom and the nature and the safety here is amazing. Just absolute. Just kind of wilderness that a kid can run safely in and just play and and grow up. Just feeling safe and connected with the physical world has been great. But a lot of what I’ve been saying about environment and the importance of it. I’m saying this now. From the outside and feeling a lack of it. I’m amazed how unconnected things are here. I’m amazed at how I haven’t found a culture of ambition here that I had in almost every other city I lived in. Every other city I lived in it was like a different kind of ambition. And here I often find none. So I go, “Oh, wow.” Okay, now I see living in this small, quiet place how important that environment in New York City or LA was for me.
Eric
And speaking of New York City, did you go right from--. Oh, actually, before we go there, I just want to briefly touch on this because I think it’s so fascinating the things that influence us. And sometimes they’re obvious and sometimes they’re almost these incidental things, like, I love the story you told about how you decided to go to Berkeley and how it was this confluence of things. This article appeared in the Chicago Tribune. You and your friend had separately seen it and kind of your interest piqued. Your curiosity was piqued by it. And then you’re both at this party and drunk and like, screw it, let’s do it, you know, and also the camaraderie of it and the having a partner in crime kind of to do it with like, you know what if that you hadn’t seen that article like, who knows, right? Yeah. So I do think it is so interesting looking back and of course we can only connect the dots in hindsight and realize how influential certain experiences or people or environments were. But I wanted to ask you because something that is somewhat unusual about your childhood is that you did move around a good bit. So I’d love to hear you talk about maybe quickly, just list or explain the places you lived in as a kid. And you know what what effect? Or significant things you realize now how that shaped you and who you became, if only in the sense that I know you. You have a bit of wanderlust in you as an adult and maybe that was programmed in from those early experiences. I don’t know.
Derek Sivers
Yeah. So I was born in California. I was two years old. Oh, Berkeley, California. When I was two years old, we moved to Chicago when I was three we moved back to California. When I was five we moved to Abingdon, England, outside of Oxford. And then when I was 6 or 7, we moved back to the Chicago area. Hinsdale Illinois. And and there I stayed. So it definitely taught me at an early age that life is movement. And I viscerally and vividly. That’s a word I vividly remember standing in our new house in Hinsdale, Illinois, at the age of 6 or 7. We had just moved there and I remember asking my mom, “So how long are we going to stay here?” And she said, “Oh, maybe five, maybe ten years.” And well, I was horrified. I cried. I sobbed that the idea that we would stay in one place for 5 or 10 years, that sounded like death, like life is movement. We move every year. What do you mean 5 or 10 years in one place? That was so sad. And I still feel that way. I don’t want to stay in any one place for 5 or 10 years. Ah, I love moving every year or two. I’d love to keep moving for my whole life, every year or two, to a new country, to a place I haven’t been. That’s life. And it’s funny that my younger sister, she’s only two years younger than me, but she has none of this because she doesn’t remember those early moves. She was a little too young, so she has always wanted stability. And yeah, I guess just the fact that I remember our early moves maybe shaped it or maybe it has nothing to do with it. Maybe it’s just in my DNA and I’m blaming the environment. Who knows?
Eric
I love this. Okay, so first of all, why did you move so much? What was the reason?
Derek Sivers
My dad is a particle physicist and he was just getting his what do you call it, postdoc, Something like that. Like after you get your PhD, you go work in some places.
Eric
Got it. And I was going to ask you, so it is so interesting, right, because you took to it for whatever reason, maybe it was your DNA, who knows what. But for whatever reason, as a young kid, you relished the idea of the new and a change and moving and being on the move and seeing different places and having different experiences. Whereas your sister for whatever reason did not have that experience of it, you know. And so I think that--. I mean, I’m of the feeling that we are born into this world with a definite personality, a definite like set of inclinations. But, you know, it’s impossible to parse out what’s nature, what’s nurture. Yeah, but it’s a question I find so fricking interesting. And I’m curious to know. And you’re a parent now and you have an 11 year old and I’m sure you’ve observed that. I know you’re a very hands on dad, and I’m sure that you observed that the personality that he emerged with and you’ve watched it watched him grow over all this time. So now, Guy Kawasaki, you were on his podcast and he asked you to what extent he asked you about the nature nurture question. And you said, “Well, I only have one kid. You have five”. You said, “So you’re better equipped to answer this, but I only have one. So I really don’t know how much is nature and how much is nurture.” But you must have some thoughts about this. No. Like. Go
Derek Sivers
Oh, you’re asking me? Sorry. What did Guy say to that? Do you remember?
Eric
Hmm.
Derek Sivers
No. Okay. So that’d be fun to read that transcript again. So I think we tend to blame nurture more. We tend to blame our environment. We tend to think that our kid is good because I’m a good parent, although I’ll bet you that if our kid was really bad, we’d say, you know, it’s not my fault. I’ve done everything I can. We tend to take credit for our successes, take credit for the wins and absolve ourselves of blame for the failures. So I don’t know. I think it’s fascinating to find out that in World War Two, there were twins, identical twins that were separated at birth and one adopted in America and one adopted in Austria, and that they found each other like 50 years later and found out they were exactly the same, like the exact same beard. They had both married a woman named Janet and got divorced and both remarried, a woman named Elizabeth, and they both smoked an obscure kind of pipe. And they both were way into model trains And like all these, weird, obscure facts that you’d say like, oh, well, I’m into model trains because when I was a kid, da da da, my dad showed me this. It’s like, nope, apparently that was just your DNA and you blaming it was like, because your dad had one. No, because guess what? Your identical twin in Austria didn’t have a dad that was into model trains. And yet he also got super into model trains like, no, believe it or not, that’s in your DNA. And who knows? God, isn’t that crazy to think that even your choice of spouse you think it’s because of your free will. But no, that was in your DNA.
Eric
So, I mean, do you see in your son, do you see aspects of yourself like I know that a lot of parents will say, “Oh, my kid gets this from his mom.” Or, you know, “My kid gets this from me.” Or “I have no idea where that comes from. It’s nothing like either of us.”
Derek Sivers
Well, my son and I are very, very close. In fact, it’s really sweet that even a week ago, one of my best friends said, “I think he’s your soul mate.” And I went, “Yeah.” And I told that to him. And he goes, “Yeah, we really are, aren’t we?” Like, we’re that close. We’re super, super, super close. So we spend just thousands and thousands of hours together. So that’s hard to tell where that line draws. Like so many of his outlooks on life are directly echoing mine. So I don’t know with him but yeah. What was the question? Sorry. You asked me about my kid. I started daydreaming.
Eric
Yeah, just. I’m asking you to answer the impossible question, but really just your perspective on nature versus nurture and observations that you’ve had, you know, that may have been influenced by being a parent or just being a human.
Derek Sivers
Well, then let’s talk again about environment that I’m so glad that after he was born, I was living in-- he was born in Singapore. So I was living in Singapore when he was born. And at first we actually made him a permanent resident of Singapore. So, you know, basically like the green card, the practically citizenship. And it just assumed he was going to grow up in Singapore and be Singaporean. And after about six months, we saw how other babies were growing up in Singapore, inside shopping malls and apartments. And we thought, oh, actually, no, wait, I want my kid to run out in nature and have the connection with the physical world. Feet in the mud. Hands in the river, you know. So moved to New Zealand for that purpose so that he could grow up in nature and I could be in an environment where I don’t know anybody and I could just give him my full attention undistracted by requests to hang out or speak at a conference or whatever. So putting myself here in New Zealand to raise him was a good environment for me, but specifically chose this environment for him. Actually, I’ll give a real concrete one since you’re asking in 2019 we moved to Oxford, England, because same deliberate choice, like, okay, he’s eight years old now for the next ten years, I want him to grow up in a smarter environment, New Zealand is not academic.
