Keep Talking
host: Dan Riley
reflection, becoming a musician, freedom, success, journaling, solitude, parenting, financial independence, embracing unconventional life choices
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Transcript:
Derek Sivers
Real learning doesn’t happen in the moment when you take in new information. Real learning happens when you have time to reflect on that information you’ve taken in and think about it and think how it applies to your life. And if this, then what? Like if this fact is true, how does this change things for me? How does this apply to my life? That to me is the real moment of learning.
Dan
I remember hearing you say once that I believe it was in high school that I heard you remark that your parents had kind of written you off from an early age as kind of somebody who marches to the beat of his own drum, and that’s a theme I want to talk about today. In today’s conversation, I want to talk a lot about your life and your philosophy of life. But if maybe we could start there about what a young Derek Sivers was like. My understanding is you grew up in Illinois. Your dad was a physicist, if I remember correctly. What were you like from that early age when you were going in a trajectory that was probably weird and unusual for someone who was a teenager.
Derek Sivers
I mean, it started because I knew I wanted to be a musician. And like you know, I got the bug, I was 13 years old, I started playing guitar. I went, “Oh, this is all I want in life. I just want to be a successful musician.” And then that has implications, right? Same as if somebody decided they wanted to be an actor or a painter. You would know from that moment, like, I’m never going to have insurance, I’m never going to have a pension, I’m never even going to have a steady paycheck. And if you know that from the start, it’s just a different mentality. But it also means that as you’re in high school and things are so focused around college prep and getting you ready to get into a good college, I was like, “But I’m not going to college, I’m going to be a musician.” And I guess it just shapes the world in a way that you think, okay, the norms don’t apply to me. I understand how norms being normal it’s for most people that want to do the normal things. But what I want is not normal therefore the norms don’t apply to me. Yeah, that’s the core.
Dan
How did you--- and this is something I have appreciated about, you know, learning about your life. Is there seems to be in your life a in insistence or creating space for you to think internally, journaling a lot to figure out what you want, why you’re doing what you’re doing. And maybe for that first desire that seemed very deep because of how many years you dedicated yourself to trying to achieve that goal, how did you know that? I know that’s a very simple question, but the desire to want to be a musician, was that just burning inside? How did you know with such clarity, this is who you are. This is what you wanted.
Derek Sivers
There are a few interesting things in there. I mean, interesting not about me, but interesting for your listeners that I mean, for one, okay at the age of 14, it just felt like, I love this so much. This is what I want to do. In the same way that I’ve seen some kids get like that with a Rubik’s cube, you know, or lacrosse, you just get fascinated with something and you just kind of nerd out on it. It’s all you want to do. So all I cared about was this guitar and you know, the finger patterns and the chords and the playing this part. And I dove into that. And as I got deeper into it, then I got interested in the arrangement of the music and combining instruments and started learning about basslines. And then that got me into learning about drum parts and then that got me into learning about songcraft. So it was really just nerding out above all else. I just felt like this is all I want to do. I don’t care to go to a college and learn management there. I just want to get into this. But then you immerse yourself in the media of other people that have done that. So these days it would be like diving down that YouTube rabbit hole.
Derek Sivers
But at the time for me this is the 80s. So it was like magazines. So I subscribed to every music magazine and I would buy books with interviews with famous musicians, and I would read and just hang on their every word, you know, tell me the way, tell me how to get there. So then I found myself surrounded in the thoughts of Frank Zappa or Eddie Van Halen or Brian Eno. And hearing the way that they thought about the world, and then that would influence the way that I looked at the world, because, you know, I would hang on the very words of Paul McCartney to give me an outlook on life, right. And so that shaped the way that I would see the world. The reason I paused a few minutes ago and I said, this is an interesting subject for anybody, is I try to remember this as a parent, that the fact that I wanted so badly to be great at music was the best thing that happened to me. Because all the way from age 14 to 29, I was single, focused. I didn’t care about anything else but being a successful musician. But that was such a blessing because it kept me focused during a time when most people are just lost.
Derek Sivers
When I went to my ten year high school reunion at the age of 28, I was a full time musician touring around the northeast. I did about a thousand gigs around New England, upstate New York, that area. And I got word of our high school reunion and it was at a time when I actually had a gig out that way anyway, so I was like, “Perfect. I’ll just go a little farther. I’ll go to Chicago, I’ll show it to my high school reunion.” And I went and even though looking back, everybody was 28, they looked like they were 40. They were all like chubby wearing suits, looking like old, you know, tired 40 somethings. And they all had these dumb jobs pushing papers from left to right at Motorola. And they looked at me in my crazy tie dyed long hair musician get up and a bunch of them said that they were jealous of me, that I stuck with my dreams and I’m sure they were making way more money than me. But they’re like, “Wow, man, you always said you were going to be a musician and you did it.” I was like, “Well, yeah, I was like, what the hell happened to you? What happened to your dreams? What the fuck is this? Working some management job.”
Derek Sivers
Now it’s like, I’m kind of being this wise old man with an open email inbox, and I get emails from 20 somethings around the world. I realized how many people are lost, and I think that if they would have had even anything, even if it’s like I said, Rubik’s Cube or lacrosse or I don’t know, anything that fascinates you, it gives you a direction. It gives you, like, a reason to be great at anything. So sorry. Let me put this a different way. Learning how to be great at anything, teaches you how to be great at anything. So it could be anything that you throw yourself into completely and get really, really good at, it teaches you how to focus. It teaches you how to learn, teaches you how to practice. It teaches you how to filter the world through this thing that you want to master. It’s like the path of mastery is so useful, so handy. It really just helps everything else in life and I think even for further pursuits later. So I don’t do music at all anymore. But learning how to do music like I did helped me learn how to apply myself to anything else.
Dan
I was thinking about this yesterday, about how this idea kind of came to me, about just me being such a fan of your your work for so long that as I have gotten older, I have tried to take advice from people whose ideas I respect, but also whose lives I would be interested in emulating in some way. People who are happy, energetic. You know, if I know you have that this essay called “Smart, happy and useful”. And to me there’s a similar thread or similar outlook I try to have on people who I listen to because it’s one thing to have good advice. It’s another thing to radiate positivity in the world. And I think for all of your fans across the world, you just talked about your open inbox and all the people I know you’ve been emailing with for years. To me, and I bet I speak for many of them, there’s something to me in watching you over the years that you seem not to have lost that wonder from childhood, that there’s a joy to your work and your output and your ideas, obviously, I’m sure you know no one’s perfect, no one has a perfect life in that way. But I wonder for you, as you made the decision to be a musician, and I want to get into how you switch from being a musician to kind of becoming an accidental businessman. How you made that transition, because my understanding is that all you wanted to be for your whole life was a musician you just talked about, I think from 14 to 29. What was the light bulb moment for you that it was time for something else? 15 years is a long time, and probably an adequate amount of time to gain mastery in something. But how did you know it was time to switch to something else?
Derek Sivers
Well, for one, it was just an accident. I didn’t deliberately switch to something else at first. I think it’s important to listen to the world. And I don’t mean this to sound new agey, but sometimes the world seems to be giving you indications that it wants you to go a certain way. Not to anthropomorphize, but I mean, like there are certain actions that you might be taking that are getting more rewarded than others. So whether it’s getting more money or just more people are giving you gushing thanks or more doors are opening this way than that way. You can just take this as a hint that maybe your natural inclinations, or maybe just the times or opportunities, or where you have found yourself in life are leading you this way, or you will be more rewarded if you go this way instead of that way. You can guess where this is going. So after 15 years as a musician, I liked it. I’m glad I did it, but it was hard the whole time. It always felt like an uphill battle. It always felt like every door was locked, and I was trying to bash my way through locked doors or try to figure out how to pick the lock metaphorically. And then when I built this little online store to sell my CD, and instantly three of my other friends in New York City, other musician friends said, “Whoa, dude, could you sell my CD?” I went, “Yeah, sure.” Oh, “Hey, man, could you sell my CD?” “Oh, yeah.”
