Chelsea Riffe
host: Chelsea Riffe
time zones, travel experiences, parenting, digital independence, online privacy, writing style, self-expression
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Transcript:
Chelsea
Derek Sivers, welcome to In my non-expert opinion”, how are you today?
Derek Sivers
Great. Thanks. And for a little context, it is seven in the morning here in New Zealand. Where are you and what time is it?
Chelsea
I’m in Cape Town, South Africa, and it’s 9 p.m. So we are completely different time zones. I actually told my friend I am almost ready for bed, but I have an interview with someone that I wanted to interview for like two years. I need to get it together. And she’s like, “Put on this playlist, drink water with electrolytes, shake and dance around.” And I was like, that’s a great idea. So I did a little bit of that. So I’m ready for our interview.
Derek Sivers
Well, thanks for accommodating the times.
Chelsea
I actually wanted to kick off with that because I know you are someone who has lived in multiple places. I think you lived in England for a little bit. You’re tuning in from New Zealand. You’ve traveled all over. But something you were telling me off air is that you’re actually not nomadic, but it feels like you are. So can you explain your your journey around the world and how you ended up in New Zealand?
Derek Sivers
Well. I am deeply nomadic in my heart and my values and my beliefs. But right after my kid was born. No, wait. I’m going to go back and tell this in sequential order. I grew up in America for the most part. When I was five years old we lived in England for a year. Where did you grow up, by the way?
Chelsea
In Central Florida. Right where the space stuff is. Where all the rockets take off.
Derek Sivers
Gotcha. Okay. So I spent most of my life in America, and there was even a moment when I was 36 years old and my girlfriend wanted to travel the world, but we were living on the beach in Santa Monica, California. I was happy as could be. And she said she wanted to travel. And I said, “What? Why? Like we’re in Paradise. Why would I go anywhere else? What am I going to do, go to a different beach? No. Like we’ve arrived. This is the best place in the whole world.” And I really believed that. But I was reading a book called “Personal Development for Smart People” by Steve Pavlina, which is a fascinating book, and it introduced the idea into my brain that if you want to keep learning and growing, you need to keep surprising yourself. And you could do that by reading books and taking information that’s outside of your usual realm. But maybe the most effective way to do it is to move somewhere that’s very different from where you grew up, where every day you’re going to be surprised. Your cultural expectations, just norms and standards will be challenged and it’ll keep your brain open to new ideas and expanding. And I read this and I went, “Ooh, that’s a really good point.” But then it wasn’t until about six months later when I broke up with the girlfriend. I was living in Portland. My business was running itself. And then I thought, you know, I could live around the whole world. And in fact, I really, really want to do that.
Derek Sivers
Like, I actually want to move to a new country every six months, which I think from my experience, even just moving around America is long enough for a place to start to feel like home. You know, you start to get it. You have your local routines, you get some friends there. It starts to feel like, yeah, I know this place. I’ve lived here and then after six months, might even be up to two years after a place really feels comfortable. Then you move to a new place and do that again, and then eventually the dream. The goal is for the whole world to feel like home. Like, how badass would that be? If by the end of my life, I could spin the globe and every little part of it feels like home to me? So that’s the mission I set out on. And as I was leaving America, I passed through New York City and I met this gorgeous girl, and we went on two dates. And at the end of the second date, I liked her. So I said, “Hey, I’m leaving America and never coming back, so we should not have a third date unless you also want to do the same thing.” And she said, “Oh hell yeah, get me out of here.” So that’s why we had a third date and that’s why she left with me eight months later. Yeah, I stayed in New York an extra eight months, mostly just see old friends and into date her a little longer. Then eight months later, I was like, come on, let’s get out of here.
Derek Sivers
So as soon as we left America, it turns out that for her, there was a difference between in theory and in practice. So I already knew that I really wanted to live outside America. She thought she did. But once we left America, she hated it. She said, “Oh, I don’t like traveling at all. I just want to stay put in one place.” So we tried staying put in Singapore. It seemed like a good place where I could learn Chinese, but yet in an English speaking place. And it was clean and safe. But all in all, I just wanted to keep being nomadic, and she didn’t. So we broke up. But as soon as we broke up, she found out she was pregnant. So we got back together, and we have a kid who I love who’s 12 years old now. But yeah, at that moment, when she found out she was pregnant, I had a values choice to make. Which was is it more important to me to travel, or more important to me to be a good dad? Because I could just go say, “No, this is what I’m doing. I’m traveling, this is my mission.” And I could be a bad dad and not be there for my kid or vice versa. So I chose the vice versa. Traveling and living all around the world, not even traveling. Living all around the world matters to me a lot, a lot, a lot, a lot. But my kid matters to me more. So there we are.
Chelsea
And how did you end up in New Zealand?
Derek Sivers
Oh, my boy was born in Singapore and we lived there for six months, thinking that we were going to live there for the whole 18 years of his childhood. We actually did all the paperwork and became legal permanent residents. But after he was about six, eight, nine months old, I saw that Singapore has most things you need in life, but it lacks some nature. And I thought, you know, I really want my kid to grow up in nature, you know, feet in the river, hands in the mud. Climbing trees, long grass blowing in the wind. You know, like I think it’s an important part of childhood to be connected to the natural world, not just screens. So I thought, well, ideally he’d grow up in New Zealand because that’s like nature Paradise. So I thought, well, let’s see, what does it take? You know, tick tick tick. Looked it up. All right. Fill out some forms. Tick tick tick. And it was nine months of paperwork. And I became a legal resident of New Zealand. And here we are still. It’s a great, great, great place to be a kid.
Chelsea
Oh, my gosh, I am so jealous of your son for getting to be raised in New Zealand. And did he learn a language by living in Singapore too?
Derek Sivers
No. We left when he was nine months old.
Chelsea
Okay, so he did not. He was not a savant learning at nine months old.
Derek Sivers
No. He’s entirely grown up here, and it’s definitely affected his childhood. He is a nature boy. Well, okay. Not just his childhood. I’m sorry. Let me clarify. Somebody could grow up in New Zealand staring at a screen. And a lot of his friends have, you know, their grandparents and parents are from here. They take it for granted. They grow up on their PlayStation or iPad or whatever. But because I had moved here from Singapore with this mission, I made a point of keeping him outside for most of his childhood. So as soon as he’d wake up at six in the morning or whatever, we’d go straight outside. Even if it was cold and rainy, we’d just bring the raincoat and we’d go outside and play in the forest, or go out to the beach at 7 a.m. or whatever, and we’d play outside like that, making little handmade boats to sail down the creek or, you know, making castles out of driftwood on the beach. He’s grown up like that. And so he’s actually really disappointed when his friends want to play PlayStation because he’s like, “Come on, let’s go outside and play.” So I really like that he’s grown up outside like that. But I guess that wasn’t just the environment. That was definitely my influence.
Chelsea
Yeah. Did you grow up like that, or did you feel like I didn’t have that so I want to give that to my son?
Derek Sivers
Neither. I had a little bit of it, but I just felt that those were the best parts of being a kid. Were, you know, splashing in a creek looking for tadpoles, things like that, you know?
Chelsea
Yeah. The catching the minnows and, you know, hiding weird animals in your house and, why do we have a lizard.
Derek Sivers
Running down hills so fast it feels like you’re going to fall over. You know, all those things I like about being a kid out in the natural world, I think are so wonderful. And and also more and more rare as screens get more and more addictive.
Chelsea
Yeah. I mean, as we’re talking about it, we’re on a screen. Your business was online. You grew up in an, you know, a digital world.
Derek Sivers
Oh, wait. Sorry to interrupt you. I didn’t grow up in a digital world. I’m actually really thankful I’m 54 years old now that, like, the internet didn’t happen until I was 26. Like, I spent the first 25 years of my life offline. And I’m really, really thankful for that. I really have had some of the best years of my life without any internet, so it always to me, keeps it in perspective. You know, when people have these always online lives or even when they use cloud tools, I’m like, “No, no, no, no.” I don’t want to need the internet in order to create or in order to have access to everything I’ve written. I’m not going to keep that on the internet. That would mean that I’d be kind of cursed to be required and bound to be on the internet at all times. Fuck that. No. So anyway.
Chelsea
Yeah, I also grew up without a laptop or computer or anything until I was maybe in middle school, and my sister is nine years younger than me, and she grew up with everything, all the digital devices. And I’m like, it’s weird because we’re only nine years apart, but we had such a different childhood and middle school experience, and you can tell how different it is from her learning style to her own socialization and how she makes friends. And I think not only not having that when I grew up, but then traveling allowed me to make friends and develop those social skills. And I’m curious for you now living in New Zealand. I know you also said in a few years when your son turns 18, you do want to be nomadic, but you told me your partner doesn’t like traveling. Um, and so I’m curious, has that changed? Are you like, I’m peacing out? I’m ready to see the world. Like, what is the game plan?
Derek Sivers
No. Like I said, we broke up before he was born.
Chelsea
Okay, okay.
Derek Sivers
She is his mother and my ex. But partner or not, no matter who I am with or not, I need to do this. I have been yearning to do this, and I set out on a mission to do this. I have paused that mission for 18 years to be a good dad. But somewhere around the age of 18, whenever he’s ready to go out into the world on his own, you know, it’s super important to me to go live around the world. In fact, I figured out a nice two word phrase to describe why I travel is I want to inhabit philosophies.
Chelsea
Ooh.
Derek Sivers
I really---
Chelsea
That’s a good one.
Derek Sivers
Thank you. I really like how the Brazilian approach to life is very different than the Finnish approach to life, which is very different than the Chinese approach to life. And these are all valid philosophies, which is kind of what my last book called, “How to Live” was about. Is that there are completely valid philosophies that are completely contradicting, and they all exist at the same time, and none of them is right or wrong. And I think countries or cultures we could say it doesn’t always happen at the country border. Cultures are a great way of inhabiting philosophies. And so I want to actually go live in these places, live as a local. Have local friends to understand the local mindset and worldview. That’s really the reason I travel.
Chelsea
Have you read The Midnight Library by Matthew Haig?
Derek Sivers
Never heard of it. No.
Chelsea
Oh, you have to read it. It’s a fictional story, but it’s about a girl named Nora who there’s this midnight library, and every time she goes, she gets to try on a new life out of a book. So she’s a rock star in Brazil. Then she’s an Olympian swimmer, then she’s a mom, then she’s an accountant, and she lives all over the world. She tries on all these different occupations. And I remember hearing so much about it, and I was like, this sounds so fun to read. It sounds kind of like my lifestyle. I’m kind of always wearing these different hats, and someone said, “I had to stop reading it because it was really depressing.” And I was like, “What do you mean it was depressing? It sounds like the best book ever.” And they were saying, because each life of hers didn’t work out. And so she kept going back to the library. Spoiler alert here, everybody. Don’t listen unless you’ve listened to this book yet. But the lives keep not working in the way she thought. She keeps thinking, “If I’m a rock star in Brazil, I will be the happiest person alive. When I’m an Olympian swimmer. I will finally get recognition from my dad.” So she keeps, you know, trying on these lives. And it’s not ending with the happily ever after. And it’s so funny how much we want happily ever ending stories. And sometimes it’s like, no matter what life you try on, no matter where, no matter what location, there are always going to be downsides. And what you were telling me just reminded me so much of living, like the real version of the Midnight Library.
Derek Sivers
Nice. You know, different girlfriend. Actually, the one that I was living with on the beach in Santa Monica. We had a six and a half year long relationship that was wonderful. It was a great relationship for both of us. It was just wonderful all the way throughout. In fact, we got along so well that in six and a half years we had only one fight and it lasted about five minutes. And it’s about whose turn it was to clean the bathroom. That was it, six and a half years of just happiness. And there was just this moment, after six and a half years where I was working on my business up in Portland, Oregon. She had a big circle of friends down in Los Angeles. We just realized our lives were going separate ways. So one day on a Saturday, after seeing a movie, we just turned to each other basically at the same time and said, “Do you want to break up?” And we’re like, “Yeah, do you? Yeah, I think it’s time. All right. Wow. I think we just broke up. All right. You want to go get a lemonade?” And that’s it. I never saw her again. And it was a great six and a half years. And I remember somebody later when I was telling them about this relationship, said, “It’s a shame it didn’t work out.” And I said, “The fuck it didn’t. It did work out. That was great. Oh, do you mean the ending? Like, as if every good thing has to go on forever? No, of course not. That was a great relationship that lasted six and a half years. It was wonderful.” It’s not like, “Oh, I’m sorry that movie didn’t work out because it ended.” No, the movie was two hours long. It was great. The relationship was six and a half years long. It was great.
Chelsea
I also remember hearing a story about a movie screen test they were doing, and they showed. I think it was the one with Jennifer Aniston and Vince Vaughn called like “The Break-Up” or something. And they tried an ending where they actually didn’t get back together. They just stayed broken up. They ran into each other at a baseball game and they’re like, “Hey, nice to see you.” And kind of go their separate ways. And then they tried another ending where they run into each other at the baseball game. They see each other and they rekindle their relationship and they get back together. And people hated the one where they just broke up and kept going their separate ways because they wanted that happily ever after ending again. And it shows even again in all these fictional stories. It’s so hard, like you said, to grasp the concept of like, all good things can come to an end. It doesn’t need to be eternal, forever bound, you know, legally on paperwork, like some things run their course and they were meant to serve a purpose. And I feel like your example of this six year relationship, six and a half years, is such a good testament of that.
Derek Sivers
Thanks. A friend. When I was thinking of moving to India long ago, like 15 years ago, I was on the verge of moving to India and I asked a friend, “Can you think of any reason why I shouldn’t?” And she said, “Yeah, don’t do it if you think it’ll make you happy.” I went, “Oh that’s good.” And so what was the book called? Midnight stories?
Chelsea
Midnight library.
Derek Sivers
Midnight library. It sounds like the only problem was the girl had expectations that doing this was going to make her happy. Where instead, it’s like, oh, my God, you got to be a rock star in Brazil. That’s amazing. Like, so what if it didn’t, like, have some outcome? The only problem is, if you go in expecting that it’s going to change your life. If some external thing is going to change your internal thing, that’s the problem. But oh my God, you got to go have this experience. I think there could be a sub lesson in there about expectations.
Chelsea
Yeah. And I think that was it. I think it was two that no matter what life you try on, it was almost every life. Even when she had these big major accomplishments, there was always something happening in the world or her family, like her dad was an alcoholic in one of them. And then another one, the guy that was her ex. He ends up being actually a cheating ex in this storyline. And you know, there’s always something and it’s trying to tell you, like, no matter what these expectations are, life is messy, people are complicated. And it’s never going to be like the storybook that you think it is in your head.
