Derek Sivers

Interviews → Erich Wenzel / Feeding Curiosity

Different approaches to curiosity, self-reliance, becoming a world citizen, seeing things from a different point of view

Date: 2020-02

Download: mp3



Welcome back to another episode of Feeding Curiosity. On today’s episode, we are joined by Derek Sivers.

This is awesome. Thanks for making the time and pushing my question-asking abilities to the limit that I hadn’t known was possible.


Glad I could help.


So give us a quick little bio. What have you been doing and what are you focusing on right now?


To paint the picture of who am I and what do I do: I’ve had a few faces. First, I was a professional musician for 15 years from the age of 14 until 30. I was pretty much nothing but a musician.

I was completely obsessed. In my fifteen years as a professional musician, I spent 10 of them working in a circus as a ringleader MC and toured around the country doing that.

I moved to New York City. I played guitar for a Japanese pop star. I was a professional session musician around New York City, playing on people’s records and stage, produced people’s records, and then I started a record label. I did lots of stuff in there.

One thing I did was start a little online record store, which was just meant to sell my CD, but then my friends in New York asked if they could sell their CDs, so I said ”yes“. Through my little store, I accidentally created the largest seller of independent music on the web called CD Baby that ran for 10 years with 150,000 musicians and 85 employees and millions in sales.

It was way bigger than I ever wanted it to be. After 10 years, I was personally done. Eleven years ago, I sold the company and became a writer, speaker, thinker kind of guy.

I spoke at the TED conference a few times. I released a book. I’ve got three more books coming and that brings us up to today.


That’s awesome. Part of that story is this arc of accidentally becoming [laughter]. The ability you have to unpack all of those things, to be really clear about what it is that you are and what it is that you aren’t.


Some things in life are intentional and some things aren’t. That happens to everybody. We choose some of our destinies. Some of it is through our own efforts and steering and some things just plop into our lap or happen — even in a bad way.

Somebody is pursuing a career as an athlete. They get into a car crash and that spins them off into a different direction and that’s how they became a lawyer. You never know which aspects of what you’re pursuing or are going to happen or not.

I sold CD Baby in 2008 and I felt like I had peaked. I thought, ”This is it. I sold the company for millions of dollars. This is what’s going to go on my gravestone: “He did CD Baby and not much since.”

I was in my 30s. I spent a couple of years feeling pretty lost until I got a new exciting idea. I thought, “I want to speak at the TED conference. Not TEDx. I want to speak at the big main stage TED. I want them to invite me.”

That got me inspired. That got me to jump out of my chair and get into action. It was the most exciting idea I’d had for a while. That whole thing happened very deliberately with great intention. But starting a business was a total accident.


Wow. Does getting into TED require some sort of writing or does someone have to find you? I’m just curious how that process goes. Is there a committee where certain people say, “Yeah, this guy should be able to talk there.”


I’m not sure. I think it’s pretty ad hoc. I think they keep it ad hoc so that people don’t try to game the system, but in my case, I was an attendee of the conference. I’d already bought my ticket to attend and then they asked attendees if anybody wanted to give a talk. So I proposed an idea and they said, “Yes. You. Give this talk.”

That was it. I did it three times in one year.

I spoke at the TED conference in Oxford, England, then in India, and then in California.

That was back in 2009. I haven’t done it since.


That’s an interesting thing, too, for someone relatively young to have sold a company and be like, “Yep, there’s my high water mark [laughter].”

How do you have the rest of your life to go through to live in the shadow of that?


That’s what I thought was going to happen. It’s cool that right now most people know me through my writing and books and podcast, but there was a time in 2010 to 2012 where it felt like everybody knew me through TED.

Everybody knew me as that TED speaker guy, because my three talks all were quite successful. They got millions of views on the site. People would ask, “So what did you do before TED?”

I thought, “YES!” [Laughter].

That was such a cool question to hear because I thought that CD Baby was going to be the last good thing I ever did. So it was such a cool thing to be known for the next thing. I’m 50 now. I hope I make another couple transitions like that. That’d be fun.


Yeah. That’s really cool. I think that’s one of the more interesting things in today’s world — that people can have second, third, or fourth lives and different career paths where they can say, “I did this thing and then I left it all behind and now I do this thing.”

Someone can find you at many points in that trajectory and then think, “Wait — what else did he do? Why is he here? Hold on.” Then being able to unpack that story because that’s really the idea of a generalized specialist, which we’ll get into later.

Back to the writing aspect of what you do since that’s your current focus. What does your process look like, and when you get stuck or unfocused, how do you reset yourself?


I don’t think writing is much different than any other pursuits. Meaning I don’t think I have a writing process that’s different than any other process of getting stuck. When you ask that question, I can imagine myself getting stuck more on some programming things I’ve done.

So with writing, I think it’s the same as anything else. When you get stuck on something, you just try to break down this big problem down into smaller, more specific problems.

That’s the same with anything in life. If you’re stuck in a creative problem, whether it’s making music or whatever you do, there’s always a way to flip it over and consider the opposite. That’s a typical tool in the toolbox of people doing anything creative. Let me try reversing it. Let me try doing the opposite of whatever I’m doing. Let me take a 90 degree turn. Now take a 180.

On the other hand, if you’re having a stylistic problem — if you’re just sick of the sound of your own voice, I don’t mean your voice boxÊbut whatever you’re doing artistically, you can always just pretend that you’re somebody else, whether it’s your role model or something else, and you can do whatever they would do.

For years I was a singer and my voice teacher would teach me a new song and he’d say “OK, now sing it to me like you’re sneaking up on me with a knife behind your back and about to kill me. OK, now sing it to me like you’re Grover from Sesame Street.”

You don’t have to be yourself. You can be someone else when you’re doing something creative and feeling stuck, you can always do it a different way.

With life decisions, I’ve recently found a new way of making or getting through major life decisions when I’m feeling stuck. I describe my problem to a mentor, especially if it’s someone who doesn’t know me at all. Then I have to summarize my entire context to a disinterested person.

Just imagine you’re going through a major business problem and somebody says, “I’ll give you five minutes on the phone with Richard Branson.”

You go, “Oh, my god, Richard Branson. My god!” You’re only gonna have five minutes. So Richard Branson knows nothing about you. You have to summarize your entire situation and the problem you’re going through down to a one minute explanation of context and a one minute question.

How would you do that? To respect their time, you have to be as succinct as possible. What I found is that by doing this exercise, by reducing the problem down to its essence, the answer becomes clear without you having to actually go contact some successful mentor. No need for Richard Branson [laughter]. Going through that exercise usually makes the answer pretty obvious.


That’s really interesting because it allows you to distance yourself from the problem. You have to just take it for its root elements and say, “Ohh.” Then it’s the slap yourself on the forehead kind of thing [laughter].


It’s interesting to see it stripped of all emotion. That’s why it’s better talking to a stranger than talking to a good friend. Your good friends care about you. They know you, they can rely on your background and context, but when you’re having to tell something to a stranger, you really have to summarize more than ever.

But that’s best for a certain kind of problem. Like if you’re a painter and you’re stuck on a painting, maybe this approach will help. For major life decisions or maybe even business decisions, you could look at it like that.

But I really do enjoy the opposite — going back to the first thing I said about taking something and flipping it upside down and asking yourself the opposite.


It’s worth noting that not every mental framework or mental model is going to work to solve every problem. It’s knowing that, “OK. This is the type of problem I’m dealing with,” and then opening up the mental toolbox basically and seeing which one of these is going to work best.


Right. Let’s try this. Let’s try that.