Derek Sivers
And I was doing these favors for friends. And then right away, strangers started coming from across the world saying, “Oh, I heard from a friend of a friend that you could sell my CD. Please, could you do this? Oh, my gosh, it’s such a great service.” And the thanks that people were giving me, “Oh my God, this is amazing that you’re doing this thing. Thank you so much. Is it okay if I tell my friends?” Contrast that with 15 years of this uphill battle and locked doors, I went, “Okay, this is not what I wanted, but this seems to be dropping in my lap.” You hear the same story sometimes from people who have an accidental success doing something. I mean, wasn’t Steve Jobs trying to--- he was trying to be a yoga teacher. But then Steve Wozniak said, “Hey, uh, friend of mine, computer store wants me to build a computer. You want to help me sell this thing?” So. I went, “Huh this is not what I wanted, but it feels really good to make people happy.” Ultimately, even us introverts are social creatures, and we kind of can’t help being affected by so many people saying thanks and happy to open their wallets and give you money to do this thing, because nobody else is helping them do it. So luckily, this came after 15 years. Like if this had happened too early. Like if I had just set out in the world to be a musician and I was beginning this journey, I probably wouldn’t have been receptive.
Derek Sivers
But after 15 years of touring, I was like, “Yeah, that would be a nice change, wouldn’t it?” And even the tech side, you know, I’ve got a thirsty brain and after 15 years of driving the van and unpacking and getting on stage and singing the same songs, suddenly I was like learning HTML and SQL and learning how to put pages together and CSS to make them look better, and then PHP, because I had to make it dynamic. I went, “Oh my God, this is so interesting. There’s so much to learn.” Setting up a Linux server for the first time and it was just more interesting. So then I noticed that universities that I used to play at were calling, asking me to come back. And I went, “Oh, actually, no, I’m busy with other things now.” So that’s when I started turning down gigs, quit my job at the circus, started turning down gigs for my band, told the band, “Sorry, I’m just going to do this new thing.” And yeah, CD Baby started very reluctantly like that. So it was eventually a decision. But at first it was not. I was just noticing that the world was rewarding me. So I think the lesson in there for anybody is sometimes the world is trying to make it clear to you that it wants you to go a certain way, and people are thanking you for this direction, or rewarding you this direction, even if it’s not the direction you intended.
Dan
Yeah, I know a concept that you write about a reasonable amount is the concept of having enough or enough in general. And I know I found the story that I’m familiar with, of you writing about having enough specifically to money to be able to pursue the projects and the life that you were interested in came far sooner than I think most people who are familiar with your biography would think it did. And if you wouldn’t mind, I would love to get your rehashing of that moment for yourself when you felt like you did have enough money to live the life that you were interested in, and just how you think about the concept of having enough. A lot of people who probably will come across this, I would imagine have an instinct towards being creative in some way. And I’d love for you to share anything that comes to mind related to that.
Derek Sivers
Sure. The first to give a bit of context. The circus I joined when I was 18 years old, based in central Massachusetts. I was living in Boston. It was run by a husband and wife that probably had, I don’t know, $5,000 in their bank account, just enough to kind of put together the next gig and pay rent on a house that they were being rented as a favor because they were supporting the arts community. And so a woman that owned the arts gallery had a loft upstairs, and that’s where they stayed. And she charged them just a few hundred dollars a month rent. My old boss at the circus swore that he would never spend more than $1,000 on a car, and so he would buy a car for $1,000 an old beat up used thing and just drive it into the ground. And whether that was six months or six years, then when that thousand dollar car died, he would find another car for $1,000 and just drive that. And then my girlfriend, who I met at the circus, she was a face painter at the circus, we were practically married. We were together for six and a half years. Her family were classic Vermont hippies that never had a job. They built their own log cabin deep in the woods, and her dad did odd jobs as a part time photographer for the local village newspaper, and her mother did odd jobs as favors to people, like fixing sweaters or selling pottery.
Derek Sivers
And together they raised a daughter and got scholarships for her to go to college. So these are the people that I was around. People being resourceful and scraping by and living on $20,000 a year. So then I moved down to New York City and get a job working inside Warner Chappell Music Publishing, in the heart of the music industry. And it was $20,000 a year, and I was psyched. And so I found an apartment in Queens that I split with three guys. It was like a three bedroom apartment, one bedroom each. The rent was $1,000 a month, so we split it three ways. So $333 a month was my rent. And I never in the ten years I lived in New York City, I never once took a taxi. I almost never ate out. I would only just make my own sandwiches at home. And I lived in New York City for under $1,000 a month for years. And because of that, I was able to save, you know, my minimum wage job at $20,000 a year, plus doing some gigs with the circus meant I was able to save up $12,000. And I remember when I hit that amount of $12,000, I was like, “I can afford to quit my job now.” And so I did. So I quit my job and I became a full time musician. And even then, doing some gigs, I learned how to get better at marketing and getting gigs and negotiating and getting a higher price.
Derek Sivers
I saved up, I think $25,000 or something like that. I was like, “I’m really all set now.” Like, no matter what happens, even if I don’t get a single gig for a year, I can afford to live for a year on my savings. But I know I’m going to keep getting gigs. So I’ve really got a nice cushion now. And that’s when I’ve felt rich really, ever since then. Everything since then was just on top of it. So I started CD Baby, as I told you, kind of by accident. But I didn’t need the money. I had gigs, so I was able to say no to anything that I didn’t want to do. I didn’t have to make the decision to choose an option. Like there is a early in the days of CD Baby, somebody was willing to pay me big money to warehouse and ship porn DVDs. I was like, “Absolutely not.” He’s like, “Dude, this is big money. Seriously. It’s like, come on, my friend is willing to pay this much money. Oh my God, it’s a ton of money. You’re already doing this. You just added on to your existing thing.” And sure, I looked at the numbers. I was like, yeah, I could probably triple our income, but I don’t want to spend my life shipping porn DVDs. So no and it was kind of nice that I didn’t have to chase the money.
Derek Sivers
Yeah, maybe this is just coming from this deep sense of enough, but I think it was more like maybe always from the beginning. And maybe it’s because of the where we started, your very first question. Because I always saw the world through the lens of a musician or somebody wanting to be a successful musician. I knew from the beginning that this is not a path to riches. Money is secondary. If you choose to be an artist, you’re choosing to make money secondary. Sorry to to make your art the first priority and make the money the second. Otherwise you would make different choices in life. So it probably always came from that. To me, money has always been like the odometer on your car. It’s a number that you occasionally look at and go, “Huh?” But it’s never the point. And I think if somebody is looking at the odometer on their car and they think that’s the point of life, then they start doing stupid things like setting up some ridiculous thing to spin their wheels at night while they’re sleeping just to make the odometer go up. At that point what are you doing? You’ve lost perspective on what it’s all about. So that’s what money’s like to me. And so whenever somebody comes to me like, “Hey, here’s something you can do to make money.” I’m like, “What? No, what are you doing? You’ve lost the point.”
Dan
You mentioned earlier what it was like to go back to your high school reunion and talk to a bunch of 28 year olds who felt like they were 40 years old. And I’ve heard you talk about people who the point of their life becomes making that odometer go up and up and up and up. That that becomes the driving force of their, you know, behavior day in and day out. If you are to believe that someone’s values are indicated by what they do, that seems to be what their priorities are. And I believe I remember hearing you say this once, that you view that kind of mentality as akin to hoarding. And I wonder if you could maybe expand a little bit on that, because I don’t know how not everybody is inclined or wired to be an artist or has a calling to become a musician or something else. But my instinct is that a lot of people’s misery is often stemming from the fact that their priorities are a bit out of whack. I guess I’m mostly speaking about myself in the times where I’ve been most miserable. It’s because I don’t think I’m probably prioritizing the right things in life. And so I’d love for you to comment if you’re open to it on that idea of of hoarding. I know you just alluded to it a little bit, but in relation to money specifically and anything that you think might be related to people you’ve met, including the people at your high school reunion who seemed like they were slowly dying.
Derek Sivers
Sure. First, I should say. I don’t think people are necessarily wrong just because they’re pursuing making money. So, the author, Mark Manson, who wrote “Subtle Art of Not Giving a Fuck” he and I are friends, and he likes playing video games. And he said, “Dude, I love pursuing money.” He’s like, “It’s the same thing as just trying to get a high score at the game.” He said, “I don’t take it too seriously. It’s like a game. But yeah, I want to get the high score. I want to see if I can hit a million on this game. It’s the same thing with making money.” He said, “I just kind of find it fun. I want to make that score go up. I want to see if I can do it.” And I read a couple different biographies or autobiographies of Richard Branson from Virgin, and he also seems to have the same sense of fun. He just finds it fun to make money, “Let’s try this. Sure. Screw it. Let’s do it. Let’s try it.” And so I don’t want to villainize people who are setting out to make money. You just got to know your own internal compass and whether this pursuit is fueling you or draining you.
