Interviews → Jeremy Ryan Slate / Create Your Own Life

Jeremy:

This is the Create Your Own Life Show where we interview people that are world-class performers from Super Bowl champions to New York Times bestsellers to billionaires. We figure out what makes them tick and unpack it for you to do the same. I’m Jeremy Ryan Slate and every Monday, Wednesday, and Friday, we help you to create your own life.

What is up everybody? Jeremy here, and welcome to Episode 645 of the Create Your Own Life Show. I’ve got to tell you guys, I am very, very excited for today’s guest. We have Derek Sivers with us today. He is the founder of CD Baby and he’s since moved on from that. He’s working on a number of different projects. He’s also given a TED Talk on the idea of movements, which I really recommend if you haven’t seen that to check that out.

He’s also one of the original figures mentioned in The 4-Hour Work Week as well. So, somebody that I’ve been looking forward to interviewing for a long, long time. If you guys remember the list of people I most admire that I put together when I wanted to put together this show – Derek was one of those 100 people I reached out to. Now, almost five years down the road, the interview has finally happened, and I have to tell you guys, this is an incredible interview.

We don’t really talk about building a business. We talk about living in a culture outside of your own and how that perception can change your perception and change your worldview. We look at Stoic philosophy and how Derek applies that in his life. We look at the idea of journaling and how that’s had a huge effect on Derek’s life, and his very different idea on what he would write on his tombstone and what he would actually do with that. So guys, you do not want to miss this interview.

Without further ado, let’s get into this interview with Derek Sivers.

Welcome to The Create Your Own Life Show, Derek Sivers.

Derek:

Thanks Jeremy. Hi!

Jeremy:

I’m really stoked to be chatting to you, Derek. So, we are in 2019. I started this show in early 2015. You may not know this, but my audience knows that I created a list of the top 100 people that I most admired, and reached out to them. You are on that list, and every couple of years, we’ve had emails back and forth but the timing wasn’t right, and I guess finally I hit you with the right set of questions, and here we are.

Derek:

Yeah. I’m at a place in my career where I’ve got nothing to promote. I don’t want or need the attention, and I got a little burnt out on doing interviews because I found that at this stage in my life, I don’t want to be the guy that has all the answers. I want to be the guy that has all the questions, but yet I’m not going to go host my own podcast. So I just found that doing most of the interviews was not really worth my time.

But I really admire what you’re doing and you sent me over some really cool subjects to discuss, so I’m looking forward to this.

Jeremy:

Absolutely. You came on my radar way back when I read The 4-Hour Work Week in 2007 as Tim Ferriss spends a little bit of time talking about you, and then I’ve listened to various interviews about you. From founding CD Baby to moving on from that to being a clown for a bit – a performer yourself.

Now, a lot of what you do is choosing the cultures that you live in.

Not too long ago you sent out an email to your list and you’re basically like, “Hey, I’m moving to Oxford if anybody knows anything about the area.” Why do you choose to live in certain places? And how has culture and perception of culture changed your viewpoint of the world? That was a very loaded question.

Derek:

It’s one of my favorite subjects. Well first, I need to give some context.

Jeremy:

Sure.

Derek:

Fifteen years ago I was living on the beach in Santa Monica, California, and life was perfect. I mean, absolutely perfect. I was in heaven. My girlfriend of six years was from Sweden and she wanted to travel the world, and I said, “No way are you crazy? We’re in paradise. Why go anywhere else? I mean, what do you expect to find, a better beach? I mean, come on, this is it. This is the end of the rainbow. We already live in the best place in the world. Why would you want to travel?”

Shortly after that, we broke up, but not for that reason.

Jeremy:

Well, it wouldn’t be a bad reason though either [laughs].

Derek:

Actually, it was a wonderful relationship that came to its natural end. It was not to derail the story, but it was actually the best breakup I’ve ever had. We were together for six and a half years. We went out to a movie and after the movie we just kind of looked at each other and said, “Do you want to break up?”

“Yeah, we think it’s about time. Let’s break up.” We just went our separate ways. It was perfect.

