Icons by Motiversity
host: Tyler Waye
Definition of success, philosophy of growth and challenge, whatever scares you go do it, developing rare skills, input vs output, simplicity, journaling.
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Transcript:
Tyler Waye
Derek, I'm really curious to ask you this question. I think the people who know a bit about you will be fascinated by your answer and probably people who don't know anything about you will be fascinated. How do you define success?
Derek Sivers
Success is totally up to whatever you set out to do. So if you set out to live a quiet life and you stumble your way into being a billionaire delivering a glamorous Hollywood life of celebrity, well then you failed at your mission to live a quiet life. If success to you is... or it's like if you set out to be a great parent and you start a business that's taking all your time and you're making a lot of money but ignoring your kids, well then you've failed. You were not a success because you want to be a good parent. So success has nothing to do with what anyone else thinks. Success is entirely up to whatever you set out to do.
Tyler Waye
Part of why I wanted to ask that question is because you've done so many things and so that idea of like whatever it is you intend to do that's that's the the core of defining success for you but you've had a way to weave all these different pieces together and I'm curious like when somebody meets you for the first time and you describe who you are and what you do how do you tell them?
Derek Sivers
Yeah usually I try to deflect the question. Usually I try to give a ambiguous little answer and spin it back on them because it's way more interesting to me if I can get somebody to talk about themselves. It's kind of a drag when I'm cornered into talking about myself. But if I had to, since you've cornered me right now, now I just say I'm an author. And when I say that, people say, "Author of what?" And I say, "Pop philosophy." So these days I'm writing books about pop philosophy and I guess that's who I am.
Tyler Waye
Okay But it was a journey to get to pop philosophy. I think it's the first I've heard those two words strung together. May be a whole genre I'm not reading, but when I hear and I know a bit about what you write so it feels like it's the right way to describe it. How did how did you get on to this path of pop philosophy? There's been all sorts of chapters before this chapter?
Derek Sivers
Yeah, not a journey not a path. It's a side effect of me sharing what I've learned. So for 15 years I was a professional musician, living in New York City, making my living playing on people's records, touring, selling my own records, running a recording studio, just doing whatever it takes to make a living as a musician in New York City. I did that for 15 years. I was inside the music industry, I was outside the music industry, and then I started sharing what I've learned. In fact, there's a cute story. I went back to Chicago, where I grew up, to visit a music group there. I was running CD Baby, my music distribution company. After 15 years of being a professional musician, I stopped by a music group meetup in Chicago and I told them I'd love to come visit. They said, "Oh great, we'd love for you to visit." I walked in, 10 minutes after it began, and I got a weird reception at the door. They said, "Oh my God, he's here, he's here. Okay, Derek, right this way, come over here." And they walked me through a hallway, opened a curtain, and I was standing on stage. And they said, "Ladies and gentlemen, Derek Sivers!" And people started clapping and then 50 people were staring at me. And I went, "Uh, what? I thought I was just here attending. Why are you all looking at me?" And they said, "Well, we thought you were going to speak." I said, "Oh, I thought I was just going to attend." They said, "Well, maybe you can tell us something." So I shared on stage for an hour and a half everything I had learned about the music industry to a bunch of my fellow musicians. And that was my first time I had ever really shared what I had learned in any public way. But after that frightening stage situation, I started writing down what I had learned. And I shared it with my musician clients later when I started my company, CD Baby. I started sharing what I had learned, and then after I sold the company, I shared what I had learned building and growing and selling a company. And after having a kid, I shared what I had learned with parenting and just being out in life and exploring, I shared what I had learned. So, after doing this for 20 years, I realized I had become an author.
Tyler Waye
And this part of it, CB Baby, you kind of just like put it into the story lightly, but you know, it's a big, big piece of the story. What was CD Baby?
Derek Sivers
Like I said, 15 years of being a professional musician. At one point after 13 years, I had an album's worth of material to share. So I recorded an album and tried to sell it online. But this was back in 1997. There was literally not a single business anywhere on the the internet that would sell my music. If you were Madonna or Miles Davis, yes, there were stores to sell your music, but if you were an independent person, there was not a single business anywhere online. So I made one, just for me. It wasn't meant to be for others. It was just, I built a thing to sell my music, which in 1997 was hard. It was so hard that after I did it, all my musician friends said, "Whoa, dude, can you sell my music through that thing?" And I went, "Yeah, all right, sure." As a favor to my friend Marco, and then a favor to my friend Rachael, and then a favor to my friend David. But then suddenly their friends started calling me, asking me to do it too. And after about 50 favors, I realized I had accidentally started a business.
Tyler Waye
And you know, it's interesting when you describe kind of like how your life has unfolded and you talk about, you know, you did this thing and then you started to tell your friends about it or kind of understand it and then over time you've kind of understood yourself to be an author at the end of this series of events and it sounds like you kind of fall into things but you also have this quality that feels like you're actually really intentionally living as well. What's the relationship that you found in your own history of falling into things versus this is actually quite intentional?
Derek Sivers
That's a really fun question. And I'd honestly never noticed that before. You're right. I definitely feel like Forrest Gump in many ways, that I've stumbled into some crazy and lucky things. But I have some life guidelines. Like if I'm going to do something, I want it to be utopian. I want it to be ideal.