Derek Sivers
Kind of like somebody who goes to networking events or parties. And you have to ask yourself, “Is this making me exhausted or is this thrilling me?” You know, it’s kind of that question of the test, “Are you an introvert or an extrovert? Well, when you go out to a party, does it drain you or fuel you?” So same thing with pursuing money. For some people, like Richard Branson, maybe Mark Manson, it might excite them and fuel them. For me--- yeah. So that was my preface, my precursor. But let’s say for the people that it is not fun, fun, fun. The other thing that might be going on is who you’re around. We see ourselves through others eyes and we see ourself in relation to others. So when I told my tale about being at the circus where the people I was around were scraping by, living off of, you know, $10,000 a year. To me, $20,000 was great. I was super happy with that. But now imagine if I grew up in Beverly Hills and my parents were Will and Jada Smith.
Derek Sivers
Then it might just be that, like, all my friends had Ferraris and everybody was a millionaire except me. I would see life differently then. And I think that’s the danger of surrounding yourself with rich people. Even on Instagram, for example, if maybe all the people that you’re following are either rich or pretending to be rich. And you think that you are somehow deficient for not being there, well, then that would shape how you want to be. You’d feel like you’re below average. You need to at least just get normal, at least make a million, you know? Otherwise, what’s wrong with you? So it depends who you surround yourself with. Surround yourself with and who you’re trying to be. But okay. So that’s precursor number two. And then the final point is, it really helps to ask yourself, why you’re doing what you’re doing. And make sure it’s for the right reasons, not just to please other people. Because other people don’t care about you. Nobody cares what car you drive. Everybody cares what they’re wearing, not what you’re wearing. Everybody cares what they’re driving, not what you’re driving. You really don’t matter to other people.
Dan
Let’s talk about this, I alluded to this, I think, a little bit earlier in our conversation about th the importance of quiet and journaling in your life, and just the role of solitude that seems to have played in your personal development and desire to make decisions that are in alignment with you. And obviously a lot of people, I think, do that in their life to try to understand what is really motivating them, to help them get a better handle on what they want to do with their life. What what’s bothering them? I know personally that’s been a big part of my life for many, many years. And I wonder if you could comment on the role and importance of journaling and solitude in general for you, because my read on your life is that I know you’ve written about how a lot of your most productive and and even happiest times in your life have come in moments of great solitude. And I can relate to that myself to some degree. But I’d love to have you comment on solitude in general, and the role of journaling in life pivots for you, in getting clear on priorities. Any aspect of that that you would like to speak to or expand upon. I would love to hear as well.
Derek Sivers
Great. By the way, sorry, I don’t usually monologue so long, but you have been asking some really wonderful, heavy questions that have so much to dig into that. Sorry. I’ve been going on a bit longer than usual, but thanks for the great questions.
Dan
I love it. Thanks, Derek.
Derek Sivers
Reflection is the key. I’ve noticed that real learning doesn’t happen in the moment when you take in new information. Real learning happens when you have time to reflect on that information you’ve taken in and think about it and think how it applies to your life. And if this, then what? Like if this fact is true. How does this change things for me? How does this apply to my life? That to me is the real moment of learning, not just the initial taking in of information. So that’s actually part of my problem with the podcast format. No, let me take that back. That’s my only problem with the podcast format, is when I go on a long walk and put on the headphones and listen to a two hour long podcast, I get back from this two hour long walk going, “Oh my God, there’s just so much to take in.” I’m going to have to go through a transcript of that in order to really get back to those pieces and reflect on that, because as the speaker keeps speaking, I don’t have time to stop and reflect. I think that’s why I still go for books, is because I read a sentence and I go, “Whoa, that’s good. Hold on a second.” And I underline it. I copy it into my notes, and then I sit with my diary later and I reflect on that. And I think of how to apply that to my life. That to me, is where all the real learning and growth has happened, is in the reflection.
Derek Sivers
So therefore it’s essential to put aside time for that reflection. That is not downtime, that is priority time that is crucial to give yourself time to reflect like that. If you have kids, it’s after they go to sleep or before they wake up in the morning or while they’re at school. Or if you go to an office to work, it’s that like phone off closed door I’m not available time. That you need to get into the mind space where you are the top priority now, other people’s needs are just going to have to wait because you need some time to think and reflect. So for me, I keep a text file diary every single day. I wish I would have started it whenever, 40 years ago. But instead I started it 12 years ago. It’s one of my few regrets in life is that I didn’t start doing this earlier. But at the age of 42, when my kid was born, actually, when my kid was born, that that wasn’t the reason. I just remember where I was because it was about six months after my kid was born. He was still kind of crawling around on the floor as a baby, and I found myself looking back ten, fifteen years earlier, wondering, “Was I as happy as I think I was back then, or was it as hard as I think it was back then? Or what was I actually doing with my days back then?” Because I kind of kept a diary, but it was only if I wanted to sort out my muddled thoughts, if I was really confused about something or really conflicted, then I would turn to my diary and it would only be like me spelling out like, “Okay, what’s the problem? Why am I upset? What’s really going on? What’s the decision I need to make here?”
Derek Sivers
So my old diaries from my 20s and 30s used to only be the occasional entry like that, but it didn’t give any indication of how I was spending my days. So at the age of 42, wishing I had that diary from 10 or 20 years earlier, I went well, better late than never. So now I keep a daily diary. Where I always put aside time. No matter how hectic life is, I always put aside time to write my daily diary of just like what I did, what I was feeling, what’s going on. But then the deeper issue, like the decisions you have to make in your life, like where to live. Whether to get involved in this romantic relationship. Whether to have a kid or have another, whether to break up that romantic relationship. Whether to quit your job and pursue a new thing. These are major life decisions, and they need some reflection. So that to me is where-- I go back through all the wisdom I’ve collected from the books I’ve read, and I rereview it, even if it takes many, many hours.
Derek Sivers
You know what, if I could, I’ll give a real concrete example. Because this is so crucial and was such a good example. A year and a half ago. I broke up a relationship with a wonderful woman that we were engaged to be married. We were planning on having kids. She’s a really good person. She was completely devoted to me. She was wonderful. But something just wasn’t right for me. And we were clashing a lot and. We’d been together for two years, and any time there was some kind of clash, I would make it like my responsibility to kind of mold myself into what she needed me to be. And I maybe could have continued doing that. And when I look at arranged marriages that my friends in India have or tell me about their friends, I see that’s often the way. Like, you just say, “Okay, well, we’re bound for life, so let’s find a way to work this out.” Which might even be like, you know, you don’t need to be my best friend, you’re just my spouse. But we had, like, yet another clash. And so what I did is I said, “Look, I need a few days to myself.” Because we’re living together. I said, “I need a few days to myself. No offense.” So I grabbed my laptop, hopped in the car, and stayed at an Airbnb for a few days.
Derek Sivers
And I reread every book I’d ever taken notes on about relationships and about love and about commitment. And most importantly, I reread every single diary entry I had written since the day I met her. And in my memory I remembered that I had been mostly happy, but just going through a hard time right now. It turns out that I had always felt that way since I met her. That since the day we had met, it had always been a struggle. It had always been hard. But my optimist memory, my sunny disposition made me think that it was only right now that in general it’s great, but just right now it’s tough. But it turns out that, yeah, almost the whole time we’d ever met, it had always been tough. So that’s why I made the really lucid, somber decision that breaking up was the right thing to do. And it was really hard and I had really mixed feelings about it, but I mean, mixed, you know, 80/20 is mixed. I knew it was the right thing to do, but it’s because of the journal. And putting aside the time for reflection that I was able to make that major, major decision. And I’m so glad that I decided that before we had kids instead of after, you know. And it was only because of putting aside the time to reflect.