Derek Sivers
Intellectual growth is not very valued here. Play is valued. Hanging out is valued. Being in the natural world is valued, but not intellectual growth as much. So I wanted him to grow up in the environment of Oxford. And the truth is, he thrived. We were just a block away from one of the best schools and he got into the school and just loved it. And every day he was coming home telling me about some new thing he had learned. And like “Dad, did you know that Henry the eighth and this and that were the Tudors. Here, let me tell you about the Tudor dynasty.” And he was so excited to tell me what he was learning every day. But then Covid hit the school, shut down and we’re New Zealand citizens. And New Zealand was one of the only Covid free places in 2020 and 2021. So we moved back to New Zealand and we’ve been back here for three years and he hasn’t once told me anything he’s learned from school. And when I ask, I say, “So how is school? Did you learn?” And he’s like, “We played Tag, we played Kick the Ball. We played Chase. We built forts.” Like, “Did you learn anything?” Like, “Um, no.” So like, okay, now circumstance is dictating his environment. So I think by growing up here, he will be less intellectual and less intellectually driven than he would have if he had grown up in Oxford if Covid hadn’t happened. So we’ll see.
Eric
And always trade offs, right?
Derek Sivers
Yep. He’s happy.
Eric
That’s good. Happiness is good.
Derek Sivers
There are some miserable intellectuals, so yeah, we’ll see.
Eric
Wow. Okay. Berkeley. You graduate from Berkeley. Did you go directly to New York City? I know that you were intent on being a musician. You wanted to go where the action was. You were determined to be a professional musician. And I’ve heard you say, depending on the interview and the time and maybe your frame of mind that, you know, I’ve heard you say “I wanted to be a great musician. I wanted to be a successful musician.” And sometimes you said, “I wanted to be a famous musician.”
Derek Sivers
Those were all three. I think of those as all part of the same like it was-- I wanted to be like Prints or like Brian Eno. Or even like one of those songwriters that you’d read about that didn’t get super successful but wrote some damn good songs like John Prine, Tom Waits, you know. So. Yeah. Great. Famous, successful. Successful to me, my definition of success is achieving what you set out to do. So if you heard me say successful, don’t mix that one with thinking I wanted money. That was like, I’m setting out to be this, Stevie Wonder writing and recording and playing everything myself in the studio, being a great writer, being a great performer, to achieve that would be success for me. And of course, I would like public recognition because to me that was just like another part of the craft to master is the craft of marketing and getting yourself out into the world and being received as you want to be received. So yeah, those three are the same to me.
Eric
Okay. And you banged away at that for 15 years, roughly ages, as you said, ages 14 to 29, where that was your sole focus and sole obsession. So then basically what happened was, as the story goes, as the tale is told, the internet did not have a place for you to sell your CD on it. You had been selling CDs at gigs sold about 1500 copies, but wanted to expand that and make it available to people online. And there was nowhere for you to go. So you, being resourceful, figured out how to create a place online where people had a buy now button they could click on and pay you for your CD, which was like a big deal back then. Big deal. Not an easy thing. And apparently you weren’t intimidated. You decided to figure it out yourself. You didn’t know anything about computer programming, but you studied up and learned and taught yourself and figured out how to do it. And because you were such a rare example in that world and there weren’t other opportunities for musicians. Your friends asked you, “Hey, can you sell my CD on there too?” And before you knew it, you unwittingly started a ridiculously successful business. And I want to just, like, pause here for a second and just say that I was a CD baby musician, customer back in the day, like in the from the in the late 90s. I do not remember how I heard about it. I have no idea.
Derek Sivers
It was everywhere at the time. Word of mouth got around.
Eric
Yeah, it did. So I wanted to ask you a little bit about that. How did it go from your friends asking you to do it and you did it as a favor for them. You put their CDs up on your website and then more and more musician, friends of friends and more musicians kept asking, and eventually you realized, “I can’t. I have to charge for this.” Even though it wasn’t your intention to start a business, right? Yeah this is so interesting to me for. And there’s like a million questions I could ask you. So I’m going to try to contain myself and be focused here. First of all, at that point in time, did you feel like you had achieved your mission, your vision? Did you consider yourself a successful musician at that point?
Derek Sivers
Oh. Just barely enough. So, yes, like I said, I made probably a quarter million dollars playing at universities, enough leftover net profit that I was able to buy a house in Woodstock with the money I made doing gigs. I had released a record that did okay on college radio. So by my own definition, I was like, just if you squint, I could call myself a successful musician. It was just enough for me. So I felt okay with it. Like when CD Baby took over my life and I could tell that I wasn’t going to be making music anymore, I felt okay about that.
Eric
Yeah, I love how you talk about-- because we really do have our own standards, not only definitions of what success means, but we have our own standards for ourself. And so outwardly the world might view us as a success. But there are so many people where that’s the case, but they don’t view themselves as a success because they have a different whether it’s a higher standard or a different standard. Right, right. So I think it’s one of the life lessons there is out there to be learned, is to figure out what success means to you so that you don’t end up chasing some version of it that you don’t even care about. But if you can get clear about what it is that you want and what it means to be successful, then you know what to focus on. And then there’s another philosophy of yours that I love, which is just about looking at everything as an experiment, let’s see what happens. And if you have that viewpoint, then nothing can be a failure because all you’re doing is exploring and experimenting and seeing what happens.
Derek Sivers
Yeah, yeah.
Eric
So it’s interesting that you were just successful enough that you felt okay because you realized you were pivoting like all of your time and attention was being funneled into CD Baby, Right? Yeah.
Derek Sivers
And it came at a perfect timing because I had been touring nonstop for 11 years at that point. Like really non-stop touring for 11 years. And I was getting bored of it. And so when CD Baby started taking off, I went, “Oh, this is nice. This is this is much more intellectually stimulating.” I was in the van doing the same gigs, playing the same songs. Like, “All right, another gig.” And so when when CD Baby took off, I was like, “Oh, okay, wait, HTML okay, okay. Css Stylesheets. Okay. Javascript. Oh my god. Okay, database. How am I going to get that?” You know, like it was nice to feel my little neurons sparking with new challenges again.
Eric
And I remember. So, you know, you’ve been in my consciousness and my reality since the late 90s when I did become a CD baby customer. And it just occurred to me literally when I said it to you, because one thing we have in common is we both are avid journalers and I started journaling pretty regularly in the in early 1998 is when I started doing it pretty seriously and regularly. And there were some gaps, but I bet somewhere in my journal maybe I can actually find out exactly how I found out about CD Baby. Wouldn’t that be interesting? Anyway--
Derek Sivers
Don’t do it for my sake. No, no, no, no.