Derek Sivers
Never just doing something for the money, for example. That's a life motto of mine. Never do anything for the money. Even if you need the money and you're doing something because it pays, well you need another reason to do it. It's never just for the money. It has to have some kind of learning, growing experience in it. Ideally then that the learning, growing experience is the main point and the money as a side effect.
Derek Sivers
So when I realized that I had accidentally started a business, I set out my mission that this business was going to live by. It's like, "Okay, well, I've accidentally started this thing, so as a musician, what would be my dream come true?" It's like, "Well, instead of getting paid once a year, like most distributors do it, I want to get paid every week. And I want to know the full name of everybody that buys my music." I had my four specific mission things but then same thing with life like I think it's important to keep challenging yourself and keep growing at any age.
Derek Sivers
After I sold my company I was living very happily on the beach in Santa Monica California loving my life and and realized that that comfort was going to lead to stagnation. So I forced myself to leave America. I renounced my US citizenship to prevent myself from going back. I forced myself to go live somewhere uncomfortable and do things I had never done before in the pursuit of constant growth. You see what I mean? So I guess I do some things intentionally like that where I set some guidelines or limits or rules for myself, that I'm pursuing things in a broader sense. I'm pursuing growth, I'm pursuing challenge, or I'm pursuing creating a utopia with this business I started. But then the details can be a surprise.
Tyler Waye
I came in wanting to ask you all these questions that I had pre-written, and I hope I'll get to some, But I almost feel like I just want to ask you other questions, too.
Tyler Waye
I asked you off the bat about like how do you define success? You talked about success in general for everyone like how would somebody define success? How have you defined it for yourself?
Derek Sivers
I set out to challenge myself to keep learning and growing So I think I've done that pretty well. I challenged myself to be comfortable outside of America because at that time I just described in Los Angeles, I felt like I was at the end of the rainbow. I was in Santa Monica, California This is the best place on earth. Oh my god. The weather is perfect. I love the people. I love the food. I love the weather. I love this place. Then I had to challenge myself to make other places feel just as much home as Los Angeles does. So that's when I challenged myself and I moved to Singapore and I stayed until it felt like home, and then I came to New Zealand and stayed until it felt like home and now I'm starting to spend more time in India and China which is like master class level. Can I feel at home in China? I really feel like, "Ah, this is my place, this is where all my friends are, this is this place that I feel most comfortable." That's a high challenge, so I keep doing this to myself, to challenge myself to feel at home in stranger and stranger places until they no longer feel strange. So that's a big one for me.
Derek Sivers
Being a good dad? Okay, I was gonna say great, yeah. Being a great dad. Being a great dad, I've done it. I'm doing it. That feels weird to say, but when people tell me I'm a great dad, I say, "Well, yeah, I know." It's like telling a weightlifter that they're buff. It's like, "Yeah, I know. I do the work." I spend 30 hours a week with my kid every week since he was born. I give him 30 hours a week of undivided attention. I'm a good dad. He tells me so every day. We have a great, great relationship. So that's been a success for me. There are other things that have not been a success. Romantic relationships, some health things. I don't know. It's not like I do everything right, but the two main things I set out to do, I'm happy that by my own measure are a success.
Tyler Waye
I mean as an aside when you bring up China, I lived in China for three years and so when you talk about feeling like home, you know if anyone were to ask for probably a decade straight where do you want to be dropped at any moment it was China. I just I continue to love it.
Derek Sivers
Wow! What part?
Tyler Waye
So we lived in outside of Shanghai for a year, a city called Suzhou and then we lived in Shanghai for a couple years.
Derek Sivers
What neighborhood in Shanghai?
Tyler Waye
Ah, Jiangshan Park.
Derek Sivers
Wow!
Tyler Waye
So, on the, yeah, Puxi side, like not the Pudong side, and pretty close to the French concession, if you're probably familiar with that.
Derek Sivers
That's my favorite neighborhood. I'm in the process, I'm laying the groundwork now of living in Shanghai in the future. I'm filling out the forms to become a legal resident and all of that stuff.
Tyler Waye
Derek, some of the highlights of my life have been in that city. And so when you talk about it, I would thoroughly cheer you on. Maybe one day we can drink a tea in Shanghai.
Derek Sivers
Yes. It would be a dream. Awesome. Have you over to my place.
Tyler Waye
Part of why I'm asking all these questions that are off the cuff is because it feels like you've done this thing that so many people want to trust that they could do, where it's like, what if I just followed the path of growth, or just followed this thing where it felt like I could trust that that would work out. And it has for you. I'm not saying it doesn't have its ups and its downs, but this way of operating, this philosophy of just following growth, seems like it's done well for you. How would somebody... Is it just trust? Is it something else? Like, if somebody else wanted to do that, and just lay caution to the wind, trust growth, does it work?
Derek Sivers
You have to have something of value to the world. You have to not just be confident, but have concrete skills that people are happy to pay for. I read a lot of books. I studied a lot of skills. I worked my ass off for 15 years to make myself valuable. I had a real hunger and scarcity drive at the beginning. Since I was a teenager, I set out into the world like, "I'm gonna be rich, I'm gonna be a success, I'm gonna be a successful musician, I'm gonna do this. I'm moving to New York City." If you can make it here, you can make it anywhere. Like, I really had this focused drive. You couldn't get me to hang out. You couldn't get me to get drunk. I never went to parties, never relaxed. I was a monomaniacal, focused motherfucker from the age of 16 until 30-something. Just like not a fun guy. I read hundreds of books, I built skills, I got good at making money and being a hustler. Like you could just drop me into any situation and I would find a way to make it work. So the confidence was grounded in that. So now I'm not quite as driven, but I know I've got a valuable set of skills and I know that I've also got a broad network now that I've earned over 30 years of doing this publicly. I put my first website online in 1994. I've been doing this a long time and so I've built up a lot of relationships that I can call on and built up a lot of skills and put out a lot of useful stuff into the world. So I think my confidence comes from that.