Derek Sivers
Nice.
Chelsea
There’s also, what were you just saying about moving to India and being happy? I remember I was going through a really rough time in probably like 2016, 2017. Just didn’t like my job, didn’t like my lifestyle, and I was just ready to start over and be like, I’m going to move to London and start a new life. And I was going to therapy and I told my therapist I was like, “I’m interviewing at companies in London, I visited there. I’m already looking up like neighborhoods to live in.” And then she kind of just stopped me and she was like, “You know, wherever you go, your brain comes with you, like you’re not going to get off the plane and you’re going to have a different brain, you’re going to be in a different location, but you’re going to have the same brain, the same body, the same thoughts.” So, you know, yes, there is something about a cultural shift that you will maybe be influenced by, “Oh, wow, the culture is different. I want to be more like them. And I’m interested in, you know, going to the Sunday roast and having a laugh at the pub and that could change my mental state.” But her point was like, no matter where you go, there you are type of thing. And I’m just curious your viewpoint on that.
Derek Sivers
Oh, I’ve got one. Shit like that can be said to defend anything. Every action you could consider has a valid argument for and against it, and they can even be vapid sayings like wherever you go, there you are. Yeah. Duh. So think instead how ridiculous it would be if you lived in a three bedroom house with a kitchen and a living room and maybe a separate room, like a study or a dining room. And let’s say you’re sitting in the dining room and you say, “Let’s go sit in the living room.” And somebody says, “No, Chelsea, wherever you go, there you are. So don’t go to the other room. Just stay right here.” It’s like, well, no, there’s a living room right there. I feel like sitting in it, “No, no. What are you running away from?” It’s like, “No, I’m not running away. Just come on. It’s right there. Let’s go.” To me, the world is like our house, and China is our living room, and the U.S. is our dining room and India is our study and this is your world. Like, why are you just staying in one room of it? It’s the whole place is yours. You can go. It’s all yours. What are you doing sitting in one room or one floor? So, of course, anybody could hear me saying that and say, “Well, that’s bullshit.” And I’d say, yeah, I agree, but this is the bullshit that supports the mindset that I like having. So there’s always bullshit to support whatever point you want to defend. We rationalize, we pick an emotional stance on something for whatever reasons, and then we can find any bullshit to support it. Sorry that’s what my next book is about. It’s called “Useful Not True”. And it’s about how we choose beliefs because they’re useful to us, not because they’re absolutely true.
Chelsea
I was going to say I listened to a little bit of it, and I was like, this is why I love your work. Your work has always influenced me. I was actually making notes today, and I was like, I actually didn’t realize how much of your work is reflected in my work. Like my “About Me” page was inspired by you. I wrote a post on my Instagram about like “Welcome to My Utopia”. And that was from your book. I think “Anything You Want”, like your business, can be your utopia. And I wrote an email about my utopia, and that was like the most responded email I’ve ever gotten. People were like, “I love this email. Like this so inspiring.” I remember you said something about how when you send customers, a package. I don’t know, I just remember something about, like, “I hope it landed to you like a feather in a box. “Like there was some really specific copy. And I remember being like, “Yeah, why can’t my welcome email to my course instead of like, hey, welcome to the course. Here’s the course link. See you Tuesday.” I try to make it more vivid and and model it after what your feather landing in a box or a pillow. You know what I’m talking about. I’m butchering this. But I’ve always really appreciated your viewpoint, and I listened to a little bit of “Useful Not True”. And I was thinking how I think a lot of viewpoints come from a place of self-defense or protection.
Derek Sivers
Yes.
Chelsea
Like going back to that London example. I remember telling my mom, like, I’m going to London, I’m moving and when I want to do something, I will move, you know, Heaven and Earth to do it.
Chelsea
So for me, like London was in the bag, I’m going. My mom, who has always been my biggest supporter, kept pushing back like, “Why London and why now? And isn’t it expensive?” And da da da da da. And eventually I was like, why are you pushing back so much on this? I feel like I’ve done a lot of crazier things. I don’t even think this is that crazy. And you’re pushing back. And eventually, she explained, “I’m just worried that if things don’t work out the way you want them to, that financially you’re going to be in a bind and then you’re going to have to ask us for money. And I don’t have a job, and your dad is out of work right now. And if we can’t offer you money, then I’m afraid you’re gonna have to do something you don’t want to.” Like it basically spiraled into this thing that I might end up being homeless on the streets in London, begging for money if I didn’t really think this through. So once I heard that I actually had so much more empathy for my mom to be like, this isn’t coming from a place of, “You’re dumb, you can’t make London happen.” It was more of like, “I’m scared if you need our help, we’re not going to be able to be parents and help you, and we’re going to kind of fail you.” And it reminded me of the Useful Not True of like, yeah, that was useful to think through the options, but it wasn’t true. And it didn’t actually apply to my situation. Like it wasn’t like, “Oh, I have to do that because my mom said so.”
Derek Sivers
Wow, that’s a great example. Thank you.
Chelsea
Yeah. I’m curious, “Useful Not True” reminds me of... I keep having this conversation with everybody, astrology. I actually like astrology because to me, it’s a meaning making system. I know people will argue and be like, “Oh, well, did you know science says it’s not real? And I come from a medical background...” And we will go in circles and I’m like, I’m not comparing science to astrology and saying if my arm breaks, I hope that the energy of Mars is going to fix it. I don’t believe that. It’s a meaning making system that helps validate some of my feelings or emotions where I’m like, “Oh, the moon is in cancer and I’m a little more emotional today.” And it helps my point of view. I’m curious like what are some of the things you just kind of said when we were like, “Yeah, it’s like not really mainstream. It might be a little bit bullshit, but it helps me. It’s useful for me, even if it’s not scientifically or like, you know, evidence based true.”
Derek Sivers
Oh, I mean, astrology, that’s a fun example. That you can say, “Yeah, I know it’s not real, but I find it fun or I like what it sparks in me, or it gives me any kind of reason to say, ‘Man, I’m so tired, I have no energy today.’” And to say, “Oh, it’s because of Jupiter. Whatever.” Even if you know that’s not true, it’s like, why not? If that makes you feel a little more magic in life or just kind of takes some of the burden off yourself, it’s fun to know why you like it. So I’ll give a tiny example that’s just super current. So anybody listening to this interview far in the future, don’t hold me to this. Quick aside, once in 2015, for one week, I was learning about the history of hip hop, and that was the week that Tim Ferriss called me to do an interview. So we talked and I said, “I’m listening to the history of hip hop.” And for years afterwards, people were just like sending me all this information about hip hop. I was like, “No, sorry, that was just one week in my life.” Okay. So anyway, in this week of my life, where are we? Mid-may 2024, I’m thinking of setting up a company in China because I will probably never be a legal resident of China, but I like having skin in the game. I like that if I’ve got some legal tie to a place or some legal kind of in, there’s kind of a better word I could use there. I don’t know what it would be, a stake in it. That it helps me feel connected to a place. So right now, I’m a citizen of India because my kid’s mother was from India.
Derek Sivers
She was born there. And so through our connection, me and my kid are both citizens of India through her. So this place that I would otherwise not have much of a connection to, now I do. India feels like partially my country, even though I’ve only spent a few weeks there. I’ve got this tie there. I’ve got the legal right to live there. I’m a citizen. I will never be a citizen of China and maybe never even be a legal resident. But setting up a company there gives you access to a bank account, a WeChat account, and most importantly, just kind of put skin in the game. It makes me feel connected there. Same thing when I did the paperwork years ago and became an e-resident of Estonia. And for a little while I was a legal resident of Belgium and Portugal. I was trying to get an EU passport at the time, even though these things were all just little bits of technicalities. It made me feel connected to a place. Before doing the paperwork and becoming a legal resident of Belgium, I had no connection to Belgium. Belgium was just some country like, I don’t know, like Uruguay or Myanmar or any other country on earth that I had no connection to. But just through a little bit of paperwork now I feel a connection to it. It’s like, this is my country. So I know that’s no more true than, you know, the moon rising over Saturn or something. But it works for me. It helps me feel connected to a place. So I am irrationally considering setting up a company in China for this reason.
Derek Sivers
I’m thinking of incorporating a company. It’s called WFOE. I think Wholly Foreign Owned Enterprise. As, like how a foreigner can have a company in China. Oh, I almost made that slip again. How a foreigner can have a company in China. Yes.
Chelsea
That to me speaks a lot to again the energetics and your creating the environments and the conditions to feel what you want to feel. Like you said, I am going to do the paperwork. I’m going to take the steps. This is going to be an effort to make me feel more energetically tied to China, to India, etc. Where, yeah, someone like me, I’m living in Cape Town now. I’m on a tourist visa. I don’t own a lease. I don’t have an apartment, I don’t have a car. I really have nothing. They could kick me out tomorrow. But I feel so at peace here and so at home that I don’t feel the need to go and try to get a residence visa or artist visa or whatever. And so I love this point that we’re making is like, we’re both travelers and we both love to connect to the places we’re in, but we have different viewpoints of what it means to actually be like energetically tied to them.
Derek Sivers
Well, yes but no. Okay. So different approaches for different places. So yeah, for Cape Town. Well let’s just say for South Africa I would not want to set up a company there. I would not want a legal resident visa there. Just spending time there, I agree would be enough for me. China is and sorry even when I talked earlier about Belgium and Portugal, that was a specific thing I was doing trying to get an EU passport for my kid. I just thought that would benefit his life if he had a European passport, so that he would have the right in whatever happens in the world politics in the next hundred years of his life, he would have the right to live in Europe if he wanted to or needed to. So that was something I was trying to do for him. And so in the process of trying to get him an EU new passport. I was temporarily a legal resident of Belgium and Portugal. That was an approach for that goal. China, they got their own thing going on. You can’t have a WeChat API unless you have a WeChat business account or either, sorry, a personal or business account. You can’t have that unless you’re a Chinese resident or have a Chinese business as a Wholly Foreign Owned Enterprise.
Derek Sivers
And same thing with like a Chinese phone number, whatever. Like they’ve just got their systems set up in such a way that the only way you can avail yourself of many of the great things they’ve got going on over there is to either be a resident or have a business there. So it’s not that I want to go create a business in every country in the world in order to feel connected to it. It’s just the right approach for that place. But yeah, for South Africa and many other places in the world, I’m going to Mexico for the first time in two months. I don’t think I will ever create a business in Mexico or become a legal resident of Mexico. Most places on Earth I will not be going through legal paperwork. I would feel connected to it just by spending time there. And most importantly, I found recently having good friends there makes me feel more connected to a place than just spending time there. If I spend time in a place but I don’t have friends there, I’ll only feel some connection. But having real friends that are from and in that place helps me feel even more connected to it.
Chelsea
That was actually one of my questions was about friendships and traveling and, you know, being nomadic. That’s the hardest thing about being nomadic in one of my opinions, is that you settle like you said, you start to become familiar with the community. The Pilates instructor knows your name. The barista knows your order, everyone knows who you are, and then you just up and leave, and you start again from square one. And there’s a magic in starting from square one and being like, “I’m going to figure all this out again by myself. I want to make new friends, new community.” And then again, it happens six months later. Last year I traveled to a new country every single month. I think that was way too quick for me to be traveling, and I got very burnt out and very exhausted. And I actually think there was a moment where I was kind of like very jaded. Like, what am I doing? I’m not even impressed by anything anymore. Nothing’s fun. I remember flying over the pyramids in Mexico, actually, and on a hot air balloon and being like, “All right, you know, when does this land like, this is beautiful, but I’m kind of ready to go back to my house.”
Chelsea
And I just remember being like, I know this is not how I want to feel. When I studied abroad when I was younger, I remember feeling this magic of landing in a new country and like running to all the restaurants and the plazas and the parks, and I feel like I lost that because of how quick I was going. I didn’t give myself any room to integrate, but I also started missing the communities, and I hated starting over from square one and saying bye to people. Even if it was a see you later, it was still a we’re never going to have this group of people again in this place at this time with these mindsets, and it becomes a little heartbreaking at times. And also just, I don’t know, there’s a moment where you’re like, “I’m sick of starting over.” And I’m just curious your point on that. Like, how have you made friends? I mean, I know you’ve been settled for a little bit, but how have you made friends from all over and kept in touch, especially with the different time zones? And what do you feel about kind of the starting over process every time you travel?
Derek Sivers
Well, first I found a good metaphor to describe what you did last year. When you’re making a puzzle. Good old fashioned jigsaw puzzle. You start with the edge pieces. And I think what you did last year was kind of like Chelsea’s edge pieces. You moved to 12 countries in 12 months or whatever. And like that’s a far extreme. It’s like, okay, well, now you know where that edge is. You’ve defined that edge that that was too much. It was a useful thing to do to know where that edge is, to know that was too much for you. That great example of flying over the Mexican pyramids and being kind of over it. Too many experiences in too short of a time. But I’m sure there’s another edge on the other side that would be like staying in Central Florida for 20 years would be the other edge of like, “No, that’s too much. Can’t handle it. I’m going to explode.” Friends? I’m really thankful that I grew up at a time where talking on the telephone was normal. That I left Hinsdale, Illinois in 1987 and moved to Boston, and I left Boston in 1990 and moved to New York City. And my friends from Boston moved out to California and down to Arizona. And we talked on the phone all the time. And then I moved out to Oregon, and I talked to my friends in Boston and New York and Los Angeles by phone. So really, ever since 1987, all of my friends have been phone friends.
Derek Sivers
All of my best friends have been phone friends. Very rarely have I lived in the same state as my dearest friends. Mostly my best friends have been phone friends, so that just continues as I live around the world. That there are just as you travel, I meet people that I click with and usually it’s instant. We can just tell right away, “Oh yeah, you’re cool.” And as long as this person is also up for talking on the phone sometimes, then that friendship is going to last forever. So two concrete examples, in Brooklyn, New York, is a singer songwriter that she and I met at a conference in Memphis, Tennessee, when she was 17 years old. And now this is like, I don’t know, 18 years ago. I think she’s mid-late 30s now. And as soon as we met, we just had this rapport and went, “Okay, you’re cool.” She’s like, “Yeah, you’re cool. All right.” So we have probably only spent maybe six hours in person, but we have spent 18 years talking on the phone and we talk on the phone almost every week. Well, yeah, let’s say a couple times a month for 18 years. And a more recent example on the flip side, as I went to Bangalore, India, last month, last year and I met with 50 people in nine days, just like, you know, one on one meetings, 1 or 2 hours each. I blogged it on my website if you want to see it. It was one of the most fascinating things I’ve ever done in my life, and I highly recommend it.