Anyway, I went up to Portland, Oregon to run my company. A year later, I sold the company and suddenly I was 100% free to do anything and go anywhere. I had no responsibilities. That’s when I started thinking about what matters to me most in life, and my ultimate top value is learning and creating. The combination of the two, and learning for the sake of creating, creating for the sake of learning. There’s probably a long German word that encompasses both of those, but until then we’ll just say learning and creating.

Jeremy:

I was having a conversation a week ago. There’s a part in the dashboard of a Volkswagen and in German, I don’t know what it is, but it’s basically the thing that goes into the thing that goes into the thing, so I get it [laughs].

Derek:

Awesome. I love it [laughs].

So I realized that to keep growing intellectually, I need to keep being surprised. The danger, especially when you’re over 30 is that you can get into a rut. I think a lot of us when we’re teenagers and when we’re in our twenties, we grow and change all the time, and then people get into their thirties and it’s just kinda like, yeah, well this is me. This is who I am. Here’s my sports team. Here’s how I like my eggs. This is where I live.

So I wanted to keep being surprised because I think if we’re not surprised, we’re not really learning. Yes, we may add some new information – some more facts. But, unless you’re surprised, you’re not really changing the way you think, right? It’s only when you come across something that kind of makes you gasp and you go, “Oh my god, I never thought about it that way. That’s…oh my god, that’s a different way of thinking.”

That’s when you’re really learning – not when you’re just adding some more information in your head.

Jeremy:

I totally agree with that, man. Because it makes you have to either look at something the total opposite of how you looked at it or at least create a solution you didn’t even think of.

Derek:

Right? So yes, of course I could have sat there in Santa Monica, and I could have read books, and I could have found surprise in that. But I think we can all shape our environment to be the most conducive for what we really want. To me, I felt that the environment that would be the most conducive to constantly keeping me surprised and keeping me growing and learning would be to hit the road and live in places that are very uncomfortable to me.

Places that are full of surprises. Places that are nowhere like where I grew up. Places that have values very different from the ones I know. A place that does things differently. Because to me, places kind of have a living philosophy. There’s a philosophy of Thailand. There’s a philosophy of Finland. They’re kind of like applied philosophies.

So I set off into the world with that goal. I wanted to live somewhere and fully integrate until this place feels like home, and then move somewhere else and do it again.

Did you by any chance see the movie Big Fish?

Jeremy:

I did. It was a long time ago though, so I don’t quite remember the plot.

Derek:

I barely remember it. But at the very beginning, who is the guy that played Obi-Wan Kenobi in the reboot?

Jeremy:

Ewan McGregor.

Derek:

Okay, he was the lead character, and he sets off on this journey. He has a thick Mississippi accent. He says, “I just want to go see the world.”

When he first sets off, he comes across this jungle, and inside the jungle is this paradise. Everybody’s incredibly happy and life is perfect. Everybody there loves him, and they’re just like, “Come stay. You should stay here.”

He’s tempted for about a day, and then he says, “I’m sorry. This place is about as perfect as I can imagine, but I’ve got to go see the world.”

I think the whole idea is I might never find a place as nice as this, but I need to go find out for myself. I can’t just stop now before my journey’s begun. That’s how I felt about Santa Monica.

To me, living in Santa Monica was like, “Wow, this is really as good as it gets, but I need to go see the world.” I’m sorry. I just realized your question had two parts.

Jeremy:

Here’s kind of the layout of what I was thinking. I lived in Peru for a little bit which is a very cool experience. I lived in Peru and somehow managed not to go to Machu Picchu. I don’t even know.

But culturally you understand people in situations a lot differently by living there. We’re told China is a certain way. I was in China for quite a while and it was different, but it was not what I was raised to think it was. I think it changes a lot of your worldview, so how did travel, and any place in particular, change your worldview? As I said, it’s a very loaded question, but I think it does really open your mind up.

Derek:

For me, I’ll pick one concrete example: Singapore. That’s where I went first when I left America. I became a permanent resident and did nine months of paperwork. I got legal residency, and then permanent residency and really integrated. Most of my friends were Singaporeans. There are lots of cool expats there too.

At first I thought, “No, no, no, I don’t want to meet any expats.” I could say that one little thing that surprised me is that expats are usually pretty cool people because they’re people like me. They have also been inspired to up and leave wherever they’re from, whether it was Switzerland or Argentina or who knows where.