Years ago, I wrote a tiny little article called “Hell Yes or No” about a tool that I use for certain situations like when I’m feeling overwhelmed. And when I have too many opportunities, and I’m feeling like I’m drowning.

In that specific case, I’ve got a rule called “hell yeah or no,” which applies if I’m feeling anything less than, “Oh, hell, yeah, that would be awesome! That would be amazing!” If I’m feeling anything less than that, I just say “no”. So it’s basically “no” to almost everything.

The problem is that some people like that article and quote it a lot. Then some people email saying, “Oh, my god this is great. I’m using this for everything now. I’m applying this to my relationship and everything else.”

I go, “Wait wait wait! This is not something you use when you’re fresh out of college and you’re not sure what to do with your life. You’re not drowning in opportunity. In fact, in that case, the best strategy is to say ’yes’ to everything.”

There’s different tools for different times. Even certain philosophies are applicable just to certain situations.

I found it interesting that somebody actually critiqued Buddhism once because they said that Buddhism was invented in a time where people were mostly helpless. It was invented at a time where the king could decide to take your land because he felt like it. So Buddhism was a way of detaching from the outcome of everything as a way of protecting the downside.

But by detaching from everything, it means you don’t really get the upside either. It was a really interesting critique to say now we’re in an age where most things are up to you and Buddhism might not be the best approach anymore. Even an entire philosophy or religion or whatever you want to call Buddhism might have just been a certain tool for a certain time.


If you become an expert in something, for instance, I’m an engineer, or someone can be an artist, musician, or writer. I tend to view those as problem-solving lenses.

Remember back in the 90s we had those toys with the thing you put in front your face with the levers on the side and overlaid different images?s

That’s how I tend to view different mindsets or different ways of solving problems. Maybe I can start overlaying lenses, but then the really fun part is when you overlay lenses from multiple domains because then it gives you superpowers to be able to look at things in different ways that other people might not see.


Cool. I like that.


Those are some of my thoughts to make things easier for people because we like to think in boxes, which is where we’re headed for the next question.

You tend to look at writing and coding as very similar tasks. Being both an an engineer and doing this podcast has helped me reformulate what creativity is for myself.

How do you reframe creativity? Like putting music, writing, and coding in similar categories? I think that’s fascinating.


Everybody knew me as a musician for 15 years because it was my monomaniacal obsession. I had no interest in anything but music.

After 15 years, I stopped making music and started programming. My friends were shocked and almost offended [laughter]. “How dare you! What are you doing? You’re a musician. Now you’re programming? What the hell are you doing dude?!”

I felt like it wasn’t that different. They said, “The hell, it’s not!” but when I’m writing a song, I was trying to solve a specific problem.

It’s like I had a certain idea in my head. “What if I took this rhythm from this Fela Kuti song, mixed it with a Beatles kind of melody, but then did the funky Prince guitar thing. I wonder what that would sound like?” I would go try it.

Now I’m programming. I think “What if I took this database back end and then I found a way to make this do that? I wonder what that would be like?”

To me, it felt like the same kind of process. The people that were most surprised that I found programming creative were either people that knew nothing about it and just thought it seemed like a dumb day job, or people for whom it was a dumb day job that we’re in it for the money.

It’s not like making music is creative and programming is not creative. I think it’s a matter of who you’re doing it for.

If I was assistant to a Hollywood composer, and Paramount Pictures was telling the composer exactly what to do, and then he was dumping it on me saying, “I don’t have time. You arrange the horn section. Make it exactly like this.”

That’s not really creative anymore, is it? Now, it’s some stupid task I’ve been assigned. I have to arrange the horn section, so that’s not creative. But say that was my day job, and at night I would go home and play with computer programming to invent my own mobile app idea. Then this computer programming would be my creative outlet and vice versa.

Of course, if I worked for a big company that was telling me exactly what to program on computers and I was just typing out Java code to meet their specs, then programming wouldn’t be very creative and I would go home and play guitar as my creative outlet.


That’s a really interesting perspective because I think a lot of people go into something because it strikes their creative itch in some way. It’s like they get to play with mixing a different palette to use a painting metaphor.

What we don’t realize is that when you start getting into the working world, routine is going to occur. For instance, my brother works in a corporate environment as a graphic designer.


Ah, great example.


So he has to work in a very specific palette set. The typeface and everything is very structured, so he can’t play outside of a lot of boundaries as a graphic designer. He’s obviously really good at what he does. Otherwise, he wouldn’t be able to work in a corporate environment for graphic design, but he’s still comes to me sometimes and says, “Man, I just feel like I’m too boxed in. It really frustrates me because all the bureaucratic overhead.”

I say, “You’re just a creative at heart and you need to have more leash.”

Would you say creativity is an innate thing? That there’s a thing that’s going to grab you by the lapels and compel you to create?


No, I think it’s a matter of whatever seems fun. A few days ago, I was with my kid and we were out and he saw a Rubik’s Cube and he said, “Can I get a Rubik’s Cube?” It was eight bucks. I said “Yeah, alright. I’ll get a Rubik’s Cube.”

We took it home and he was playing this game where he would make a couple twists and hand it back to me to solve it and then we played that with each other.

He said, “Close your eyes,” and he made so many twists that it was completely messed up that I didn’t know how to fix it [laughter]. So then I went to YouTube, and I found a video explaining how to solve a Rubik’s Cube. I spent an hour learning the algorithms, or the tricks to learn how to solve a Rubik’s Cube.

First you solve the bottom layer, the middle layer, and so on. It was fun. It took me about an hour and it was fascinating and it turned into a fun memorization exercise.So now I can solve a Rubik’s Cube in about three minutes.


That’s really cool.


The audience doesn’t know this, but we are talking two days before Christmas.

It’s always a wonderful, quiet time of year where nobody outside of your family’s expecting anything from you. It’s a great time to disappear. Dive into something new. So on Christmas Day a few years ago, I was reading something about the language called Esperanto. I remember I sat down in my chair at 4:00 PM and thought, “Oh, this is kind of interesting!”

Dude, I didn’t get out of my chair until 11:00 PM. It was pitch black. All the lights were off the whole house. I was riveted. I was glued to my chair like, “Oh my god, this is the most fascinating thing!” I sat there for seven hours learning about Esperanto for no practical reason, same as the Rubik’s Cube.

This is interesting to me right now. I was not interested in Rubik’s Cube a week ago. I was not interested in Esperanto six months after that, but at the time it was interesting.

This week I’m learning a book typesetting programming language because I need to. I have my own intrinsic reason to do that because I have books coming out that I don’t want to be dependent on typesetters for.

Even in situations like this interview, where you threw strange questions at me, and I thought about them to try to come up with an answer that’s interesting to both me and your audience.

I wouldn’t say that these are inherent creativity things. In all three of those scenarios, not until something is thrown at you, do you get interested in it. I wouldn’t say that some people are curious and some people just aren’t. People who think they’re not curious probably just haven’t been in situations where they’re exposed to something that they find interesting.


I couldn’t agree more with that. This thing is called Feeding Curiosity for that reason [laughter]. What is that thing that makes you stop and go, “Huh?”

Then you just start going down the rabbit hole of whatever that is. When you stop and reflect on what that rabbit hole opened up for you, then you realize, oh, I’m a lot farther than where I started [laughter].


Right! There’s a wonderful saying that goes something like, “The ocean gets deeper the further you go into it.” The point is, curiosity is very specific and situational. You can’t say that this person is curious and that person is not curious. Those two people might be reversed in different scenarios.