Derek Sivers
But one of those people had that kind of click that I very rarely get with anybody that we just couldn’t stop talking. So it’s like we met quickly in just one of these one hour meetings. And then we set up an appointment to meet the next morning at a cafe at 9 a.m., and luckily it was my free day that I didn’t have anything else scheduled because we sat down at this cafe at 9 a.m. and we couldn’t stop talking until 5 p.m. and finally she was just like, the cafe was closing. They’re kicking people out. She’s like, “Look, why don’t you come back to my house so you can meet my husband?” So then I sat and talked with her and her husband for six more hours until 11:00 at night. We just couldn’t stop talking. I haven’t seen her since, but in the last year and a half she and I talk every single day. She’s just my best friend now. We just share everything in our lives together. And she’s in India. And so, yeah, my best friends right now are currently in Perth, Australia. Bangalore, India, London, New York City and Los Angeles. Yeah. Oh, no and one of my best friends is nomadic. Also moves every 3 to 6 months with her husband. So these are my best friends and would continue being my best friends even if I was living in Chile or China.
Chelsea
I love that. It sounds like a lot of digital nomads I know will be able to relate to this too, is, I think, at least for nomads that don’t have long term visas, the constraint of a three month visa or a one month visa or whatever it is actually forces you to be like, I need to make friends and I need to make them quickly. And you don’t really have time for the, “Oh, where are you from? Cool. That’s amazing.” Like, it’s very like, let’s get to the point. And we always laugh because we’re like, you know, we’re on a vacation together and it’s been a week. And if I was living in Central Florida for 20 years, going on vacation with someone I met a week prior would be considered kind of insane. Like, you don’t even know this person. Why would you be going on a trip? Where here, I could be like, “Who wants to go to Japan next month?” And I could probably find five friends that want to go to Japan next month. And I think there is something to be said about the constraints. And I know that’s something you talk about a lot is constraints. And can you expand on the concept of how constraints actually expand you, not ironically, constrain you?
Derek Sivers
Good question. Just like death can give life meaning by setting a deadline. For something ending can help give more meaning to the time while it goes on. And that’s kind of the underlying message underneath vampire stories, where they just live for centuries and they’re just like, “There’s no meaning anymore.” That giving something a short time, I think, like, instead of saying, “I live in Florida and that’s that.” Instead of it’s like, “I’m in Florida for only three months. This might be the only time I will ever live in Florida. I’ve only got three months to do it. I might never come back.” Oh my gosh, there are so many things to do in the next three months. You can appreciate it. You can wake up early every morning and just step outside and go, “This humid air, this natural place full of life and foliage and strange creatures.” And appreciate it more than somebody who’s just been living there for decades. Yeah, short deadlines can really help you appreciate a place. I think when I moved to New Zealand in 2012, coming from Singapore especially, I appreciated New Zealand so much more than it seemed like anybody around me was appreciating it.
Derek Sivers
People that just lived here their whole lives and saw their grandparents and their parents, and they’ve grown up here. Just take it for granted. And they would sit at home and watch TV, and I’d be that example of bursting out the door at six in the morning every day, like, “Oh my God, smell that air. Oh my God, look at that moon. Wow, this is great. Let’s go hiking.” I just wanted to go experience it vividly because at the time, I thought I was only going to live here for six years, and that’s it. Like, that was the original plan. Stay here for six years and then move back to Singapore. Originally, we thought our kid was going to still grow up in Singapore. So yeah plans change, but even thinking that the deadline was six years made me just want to devour and appreciate it along the way. So I think it’s beautiful. The idea of appreciating the whole world with the deadline, and knowing you’re only going to be in South Africa for three months, and then you’ll go off to, you know, Norway or something and only be there for three months. And what appreciation that gives you. I think it’s a beautiful way to live.
Chelsea
It’s definitely an interesting way to live. It’s a beautiful way to live. And it reminds me of another book, “Four Thousand Weeks”. Have you read that one by Oliver Burkeman?
Derek Sivers
Yes, I love everything he’s written, so much so that I emailed him after. Usually when I love a book, I email the author to tell them so and sometimes they email back and Oliver Burkeman emailed back. I’m like, “Oliver Burkeman just emailed me.” Yeah.
Chelsea
I’m trying to get him on the podcast too. So we will tell him we both love his book and it changed my life. I have it right next to me. I started reading it again and I read it eight months ago and I never read books again. But there’s something he says that I know you have said as well about making decisions. And in the book he says for anyone that hasn’t read quick overview is that it’s, you know, kind of estimated that we have around 4000 weeks. And so pick how you want to spend those 4000 weeks. It also brings up the idea around something I know you talk about too is like monotasking and just focusing on one thing at a time, because we’re in a culture now, at least the orbit that I’m in is like, “I want to write a book and I want to launch a merch shop, and I want to be a wellness retreat service provider. And I want to make stickers.” And, you know, we all want to do 45 things all the time. And we also feel like there’s this deadline of, “But then I’m going to have a kid or then I might get sick when I’m older. So I have to do it all now.” And eventually sometimes we have to just make a decision. This is with business. This is with a partner. This is where you decide to live. But then it brings up the idea of like Useful Not True. Like, could you do the 45 things and live in 45 different countries and make it all work? And I’m just curious your yeah, your kind of viewpoint on decision making and like settling down and on one thing. We can talk about it from a relational standpoint or more creative.
Derek Sivers
In short, I like to remember that I can use the future that just like remembering that you have closets that you can keep things in, You don’t need to keep them all out on the floor or on your desk. You can put things in the future. Like, I want to learn Chinese and I want to learn the Python programming language. And I want to write a book. Oh my God, I can’t do all those three things. I’m overwhelmed, I can’t decide. Well, just pick one now and put the other two in the closet to do next when you’re done. Get them off your desk. Do one thing at a time to completion, and then you do the other thing. Unless it’s something that can really be an antidote for something else. Like, I want to get a PhD and I want to be a weightlifter. Okay, well, getting a PhD is going to be a lot of sitting and reading and writing and being a good weightlifter only takes an hour to 90 minutes a day. You can’t do it 18 hours a day. So those are two very good complements for each other that you can pursue those two things, but then exclude other things. It doesn’t mean you’re also going to be a master of social media and a socialite. You’re just going to do a PhD and be a weightlifter. That’s all you’re going to do. And then if you also want to travel the world, okay, well then that’s in the closet that you’ll be taking that out of the closet and putting it on your desk as soon as you finish your PhD or whatever. So yeah, I use the future like I use a closet or a storage box.
Chelsea
I know everyone is going to be asking, how do you choose the thing. Like the programming sounds really important, but, you know, learning this language, if I want to move there in a few years sounds important, but everything feels high priority and urgent. How do you go through that decision making process?
Derek Sivers
I mean, you could either just notice what your natural inclination is. The value of a coin toss is not seeing whether it lands on heads or tails. It’s noticing whether you are disappointed in the result or what you’re wishing for when it’s flipping, you know, you’re like, “Okay, well, get a PhD or travel the world.” 50/50. You toss a coin and in the air, if you just notice even the slightest little bit, you’re just like, “Oh, please be travel the world.” Well, then there’s your answer. Doesn’t matter what the coin actually says. It’s that moment that you notice in yourself that you want one a little more than the other, or you just make a rational, left brained, Spock data driven decision. God, I can’t believe I just quoted a Star Trek character. I don’t like Star Trek. And then you make your emotions align with it. So, for example, say that you are currently bound to a place for a few years. You need to finish this. Or like in my case, where I have a kid and his mother doesn’t want to move. So here we are for at least six more years. If I want to be a good dad, then I am bound to New Zealand for six more years. You could just use some concrete facts like that to say, “Okay, well then traveling the world is going to have to wait, but I can start learning the language now before I travel.” So say, if I want to spend more time in the future in China, I can start spending two hours a day learning Chinese now.
Derek Sivers
And I can do that in the background for the next six years. So that six years from now, when I go to China, I’ll be more prepared or something is more urgent, something is more important. Something would have a greater benefit for doing it sooner rather than later. You just can make these rational decisions and then kind of like cognitive behavioral therapy where you just stack up your reasons. You just prove to yourself you make a strong argument. You remind yourself why this is important. You stack up a whole bunch of evidence and you just decide, “Yes, this is what I’m choosing. I’m going for this because it just makes rational sense.” And lastly, don’t forget the donkey. Meaning there’s the tale of Buridan’s donkey. B-ur-i-d-a-n you can look up online. I think it’s an old tale from a hundreds of years ago that there is a donkey that was halfway in between a pile of hay and a bucket of water. He was both hungry and thirsty, and he couldn’t decide. He just kept looking at the water and the hay, and eventually just died of hunger and thirst because he couldn’t decide if the donkey would have had any foresight. He could have seen, “All right, I can go eat and then I can go drink, or vice versa.” You can have both. You just have to have some foresight.
Chelsea
I love that tale. One of my mentors, always says, like, you can have it all, but not at once. And I think that’s kind of what Oliver Burkeman says, too, is like, you know, you can write a book, but maybe you’re having a kid and buying a house and starting a new PhD program. Yeah, it’s going to be pretty difficult to write a book unless you want to work 90 hour weeks. And so pick one thing, focus and use the future, like you said, to be able to pull it out. They’re very similar concepts, actually about monotasking and picking one thing. And I remember something you said...
Derek Sivers
Hold on. Wait. Let’s stick with that for one more second. That a more extreme way of saying that is you can have anything, but you can’t have everything. You have to decide. And if you can’t decide, then you get nothing.
Chelsea
That one’s good.
Derek Sivers
How about that. If you don’t decide then you get nothing. I just made that up right now, I like it.
Chelsea
Oh we like it. We’re going to mark it in the transcript. If you don’t decide you get nothing because it’s true. I mean, I also learned half the things I’m asking you. I’ve learned from you about deciding actually means to cut off. Oh, yeah. That’s the Latin root.
Derek Sivers
I learned that from a Tony Robbins book in the 80s
Derek Sivers
Oh, about deciding or about the Latin root?
Chelsea
Can you talk about that a little bit?
Chelsea
Yeah, about how deciding if you actually think about it, it means to cut off. So when you’re making a decision, you are cutting off the other option to be able to make space for the new option. I think that’s kind of the concept. I don’t know actually, if we need you to...
Derek Sivers
Yeah, you just said it. Yeah, I got that sentence in passing from a Tony Robbins book in 1989, and I went, “Ooh, interesting. Decide means to cut off.” So yeah, that’s it. I don’t know, I’ve been quoting it ever since.
Chelsea
I love that, it goes back to the donkey thing of he ended up, you know, dying because he didn’t make a decision. I think that also ties to perfectionism. And I’ve been reading a lot about perfectionism, because I think a lot of people like to say they’re perfectionists because it has a more positive connotation. Like, “I have really good taste. So I just want to make sure. I’m a perfectionist. Everything has to be perfect.” And there’s this illusion that, “Oh, they must have, like they’re really smart and have good taste and they’re in this like mastermind mad scientist mode. And then when it comes out, it’s going to be this amazing thing.” But in reality, perfectionism and procrastination are also forms of self-protection. Because if you never have the option to be critiqued or perceived, then you get to stay in your little bubble and be like, “Oh, it’s coming, it’s coming, it’s coming, it’s coming.” And it never comes. And I’m just curious, yeah, your thoughts on perfectionism and maybe procrastination as well.
Derek Sivers
I don’t really have many thoughts on perfectionism, except I never had that positive association with it. I’m surprised that you just said that somebody would say it for status seeking, because to me, when somebody says they’re a perfectionist, I just hear it as bullshit. I hear it as like, no, you’re just scared. You have no perspective. You have no boundaries that look, I’ve been writing songs and recording music since 1984, and I know that at a certain point you have to cut it off and say, “There we go. That’s good enough. I’ve done six takes of this vocal, and now I know that take number three was the right one. We’ll stick with that.” So maybe I’ve just seen this from decades of experience, that somebody who calls himself a perfectionist is somebody who’s going to take six years to record an album that somebody else would take six months to record. And maybe again, I’m seeing this in the bigger picture that it can mean less of a life if you end up doing less because you’re sweating every last detail in trying to, like you said, micromanage it, or a form of procrastination and fear. But that said, I can also see the flip side that my last book called “How to Live”, and even this next book called “Useful Not True”.
Derek Sivers
I am really fine tuning every word, like really reading every chapter out loud, choosing words because of their rhythm and their inner rhyme. And like every single word, gets put under a harsh trial and microscope. Because that’s the kind of book I want to make, is where it sounds almost like poetry or like song lyrics, where reading it has a nice rhythm and a sound to it. And even if you didn’t know English, you’d listen to it and like the way it sounded. That’s what I want to make. And so that is not meant to be perfectionism, but I could see how it could be seen like perfectionism from the outside, even though that’s not my intention. So who knows? Maybe some people calling themselves perfectionists are not doing it for the status. It’s just reflecting what they want to put out in the world. Whereas somebody else is happy to shit out a Kindle e-book every month, you know, “Blah blah blah. Here’s a whole bunch of shit on my mind. Bla bla bla bla bla bla.” Send upload it, good enough. And if that’s who they want to be in the world, that’s cool.
Derek Sivers
If that’s their value system that they want to publish a book every month. And hey, you know, it’s got some rough edges, but fuck it. If that makes them happy, that’s who they want to be. That’s great. But I like this idea of rarely communicating with the world. But when I do, it’s implied that I’ve done my best on this and this is something really worth paying attention to. I even take that same approach with social media. In fact, that’s why you don’t really see me on social media anymore is that as soon as I joined Twitter, within months I had 300 000 followers and I felt, “Whoa, like my microphone is on.” I’m like, standing in Madison Square Garden with 300,000 people in the audience, and everything I say into this microphone better be fucking worth bothering 300,000 people with. And so I ended up saying almost nothing because I’m like, you know, I don’t want to put noise into the world. So I tweeted very rarely. And then after Elon Musk came in and changed the API, I was just like, yeah, fuck it. So just not there anymore.
Chelsea
That’s so interesting. I think the second example you used is what a lot of people maybe think they’re doing of like, maybe some people are, I’ll speak for one group of people and the other that they think I just have really high standards, a really high level of whatever it is right, quality expectations. I want this to feel more rare, I think is the word you use. Than, you know, “Oh, I’m just doing whatever. And if good enough and done is better than perfect.” And I think that’s what perfectionists a lot of times think is, “I just have really, really, really, really great taste and I want to be able to reflect that.” And I’m curious for you with your writing process specifically, especially with this book that you’re talking about, how do you know it’s done? Like, is there a feeling, you just read it and you’re like, “Okay, it flows. We’re done.” How do you know?