Eric
Because I just really couldn’t, I just couldn’t remember. But my point is that as a customer of CD Baby, we would get these emails from you at all hours of day and night and your enthusiasm is what I remember most. It was so clear that you were obsessed over what you were doing, but that you were, like, excited about it. And you were right. You were doing things at all hours of the day and night, and these emails would come in and you were like doing everything you could think of, and you were just like, it was so clear. I was really impressed just by this spirit in the world. Like, who is this guy that he’s like doing all this crazy stuff and like also that you just had this, it was a very non businesslike approach to business, which was extremely refreshing. And you really were all about like trying to do whatever you could to help the musicians that were your customers. And yeah it really felt genuine.
Derek Sivers
I saw it not as a business, but as a public service. I was doing a public service for musicians. That I charged just enough so it could continue. So it was self sustainable. So I was not aiming to make a big profit. I was aiming to just make this service self sustainable so it could keep going.
Eric
Yeah. Anyway, it was a massive success. And one of the things that I also think is very interesting is that in my journal over the years, I know that especially when I was soul searching and trying to figure out a direction for myself, I would ask certain questions. And among those questions I would ask, “What is it that I really, really want?” But I would also say, “What is it that life wants from me? What is it?” Because I’m going after the things that I want or that I think that feel right to me. And, you know, just like running into a wall, running into a wall, running into a wall and going, “So what is it that life wants for me then?” If it’s not the things that I’m on fire about or I’m really like passionate about and that’s been a really difficult thing, honestly, for me to navigate is because sometimes you get a message, life taps you on the shoulder or whacks you on the side of the head. And in your case, like life said here, this way with like the response that you were getting from CD Baby, I’m not going to go deep into the story of CD Baby, because that’s all in your book, Anything You Want. And I really recommend everybody go out and read that because it’s absolutely fascinating just your thoughts and philosophies about business and how because you were so non wanting to start a business, you ended up doing all these things that were genius and helped helped CD Baby blow up and become successful because you weren’t trying.
Eric
You didn’t want it. You were turning down. You were like, I don’t want it to grow bigger. When you get these like, calls from people, I want it to be smaller. Yeah. And it’s such an interesting example of sort of liek and counterintuitive how your attitudes and philosophies can impact your results in life. But CD Baby came to an end and it has a story I mean, you know on the surface it’s this massive success story. But there’s a poignancy to it because there’s also a real sadness to the end of the story when this thing this baby of yours, literally that you had created kind of like took on a life of its own and your employees kind of almost kicked you out and it was just like you went away and you never came back. And it was just like, you want to cry. Like, it’s so sad. Yeah. What do you remember emotionally about the end of that time for yourself? And, you know, it had been your sole focus for so long. So I’m curious just to hear about what that was like for you emotionally.
Derek Sivers
I still consider July 10th, 2007, to be the worst day of my life ever. That was the day that I was traveling. And so I heard a recording of a company meeting. We used to have a company meeting every Monday, just a quick kind of all hands on deck. And you know what needs to be discussed. All right, we’re good. And we would record those meetings for the purpose of those who couldn’t be there that day. And July 10th, 2007, I was the one who wasn’t there that day. And so the meeting was people that I considered my best friends and people that I was paying out of my own pocket and people that I had had sleepover at my house. Hearing all of them railing against me as like an angry mob saying, “We need to get rid of Derek so we can run this company the way we want. And yeah, fuck him.” And I just heard all this because remember, it’s not like this was a company with investors and shareholders. It was just me. It was 100% mine. And every person I was paying, I was paying out of my bank account. And for them to say we need to get rid of him to run the company the way we want.
Derek Sivers
I mean, part of me was just like the audacity, like, come on, this is my thing. I hired you to help me with my thing. But devastated at this feeling of betrayal. You know, actually, I’ll bet most of us have had this at some point in our life. Even if it was when you were 11, you’ve heard that somebody you considered to be your best friend, like talked about you behind your back and you were just like the betrayal, this feeling of like, “I was emotionally vulnerable with you. I was emotionally leaning on you. I thought we were friends. Oh, my God, you just stabbed me in the back.” And so to hear that all at once happen with like 20 people that I considered as friends, all railing against me was devastating. It was so heartbreaking. And that’s why I never went back. Yeah, I didn’t sell the company until, I guess 13 months later, but I never again went back to the office. I never again saw any of those people or talked to them ever again. Like, I can’t. It was devastating. So no, to me, my ten years of running CD Baby ended in complete failure. I sold the company because it had gone so badly.
Derek Sivers
I had to sell. I had to walk away. The other option was to either I slightly considered firing everyone and then moving the company to a new location, Texas, who knows what, and then hiring a whole new crew and getting back to work with new people. Because I still loved the clients, I loved the musicians. I loved the customers. I loved the mission. I just felt like the culture there in Portland, Oregon, of those 80 people had gotten corrupt, but it could have been rescued. I considered remaining the owner and just hiring somebody else to be the the CEO and I would just be the owner. I considered just shutting it all down and walking away. And then somebody pointed out like, you know, “You could if you’re thinking of shutting it down anyway. Well, you could walk away and take some money that could make you all set for life.” I was like, “Oh yeah, I forgot. This is worth something.” I forgot about the whole money aspect. I never think about the money. Oh, yeah, that’s the option I chose, which I’m thankful for. I’m very, very thankful that I took the money and walked away.
Eric
Yeah. So you took the money and you also made a big decision, an unusual decision with the money. And you started a charitable trust. Can you explain?
Derek Sivers
Yep. And I’ll just do it super succinctly. Again, it’s been explained at length, but just in short, there was just this moment where we had this agreed upon price of $22 million and there was still like another eight months of paperwork to do due diligence and all this stuff. And my lawyer who luckily had a background in tax law said, “All right, so $22 million, what are you going to do with the money?” I said, “Oh, I’m just going to give it all away. I don’t want it.” I said, “I mean, I’ll keep $1 million to pay my rent or whatever and just invest it, but I’m just going to give it all away.” And he said, “Are you serious?” I said, “Yeah.” He said, “Are you dead serious? Are you completely, irreversibly serious? You’re seriously going to give it all away?” I said, “Yeah.” And he asked me why, and I explained. And he said, “Because if you’re seriously going to give it away, there’s something we can do in US tax law where instead of you receiving $22 million and then paying $7 million in tax and therefore giving away $15 million, you can give away the entire $22 million if you structure it in such a way.” And I said, “Oh yes, please tell.” So he said, “Yes, set up a charitable trust. Now transfer the ownership of CD Baby into a charitable trust. Therefore, when on Disc Makers buys it, they won’t be buying it from you. They’ll be buying it from a charitable trust. And the entire $22 million can go to charity.”
Derek Sivers
I went, “That’s what I want. Yes, let’s do that.” So, I mean, it helps to know that CD Baby is already profitable. It was already earning like $4 million a year net profit at that time. So I had already paid off all my debts. I already had savings of a few million dollars. I just didn’t need the money. I’d have to be some weird narcissistic idiot to need $20 million, you know, for what, a giant boat, 20 Ferraris. Like, I just didn’t want it. I just didn’t want to be that idiot that spends $20 million. So instead, I was like, “No, other people need it more. Therefore, the logical thing to do is to give it to people that need it more.” And when I thought about it going to music education, that was like, “Ooh, full circle. That’s a nice shape. Circles are good.” The idea of it going back to music education, since all the money came from musicians and music fans and now it will go to benefit the next generation of musicians. I was like, “Yeah, I like that.” So it was a no brainer.
Eric
Interesting. And are there specific organizations that are going to receive it? How did you figure out who gets it whenyou’re gone and the money is bequeathed?