My advice is that if you feel even a hint of interest about something, you can go learn a little more about it because the more you learn, the more interesting it gets. When you know nothing about a subject, it’s hard to be curious about it because you don’t even have any questions yet. Once you start learning anything and you have more context, then you start having more questions and you get more interested.

It helps to have a real need. Even a tiny one, like my Rubik’s Cube example, but this is a great argument for why people should get out of their comfort zones and go do random different things, exposing themselves to completely different inputs.

If you’re just going through the same routine every day, you drive to the same job and come home, do the same thing, eat one of the same six dinners in front of the TV, then no wonder you’re not feeling your curiosity sparked. You’re not getting exposed to new inputs.

If you scramble it, mess with it, then suddenly, you’re sitting there talking with a stranger who trains horses and he’s telling you how exciting it is. Suddenly you’ve got these new inputs. It makes you go, “Oh wow!”

A year ago, I got super into dog training. I had no interest in dogs, but then my kid wanted to get a dog, and suddenly, I was looking into learning all about training seminars. I read five different books about dog training and I was fascinated with it.

All of this stuff just comes from being exposed to random input. Anybody listening to this show that wants to spark their curiosity more — go scramble your inputs. Go expose yourself to something completely outside your usual circles.


I think that’s really cool. It triggered a thought from Michael Pollan’s new book called How to Change Your Mind. He talks about psychedelics, where you take your snow globe, which is your brain, and then you shake it all up and let everything resettle in new ways.

You have to shake your snow globe every so often. Otherwise, you’re not going to see new things or be interested because everything is just settled and stagnant.

To keep building off of this curiosity and exploring theme — you have so many different skills that we’ve covered with your music and coding — how do you think about crossing skills across domains, or how would you look at skill acquisition more broadly for someone in college where you have to pick a degree and then stick with that thing for four years or longer?


First, you have to understand, you don’t have to [laughter].

There was a really interesting turning point for me about 12 years ago when I was working with a guy, kind of like a coach, mentor type guy, before I sold my company. I wanted to quit. I really wanted to leave. He asked why, and I said, “I’m sick of doing all these things I have to do,”

He said, “You don’t have to do any of them.”

I said, “Well, I have to pay my employees. I have to pay my taxes. I have to ship out customers orders where they pay.”

He said, “No, you don’t.”

“Of course I do! What do you mean no I don’t? Come on. Yes, I have to pay my taxes. I have to pay my employees.”

He said, “Derek, I’m not just being a smart ass. You really need to understand this point. Before we continue, you don’t have to do anything. You don’t have to pay your taxes. Nobody does. You don’t have to pay your employees. Nobody does.

But look at what will happen if you don’t pay your employees. They’ll eventually stop coming to work. A few of them might file lawsuits. Most of them would probably just walk away, give up and grumble and hate you. But you don’t have to pay your payroll. You don’t have to pay your taxes either. After a few years, the IRS would probably come back to you and they would charge interest on back taxes.

But let’s be clear. You don’t have to do anything. You could just walk down to the local park, lay down on a bench, and stay there for a few years [laughter].

You don’t have to do anything. Everything you’re doing, you’re choosing to do. You need to understand that. Never forget that you’re choosing to do this. At any point, you can just choose not to. You don’t have to. Just walk away from anything. There might be some consequences. But more often, there’s not.”

I had to call that out when you said you have to choose a major — you have to pick a focus.


I appreciate that because I was doing all of this stuff in parallel with finishing a degree.


Right. Good example. Maybe inside college, you have to do a certain thing. Even then you don’t have to. Even inside college, you can get the most out of it if you pick a thing knowing that it’s not going to be your entire life.

To answer your question about skill acquisition and skills across domains, whenever something’s important to you, you should get to know the foundations of it.

The main reason is because if something really matters to you, you don’t want to be at the mercy of any particular person or particular company. A lot of what I’ve learned has been out of self-reliance because I’ve been around long enough to watch a lot of companies disappear. Companies that people were depending on that people have uploaded all their stuff to. Next time there’s a market crash, they’re gone.

Aren’t we in the longest bull market in history right now? There hasn’t been a crash in 17 years. Before that, there was a big crash in 2002. I think and there was kind of one in 2001 and there was kind of one before that, so I could see why somebody who’s just been online for 17 years thinks that it always goes like this. Go back 17 years, there were a lot.

Imagine if tomorrow, Google, Facebook and Instagram went out of business and all of the stuff you’d ever uploaded to them — your photos and whatever else were just gone. They’d say, “Oh, sorry. Well, we went out of business. What can you do?”

“Wait! But no. All of my photos. My pictures of my kid! I was depending on you.” The appropriate response would be, “Well, you idiot. Why would you depend on a company?”

“Oh my god my Gmail address is gone. I was depending on my Gmail address!”

Well, you idiot. They’re a company. Don’t depend on a company. Gmail might be gone tomorrow. Actually, most of the people listening to this interview will outlive most of the companies they use. You’re probably going to live another 70 or 80 years. That’s probably probably longer than your email provider will last, or the place you uploaded your photos to will last.

The point is, if something matters to you — whether it’s your photos, writing, or books — don’t depend on any particular person or any particular company to manage that stuff.

I felt the pain of being helpless when long ago when there was an expert that I was depending on. I didn’t know programming yet when I started CD Baby, and I hired this guy to help me with my programming. He was the only person that knew how to do something I needed with my database.

Then he disappeared, and suddenly, my store was broken. He stopped replying, and he was just gone. Not answering his phone. Nothing.

I just said, “OK, that’s my fault. I was an idiot. I was dependent on this guy. That’s stupid. This business matters to me. I’m not going to have my business collapse because one guy disappeared.”

So I tend to learn things because it gives me self-sufficiency and independence where it matters most to me, but these things are different for everyone. I don’t depend on my car or my bike right now in my regular life. I live in a neighborhood where I can walk everywhere. I have a car and bike, but if they break, I’ll just pay somebody to fix those. They don’t matter to me enough.

I’m self-publishing my books now, so I don’t want to be dependent on a graphic designer to do the layout. This week, I’m learning the core language behind desktop publishing so that I’m never dependent on any designer.

For someone else, it might be vice versa. If you lived out in the country, you might be completely dependent on your car. It would be worth your time to learn how to fix your own flat tire because you live in the country.

But graphic design? You don’t care. Just pay somebody to do it. So learn the foundations of things that are important to you so that you’re self-sufficient. In doing that, you talk about skills across different domains and skill acquisition. You learn things out of necessity. That’s how we all learn. Unless it’s a Rubik’s Cube or dog training that you find fascinating by some weird random chance.

But for most of us, we learn things by necessity. That’s the best way to learn. Even with computer programming. If that would have been a class in college that I had to take, I would’ve had no interest at all. I would have been a terrible student.

But a few years later, I started this website, and it was suddenly growing faster than I could handle by myself. I desperately needed automation. I was learning programming like my life depended on it because it kind of did at that point [laughter].

So learning by necessity is the best way. Things that later look like you’ve got many skills across domains, it’s usually just because you had to learn some things out of necessity.


I completely agree because that’s been my parallel path with learning how to manage. The reason I have my own website is because I didn’t want Facebook or any of the social media platforms to be the one stop shop controlling traffic.

They’re gatekeepers. I wanted to be able to control and see what I’m really driving traffic-wise. Not even for money purposes, but just because this is what I wanted to put out in the world. I’m going to take responsibility for the things that I put out publicly.

Also, I love reading so much and there was a point where I realized I should probably start switching to e-books because I didn’t want to read physical books for environmental purposes.