Dan
And because of all of that effort that you put into journaling, having a reference point for all of those moments that it sounds like you were able to review before making a decision, did that make making that decision, I’m sure, not easy, but at least something that you could be at peace with in a way that would probably not have been possible without all of the effort and all of the information that you reviewed before before making it?
Derek Sivers
Exactly. Yeah. You have to tell the complete truth to your diary. You have to know that it’s for your eyes only. That’s why people ask some time why I don’t blog every day or share my thoughts every day. It’s because most of my thoughts are private. You know? I have to be completely honest with myself, not think that this is ever going to be seen by anybody else. And then you can review that private diary to correct your faulty memory. We all have faulty memory. We all think that the past is true, that it’s a fact. But no, it’s so foggy and so colored. So it really helps to have a daily diary. Okay, but sorry, this has gotten off of your point a bit. I think the daily diary is important, but it’s secondary to your original question, which was the importance of solitude and putting aside time for quiet reflection, which I do it by typing into a text file. You might do it handwriting into a paper notebook or I’ve seen people that just have a little voice recorder might even just be in their phone, recording their voice, or it might just be literally like laying on the couch and staring at the ceiling and reflecting. I think it’s important to write it down for me, but I could see it could be just as effective or almost as effective to just sit. Whether you cross your legs under the Bodhi tree or you just lie and look at the clouds or just to close your eyes on the couch or whatever. To just stop and reflect is so important. I think it’s everything. I think everything I’ve ever learned really has come from those moments.
Dan
I know this is a theme, I wanted to talk to you about as well. And I’ve heard you talk about this in prior podcast interviews too. About the importance of freedom in your life. I was reviewing one of your podcast interviews yesterday, and someone was remarking to you in a snarky way about how wonderful it must be to be you because you have such freedom in your life. And you said, no, it’s not a fluke that this is the case at every opportunity in life or at many opportunities in life, you have prioritized freedom for yourself over additional money, over, you know, probably a more solid physical community in a specific city. And, you know, I have loved just learning from the periphery about how much you clearly, you know, love your son. There’s this sort of famous - and people who follow your work- moment where you were talking to Tim Ferriss and were tearing up about how much you know, he has meant to you. And I know how much you have protected him in some ways from any online attention, which I think he will be utterly grateful for you, most likely. When he’s older and how much time you have given to him. You moved your life to New Zealand, I think, in part to raise him
Dan
But in my understanding that was not something you even thought you would have in your life, that becoming a dad was not in the plan. And if you’re comfortable talking about it, I would be interested to know what that transition was like for you to go from you know, a free person who loves to travel, who loves to find new interests to, you know, this is now a new phase, which it’s clear to me how much you love your son based upon how everything I just mentioned and more. But I guess I’m projecting a little bit. I know if that were me, that would be pretty hard, to make that kind of a shift. And so I don’t know if that’s something you’ve journaled about or remember a lot, but I would imagine there are a number of men who might come across this, especially who are now in this situation where they’re in their, you know, early 40s. And this is the new transition, either by planning or not. And I know you’ve talked about raising your son as being, like, falling in love. Anything that you’d like to add about that or any comments related to that subject, I would love to know.
Derek Sivers
First I got to say it is so, flattering or honored. I always think of honored and flattered is the same word, but somebody told me that flattered means shallow. So I’ll say honored. I am so honored, like, deeply by the fact that you know my initial answers to these things already are that you’ve researched the things I’ve said in the past. It’s really touching. So thank you. It also helps me dive deeper into, like, now that I know that you’ve, you know, the shallow answers, it’s like you want to dive deeper. It’s like, all right, fuck yeah. Let’s dive deeper into this. I don’t have to repeat what I’ve said in the past. Okay so, kids and freedom. Yes everything you said is true. Except the thing that keeps me not traveling is not my kid. It’s actually his mother. Kids are totally fine traveling. I completely reject the truism when people say, “Kids need stability.” Kids need safety. They need to feel safe. But you could live at airports and feel safe. You could move every single week for the rest of your life with a kid, and that kid could grow up feeling safe. Maybe even more so because they’d know that they could hold their own in the Middle East and Africa and South America, wherever you take them.
Derek Sivers
Yeah, kids need to feel safe. But stability, I think parents use that as a-- they blame the kid for the fact that they’re tired and overwhelmed, and they don’t feel like traveling the world right now because they’re just trying to get their kid to eat. And so they say kids need stability as an excuse for why they’re not traveling, even though that’s what they really want. They blame the kid. But no, we traveled a lot with my kid. After he was born. I’d say for the first year we traveled a ton. And then it was actually his mother that said, “I’ve changed my mind, I hate traveling, I never want to travel ever again. I just want to stay here.” And I went, “What? You traitor! This was the whole plan. Like I’m a nomad at heart. I want to keep moving every year for the rest of my life.” And she said, “I know, I know, but I’ve changed my mind. I just don’t want to.” And so my kid and I love traveling, so every time he has a school holiday, he’s like, “Can we please go to Africa? Can we please go to China? Can we go to the Middle East? Can we go to Europe?” And I always say, hell yeah.
Derek Sivers
So his mother has a job like a regular 9 to 5 job that she can’t take all that time off. But, you know, I can. So every time he has a two week school holiday, we go to some country that he’s curious about. So we actually just got back from China. In January, I took him to United Arab Emirates and Oman. In October before that, we went to Japan. Before that we went to Australia. So he and I love traveling. And he often says, like, “I wish we could just live like this, just live around the world and just keep changing, like, live everywhere for three months at a time.” So that’s not to do with kids. If it was just me and him, we would keep traveling. So his mother doesn’t want to, and that’s that. Yeah. Sorry. I think in talking about that, I might have forgot you had another aspect to that question.
Dan
Well, I think just the time shift from being someone who, you know, as an individual owns all the hours of your waking life to, I think I’ve heard you say, right, like you were spending 30 hours a week with your son.
Derek Sivers
I still do.
Dan
And still do, so that that shift for you personally. I don’t know if that was something that was, you know, initially something you feared or was painful, obviously, like caveating all of this with the fact that it sounds like you and your son are extremely close and very good friends. But that change in your life personally from not planning to have kids, as I understood it to now a big chunk of your life is about your family is about your son. What do you remember about that, that transition for you personally? If the challenges, the benefits.
Derek Sivers
That transition still happens every day. It was not a one time shift. Sorry, I don’t know. Do you have kids?
Dan
I don’t.
Derek Sivers
Okay. So please know the thing that I said earlier about, like, you can keep traveling with kids. In fact, it’s great. In fact, I prefer traveling with kids. It is so cool to see new places through their eyes. It is so cool how it opens up local cultures to you. If you’re just like a solo dude traveling, the world might not be as open as if you were a dude with a kid. And so they’re like, “Oh, come here.” You know, it’s like people are so nice to you when you have a kid. Okay. So traveling with kids is great. Kids would probably be happy to grow up all around the world. But now the time thing. Yeah. Every day, as much as I love my kid and I’ve been honest with him about this, I love him all the way. But I get up early, like 5 a.m. and sometimes earlier if I can, and I go straight to work right away. I start working on my book and then like maybe 6:15 in the morning, some days, 7:30, some days 6:00, some days, 5:00, I’ll hear his bedroom door open. And my first thought is always, “Fuck, ahh okay.” I’m like, okay, that’s the end of me time. And as much as I love him, there’s always a little bit of like. All right, shut down.
Derek Sivers
Pause. This is all going to have to wait. And then he’s just my top priority from that second until he goes off to school or whatever. He gets my full attention because in my value system, and I know I’m not saying this is the only correct way to think about it, in my value system for the way that I want to raise my kid, I like making him top priority whenever we’re together. I don’t like him seeing me staring at a screen. I don’t want him to see me say, “Yeah, yeah, yeah. Go away.” Whatever’s going on in this screen is more important than you. You are secondary. This screen is primary. I don’t think that teaches kids a healthy lesson, in my culture. Although I just finished reading a book, I don’t remember the name of it right now. Wait, wait, her name is Batja Mesquita. So Batja Mesquita wrote a book about cultural differences. She’s a cultural psychologist that studies the difference in psychology between different cultures. And she said one of her colleagues is from Taiwan. And that colleague is a mother that feels it’s part of her duty to let her kids know they are not important because in Taiwanese culture or let’s say in East Asian culture, you thrive by knowing your place, by knowing you are part of the collective and not so important individually.