Derek Sivers
Yeah, bequeathed. That sounds almost like a swear word.
Eric
Doesn’t it? Maybe it is.
Derek Sivers
So, yeah. Good point. So bequeathed. That’s okay. I just went and found three very effective music charities that are doing good and whatever, and I had some three of them like named in my will, basically the trust document. And I update it now and then. So if one of them goes out of business, I’ll replace another one. So yeah, that’s all nice.
Eric
Now after that you wrote in your book “I continued learning until--” I mentioned this quote here before. And I’m going to continue reading from that spot, “I continued learning until I felt like an absolute idiot. I was paralyzed, unable to create anything new. I’d start to make new things, but then see how stupid they revealed me to be. So I’d stop. I lost all confidence. I spent a few years completely stuck.” Now, this sounds like like the opposite of how you appear in the world where you’re always full of energy and doing interesting things, but naturally of course, like after an experience like this, it makes sense to me, but I would love to hear more about this period of time, whatever you want to share about it and how you managed to get yourself back on track and to figuring out what was next, if you will. If I can use the title of the show, who the person you wanted to be next would be coming out of such confusion and maybe, you know, emotional devastation.
Derek Sivers
It’s funny hearing that quote. Was that in my book or is that in a in an article somewhere? Wow. Yeah.
Eric
It was a chapter called “You Don’t Need Confidence, Just contribution”.
Derek Sivers
Okay. Because I don’t think it was actually a few years that I felt stuck. It was probably about a year. Yeah, I felt a little lost and that’s okay. I think if you’re listening to this and it sounds like something you can relate to. It’s okay to be lost and searching for a while. It’s okay to finish one thing before you know what the next thing is. I mean, it’s ideal if you can keep momentum. I think if Tarzan swinging on the vines through the jungle, there are two lessons you can learn from Tarzan swinging on the vines in the jungle. One is you don’t let go of the previous vine until the next one is supporting your weight. So this idea like if you’re leaving one job or leaving one industry and getting into another, then you wait till your hand is grabbing the next vine and it supports your weight and that’s when you let go of the previous one. So get the new thing happening first before you quit the old job. But also what you learn from Tarzan swinging on the vines in the jungle is momentum that he’s able to swing on the vines because I assume he starts from a high tree and leaps at the first vine. And then the swinging of the vine helps him catch the next one. But if he ever were to just like stop, the vine would go and suddenly he’d just be hanging still on a vine with no momentum. Well, then there’s nothing to do but drop down to the ground. So momentum can be crucial, to not lose momentum if you’re laying out the ultimate career strategy, then don’t lose the momentum. But if you have lost momentum. It’s still okay. You can still, like, drop down to the jungle floor and walk and climb up another tree.
Derek Sivers
It’s not optimal, but it’s doable. So I think that’s what I really did in 2008 when I sold CD Baby. I spent about a year just reading books and just feeling a little lost. Like what now? I thought my gravestone would say, “He made CD Baby 50 years ago and really not much sense, here he lies.” Um, So I spent about a year feeling lost. Until one day I just bolted up in my chair full of inspiration that I wanted to be a TEDx speaker. I wanted to be a writer, speaker, thinker, kind of guy, like the kind that the TEDx conference invites and that mission filled me with intention and action. It made me instantly full of adrenaline. Lay out an action plan for how I would do such a thing. How I would become a writer, speaker, thinker, guide at the Ted conference would invite to speak. And just seeing how much adrenaline and action it filled me with, I felt, okay, this is the right thing for me to do now. That was the indicator that I was on the right path because a good goal is one that makes you take action. Goals don’t shape the future. Goals can only shape the present moment. A good goal is one that makes you take good actions in the present moment. And if it doesn’t do that, then it’s not a good goal, no matter how. Quote unquote inspiring it may be if it’s not making you leap into action in the present moment, it’s not a good goal. So this one did, this goal helped me take action. So then I was officially out of my funk and on to the next thing.
Eric
Beautiful. And I can imagine someone listening to this and hearing that and going, maybe they’re in that phase of stuckness and feeling lost and just having no clue and no motivation or desire or obvious point of direction, you know, how can I get that moment that Derek’s talking about, that epiphany where suddenly you are inspired? I would love to hear what you have to say about that.
Derek Sivers
It can come from anywhere. Inputs, inputs take in good quality inputs, whether it’s from books or YouTube or podcasts or whatever it may be good quality inputs. For me, it’s reading. I love reading non-fiction, educational books and that specific one. It was in a history book. In fact, I think it might have been Robert Greene’s “48 Laws of Power”. Maybe even “Art of Seduction”, where he goes into historical examples of uses of power. And I believe it was when he was talking about Benjamin Disraeli, who I think is an old prime minister of England, but started from nothing, didn’t come from a noble family. And it said how he made a name for himself by always stepping into the spotlight and always courting attention. And at the time I was feeling like the opposite. I was feeling like I had too much responsibility and too much attention with CD Baby, I want to lay low. I want to legally change my name. I think I’ll just be an open source programmer. I’ll move to Europe, change my name to Wendell. Nobody will know who I am. I’ll be anonymous. I’ll just get into open source programming and live off my savings. That was my plan that wasn’t super inspiring and making me take action. It was just like, “Yeah, I guess that’s what I should do.” And then I read this one thing where just a quick mention of Benjamin Disraeli, and I went, “Oh, oh. Or I could lean into the spotlight.” I was like, “Yeah, it means catching a little more slack.” I mean, what do you call it? Like, you know, it means putting yourself in the rifle point. What am I talking about, what do you call it? Put yourself in the sights of people’s attacks.
Eric
Oh yeah. Making yourself a little vulnerable. Yeah.
Derek Sivers
Making myself a target. Yeah. I’d be making myself more of a target for ridicule and attack. But on the upside. When you make yourself a public figure, you meet a lot of interesting people. And I like meeting interesting people. I like having interesting conversations with smart people. So, yeah, I think I’m actually going to lean into this and aim to be a little more public or a lot more public than I’ve been. So that was a deliberate decision in 2009, and that’s why I started applying to speak at the TEDx conference. And then they said yes. And then I spoke at their three in a row in one year in 2009 and ten, and courted a lot of attention and it was good. And then here I am on a podcast like this where you’re asking me all kinds of questions. And, you know, the reason I do these is because of the people that I meet that hear them. So I’m not doing this to sell books. I’m doing this because you who’s listening, whoever you are, wherever you are, ideally, we’ll go email me afterwards and then I get to meet these really cool, interesting people because I’m here doing a podcast. So that was a very deliberate decision. While reading the 48 Laws of Power and reading one sentence about Benjamin Disraeli and going, “Oh my God, yes, this is what I need to do.”
Eric
Wow. Thank you so much for that answer. I loved it. I love the idea of giving yourself interesting inputs and you never know where inspiration is going to come from. And I would add to that, you don’t even know when because at least in my experience and observation, sometimes I’ll read a book, let’s say, that really inspires me. And I have a specific example of this. In summer of 2001, I read this book called “A Walk in the Woods” by Bill Bryson. He’s American. He lived abroad and he comes back to America and he wants to rediscover his home country through tackling this crazy adventure of hiking the Appalachian Trail. 2168 miles goes from Georgia all the way up to Maine. And he tells it. It’s a brilliant book. It’s part memoir, part armchair natural history, naturalist, environmental. And it’s just all these different things that he weaves into it. And I think you read that book and you probably it’s very entertaining and you’ll have probably one of two reactions. You’ll either go, “I would never in a million years do something like that.” Or you go, “Oh, I’ve got to do that. That sounds so cool.”