Then I started thinking about it because I love having real books. I thought, “You know what? If the Internet goes poof one day, then all this knowledge effectively evaporates.”

I love collecting knowledge. I think maybe I should just keep buying real books because they’re not really much more expensive and I can keep a library so that if it all goes sideways then I still have access to information, and I can help other people.


On that note, I’m the same way, but I don’t use the Cloud for anything. Even for all of the e-books I’ve bought through Amazon, through the Kindle, I use a program called Calibre with a plug in called cult DeDRM to take off the digital rights management.

So if you put the DeDRM plugin into Calibre, then you can open up your Kindle book in Calibre and then save them as an open, unlocked ePub format so that they are yours forever.

I went through the same thought process as you a few years ago. I thought, “I paid a lot of money for books and these are my books. I don’t want to leave them in Amazon’s Cloud and watch them disappear. So for anything I bought and paid for, I strip the DRM off of it and keep my own archive.

I have a hard drive with every piece of music I’ve ever bought, every video I’ve ever bought, every book I’ve ever bought. If it’s something that I’ve paid for, I archive it for my private digital library forever off-line.


I’ll definitely be going down that rabbit hole at some point because it’s really important to figure out ways that we can have the things that we care about. At the very least so that it doesn’t become beholden to some other thing. We can have it longer than us hopefully [laughter].


When I was doing the world citizen thing and traveling a lot, I remember the first time I went to India. I was going to be there for a month and a half. My suitcase was half clothes, half books.


Books are heavy [laughter].


It was shortly after that when I said, ”I think it’s time to consider that Kindle thing.“


They’re definitely not easy to travel with either because they take up a lot more volume, and they’re pretty heavy. That’s where I was going next with this world citizen idea. It seems like Millennials want to start being world citizens. Vagabonding is a popular book. What are your thoughts on it?

It’s ironic that we grew up in the Midwest in very similar locations. Here we have really deep roots in family ties. My parents have not moved farther than Indiana. All the traveling I’ve done has been with my friends where you fly somewhere, spend five days there, and come back. Nothing crazy. Pulling the trigger is really hard.


We all have different definitions of what we want. I’m the black sheep of my whole family. My sister, my parents, cousins, everybody — they all live a mile from each other. I’m the one black sheep on the other side. So it depends.

A few years ago, I went to The Digital Nomads Conference. Even while I was there, I found out that most of the people, even though they were self-described as digital nomads, still had the definition that meant, ”I’m going to go hang out in a hammock in Bali or Thailand for a few years and drink cheap beers and work on my laptop on the beach.

But at some point, I’m going to return back here where I grew up and have a kid near my parents so that my my kid can grow up near his grandparents.“

I had a completely different definition. I wanted to leave and never, ever come back. My definition of nomading is to actually deeply integrate into each place and become a legal resident, maybe even a citizen, and truly make this place my home for a few years. After that, move on to the next place and do it again.

But let me back up. Even at the age of 36, I had no desire to travel. This was not something that was always in me.

I was living on the beach in Santa Monica, California. I was as happy as I could be. I had an amazing home. It was tree house that was wrapped around a tree right near the Santa Monica Beach. I was in the music business and Los Angeles is the place to be.

It was paradise. The weather was perfect. I rode my bike every day. You couldn’t pay me to travel. I had no interest at all. At the time, I had a girlfriend that wanted to travel the world. I was like, ”Hell no. I live at the end of the rainbow. This is the best place ever. Why would I travel?“

Then, one tiny idea got into my head that I couldn’t stop thinking about. It was that you really only learn when you’re surprised. If you’re not surprised, you may be taking in more information, but your mind isn’t really changing.

You only really change your mind when you find out that your previous assumptions on something were wrong. That’s the only time you really change your mind.

One of the best ways to keep yourself surprised daily is to live somewhere very unlike what you know. Immerse yourself in different cultural perspectives and very different ways of looking at life, communication, and approaches to expectations or values.

I had this idea around the age of 36 and it wouldn’t leave. In that one moment, I felt like I couldn’t un-think this idea and it shaped how I wanted to live the rest of my life.

It’s so important to me to keep growing and keep learning and never get stuck into habits that hold me back. Ideally, I’d like to keep moving to more and more challenging places living in each one until it feels like it makes sense. I’d love to move to a place that seems completely bizarre right now like Beijing, China.

I would love to move to Beijing. I’m sure it would be incredibly frustrating and annoying and difficult, but then give it a few years and it would probably start to feel like home, like this is where all my friends are.

After a few years, once Beijing makes complete sense, then it’s time to move to Rio de Janeiro or to another place that doesn’t make sense and then do it again. That’s a great recipe to keep pulling out the rug from under your feet.

Of course, there are other ways to do it. Plenty of brilliant geniuses have never left Chicago. There are people way smarter than me that are still in their hometown [laughter]. I’m not saying this is the only way, but I think that this environment helps me.

I know too many people that are constantly learning and changing when they’re in their teens and in their 20s, and by the time they start to get into their 30s, they say, ”Well, this is who I am. Yep. This is where I live. This is my favorite team. This is where I work. This is what I do.“

Oh, fuck. You’re 35! Come on. You’ve got another 60 years to live. You’re done at 35? That’s ridiculous.

But you asked about getting unstuck?


Yes. How do you get moving and get past that first initial resistance?


First, I’ll tell you a tiny, cute little moment that your listeners might appreciate. I already said that I had this idea, this itch that wouldn’t go away, but it was really this moment in December at the age of 36 when I said,”You know what? if I just started traveling the world and went somewhere like London. Let me just see. . .“

I went to some travel website. I was living in Portland, Oregon at the time, and I said, ”Let me just look at prices. OK. It wants me to pick a date. I don’t know. May 1st? OK, I’ll pick May 1st. Oh, no. It needs me to do a round trip.

OK, well, what is six months after May? November 1st. Alright. Fine. There are your fake dates. Let me see what it would cost to go round trip from Portland, Oregon to London, May 1st to November 1st.“ Then I clicked search.

”Holy shit. $380? That’s amazing. Wow, that’s cheap. I better book that! I’m going to book it.“

The idea came into my head, and a minute later, I had typed my credit card and clicked book. Because it was only 300 bucks. I was like, ”Huh? I just booked a six month trip to London [laughter]. Well, I guess I just did it. I guess I’m going to go to London for six months.“ I didn’t know anything else. I didn’t know where I was going to stay, but I just booked it.

That’s one way to take a first step, but in hindsight, London is too similar to New York. It might as well have just been Boston or something. It’s not that different.

It’d be different if somebody is listening to this from Estonia. Yes, but if you’re an American, then don’t choose Canada, England, Ireland, Australia, or New Zealand. The cultural differences are so minor that it almost doesn’t count.

On the other hand, don’t let that stop you just because some dude in a podcast interview said not to. If you really want to go to Ireland, then go. But I think if you’re feeling like you want a blank slate, consider some place like Singapore because Singapore is pretty unique in that English is the first language there. The government, all the newspapers, and all the media is an English, but their cultural values are very different.

It helps to go someplace where you don’t have to learn a new language yet. If you’re taking your first step out of your home country then it helps to go some place where you can speak English because then you can assimilate and integrate. That’s the important thing.

If you’d rather not go to Asia and you’d rather start with Europe, then consider Budapest, Hungary, or Lisbon, Portugal. Those are two places that are quite different culturally, but most people speak English to get by.

But whatever place you choose, my advice is to integrate. You really have to assimilate and integrate into local culture. You can’t just go there and stay in the little expat bubble and joke with other Americans and go drink beers and laugh at silly foreigners [laughter].