Derek Sivers
What you personally want is not as important as what’s for the greater good. I used to think this was wrong when I first moved to Singapore in 2010, but now I get it more. So I understand that what I’m saying is just cultural. That for me, for my beliefs, for my kid, I want him to feel very important. And so I make him very important. So as soon as I hear his bedroom door click in the morning, I stop what I’m doing and give him my full attention until he goes off to school. And then I dive back into me time, and as soon as he gets home from school at 3:00, it’s back to him. So, yeah, I still spend an average about 30 hours a week. I just measured it once. Just giving him my full one on one undivided attention. Yeah, you’re right. I didn’t want to have a kid. He was he was an accident, but not a mistake. But yeah, once, my now ex told me she was pregnant went, “What? We agreed. No kids.” She said, “Well, things happen. The pill is not 100% perfect.” And so, yeah, we had a kid, and for the first four months of pregnancy, I was mad. I was like, “No, no, we agreed. No, I am the most important person in my life.”
Derek Sivers
And then somewhere about half way through the pregnancy, I read a book called ‘Brain Rules for Baby’ by John Medina, which was so interesting. And suddenly I kind of nerded out on this idea of raising a kid. I was like, “Okay, actually, this could be cool. This could be fun. Wow. This is actually kind of interesting. This would be kind of cool to watch a kid develop.” And so, yeah, from the second he was born, maybe even before he was born, I was all in. So I’m really thankful it happened when I was 42, and I had recently sold my company, so I was semi-retired or just retired. That made a big difference. So I do kind of snarkily say when people ask me my advice about having a kid, I say, “Well, first retire.” Because I think the hardest thing about being a parent is the clash between kid time and parent time. Kids are just lost. They don’t care what the hands on a clock say what those numbers say, you know. Their fascination is the real time. And if you’re just like, “Come on, we gotta go. Hurry up. I told you to get your shoes on now.” That’s the hardest part about parenting, is that clashing of those times. So instead of trying to force them into adult time, if you can just let yourself fall into the joy of no clocks and kid time, that’s the best way to do it.
Dan
Yeah, I skipped over an important part of your biography, and you just alluded to it just now about selling your company. And this is another example from your life that I think for people that, you know, admire you just come back to about you living in accordance with a personal code or belief system that most people I don’t think would. And specifically the details which my understanding is this kind of needed to be pulled out of you, that sheepishly you conceded the sale price of your company CD baby, which was just over $20 million, and you essentially gave that money away into, I think it was a charitable trust or a trust for musicians to be used. There’s so much we could talk about with that. But to me, it’s one of the reasons why I’ve always admired your example because we talked earlier in the conversation about you having $20 or $25,000 and you feeling like you’re good and now you’ve exponentially increased the wealth at your disposal. And you give away the kind of money that people dream about having and live a what seems like a comfortable but a relatively modest lifestyle, in accordance to a day to day life that seems to generally make you a happy person.
Dan
And I’d love to just give you an opportunity to talk about that moment in your life and why it was that you decided that giving away that kind of money. And to me, there’s something irreverent about you that I’ve always liked. The bucking the trend, of doing things your own way. That makes sense to you. And living your own quirky, interesting life in accordance with your own nature. And so that’s a long winded way of me just asking you to comment on that moment in your life. You still retired, as you just said, where you still had enough money to be able to have control of your your time and your energy, as I understand it. But the decision to not buy the mansion, buy the yacht, join the country club, you don’t seem like somebody who is wired to do that in the first place. But anything you want to add about that moment when I would imagine the seductive devils on your shoulder could have been there to try to entice you into a different lifestyle than one that made sense for you personally.
Derek Sivers
Well, first, I’m glad that you mentioned freedom earlier, because think of all those things you just said a mansion and a country club. Those are all anti-freedom choices. A mansion is a lot to clean, it’s a lot to maintain, even if you’re not going to do it yourself. Now you’ve got to hire people to clean the house and hire a gardener for your grounds. That’s an anti-freedom choice. Yeah, even a country club that’s kind of binding yourself to a place. I mean, hell, buying a house in general is creating gravity for a place. I really challenge the idea of owning a house at all, because by my values, I’d like to feel equally connected to everywhere. I want to feel that Egypt is just as much home as Finland. Which is just as much home as Uruguay. That’s my ideal, is that I would feel equally connected to everywhere. And owning a home in any one place makes you more bound to that place. So take it as a given that we already have friends, and our friends might be in places. Well, okay that’s a binding that is worth it for me. But even just philosophically, I would rather not have a house at all. Okay. So, mansion, fuck, no. Couldn’t pay me to live in a mansion. Fuck that. That’s anti-freedom. So I said earlier that yeah, $25,000 or so I felt I’ve got a good savings, I feel free, I don’t need to do things just for the money anymore because I had a nice cushion with $25,000.
Derek Sivers
There is another level then, when CD Baby kept going for a few years, when it was about four years in. And I realized that I had $1 million in the bank account. And then that really quickly turned to $2 million. And then that really quickly turned to $3 million. That was when we were just kind of really hit our stride. And at that point I remember after $1 million, I was just starting to think like, “Okay, so assume I just stick this into a regular old Vanguard account with an average 8% return, that’s $80,000 a year. That’s way more than I need to live off of. So even if I just stick the million dollars in an investment account and don’t touch it, I’m set for life. Like, I am literally like, I think once I had $1 million in the bank, I was like, “All right, I’m retired now.” Technically, I’m doing everything now just for fun. I don’t need the money anymore. It really helped that-- oh, investors. Again, I’m so glad you mentioned freedom. I kind of forget about this word sometime. I take it for granted. I have never, ever, ever had investors because that’s also an anti-freedom choice. Now you’re bound. You have a bit of an obligation to your investors. You owe them. Fuck that. I’d rather my business take ten years longer to grow. But have no debts and no obligations. I’ve also never had a mortgage. I’ve never any of that.
Derek Sivers
I’ve only ever paid cash because it’s the constant choice for freedom. I don’t want to be bound to hardly anyone or anything. Well, I’ll pick my bindings very carefully. But mortgage? Fuck, no. Investors? Hell, no. Yeah. So sorry. So there were a couple scales. So hit $25,000. I felt now I can say no to things. I don’t need the money. Million dollars I felt now I’m retired. And I had $4 million saved up when I felt done with CD baby. I felt like I had no more vision for the future. I was sick of it. I’d been doing it for ten years, I had plateaued. Seth Godin gave me the nudge. I asked him what I should do, and he said, “If you care, sell.” Meaning if you care about your clients, you owe it to them to sell the company because they want to keep growing and you do not. So that was a great insight and I look up to him so much. So I said, “All right, fuck, I’m going to sell my company.” And I got a few different people bidding against it. The price was $22 million, I could have had more. Amazon was actually offering more. But the company I sold it to, I felt understood my musician clients better. And that was important to me that they were in good hands. So, there was that moment where I talked to my lawyer, who was a friend at that point. He was just a really good guy, and he had a background in tax law.
Derek Sivers
And he said, “Well, congrats, dude, what are you going to do with $22 million?” And I said, “Oh, nothing. I’m just going to give it away.” I said, “Look, that’s way more than I need. I’ve already got $4 million. I’ve already paid off all my debts. I’ve even paid off my parents debts like I’m good, so I’m going to give it away.” So yeah, he’s the one that encouraged me to put it all into a charitable trust. He said, “Look, if you’re really going to give it away, then don’t ever take it in the first place.” He said, “Just have the purchasing company buy your company directly from a charitable trust. So the entire $22 million goes to charity.” I said “Great, perfect. That’s what I want.” So the $22 million never touched my hands. And that’s what I wanted, because it’s just a constant reminder that this is enough. I didn’t want to get so much money that I do stupid things. Even when people ask about, “Yeah. What about your kids? What about future grandkids?” Well, again, I think 4 million is enough. I think if you leave $20 million to a kid again, it’s going to make your kid do stupid things because they didn’t even have to work for that money. It would mean nothing to them. So I think even if you’re looking in long term for inheritance, I think that there is such a thing as too much to leave as well.
