Derek Sivers

Interviews → Future Thinkers / Mike Gilliland and Euvie Ivanova

Really fun conversation. Lots of topics I rarely talk about. Building your values, learning and growth, How to Live and my directives, leaving a legacy through what you create, being a life explorer, minimalism

Date: 2020-02

Download: mp3 or mp4



Hi everyone, our guest today is Derek Sivers, a writer, programmer, entrepreneur and former owner of CD Baby, an online store for independent musicians.

Today, we’re talking about building a life around values such as learning, growth, and minimalism and exploring freedom to its extremes.

Welcome to Future Thinkers. A podcast about the evolution of technology, society and consciousness. I’m Mike Allen.


And I’m Euvie Ivanova.

It’s really cool that you’re coming out of your recluse years, it seems.

I’d love to hear about what you’ve been up to.

You’re working on three books right now. One of them is called, “Hell Yeah or No,” which is a title that very much speaks to us. I’d love to hear about the philosophy behind that approach to life.


We tend to say “yes” to too many things. Because of this, we’re spread too thin. We’re so busy doing average things that we don’t have time for the occasional great thing. So, I propose raising the bar as high as you can so that if you’re feeling anything less than, “Oh, hell yeah, that would be amazing,” then just say “no.”

By doing this, you will miss out on many good things. But that’s okay because by saying “no” to the merely good things, you’ll have the time, energy, and space in your life to throw yourself entirely into that occasional great thing when it comes up. That’s it.


I imagine the comment section for that could get pretty ugly. What kind of responses do you get to that idea? And how do you respond?


I only feel the need to correct people when they try to apply this rule to everything.

I’ll get an e-mail from somebody that says, “Yeah, I’m just out of college and looking at a bunch of job offers. But man, none of them are a ’hell yeah.’ So, I’m saying no to all of them.”

I say, “No, no, no, no, no, hold on. This is a specific tool for a specific situation. It’s when you’re overwhelmed and you have too many options. That’s when you use this tool. It’s not meant to be used for everything in life. You need different strategies in different stages of your life.”

If you’re at the beginning of your career and you’re trying to discover where your lottery tickets are going to hit in life, then it’s a better strategy to say “yes” to everything. That’s because it’s some skill and some luck,

It’s usually after somebody gets successful that they’re drowning in opportunities. They say that most small businesses don’t die of starvation. They drown in opportunities because they say “yes” to too many things.

When you’re successful at something, when you’re overwhelmed with opportunity, then you use “hell yes or no” as a decision-making tool to keep you focused.


I’m really glad you made that clarification. Attached to my screen are a thousand sticky notes of all the things I have to do [laughter].


To me, it’s about constantly asking yourself what’s really important, what’s necessary, and then getting rid of the rest.


I’d like to hear about an idea that you’ve talked about recently, the one about building your life around your values.

First, how you pick the values that are important for you, understanding that they’re going to be different for everybody at different stages in their lives?

Also, I’d like to hear about some of your experiments in arranging your life around those values. How they’ve gone well, maybe how they have completely gone wrong, or when you had really unexpected, ridiculous results.


First, I should say that I’m not looking for a normal life. A lot of my friends often say, “Why do you feel this need to be so all or nothing or so black or white?”

It’s because I like exploring the extremes. I think it’s more honest. And here’s why.

When I realize that one value has a higher priority than another value, I ask myself if I’m living accordingly. If I say that my kid is more important to me than my phone, it’s one thing to say that, but if I’m on my phone when I’m with my kid, I’m lying with my actions. I’m living in incongruently.

I’m saying that my value hierarchy is like this, but my actions are proving otherwise. I feel the need to sort that out. Is my phone actually more important to me than my kid? Was I lying about what I said? If not, then why are my actions not in line with my beliefs?

I’ll do some daydreaming or journaling, and I’ll figure out how it would look if my actions were in line with my beliefs. Usually, I take each belief system to its logical conclusion. I enjoy taking it all the way. I say, “If that’s really true, then. . .”

In that tiny example, I decided that anytime I’m with my kid, I’ll just keep my phone off completely, or put it in airplane mode. I will not touch it when I’m with him. He is always more important than the phone.

But let’s pick a more interesting, nuanced topic. If I say that learning and growing is my top value and very important to me in life, but I’m living in a comfortable house in a familiar neighborhood, with a nice fire in the fireplace, in a neighborhood full of people like me, I have to ask myself, “Is this congruent with my values?”

I’m not sure I need to explore that. I could be living in a slum in Mumbai and having more of a learning and growing experience. But would the friction of that cause me to grow less in other ways? Would the friction of daily life slow my learning growing progress in other ways? Or would it actually enhance it?

Sometimes I’ll go experiment with these things. I’ll live somewhere very uncomfortable and see how that does with learning and growing. Maybe I don’t want to move my whole life just for an experiment like this, so I’ll just daydream about it.

That’s a better example of how I’m always wondering and exploring and experimenting. Maybe it helps that I’m not just willing but enthusiastic to try living an extreme life. And that’s in accordance with my values and beliefs.