You’ve also got to get past that initial feeling that they’re doing everything wrong. At first, when you get to a foreign country, you’re going to focus on the frustrations. Day-to-day life will be frustrating and you’ll accidentally generalize.

For example, this happened to me when I first got to Singapore one day. When I first arrived, I went to go do something with customer service. I was trying to get my phone bill or something like that, and somebody was rude to me.

I came home thinking, people in Singapore are rude. Of course, it was just that one person that was rude to me was on the other end. If you go down to your local grocery store right now and the checkout clerk is rude to you, do you think people in America are rude? No. You think, ”Wow, that person’s a jerk.“

But the problem is when you first get to a new country, it almost feels like every person you encounter is representing the country because you’ve had so few interactions in this country. So first, try to integrate.

Second, try to not accidentally generalize. Know that if one person is rude to you, it’s just that person. Then, try to assume that the way that you grew up is wrong and that their way is right. Because otherwise you’re going to do the reverse. You’re going to assume, ”No no no! Everything’s wrong. The way that they’re paying their bills, the way that people are are chaotic at the bus. It’s wrong! People should line up in an orderly fashion.“

Whatever you think, say to yourself, ”Hold on. Maybe the way I grew up is wrong and they are right.“ You have to psyche yourself into that mindset so that you can try to understand and try to assimilate and not keep them at a distance. Integrate until you find yourself saying ”we“ instead of ”they.“

Ideally stay at least three months. Make local ties, friends, and fall in love.


I like that a lot. I’ll be using some of this advice for myself because I’ve never heard someone talk about it in that way and able to break it down so well.


If you’re under 30, and you’re listening to this, go before your 30. I don’t know what’s up with the number 30, but all around the world, so many countries make it dead easy to get a work visa if you’re under 30, but much harder to get one if you’re over 30.

First, you can just go on a tourist visa for three or even six months. You can almost always go to a country for three months and then you can just leave and come back again for another three months. Almost any country will let you get away with that.

If you want to integrate and stay more than six months, if you’re under 30, you can usually get a work visa for young labor and then you can get a cool job working as a ski instructor, working at a hotel, or doing things like that where you can meet tons of other people in their 20s.

You get to really integrate because you’re going to be working alongside people that grew up there and you’re all going to go out together after work. That’s so much better than going to some place like Cambodia and sitting in a little bubble of other expats and not talking to the locals at all.

The most important thing is to go, but the second most important thing is that you try to integrate and assimilate and not stay in your little bubble where you party with other expats.


That’s awesome. It’s real, actual advice. I didn’t know about that work visa part of it, but it does make sense to be able to give you a license to go for longer periods of time. Part of the big question mark for most people is the cost.


Imagine this: You’re 27 listening to this, and you figure out some way to get a work visa to. . . Pick a country in Europe.




You get a work visa to go to Germany because you’re 27 and it’s easier if you’re under 30. Now you’re in Germany, and imagine this: You stay for five years. You start to learn some German and now you’ve been a resident for five years. Most countries will make you a citizen if you’ve been there for five years.

Now you get a passport. So now you’ve got a German passport along with whatever one you grew up with. Once you’ve got a German passport, now you have the right to live anywhere from Iceland to Italy, from Ireland to Spain.

You have the legal right and that stuff passes down to your kids automatically. As soon as your kids are born, they’ll immediately have a German passport. Depending on their gender, it passes down to their kids. All because you spent five years there back in the year 2020.

If you thinking long-term and multi-generationally, it makes so much sense to go, especially when you’re young. Go integrate, go stay somewhere else, go get out of your home country, expand your mind, learn a different way of approaching the world, learn that things are not so black and white and that there are multiple ways of approaching anything.

It’s not that one way is right and the other ways wrong, but there are multiple, correct ways to approach anything. Then you get these other benefits. To me, to be a real world citizen is to have the legal right to live places, and that comes through legal residency, legal citizenship, and passports.


That’s really cool. Being a citizen of the world is going to be more and more important as with this connectedness with the Internet. We’re able to blend cultures. This conversation is an example of that — being able to call someone across the ocean and I’m here in the Midwest.

That goes to show how important it is to be able to understand other cultures. It’ll help you navigate the world as it gets more complex.


If we’re talking 20 years ago, it would’ve been different. 20 years ago, it felt like the trend was towards globalization. Now it feels like the trend is towards tribalism.

Putting up stronger borders. It’s more of this ”us vs. them“ mentality. I think it’s even more important to deliberately counteract that.


I truly think there are more common values across people than we’re lead to believe. It’s worth deconstructing those those boundaries and asking, ”How did you grow up?“

If you take the thematic values of how someone grew up, even China versus the US, it would be more or less the same. The same value structures, parents, that kind of stuff. It’s worth highlighting the commonalities. Getting exposure to it is even better. It leads to my next question.

You talked about this at the end of one of your blog posts. You said don’t confuse the medium with the message. Don’t confuse the tool with the goal. Don’t confuse the vehicle with the path.

I think that’s really similar to how people tend to think about stuff. They overly box themselves in or they confuse the tool with what it does.


My little history at the beginning of the interview was that I was a professional musician that accidentally started a company. After 10 years of running the company, I got surprisingly lucky and sold it for millions.

People who met me after that assumed that I was some kind of stereotypical entrepreneur and they’d start talking to me about their angel round finances, their Series A, and blah, blah, blah. All of this stuff that I had no knowledge or interest in.

But I could see how somebody would just assume, ”OK, you sold your business for millions, so you must be this kind of person,“ but it’s not at all true. The truth is, I didn’t even want to start a business. When it was too late and my business was growing, I absolutely was not doing it for the money.

People ask my advice on how to grow your business and they look at me strangely when I say I never tried to grow up my business. In fact, I was trying to keep it smaller than it was. I was actively trying to prevent its growth. It was growing bigger than I wanted.

And they don’t even know what to do with that. So the reason I say this is because I think we need to drop our assumptions. Don’t assume that the common pairing is always true. Don’t confuse the media with the message. Don’t confuse the tool with the goal. Don’t confuse the vehicle with the path.

In those cases, what I’m referring to is my company. My company was the media, the tool, the vehicle. But don’t assume that I’m interested in business, or profits, or investors, or any of that stuff that goes with it.

You see this in other professions, too. Someone could be a politician because they’re greedy and they want the glory, or someone can be a politician for very selfless social justice reasons. You can’t assume that musicians are necessarily creative, heart-driven people that live their life in chaos and sleep until noon every day [laughter].

Acknowledge the stereotypes first, but then break them because they’re often not true. You need to disconnect the outer action, the appearance, or the profession with your assumption about that person’s inner motives. The outer appearance doesn’t tell you anything about the inner motives.


I agree. Stereotypes are useful because they give us context on how to act easily in complex situations, but to do that for everybody is is a little disingenuous.

Everybody doesn’t do the things they do for the same reasons. That’s why I wanted to unpack this because the distinction between the medium and the message is so cool.

Just because you’re using a certain medium to convey a message doesn’t mean you buy into all of that baggage [laughter].


[Laughter] Right. Here’s the funniest example. I told you I lived in Santa Monica on the beach. I don’t know if it’s still true now, but when I was there, it felt like every single person in Santa Monica was really into yoga.

They wouldn’t just do yoga. They would start doing yoga and then decide to buy in wholeheartedly to the whole thing. They’d start saying ”namaste“, they’d put up little yin and yang things in their house, and they’d only drink de-ionized water. They would even sometimes talk in a certain tone of voice.


Melodic sounding?