Derek Sivers
I’ll remember that question and answer that next. But first I was just realizing that I think my problem with the term perfectionist is the -ist. It’s the -isms and the -ists that people use to label themselves to say, “I am a Buddhist. I am into Stoicism.” And they want this cultural projection of identity. This is who I am. I am into stoicism. I am a practicing such and such -ist. Which is kind of bullshit because it just means like you’re adopting an entire collection of beliefs instead of just picking and choosing the ones you need. I’m so suspicious or avoidant of all -isms and -ists and I just don’t believe them. So I just realized I was reacting more to the idea that you described to somebody calling themselves a perfectionist. That sounds to me like you’re asking others to think of you that way. That you care what other people think. And you’re calling yourself this because you want people to think of you this way instead of just doing your fucking work. So anyway, your next question. How do you know when it’s done? I think the real key is just asking yourself, would I be proud of this? Am I ready to release it? And I love the double meaning of that word. Release. I release an album, I release a book. You let go of it. It belongs to the world.
Derek Sivers
Now it’s out of your hands. I’m asking myself that right now. Your question has perfect timing, Because yeah, last night, until ten minutes before I went to sleep, I was working still on the final edits to my next book and starting to feel that feeling of just like the combination of being happy with it as is and just feeling kind of over it. You know, like the return on investment of my time, maybe that’s it. That first, your time spent on anything is making huge changes. It’s going from nothing to something and then from bad something to pretty good something, and then from pretty good something to really good something. And after a while you could spend 20 more hours on it, and you’d really only be getting from 98% to 99%. And that’s maybe not the best use of 20 hours of your life. Oliver Burkeman. So you start to notice that that your time and effort spent is having very little improvement. And then you just have to convince yourself that that’s good enough, because it’s more important if you value your time and life to get this thing out into the world, release it, let people read it and move on and do other things with your time. If you value your time and your life’s energy at all, it’s time to do something else when you’re not getting great returns.
Chelsea
Amen. I have two questions coming out of that. I think the first is more practical that a lot of people listening to this podcast are probably like three years into business or less. So they’re still finding their footing and they’re trying to figure out systems. And do I need to hire this person? Do I even need to hire anybody? It’s a lot of throwing spaghetti at the wall and seeing what’s sticking. And so sometimes the concept of time of, “Oh, I’m going to wait and do three more revisions and then I’m going to get it out.” Sometimes that doesn’t work if you are in a financial bind. Like I remember being so broke in Australia when I started my business, I was living off my tax refund, a stimulus check. I was cleaning houses for money and nannying and I was desperate. I was like, “I have to put something out there to exchange for money if I want to get out of this situation.” So there was something to be said about being thrown in the deep end with cinder blocks on my feet and being like, you better figure out a way to swim that lit that fire under me to be like, let’s go. Let’s just throw stuff out and see what happens. And I can also reflect back on that time and say, okay, yeah, that maybe wasn’t my best work ever, but it got me out of the financial bind that I was in. So I’m curious, your advice to people that are like, I want this to be high quality and done and just like have it be. I’m so proud of it, but I need to make money and I need to get something out there.
Derek Sivers
That’s a great question. And I’m glad you brought it up, because it reminds us that there are different motivations for creating. That somebody might just be creating as quick and fast as they can to make money, where somebody else might be creating something that they feel is like their life’s legacy. And those are two very different motivations, even though they’re technically the same action, two very different goals and standards and purposes. So cranking things out quickly is an amazing way to get better at what you do. I ran a recording studio in New York City for a few years Where clients would come in and we’ve got three hours to record this song and boom, boom, boom. I had to get super quick. Also, they were paying me by the hour and they were paying well, so I had to be super fast with the software and with this and be able to pull up the sounds. And they said, “Okay, I’m ready to lay down the guitar solo.” I’ve got a patch in the chords, pull up the sound, get the amp, get the microphone in the right place, quickly pull out that guitar solo sound. They said, “No, give it a little more treble, you know. Can you give it some more of that crunch?” And I’ve got to do this so quickly. I don’t remember the music we made in those years, but damn, I got good at running a recording studio under that high pressure. And now, as a writer and a fan of great nonfiction books, I think it’s no accident that the most gripping writer I’ve ever read started out as a journalist under tight deadlines. I should just say who it is. Neil Strauss has only written a few books, but damn, when I look back every time, I stayed up all night long reading a book.
Derek Sivers
I mean, like, laid down to read it at 7 p.m. and at 2 a.m. even though my eyes were so tired, it’s like I couldn’t stop. Like, “But then what? And then what?” And I stayed up until five in the morning reading a book. That’s only happened four times in the last 20 years. And three of the four were Neil Strauss books. And I didn’t realize that until hindsight. I was like, “Damn, Neil, well done.” By the way, the fourth one was “The Da Vinci Code”, which I read at a friend’s house while I was in Israel 20 years ago. Yeah. 20 years ago. Wow. And yeah had it on the bedside table. Was like, “Oh, Da Vinci Code. I’ve heard of this.” And I picked it up at, like, 8:00 at night. I was like, “Whoa. Oh my God. And then what?” So anyway, I think that writers hone their skill amazingly well when they’ve got the tight deadlines and they have to crank out a column and they’ve got two hours to do it, and your boss is breathing down your neck. And, “Here’s the information we need this now.” And maybe the work along the way wasn’t amazing, but damn, it makes you better at what you do. So different purposes, I think there’s this idea floating out there. I’ve heard many times it’s not mine that most of what we make is fertilizer. So you can use the double meaning of that, that most of it is shit, but it helps the good shit grow. Or it helps the beautiful flowers grow.
Chelsea
Yeah, I think repetition and iteration and being able to look at data points and look back and say, this worked, this didn’t. You will never know until you have something to work with. I think kind of going back to the idea of perfect, I don’t know why this is like on my mind lately is, I think of a ball of clay going on a pottery wheel and someone being like, “I’m going to make the perfect vase.” But then they just sit there and look at the ball of clay and like, this is going to be perfect. And then they start, you know, the wheel spins around, they start making it, and they’re like, “Wait, actually, this is going to be a beautiful mug.” And then as they’re shaping it, it turns out to be, you know, a huge fruit bowl. And they did not know until they got started. And I think there’s something to be said about just start, get the thing moving. Get your hands dirty in the clay, start moving it around to shape it and see what it is. And it reminds me of I think it’s in your book, “Anything You Want” of like be open to things changing as you keep iterating. Like that’s what success is, is constant iteration. And I’m curious if you can explain a little bit more about that and how has that changed as you’ve gotten older and tried on so many different hats?
Derek Sivers
Yeah, I mean, I love the example you just gave. It’s a beautiful metaphor. Put the clay on the wheel first, start spinning it, then you’ll discover what it is. I like that a lot. That’s a good, good, good metaphor. I just was speaking from experience that when I started my business, I thought it was going to be kind of like PayPal, because it was at a time before PayPal existed. I spent $1,000 and got a credit card merchant account, which was much harder back then. I’m talking 1997. Now you can just go to Stripe.com and sign up and be ready in three minutes. But then it was like $1,000 in setup fees. You had to have a legal business. They actually sent an inspector out to your location to make sure you had a valid business, that you were not running from your home, that was not allowed. It was a lot of paperwork to set up but after all that work, after three months, you had a credit card merchant account. You were now allowed to charge people’s credit card. So after doing that work, I thought I should share this with my friends that are not going to do all that work. And so I thought it was going to be like PayPal, that I was just going to be charging people’s credit cards and taking a little service fee for doing this. And so I did this for my musician friends. I charged customers credit cards for people who wanted to buy their music online. But then, well, okay, two things. Two instant things happened. For one, the first guy I did this for, I charged the customer’s credit card.
Derek Sivers
I said, “Okay, the guy has been charged $27. Go ship out the two CDs to this address.” And he said, “All right.” And then the customer contacted me two weeks later and said, “Hey, my CDs never showed up.” And so then I had to go to the musician and say, “Hey, his CDs never showed up.” And then the musician said, “Oh, dude, I totally flaked. I totally forgot to do it. I’m so sorry.” And I went, “Oh, okay, this sucks.” I was like, “All right, just give me your CDs. And then as soon as a customer pays, I’ll ship them.” And he said, “Oh, thanks, man.” So now I’m in a charging credit card and shipping business, even though I’m like, you know, three weeks into my idea and then the second person I ever shipped CDs to came back to me two weeks later saying, “Where are your new arrivals?” And I went, “What do you mean new arrivals? Like, which of my friends am I now processing credit cards for?” And he goes, “Oh, sorry, I thought you were a record store.” And I went, “Oh, huh. I never thought about that. I could be a record store.” And so just like that the plan totally changed a few weeks into it. So yeah, it’s the business version of what you just said with the clay pot. You throw the clay on the wheel first, start spinning and see what happens. The world tells you what it wants. So true.
Chelsea
So true. The world tells you what it wants. And you will also feel into something and be like, “Wow, I thought this was a good idea. And now that I’m actually in it, I don’t like doing this. I don’t like being here.” Maybe I needed to do this from a different angle. Or maybe I wanted to be the strategist, but not the actual execution person. There’s so many different ways you can still be involved, but not maybe at the level that you thought.
Derek Sivers
Intrinsic motivation is the oil in the machine, that the machine can go without you being intrinsically motivated to do it, but it’s going to grind to a halt pretty soon. On the other hand, a machine that’s well oiled, meaning you’ve just got intrinsic motivation and are into it. That could just go fast and forever. So you do need to pay attention to your intrinsic motivation to notice what’s exciting you and steer that direction.
Chelsea
Has there been anything that you’ve worked on before that it started out intrinsically motivated, and as you got further into it, you’re like, I do not like this, and I need to get out?
Derek Sivers
Okay. I do not like this and I need to get out. Are two very different things. There have been many, many things that I started full of excitement and finished full of screaming and kicking and cursing, but I just had to do it. So the top example that comes to mind is I started a web hosting business called Host Baby that had a wizard that I built in PHP. I did all the programming myself so that you could just answer a bunch of questions, and it would generate a website for you. I had the vision for this thing. I knew how it would work. I knew that I could do it, but it was at the outer limits of my capabilities in programming at the time. But I knew I could do it. But as I got, you know, say like 500 hours into it, I was just like, “I hate this fuck.” That I just made myself finish. I was like, I know people need this. I know if I just finish it, the world will be thankful for it and it’ll be profitable. It’s necessary. I was like, “I would rather do anything else right now.”
Derek Sivers
Anything. Please help, you know? But instead I was just like get a Diet Coke or whatever and crank some tunes and just make myself sit down and finish it. So Host Baby, web hosting was one example of that, but I’ve had many examples of that since. Even some of my books. Even when it gets to that final bit, I’m like, “Ah, fuck, how do I explain this concept?” Oh, it would be so much easier to just go ride my bike instead, or just go play a video game or some stupid thing. Surf the web, distract myself with entertainment. I was like, “No. Ah.” Get some caffeine. You know, shut off the internet. Sometimes I literally go over to the internet modem in the closet and I power it off. All right, hold down the power button on my phone for three seconds. Swipe it over. It’s off there. Now I can’t get online. I can’t be distracted. Like, ah. I kick and I scream literally. Well, I scream, I don’t kick things, but yeah, stomping and screaming and I’ll just make myself finish it. So yeah, you don’t have to love it.
Chelsea
You don’t have to love it, but you might want to get it done. But it does actually remind me of something I think I’ve heard you either say on podcasts or maybe you wrote about it, was you don’t actually have to do anything like you personally decide what you want to do. And so like for example, let’s use the book like you didn’t have to finish that book. You could have just said, “Ah, maybe this is something I don’t do in this lifetime right now.” And I’m curious, how do you decide what do you have to do? Like, what is your personal motivation?
Derek Sivers
I don’t know if there’s any cut measure. It’s just the whole subtle stack of values in your unique situation for what matters to you. Mixed in with things like money, time, who you want to be in the world, what makes you happy to wake up in the morning? What makes life feel worth living for you? He’s the combination of all these things for you makes you feel that something is worth doing, even if it’s going to be hard along the way. It’s worth it anyway, whether it’s for the greater good or dammit, you just want the money. Any of these can be enough of a reason that you just make yourself do it or let it go. Like maybe you told yourself you want to be a digital nomad because you read some appealing articles about it and it sounds cool, and you start doing it and you realize that you don’t like talking on the phone. You miss your friends. You’re an in-person kind of friend that likes to be hanging out in person, that likes to be living in the same place with your best friends, and that you’re lonely as hell. And so, three months into what you thought was going to be the rest of your life, you say, “You know what? Now that I’ve tried this, I don’t like it. I don’t have to do this.”
Derek Sivers
Even though I announced to the whole world, you know, “Hey, I’m going to be living in 12 countries in 12 months. Just watch me go.” You know, you could, three months into it, say, “No, I’m not enjoying this. I just want to stay in one place and that one place is San Diego or whatever it might be.” Then fuck it, change your plans. Don’t worry about what you’ve told other people. In fact, I think announcing your plans can really mess with your motivations. Because now you’re thinking about what others think of you when the truth is, most people don’t think of you anyway. And if you announce to the world that you’ve changed your mind, well then most people go, “Okay, whatever, I don’t care. Didn’t care the first time. Don’t care this time.” It can be much better to keep these things to yourself and do less announcing. Also to make sure that you’re doing it for yourself and not just because of what others might think of you.
Chelsea
That is such a big lesson I’ve learned not only in entrepreneurship, but creativity is, I need to stop announcing every move that I’m going to do. Like there was a few weeks ago where I had this idea of I want to do a magazine online, kind of like a Substack, but it’s going to have so many different elements. There’s going to be audio elements, and then there’s going to be essays. And I was really like, on this adrenaline rush of like, this is going to be a magazine that is like no one’s ever seen before. And I started talking to someone who’s like, I’ve written one, I can help you. And I’m like announcing it on my Instagram. I was like, “I think I’m starting a magazine.” And then five days later I was like, “What are you doing? Like, you do not have the time.” I don’t actually want to do that. Like, I think I just am very motivated by creative output. And someone kind of pointed out to me, they’re like, “That’s already what your Substack is.” I have a Substack called Slight Turbulence where I share stories and videos and photos, and they’re like, “Is that not kind of a version of a magazine that you had in your head?” And I was like, “Good point. I think I just had a different look to it.” But then it made me realize, yeah, I don’t need to announce things every single time I have an idea in my head. Because then to your point, I did feel this weird pressure of like, “Well, people are now looking out for a magazine that I made a big hubbub about.