Dan
And have you been tempted at all when you had $4 million? And I don’t know if you had this experience, but I was somebody who had zero money. And as I worked personally in startups, in tech. I could begin to eat out at lunch every once in a while, and then eat out at dinner every once in a while. And it does afford a more comfortable life in some ways. And, you know, everyone or many people have heard of this idea of lifestyle creep. Has that been something you have had to personally fight back against, or are you so rooted in your preferences that you know you’re basically living the same life you were living 10, 15, 20 years ago?
Derek Sivers
There are some differences, but I think I subconsciously still filter it all through freedom. That if you get accustomed to business class flights, well then if you ever hit some kind of future hardship, flying economy is really going to upset you if you’ve gotten acclimated to business class. So to me to choose business class at any point means that I’m harming my future, that I’m making my future more fragile. Whereas I would be strengthening my future happiness by never choosing business class and sticking with economy. Yeah, that lets me be more free in the future. My lifestyle would stay cheap. That said, there are some things that I do. I mean, taking my kid to China for a school holiday, you know, that was more expensive than just taking him to an art camp down the road. Or just sitting and watching TV with him for two weeks during his school holiday, you know? So I do things like that, that I am thoroughly grateful for. There was a time once where I had a very, very important meeting. I’ll just leave it vague like that. But there was a super like, crucially, life size meeting that I had to get to in Seattle at 4:00 and I had my usual economy flight booked that left New York that morning. I got to the airport, handed them my ticket, and they said, “Sir, this is JFK.” And I went, “Uh huh.” They said, “Your flight leaves from Newark.” I went, “No, J oh crap.” I was like, “But the flight leaves in an hour. I have to get to Seattle. There must be some other flight going to Seattle.”
Derek Sivers
It’s like every other flight was going to get me in after that meeting. And they said, “Well, there is one that leaves in 30 minutes. It’s only business class. It’ll cost you $4,000 to get on that flight.” I was like, “All right, fine, put me on that flight right now.” And I was thinking, “God damn, that’s a good use for money to be able to just put me on the $4,000 flight and not sweat it.” I was so thankful. I was like, see, I have no interest in status or impressing others. I never buy anything to impress other people, but to be able to use money to reduce your downsides, to reduce your chances of disaster and unhappiness. It would have been a disaster if I would have missed that 4:00 meeting in Seattle. Okay. I’ll just say it was a wedding. It was my wedding. So sorry, just to put this in context,
Dan
That’s quite, quite the meeting.
Derek Sivers
Yeah. Okay. I was trying to be vague. I just realized why, there’s no need to be. Yeah, it was my wedding, was at 4:00 in Seattle. Yeah, it would have been that big of a disaster to miss. And so yeah, $4 000 bucks to make that. But that felt like splurging. And yeah, I was sitting in a business class seat that I had booked 30 minutes before with a credit card at the gate. And I was like, “Yeah, that felt indulgent.” But damn, I’m glad that that didn’t make me go broke, you know.
Dan
Yeah, that word freedom. I’ve said this story before on this show, in a prior interview there’s a terrific-- you may have come across this book, but the book, “The Psychology of Money” by Morgan Housel, which most people have heard of. There’s a story he tells in that book about, and I know you’ve spoken about how your kind of innate tendencies align with more of a stoic philosophy that you learned about later in life. And Morgan tells the story about his parents, who lived very modestly, and his dad, at the age of 40 with three little kids, decided that he wanted to become an ER doctor. So at 40 he went to medical school, became an ER doctor, you know, six, seven years later and his entire childhood and young adult life, they continued to live exactly how they had basically before he started earning more money as a doctor. And when he was in his mid 60s or so, as Morgan tells the story in the book, he was tired. He had had enough, working in that field, as you know, you alluded to in your life before and because he had not bought the McMansion, bought the boat, bought the fancy cars. He had the ability to leave and quit in a way that many of his coworkers didn’t. And I don’t mean to lead the witness here, but in terms of the why freedom matters to you as a bit of a North Star or why that’s something that you’ve tried to prioritize in your life. Is it for that? Is it for the ability to control your time and energy and not feel locked down? Is it something else? When you think of that word, why does that resonate so much? Why has that been such a priority for you?
Derek Sivers
It is just what you said. Yeah, it’s the long term thinking. It’s thinking long term. I always want the ability to just never have to do anything I don’t want to do. And that’s why I don’t want a mortgage. That’s why I don’t want an expensive life. Because that might make me need to do things for money that I don’t want to do, because I’ve gotten acclimated to a certain quality of life. So in order to secure a future with less obligations. I make sure I don’t get acclimated to an expensive life.
Dan
Yeah. I don’t know if you’ve had this experience, but I would imagine that your example may at certain moments in your life have elicited some envy. Or at least passing snide, snarky comments from people who look at your lifestyle and say, “Must be nice to be you.” In other words, that you know your life, which is filled with seemingly books and friends and family and time to pursue your own interests, that not everybody gets to live that life. And I know you’ve spoken a lot about how luck has played such a role in your life. But to me, it seems like it was a combination of luck and intention coming together to afford you with this kind of lifestyle that, you know, some degree, on some small level, I’ve been able to enjoy in the last few years, too. And if you agree with that statement or if you have experienced some pushback from people or just, you know. You’re obviously such a lovely guy, such an enthusiastic guy. But if you’ve gotten any negative feedback from people who are in your life about how you live and especially people that you care about, how have you navigated those waters and maybe you haven’t dealt with that at all, but if any examples come to mind, how have you dealt with envy or just a degree of anger at the fact that you’re you’ve created such an incredible lifestyle that suits you for yourself.
Derek Sivers
It’s funny, I find myself. In between a handful of friends that think I’m really rich, and a handful of friends that think I’m not. Meaning it used to be that all my friends were broke musicians, and now some of my friends have become really successful. You know, we talked about Mark Manson or Tim Ferriss or whatever. Even just, you know, some of my friends that are not famous but are very successful in their fields and they kind of tease me for living in this shitty house I live in. And only having one pair of pants. And I travel with nothing but a little carry on bag, and I fly economy and all that. Like they tease me like, “You’re crazy dude. What the. Come on. Oh, my God, you’ve got millions in the bank just get a good night’s sleep buy the business class.” I’m like, “No, I refuse.” And they say, “So you’re able to sleep in economy?” I say, “No, if it’s an overnight flight, I don’t sleep. I stay up all night.” They’re like, “Yeah, but aren’t you exhausted the next day?” I’m like, “Yeah.” But oh my God once I started giving money to charity, and I found out that it costs about $2,000 to save a life when like, literally there are people dying of malaria that if they had mosquito nets, they would not die of malaria. And it costs about $2,000 to buy enough mosquito nets that on average will save a human life. And you look at your $6,000 business class flight, you say, “Okay, so I’m going to get a good night’s sleep. You know, three people will die, but fuck them. I’m going to get a good night’s sleep.” I just can’t put that into my value system.
Derek Sivers
I can’t not care about people dying. And so, I do give away almost everything I’m not using, so that other people don’t die. And when I look at the economy versus business class, you know, of course. Okay. But I don’t want to do the bullshit guilting of people who choose that. We all have our own value systems, and I’m sure that somebody could make a perfectly moral argument for why we should never give anything to charity and why we should only look after ourselves, whatever. And it would be a valid argument, too. So I’m choosing my own stance on this that makes me happy. I don’t really care what other people think, though. I’m really top to bottom congruently happy with who I am and don’t give a shit if somebody is jealous or if somebody thinks I’m an idiot. Either way just doesn’t matter to me. I would like to someday, just as a curiosity, in the same way that I want to understand Arab culture or I want to understand what it’s like to grow up in Mexico City or something like that. I want to understand people who care about status. I do not get this. Like at the core, I have tried. I do not understand status seeking. And just a few weeks ago I attended a little conference where they asked me to come speak and it was right nearby. And after I spoke, I was sitting around with a bunch of people I think were like 6 or 7 people were kind of sitting around some couches and talking.