I don’t think I’ve ever explained that to somebody before.


What are some experiments that you’ve done where you voluntarily threw yourself into uncomfortable, unfamiliar situations to see what would happen?


I’ve moved a lot. I married somebody I just met to experiment with the idea of commitment. I moved to Singapore with one suitcase to understand a different way of looking at the world. The Confucian values of living in Asia are so different from my individualistic American values that it took me a while to adapt to that lifestyle.

If I find that I’m too loyal to the self-definition of being an introvert, I feel the need to question that. I like to break loyalties and question things that I think are true. If I find that I believe something too strongly, it makes me want to try going against it to see what happens.

So, I’ll go be an extrovert for a while. I’ll meet with everybody and be around people all the time and experiment with that. I moved to New Zealand to experiment with six years of solitude – not solitary confinement in a jail, but relative solitude compared to the rest of my life.

I’ve had a minimalistic life for so long when I moved to Oxford, I experimented with the opposite. I got a house and I furnished it. I got a car and all that kind of “stuff” that I thought I would never have. I have a stocked kitchen now. It’s really weird for me. I have a cutting board. I’ve never had a cutting board before. I’m experimenting with it, and I’m not sure I like it.

I think I might give away everything again next year and go back to what feels more honest to me, which is to have only the things that I use every single week. If I don’t use it every week, I really don’t need it.


I’ve noticed that there are a lot of people who’ve made a business, had some success with it, and then fallen into a kind of existential crisis of, “OK I’ve done this. Now what?”

I’m wondering if that was the case for you as well?


I think it’s because you have a blank slate. It’s because you have the time.

An ex and I were talking about the fact that I write in my journal for one to three hours a day. I’m often daydreaming possible futures and other things I could be doing with my life. I’ll often write about these kinds of things. And she said, “Have you always been like this?”

I said, “Yeah, always,” and I had to stop myself and ask, “Wait, have I always been like this? No.”

It didn’t start when I sold the company, but when I was free to work on other things. A year or two before I sold the company, I was the owner, but I wasn’t required to be anywhere or do anything. I think that’s when it started because for the rest of my life, up until then, I was very head down, very focused. I knew exactly what I was after.

I was on an absolute laser-focused mission for 24 years. From the age of 14 to 38, I was pursuing one single thing – first music then CD Baby. Then at 38, I sold my company, CD Baby. Suddenly, I was free of it. It felt like this huge blank slate.

My first impulse was to do more of the same. The day after I sold my company, I woke up and as I was making breakfast, and I went “Oh! I just had an idea for my next company!”

I immediately dove into that. It was called Muckwork, and I spent the next three or four months programming it. I hired a manager. I dove into it and thought, “This is my next thing! I believe in this completely.”

After four months, I had to stop because I realized that my trajectory would be exactly the same. I would take one company name off my mantelpiece and put a different company name there.

But my actions and my life would remain exactly the same. I realized, “No, no, no. I want to make a real change.”

That’s when I started with this blank slate approach to life. That’s when I started the habit of deliberately saying “no” to all the things I used to say “yes” to and saying “yes” to all the things I used to say “no” to. It was a deliberate squelching of previous habits.


There are so many parallels with this, like minimalism and deconstruction work. Did you actually have that existential crisis at some point after?

At some point, did you have a breakdown and say, “This is not what I’m doing anymore. I’m changing as a person.”


To me, it was asking myself, “Is there such a thing as too much freedom?” This is what I asked myself in that last year of owning my company when I was no longer necessary.

I was the owner. It was very profitable, but I had completely delegated everything, and they didn’t need me for anything. I found myself asking these two questions:

What do you do when you don’t have to do anything, and you can do anything?

Where do you go when you don’t have to be anywhere, and you can be anywhere?

It kind of messed me up. I had a lot of money in the bank and I had broken up with my girlfriend a year or two before. I was completely free. Nobody was expecting me to be anywhere, and I had this bank account and this time. I could have started an ostrich farm in Mongolia if I wanted to, take scuba diving lessons in Iceland, or go learn Arabic in Egypt. It was too wide open.

Every day, I felt overwhelmed with all the different things I could be doing, and maybe that’s where this questioning of values came in.

You have to ask yourself, “OK, I can do anything. What are my values?” Sometimes you can do that just by asking yourself in your diary. You can say, “Well, these are my values,” but it can be more effective to look back at your past and ask yourself, “When was I happiest and why? What seems to be a constant thread through my past? What do I tend to like?”


What did you arrive at through the exploration? You mentioned your value of learning and growing that you hold that pretty highly.

Was there anything else that you noticed, any other threads?


Happy, smart and useful. This was a big one. I realized that whenever my life feels unsatisfying, it’s because I’m not satisfying all three of those. The intersection of what makes me happy, what’s smart – meaning long-term, good for me – and what’s useful to others.

It’s OK to do one or two of those, but I think if you’re not doing all three, something ultimately feels unsatisfying.