Chelsea
And no one’s followed up. No one actually really cares. No one’s messaged me being like, “Where’s that magazine?” And it’s so funny how we really think that the world is staring at their phone, waiting for us to announce the next thing. And where’s that thing that you said you were going to do? And I think there’s something to be said about integrity. And, you know, if you’re saying something and you’re charging people for it and it’s it’s coming out. It’s coming out, that’s a different, you know, that’s a whole different level. But having an idea and announcing it every time you think you have a good idea, that’s that’s just totally different. I want to talk a little bit about your writing style because you have a very unique style, and I’ve read some tips that you have. That like stack your sentences into a new line each time so you can see like the cleanliness of the sentence. And are there unnecessary words and what’s fluff and what’s not? I am very verbose. I have a podcast. I like to write long form essays. I’m talking to you for almost two hours now. Like I have a hard time reeling it in and deciding what stays and what goes. And I especially love specificity in storytelling. Like, I really love the specifics and the context. I’m curious, how did you come into this writing style and share a little bit more about your writing Philosophies or tips, because there’s a lot of people in this audience that are writers.
Derek Sivers
Oh, okay. Well, first, I don’t think that there’s a right or wrong way to do it. So please don’t think that because I write really succinctly, I think that’s what everyone should do. I love some verbose writers, and I’m also a verbose conversationalist that if a friend of mine, say, went out last night and I said, “What did you do last night?” He’d say, oh”, we went out.” I said, “And he did what?” “Oh, we went to this new event. It was all right. I’m like, come on, give me the play by play.” So you get there, “What did you see? You stepped in. What was it like? Who did you like? Come on, give me all the details.” So I like verbosity in conversation. I like it in some people’s writing. But for me, for the kind of books I’m writing, it feels like it’s more powerful if I say a little less and let you fill in the blanks, because I’m trying to get you into a different way of thinking. And it’s unique for everybody. So instead of me hammering every point to death and giving you a bunch of unnecessary examples as if you’re an idiot. Which even then you’d be distracted by my examples. Instead if I keep it succinct, then you fill in the gaps yourself, almost like bespoke clothing that I’ll put the idea out there succinctly, deliberately not saying everything there is to say about this, and then you can take that and think of how it could fit you, like the clothing example. Well, I’ve also noticed that it can be really frustrating when I’m reading a nonfiction book that is just trying to communicate one idea, and they go on and on and on for 300 pages about something that could have been said in a powerful 80 pages, but damn it, they took 350 pages to say it, and it just feels like such a waste of my time.
Derek Sivers
It feels inconsiderate that because your publisher told you that you could sell more books if it was a thicker spine, so please give us 300 pages on the subject. Or maybe you think that it boosts your ego to make you look like more of an expert, if you have more to say on this subject. And because of that, you’re blathering on four times longer than you need to. It’s selfish. It’s good for you, but it’s inconsiderate for me. For me as a reader, if you value my time, I want you to be succinct for this kind of communication that I’m talking about, where you’re just trying to get an idea from your head into mine for me to use. It’s not painting a picture and it helping me vividly feel your day to day life in Brazil or what it was like to go through this stage in your life, you know, for this kind of nonfiction, kind of philosophical writing. I think it can be very considerate to be succinct, and it’s also just to my taste, more beautiful when you can be succinct. And it can be more memorable. The reason we can remember an Aesop’s fable and tell the story of the tortoise and the hare is because really, it’s only like 12 sentences. It’s such a simple little story that it fits in a nutshell, that you can keep in your pocket and open up when needed.
Derek Sivers
Whereas big, long stories can feel too long to tell, and so you don’t tell them to anybody else. But tiny little tales get shared. For all these reasons, I really try hard to be really succinct and yeah, look at every single word and question its existence. Like even a sentence, like, “In my opinion, blah blah blah.” And I look at that and I think, well, everything I’m saying here is clearly my opinion. I don’t need to say that. I’ll just say blah, blah, blah. And anybody reading that will have to know this is my opinion. They know that I’m not their boss. I’m not the center of their life. They know I’m just one voice in the choir. Yeah, it also helped that I got positive feedback from doing things this way because of my first book. It was really Seth Godin’s idea when he started his new publishing company called Domino way back in 2011. He called me up and said, “Derek, it’s Seth Godin.” And I went, “Oh my God, wow, Seth Godin. Hi.” He said, “I’m starting a new publishing company and I want you to be my first author.” I went, “Okay.” And I had never intended to write a book, and people had asked me to write a book, and I’d said, no. But when Seth Godin calls, you say yes. And he said, “It’s going to be a manifesto. Think of it like a manifesto, not a book like 11,000 words.” Which is like 88 pages.
Derek Sivers
And I said, “Okay.” He said, “Could you write your story about the music business and how you started and grew and sold your company in 88 pages?” I said, “Fuck yeah.” So I did, and people thanked me so much in the years following for making the book so short. They say, because it’s so short, it’s easy for me to gift it to people. I can give somebody an 88 page book and say, “You should read this.” I can’t give somebody a 600 page book and say, you should read this. That’s inconsiderate and even article length If I keep my articles short, like 20 sentences, I think people are more likely to read them than if they click on it and it’s like a ten minute read. They’re like, “Oh, I’ll get to this later. I’m busy.” And then they never will. But if it’s something they can read in 30s, I think it’s more likely to be read. So all that being said, put it all together. And yes, my chapters in my books are an average length of 22 sentences and my books are about a hundred pages. And I find this format so useful. It makes me proud of being so succinct. It lets other people fill in the blanks instead of me trying to be the final word on anything, which is kind of egotistical. I like the humble thing of saying, “Here’s a little idea. Do with it what you want. You are smart. You can adapt this for your own use.” Yeah, there you go. There’s my thoughts on being succinct.
Chelsea
And I think there’s something to be said about the fact that throughout this conversation, I brought up so many examples of your writing because I remembered it. And it’s not like I read the books five times back to back. It was concepts that boom, I read it once and it stuck and it stayed there. And, you know, almost a year later I’m interviewing you about it. And I was like, wait, I just remembered this because it was so memorable. Sometimes, actually, your emails are so short that I think you’re personally emailing me because it’s just so it’s like hey--
Chelsea
And I’m like, wait, I know we’ve emailed about this interview, right? So then I’m like, maybe he is just actually emailing me. I don’t think he sent this out to his list. And then later I’ll be like, wait, I think that was to his list. And I think that’s an incredible way to email.
Derek Sivers
Good. Right.
Derek Sivers
Thank you. I don’t mean to be deceptive. But when I get emails from friends, it’ll just be like two sentences, “Yo, dude, how’s the 13th look for you?” That’s what emails from friends sound like. And when you get some fucking corporate newsletter, it’s like, “In the beginning when I was this. Is in the following four points, you know, looking back I’d say that I was...” And you start to open these emails and you’re like, “Oh crap.” You look down, it’s like 12 paragraphs. You think, okay, I’ll read that later after other things. And then of course, you never do. So I never wanted it to be one of those newsletter types, although I know there’s some people that love it. And there was one newsletter I received, the only time I subscribed to a Substack once. There was a-- I’ll admit it was a friend of mine, but her newsletters were the classic like memoir autobiography. Let me tell you a tale. You know, when I was a little girl and da da da da da, you know. But she was really good at writing them. I should name drop Aly Tadros has a good Substack. And so that was the only exception that when those long emails came in, I was just like, “You know what? All right, I’m going to go get a cup of tea. I’m going to spend ten minutes reading this email.” And that felt worth it. But no, for the most part, as soon as I see that an email is long, it just gets skipped.
Chelsea
I’m laughing because I just wrapped up a course launch, um, where I did a bunch of email marketing and my new hire. She’s like an operations strategist. I asked her to take all the emails and put them in notion so that we can look and review the data after this course launch. And she goes, “I’m trying to pace them, but they’re actually so long they won’t be like paced all the way.” And I was like, “Okay good to know.”
Chelsea
So next round we’re gonna tighten them up a little bit. I’m going to take a page out of the Derek Sivers book. Here’s two quick things you might enjoy. And I think this is the fun of creating is experimenting. I didn’t look at that as like, you know, a dig at my emails or anything. I was like, it’s an experiment. Like, okay, next round of this, of this launch, I’m going to actually try pretty brief emails and make my point. And maybe five sentences, not 50. So I really love hearing how it’s worked for you, becausse it’s always nice to hear how creatives think and write and how it’s perceived in the world and how people find it useful. Because I know for me, it’s been useful the way you write and and comprehension wise, it’s been very useful. Yeah.
Derek Sivers
So, Chelsea, there was a book I read so long ago, I think I was 19 years old, and I read a book by Herb Cohen called “You Can Negotiate Anything”. It’s at the top of my list now. If you go to the book list on my website sive.rs/book, you see the 400 books that I’ve read in the last whatever years with my notes on them. This book should be right at the top of that list, because it’s so good, that list is sorted with my top recommendations up top by default. “You Can Negotiate Anything” by Herb Cohen, read it when I was 19 and thought about it for years after, and so just a year or two ago, I said, “You know, I’m going to go reread that book.” I went and bought an old used copy. I read it and oh my God, I remembered everything. Whereas, you know, there are some books or even movies that when you watch it the second time, even eight years later, you think, “Wow, I don’t remember any of this.” But that Herb Cohen book I remembered so well, and it’s because he made actual visual stories instead of just saying a point. He said, “One time my wife and I were we needed to buy a fridge.” And even just stupid little details, he said, “Because you know how women are, they just always want to stick more stuff in the fridge. So there we were, on a hot day at the appliance store, and a man comes up to me thinking he’s gonna make his sales quota from me that day. And I say like, you know, ‘What do you got on sale? What’s a discount?’ And he looked at me with a twinkle in his eye, and he looked at the missus and he, you know, decided he was going to try to sell me the big fridge. And I said, ‘No, I want a damaged fridge. You got anything that’s broken that I can get for cheap?’ And, you know, what I was doing is I was setting the baseline. I was lowering his expectations so that he was just happy to even make $3 off of me.”
Derek Sivers
But just the fact that he gave these silly, vivid examples. I know that when I read that book at 19, I pictured it in my head. Like in my head, I can still imagine this author and his wife and their teenage son in the appliance store because he described it. And there I can remember the lesson of setting expectations. And he did another one that was brilliant, where he talked about a prisoner in solitary confinement that wants a cigarette. And he said, “You think you can’t negotiate? Here, let’s just pick an extreme example. You can always negotiate. Let’s say you’re a prisoner in solitary confinement and you want a cigarette from the guard. If you say, ‘Please guard, could you please give me a cigarette?’ What do you think that guard is going to do? You’ll be lucky if he doesn’t spit on you. But instead, if you say, ‘Hey, guard, I really want a cigarette.’ And the guard said, ‘Tough luck. You’re not getting one.’ ‘You say, okay, well, I’m going to bash my head against the wall until I bleed and I’m going to pass out, and then you’re going to have to file a report. And even though they won’t believe me when I say that you beat me up, I’m going to say that you beat me up, and then you’re going to have to file paperwork and appear to defend yourself, and it’s going to be hours of your life. All of that could be saved if you just give me one stupid cigarette.’ And at that point, the guard is going to hate you, but you’ll get your cigarette. And in fact, he’ll even light it for you.”
Derek Sivers
And again, instead of just saying, you know, dear reader, you can negotiate anything, even the most desperate situations can still be negotiated. That wouldn’t have stuck with me, but making up a little tale of a prisoner in solitary confinement bashing his head against the wall helped me remember that story. Like, how old am I? Like 35 years later, I still remember what I read when I was 19. It amazed me going back and rereading that book. And so with lucky timing, I reread “You Can Negotiate Anything” by Herb Cohen just as I was preparing to write my next book, “Useful Not True”. And whereas my last book called “How to Live” had no stories, it was just directives. Do this, do this, do this, do this. The new book is mostly stories. For every point I wanted to communicate, I would make myself make up a little fable that communicates the point.
Chelsea
I love that. I am someone who does so well with specifics. I already remember one of the stories from “Useful Not True”.
Derek Sivers
Which one?
Chelsea
The brain surgery and poking part of the brain, and they’re laughing at the picture on the wall because they think of this specific thing is funny. But then they do the experiment again and poke on there. And I was like, wow, isn’t that crazy? Just because of how specific I could visualize someone in the room looking at the wall, thinking of this. Like there’s just something about building that world that makes me remember the point that you’re trying to make. So I love that you prefaced all this with saying like, there’s no right way, because I think when people look at accomplished, successful authors like yourself, they might go run and think, “Well, I need to go edit everything and make it as succinct and brief as possible.” When in reality someone might like your poetic, verbose, long winded kind of way of writing. And I think you have to like it too. I think that’s a big point you’ve made throughout this conversation is like, do I like this? Do I like doing it this way? Am I proud of this? Is this fun to write? And it seems like you get a lot of joy out of doing it that way for you.
Derek Sivers
Yeah, and sorry, I always make a music comparison, or I always think in music comparisons that there are musicians like John Coltrane that would play what other jazz musicians called scrambled eggs as he would just blah blah blah. Blah blah blah blah blah blah blah blah blah blah. And John Coltrane was wonderful and people loved John Coltrane. And then you’d have Miles Davis who would come in and just go for a ba ba ba ba ba ba. And people loved Miles Davis. It’s just whatever style you feel is the expression of your soul or what you feel like putting out into the world, and it can change per project. You might put out a thousand page book like a David Foster Wallace, a Gödel, Escher, Bach. Huge slogging masterpiece that few people read, but those who do are transformed by it. And then your next book could be 100 pages of little children’s fables. You know, you don’t need to stick with one style just because it’s what you’ve done before. In fact, you might want to challenge yourself to do the opposite of what you’ve done before.
Chelsea
That’s what we’re trying. My next email marketing campaign is brief, short Derek Sivers style emails and see how it goes. I would love to know a little bit about your writing routine, because that is something that I got really into last year, was understanding people’s routines to get a book done. There are so many people listening that want to write a book, and it feels the same as like wanting to, you know, create a movie is like, where do I even start? How do I find the time? I have 100 concepts in my head. How do I lay them out cohesively? And obviously I’m sure with experience this all gets easier. But do you have a routine? Are you like it’s book writing time? I’m not taking on any commitments. P.s. That’s what Oliver Burkeman told me. Why he didn’t want to do a podcast interview. He said, “I’m head down in book writing mode.” And I feel like that’s a lot of authors. A lot of authors routines is like, I need to say no to everything right now so I can say yes to this book. But do you have a specific way of getting your books out in the world that is like a process that you repeated?