Derek Sivers
And they were good people, interesting people. And one of them said, “Where’s your watch?” And I went, “What? I don’t have a watch.” He goes, “I know. That’s why I’m asking. Where is your watch?” I said, “What do you mean?” He goes, “You’re the only one here without a watch.” And I looked around and he was scoping out everybody else’s watch. He’s like, “Oh, he’s got the Philip Patek. He’s got the Rolex. He’s got the something, something. Where’s your watch?” And I was like, “I hadn’t looked at people’s watches. I don’t do that. I also don’t look at wedding rings. I don’t know, my eyes don’t go there.” And suddenly I looked at this group of people I’d been talking with for an hour, and I went, “oh my God, you guys all have watches.” And so to the guy next to me, I said, “Wait, I’m so curious, why do you wear a watch?” I said, “You have a phone, right? You know what time it is? Why do you need a watch?Like, I don’t get it.” And he goes, “Oh mate, it’s like a status thing. It says I’ve arrived. It shows that, you know, I’ve achieved my dreams. I can afford this Rolex kind of shows that I’ve made it.”
Derek Sivers
I thought he was kidding. Like I laughed and he goes, and you know, we had a little back and forth or I realized, “Oh my God, wait. You’re serious?” He goes, “Yeah, you know, I worked hard in my life. I wanted to show that I’ve arrived and show my status.” Whoa. I don’t get this at all. And then, you know, I went to China, which is very status focused. And we were in Shanghai, and just the subject came up again about showing status, and I don’t get it, I just don’t. I’m not trying to show off. I’m not trying to do some kind of anti signaling or counter signaling. I really just, I would like to understand the mindset of trying to show status to others, because I don’t even understand why you would care who would be impressed with a Rolex and why would you care about the opinion of anybody who’s impressed that you have a Rolex? Like what talent does it take to buy something? It takes no skill at all. Any idiot can buy a thing. It doesn’t show any mastery or skill. I don’t get it. So, I would like to understand that listeners, if anybody listening to this, if you want to explain to me the mindset of status, I really do. I’m not trying to knock it. It doesn’t work for me, but I would like to understand it in the same way that I want to understand Islam or whatever. I’d just like to understand different mindsets.
Dan
That dovetails into one of the final things that I wanted to talk to you about. There may be two subjects I’d love to get your time on. I know we’re a little bit over on time
Derek Sivers
No, I’m in no rush. Take your time.
Dan
Right. The idea and I just reread an essay you wrote about the concept of success. And I think this was in a conversation you may have had with Tim Ferriss where you were talking about success in general, and you were making the comment that when people think of success, you mentioned this guy’s name earlier. They often think of somebody like a Richard Branson. But what if Richard Branson actually wanted to be a beach bum who had a quiet life in California somewhere. And he just like an addict, cannot stop making businesses and has that compulsion that is kind of out of control. You just talked about status. And this, I think is related to the concept of how people think about success. And I’d love to get your comments on, in any depth you’d like to give it about what you think success means to you when you look at, you know, your friends or people in life, or probably mostly just yourself, a life that you deem to be successful. How do you think about that?
Derek Sivers
To me, it only means two things. One, that you achieved what you set out to do. And two that you’re living in accordance with your values. And that’s it. Has nothing to do with what other people think. I think, what other people think should be nowhere in the criteria of success. It’s just personal. It’s what you set out to do and living in accordance with your values.
Dan
Yeah, I like that. I want to read a few quotes that I wrote down, which I have come back to many times in my life from you and just read them out for listeners because these are some that there are too many to actually read out. But these are a few of my favorites and I’d love to just read them aloud and then get your thoughts on anything that comes to mind and listening to it. And this is from one of my all time favorite books. I know you’ve written books since then, but, uh, your “Hell Yeah or No” book is one that I’ve read and reread and gifted to friends. So I want to read a few of these and then have you make any comments that may come to mind after listening to this from you. And again, this is from your book, “Hell Yeah or No”. And this is the first quote, “When someone asked me a deep question. I say I don’t know. The next day I have an answer. I’m a disappointing person to try to debate or attack. I just have nothing to say in the moment. Except maybe. Good point. Then a few days later, after thinking about it a lot, I have a response. This probably makes me look stupid in the moment, but I don’t mind. I’m not trying to win any debates.”
Dan
Again to me, like, that’s such a counter modern life online philosophy to have about debating. This is another one quote, “People say that your first reaction is the most honest, but I disagree. Your first reaction is usually outdated. Either it’s an answer you came up with long ago and now use instead of thinking, or it’s a knee jerk emotional response to something in your past.” This is a third one. I alluded to this earlier in the conversation. Quote, “All the best, happiest and most creatively productive times in my life. Have something in common. Being disconnected. No internet, no TV, no phone. No people. Long interrupted solitude.” Another one quote, “Comparing up versus comparing down. Your happiness depends on where you’re focusing.” The metaphor is easy to understand--. I think this is related to thinking like a bronze medalist versus a silver medalist in the Olympics, “The metaphor is easy to understand, but hard to remember in regular life. If you catch yourself burning with envy or resentment, think like the bronze medalist, not the silver. Change your focus instead of comparing up to the next higher situation compared down to the next lower one.”
Dan
This is another one. Quote, “Legendary psychologist Abraham Maslow said it well. ‘Life is an ongoing process of choosing between safety out of fear and need for defense and risk for the sake of progress and growth. Make the growth the growth choice a dozen times a day.’” And then this is just a final piece that I put on my website years ago. And these are I don’t know if you still agree with this, but these were four things that you noted once to be happy. And to me, this aligns with how it’s really often the small things that end up mattering to making an interesting and happy and meaningful life. The four things you need to be happy, “Number one, I need quiet. Number two, I need a decent temperature where I’m not sweating or freezing. Number three, I need to be near nature so I can go out for a walk. Number four I need somewhat of a view. It doesn’t have to be a view from the top of a mountain, but something more than looking at another wall out of my window.” Anything that comes to mind or that percolates from any of those. Obviously you don’t have to comment on it, but I wanted to give you some time.
Derek Sivers
I’m going to replace number four. It turns out I don’t need a view, but I do need a friend to talk to. I found the importance of having a friend that likes bantering ideas. Both ways, you know? So I’ve turned out that’s crucial. That’s way more important than a view. My current office has no view right now. It’s just the tiniest room in my shitty house. I just stare at-- it has no view at all. But it’s small and therefore easy to heat. Which is why it’s my office. Yeah, I agree with all of those still, except the view. Thanks for finding those. It’s really nice to hear those back.
Dan
Very good. Maybe I’ll close with--
Derek Sivers
Wait, wait. Before we close, I gotta ask you. So before we hit record, you told me about how coming to New Zealand kind of shifted your mindset back in 2006, when your friends were going off to work on Wall Street and instead you came here. Have you talked about that on your show before?
Dan
I haven’t, and I would be happy to. This is a good opportunity for that. Yes. I, like you, was precocious and focused and knew from a relatively early age what I wanted. And if you would have asked me at 14, what I wanted in life, I would have told you, I want to go to Duke University. I had no friends who had ever gone there. I had no family who had ever gone there. I grew up in a small town in northwestern Pennsylvania, but something about the probably marketing and allure of that place, began to take on almost like a religious tone in my mind. And to me, it was the goal. Or the North Star or the gaining admission to a place like that was akin to kind of like getting like heaven is kind of how I’ve thought about it since then, and from my first day in high school, that’s what I focused on doing. And I ended up going down there for a summer program. After my sophomore year of high school, I enrolled in classes there between my junior and senior year. I was not someone who was marked from an early age as being somebody who would get into a place like that, and I worked tirelessly and was you know, willingly able to sacrifice in the name of that objective for years.
Dan
And like you said earlier, there’s something about having clarity around what you’re trying to do or what you’re trying to master. That can actually be very helpful in who you become in the act of trying to achieve difficult things. And so I ended up getting in, I ended up going there. And very quickly in the first year or so I was there, it was clear to me that something was wrong. That the probably naive notions that I had about what a place could really do to change an individual life was wrong. I was still the same person. People who were there were smart, but they were flawed people and great people too. But it wasn’t a perfect environment. And so as my really kind of like religious views began to unravel as I was getting deeper into college. I became depressed and lost. I was, you know, doing drugs. And I did a whole episode on on that about how that experience derailed me as well. Just some horrible experiences smoking marijuana every day for years. And when it came time to graduate, I actually didn’t even know if I was going to graduate.