You could do something that makes you happy and smart, but if it’s not useful to others, it feels circular, self-contained. You can do something that’s useful for others and might be smart, but if you’re not happy doing it, it’s unsatisfying. We can try to talk ourselves out of happiness, but it’s the oil in the machine. The machine starts to break down if it doesn’t have that wheel of happiness.


Are you familiar with the Japanese concept of Ikigai?


No, I’ve heard the word, but I never found out what it means.


It’s pretty much exactly that. It’s a Venn diagram that is the overlap of what you love, what you’re good at, what you can get paid for, and what the world needs.


Oh, all right. Cool!

Damn! I thought I came up with that [laughter].


That’s another funny thing I’ve noticed. The more time you have to reflect, the more they all feel like brilliant, unique ideas.

Then you recognize that brilliant and unique people have also come up with those ideas, too [laughter]. It’s complementary.


I was 42 when I read my first book on Stoicism, and I went, “Holy shit, I thought it was just me! This is my quirky, weird Derek philosophy that I’ve been living by since I was 14 years old. This whole thing about making life deliberately tough on yourself to strengthen yourself for the unknown future. All this stuff is my quirky philosophy I’ve been living by and holy shit, it’s got a name. It’s got an -ism. It’s 2,000 years old. That’s amazing!”

It blew my mind to realize it wasn’t just me.


It’s really interesting to look at these kinds of patterns and insights and recognize how common they are in history. There’s something about it. It’s our common humanity. If you look deep enough into the abyss, it’s often similar things for people. In some ways, we’re not so unique. It’s very humbling in a positive way.


This was new to me – maybe you’ve known this forever – eyeballs evolved in nature around 40 different, unrelated times? If you look at a squid, their eyeballs are kind of similar to ours, but it’s not like we have some common parent with eyeballs.

No, no, no. It’s the idea that two eyes filled with liquid, a lens, and a retinol independently evolved 40 different times. Nature over and over and over again has decided this is a way to see predators and prey and get visual information. It’s reinvented the same way, almost over and over. That’s really cool.

I think about that with what you just said philosophically. You could sit all by yourself, completely disconnected from the world, come up with something, and find out that everybody else came up with the same thing. Maybe because it’s the logical conclusion.


We did an interview with Dean Radin who talks about real magic. He goes over experiments when animals and humans come up with ideas at the same time.

One example was a flock of crows in England. They all suddenly gained the knowledge to open the caps on the milk that was being delivered to everyone’s homes in the morning. Across the country, all of them learned it all at once.




You talk about your love for Stoicism and minimalism. How has that manifested in your life and what kind of things have emerged from it as a result of practicing those two things?

What have been some of the second order effects of choosing that lifestyle that might not be obvious for people?


When I look back on my life, minimalism is the common thread of what’s made me happiest. I get such joy out of seeing what I can do without.

The core idea of minimalism is this idea that stuff weighs you down. Often when we get something in our life, we think of the upside of it. But to me, I see the downsides more than the upside.

As for the second order effects, you may take things more seriously. You may consider the long-term impact of things, not just the environmental impact, but the impact on your psyche of having a thing. If I were to hang a clarinet on the wall in front of me, that would do something to my psyche. I’d think I should be playing that clarinet.

Everything in my late life feels like it should have some purpose. So, if it’s sitting there with no purpose, it’s like a little part of my brain is still spinning about that thing. You should let go of the unimportant to leave space.

Minimalist music has space between the notes. I think of that in my own life. Leaving space in my life. That’s kind of the “hell yeah or no” thing. It’s OK to leave your time and calendar empty because if you have space in your life, then you can go all-in when you find something great.

When you get rid of everything else that doesn’t matter, you really focus on the few things that are left.

I think it keeps you future-focused, too, because when you’re future-focused, you’re often doing things today in service of your future-self. You’re not living for today, you’re living for future you. Being minimalist means that the future you will have less to look after, less to maintain, less to store, less to upkeep.

Having less code today means less that your future self has to maintain and upgrade.

Having less baggage gives you more options in life. There are a lot of people I know quite well who would consider doing different things in their life, but they live in a big house with a lot of stuff and a big mortgage.

They have too much stuff that they’ve grown accustomed to. They think of too many things as necessities. They’ve reduced their options in life because they have too much stuff.

Two more. Having a small identity, instead of saying, “I am a programmer, rock climber, a musician, cyclist, Republican, Buddhist, French film fan, clarinet player. . .” That’s a lot of identity to maintain.

If you say I am these things, then that’s a lot of actions you have to do to uphold that identity. You can’t just keep saying that you are something if your actions are not supporting it anymore. You can’t say you’re a rock climber if you haven’t climbed rocks in 20 years. Identity can be baggage.

And lastly, a second order effect would be that you take more time to decide what’s important. You make real decisions about what’s important and what’s not. You decide what’s important and let go of the rest.

I do this every day. I constantly look at everything in my life. I think, “Do I really need that?”

I look at both physical and non-physical things. “Do I really need these things? Do I really need that identity? Do I really need that code on my site? Do I really need that functionality in my website? Are people using that?”

If not, get rid of it. “Do I really need all these old photos? Am I using them? Do I really like all of these things?”