Yeah! You didn’t speak like that a few months ago, but now because you’re doing yoga, you’re putting on this voice? Some people feel a need to buy into this whole thing.


That’s over-assimilating.

People’s identities become a little too malleable, right? They buy into a certain image and they let that take over their entire identity. I try really hard to not mentally look at what I do and say, ”OK. This is not because I’m an engineer. It’s a part of me, but it doesn’t inform the “I am.” Everything I am is internal and what I choose to do is that outward manifestation of those things.

We’re all more complex and dynamic than any role we choose to fill. It really helps to have that identity foreclosure and keep it at bay. We tend to attach to things, especially the things that we get accolades for. I used to do this a lot, especially growing up.

You see the certain ways that you are and you see other people who aren’t like you and they get praised for things, and you think, “Well, I guess I’m just this nerdy guy in the corner and I don’t know how to be that person.”

You box yourself in slowly but surely and all of a sudden you realize, “Oh, I’m the one who put these borders around myself, not the other way around.”

To keep building on stereotypes, but getting a little bit broader by expanding to gender stereotypes, you had a really cool blog post about how you tend to look at stereotypes between genders and treating them more or less the same, even though they’re not.

It was a really good way of cutting through the B.S. that a lot of people get hung up on. You also mentioned that you have more female best friends than male as well. I would love to unpack this, too because it’s one of those things we talk about in society and it’s a little eggshell-y feeling and I’d like your take.

Sure. Why I have more female friends than male might just be an accident of history. When I was 12, there was this girl, Sharon, that I sat next to in junior high school in Hinsdale, Illinois.

We were best friends and we did everything together, and we were absolutely not at all attracted to each other. She was just my best friend for years and then she moved to Italy. Then another girl became my best friend. I think it kind of became my norm. Who knows? Formative years.

Because of it, there’s something that’s always been a pet peeve of mine. It’s always annoyed me when my friends say things like, “You know how men are,” or “Women are always. . .”

Every time somebody says that, they say it about the opposite gender, and it always feels wrong to me — just factually wrong. They say, “Well, you know how old men are.”

I think, “No, that’s not at all true from my experience.” If a female friend says, “Men are never good at explaining how they feel.”

I say “Actually nobody’s good at explaining how they feel. That’s a human thing, not a male thing.” Usually, when I say that, whoever I’m talking to has to acknowledge, “Yeah, OK. You’re right.” [Laughter].

It was really interesting when after a few years of this annoying me, I read a book about social psychology, where social psychologists found that the differences among men and the differences among women are much greater than the average differences between men and women in general. At the same time, they found that we we all have a natural human nature to tend to exaggerate the differences between groups.

You could say the same thing with race groups or nationality groups, and in this case, gender groups. We tend to exaggerate the differences between groups in our own thinking. Unless you’re a stand up comedian in which case you do it on purpose for a laugh [laughter]. If you want to think clearer, then you need to to deliberately de-exaggerate the differences.

I like to take that all the way and say, “OK, if my human nature is to exaggerate the differences between groups, then I’m going to take it all the way the other way, and overcompensate.

Assume there is no difference between the groups because I know that my human nature will compensate. I think of the metaphor of throwing a Frisbee. If you’ve ever played catch with a frisbee for a while —Ê[laughter] I’m sitting here making the movement with my hand — I find out that every time I throw that frisbee, it bends all the way to the left.

Every time I throw it, I try to aim exactly to my friend. It goes way off to the left. From now on, I’m going to aim over there to the right because I know the Frisbee will bend to the left and then it’ll actually go where I want to go. So now I don’t aim where I really want to go. I am way off over here knowing the Frisbee will correct itself.

If you’re thinking about the difference between your group and another group, whether it’s gender or race or whatever, assume there are no differences and that men and women are the same. Then your natural human tendency will help find the sweet spot, or find a more correct point of view.


I like that. It shows through with a lot of the stuff we’ve talked about. When it comes to travel and working in different domains professionally. Try not to carry your assumptions too closely, right?

Because it usually is not the right lens at the time, or you’re going to assume too much. You’re bringing 10 pounds of crap along with the one percent that’s actually good [laughter].

It cuts through a lot of apprehension that people feel when when dealing with things, like professors having to deal with more questionable situations. I like to talk about the stuff that helps people be more even-handed in general because it doesn’t need to polarized.


I left America 10 years ago, and I hear that some stuff has happened since then. In that same social psychology book where they talked about the differences between groups, I’m going to quote this wrong, but they put out a study where they asked Democrats what they felt Republicans wanted the tax rate to be, and they vice versa with Republicans. Then they asked afterwards, now what do you think? What do you want the tax rate to be? Where do you stand on this issue?


What they found is that each group thought that the other group was way different from their own standards. I specifically remember the tax rate one because each group thought the differences would be around 40 percent, and the actual difference between Republicans and Democrats was four percent.

I think this went for some other issues, too, not just tax rates. To me that’s the classic case where people assume that the other side is so much different than them. ”Ohhh those people. Those idiots want it to be sooo wrong!“ If you actually talk to people your differences aren’t that big.


You have a 10x margin of error in your assumption [laughter].


Maybe that’s why I think it can be so healthy to leave your country for a long time and get to know other points of view.

I’m going to use America for the first example, but this goes for anywhere. The differences between groups inside America feel huge.

But if you move to India, now basically all Americans are about same. In relative comparison, Republicans or Democrats, it’s basically the same when you compare it to the outside. The same thing goes in all places.

It’s funny that if you ask people from Korea for their opinions on people from Norway, they’ll probably say, ”I don’t know. People from Norway seem fine.“

If you ask them about the Japanese, they’re like, ”Oh the Japanese! Let me tell you!“ Koreans are focused on the subtle differences between Koreans and Japanese, but they seem amplified and huge to them.

Then if you ask somebody from Sweden about the differences between Swedes and Norwegians, they say, ”Oh, those Norwegians! They’ve got a stick up their butt. They’re just too formal.“ When the truth is, they’re about the same.

I think we focus on these small differences with our neighbors and we over-amplify those because they’re so easy to put our finger on. When you step away from that, you move all the way across the earth, it gives you a better perspective on being where you came from.

You see that you did not come from the center. I’m picturing the metaphor of the center of a flower, the pistol, and all the petals on the edge. We tend to all think that our position of where we grew up is like the center of things. Those people are over there and these people are here, but I’m in the center.


The ”I know what’s better“ mentality.


Right. When you leave America, you get into other mindsets. Then you realize like, ohh none of us are in the center. We’re all off on one of these petals.


It reminds me of Tim Urban who’s writing this really long, multi-part thing right now. He talked about this idea of how people think. He’s got the scientist who’s the top rung — higher level thinking where they’re always testing their hypotheses or ideas.

Then one rung down, there’s this idea of the sports fan. Basically, everyone has their team or idea that they’re rooting for and most people tend to think this way where they have a hypothesis and they want a certain thing to win.

Even in neighboring cities right here in the Midwest, you have the Packers versus the Bears as this huge rivalry. It’s high time for football season so everyone’s in sports mode right now, which I could care less about, but you see all these people who are really into it.

There’s that thinking again. People tend to do this across borders, across neighborhoods, across whatever it is. It’s really cool now that I’m thinking about it like this. The way you explained it is adding more to that metaphor for me.


I was actually with this girl for about six and a half years from Sweden. She was from the west coast of Sweden from a city called Gothenburg. We went back to Sweden together many times and I always wanted to go to Stockholm. She said, ”I’m not going to Stockholm. Stuck up Stockholm. Really hate them. They think they’re better.“

It was only two hours away and she refused to go there with me. She just hated them. ”Stupid Stockholm people.“ Years later, after we broke up, I went back to Stockholm and it was wonderful.