Derek Sivers
No. In short, I just don’t. There’s no routine. There’s no habit. But I will say that for this new book, the most transformative, useful, helpful thing I did was after a year and a half of putting down everything I wanted to say onto the page. And it was not succinct. It was verbose. I had so much to say on this subject of useful, not true and bla bla bla bla bla bla bla bla bla. I was saying all of it and a year and a half of that, it just felt like, oh man, this is so far from being a book. And after a year and a half I thought, “You know what, let me just try something.” I put all that stuff aside in one folder, started a new folder, opened a little text document, and I wrote, “What time is it? For who? You? That’s not the current time right now. That’s not the current time here in New Zealand. What day is it? For who? You? I’m in New Zealand, so it’s Saturday for most of my friends in America it’s Friday. In Fiji I went to the island of Taveuni. That’s where the International Date Line crosses. There’s a sign and a line on the ground where you can put one foot in Sunday, one foot in Monday, and step back and forth across them. It reminds you that dates aren’t true. But my feet are in the sand and that’s true. When does summer begin? For who? You? For half the world, Christmas is summer time, and it’s freezing in July. This is a silly but important reminder that people speak from their own perspective. They say things like, ‘You can’t do that.’ Or, ‘Here’s what women want.’ They’re not wrong. It’s just coming from their current time zone. It might be true for them, but it doesn’t mean it’s true for anybody else.”
Derek Sivers
That’s it. Like 20 sentences. And I was like, “Ooh, that felt good.” That was one wrapped up, complete little point that could be shared in a nutshell, as is. And then I started another one about a beagle that chewed up everything, and my friend thought it was the dog, and turns out he’d been robbed. But he blamed the beagle, and it was just a nice reminder that even if there’s a stack of evidence, pointing to one thing doesn’t mean it’s true. It might still be something else. And that was a tiny little point told in 25 sentences. And I went, “Oh God, this feels so much better.” Now this thing is going. And then boom, boom, boom. After a year and a half of trying to write this book, changing the format made the rest of the book come out no problem. So it was like it got unstuck. I used a plunger, pulled out the hairball from the pipe and then everything else came out. The rest of the book came easily in the next few months.
Chelsea
Wow. I love that story because I think, again, the stories like we hear, it’s actually one that you kind of just said when the evidence all points to one thing, we just think that’s true. So we hear a lot of authors that are very intensive. I’m not speaking to anybody. I’m going to rent a cabin in the woods. I’m heads down writing seven hours a day, thousands of words, and that’s the only way to do it. And there’s a lot of people right now listening that live in a very modern society that don’t have the resources, time or freedom to block off six hours of the day and write and just ignore all prior commitments. So to hear that the format actually changed the book and it wasn’t just, “Oh, I started writing at a different time of day.” It was, “I started speaking the book into existence.” That’s incredible. I absolutely love that.
Derek Sivers
There’s a wonderful little book called “Daily Rituals” I think, that is a compilation of the creative habits of legendary artists, writers, etc. even scientists, I think. I forget the author’s name. I think it’s Mason, but he went and found through historical diaries and biographies and autobiographies how people all the way back to, I don’t know, Mozart, Leonardo da Vinci, maybe even how they would create. And he compiled them all into a book. And the takeaway from that book is there’s no right answer. Some people a lot, a lot, a lot, a lot of people, a surprising amount of people, I’d say maybe even most, had a real set routine. Like, “’Every morning at 7:00, I wake up, I get my breakfast, I read the paper.’ At 8 a.m., he went into his studio, and he would work from 8 to 12 every day. At 12, he would take a break, come out, meet with guests, but by 2 p.m. he would retire back to his studio and work until six.” It’s amazing how many legendary authors painters, artists had that kind of down to the clock hour routine. But then there are many, many examples of people that are the opposite, that just had chaotic lives, that would write when little flashes of inspiration hit on little pieces of paper, even if they’re out doing other things with friends, or maybe got all their ideas while in the salon, in conversation with the other great minds of Paris in the 1920s or whatever. There’s no right or wrong answer, so you just have to notice what works for yourself. But reading this book, “Daily Rituals” might give you some inspiration to try on habits that have worked for others.
Chelsea
I would love to read that. And I would love to read the chaotic lives, because I think that’s more in line with my speed of life. And I think hearing how other people find different routes is so, so fascinating. And yeah, I’m thinking of like the intense again, the writers that we’re talking about. I just remember there was one, it was Murakami. He like swims for an insane amount of time, and then he, like, runs for two hours. I mean, he has this whole physical activity, and then he sits down and writes for six hours, and I was like, this is so extreme. And I would love a more grounded example of someone who doesn’t have--- there’s a lot of people that also have like families and full time jobs and pets. Like we don’t have the time to just take off and run for six hours a day and then write for six hours. So I love, love, love hearing about the back winding roads that we don’t really see.
Chelsea
Something I want to talk about a little bit is business and entrepreneurship. Because you’re the only person I’ve ever come into contact with that has written the line, “I want my business to be smaller, not bigger.” Can you expand on this concept? I think this is when you started CD Baby.
Derek Sivers
I like that, “Can you expand on that?” No pun intended. No, that just comes from the tiniest bit of self-knowledge. To know what makes you happy. Even now, I’m living a wonderful life in a little crappy house in New Zealand that has almost nothing in it. I have almost no visitors. Somebody did come by a couple of weeks ago and said a sentence I’ve heard many people say in many places I’ve lived in the world, which is, “Do you live here like there’s nothing here? There’s just a desk and a chair. Are you in the process of moving?” And no, this is all I have. I’m really happy with this simple life. I do not want a staff of ten people that are depending on me. I do not want four homes and three cars or three homes and four cars. I do not want a yacht that I have to look after. I don’t want all these things. I think they would objectively make my life more complicated. There’s nothing I would do with $1 billion if you gave me $1 billion. But just give it away so I wouldn’t have to manage $1 billion. So why would I put forth any effort to go acquire something that I won’t really use?
Derek Sivers
Especially investors. I think investors are the downfall of a lot of businesses. That once you have to start pleasing investors that have no passion for the business, they just want a return on their money. And if you feel that, it would be really cool if you were to give your customers a handwritten something, something or a specially embossed this or that, or special attention or host a party where they come over and you get to meet your clients. An investor would look at that and go, “No, no, no, no, no, no. That’s that sounds like it’s taking some of my profit away. No. How about you just cut costs and double your prices and give me more return for my money?” Even if you push back, that influence is there on your business. So I didn’t even want investors. I wanted to be beholden to no one. So all these things added together meant that yeah, I didn’t want billions. I didn’t want investors. I didn’t want to be as big as possible because that sounded like a shitty life.
Chelsea
Were you always like that? Like, did you grow up like that? Or where do you think you got that viewpoint on life? Like, I’m curious more about your childhood because you seem very grounded and assured and, like, I know what I want and I know what I don’t want. Yeah, I’m just curious, what influences do you think shaped you?
Derek Sivers
No, nothing to do with childhood. I don’t know. Your question supposes that it’s odd that I think this way, but to me, it seems like anybody would think that way. That anybody who thinks that they would be happy if they had a yacht either really, really, really loves yachts and they’re correct, or more likely just hasn’t really thought it through. That owning a yacht means fucking taking care of a yacht the rest of your life. And the mold on the bottom and the circuit and the docking and the fees and the this and that. For what? Like how many hours of your week are you going to spend on this yacht? And if you’re not spending hours a week on it, then what the hell? Why would you want to own one? I think that most people just haven’t thought it through, but anybody that thought it through would come to the same conclusion. Not anybody. A lot of people, if they thought it through would come to the same conclusion I have. So I don’t think that my stance on this is so weird. I think it’s weird that more people didn’t come to this.
Chelsea
Yeah, I think my question is more of your self-assuredness when you were starting CD Baby to know investor money is not what we need. Like not what I need right now or what I want. Because I think there’s a lot of people that invest their money would look like the shiny, flashy thing, like, “Oh, this is what we need to grow. Finally, we can help more people and expand into all these countries, and we’re going to help the world.” There’s this big idea that your company, your business should, like, help so many people and save the world. And I know you’ve talked about this in your books, that you don’t actually need to help every single person that exists. And so I’m just curious, like, how did you have that foresight? Like, did you have mentors? Did you learn this from watching other people do it before? Yeah. I’m so curious about what influenced you when you were building a business.
Derek Sivers
Again, sorry, I don’t have a good answer. It feels like I just thought it through, kind of like the thing I said already. If I were to take investors, they would be demanding certain things of me. They would be adding a new criteria to this that it must make as much money as possible. And that’s not my criteria. I’m just trying to help musicians. And yes, I need to make some profit so this thing can continue. But if investors were there trying to get every bit of profit out of this that they could, for one that would feel a bit like having a boss. Fuck that. For two, that’s just not why I’m doing this. I’m not pursuing this to make as much money as possible. So then you could go to the next level. I could anticipate your next question. Well, why not make as much money as possible? Because then you think that through. And to me, that feels like hoarding. That when you see a person with a mental disorder that has either a car or a house just filled to the brim with crap, you think, “Oh, that person needs some help. They need some mental therapy help or something.” So what is it with this idea of constantly trying to get more and more and more and more money? For what? To me, it feels like hoarding.
Derek Sivers
It’s just not who or how I want to be in the world. So even when it comes to just the money, I just thought that through. It’s like, okay, well, it’s not that I don’t want anything. I really did appreciate that first million dollars. I paid off all debts, bought a home. I think with the second million dollars I paid cash for a house and everything after that was like, I don’t know. Now it’s just sitting in the bank. You couldn’t pay me to drive a Ferrari. I’d be embarrassed. I don’t want a Ferrari. And I’d be too scared that it would get dinged or nicked or stolen. It’s just not who I want to be in the world. So what are you going to do with more than $1 million? Yeah, I just thought it through like that, and I thought, “Well, sounds like it would be a lot more fun and a lot easier and a lot more meaningful and a lot more free to not answer to anybody. If I just had no investors and just kept this thing doing what’s necessary.”
Chelsea
I think that’s--
Derek Sivers
Sorry, I’m still not really answering your question. There’s no like, childhood thing or whatever. It just it just came from thinking it through.
Chelsea
Yeah, thinking it through. And it sounds like a big motivator for you, as I don’t want this to go in a direction that it was never intended to. Like you said, the investors being like, “Well, actually, we’re going to take it this way and do this, and now it’s going to add this and that and the other thing.” It’s like, “Whoa, whoa, whoa. This is not what it was meant to be. Let this be what it is, this simple, straight to the point product that I want to deliver to who it’s for. We don’t need to add 14 different features and appeal to the entire world.” It really does sound like you had the foresight to be like, let me future vision this. Like really what it is, is mapping it all out in your head. Let me future vision the different paths this could go down. And then once you got there, you’re like, “Yeah, I don’t want to go down that path.”
Derek Sivers
I haven’t read Dante’s Inferno, but I think that’s where the story comes from, of the bargain with the devil. Unless that’s “Master and Margarita”. I don’t know, but this whole idea of, like, the devil shows up and makes you an offer that, “Hey, I’m going to make you a millionaire. But take your soul in return.” And, “Hey, that’s fine. You know, I’m not using it right now.” So that’s what we call the “you made a deal with the devil” that you do get something appealing upfront. That’s how the devil made the deal with you. But there’s the trade off. And so I look at it as the devil’s bargain. And I think it’s just not worth it. I would rather have less but owe the devil nothing. Which is the same reason I’m not on any social media platforms that it might get me up front popularity, but at what price? I would have to make sure to please the algorithm. Fuck that. I’m not going to make sure my week is rotated around pleasing the algorithm just to maintain my views, to get the clicks, what the fuck is that kind of life? I do not want to live like that. Even just, you know, stories of friends that did something like bought a pixel phone from Google and then sold it on eBay, but apparently that was against the terms and conditions on buying a pixel phone from Google. And so they deleted their Google account and oh my god, suddenly their Gmail, their Google Docs, their everything was gone and they whine and cry about it, I think, “Well, you did the fucking deal with the devil.” They say, “Hey, free docs, free email.” Well, yeah, there’s a fucking trade off. They own your digital life now you’re dependent on them. What did you do? Don’t do that. Like you have to think through the implications of what you’re doing. And don’t sell your fucking soul in return for some upfront cash. So yeah, maybe I’m just a long term thinker.
Chelsea
I am nodding furiously, especially at the concept of pleasing the algorithm. If you were on my email list in the last two weeks when I was going through this course launch, the whole thing is about being a guest on podcasts and how it can actually help free you of the algorithm, because you get to have conversations like we’re having now, not have to worry about an algorithm and stay up to date. And someone, as I was talking about this goes, “Oh, have you read Mark Groves’s email about leaving Instagram?” And I’m like, “No, I haven’t.” And apparently he made this point of like, why would I continue to invest in a one sided relationship that is toxic, that technically abuses me because it penalizes me if I don’t post every day three times a day and then it stops showing my content to followers that opted in to following me. It’s like if that was a person that would be a terrible relationship, and then just staying in it over and over again is like saying, “I’m totally okay with it. I have such low standards and no self-esteem.” But somehow we allow that when it comes to digital platforms like social media or things that own us, we’re like, “Oh, it’s okay.”
Chelsea
And it kind of reminds me of what we’re talking about, of like, I’ll sell my soul for the views, the visibility, whatever it is. Instead of thinking, “What if this platform shut down tomorrow? Where are all those videos going? Where’s all that copy going?” And it brings me to a question about your site. Your site is the only one I know that is so custom built where it’s all like, you know, we were talking even about this video today where you’re like, “I just want this, to own it and have it in my own archive.” And it’s not about, “Oh, I’m going to go post this on my blog and I want everyone to see it.” It’s like, I want this for myself. I don’t think a lot of people understand the control that digital platforms like social media or Gmail or anything, the cloud we were talking about earlier. I don’t know that a lot of people grasp that. So can you talk us through how you built your website and why this is so important to own your intellectual property?
Derek Sivers
I feel a bit like the old man, or let’s say, the old couple that has a little cabin somewhere, and then a big suburb or big city develops around that cabin and they start building skyscrapers around it. But you’re still just doing the same thing, like you don’t sell your land to them. And so you’ve just been doing the same thing for 50 years. Everything I’m doing on my website is completely normal for everyone that had a website in the mid 90s. It was the absolute norm. There was no social media then. If you wanted to be online, you started a website, or maybe there were some services that would give you kind of like user accounts on their website. But for the most part, if you wanted to get online in the mid 90s, you built a website, you learn a little HTML. It’s not that hard. It takes you a couple of hours to learn HTML. The opening tag and bracket HTML, close bracket, head title, body h1, title of my page paragraph tag, “Hi everybody. Blah blah blah blah.” New paragraph tag. Close paragraph tag. Close body, close HTML, send. Save it as index.html. Upload it to a public server. Point a domain name at that server.