That goes for goals, too. I hope I’m constantly letting go of goals. I look at past goals and think, “Do I need that goal anymore? That was something I wanted to do eight years ago and I haven’t done it yet.”

Even contacts. I constantly go through my phone and if there’s somebody I haven’t talked to in a year and I’m not desperately missing them, I delete it. My phone has around 25 contacts in it. That’s it. Which is wonderful.

Food. I get rid of food I don’t like. Sometimes I’ll buy food thinking, “I’ll cook something with that tempeh,” and it doesn’t happen.

Habits. There are some habits I do that probably started for a good reason long ago. If I notice that I’m still doing them, but they don’t have a place in my life anymore, I get rid of them.

My phone only has two apps on it because I realized I don’t use any other ones.

Sorry, that was a really long answer [laughter].


It was a really, really good one because you’re grounding it in very real-life things rather than keeping it abstract. It’s really useful for people because it gives them ideas of how they can do it in their own life if they’re considering it.


And maybe they don’t want to.

My sister, for example, is the opposite. She lives in a huge house with four kids, two dogs, and tons of stuff. That makes her happy. Just because somebody might be a fan of your podcast doesn’t mean that they need to buy into this. You can also do it in just one little aspect of your life.

I like it because it feels better to me to have less. At any given moment, I would rather be in an empty room than in a full room. I’d rather have an empty calendar than a full calendar. Some people are the opposite. They feel alive when their calendar is full, and they feel alive if they have a million contacts in their phone.

I like that space to grow, to change, and to focus. Also, I really like challenging myself to see what I can do without. The comfort I get from knowing and proving to myself that I don’t need something is ultimately greater than the comfort of having something.

It’s a greater comfort to know I don’t need it, so I’m constantly pushing myself to see what I don’t need.


When you remove all the stuff and there’s all this space, that space is a space of potentiality. What kind of things emerge from that? If every minute of your day is filled with meetings and things, there’s no space for that emergence.


I can’t help but think that this is applying so much to me right now with what I need to change [laughter].

I’m trying to focus on our interview, but I’m also like, “Fuck [laughter] Man, there are so many things I’m doing right now that I need to stop.”


Yes, it’s been a little bit the opposite.

We’ve added eight to ten new projects to our plate in the last couple of months [laughter].


It’s all an experiment.

It’s funny, I’d be the worst accountability buddy. I have a dear friend. She constantly wants to do that damn accountability partner kind of thing. She says, “Oh, Derek, I want to go on a diet. Will you be my accountability buddy? Let’s go do the diet at the same time and we’ll hold each other to it.”

I break loyalties every day. It can be something that I felt loyal to for decades. Just a few weeks ago, I gave away all of my music equipment. Everything. All of my guitars, keyboards, everything but this microphone because I thought it might have other non-musical uses.

I felt guilt every day about these two guitars that were sitting there that I wasn’t playing. I said that it’s an important value to me, but I wasn’t actually doing it. Every day, I felt like I should be spending more time doing that.

In fact, when I moved here from New Zealand to Oxford, England, I only brought one paper book. It’s still here. It’s called Great Songwriting Techniques by Jack Perricone, who was my old songwriting teacher at Berklee School of Music thirty years ago.

It’s the only book I brought with me because it was in my list of goals to get back into songwriting. I wrote 100 songs 20 years ago. I loved it. I still had this as part of my identity. I’m a musician. I’m a songwriter. This is me.

But three weeks ago, when I thought, “I really need to be spending more time on songwriting,” I caught myself thinking, “Yeah, but four hours writing a song is four hours I could be spending doing something else. God, I really need to let go of this whole music goal thing. I need to let this identity go.”

My best friend in Oxford is a full-time, professional musician. This is his living. So, I called him up and said, “Hey, would you like a couple new guitars?”

He said, “Dude! Are you seriously getting rid of your Strat? I want it!”

I gave him my Strat. I gave him my wonderful 88 key weighted keyboard and the synth with 20 gigs of sounds. He’s thrilled, and he uses it every single day. I even gave him my speakers. I looked at my speakers and thought, “I have headphones. I don’t need speakers.”

That was a huge identity thing for me to let go of that. I didn’t regret it for one second.

Shit. I even had a dog a few months ago and then my mom said she wanted to adopt a dog. I thought, “You know what? I don’t really need my dog. You can have my dog.”


I thought that story was going to have a much sadder ending [laughter].


I only had him for six months, but I thought I was going to have him for 12 years. He was a puppy. I looked at my life and realized that the dog was a hypothesis.

My mom and her husband were out there looking for that exact kind of dog. They were going around to dog shelters trying to adopt the kind of dog that I had. I thought, “You know what? I’m going to give you my dog.”

I have no loyalty except to my dear friends and family. That’s it. Even identities, habits, goals – no loyalty.


You know what I notice about watching you and listening to you is that you pretty much have a permanent smile.


Oh, sorry [laughter].


I think it’s reflective of these philosophies.


Well, we’re also talking about something exciting.

If you start to bring up politics or the “T” word, then, you know. . .but we’re talking about things I love talking about.