Tyler Waye
That's pretty interesting to hear. I haven't heard you talk much about that, that kind of drive time of your life, where it was about, you know, nose to grindstone or skill development or something was just like, I'm gonna make this happen, whatever, you know, achievement looks like I'm gonna go for it. And I don't know, and then probably putting some words in your mouth, but that drive, that grind that a lot of people could associate with. So for somebody who feels like they're drifting right now, do you have advice? Is it to trust growth? Is it skill development? Is it neither and just whatever feels right to the person? Like what would you guide for somebody?
Derek Sivers
Weird skill development. Not just skills, but unusual skills. So When I said I was nose to the grindstone 14 to 29 or so, I was entertaining crowds of thousands at pig shows in Vermont. I was running around in a black lycra bag, grabbing people's ankles in crowds and getting paid to bother people with a group I invented called the Professional Pests. I was producing people's albums in the heart of the music scene in New York City. I was playing on stage with a Japanese pop star. I was the guitarist for a Japanese pop star when I was 22 years old, and toured the world with him and got paid to do that. So I was building unusual skills, not just the skills of playing a video game or, I don't know, buying Facebook ads or something like that. You have to build skills that most people don't have. Go take a weird job. Don't take a normal job. Go find a weird job or go learn some weird skills and choose the life path that most people don't. Take the road less traveled. And by doing that repeatedly and deliberately building skills, like reading books when most people don't read books, when you hear that there's a trend against books, that should be your cue to take the opposite trend. Do what most people don't and work hard at it and you'll build unusual value.
Tyler Waye
There's the counter to that though. I mean there's a reason why most people don't do it and I don't know if it's fear or it's the path that leads to resistance. I love this idea of unusual skills or weird skills but a lot of people get scared and how have you been able to differentiate fear that's holding you back versus fear that's like I should actually be scared of that.
Derek Sivers
I only really honor physical safety fear. Like I'm not gonna jump off a building because it scares me but for almost everything else in life all your fears are in your head, they're self-identity, they're fears of what other people would think of you, they're fears of what you'll think of yourself. But you have the ability to change how you think so you can deliberately change how you think about any situation. I've had a motto since I was a teenager: "whatever scares you, go do it." The enemy is boredom, lethargy, feeling drained. That's what you should avoid. But fear should be something that you deliberately steer towards. When you notice something scares you, that's your compass. That this is something you should be doing. Because it's the growth choice, it's the self-discovery. It usually means the dark area of the map where you haven't been before, here be dragons, you steer towards these places in the name of growth and self-expansion. But also because you'll probably find that once you do the things that scare you, every single time once you do it you realize it wasn't scary. And pretty soon you just go through life following the fear becoming less and less scared and soon nothing scares you anymore.
Tyler Waye
Hence trying to make India and China feel more like home.
Derek Sivers
Yep.
Tyler Waye
Wow. Yeah right
Derek Sivers
Now it still terrifies me. I'm pursuing it because it terrifies me still. I'm 55. I have this background. I'm studying Chinese three hours a day with the goal of becoming fluent and moving to this place that terrifies me.
Tyler Waye
One of the things that stands out as you're describing how you're moving towards fear is just the conviction of choice. Like you're making a choice, you're making a difficult choice. It's not just you're going towards fear, like that's a bold choice. How, there's so many, there's almost that choice effect that people are feeling right now.
Tyler Waye
There's just so many things that we could do. Choice effect is where there's like you know there's four different jams on the grocery store shelf so it's like which jam do you pick it's how have you been able to make bold clear choices in a world that's so full of distractions?
Derek Sivers
At the core it's a deeper joy. There's the shallow joy of eating the ice cream and there's the deeper joy of being proud of yourself for not eating the ice cream. There's the shallow joy of swiping the screens and there's the deeper joy of the productivity and the creative output or even the learning that you get from spending zero time with distractions and being proud of yourself for resisting distractions. Being proud of yourself for not buying the thing that you're being enticed to buy or looking at the stupid bit of entertainment you're being enticed to look at. You could be proud of yourself. Ultimately I think that pride goes back to your first question about success. What does success look like to you? Success to me looks like doing the things I set out to do. And that's not going to happen if I let myself get distracted. I'm just so driven I just know that if I'm distracted that's enemy number one that will pull me away from what I set out to do so I look at all social media and Shallow entertainment as enemy #1.
Tyler Waye
There's this quote that I read of yours: If information was the answer, we'd all be billionaires with perfect abs. I loved that. I think you know we're full of this world of information right now, and and is it serving us?