Derek Sivers
There you go. You now have a website, and everything after that is just incremental improvements. If you want to have people interact with your website, well, then you have a little JavaScript on it that you can also learn in a few hours. There you go. If you want to share files with people, you don’t need Dropbox to do it for you. You just upload it to your website. Give people the link. Here’s the link to download my files. If you want to have calendars, contacts, even your own email server, it’ll take you a couple hours to figure out how to set up your own email server. So it’s, you know, chelsea@chelsearules.com or whatever. It’s now your mail server and any mail sent to it just goes directly to your server and you can either reply from the server or download it into your phone or an app and just reply. You don’t need Gmail. You don’t need any of that. You’ve just got your own server. It’s fine. This is how the internet was built, was a decentralised network of servers. But of course there’s a massive financial incentive for businesses to convince you that it is much too hard for you to do it yourself.
Derek Sivers
“Oh, you sweet, poor little thing. No, no, no, you don’t worry about this. You get back to your life. We’ll take care of your digital life for you. Just give us all of your data. Keep it all with us. We’ll take care of it for you for $10 a month.” Sorry. Now it’s $39.99 a month for the rest of your life. “We’ll manage it for you so that you don’t have to. It’s very complicated. You couldn’t handle it. Trust us. We’ll manage this for you.” They make billions of dollars convincing you that it’s too complicated for you to do yourself. But it’s not. It takes a few hours to figure out. And it’s a deep joy of self-reliance to just figure out how to do these things yourself on a server that you can literally just put in your closet. You could have a $20 computer connected with an Ethernet cable to your fiber whatever modem and have that open to the world. Or if you don’t feel like having people connecting to a computer in your closet, there are places that for $5 a month, will just give you a generic Linux server that you can just install any software on and just run it publicly.
Derek Sivers
That’s not even the cloud, you know, that server is sitting in Dallas or that server is sitting in Amsterdam and you’re paying them the $5 a month, and you have a domain name which costs you maybe $10 a year to have, you know, www.chelsea.rocks or whatever. And you pointed to that server and that’s it. You own it and nobody can de-platform you. Nobody can remove you from the algorithm because you’re just not depending on it. And there are so many of these services that I said, like Dropbox, for example, that offer a service that you just don’t need. It’s basically server 101 to just synchronize your files to your server and keep it on a public place so that another device, whether it’s another person or your phone, can access them from your server. That’s server 101. That’s like the very first thing you learn. And so my jaw dropped when I saw that Dropbox was saying, “No, no, no, no, we’ll do it for you.” For $10 a month or whatever, I think, oh God, if people only knew they don’t need any of this.
Chelsea
And yeah, I think most people listening, don’t even realize that. They don’t even realize that these platforms own your data or have such easy access to it, or that you could actually build it yourself. And I think the other part of the group is probably like, “I do not have time to learn coding and programming and building and this and that.” And it does seem overwhelming. Right. And also my brain goes to digital nomad brain of I can’t travel with a computer and a cord and all these other things that are going to be hooked up. And I’m curious your advice on that.
Derek Sivers
Well I do pay the $5 a month to a company. I have a server sitting in new Jersey for $5 a month, that when you connect to my sive.rs. Actually I have like 20 websites hosted on there. I have various things. I have a translation service called Inchword. I have now nownownow.com, musicnotes.com where I’ve collected a bunch of inspiring quotes about music. I have like 20 different websites hosted on there for $5 a month. It has all my files, my backup, my calendars, my email, or whatever. I don’t use any video streaming. All of this from a little $5 a month server that sits in New Jersey so I can sit wherever, or if the company in New Jersey suddenly decided to start charging $100 a month, I’d just move it to a different company, just point my domain to the new company, and you’re not bound because you’re not using, you know, chelsea@gmail.com. It’s always d@sivers. So wherever I decide to point my website, my mail, I can point it to any new mail server and I just point my domain to the new server, so you’re never bound to any one business. Never give people a URL that contains another company’s name in it. You know, instagram.com./me. Well, then, if you’ve given that address to everybody and Instagram deletes your account, you’re fucked, you know? But if you only give people the me.com URL. Sorry by that I mean your own URL. Then you’re never bound.
Derek Sivers
You’re never stuck with any company. You can just move it. It’s just a generic service that thousands of companies offer this little Linux web server hosting that you can do anywhere. Was there a bigger point? My bigger point is that you said something like, “Your website is the only one I’ve seen that...” But again, this stuff was totally normal in the 90s and kind of like the person with the cabin that’s had the skyscrapers grew around me. I’ve just been doing things the same way since then, I feel no need to partake in these services that have popped up. Oh, sorry. I know the other thing you brought up. You said most people don’t have time. But to me, that’s a little bit like I don’t have time to learn how to drive a car. So I’m just going to depend on Ubers for the rest of my life, or I don’t have time to learn how to make a sandwich. So I’m just going to buy sandwiches for the rest of my life, etc. you could figure out more examples of this. You just put in a little upfront time, especially if you’re young and voila, you are now self-reliant for the rest of your life. You’re saving yourself thousands of hours and tens of thousands of dollars in the future to just spend a few hours of your life up front to just figure out a little basic HTML, set up a server. Look at that. You’re done.
Chelsea
Okay, I’m feeling motivated. I feel like this is a project I need to put on my 2024 list. Because I think the more and more these algorithms pop up, the cloud. I just read something about another data leak from another online platform that happened that, you know, promised it would never happen. I’m actually watching right now. So random, Ashley Madison, do you know who what this service is?
Derek Sivers
I remember that from years ago.
Chelsea
Yeah, it’s insane. It’s where married couples could go to have affairs. And the whole thing was based on, “We keep your information private and secretive and da da da.” And then it came out that all the little awards that they had on their homepage that were, you know, like secure certification were all like, photoshopped by their team. That wasn’t real at all. And then someone hacked them and they released every single person that had signed up for this website. It destroyed marriages. It destroyed people’s lives. There were few people that actually took their lives because it was meant to be kept secret. And yeah, I just watched this documentary the other night and brought up this whole idea of, like, data privacy and how when you give your credit card information and data away, it doesn’t always mean it’s safe.
Derek Sivers
Well, I could see somebody saying in that scenario like, “Well, what did you expect? You shouldn’t have been cheating.” But the story that hit home for me more was a good friend of mine in Singapore that was very tech savvy. He was a tech investor. He was a VC tech investor, investing in tech startups in Singapore, super tech savvy, so tech savvy that when he and his wife had a baby, he decided from the start we were keeping all of the photos in the cloud. We’re going to use the Google Photos to share it with the whole family. We’re doing things the new way here. Living in the future. And so for, like, 11 years of their kids life, all of his life’s things were all stored in Google Photos. He trusted Google. And then he started a new business one day and signed up for, like, Google Apps for business. And it said something when he signed up, you know, “Do you want your new account or do you want to merge?” Yeah. Okay. Yep. Okay. Click. All right, great. And he starts his new company and he’s using Google apps for business. And then like a day or two later, his wife said, “Honey, where’s all the photos of our kid?” And he goes, “It’s on Google Photos. Like it should be.”
Derek Sivers
She goes, “No, it’s not.” And he looked and it’s like the Google Photos account was empty. And he’s like, “What the hell?” And he contacted customer service and they said, “Well, yeah. When you clicked to sign up for new business, we asked if you wanted to merge the accounts and we and you clicked to approve this thing. And so your Google photos are gone.” He said, “Okay, well can you please put them back?” And they said, “No, they’re they’re gone. You clicked.” He said, “Well, I didn’t realize I clicked that you must have a backup.” They said, “No, you you must have a backup.” He said, “No, I kept my photos here.” Just like that there are literally no photos or videos of his kid from the age of 0 to 11, because he trusted to keep them in Google. And to me, that’s just again, it’s like, “Well, dude, come on, the cloud, clouds go away. Like, that’s what they do. They pass, they disappear.” You know what? Oh, God. You know, so yeah, I never put anything of any importance in the cloud.
Derek Sivers
Nothing of any importance in my phone. No, I only trust my own computer backups, which are kept on, like five hard drives in five countries in the world. And I know that’s a little extreme, but even just having, like a USB stick that you plug into your computer, Even like my photos on my phone. Every week or two, I just plug in the cable onto my phone, transfer all the photos off to my computer, save them as JPEGs, put them in my computer file system that’s backed up to five places. I just assume that my phone’s going to get stolen. Every cloud company will go out of business. I just don’t depend on any of it. And I know I’m a little extreme with that. So you pick your own balance. But look, I mean, the number one lesson is this stuff is not that hard. As if riding a bike was suddenly really rare, or driving a car was suddenly really rare, and most people didn’t know how to do it. And they’d say, “Wow, driving your own car, but you could just call Uber for the rest of your life.” And you just put in a few hours and you just learn it.
Chelsea
It’s so true. And if you think about it, driving a car is insane. Like it’s a machine that moves at whatever speed, dependent on a ball of our foot. Like when you actually break down, you’re driving a car is. It’s pretty crazy. And we’ve all somehow figured that out.
Derek Sivers
So to close out this subject, by the way, wait before we let it go. So I did end up putting everything I’ve learned into a simple tutorial. It’s at sive.rs./ti which stands for Tech Independence. So go to my guide there and it just walks you through step by step. And it’s basically just, “Do this. Tick. Tick. Tick. Follow these steps. You’ll have a live server with web, email, calendars, contacts.” And more I’m forgetting.
Chelsea
Okay. We are linking that in the show notes. 100%. Thank you for that. I want to talk a little bit about the utopia that you talked about, and I think it was “Anything You Want” of how your business gets to be a utopia where you control the laws. You are the person that builds what you want. And it reminds me of another book that said this. I don’t remember the name of the book right now, but it was something like, “Your business can be an archetype of the utopia you want to see in the world.” And between your example and this other books example, I remember thinking that of like, well, if I want a space where people are not working at breakneck speed and trying to do things, you know, ideas by Monday, execute it by Friday, I can build that. If I want a business that’s more heavily focused on audio interviews versus being on social media all the time, I can build that. And that concept has really, really stuck with me and something that I really integrate. And I’m curious in your so many years of experience with CD Baby, with writing, with all the stuff you’ve done in your past, like how have you not only made your utopia, but kept it up when there is pressure to maybe pivot or do something else? So what I mean by that is, external influences pop up that might seem more appealing. Essentially the question is, how do you maintain your boundaries around keeping your utopia running?
Derek Sivers
What kind of pressure from others can you think of an example?
Chelsea
I think a good example would probably be maybe your audience is like, I actually love when you do this thing versus something else, like let’s use this example. I like when you write your Substack posts versus your podcast, but I love doing my podcasts, and my podcast is like my baby, and it’s something I want to keep up for the rest of my life. It doesn’t really make me money. It’s a form of expression for me. It kind of ties to my business. But if my audience was constantly like, “Hey, we read your Substack more, we read your Substack.” And I was getting all this feedback. I might be like, “Okay, I might have to change up the business model a little bit.” So I don’t know if that’s the best example, but I’m trying to think of one that people feel pressure from is like their own consumers or clients.
Derek Sivers
I could probably blather on about this for a long time, but I think the most important point is something we talked about maybe an hour ago, which is intrinsic motivation, being like the oil in the machine, that if you’re not intrinsically driven, personally fascinated and excited about this, then it’s going to feel like a machine without oil. It’s going to be a grind. There’s going to be friction and rust. It’s going to be hard. But whatever you’re intrinsically driven and motivated to do is just going to flow smooth and feel easy and also just make you proud of yourself, make you feel better about being you every morning. The example I’m thinking of now is my book covers that I spent hundreds of hours trying to find the right book cover. Knowing I was going to be doing many books in the future, knowing I had at least five books in me before I did that very first one I thought, “I want the covers to be all related, so I want a style of cover that could apply to all of my books, so that you could have them together as a collection and see how they’re all similar.” Maybe that means that they all have a different color scheme, like there’s a series of books from Oxford University Press called “Very Short Introductions”, where every cover is kind of like an interesting blurred collage of colors, but each one is a different one. Or I’ve seen Richard Dawkins has a whole series of books that were rereleased where everyone has like a very simple line drawing across the cover that matches the theme of that book.
Derek Sivers
And I’ve seen some other examples like this, and I sweated over finding the right cover design. I hired maybe five different designers over a year and a half to do their best proposals. I even did like a 99 design contest. Where something like 50 different designs were submitted. And then I picked the best two designers of those and they battled it out. And in the end, I found that when I went to a friend’s house and I saw that she had an old bookshelf with some like old 1950s books on them that were probably originally--- had a dust jacket on the outside, but now all that was left was the raw bare book that was just like the cardboard hardcover and with a fabric cover and the name written on it. Just the title and the author. No photos, no blurbs, no art, just the title and the author. And I remember I looked at this and went, “God damn, that is badass.” A book that just has the title and the author, and no pretty pictures beckoning to you with some flashy marketing is just so fucking confident. It’s just like, Yeah, just read it. The words inside this book are powerful enough that I don’t need to splash some flash on it.” In fact, that would diminish it.
Derek Sivers
And so I just noticed that’s how I felt. And I thought, you know what, I would just be prouder of books that were just the bare hardcover without the outside dust jacket with the flash and went, “Huh? I think some people will be disappointed in this, but I’ll feel great about this.” That makes me prouder of my books to say, oh, here hold on. I have on. Yeah there we go. To say, like, “Look at this. Just the bare linen fabric hardcover. No picture of the author, no blurb on the back, no marketing slogan, just the title and the author.” I was like, damn, that’s badass. I just feel better about it. So same thing with any decision you’re making about your business. There are ways you could structure it that would make you prouder that even if it means a little less income you’ll feel better about yourself. Artisan shops are like this. Maybe it’s looking at the example of boutique artisan shops. They’re doing something in very high quality because they care really passionately about it. It’s a different standard. They’re doing it to make themselves happy first and to make the aficionados happy next. And anybody else can get stuffed, as they say, if you want it as is, take it if you want it. If you’re not willing to play by my rules, get out. There’s plenty of other businesses that will serve you. This is how I feel like being.
Chelsea
I love that. I feel like that is so key for entrepreneurs to hear, anyone entrepreneurs, creatives, new business owners because we are very influenced by what we see online and, “Oh well, this person had this branding and it did really well in terms of clicks or views or money. And so maybe I should model my branding like that, even though I would never really use those colors.” You know, and we just get so muddled and we forget what even lights us up. I feel like that’s something that has come up a lot in this conversation, is feeling into it. I feel like you’re someone who feels into it. Does this feel good? Does this light me up? Like it seems like you have a very strong connection to your body and like your body’s wisdom, would you agree or what? What do you think about that?