Eric
I had the latter response, but nice. I was busy doing other things, so it was in the back, but I stored it away in the back of my head and said, “If next year, come March.” Which is like sort of the season for doing this, if you want to, if you want to try to attempt to thru hike the trail. If I don’t have anything better going on in my life and I’m perfectly willing to bring it on, I’d love to have other things going on, but if I don’t, I can always hike the Appalachian Trail. So in the early part of the year, I had this huge hopes for this relationship. This woman I had just met, I had huge hopes for this job I had interviewed for, and I thought, this is amazing. Like finally, right before I turn 30, I’m going to have all my shit together and have a great relationship and a great job. And it all blew up in my face. It didn’t happen. I didn’t get the job, the relationship. She wasn’t interested ultimately. And I was so bummed and I was like, “Now what do I do?” And it took a moment, but like. In the back of my head. Like, guess what? Look at the calendar.
Eric
You could, weeks from now be on the Appalachian Trail. And that’s what I did. So it was like, wow. It was input that I had taken in previously that came to the surface. So, you know, it’s not necessarily-- like you had it sounds like an inspiration when you encountered a particular sentence and it like had it set something off. But I think also because the timing was right. Yeah, yeah. But sometimes you just like, you know, things need to gestate and then the timing has to be right as you said but I love that. I love that story. And I know that when I heard you describe your experience of giving, maybe it was the first of those Ted talks. I don’t remember. You described yourself as incredibly nervous because your speech was coordinated to the video like and it had to be memorized and you had to execute it perfectly so that it would correspond with the video of the first follower. I think that was the first one you did of the Ted talks and you told the story of coming off the stage and all like, you know, adrenalized and Peter Gabriel saying, “Hey, great job, mate. That was fantastic.”
Derek Sivers
Yeah, more than that. I got to watch him interrupt a conversation. He was talking with three other people like, you know, 20 seconds away like this crowd there in the distance. He was talking to three people, and I saw him kind of look at me, do a double take, go like this to his friends, leave the conversation and beeline straight towards me. Do we call it beeline if it’s straight? Anyway, he went straight for me and just said, “Great talk, Fascinating. Just pithy and profound and funny.” And I was like, “Thank you, Mr. Gabriel.” Yeah by the way, it’s funny, speaking to a lot of my friends here in New Zealand are in their late 20s. They don’t know who Peter Gabriel is. They’ve never heard of him. It makes you realize he hasn’t had a hit in a long time anyway. Yeah, but you know what you mentioned with the Appalachian Trail I think is a great example of writing down your inspirations. I keep a folder called Possible Futures. So when you hear of something like that you think like, “Ooh, I want to do that someday.” Write it down and save it for yourself. Because exactly like you described, there might come a time later in your life, even if it’s a few months later, but it might even be ten years later. Were because you wrote something down earlier. You look at it again ten years later and you can go, “Oh yeah, now’s the time. This is what I need now, I’m going to do this hike or now I’m going to move to China and learn to get fluent in Mandarin or whatever it may be.” There’s a time when you have the inspiration and there’s a time when it’s the right time for you, and those can be different times.
Eric
Yeah. So this is a good natural segue into the subject of journaling. So I have been journaling, like I said, really pretty regularly since 1998. I know that you are a prolific journaler and I prefer pen to paper, but you make a pretty hard to argue with case for typing so that you can easily search for and find things which I have to physically go through notebooks to do that. But one thing that I find so fascinating about journaling and it’s a practice that I can’t speak highly enough about, I just think that it does so many great things for us. But one thing that I’ve observed when I have gone back and looked at journals from sometimes ten or even 20 years ago or whatever, and sometimes I’ll read a passage and be like, “You know what? I could have written that today. That’s exactly how I feel now.” I’m like, “What’s the deal? Like, have I not progressed at all? I’m dealing with the same issue. This is ridiculous.” And then of course, there are ways in which I’ve changed and grown tremendously and would be unrecognizable to that self from the past. So I want to ask you, being another avid journaler, first of all, how often, if at all, do you refer back to old journal entries and what have you noticed about your own? What have you learned about yourself in terms of I’m specifically wanting to know, have there been like issues that you cycle through or around and you find yourself like basically that have remained unchanged for years and years and years or decades even. What have you learned that has changed and hasn’t changed as a result of doing this practice of journaling?
Derek Sivers
All right. So listeners, if you don’t have a journal, start now. It’s okay if you didn’t start in 1998 like Eric. I actually wish I had started in 98. I didn’t. In fact, I think I did have some paper journals and then for years I kept a Microsoft Word document, one big document that I just kept adding to. And somewhere in leaving CD Baby, I lost it. So I lost many years of diaries. So I started after I left CD Baby, who knows, maybe it was on my work computer and then I just never went back. Who knows? So really, my current journals start in 2008, which for me was the age of 38. So yeah, anybody listening? I didn’t really start journaling really till I was 38. So start now. It’s better than ten years ago would have been best, but now is second best. So start now if you haven’t, I highly recommend. Okay. If you just love putting pen to paper then that’s that. That’s what you should do. But I really find text files to be the most useful thing because you can search them for particular words. You can search for the day you met Charlie or the first time you mentioned the word Chicago or you can search for how many times have I said the word depressed or whatever you can search for, word counts and things like that, which I find so useful.
Derek Sivers
Yeah. Even when I’m writing a new book on a subject, my next book is called “Useful Not True”. And I was able to search my diaries, for instance, of the word truth or true, and think about how many times it has come up when I’ve just been in my rambling diaries. By the way, when we say diary. It can be as simple as just saying in 5 or 10 minutes before you go to bed, just say what you did today and ideally how you felt. And even if you only have 5 minutes or 10 minutes, that’s all you need to say. Woke up, did this thing, got home, felt tired, made dinner, saw a friend, went to bed. That’s that. Believe it or not, even that’s useful to your future self. Because the thing that got me really, really into journaling in 2012 was wishing that I had a journal from my days at CD Baby going like I seem to remember being happy. Was I actually happy? I seem to remember just like working 7 a.m. to midnight every day. Did I actually or am I just remembering that? So I wish that I would have had even just the simplest little five minutes a day journal of what seems mundane today might be really interesting to you ten years from now or 20 years from now. So that’s like my main pitch to please start journaling now. And ideally, if you have more than 5 or 10 minutes, then you can just blather whatever else is on your mind.
Derek Sivers
You know, “Reading a book about something or heard this interesting podcast, something, blah blah blah blah blah, blah.” You know, “I wonder if I would want to move to Argentina someday or where would I want to move someday.” And just sharing your thoughts onto the page is therapeutic in the moment to sort out your thoughts for the day. Just get it out and then helps you sleep. And then it’s really useful to your future self to see what you were thinking way, way back in 2023. So, okay, that’s one pitch for why you should do it. I do go back and search all the time. I’ve found it really so directly useful in my life for this one main thing. Which is, when something’s in the far distance on the horizon, it’s hazy. We can’t see it as clearly as we would if we were standing with it in front of our face. It’s the same thing with time. Time at a distance is seen hazy. It’s very filtered. It’s foggy. It’s not as clear as when it’s right in front of you. Meaning something that was in Kevin Kelly’s book of advice is anytime somebody is asking you to do something a long time from now act as if they were asking if you can do it tomorrow. And if you don’t want to do it tomorrow, then you don’t want to do it in nine months.