But I wanted to really get to know Singapore. So when I was getting to know a lot of Singaporeans, I was shocked how many people would say things like, “Well, I wanted to be a musician, but my parents insisted I get a law degree. So I’m a lawyer now.”

I said, “No, that’s so wrong. No, you have to follow your dreams. You’ve got to live your own life!” It took me a couple of years of hanging out with good friends before I really started to understand the Singapore mindset, which is kind of influenced by Confucianism.

In general, we call it the collectivist versus individualistic mindset, and I make the comparison of meditation where meditation says thoughts will come and go in your head. Just let them go. Don’t take your emotions too seriously. I felt like my Singapore friends’ families are of the mindset that you shouldn’t take your whimsical passions and ambitions too seriously.

Instead, just do what’s best for the group. Like your family, the community, your country. This is what’s important in life – not your individual whims. I also made a lot of Muslim friends from India and understood that mindset better too, and it’s not so foreign to me now.

I have to go back to one more contextual thing. Even before Santa Monica, when I was 20 years old, I moved to New York City, and it was overwhelming and intimidating and scary. I actually moved there at a time when crime was at an all-time high. It’s a much safer city now. At the time it was not. It was dangerous.

Jeremy:

You were pre-Rudy Giuliani days?

Derek:

Yes, it was 1990, which I later found out, statistically, I moved there in the year when crime was at an all-time high. That’s when it peaked and it was scary to me.

But after just a year or two that was my comfort zone. It was just like, “Hey, this is my city.” All my friends are in every neighborhood. I knew every neighborhood. I knew every part of that town. New York City became, and still is my comfort zone. I thought, “What a cool transition that was.” Something that used to scare me is now my comfort zone.

How cool would that be to go do that again and again and again? Move to Rio de Janeiro and you’d be like, “Eh, it’s scary,” and within a few years you’re like, “Hey, it’s my comfort zone. Okay, so now let’s do it again. Let’s move to Moscow.”

It’s scary, scary, and now, it’s my comfort zone again. Now let’s go to Beijing. Now let’s go to Ulaanbaatar or whatever it may be. You keep going. Until – this was my dream – someday, I’d be able to spin the globe and everywhere on it would feel like my comfort zone.

Jeremy:

I love that because there’s the idea that at that point there’s nothing you can’t do or try. At that point, it’s not really scary anymore.

Derek:

You’ve just taught yourself over and over again that what scares me can become comfortable. Actually, ever since I was a teenager – I don’t know where I got it, but I’ve had a little motto that I use, like a rule of thumb that I let lead my life, which is “whatever scares you, go do it because then it doesn’t scare you anymore.”

Jeremy:

I love that. I just love the idea of doing it through travel because I’m from a really small town. It’s five eighths of a mile in size. Most of the people are in factory and industrial jobs. I was one of the few people that went to college.

So the idea of traveling and really checking out the world – you really see not only what’s possible, but you also understand groups that you didn’t experience growing up and you have more reality than other people. And I think it’s incredible to not only do bigger things, but also have that awareness and that ability to see where others are from. You know what I mean?

Derek:

Yeah. Where are you from?

Jeremy:

I’m from New Jersey, but I’m from Northern New Jersey. It’s kind of like living in West Virginia [laughs].

Derek:

Okay. Alright. I saw you have this address that’s on your site, and I saw that you’re by the big lake there.

Jeremy:

Now, I live 45 minutes south of where I grew up. We’re in a much more hip area and we’re by the largest lake in New Jersey.

Well Derek, you were talking a bit about the philosophy of being in Singapore, and it sounds like it was extremely conservative, which is interesting. Having it one way and not creating new things which is kind of different because that’s not how innovation happens. Innovation happens by doing different things, but at the same time, you’re also very interested in Stoic philosophy, which in some ways can be a bit conservative as well because you’re kind of managing your own reaction to things and how you deal with things.

I think philosophy is an interesting subject because a lot of people will be very into it, but they haven’t figured out how to use it in their lives. For you, the use and application of Stoic philosophy is a very real thing. How have you used that?

Derek:

First, I have to say that I’ve always lived with an approach to life that my friends find strange. I’ve always been this way since I was a teenager. I have always aimed to make life hard on myself to prepare for a tougher future.