It’s just so funny these little tiny territorial things where someone is amplifying those differences. There it is again. We tend to amplify the differences between groups.


It’s worth highlighting these things so people can at least question them. I like pushing people to question the things that they haven’t stopped to think about, especially sports.

Sports teams or cities you live in. You get indoctrinated at birth to assume certain things, and it’s not until you have a chance to distance yourself from the people around you that you can actually say, ”Hmm. Why do you really believe that? Is that even my belief or is that just something that my parents or my hometown has drilled into me?“

I know you don’t want to go too deep into this, but you mentioned you have a son, and he’s taught you how to be more curious about stuff.

Parenting is a really interesting domain philosophically because of it’s the one job we can choose to have where no one checks your credentials. You are figuring out as you go along.

Do you have any higher level thoughts about raising a child? How would you have your child be exposed to the ideas we talked about today?

Or if we wanted to go more broadly and not talk about your child, but you’re mentoring maybe a high school student.


So it’s kind of a two part question, and I’ll combine the two. I don’t really have that much to say about parenting because I’ve found that it’s so situational.

I have friends who have three kids where two of them are total angels and one is just Satan [laughter]. So I think that for a surprising amount of who people are is just DNA. It’s just their nature. It really surprised me. Nature versus nurture.

I used to think it was an entirely nurture. We are who we are based on things that happened to us.

But it’s really interesting to see how much of it is probably just DNA. My kid is just awesome. He’s great. Being with him for me is like meditation. I just shut down myself. I shut down my needs. I shut down my ambitions. I just kind of turn it off.

I also turn off the computer. I turn off my phone. I just give him my full attention without distractions and enter his world. When we’re together, he leads and I follow. That is my complete and total parenting technique. That’s it.

So the second part of your question was about encouraging a child to explore the world. Being a guide and not like forcing him into something. I see a lot of parents who think, ”This is what I wanted to do in my childhood. So I’m going to make it so that my child has those things, too,“ even if their child is showing all the outward signs that they don’t really care about those things.

Truth is, I do — despite what I just saidÊ— definitely do some of that. I do nudge. I believe that anything that he’s physically capable of doing, I let him do himself. I have a parenting opinion in favor of self-sufficiency and independence.

Then again, that’s a cultural thing. In India, especially, I’ve seen some kids as teenagers that are still completely helpless and dependent on their parents. They don’t know how to make a meal. For example, when he was five, we lived in a neighborhood in New Zealand that I trusted, so we often went to the corner store together, which is just across the street. One day I just decided OK, I think he’s ready. I gave him some money to go across the street by himself to our usual corner store to get himself something and come back home by himself.

I watched out the window and he did it. The guy at the store knows him, and it was cool. He went in, did this thing by himself. When he was six, we were living in a different neighborhood that was more of an enclosed cul-de-sac. It was totally safe. No through traffic and there were some other neighbor kids.

So I let him run off with the neighbors for an hour at a time. I didn’t know where he was, but I knew that he was in the vicinity. I didn’t worry. Just last week, at the age of seven, I was in the kitchen making breakfast and he started a fire in the fireplace without me knowing it.

I was surprised. I walked in the room and was like, ”What the hell?“ [Laughter], but he knew how to do it carefully because I taught him how.

With each of those examples, there was some preparation, yes, but the biggest hurdle was the trust. I had to just trust. There was an optimistic trust that everything’s going to be OK. It was a little scary, but I figured that was my problem, not his.

I don’t want to project any fears about the world onto him. I want him to believe that the world is not scary. I want him to believe that he’s capable and he can do this. I’m not gonna do that overprotective thing, ”Oh, no, no, no, no, no, no, no. Don’t do that! No. Stay with me. You are not safe without me.“

That’s a completely valid cultural difference where I’m choosing the opinion that I just said, but I know plenty of people, especially like I said in India, that do the opposite and they’re not wrong.

I’m not saying I’m right and they’re wrong. I know plenty of other people that completely shelter their kids as long as possible and that’s also a perfectly valid technique that probably grew out of certain scenarios. But for my scenario, for him, for us, for me and him, I teach him the opposite.

I want to teach as much independence as possible. Teach him how to make a fire, teach him to be careful, teach him how to do everything he can by himself.


Thanks. There’s no right or wrong answer here, and I think you’re making that very clear because it is not one size fits all. It also depends on the situation, but I think it’s worth highlighting because it’s just such an important job and it’s worth highlighting how other people go about it without judging.


There are other parts in our conversation today where I kind of stopped and said, well here’s my advice. Move to Singapore [laughter], but when it comes to parenting, I’ve got no advice. That’s what I meant about the DNA thing. I don’t know who your kid is. Nobody knows your situation but you.

It’s different for everyone. It’s like love relationships. A stranger said, ”Can you give me some relationship advice?“ I said, ”No. Because I don’t know you. I don’t know your relationship.“

I feel the same way with career advice. I usually would probably say this at the end of the interview, but I still read and reply to every single email I get.

I always encourage people, especially if they’ve already lasted 90 minutes into a podcast interview to go to my site,, and my email is in big letters there. Just click it and send me an email. Say hello. Whether you want to ask me a question or just introduce yourself.

The thing is, sometimes people that I’ve never heard from before will send me a two sentence question. They say ”Hey I don’t know if I should quit my job or not. I’m thinking about maybe starting my own business. What should I do?“

I think, ”I have no idea. It depends. Who are you? We’d have to sit down for two hours for you to tell me everything about your background and your scenario. I’m not going to give blind advice. It all depends on who you are.


People look for external influences to give them a reason to jump when there’s so much to unpack.

Does it make sense for you to do such a thing? I feel the same way when people you see on Instagram give workout advice or stuff like that and ask people to follow their program.

It’s super general and it just seems so crazy to me. All you can do is say, “Hey this seems to work for me and maybe if you do it, it might work for you, but there’s a good chance that 90 percent of it might not work.”

Let’s go back a bit further to a different topic. You had a thing on your website that you’re an INTJ. You highlighted that you’re an introvert. I thought it was interesting that you decided to put it in there, since you don’t categorize super heavily.

So I thought it would be a little fun to unpack. I tend to be an INTJ too. Maybe it’s my engineering stuff, just collecting data, but I love to take these personality tests and overlay them on top of each other and see the patterns. I’m curious if you have any thoughts on these personality type tests.


I put INTJ on my site because it’s one of those things where 20 years ago, I took the little Myers-Briggs test and I answered the 50 questions, and afterwards it said, you are an INTJ. I said, “Alright,” so I read the description and thought “Oh, wow. Wow. Yeah. This is weirdly accurate. Huh? That actually kind of freaked me out with how accurate that was.”

I could sit here for five paragraphs and tell you some stuff about me, or just say click this link about INTJ. I fall into this category. This describes me. So I think that was just a little shorthand to say here’s something about me. If you don’t know me and you’re thinking about contacting me and you’re going to ask me if I want to come hang with you at Burning Man, the answer is probably not. Here’s why [laughter].

What’s more interesting about these kinds of categorizations of introvert and extrovert is that it helps me understand other people. I couldn’t understand why anyone would want to run a marathon on the big day with all the fuss, and the noise, and the crowds, the clipboards, and the walkie talkies, when they could have just done the exact same run by themselves the day before.

They could have had a wonderful, peaceful run. They could have had the road to themselves. Why would anybody choose to do it at the same time as everybody else?