Derek Sivers
But same thing with the past. We can remember the past fondly. We can remember the past with anger. But it’s really useful to see how you were actually feeling that day when that day was clear to you. So over and over and over again. I’ve gone back in my journal to past times in my life to see, like, how did I feel when I first met Alicia, my ex-girlfriend? What was my first impression when I met her? Was it as good as I think it was? Because I’m remembering that it was good. But then I look in my diary and it’s like every day I was like, uh, “I’m not really into this girl. She’s annoying. I think I need to break up.” You know? And I was saying this like one month into the relationship, and I found that so useful when when we hit this point. So, yeah, I did just break up with my ex in September, which is as we’re recording now, what is that, like eight months ago? Nine months ago. So. Reading my old journals is what helped me know that it was the right decision to break up because things were really hard day to day. But I remembered them as being easier before. It felt like there were only hard right now. And then I looked back at my past journals.
Derek Sivers
I was like, “No, it’s been hard the whole time.” I was remembering the past fondly because it was through the filter of time. But actually looking at my day to day journals like, no, it’s it’s really been hard the whole time. It’s really never been good. I think I need to break up and man, those are so useful. I’ve been so thankful for pulling the plug on that relationship. That was harmful. And it was thanks to my daily journals that I was able to get the clarity on what was the right thing to do. So, yeah, so many reasons to journal. Okay. So yes, I go back to them a lot. I searched them a lot for particular words. Like I said, I searched them for names. It’s actually come in handy when like I was even filling out a visa application form and they said, “Please enter the exact dates that you have entered and left the country in the last nine years.” I was like, “What? How would I know? Oh yeah, my journal.” So I just searched my journal for the word airport and flight. And sure enough, every time I was going somewhere, it’s like, okay, went to the airport, took the flight, you know, like, okay, now I’m able to find the exact dates in the last nine years that I’ve traveled. Okay, So now your next question was about traits or things that I’ve found kind of recurring.
Derek Sivers
For me, it’s one thing over and over and over again throughout history. I have found that I just want to work. I am repeatedly annoyed at requests from people wanting me to sit around and do nothing. To sit on couches and watch screens. To hang out. Drinking alcohol. Doing nothing. I’ve never wanted to do this. I have always wanted to just live a life of working. And again, this has come back to me after breaking up with a girlfriend nine months ago is, I am so happy to just be working again. I wake up at 6 a.m. and within 15 minutes I’ve started working and I tend to just work all day long except, I take a break to go take an exercise, walk in the woods, and if a friend calls out of the blue, I’ll stop to talk. But other than that, I work until like my eyes are getting droopy and I go take a shower and I go to sleep. And I love these days and I always have. I love working every hour. This is my ideal life. I don’t want a balanced life of hanging out and sitting around and doing nothing and watching screens. I just don’t do that. I just want to work. And this has been the case for the longest time and it really helped me to see that even in my oldest diaries, it was the same. I’ve always wanted to just work.
Eric
Beautiful. So one of the things I hear in your sharing is and I mean, you’re preaching to the choir about journaling, but it helps you. Helps keep you honest with yourself. It is so easy to delude ourselves, to fool ourselves, to tell us, to tell ourselves things that we think we should want or feel. And the journal, if you use it in an honest way, you know, that’s the thing about it is, it’s this container where you can be completely uncensored, completely honest. It’s just for your eyes. And so you can really see your truth. I love that about how that’s been such a consistent thread for you throughout your whole life that you just love to work, that you love to sit there all day and work on something. And there it is. The truth is there indisputably in your journal, if it’s not too personal a question, I wonder, is there a struggle that you’ve had that keeps showing up repeatedly in your journal?
Derek Sivers
It’s that one that I just said. Sorry if you were looking for something deeper emotionally. But no, it’s my ongoing struggle has been just wanting to work when I’m around people.
Eric
Oh.
Derek Sivers
Because people I care about and I do care about them. They want me to hang out. You know, my ex just wanted me to just sit with her on the couch for five hours a night. I didn’t want to. I cared about her, but I’m okay giving maybe 30 minutes a night, you know, one hour. That’s, like, all I’m really willing to hang out. That’s what I’ve got to give. And this has been an ongoing struggle is that some people feel bad for me, that all I want to do is work or they think I don’t have a rich life. But I feel bad for people who just want to sit on couches and watch shows and do nothing and drink wine, talking about the weather or gossip about their friends. That to me is kind of a sad life. I love that that I found what I love doing and I want to just fill my life doing it.
Eric
Yeah, that’s beautiful. And again, it’s whatever works. To use the subtitle of your forthcoming book, which I want to ask you about. So just a couple more questions, if you don’t mind. So this “Useful Not True” is your book that you’re currently working on, and the subtitle is “Whatever Works for You”. Yeah, the subtitle might change.
Derek Sivers
The subtitle might change. The title is definitely “Useful Not True”. Working subtitle is “Whatever Works for You”. But I’m still writing the book.
Eric
Yes. And can you briefly explain what Useful Not True means? And then I want to ask you a specific question about it.
Derek Sivers
Yeah, sure. Over and over again, I found that there are things that I’m choosing to believe because believing it is useful to me. And it can be useful for motivation. It can be useful for peace of mind. And there’s an example we’ve all heard, which is if somebody’s being a real jerk in traffic and and darting fast and speeding, you can think, “Oh, what a jerk.” But you can think, “Or maybe they’re rushing to the hospital because they’ve got a dying family member in the back seat.” And as soon as you think that thought your shoulders drop, your anger dissipates and you think, “Oh God, yeah, why am I so full of myself? People have tough lives out there.” And you feel yourself be more empathetic just thinking that thought. Now it’s probably not true. It’s probably just a jerk, but it’s useful for you to think that way. Another one we’ve all heard, if you’re on stage and nervous, it’s useful for you to picture the audience as naked or nervous as well. Hundreds of things like this, states of mind that are useful for you to adopt, even if they’re not objectively true. So I’ve been thinking this way for decades and constantly having to explain to people that say, “Yeah, but that’s not true.” I say, “I don’t care that it’s not true. It’s useful for me to believe this way.” And so I realized, wow, this is really an ongoing thread here, and I’m writing this book to explore it more.
Derek Sivers
The key idea. Is that once you start to realize how much nonsense comes out of our mouths, that even the things you tell yourself are often not true. You often don’t know why you do the things you do or why you’re thinking what you’re thinking. You don’t know the real reasons. And other people say things that are not true. Even if they say things like, “I hate you.” It may not be true. They might just be saying that in anger because they’re frustrated at something that happened to them on the drive today. You start to realize that. So few things that we hear people say, including ourselves, are actually true. I think it’s more useful to think of basically nothing is true except physical realities. You know, objects colliding as true. But all of the things that are the creations of our mind, let’s just assume that none of them are true and instead just think of whether believing these things would be useful to us or not. And if they’re not useful, then we can let it go. So that’s what the book is about, and I’m still exploring the different aspects of what this means. I thought that this book in fact, I even looked at our email history. I told you back in March that the book is almost done here we are talking in July, and the book is not almost done because I keep finding more angles to dive into on this. So still diving into it.