I’m a pessimist like that. I always expect the worst. I always expect things to get bad. Do you remember long ago there used to be this series, it was called “VH1 Behind the Music?”

Jeremy:

Oh yeah.

Derek:

They would follow the story of some rockstar, and every story had the same arc of, “They were discovered and then things were getting better, and then they got their big hit on the radio, and things grew from there...” Then the narrator at some point in the story would always say, “And then things took a turn for the worse.” [Laughs].

I feel like in my life, I’m always expecting that narration to kick in. I’m expecting things to turn really bad. Because of this, I have always avoided luxury because I don’t want to acclimate to it. I never fly Business Class because that would make it harder for me to be okay with Economy in the future. I challenge myself to do without things just on principle to make sure that I can do without them in the future if necessary.

I like learning things the hard way to make sure that I understand the roots of whatever I know because I’m just pessimistically assuming that the fruits on top may change, right? I don’t want to just use some tool like WordPress to make a site.

No, I need to get down into the nitty gritty. I need to learn the HTML, the CSS, the SQL. In fact, I want to learn how to manage my own Linux server because I don’t trust anybody and all that stuff on top may disappear at any time. If this matters to me, I need to know the foundation of it.

I avoid anything that looks like addiction. I see these people that are so addicted to their coffee, they say, “Oh man, I’m nothing until I get my morning coffee.” I’m like, “No, fuck that. No coffee for me.” So I still have never tried coffee.

I avoid dependencies on anything. I’m just telling you about teenage or twenty-something Derek. This is my background. Then, at the age of 40, I kept hearing about Stoicism. Mostly from Tim Ferriss who kept raving about it, and we read a lot of the same books. So Tim kept raving about Stoicism, and it just sounded so boring to me. I was like, “Eh it’s some ancient Greek philosophy... dude I’m not into that,” but I was like, okay, I’ll read this one book reluctantly. So I read it.

The title was A Guide to the Good Life, and whoa, my jaw dropped. I was like, “Wow, this is me.” This is my weird approach to life. It has a name! It’s an official thing. I never met anybody that had these same beliefs as me, and now I find out it’s some codified 2,000 year old thing that people put a lot of thought into. To me, it wasn’t what Stoicism did to change my life. It was just wonderful to hear further thoughts on this approach since I had never honestly even thought mine through.

It was always just a gut feeling kind of thing, right? I need to always brace myself for a tougher future. I need to always expect the worst. So did it change my life? Not so much, but it justified the approach that I’d been taking before and it gave me some great reminders why this is a wonderful way to live.

Jeremy:

I think at the same time though, it’s also just taking greater responsibility for things around you because if you just look at the greater society, we have so many of these things that we’re becoming lazy and we’re losing ingenuity. There was a movie called Idiocracy, have you seen it?

Derek:

No I haven’t.

Jeremy:

It’s far in the future, and Terry Crews is actually president – the big muscle guy. Everybody’s gone to the point that they become so dependent on technology and everything else that they’re watering the plants with Gatorade and someone questions why. They say, “Because it has electrolytes. I don’t know what they are, but we know we need them.”

So I think at a certain point, we’re losing our capability by becoming too dependent on these crutches. Right?

Derek:

Right.

Jeremy:

So we lose the ability to create new things because we’re not taking the level of responsibility that, in Stoic philosophy, you’re taught to have.

Derek:

Right. I’m almost irrationally scared of any dependencies. I don’t have any subscriptions. I don’t use any subscription services. I just refuse because to me, that feels like, well now you’re locked into a dependency.

I avoid dependency on any one technology. I have two cheap phones – one old iPhone and one old Android phone and I switch back and forth every couple of weeks. Always erasing, wiping, and formatting just to make sure that I’m not being too dependent on any one software stack. I erase my computer every few months and format it and reinstall the OS from scratch just to make sure that I’m not dependent on anything I can’t replace quickly. It’s a real thing for me – avoiding dependencies.

Jeremy:

[Laughs]. One of the other big tools I’ve heard you talk and write about is the idea of journaling and how that’s actually become a really big component of your day and how you do things.

What made you start journaling, and what does your format look like in terms of how you’re actually implementing that?