Derek Sivers
In my new book called Useful Not True there's a chapter that I'm really proud of which is the metaphor of a computer that takes a while to process. And right now most people listening to this have had the experience where you go to a ChatGPT or something like that and you ask it one of those questions. It needs to think for a few minutes about right you you use the fancy o3 model or whatever it is you posting your query and it says thinking and It's churning all the information it's got. Now if partway through wou click stop and you give it a little more information, well now it's got to start all over again. So here's the point: You are like that, too. You've taken in a bunch of information in your life. At some point you need to run the query and do the output. You've already received plenty of input. You need to create the output now, but the catch is If you interrupt yourself with more input, well then you've got to start all over again. So the challenge to yourself is to at some point stop all inputs, say "I don't need any more information. I have received plenty. I've received more information in the last week than my ancestors received in their whole life. That's enough. I'm going to take what I've got right now, and do what I need to do." And do the output without receiving any more further inputs.
Tyler Waye
I think a lot of people just heard that and and heard that in a new way Derek Thanks for that.
Derek Sivers
Thank you. It's key. Again, I'm 55. I've been around. I only learned this for myself last year. I learned that if I stay in the mindset of thinking I need more information - if I need more inputs, then the output doesn't happen. It's only when I cut off the inputs that I'm finally able to create the output.
Tyler Waye
There's a aspect of what you've taught about or thought about or written about around simplicity or just minimalism or just kind of stripping away. So it feels like that's been a thought for you for a while, maybe not in these words. How how has that balance between minimalism versus something else been helpful for you?
Derek Sivers
Simplicity at its core is getting to the core. It's making that decision about what really matters and what doesn't matter as much. What's the fluff? What's key and what's not key? What's the foundation and what's the decoration? Making that distinction means making some bold decisions. Then you can decide if you want to keep the decoration anyway, because you like it. Like Paris, if you go to Paris and look around, oh my god, everything is so ornate. Whereas if you go to, I don't know, Poland, It's just got a different aesthetic to it. It's got a very core-only brutalism to it. Neither one is right or wrong you might decide that you want a life full of many fanciful things and that's your decision. But if you still need to know what's core just in case it really comes down to it. If there's a fire and you need to grab something and go, you need to know at all times what really matters to you, and what doesn't. Then for me I choose the brutalist aesthetic. I hardly own anything, and I love it that way, but that's my choice. I could also imagine a different life where five years from now I might be in a house with a thousand knickknacks. But I'll know that at any point I could just walk away from them, so I think First you just have to make that decision what really matters.
Tyler Waye
When I was looking into your background, I was curious what questions would feel like were just kind of coming to the surface for me as we started to talk. Because there's the entrepreneurship side of your successful background and there's the travel side and I'm fascinated by that. And then there's this kind of life leadership side and I think I'm just so drawn to that.
Derek Sivers
Actually, if you don't mind, before we changed that, I realized you just reminded me that I was speaking maybe a little too broadly about the simplicity minimalism thing. It applies to your business, it applies to your programming code, if you're programming, it applies to your writing, if you're communicating. At any point, whether you're sending an email, you have to know what's the real point here. And as we've all seen with people using AI prompts to turn one sentence they want to deliver, it turns it into four paragraphs and the person and receiving it turns those four paragraphs back into a sentence. You can skip all that by just communicating the core message only and leaving off the examples, the fluff, the manners. In your programming code, you can get to the core functionality, the version 0.1 of what's needed instead of trying to jump immediately to version 27 of your software. Get to the core of your business. There were so many times running my music distribution business that people would come to me and say, "Wow, you know, you've got this huge warehouse, you've got 85 employees, you know what else you could be doing? You could be selling porn, you could be selling movies, hey why don't you get into the streaming business? You could start a record label, you could do a radio station." And I'd say, "Yes, but I know what I'm doing here. I'm just doing this one thing. Also those other things might make money but they would dilute my energy and they would dilute the message of what we're doing here. And it's not about the money. Again, going back to your first question about success, I wasn't doing the company for the money so the profit was not a measure of success. The measure of success was setting out to make a musician's dream come true. Does selling porn or streaming movies make a musician's dream come true? No. So I kept it focused on the core. I made that decision early on what really matters here and what doesn't. It's the same with your writing, your programming, your business, your house, your hobbies, your life, the things you own. It all comes back to making that decision about what really matters and at least considering what would this look like if I stripped away everything that doesn't matter? Could it be more beautiful or more effective if it was just the core narrow focus?
Tyler Waye
Thanks for that. It speaks a little bit to one of the questions that was forming for me around this idea of going towards the fear because probably lots of times it works out and sometimes it ends up where you've done it And now you're not scared of it. But it just wasn't the right choice for you.
Tyler Waye
You needed to know what the core was to have that comparison. How did you figure out your core was it just something that like was that a journey of discovery or was that something you've always known?
Derek Sivers
I journal a lot. I reflect a lot. I pay attention to the small voice inside that is thrilled or irritable at certain paths. You can pay attention to the small voice that even if everybody says "You should turn right, go right, oh my god that's the best way, you're gonna to love it, it's amazing, we're here, it's great!" If you notice inside of you that turning that way, even for a few steps, is making you feel repulsed, but turning left is making you feel elated, then you turn left even though everybody's telling you otherwise. So that's the compass. Yeah, I just pay attention to that quiet compass.
Tyler Waye
And if we go back to the idea of the inputs versus just going, doing. For somebody who's listening to this and realizing, okay, this is new input and maybe the thing is just to go and do, right? Like it's the it's the funny reality of all this content that's meant to be about self-discovery and you're listening to it not necessarily doing the self-discovery but it can help right it can be the thing that guides you or starts you or pushes you what would be the start we talked about kind of weird skills is there something else that even come before that, that you would guide some reports?