Eric
Yeah, it’s a great, great subject to explore and I’m sure that you’ll get backlash. But what I love about you is that as soon as you make an assertion or express an idea, you think about how the opposite may be true or like, you know. But I think that’s such a great habit to question your own thoughts and beliefs about things. I mean, I suppose if you did it like endlessly, it could be a problem. You’d never like make a decision or whatever. But I love the idea of questioning because we we get so we get righteous, right? We get like, so sure that we’re right about things. And what if the opposite is true? Or what if the opposite is also true? One thing that I just am so grateful to you for is these ideas that you’ve been putting out there all these years that are constantly making the case for are you sure? And is it possible to look at things another way? And why not question you know, your own sort of stuck grooves of the way you do things, maybe are there other options? And not only do you put these ideas out into the world in beautifully succinct and just incredibly digestible and provocative packages, but you’re out there being an example of this. You’re saying, “Yes, you can pick up and move to another country. You can get rid of all of your belongings.” Like you’re a living example. You’re not just like expressing these ideas theoretically, but you live them. And so I get I’ve gotten endless inspiration from that. So I want to just take this moment to say thank you because it’s such a valuable thing to be able to do, to question our own beliefs about what’s true or what’s true for us or what’s possible or not possible for us. So. Yeah. Thank you. Thanks.
Derek Sivers
And you know what’s funny? At the beginning of that, you said doing it only to a point because you might never do anything if you question everything. But actually, I do. I do think that even if you doubt everything, massive skepticism, doubt everything, you still can’t take action because you can say, “All right, well, what if none of it is true? Nothing is true. Then what would be the most useful one for me right now? Not for others, not for my past or my future, but for right now. What would be the most useful belief or thought pattern to adopt.” Given that probably-- you can.
Eric
You can take an action? Yeah, you can take an action on something even with the understanding like true or not, it doesn’t matter. This may be helpful. Oh, there’s so many interesting like ways in which I imagine you’re going to get a backlash from this or people are going to like what?
Derek Sivers
I’m just curious, what backlash are you predicting?
Eric
Well, like they’ll say, you know, what about science? Like, does that mean we should disregard scientific discoveries or scientific advice? You know, at what point?
Derek Sivers
So no, actually I named that one in the opening chapter. I say like, no, basically the scientifically observable things. That’s the stuff that is true. When I said like when I clap my hands and I said this physical reality, that’s like the observable things that a non-human whether that’s an octopus or an alien could observe this physically this physical reality. You know, like if you observe in a microscope, you can see vaccines working, that vaccines create a reaction which then will prevent future viruses from having a worse effect on your body. That’s just a true thing. You can count the number of votes in the election, right? And you can say, no, there were this many.
Eric
There are such things as facts.
Derek Sivers
Yeah. And so those are observable realities. Oh, but most of us, unless you’re a scientist, most of us live in this world where we hear statements, we make statements that are all debatable. They’re all like, if you can say something like, it’s important to be charitable. And you can say that like it’s a fact. But if somebody somewhere in another culture can say, actually it’s really damaging to be charitable, if anybody can make that argument, then I say this. This statement is no longer true. It’s no longer true like a scientifically inarguable statement to say it’s good to be charitable. That’s no longer true. If somebody somewhere can can argue. There’s an.
Eric
There’s an example where it’s not the case. It reminds me of Byron Katie’s The Work. Are you familiar with that?
Derek Sivers
Yeah. No, but I mean, what about it? So the work.
Eric
So The Work, so she asks these four questions and the first question is like, if you’re upset about something, right? The first question to ask yourself is, “Is this true?” This thought that you’re having, it’s making you so upset and then like, are you absolutely sure that it’s like absolutely true? There’s no room for it to not be true, you know, and then she just basically has you question your certitude to the point where you can flip it and play with it and realize that maybe other things are like kind of what you were like. You’re yeah, you know, is the opposite also true or is, you know, right. So all of that. But anyway, on this on this notion of Useful Not True. One of the first things I thought of when I read about this as your new project was, did you ever see the movie Crimes and Misdemeanors? It’s a Woody Allen film from 1989. Make that sound because I saw that movie when it first came out. I was 17 years old and man, it hit me really, really hard and deeply. And it’s just a profound and incredible film. But there’s a scene in the film where the main character, it’s a flashback scene. He visits his old childhood home and he imagines this Passover Seder taking place at the dinner table and the conversation that’s going on among his relatives.
Eric
And they’re arguing about basically like the existence of God and how they’re talking about. You know, I say the prayers and I go through the motions, but I don’t really believe this stuff. I just do it because it’s a ritual or whatever. And there’s the one guy at the head of the table is like, absolutely unwavering in his faith. And all these other relatives are arguing. But how can you say that there’s a God when the Holocaust happened and da da da da da da da, you know, all these, you know, and and at one point, one of the relatives says to this character, the religious guy says to him, “Saul, what if your faith is wrong? What if you just happened to be wrong?” And his reply is, “I still will have lived the better life through having my faith.” So with that in mind because it’s a useful not true really ism really. My question for you is do you have any spiritual beliefs and you can define spiritual however you want that you choose because you find them helpful or empowering regardless of whether or not they are actually true?
Derek Sivers
No.
Eric
That’s a valid answer.
Derek Sivers
I was thinking are there pseudo spiritual beliefs because actually, like spiritual, like believing in a spirit, being in an invisible realm? No. And I was like, “All right, are there other pseudo spiritual things I believe.” I used to, but now no. But then this is what I find useful. So I’m totally in favor of people who do. In fact, I really love that people do. The past couple of years, I’ve been reading a lot about religion.
Eric
You read the Bible cover to cover?
Derek Sivers
Yeah, Cover to cover. Thanks to Kevin Kelly. Actually, he was the one that suggested I do that and guided me a bit through doing it. I haven’t read the Quran, but I’ve read a book called “What Everyone Should Know About Islam”. It was like a 300 page book in FAQ format, answering a bunch of questions about Islam. I’ve read a couple of books about Buddhism, which has so many different interpretations of what that even is. And Judaism, right? A whole the Dummies guide or whatever, the Judaism for Dummies, something like that. And learned a ton. I tried twice to read a book about Hinduism and it’s so confusing, but I was just in India for a week, so I asked so many people so many questions and I’m starting to understand that one a little better. So I find it so useful. In fact, the book I’m currently reading is called “How Religion Evolved” by Robin Dunbar I think. And like literally when we finish this conversation, I’m going to go grab a cup of tea and get back to that book. So I find religion so useful and so wonderful. I’m so glad it exists. I was just raised without it and it’s hard to take it on later if you weren’t raised with it. So. Yeah, that’s my answer.
Eric
Interesting. Yeah. I just thought of a useful, not true belief. You could decide that people are mostly or inherently good, and you might not be able to say that that’s absolutely true. But you might say by believing that or choosing to look at it that way, that you’re going to behave in a certain way that’s going to benefit you and everyone around you. And so therefore, that would be an example, right? Of a “Useful Not True”.