Dan
I had stopped looking at grades for at least the last semester I was at college, I was really spiraling in some ways, and I ended up graduating. And someone who was friends with the girl I was dating my senior year and noted that he loved New Zealand. I didn’t know anything about the place. Aside from the fact that it was halfway around the world and I didn’t know anyone there, I had a few hundred dollars. I worked after graduating from college, and I stayed in Durham and I think saved $500 or $600 and bought a ticket and went to New Zealand. I had zero plan other than that, I just know I can’t continue on this trajectory I’ve been on where I’m mimicking what other people say makes someone a success. Like whatever is going to work for me, it isn’t continuing to work 80 or 90 hours a week. I was utterly miserable and hadn’t, I don’t think, really been taking care of myself very well for a long time and going to New Zealand--. I said this before we recorded too, like I didn’t even know that it was a bit of a reset, but I think it was just an action that, in retrospect, was an indication to myself that I still had a level of autonomy in my trajectory in life and ever since going there--
Dan
And kind of proving to myself that I was someone who was capable of bucking the trend in some small way, just by visiting some island country in the middle of nowhere for half of a year that I could go my own way. And over many years and many failures, I kind of built up a life that was more in alignment with something that was healthy for me and sustainable for me. And I’ve also had very good luck professionally in some areas. And so 18 years later, from the time that I went to New Zealand, and this didn’t really even occur to me until I was having dinner with a friend last Friday night, who is, I think, also going through a bit of a difficult time himself. That at the end of the day, to me, nothing matters more to me for myself or my friends than their, you know, actual internal wellness. How they’re doing on a day to day basis. And I said to him, too, that one of the reasons that was such a difficult time for me was that I had no one to talk to. I was so ashamed of my failure and how poorly I was doing.
Dan
That you know, the one person I felt like I could be honest with was my mom. And I try to tell her that every Mother’s Day that having one person-- you just talked about how important it is to have people, you know, friends to talk to and to be happy and in many ways, I’m grateful for that experience because I think it has informed a lot of my own decisions about my priorities and my life. And I said this to my buddy the other night, too, like, there were many times, years where I didn’t think it was possible for me to have a happy life. And I’m fortunate that that turns out not to be true. Bt, you know, I barely think about that, that era of my life 20 years ago. But it really was a reset and a new start for me. And again, dude, like, I think this is probably partly why I’ve so loved your example. Is that, you know, you’re somebody with a lot of talent and a lot of charisma, and I think you could have pursued many different paths in life. But I think to a lot of other people like myself online who have found your work in your books.
Dan
And to me, this is one of the great things about the living in the internet age. There’s a lot of downside, but a lot of the things that are great about it are kind of like you were mentioning earlier about reading magazines where you were trying to find answers from these musicians when you knew that’s what you wanted to do. It helps to know that there are alternative paths to the ones that are being incentivized to you and encouraged by your immediate community, and that life is negotiable and that you you can figure out your own way. And that’s easier now than I think it would have been 30 or 40 years ago. But you know, I have so much gratitude for my life now, and people like yourself who are just idea dealers. Who I think are very thoughtful people that are excited about putting out countercultural, interesting, thoughtful content into the world because it’s changed me. And I know just from watching other people who have interviewed you, like I speak for many people who you know, feel that way about yourself. So that’s a very long winded answer to your question about New Zealand. But that’s that’s basically the story.
Derek Sivers
That’s amazing. Thanks for that. Thanks for giving the long version instead of making it too short. That was wonderful. That was just right. I think about those key moments where we can take even a small action and how it completely shapes our self-identity. You know, I’ll just make up an easy one. Say you just happen to be walking past a river when you see a little kid falling, you know, baby, fall into the river when the parents aren’t there. And so you jump in to the river and you save the kid. And for the rest of your life, you have, like, a self-identity, as, like, I’m the kind of person that does that. I’m a local hero, or the kind of person that would jump into a river to save a kid.
Dan
Yeah.
Derek Sivers
And in your case. You somewhat whimsically booked a flight to New Zealand. Now, you can say to yourself, “I’m the kind of person that would just book a flight to New Zealand instead of moving to Wall Street and grabbing the first banking job.” And these little actions that shape our self-identity. And I think what my favorite thing to do, or I’d maybe even say objectively, the best thing to do is in the moment when you are at your highest self and taking in some good wisdom, or you’re reflecting. You’re reading a really wise book or taking in some really good thoughts, and in that moment you realize, “You know what I should do or I’m thoroughly agreeing with this wise thought right now. Therefore, the action I should take is this.” And in that moment, you just initiate that little action. Maybe it’s signing up for a Chinese language course or sending an email to your crush or whatever. Whatever the right action is, you just take that first step in that lucid moment. And it’s like there, you’ve initiated it. You’ve booked the flight. The best things happen from those moments where you take the right action in those higher moments, and then all you have to do is just follow through with what you started.
Dan
Yeah, yeah. Let me close with just some final words of gratitude towards you. And then I’d love to close with giving you an opportunity to talk about what’s exciting you, what’s next, how anyone who reaches this might help in any capacity with your work or I know you love having people contact you. It’s it’s an amazing fact about your life that you respond to all of these thousands of people that have reached out to you, including myself. I just said this, but it’s true that your books and I think just your example in general have meant a ton to me. And it’s not just the ideas. I think it’s the spirit of, you know, your personality in dealing with strangers and the internet can be a tough place to hang out, but it’s always inspired me that you have led with such a an optimistic and generous attitude. And I think, you know, for myself, that’s something that I aspire to do as well with people that I interact with both in life and online. And so I just wanted to say thank you again for, you know, all the emails we’ve had over the years, all of the interviews you’ve done in the past, the work that you do. And it’s just meant a lot. And it’s an honor to be able to finally meet you and do this interview. But maybe to close, I’d love to have you, you know, say anything you haven’t had a chance to say to my audience or to people that come across this, that you would like to.
Derek Sivers
I’m thinking about-- I laughed at the internet as a tough place to hang out. Is that how you said it?
Dan
I think I heard that once about Twitter, that Twitter is a tough place to hang out, and that’s probably more accurate than the internet generally.
Derek Sivers
Social media can be a tough place to hang out, especially when people are trying to win favor, gain points with their snarky comments, and, um. I was thinking. And then you said it right after that thing about or right before the thing about me answering my emails. I think the reason I’m able to answer all of my emails is because I am not on any social media. I spend zero seconds per year on social media. And I just spent all of it in my inbox. So I realized, as you were saying, that I am on social media, it’s just a very exclusive social media, which is my email inbox. Which gets a hundred messages a day. But since that’s my only place where I spend time online that’s why I’m able to give it my attention. And it’s a nicer place. Nobody’s making snarky comments to win points for others. I think that’s always surprising to people. If you look at actually, the comments on my blog are really nice, and a lot of people have mentioned that saying, “I’m really surprised. You know, the comments on YouTube are nasty, the comments on Facebook.” And I think, yeah, but that’s because you don’t win any points by leaving a snarky comment on Derek Sivers blog wins you no internet points because it’s not a corporate platform. So maybe that’s why people are so nice. And then same thing with the email inbox. Yeah, I highly recommend this to anybody. It is not as generous as it seems. It’s pretty wonderful to have an open inbox and to hear from people that have found your work and you meet kindreds. I’ve made some of my best friends. Even a couple of the loves of my life were initially met through my email inbox. It can just be like a magnet for kindreds around the world, so I highly recommend the open inbox. It’s wonderful. It’s not as much work as it seems. And then the flip side is just forget social media. There’s nothing there for you.
Dan
Yeah. Fair enough.
Derek Sivers
On that note, yes. Anybody of course. Yes. If you reached this far in the interview, go to my website, sive.rs and send me an email and say hello.
Dan
Very good. Thank you for all the time, man. It was a real pleasure.
Derek Sivers
Thanks for the great questions. That was so interesting. And yeah, I really admire-- yeah, you and I, we didn’t talk about most of your past emails to me on this show. But as soon as you emailed me the first time, I was like, “Oh, yeah, he’s one of those kindreds.” And I told you that. I looked back at our email history and I told you early on, like, just with the kind of stuff that you’ve done and you’ve asked me and that we’ve talked about by email, I was like, okay, yeah, we’re a lot alike. So it’s an honor to do this interview with you. Thank you.
Dan
Thank you man.