Derek Sivers
I mean what comes before that is the value system that you have to place output over input or just decide if output matters more than input. One of my heroes is Tyler Cowen, who calls himself an "infovore." He also has wonderful output, but ultimately he takes in way more than he puts out, and that's his value. He decided that he's okay with that. He loves learning and taking in books and information. For me, I would prefer the opposite. I would love to write two books for every one book I read, in theory. It doesn't turn out that way, but that's what I'm aiming for. I'm aiming for output as my top priority. So maybe it's different for you. For anybody listening. No matter what you choose as your priority, somebody else is going to tell you that you're wrong. If you decide that safety and family is your top priority, somebody's going to tell you you're wrong. You should be more ambitious. You should go for the lack of safety. You should go for danger and challenge. And if you choose danger and challenge, somebody's going to tell you you're wrong. Comfort is where it's at. Why don't you just relax? You have to know what works for you, because there is no right or wrong answer. It's just what works for you. And when other people tell you that you're wrong, you have to just smile and know that they just have a different set of values.
Tyler Waye
And it sounds like that was part of kind of the core of CD Baby. Like when you're talking about CD Baby, you're talking about these, almost these rules that you'd set up for yourself. And part of it was, you know, what would you have wanted when you were an artist in that situation? Did it come down to a set of rules that really guided the growth of that business?
Derek Sivers
I started naming the four and I felt I was being boring. But those four rules were like the DNA of the company. Everything grew out of those four missions. Let me see if I can do it off the top of my head. #1 get paid every week, #2 never kicked out for not selling enough, #3 know the full information of everyone that buys my music, and #4 no paid placement allowed. So people with money were not allowed to buy higher visibility over people without money. That was it. And those four missions, those four guidelines shaped the whole company. And you could say there were some unwritten ones like whatever's best for the musicians is the right choice. That matters more than the profit. So many times if somebody wasn't happy, just give them all their money back. Or if we messed up or an order was lost, even if it wasn't our fault, even if somebody was scamming us, send it again at a loss. It's fine. Profit was not top priority. Making the musicians happy was top priority. I had enough money. I was fine. I was 100% owner. There were no investors. That helped a lot. There was nobody else but me that had a say in this. So I just made it my little utopian dream come true.
Tyler Waye
But you probably had to deal with tons of pressure. Like again, all the people saying, "But you could do this, or you could do it this way, You could grow faster if you just..." and you've been able to kind of like almost withstand pressure It feels like in terms of this is the normal path. This would be the normal thing to do This is what best practice would say but you've kind of like found your own utopia or your own. How do you hold off that pressure?
Derek Sivers
My kid turned me on to the cartoon Rick and Morty, okay, there's a great line in there where the scientist Rick that's his name. Yeah Somebody he's doing something in front of a crowd and everybody's going "Boo boo!" And he says "Your boos mean nothing to me! I've seen what makes you cheer!" Something like that, which is just like yeah, I know your values. I'm not impressed. I'm not trying to impress you people. So imagine you're a beautiful woman and everybody's telling you you should do porn. You're like "No! Absolutely not!" And if you're a man, everybody says, "Oh, you should be getting a job at a big company with a big salary." And you go, "No! There's no part of me that wants to do that. I do not want a job at a big company. That sounds like hell. I will not be tempted." People telling you you should be all over social media, people telling you that you should so on and so on. There's no end to the people that will be telling you what you should be doing. Usually you could just tell in yourself that that's not appealing to me, that's not who I want to be.
Tyler Waye
What would you say, Derek, is the lesson that's taking the longest to learn?
Derek Sivers
I probably haven't learned it yet. I don't know, I probably have some major flaw right now that somebody listening would be able to point out. So email me, tell me the flaws in my thinking, tell me what I've missed. I love putting myself into situations where I'm not the know-it-all. It's actually part of my fear of doing podcast interviews like this is that we've set up this dynamic right now as if I'm kind of up on stage with a podium full of answers. And that dynamic scares me because I lived in Los Angeles for a while and I knew a lot of famous people that get so full of themselves because everybody around them tells them that They're the best all the time, and they end up believing it. So that's a real thing to watch out for, for anybody listening to this, but especially me.
Tyler Waye
Thanks for that. It's an interesting dynamic, right? The point of this, I've been just peppering you with questions, right? Like, it's this one way. And I probably could add a bit more from my side from time to time, but I'm just actually really fascinated by this. But there's the other side of it, where now it's putting you in this position where advice, advice, advice.
Derek Sivers
It's efficient. It's the format too. You know what's funny? When I meet up with people in person, say like when I do go to a place like Bangalore or Shenzhen and I go meet up with people that have emailed me, almost every time people say, "Oh God, I'm sorry I'm talking so much about myself." I say, "No, this is what I want. You've already read my books, you've read my website, you've heard plenty of me. I'm here to just hear about you." So maybe it's just a different format. And different format gets a different dynamic. So this format of Derek Sivers as a guest on Tyler's Motiversity podcast, this kind of lays out the format. You're going to ask the questions and I'm going to give some succinct punchy answers.
Tyler Waye
And you brought up a couple times travel and it's a subject that I'm passionate about as well. What has travel meant for you? What has it brought to your life?