I’m really glad that you brought up the psychological aspect of stuff and attachments because I really agree with you. They really take up space in your head. They’re little notifications that pop up like, “Oh, I have to deal with this and I have to think about this.”

Especially with identity because it takes energy to maintain an ego. Because the ego has needs. It needs reinforcement. It needs validation. It needs boundaries. It constantly pings you to do things for it.


Right! What’s interesting is the word “stress.”

We often think of it in terms of distress, negative stress, but positive stress is called eustress. I thought that was a cool term to learn because there are many times where you want this as your identity because it gives you that eustress.

It actually pushes you in a way that you want to be pushed and therefore you keep that. It nudges you the way you want to be nudged.

But you have to keep asking yourself if that’s still true. It may have been true 10 years ago or 10 days ago, but is it still true now?


I prefer to think about identity as clothing rather than skin. You can put it on and take it off. You don’t have to commit to it.


You guys have tattoos?


A few.




[Laughter] OK. I never got tattoos because to me it’s like identity, clothes, skin.

Anytime I considered it for one second, I thought, “I might not want that someday.”


You were talking about the music story, and I do have a couple of guitars lying around the house. I want to buy a drum set, and I have tattooed it on my arm [laughter].


See, that’s a commitment. That’s cool.


But I haven’t touched a guitar in over a year, so. . .


I often come back to this place of, it’s better to get rid of something and if you miss it, get it back. It’s better to err on the side of no. Then if you do miss something, you get it back.

I was just thinking about it. Twenty years ago, I was in a relationship. We said, “Should we break up or should we not?” We both didn’t know, so we said, “How about this? Let’s break up and then if we miss each other, we’ll get back together.”

When in doubt err on the side of no. We did break up and after two months, we were like, “OK, we hate being broken up.”

We were talking on the phone every other day. She kept coming over. We said, “What are we doing?” When in doubt, go back to nothing and see how much you miss it.


It really tests your choice making ability because it reinforces that it is a choice to do something. You’re not doing it out of habit or by default because that can really breed resentment.

How do you approach making commitments? Some commitments are easier to break than others. For example, a commitment to having a child is much more of a long-term thing.


I just try to not make commitments whenever possible because I always feel like I’m going to let people down. I know my tendency to have no loyalty to things. I have no problem changing my mind and saying “no” to something I previously said “yes” to. I’m totally OK with that.

I really avoid it. Two years ago, I lost 40 pounds. I had been saying I wanted to for years, and then it just became my top priority. I said, “You know what? This is now my top priority.” As soon as I made it my top priority, all my actions fell in line with that.

I completely cut out all sugar, wheat, dairy, even caffeine, just for the hell of it. I started eating almost nothing. I waited until I was really, really hungry. If my tummy was actually grumbling, then I’d have a bowl of vegetables. Otherwise nothing. And I lost 40 pounds in a few months.

When friends asked, “How’d you do it?”

I said, “It just became a priority.” Of course, it wasn’t fun, but I thought, “This is now a commitment. It won’t be a forever commitment. Just a few months.”

It could have gone on longer, but after like after a few months, I thought, “OK that’s good enough. I’m happy now,” and then something else became a higher priority than that. Does that help?


Yeah. Were you able to maintain that weight after you lost it?




Hmm. How?


You’re asking the wrong guy [laughter]. I’m not a micromanager about that kind of stuff.


So you make commitments when the time feels right for you. It’s not a forever commitment. Do you communicate that to other people? Because sometimes the expectations that people have around these things are different.


I avoid public announcement. That’s the whole accountability thing.

Some people really get off on that. They say, “I’m going to publicly declare something and then I’m going to feel guilty and I’m going to hold myself to it because of social guilt.”

But that just doesn’t work on me. I have no problem breaking it.

A month and two days ago, I said, “I’m going to start publishing something on my blog every single day. I’m not going to announce that. I’m just going to start doing it.”

I started doing it, and after three and a half weeks, some people started asking me, “What the hell’s going on?” Before that, I put something on my blog every few months and I would email every time I did.

Suddenly, I was posting every single day without emailing people. Some people started to ask, “Did you kick me off the email list? What’s going on?” So, I sent out something on my list saying, “I’m doing this experiment where I’m writing and posting something on my blog every single day. If this continues, I might start a list about it.”

Sure enough, a few days after announcing that, I went off to Paris with my kid for a few days and decided not to bring my phone or computer and went with no tech. I was off line for a few days and there were no posts. I shouldn’t have publicly said anything, but the fact that I did didn’t suddenly make me feel that I had a boss or an obligation.

Feeling free is really important to me. I tend to have this rebellion even against myself. I’ve always slept on this side of the bed and then I caught myself, and thought, “Let’s switch. I’m going to take the other side.”

I constantly catch myself. If something starts to feel too much like a habit or addiction, I’ll intentionally change it up.


You’re working on another book right now that’s called How to Live?

Your approach to life is in some ways unconventional and probably rubs a lot of people wrong because it’s the opposite of how many people operate.

So, a book that is titled How to Live is particularly interesting. Can you dig into what that’s going to be about?