Derek:

Four reasons.

Number one: the daily diary. One of the best ways to predict your future or to predict how you’re going to feel about something in the future when you’re sitting there at a crossroads trying to make a decision is to look at your past. Not through rose-colored or crap-colored glasses at a foggy, distant memory. You need an accurate representation of how you were actually feeling at that time. The only way to have that is through a daily diary, so I only trust my daily report of that day.

Looking back even a week later, it’s too easy to wrap things up in a nice or dramatic story. So I keep a daily diary just saying what I did today and how I was feeling and I keep it all in plain text files that are easy to search. So I can search for occurrences of people, places, or feelings. I can search to see, for example, when I first started considering a decision or how my thoughts progressed on it.

Number two: my topic journals. After a few years, I realized that there were topics I kept coming back to, whether it was my thoughts on Singapore, my thoughts on getting a dog, the value of travel, programming, asset protection, sex, whatever [laughs].

Instead of having these thoughts scattered around my daily diary, I decided to start keeping them each in one place, so I have a folder now called, “Thoughts On,” and inside that folder are about 150 little text files, but on one subject.

So there’ll be, “thoughts on... Dog.” For about a year, I was on and off considering getting a dog. Each time I was considering it, as a way of thinking out loud, instead of putting it in my daily diary, I’d open up my thoughtson/dog.

I would just start typing today’s thoughts on getting a dog or not, so that later as this decision progresses, I can look at all my collected thoughts going back months or years, depending on the size of the decision, in one place. So that’s a topic journal. It’s incredibly handy. I love it. Whenever I’m thinking about a certain subject that I keep coming back to, I do it all in one place.

The third reason and methodology is that I like planning. It’s like daydreaming on steroids. When I get a nice idea, I like to dig into the implementation of it. I’ll write down exactly how I would make this idea happen. I’ll list out all the steps, even if I never end up doing anything about it. I just love geeking out on planning how I would make this idea happen. Whether it’s moving to Mongolia or building a web app, I love to just plan it out.

Instead of just having some vague idea, I dig into the details. It makes the daydream more vivid, you know what I mean?

Jeremy:

Yeah. James Altrucher talks about something similar to that and it gives you the ability to create more ideas just because you’re in that creative space. You’re working the muscle. The more you do it, the more things you can create.

Derek:

Right! Lastly, the fourth reason, and this is the most important reason or it wraps up the other three, is that everything I’ve learned has come from reflection.

This can be daily or by topic or while planning, but the point is, it’s organizing your thinking. Putting something into clear writing helps to straighten it out in your head. So does telling your friends about it. I also benefit a lot from chatting with friends and bouncing ideas off each other – explaining something to a friend who doesn’t know what I’m talking about. Sometimes just explaining something helps, but I think this is even better where you write down your first thought, then your following thoughts, but then you go back to question what you just wrote.

If you wrote down a statement, now question if that statement is really true. Well, what’s the opposite of that? Could that be true as well? How would someone challenge this? If I were to present this idea publicly, what would the probable pushback be?

So if this weren’t in writing, I would have a hard time keeping all this straight. All these thoughts would disappear into a cloud, and so I just love having it all in writing to go back and reflect on again and again and build off of it.

Jeremy:

I love that. You mentioned the type of journals you do. Based on your journaling process, do you find that there was one idea that completely changed by the time you worked it through?

Derek:

Oh god, most of them [laughs]. Oh man. So many.

I still come to terms with, for example, my concept of home. I’ve had a few different homes in the last few years in a few different places. I’ve lived in a little furnished apartment with one suitcase for a year. I’ve lived in a nice house that I bought a bunch of furniture for and moved in. Then after that, I lived in an AirBnb for a few months.

I’ve tried a bunch of different approaches to home. Sometimes I splurge, sometimes I go cheap. Sometimes I have a great view. Sometimes I have none. It’s just interesting to constantly come back to this, “What does home mean to me?” journal, and adding to my ideas.

I make some assumptions based on my current situation, and as time goes on, I re-question those assumptions and add some more refinement to it.

Jeremy:

Absolutely. Well Derek, if we were to take a look at historical figures, for me, the person that I’m most intrigued by is Alexander the Great. I can’t even tell you how many books I’ve read about him. What historical figure has inspired you or interested you the most?