An extrovert explained to me that they get really charged up by having all those people around. I said, “Oh, really? You actually like having other people around?” They said, “Yeah. It’d be too depressing and sad to do alone. I wouldn’t do it by myself. You get a whole bunch of other people around, and now I want to do it.”

I said, “Oh weird. I’m the exact opposite.” I would be ten times more likely to run a marathon if I got to do it all by myself. If I had to do it in a crowd with other people. No, just no way. Count me out. No interest.

We talk about introvert/extrovert a lot, but talking about how people look at time focus. There’s a fascinating book by Phil Zimbardo called The Time Paradox. He’s a Stanford University psychologist. He’s kind of a legend.


He did the Stanford Prison Experiment.


Yeah. He’s most famous for that. My favorite thing of his was The Time Paradox because he pointed out how some people are mostly present-focused where they think that today and this week tops. Anything past this week is off the radar. Whereas, there are people who are very future-focused and think hardly anything of today.

Today is just lived in service of their future self. He even talks about past-focused people. Some people mostly live in the past. Whether positive or negative, whether nostalgia past positive or people who are constantly in a state of haunted PTSD, which is past negative, they can’t let go of the past.

That really helped me understand some people in my life. It made no sense to me before. Once I was able to categorize myself, I said, “Ohhh, yeah, okay. Future-focused. This is describing the way I see the world. Now I understand.

Some people really just open their eyes and look at the world in a completely different way because they’re looking through a different time lens.”


That’s cool. I’ll have to look into that book.

Alright. We’re gonna go on to your personal philosophy.

You self-discovered minimalism and stoicism, and then had a realization that you hadn’t created it on your own. There is this whole area of philosophy that had already been around for 2000 years.

I love stoicism. It’s one of my favorite ideas that I’ve run into and it helped me get into mindfulness and meditation. I’d love to unpack how you think about that stuff. It shows through, especially with how you write because there’s no extra fluff between your words.


Stoicism. I don’t know why I think the way I do. It might be kind of situational. I mentioned that ever since I was 14, I knew I wanted to be a professional musician and because of that, I was expecting my life to be hard.

I knew I was never going to have a job. I was never going to have a pension or health insurance or any of that stuff. So I knew that this was going to be a hustle. I knew that wanting to be a successful musician is like wanting to be an Olympic athlete. Millions want it. Only a few get it.

So my whole approach to life ever since I was 14 was to constantly prepare myself for a more difficult future, which means never choosing the luxurious choice. Always choosing to be deliberately hard on yourself and to keep yourself tough so that even if times are not tough right now, you’ll want to be prepared for when times are touch in the future.

That’s been my approach — maybe because I wanted to be a successful musician or maybe it goes back to the nature versus nurture DNA thing. Maybe this was just in my DNA to approach life like this. Maybe I shouldn’t even be crediting it to the fact that I wanted to be a musician.

I never knew anybody else that approached life like this. I was the weird one.

In fact, it’s a big reason why when Tim Ferriss and I met back in 2008 in San Francisco through a random acquaintance, we totally hit it off.

I think because of this thing, we just looked at each other. We had the “Oh, you’re like that, too? I’ve never met anybody else who thinks like that!”

We had this weird approach to life in common. Later when I was 40, I read a book about Stoicism. I kinda avoided it because it sounded like boring ancient Greek stuff, but a few people recommended this book and it had a whole bunch of five star reviews so I thought, “OK. I’ll check it out.” It was called A Guide to the Good Life by William Irvine.

Reading that book, I thought “Whoa! Holy crap! This ad hoc approach to life is a philosophy that these ancient Greeks came up with 2,000 years ago and it has a name with an -ism on the end.

This is so weird! I thought this was just me. My weird approach to life, turns out it’s an -ism.”

You asked how did I feel realizing I hadn’t created something new, but I wasn’t trying to create anything new, I just thought that I was the only weirdo who approaches life this way. So to find out that there are other ancient weirdos who pioneered it and that it’s supposedly a desirable way to be, that was nice.

Like that yoga example we gave earlier. I don’t just buy into a group or an -ism. I don’t subscribe to -isms. Just because I believe something doesn’t mean I need to buy into the whole thing.

Even with stoicism, I ended up reading maybe two or three books about it and I got some good insights, but that’s that. I’m not going to go say I am a Stoic. I believe in stoicism. I’m not saying this is my life philosophy. I think that I agree with a lot of things, but I don’t buy all the way in.


I agree. It’s funny that you thought that you were the only weirdo. It wasn’t until I listened to the Tim Ferriss podcast and he kept talking about it, that I thought, “Yes, I do believe in this. Huh, I guess I didn’t know it had a name.”

Because it does seem like we have some natural orientation to believe a certain way. It’s quite interesting when you discover that and say, “This is how I am, but it’s also got a name and a thought process?” It is a little strange.

We’re getting close to the end here and it’s been a through line for this entire conversation. You mentioned being able to keep yourself from holding your beliefs too tightly. That’s such a huge thing to be able to to check yourself on. This entire conversation has been a reminder to do that for everything you do.


Not only do I not hold on too tightly to my views, I would say I hold on too loosely.

I think I’m extremely disloyal to my past self almost to a fault. When I had employees at my company, they found it annoying. Sometimes they’d yell at me for changing my mind. Well, that’s what learning is [laughter].

Whenever I learn more, I update my world view. Whether it’s through reflecting or reading a book, at some point I learn something that gives me a new perspective on something I’ve been doing before.

Even if it invalidates everything I’ve ever said or done in the past, that’s fine. I don’t mind. I don’t care if people think I’m flaky. At the beginning of our call, we talked about the how I lived on the beach in Santa Monica and I had no interest in travel. I was like, “Travel? What?! Are you nuts? Why would I travel? I live in Santa Monica, California. Best place in the whole world. Why would I ever want to be anywhere else?”

Six months later, I said, “Yeah, I’m going to leave America and never come back.” I learn, and if it is the opposite of everything that I said, that’s fine.

In fact, I think it’s pretty cool. That means that I’m learning and changing, and that’s ideal. So I think we all have our value systems. Some people strongly value loyalty. Loyalty to their country, to their neighborhood, to their beliefs.

You decide where to put loyalty. I’m very loyal to my kid for example. I’m loyal to the core for my kid. I’m not going to change my mind about him [laughter], but be very judicious with where you decide to apply your loyalty. That’s just me.

On the other hand, it’s my top value, or near the top for me to challenge my old beliefs and make sure that I’m not stuck with some old belief out of habit.

I’m constantly taking things that I believe — trying to replace it with a question mark just to see. Take anything that you would put as a belief statement. Write down your top 10 list of beliefs, what you think is important to the world, and now put a question mark at the end of them [laughter].

Can you see another point of view? Can you see a world where that’s not true? Where in fact the opposite is true?

I enjoy thought experiments. I find it very exciting to consider that the opposite of what I believed yesterday might in fact be true. It’s like going on a journey in your head.

That’s a fine place to end a conversation. Thanks, Erich.


That’s awesome. It’s hard to describe you, but I’ve been talking to some people and I say he’s like a philosopher-poet-musician. It’s weird [laughter].

It’s awesome. Thanks for doing this and for giving us your undivided attention. You’ve already mentioned where people can connect with you, but if you want to reiterate real quick?


Go to my website Everything I’ve ever published is there. Even all of my tweets. I put them on my website first and then echo them to Twitter if I feel like it. Point is, there’s a big link there that says “Contact me,” so anybody listening here, drop a line and say hello.


Awesome. Thanks, Derek.


Thanks, Erich