Derek Sivers
Yep, perfect. Yeah. And honestly, that was my long pause before. No, as I was trying to think, do I have beliefs like this that could be called spiritual? Like I ran through them quickly in my head and I said, “No, I don’t think any of those are considered spiritual.” They are belief systems that can help me get out of bed in the morning and do what I do and belief systems that can help me be nice to other people and find peace of mind and all those things. But I would never argue that they’re true empirically and lots of the book. You’ll see I spend like the first third of the book saying like, “This is not true. That’s not true. This is not true. That’s not true.” But for each one I say “But it’s useful because.” You know, loyalty is not true. It’s like a thing that we invented. It’s not like a physical reality that an alien or an octopus could observe, but it’s a useful mindset to keep us committed to people or places or paths when times get hard and we might be tempted to give up on them if we believe in the concept of loyalty. And if you value loyalty, you’ll stick it out during the hard times. So but know that you’re doing it for these reasons, not because it’s true, but because loyalty is useful. And I go through each of the things that I say are not true. I point out how useful they are or how they can be useful because I think it’s okay to say something is not true. For one, it’s not to say that it’s false. It’s more like you said with Byron Katie.
Eric
Yeah. Byron. Katie. The work is what she calls it.
Derek Sivers
Yeah, yeah. And saying, “Are you sure this is 100% true?” Just because it’s not 100% inarguably, indisputably, absolutely, positively true doesn’t mean it’s false. It just means. That there might be another way. It just means--.
Eric
That maybe the guy really is trying to get to the hospital, that’s all. Like. Okay, just two more questions. And Derek, thank you so freaking much for this conversation and for all of the work that you’ve done in the world. I am blessed to be speaking with you, and I’m really just so appreciative that you made the time for it. So thank you. Okay, two more questions. So this one is going to crack you up, but the internet is ridiculous in what you can find on the internet. And what I found on the Internet was an interview that you did, a radio interview that you did on March 15th, 1996.
Derek Sivers
Oh.
Eric
Do you remember.
Derek Sivers
That? No, but I thought my earliest interview was 1998. I have never heard any.
Derek Sivers
Please. Thank you.
Eric
Okay, Well, I’ll send you the link,
Eric
Okay, So it is a radio show called Something Different with Marky Ramone, who was interviewing you and you were and by the way, he was on WECS 90.1 FM in Willimantic, Connecticut, which I’ve never even heard of. And you were like about to go on a tour with Hit Me your band for a couple of months and you were going to be playing gigs or whatever. So you did this show this it was a over the phone interview with this guy. Um, and yeah, so I’ll send you the link, but here’s where it becomes a question. So in that interview, the interviewer, Mark Ramone was talking about your what was then your new CD, the Hit Me CD, Greatest Hits, Volume 17, right? And he was saying, “Yeah, you know, it’s a really upbeat CD. It’s a really upbeat album and you’re going to love it.” And then and then you responded to that and said, I’m going to just like this is part of your response. You said “The first three songs are really fun. The farther you go into the CD, the darker it gets. It gets pretty, pretty dark and twisted. There’s a little darkness buried in there, but it’s all in a cloak of fun. Kind of like me.” What’s your line?
Derek Sivers
So if you’re asking if that’s true, I was just being entertaining. I am not darkness cloaked in fun. I know some people like that. But that’s definitely not me. I was as soon as you said, like I did an interview in 96, my first thought was I was so full of shit then. Like I was because back then if I did an interview, which I didn’t even-- again, I didn’t know that there was a recording of this, but I was saying what I thought would be interesting for the audience to hear, to just make them go buy my album. I wasn’t trying to be honest. I was just trying to be entertaining
Eric
It kind of comes off that way. But I just thought, okay, good. It was a funny thing to just kind of present to you. And, you know, there’s nothing wrong with having a little inner darkness. I think we all do. Right? The shadow. Yeah. You know.
Derek Sivers
Yeah.Yeah , if it was true, that would be interesting to find that I had said something true back then, but maybe there was something else in that interview that was true, but not that. Sorry.
Eric
Okay. And the last question is just that I know that one of the maybe if not the premier like philosophy that drives you, certainly one of your big philosophies is to do what scares you, right? Yeah. This question is essentially at this moment and stage of your life, who is the person you want to be now and moving forward? And maybe enclosed within that question is what is alive for you right now? That is a little scary but intriguing that might be pushing you in a particular direction. You know, maybe there’s not something, but who is the person Derek Sivers wishes to be now? Or next.
Derek Sivers
Let me think.
Derek Sivers
I don’t know. That’s my real answer. Yeah, I’m not sure. I’ll tell you one that comes to mind that just sounds a little shallow because it’s just another place. But I am officially an overseas citizen of India. I have an Indian passport but I’ve never really spent a lot of time there. So I’ve been spending more and more time there and it’s feeling more and more like that’s where I’m going to live next. When my boy’s 18 and goes off to college somewhere, I’m thinking I’m probably going to move to India. But of course when I’m there, it’s like this place is so crazy and so chaotic and so messy and so everything that wow, that’s going to be a weird experience to live there. And so that’s a little bit scary. That’s the first one that came to mind. But I’ll tell you the second one that came to mind, which is to delegate my programming instead of doing it all myself. So even when CD Baby had 85 employees, I was the only programmer doing all the programming myself. I’ve always liked doing it myself. I’ve never liked delegating. It’s something I find great joy in doing, but whenever I catch myself staunchly adhering to a certain way of being, I challenge it. And so I am in the process right now of hiring two programmers from Kenya that I will plan to delegate all of the programming to and I will be overseeing the programming instead of doing it all myself, which is really scary for me. That’s so unlike me. So those are the two that came to mind, but then they both sound like kind of tiny answers, like as if you were to say, “What do you want to do with your life?” And somebody would say, “Eat breakfast, you know?”
Eric
Oh no. That doesn’t even sound that way to me. I mean, it’s.
Derek Sivers
I mean it’s like the shallow answer.
Eric
I don’t think so. Potentially moving to India is a big deal. And also the idea of letting go of control of something that you have insisted on controlling pretty much your whole life, I’d say that’s a pretty big deal. So I think those are great answers.
Derek Sivers
Okay, good. Well, those felt too small to me. Those felt too small to mention. But yeah, I hope they’re useful to others. Ha.
Eric
Derek Sivers. Thank you. Thank you. Thank you. Thank you. Thank you a million times over for just being you and for allowing me to be in your world for a couple of hours and have this conversation which I really look forward to sharing with people. I will put all the relevant links in the show notes so people can find you. And I know that you actively invite people to connect with you and you did that earlier in the show. So where would you direct people who-- oh, and by the way, this whole idea of what’s worth doing, which was the subtitle of “Hell Yeah or No” right to me, what I personally I know you’re not here to sell anything, but to me, what is really worth doing for anyone listening, especially if you’ve made it to the end of this conversation, is go check out this guy’s work. Go look at his website. There’s all kinds of rabbit holes you can dive into in terms of his blog archives, his four books, and I guarantee you that you will find it worth your time, because these are ideas that if you absorb them and then actually try some of them on for size can really, really change your life in a profound way. So I think that’s absolutely worth doing. Where do people go, Derek, to connect with you?
Derek Sivers
Just go to my website, sive.rs. I keep everything there. I’m not a fan of social media platforms, so we agree there. And even now Twitter is leaving, locking down harder. So yeah, just go to my website, sive.rs it’s all there and then there’s a link there to email me. So please do.
Eric
Beautiful. Thank you, Derek.
Derek Sivers
Thanks, Eric.