Derek Sivers
I only recently realized the real reason I'm traveling, which is to inhabit philosophies. I can read books about India, but only going there will let me inhabit this way of living. That's the main reason that I'll spend the thousands of dollars to fly all the way from New Zealand where I live now. And it's a 16 hour flight to get anywhere from here. It costs thousands of dollars even for the cheapest economy seat to get anywhere. So if I'm going to do that, it's because I really want to go inhabit the philosophy of a place. Not just read about it, but experience it and feel it and ideally adopt it.
Tyler Waye
One of the projects that was kind of the last big project I did before deciding to really dive into YouTube with our team and with my business partner was what I called working around the world. And so we lived in 12 different countries, one per month for a year, more than that, but that was kind of the formalized part. And it was really what you're talking about, to try to understand the philosophy of work in each of those countries. A month's not as much time as you would like, but to just sit and go slow and have as many conversations you can have people pull you into their world and and the way you described it I had never put it in words like that but that felt it resonated a lot.
Derek Sivers
We gotta pause on this for a second. When you said we was that like a business team or that was your family who who moved around for a year and a month at a time?
Tyler Waye
Yeah so my wife and I were the core but then we would have team members join us so we were filming it so we would have different groups who would help us you know whichever part of the project that they could do. So yeah, it was, we both, my wife and I share all of those memories and have lots to debrief and then there's a group that's kind of was connected to as well.
Derek Sivers
That's amazing. Okay. We have yet another thing in common. Oh, by the way, listeners, before we hit record, Tyler told me we have the same birthday. Tyler's only the third person I've met in my whole life that has the same birthday as me. That's kind of cool. So now we have this in common too.
Derek Sivers
So let's, okay, a little more context that you'll be able to relate to now. I told you I was living on the beach in Santa Monica feeling like it was the end of the rainbow and in fact my girlfriend at the time wanted to travel the world. And I said, "What? Why? We live in paradise! What are we going to do? Go to a different beach? It just doesn't get better than this. I have no desire to go anywhere else on earth. This is the best place on earth." you know that I value growth and so months later she and I broke up for other reasons but months later I noticed in myself that that attitude was going to hold me back and I read an interesting book called personal development for smart people by Steve Pavlina and deep inside on page 320 or something, he said, "If growth matters to you, you should organize your life so that you'll constantly be surprised, because you're not really learning unless you're surprised. If you're not surprised, things are just fitting in with what you already know about the world." He said, "So you can do this by reading books about subjects you know nothing about, or watching strange foreign films you ordinarily wouldn't watch." And then he said, "Ideally, you would move to a place that is as different as possible from where you grew up so that every day would be filled with surprises for you. And I read that a few months after breaking up with my girlfriend just as I was selling and leaving my company and feeling completely free. And that paragraph hit me at the right time. I said this is what I need to do. I'm going to force myself now to spend the rest of my life out. I've spent 40 years of my life in America. I'm going to spend the next 40 out and challenge myself to keep living in places that are as different as possible from what I know in the pursuit of growth. And so I set out this plan. That's why I jaw dropped when you said one month each. I set out this plan where I was going to keep going to places for my idea was three months each. Three months... actually I said three to twelve months, depends how long it takes, but a few months is as long as it takes to start to feel at home. You start to get your regular routines, you make friends, you really know the place, you've walked around the whole city, you know it, locals start to know you, you really start to feel that you belong here a bit and once you feel that feeling it's time to go to the next place and do it again. So I out this plan to do this in increasingly difficult places. I would start as easy as possible in London, because from America that's as easy as you get, then Sydney, then Berlin, then I would just keep going more and more difficult. The problem was, once I was in London, a girl I always had the hots for in San Francisco said that she wanted to be with me so I cancelled everything, went to San Francisco and accidentally retreated. So that's why I did the drastic step of renouncing my US citizenship to burn the ships, burn the bridges, make sure I could not retreat again. So there's the full context. It sounds like you and I had the same mission, same approach. It's really cool to hear.
Tyler Waye
Yeah, yeah, no, I mean it's amazing. I think when so many people hear about what you were just describing, this decision to go out into the world, some people don't come alive when they hear that. But there's a whole lot of people who come alive when they hear that. And I think that's why I kept asking these questions around, how did you make those bold choices? How did you handle the fear, and handle the pressure, and handle the normalcy of things that pull you back to doing things the way everyone else does it? I think that's what just stands out to me so much as I learn about your story. Yes, you've had success in all these areas. But I think people really, they want to learn that. And you've been so unique in your approach.
Derek Sivers
It's coming from some core ideas that I decide to extrapolate all the way, which by the way was not trying to pitch a book, but that was the subject of my last book called How to Live. It was 27 different ways you could approach life, and each one is taken to its logical conclusion. Where it's like, if independence is how to live, well then here's a life where independence is taken all the way. Ah, now if commitment is the way to live, here's what it looks like if you live a life of total commitment, where commitment is your highest value. Here's how to live. But wait, if creativity is your highest value, well then here's how to live. Here is the life of total creativity. Here's how you do it. And it's 27 chapters like that where each chapter disagrees with all the other chapters because each chapter thinks it has the answer. This is how to live. But it disagrees with the rest. That's life.