It’s not what you expect. It’s so exciting.

If you made me pick my favorite single book of all time, it would probably be the book, Sum, by David Eagleman.

It is a tiny, creative, fascinating book. The book’s subtitle is 40 Tales of the Afterlives, and the format is fascinating. Every chapter is answering the question, what happens when you die? But it’s answering that question in radically different ways.

Each chapter is standalone and each chapter deliberately conflicts.

For example, chapter three:

When you die, you’re surrounded by a bunch of thuggish little creatures looking at you saying, “What is answer? What is answer?”

You find out after a while that what you knew of as your life was actually an artificial intelligence program. You are an artificial intelligence program that they wrote to go figure out the meaning of life. Now that the program has stopped running, they’re trying to get the answers out of you. So, you try to tell them what you learned about life.

But every time you tell them, they look at each other with furrowed brows and say, “What is answer?”

You realize that if we were to write an artificial intelligence program smarter than us, we would be too dumb to understand its answers.

That’s it. That’s one of the chapters. Then the next chapter will say:

When you die, you’re greeted by a handler who tells you in your last life you chose to be a man. But once again, you can always choose whatever creature you want to be.

Every time it’s your turn to live again, you get to be whatever creature you want. You remember a wonderful day you had as a man when you watched a horse grazing in a field. You admired its simple life, just eating grass in a field. You say, “You know what? I’d like to be a horse.”

No sooner said than done, you start to feel your arms change into legs and your hands turns into hoofs. Your neck lengthens and your muscles change.

But then, you start to feel your brain turning into a horse’s brain and you realize that you’re starting to forget what a man. You realize, “Oh, no. What I loved was being a complex man, appreciating the comparatively simple life of a horse. But if I don’t even know what a man is anymore, I won’t appreciate my simple life. I’ve made a horrible mistake!”

You say, “Wait!” But all that comes out is [horse sounds]. At the last minute, before you completely turn into a horse, you have a horrifying thought, which is, “I wonder what kind of beautiful, complex creature I must have been before I chose the simple life of a man?”

Chapter 7:

When you die, you find out that, yes, God was in fact the creator, but he’s not a manager.

He created us billions of years ago. He knocked over the first domino and he’s off doing other things. He doesn’t even know we exist anymore.

I just love, love, love this format of 40 different answers to one question.

So, two years ago, I was walking down the road and I suddenly stopped in my tracks.

I thought, “Oh, my God. I want to write a book called How to Live with twenty-five different answers to that one question.”

Each chapter deliberately conflicts the others. Each chapter completely convinced it has the right answer, persuasively telling you that, “No, this is the way to live.”

Then the very next chapter will completely go against it because that’s honestly how my mind works most of time.

One chapter will be:

Here’s how to live: You must be fully independent. All misery comes from regrettable commitments to things. You must at all times be completely free and independent. You must be free of all technology choices. Be free of all commitments and relationships.

It’ll be a chapter that’s telling you how to be completely independent and you’ll follow that to the logical conclusion.

Then the very next chapter will say:

Here’s how to live: Commit. You need to pick a place. Pick a person. All the deeper joy in life comes from commitment.

I couldn’t come up with 40 to match the book. Some might say my book is definitely an homage to the book, Sum. But I came up with 25 different ways to live. It’s a blast to write because I actually believe in each one of these twenty-five ideas that are deliberately conflicting.


That’s so cool.


How many of them have you tried?


Oh God. I don’t know. I’ll think about that [laughter]. It feels like most of them.

I told you that I whimsically got married because I thought, “Commitment: That’s what life is all about. You just pick, and you commit. It’s the joy of missing out. You get pride in all the choices you’re not making.”

I did that for a few years until I didn’t [laughter].

I’ve gone all the way to the independent side. I’ve thought that learning and growing are the most important things in life, and if that’s true, then it logically follows that I should live as such.

The book is written in a very succinct format that I call directives. We can talk all around a subject, we can talk for many paragraphs around it, or you can just say in two sentences, do this.

It’s like the entire tree is contained in the seed. Sometimes, I think the directive is just telling somebody without precursors or apologies. “Do this” is the seed that carries all the other philosophies with it. The action is what really matters, rather than all the talk around it.

So, it’s written in a laughably direct format, “Do this. Live like this. Marry this kind of person. Live in this place.” Because it’s more succinct and amusing instead of babbling on about things.


Given the context that a lot of the directives are completely contradictory, it might produce this meta-insight in people.

Yes, they’re all these different options, but if you’re not doing it, it doesn’t really matter.


At first, I thought that I was going to need a really damn good conclusion to wrap it all up, but then I thought that that’s the difference between art and instruction. When you think of something as art, then everybody’s free to make their own conclusion.

If you think of yourself as a professor, then you’re trying to tell people what to think. I decided that this is really more of an art project. I’m no professor, so there is no conclusion.


Never conclude. That’s the final conclusion [laughter].


This loops back to that idea of leaving space. If you leave space, then something else can emerge. If you have a very specific conclusion, then that doesn’t leave space. But if you leave it open, then all kinds of insights can emerge for people. That might be totally different for different people.