Derek Sivers
I don’t even think it’s that. It’s just that happiness in the broad sense, whether it’s fulfillment or whatever you want to call it, is the real point anyway. Even if you say that you want more money, you want more money because you think it’ll make you happier. If you say you want more freedom, it’s because you think it’ll make you happier. So ultimately you just go directly for the real point anyway, instead of selling your soul to make more money so that in the future, after selling your soul and doing some shit you’re embarrassed of, you can get more money, so then you can be happier. Instead, you just ask yourself, “Well, what would make me happier to go directly for?” And you just do that instead. Look it’s different for everybody. It was interesting reading Richard Branson’s autobiography, where he had $1 billion and just found it fun to go try to make another billion. That’s what sparked his joy and made the day worth living. And some of my friends are very rich now and have way more money than me. And I’d say half of them are happy about that and half of them are not. Half of them are pretty miserable, and they say that they’re jealous of my life, of freedom with my tiny, shitty house and no obligations and no employees. But some of them are thrilled and like, waking up and trying to make another $100,000 this month or today excites the hell out of them and drives them. So it’s not even like, as sensitive as being in touch with your body. I mean, unless that’s what it is for you. But I think it just takes a little foresight and planning to say, “Well, what do I really want? And what’s the most direct way to get there?
Chelsea
I love that. I feel like we could talk for another eight hours, but we’ve already talked for almost three. So I would love to just ask a few final questions. And I think confidence is something that creatives struggle with when it comes to putting out their work. “I don’t want negative feedback. I don’t want people to think this is shitty. I don’t want bad reviews on my book. I don’t want people leaving one star ratings on this podcast.” And there’s a lack of confidence that comes out with saying, you know what? I’m just going to do it. I’m going to put it forward. If it comes, it comes and and we’ll deal with it. But I’m curious about your journey with negative feedback. Has that happened? Has the worst nightmare of, “This sucks. Can’t believe you put this out. One star review.” Has that ever happened to you and how did you deal with it? And on the flip side of that, what are some ways that we can start to build confidence around our work if we’re not feeling it?
Derek Sivers
I went to music school. I didn’t go to a normal university. I went to Berklee College of Music, where for all those years that most people are in normal universities, I was doing nothing but music. And one of them was a songwriting workshop where you would write and record a song, no matter how rough it is, even if it’s just you sitting on the bed with an acoustic guitar, singing into a little recorder. Then you’d bring it into an anonymous workshop where there would be a room of, say, like ten kids, whatever, teenagers, students, and one teacher up front. That would then take the recording and play it and the whole room would sit and listen. And one of them would be your song. But then nine wouldn’t, but they wouldn’t say who this is. You would just listen anonymously and then people would give critique on it. They’d say, “That first verse went on way too long, you know? It should have been cut in half. The bridge totally lost me. I really liked where the first verse and chorus were going, and as soon as it went to the bridge, I thought that was unnecessary. It would have been tighter here. Loved this lyric. Hated that lyric. I think you’re staying in this register for too long with the melody.” And you’d get this critique that when it was your song, you’d go like, “Ah, fuck. Like I thought it was a good song, but I totally disagree with that guy. I like the melody being up in that register, but this woman had a good point that I think she’s right. The bridge is not working.”
Derek Sivers
So you take the feedback and you detach from it a little bit. The fact that it was anonymous really helped that you knew it wasn’t somebody attacking your existence on Earth. It was somebody trying to improve your song, and then vice versa. Another song would come up and then you’d be one of the nine people listening to somebody else’s song, giving feedback about what does and doesn’t work. That process was so useful to help you detach from your work, to know that you’re just putting something out into the world. You want it to be good. You want people to like it. You want to be proud of it yourself, or just for it to be objectively beautiful. Which, by the way, something, you know, going back two hours about my writing, it’s something I think about a lot with “How to Live” and my new book, “Useful Not True”, is like I’m trying to make it beautiful, which is just just objectively, whatever that is, that aesthetic. I think like, “Oh God, that’s a beautiful phrase or that’s a beautiful point.” So no matter what it is you’re making, you want it to be good. And when people give you critique on it and they say like, “What? That’s stupid. You’re an idiot for saying that. That’s totally wrong. Or this format sucks. This interview went on way too long.”
Derek Sivers
You don’t take that as an attack on Chelsea. It’s just like, all right, so I’m getting some feedback that people, no matter what words they say, even if they say you’re an idiot, people like you are the problem with the world. What they’re really just saying is, I don’t like that format or I think you missed the point there. So that’s one. So it’s detached from your public persona. I wish that we all had a stage name. I think it’s really handy that Paul Hewson from Ireland gave himself the name Bono so that if somebody is attacking Bono, saying Bono is full of himself, what an egotist, then Paul Hewson can go, “Yeah, he is, isn’t he? You know, that’s my public persona. He is quite an egotist.” It’s that separation between your private self and the things you’re putting out into the world. A stage name would really benefit all of us. For some of us, it’s too late. But like, for example, my kid, I’m going to highly recommend that he never use his real name publicly online and just use the stage name to help keep that separation, to know that the public attacks on what he’s putting out into the world are just attacking the thing he’s creating, which is just feedback. Wait, you had a second half to that question. Hold on.
Chelsea
Building confidence. Yeah. Building confidence.
Derek Sivers
Oh no. Wait, but these were two. These were related, I just remembered. Thank you. The second half of this is to also know that it’s human nature to know that it’s like one of those popular cognitive biases that we all fall prey to. When you learn about, say, you know, loss avoidance bias or whatever. If there are 100 positive comments on your YouTube video and one negative one, you’ll look at 100 comments, you go, “Oh yeah, that’s nice. That’s oh, that’s really sweet of them.” And you see the negative one, you go, “Hey, what the hell? Yeah, what the hell is this? What an asshole.” Like, we can’t help it. It’s human nature to focus on the one negative among the many positives. So also just recognizing that’s your nature, I think helps you discount it, so I still get that on my own blog. Most of the comments are nice. Every now and then I get a nasty one and I still catch myself going, “Hey, what the hell?” And then I’m just like, “You know what? The other 99 were great. Whatever. Can’t please everybody.”
Chelsea
And I always tell people this too. Imagine if you tried to appeal to the negative commenter that was like, “This blog sucks. Can you change it up?” And then you’re like, okay, yeah, now I’m going to appeal to this guy. And then the other 99% are going to be like, “Wait, what happened? We loved your old way of doing it.” And you have to eventually pick a lane and stick to it and understand majority like this way.
Derek Sivers
And maybe that’s what I liked also about the anonymous song critique is that sometimes people give feedback and they’re really just stating their preference, saying, “I would prefer it this way.” And you can listen to everybody and then some of them you just disagree with. You go like, nope. You know, somebody might tell you that your writing should be more succinct and you could be like, “Nope. I like it like this. And that’s okay.”
Chelsea
Very true. Love that. I had the other question about confidence because again, I think confidence is just something that can be rocked really easily, especially on the age of online social media that people depend on so much is, people start to see confidence elsewhere of, “How many likes did this get? How many replies did this email get? How many click through? What is my click through rate on this?” And it’s all so tied. We base a lot of our worth on the external metrics, validations, feedback instead of finding that internal confidence. So I would love to hear whether that’s like a tip, a trick, a mindset shift, something that has helped you be so confident in your work.
Derek Sivers
I think the most important thing is to realize that it’s not about you. That you personally don’t matter to hardly anyone. If somebody is reading something you’ve written and they like it, it doesn’t mean they like you. They just like it. They like that point so that they can selfishly apply that to their own life. They like it for selfish reasons, because they can use that. And if you put something out into the world that you liked that other people don’t like, well then all they’re saying is from their own selfish point of view, for whatever is going on in their lives at this time that wasn’t useful to them. It had nothing to do with you. It’s a cute story. My kid is not a natural musician, so don’t get the wrong idea from this next story I’m about to tell. But when he was four years old, we went out to the beach and he was playing in a tide pool, and I was recording him because we were looking for a crab. And so I hit record on a video, just in case he found the crab. I wanted to capture that moment, and he made up a song in the spot that I know him very well. I’m around him all the time. I know he did not hear this song and did not get it from anywhere else. He came up with a little song that went, and I have this on recording. He just started singing out of the blue, “Everything’s okay if you don’t matter, everything’s okay if you don’t matter.” And my jaw dropped, I went, “What was it? Where did you get that?” He goes, “I don’t know, just made it up.” I went, “Oh my God, that’s brilliant. Everything’s okay if you don’t matter.”
Chelsea
Wow.
Derek Sivers
And I think about people who tell me that they have imposter syndrome and I can’t relate. I do not understand imposter syndrome. And you’re the first person, sorry, second person I’m telling this to. So I’d be curious to hear your thoughts on this, but I think imposter syndrome comes from thinking that you matter, that it comes from assuming that people are thinking of you and judging you. Whereas maybe this whole time I’ve just assumed that I don’t matter for shit in people’s lives. They’re just using my books and using my little articles and using my podcast or whatever to benefit their own selfish lives and don’t really give a shit about me. None of this is about me. I don’t matter, I’m just putting shit out into the world that maybe you find useful. Maybe you don’t. Sometimes I do it just because it makes me happy. The way that people paint their house, they’re not doing it for their neighbors. They’re doing it because they want to live in a green house or a yellow house. It makes them happy. And sometimes I just put things out into the world because it just makes me happy. I want to do that. And other times I am putting things out into the world for other people, and they say they like it or they don’t like it. And I never think that any of that has to do with me. So I think that might be the antidote for imposter syndrome, is this deep felt belief that you don’t matter.
Chelsea
Your son’s song. We need to turn into a public track so we can hear it over and over again. And what you’re talking about reminds me a lot of archetype embodiment. Have you heard of this concept?
Derek Sivers
Mhm.
Chelsea
Where you basically imagine I’m feeling not too confident in my creations right now. And so basically I call it picking a video game character. Like when you get on a video game and you get to pick the fighter or the princess or this or that, and then you’re like, “I’m going to become that character.” So what would the creative genius do? What would the spellbinding copywriter do? And then you just start to take steps to act like them. So then you have this kind of archetypal protection to you, it’s kind of what you’re talking about is, “It’s not me, Chelsea Riffe, that you’re attacking about my intelligence.” It’s actually when I was the creative genius, I put out this entity of work that has its own special orbit. That might be the thing you’re giving an opinion on. Not me, per se. So I think I like to call it trying on a different video game character. So whenever I feel like I don’t know if I can do this. Last year I had one called “The Bitchy Magazine Editor” when I launched my Substack, and I was like, “What would a New York bitchy magazine editor say about this? And how can I become this and just get the articles out, start writing?” And then I put her away, and then I try on a new video game character of, I want to be the poet, you know what I mean? And so I think essentially we’re talking about the same thing just using different languages, but it goes back to the stage name. A stage name and a pen name are archetypes. They’re different video game characters that people got to be. And then, you know, kind of take off the mask and and then enjoy Chelsea Riffe and Derek Sivers as just people, not the art that they’re putting out like these different entities that are floating around. That’s kind of how I think about it.
Derek Sivers
Nice. I like that a lot. Yeah. There’s a wonderful book about this called “Alter Ego Effect” by Todd Herman, where he mostly worked with athletes, but a lot of athletes, backstage boxers, football players or whatever are in the locker room about to go out and they’re just like, “All right, all right, here comes the tiger. You know, the tiger’s coming out. Here comes the tiger. The tiger’s going out on the field.” They’re not being, you know, Jeffrey Benkenstein they’re being the tiger. And that can be so useful even if you’re just sitting alone, being a writer.
Chelsea
I love that. My final question that I ask every single guest on this podcast is this podcast is called, “In my non-expert opinion”. So what is something that you’re not an expert in that you wish that you were
Derek Sivers
Sorry I overthink these things, but...
Chelsea
I was like, I’m sure you have a very interesting answer and I can’t wait to hear.
Derek Sivers
Well, what’s the point of an expert is that for my own ego to say, “I am now officially an expert in the subject of Russian literature.” Is it to impress upon others so I can, “Look at me, I have a PhD. I’m now an expert in this thing.” Or is it for the end result? It’s a means to an end. Expertise is a means to an end, but often the end doesn’t necessarily need expertise. That I am quite good in the Ruby programming language and quite good in the PostgreSQL database programming language. I don’t know if I’d really call myself an expert in either one, maybe by some people’s definitions, but definitely not by others, but I know enough to do anything I want to do. Anything I want to make happen, I can do with a combination of Ruby and PostgreSQL. I can make any web app, I can make any whatever. I can make my data do whatever I want. I can make a computer do whatever I want with those two tools. But I’m still probably not an expert, but who cares? Because I’ve got the skills to do what I need to do. Writing. I wouldn’t say I’m a writing expert. I’d probably be terrible working for a newspaper or some kind of media outlet that’s like, “Bang, bang, bang. Come on, Derek, we need a thousand words or we need 10,000 words on this subject by tomorrow.” I’d probably be really bad at that. I’d probably be really bad at most kinds of writing, but I’m good at my little kind of writing. So I do not want to be an expert in anything.
Chelsea
I love that. You are the first guest who has ever said that, and I feel like that just completely puts a cherry on top of the person you are, and I appreciate who you are so much. So thank you.
Derek Sivers
There is a Sinead O’Connor album titled long ago called “I Do Not Want What I Haven’t Got”. And that one really stuck with me and I think about that a lot. I was even thinking about it yesterday. I do not want what I haven’t got. I really like that, I agree with that statement. Yeah. I do not want what I haven’t got. I like that a lot.
Chelsea
I love that. Well, I think that’s...
Derek Sivers
Even expertise.
Chelsea
Yeah, right. I know you have “Useful Not True” in beta. Do you have a date of when that might be released?
Derek Sivers
No, soon. Very soon.
Derek Sivers
Like your earlier question. I can tell that the effort I’m putting into it is making very, very, very minor improvements at this point. So I feel that I’m probably in the last week or two of writing it, of editing and changing it, and then I’m just going to send it off to the printer and that takes a few months. So yeah, probably by the time this is published, anybody my books are only on sivers.com. Any time I release a book, I keep it only on my own website for the first year, and only after a year or so do I put it on Amazon. And the rest because fuck them. So I got my own. I don’t need your stupid platform. Go to sivers.com. All my books are there.
Chelsea
Love that. And that’s where we can find everything. Your wisdom, your writing, your “About Me” page, which is my favorite page on the internet. About me in 10s. About me in ten minutes.
Chelsea
I constantly refer people to that. So thank you Derek. This has been such an incredible conversation and I’m so, so appreciative of you coming on.
Derek Sivers
Thank you.
Derek Sivers
Thanks, Chelsea.