Derek Sivers
I've taken some core ideas like "whatever scares you, go do it." Or "live in a place that surprises you every day." And I've just taken these ideas to their logical conclusion and made it a challenge to myself. Maybe because this whole time I see life as short. Like this is it. I've only got a few decades here. I'm in the final quarter of my life maybe. This is it. There's an urgency around this. I want to live a really interesting full life. I want to have a lot of experiences so even if I mess up and it ends up being a huge mistake, well cool! That's part of an interesting symphony. It's to have some weird notes and some minor notes. It's not just a Bob Ross painting where everything is exactly what you'd expect or just a Mozart quartet where there's no big surprises. It should be a surprising symphony with some weird bits and some unusual turns and some strange chords. That's to me the full life. So I'm happy to go live some huge mistakes because it just adds to the richness of life.
Tyler Waye
You know an example of that as you're saying that I'm thinking to something I heard you talk about. I don't know where you are in the process right now but I I heard you talk about building your dream house and it's like it's just a rectangle and like no kitchen in it, no bathroom in it, maybe now, but when you were building it, like you were going to live in this thing before all the stuff that feels like normal house was in it. Can you describe this for me?
Derek Sivers
It's still being built. I'm going to go up tomorrow and it's about half an hour north of where I'm living now. It's up in a just a big piece of land, 10 hectares of cheap forest land off-grid that for nothing during COVID and put a 4 by 8 meter rectangle on it, well insulated rectangle, just a prefab cabin built in a refrigerator factory so it's super insulated. Yeah my boy and I we still just pee outside in the woods and I just bring a little portable burner up to make food and we go up there and we're just spending time there and deciding what we want to be there. So they're putting in... the shower works now. I took a shower there for the first time last week. There's an outdoor shower.
Tyler Waye
Will it ever be indoor? Because I heard that you were trying to almost live in it first to figure out like how do I want to live in it before I decide where things go.
Derek Sivers
Okay so maybe kind of like some of the other examples I've told you where I take an idea from a book and I go embody it, I read "How Buildings Learn" by Stuart Brand, which I highly, highly recommend. Anybody looking for an interesting new book to read, you have to go get the paper version. The Kindle version won't do. "How Buildings Learn" by Stuart Brand. It's my most gifted book. It's so fascinating. He talks about how buildings rot from water out. So water is always the reason for any building decay. So reading that I thought, well then, shouldn't we just keep all the water things outside? To just keep the enclosed shelter part where we spend most of our waking hours, keep that away from the water. If you need to go to the bathroom, that's just a few minutes a day. You can be a little chilly, step outside, keep that outside. Same with the shower, you're taking a hot shower, let all that steam go out into the air instead of keeping it trapped inside your insulated dwelling. So I'm just following on some ideas that I've heard that I just wanted to try living.
Tyler Waye
I mean all of it sounds perfect when you're in New Zealand. We're in somewhat northern Canada so I can feel it.
Derek Sivers
Where I'm living in New Zealand, it's cold nine months per year. So most people, when I tell them of this plan, they say, "What, you crazy?" I'm like, "Well, look, even if I'm shivering for two minutes in the bathroom, ultimately it's worth it to me because it'll make the house last longer, keeps the moisture out, keeps the air of the house healthier by not mixing in the moisture. It's worth it to me to be uncomfortable for two minutes in the name of other methods.
Tyler Waye
You've, again I'm going to project a little bit here, but you've lived objectively a successful life and it sounds like subjectively a successful life, really clear to what's core to you. And a lot of young people who watch our content are trying to be the same. What advice would you offer a 20-year-old nowadays who's got so much coming at them? What would you tell somebody at that age?
Derek Sivers
Go do the opposite of everybody else, like we talked about earlier. Build weird skills. Make weird choices. I feel bad for the people that email me that say, "I don't know what I want. I don't know what to do. I'm just adrift." And they tell me they've just done nothing unusual in their whole life. They just went to high school, did the normal stuff, they went to college, majored in communication, they got some dumb job. They've never done anything weird to set themselves apart or never pursued a strange path. And so think of a little toy boat in a creek or a pond that's just adrift. The way to make it reach ashore anywhere s to just give it a tap, push it some strange direction, just break out of its normal, habitual pattern it's in, where it's not getting anywhere. Doing anything. Go make mistakes. Damn, especially if you're 20, making mistakes is the fountain of youth. You should be deliberately pursuing mistakes. Go do the stupidest thing you can imagine. Take the weirdest job at an oil rig in Kazakhstan and go be a horse trainer or train as a sewage cleaning plant. Just making any weird decisions will push you out of this feeling of adrift and give you a different insight in life that will end up being your competitive advantage. Especially when you're young, doing the weirdest, stupidest things is the right thing to do. Go out into the world and go into that strange dark alley and go talk to that scary person. These are the scary choices in the moment, but will end up being your advantage long run.
Tyler Waye
I could just see the parents trying to hit mute as you were saying that, you know, because it's so counter to what we're guided to do.
Derek Sivers
And that's the point! It's counter. Maybe I'm coming at this from a musician's point of view, where if everybody writing a song says, "Baby, I look in your eyes and I realize the way I feel, it's so real." Okay, there's no need to say that ever again. It's been said those are the stupidest choices you could ever make because they are completely expected. That's what hundreds of songs have said before. So no, you want to, as a songwriter then, choose, you know, "Baby, when I look in your eyes, it makes me want to grab a fire poker." You want to say the thing that jars people's ears to say, "Wait, what did he just say? That's not what I expected." So same thing with your life. If other people are being social media managers and doing this and buying advertisements and getting a good job and following this, there's no need for you to do that. It's been done. Enough people are doing it. You don't have to do that. There are enough people doing that. This is your imperative. This is your challenge to do the opposite. To do what nobody else is doing because the other stuff has been done.