It’s fun. I love the thought of somebody saying, “What did he mean by that?”

That’s more interesting than me telling them exactly what I meant by that.


Do you think about what kind of legacy your work is going to leave in the world?


I don’t have any spiritual beliefs. I think that our personality lives on after we die in the things that we create.

If there’s any argument of something that we could concretely, objectively call an afterlife, it would be the way that you share your personality all your life. I can still go read things written by people that are dead and totally get their personality, their way of thinking, and their framework.

To me, they might as well still be alive. That’s what’s weird when people get all upset that Ray Charles died or something. How many of his albums have you bought in the last 20 years? None.

His new music? None. The man you didn’t know died, but it doesn’t matter because the things he created are very alive.

So, I don’t worry about my legacy like that, but the thought that I just described kicks my ass a bit. Eustress, right? That pushes me towards sharing more of my thoughts and ideas.

I use my site for that, and to me, my site is the legacy. Anytime I’m doing anything on my site, I imagine that this will be around for 100 years after I die.

That’s another reason why it’s not on WordPress. The less code, the better, because in the future, somebody is going to have to maintain it. I use barebones HTML because who knows what holographic devices this will be seen on in the future. They might not have JavaScript anyway.


That’s interesting.


I think long term to a fault. Like I said earlier about tattoos. Even at the age of 14, I was like, “I might not want tattoos when I’m 80.” People just looked at me weird like, “Dude, why are you thinking about being 80?” And I’d say, “Well, it’s coming!”


It’s strange to me that you say you’re non-spiritual and yet, you have so many spiritual practices that you engage with.


I haven’t looked up what the word spiritual means, but it seems to it seems to be about a spirit. Spirit being a synonym for ghost. A belief in some entity, spirit thing. I don’t have that, so I don’t know what you would call it.


I think it really comes out of that. You’ve given yourself time to contemplate things that others haven’t. You’ve really figured out how you want to live your life. In my mind, spirituality or religion is all about how to live.


I wanted to ask you about your approach for self-knowledge. How do you investigate yourself and your beliefs and identity? Do you have any specific practices? Do they change with time?


Lots and lots and lots of writing in my journal. I write everything in a text file. I type really fast and free. Some people enjoy longhand, but to me, almost every day, I open up a text file and I just dump out whatever’s on my mind.

Then, I like to skeptically challenge everything I just said as a fact, and so if I said think such and such is a bad idea, then I’ll go back and add a question mark to it.

Is it a bad idea? Why is it a bad idea? What if it’s not a bad idea? What would it look like?

I like to doubt everything I think I hold true. What if it were false? What is the opposite? What are the other possibilities here?

Then there’s always the idea of pushing past the first few possibilities. We often think in terms of two choices. But once we get to two choices, we say, “Now I have to decide between these two choices.” Never stop at two choices. You can always add more. There’s always the choice to do nothing. Go crazy. There are always more choices.

Then, you could start to look at a spectrum of choices. I put aside time and do this kind of stuff every day. It helps.

I don’t do a lot of stuff that normal people do. I don’t watch videos of any sort. I generally don’t watch things. Almost any moment I’m awake and I’m writing, or talking, or reading. And that’s it.

I don’t hang out. I don’t sit on couches [laughter]. That kind of stuff.

If it seems like I’m weird in the stuff that I do, it’s what I do during the time that normal people would spend watching things. I spend that time writing.


How have your ideas about minimalism and your philosophies for living changed since you’ve had your child?


See the Lego back there on the table?

Up until he was about two years old, I held my minimalist philosophy and applied to parenting. He had no toys. We would go outside and play with sticks or rocks. We were living in New Zealand, and I went to a cafe in Masterton that had a huge box of toys.

He saw this box of toys and he just sat there and played with everything for three hours. I didn’t interrupt him. I sat there for three hours, ordering a second and a third cup of tea and watched him play. I thought, “Oh my God, he’s in heaven.”

Then I realized, “OK. I made a mistake. He needs toys. This is clear.” So that night I went onto eBay and found somebody in Wellington, where I was living, that was giving away three or four huge boxes filled with toys for $10.

I presented him with four giant bins of toys, and for the next five years until we moved to Oxford, he played with that giant box of toys every single day. Never got tired of it. It was a good lesson.

In the beginning, you asked me about “hell yeah or no.” That’s a certain tool for a certain situation. Minimalism is a certain tool for a certain kind of desire for a certain kind of situation. It’s not the answer to everything.

Question all of these -isms. They’re tools. We don’t need to think that just because something is true for us now, that it is true for everything. It’s just a tool for now.

Most of what works for me in my life, I don’t apply to his life. I don’t try to push it on him because I know that it’s not what he needs.


You seem to be deeply committed to processes. For example, the process of changing processes and using processes to uncover what’s working and what’s not.

You seem to be very disloyal to states. You’re not trying to get something, be something, have a checkmark on a to do list. You’re not looking at states at all.


We talk about commonly known spectrums like introvert versus extrovert. But there are other ones, too. There is a spectrum of how much we tend to find similarities versus find differences.