Derek:

Hmmm. I don’t know much about Benjamin Franklin, but I’d like to learn more about him if I’m thinking historical. He seems like he was a very thoughtful dude.

Jeremy:

He created a lot of things well before their time as well.

Derek:

Right? What got me interested in him is that I was in Brussels, Belgium at the Museum of Musical Instruments, and they had this glass one that kind of looked like – imagine if you would take fifty wine glasses of different sizes and tip them all over on their side so the biggest one is on the left and the smallest one is on the right, but all in a row.

Now you put an axle through the middle of it and spin them through water with a tray of water beneath them, so that you can rub your fingers on top of them while it’s spinning. I forget what it’s called right now.

Jeremy:

Glass Armonica

Derek:

Thank you, and Benjamin Franklin invented it!

I listened to it and wow, it’s gorgeous. My god that mofo invented bifocals and the kite and electricity. Wow, and you know the constitution [laughs]. I really want to learn more about this guy. So that’s just the first one that comes to mind.

Jeremy:

Absolutely. Well, Derek, I just have two more questions for you just as we’re kind of wrapping up here. If you were to take a look at 21 year-old Derek versus Derek now, what would be something that you believed then that you don’t believe now?

Derek:

What was something I believed then that I don’t believe now?

Jeremy:

Yeah. Something you held as a truth at twenty-one that you don’t hold as a truth now.

Derek:

Ah, let’s see. We should make all our goals come true. I’m going to be a famous musician. Music is my life. Money doesn’t matter. Rich people are greedy. The love of my life is out there. I’ll never have a kid. It’d be bad to be well-rounded. If only had, “blank, blank, blank,” then I’ll be happy. Famous and successful people are a different breed – they are a different kind of person. They’re intimidating. I need to make a plan and follow it well.

Jeremy:

It sounds like you’ve had a lot of viewpoint shifts, man [laughs].

Derek:

A lot [laughs]! This is just off the top of my head. Those are the first ones that come to mind, but dude, when I think back to 21. I just turned fifty. Twenty-one – it’s almost hard to remember what I believed at the time, but those are the ones that come to the top of my head.

Jeremy:

Very cool. If we were far in the future, and you have a few weeks before you’re going to pass, but you are lucid enough to write your own epitaph, what do you write, man?

Derek:

[Laughs]. I can’t be reduced to a sentence and neither can you.

So, here’s what I’m doing, and what I recommend everyone listening to do, too. Write your own autobiography. Start now. Don’t wait until you’re in a hospital bed. Start to write your own autobiography now. Add to it occasionally. Write the last chapter first – the after-you’re-dead chapter, then keep filling in the previous chapters until you die. Tell your family where to find it on your computer, so that when you’re dead, they can release it to the world. Tell your story, share your thoughts, record your personality.

I believe that different religions disagree on what happens after you die, but I think we can all agree on this: Your personality lives on in the thoughts of others. The people who encountered you, whether it be in-person or online, got to understand your personality, right? They get to understand your thought process and the way that you see the world.

This is the uniquely Jeremy Ryan Slate way of seeing the world, and when you’re gone that stays with them. They’ll continue to smile at the things that you said, or they’ll continue to find some of your insights useful. They’ll remember your weird opinions. They’ll remember what you loved and why. So, I think we should each share our personality. Share your thought process. Share the way you think because that is your afterlife.

Jeremy:

I love that. What an amazing shift on that. Well, Derek, I really enjoyed this man.

As I said, I’ve waited four years for this interview, and I’m glad we could finally do this. For all the people out there listening, if they want to connect with you, if they want to follow you, where’s the best place to go?

Derek:

I’m actually weird in the fact that I like hearing from people. I’m basically retired. I don’t do anything for money anymore, and one of my favorite forms of compensation, payment, or virtual payment is hearing from people.

I really like hearing from people that introduce themselves. So, go to my website. Go to sive.rs, and you will see a big “Contact Me” link. I put my email address right there in a huge font. So use it. Say hello, introduce yourself.

Jeremy:

Awesome. Well Derek Sivers, thank you so much for hanging out with me today on The Create Your Own Life Show.

Derek:

Thanks! It was fun.