Tyler Waye
You've gone towards fear. You've gone towards choice. You've gone towards change. But you've also talked about coming back to this core. And I'm curious if you have any daily rituals or routines that are part of your core, no matter where you live in the world?
Derek Sivers
No. Maybe just journaling. I write a lot because at the age of 42, I found myself wondering what my 20s were like and I had no real record. I just had really faint memories and I couldn't tell how accurate they were. And I kicked myself wishing I would have just spent five minutes a day to keep a damn diary in my twenties. Even just woke up, ate this, did this, met with this person, did this, went to sleep. That would be so precious to me thirty years later to read what I was doing and thinking when I was 21, when I was 23, when I was 29. Oh my god, I wish I had some record of that. But just a few pictures are not a real record. They don't tell you what you were really feeling. Our memories are so faulty. It really helps so much to have a journal that you wrote that day for nobody but yourself so it's completely honest. So realizing that at 42, you know, the best time to plant a tree was 20 years ago. The next best time is now. So at the age of 42 I started keeping an every single day journal that I never miss. Or if I miss a day then I do it the next morning. That's so important. It's where I organize my thoughts. First I just log the day and I organize my thoughts, share for my future self how I'm really feeling. That's come in really, really handy when I look back at times in my life when I made certain choices and now a decade later I want to look back and see how did I really feel when I made that choice. And my diary is the only honest, accurate log of that. It's one of the only things I think everybody should do. Everybody should journal. That's not conditional. That's unconditional. Everyone, every human, should be journaling, whether that's into a voice recorder or into a paper diary or into a text file on your computer or something. Find a way to keep a permanent record of your daily life, even the boring mundane stuff, for just a few minutes. Ideally just say what you did and how you're feeling, but you can also use this then as a place to reflect because real learning doesn't happen when you take in information. Real learning is what happens when you reflect for yourself on the information you've taken in and writing in your journal is really the best time to do that.
Tyler Waye
I hope, I think, actually, I think a lot of people just heard that pretty deeply. And, you know, when you're talking about your 20s and just kind of not remembering what that decade was, you know, in general, but not the feelings. I mentioned that I lived in China. I was, you know, we moved in when I was 26 and it was the same thing. What was the country that scared us the most? We had six countries we could move to. We chose China because it scared us the most. And I remember before that, I was 26, and I'd been really good at being really good at what other people had asked me to do. I'd just been able to do that. But it wasn't the life that was right for me. And it was success that looked like a scoreboard. It looked like whatever could climb the fastest or the biggest number. And that movement towards fear was what really caused me to look at life differently, build it differently, think of it differently, aim at different things. And when you're talking about journaling and that flip of the moment where it goes from you're just living this thing and you're not really recording it or you're not even necessarily aware of how it's unfolding to the thing that allows you to start to look at yourself in the mirror, I think that's such a fantastic opportunity for people. And I was just struck as you were describing that, kind of thinking back on my own journey. Thanks for that.
Derek Sivers
Especially those adventurous times in your life when you can tell that you've got a lot going on. That's when it's even more important to take a few minutes before bed and write it down. 'Cause your future self will find it very interesting and useful. You're doing it all for your future self. Everything I'm writing in my journal is somewhat for my present self, but even more so for my future self. And I do go back and revisit them at some key times, and I've made some massive life choices based on the accurate daily reporting of my past journals.
Tyler Waye
Wow. And you've talked about being a dad, you've talked about prioritizing growth, you've talked about writing books, what do you hope your legacy is, Derek?
Derek Sivers
Oh, I don't care one bit. I hope my kid lives a fulfilling life, but how people remember me doesn't matter at all. In fact, I would assume that if they don't remember me, it's because their own lives are more interesting. So in a way, I don't care to be remembered. I would like to create useful ideas that people can still glean in the future, but maybe that's second hand and you don't even need to give me credit. If somebody listening to this takes everything I've said right now and goes and publishes a hit book from it and doesn't give me any credit I would be so happy. Go take it. I don't need any more credit myself.
Tyler Waye
Wow. And yet you've had this extraordinary series of things you've been able to do. And for those who want to stay plugged in, stay connected to the projects you've got coming up, what's next and where can they go?
Derek Sivers
I don't know what's next and that's why they should go to my website. I'm not really on social media. I just don't like it. That's one of those examples where people say I should, but I'm like, "Nah, I just don't like it." It's like TV to me. I never liked TV with all the flashing ads and the quick cuts. I never liked it. So, not on social media. Go to my website, sive.rs and Tyler will tell you I answer every single email. So anybody listening to this, go email me, say hello, ask me anything at all, or just introduce yourself. I actually spend an hour a day just answering email and I love that hour of the day so say hello.
Tyler Waye
Wow, amazing. And we'll make sure that everyone gets that link and I just want to say thank you for this fantastic and really genuine conversation that I've learned so much from Derek, thank you.
Derek Sivers
Of course, yeah, it's fun questions and it sounds like you and I have so much in common that we need to, as you say, meet up in Shanghai.