There’s a name for it in psychology and they can measure it. They can ask you some questions and say, “Oh, you’re a similarity finder or you’re a difference finder.”

I read that one of these spectrums is being process-focused versus goal-focused. The cliché of the person who is process-focused is she does something almost to completion and then goes, “That’s enough. I was doing it for the doing, not for the end result.”

Years ago, when I took one of those tests, I remember realizing that is totally me. I will very often do something almost to completion. Then I’ll feel like, “Yeah, I got it.”

If I’m doing it for the doing, I don’t really care whether I get to the finish line or not.

That would be a fun little skit about like the process-focused person running a marathon [laughter]. A few feet before the finish line, I’d say, “I’m done. Let’s go. I don’t need to cross it. I was just doing it for the running.”


Especially if they were in first place. That’d be really hilarious.


That’s got to be the 26th and 27th lesson in your book. Never complete anything [laughter] – never conclude and always conclude.


One of them is about reinvention and beginner’s mind. When you’re new to something, that’s when you make the best progress and get new insights. Living in the name of reinvention, you stay a beginner at everything. As soon as you’re enough of an expert, it’s time to reinvent and pick something completely different to do it again.

When I was living in Singapore, I lived in this building that was right above Marina Bay, which is like Central Park. That’s where they would do all of the marathons, races, and triathlons. They would always begin right below my window. Very often at 6:00 a.m. on a Sunday, I’d be woken up with loud speaker sounds.

I’d look out the window at all of these people, organizers with clipboards and everybody with the numbers on, and I’d just think, “You could have run the same 10 miles yesterday by yourself. Why would you choose all of this noise and screaming and commotion and the numbers and the clipboards and the walkie talkies? Why not just do the run yesterday?”

I said this to somebody who looked at me and said, “You know, some people like being around other people.” [Laughter]

I said, “Alright. That’s my introvert thing. Everything’s better alone.”


And some people like structure and organization.


That’s the goal-focused versus process-focused. If you’re goal-focused, it’s really important that you did the marathon. I was number thirty-seven and I came in 19th place. People want to show that they achieved that goal.

There was a guy who beat the world record and ran the marathon in under two hours just last week. But they say that it doesn’t officially count because he had pacers running with him.

Because it wasn’t an official marathon that had other contestants, it doesn’t count for some reason. He knew that. He said, “I’m doing it anyway just to show that in ideal situations, a marathon can be run in under two hours. We proved it now. And so, I hope others will too.”

Once Roger Bannister broke the four-minute mile, ten other people did it the following year, even though it had never been done up until then. So, the marathon guy did it for that same reason. You can say it wasn’t official. It doesn’t matter to him.


There are so many different ways that living beings can thrive. Humans are fascinating in the sense that we are so versatile. There are so many different modes of being that can make people happy and fulfilled.

Even in How to Live, you’re presenting so many different pathways that people can take. It’s really interesting for people to ponder over, especially if they’re feeling stuck because there are a million different paths and the one that you’re on right now may not be optimal for you.


Or you might have been there, done that already. That’s what’s really helpful about the 4-Hour Work Week. Tim Ferriss writes about different ways to approach life. whether it’s the many “mini retirements” or even the tiny stories about the family that sold their house and traveled the world on a sailboat for an entire year.

The total cost to live on a boat for a whole year and travel and sail the world was $18,000. Hearing that something like that is a possibility makes you go, “Wow. Is that what I want? I could do that.”

Even just knowing that you could do something like that makes you question, “Do I want to or not? I kind of want to. Do I want to badly enough to give up this house? Maybe not. Therefore, I actually value comfort more than sailing.”

These stories make you question your values. It’s always wonderful to be presented with other options.

That’s what explorers do for us, right? 200 years ago, there were places on the map that we didn’t know what was there yet.

Explorers were physical explorers. They’d go off into the darkest parts of Peru and explore places that hadn’t been discovered yet.

Then they’d come back and draw maps and report to us about what’s there. But now that we know what’s there physically in the world, I think we still need those people who are life explorers. They go explore what can be done with a life and show it to us and show us places on the map of possibilities that we didn’t know were there.


Wow. That’s a place to wrap up.

From the sense making, the sovereignty, the shadow work, stoicism – it’s really cool to see someone in a different place in life coming to a lot of the same conclusions from their own reflections.


I had done almost no interviews for the last almost four years now, but when you guys asked, I thought, “Yeah, alright. You guys are cool. We’re going to have a good conversation.”

And I loved this conversation. So, thank you.


Cool. Thank you, too.


It was awesome to finally get that “yes.” I don’t know how to put it into words, but you’re weird [laughter] and it’s cool.


The ultimate compliment.


You do things in ways that are very counter to the way other people do things. You seem to have so much joy about it. You’re stoked about it. The tone of this interview was really different than a lot of other interviews, and I like that. So, thank you for your time.


Anybody who listened to all the way to the end, go to my site at send me an e-mail and say “Hello.” I still reply to every email and I enjoy it. I like hearing from strangers around the world. It’s fun.