Derek Sivers

Interviews → Far Out / Julie-Roxane Krikorian and Alasdair Plambeck

Local vs. global, why we travel, singing the counter melody, freedom, expired identities.

Date: 2020-05

Download: mp3



This is Far Out. A podcast about stepping off the beaten path and learning to live from our center.

Welcome. Today is a very special day and we have a very special guest. We are talking to Derek Sivers today.

Derek has been a musician, a producer, a circus performer and entrepreneur, Ted Speaker and a book publisher. He started CD Baby and Host Baby a long time ago and sold it to the tune of 22 million dollars.

He has a short audio book that will tell you everything about it. It’s called Anything You Want. It talks about all the things he learned while starting, growing, and selling the business. I highly recommend it. It’s a nice, short book, but it has a lot of great insights.

He’s a self-described monomaniac introvert, slow thinker, and he loves finding a different point of view. She writes at and he’s a California native who now lives in Oxford, England.

And without further ado, Derek, welcome to the podcast.


Thank you for having me.


This is quite a moment for me because I’ve been following you for almost a decade. I remember picking up your book, Anything You Want, back when I was first working in startups. I’ve been fascinated by your journey and by the way you think ever since I read your book.


I just reread all of our emails since 2012 this morning.


When I recently emailed you, you said “I remember you.” I thought, “Whoa, does Derek really remember me?”


I have my systems [laughter].


For those listening that might not know you, could you share a little bit about who you are and a little bit about your journey?


I was born in California. I started travelling the world when I was one year old. I decided at 14 I wanted to be a rock star and I was monomaniacally focused on that one single goal, total workaholic, and really serious about doing that. I went to Berklee School of Music, moved to New York City when I was 20.

Again, still focused on being a successful musician. I had a job for two years and quit my last full-time job in 1992 at the age of 22. I was also in a circus for 10 years as the ringleader emcee from the age of 18 to 28.

I stopped only when I got caught up in this little hobby that I started called CD Baby, which took off and became the largest seller of independent music on the web.

Then I did that, monomaniacally for 10 years from the age 28 to 38 and when I was 38, I felt done. After doing that for 10 years, it was too much responsibility. I had 85 employees and I didn’t like it anymore. So, I stepped away, sold the company and have been nomadically travelling, thinking, writing, and speaking since then.


I’ve heard you describe yourself as just a writer these days. Is that mainly how you think about yourself nowadays?


Yeah. I realized that I used to have a list of things, “I am this and I am that.”

I said I was an entrepreneur but that was 15 years ago. I’m not really doing that anymore. I said I was a programmer, but that’s really my hobby, it’s not my profession. I said I was a musician, and it’s a language I still speak, but I don’t think it’s an active verb for me anymore.

Being a writer is the one thing that I’m the most serious about nowadays.


With CD Baby, you said you felt like you were going to run that company for forever.

How do you navigate saying no to something that you have said yes to for so long?


Good question. There are two kinds of saying “no.” There’s saying “no” to yourself and saying no to someone else. Let’s talk about the obvious, saying “no” to someone else because that’s the harder one.

You need to know that it’s a tradeoff. Everything will suffer if you try to do too much. So I say, “Hey, I’m sorry. I wish I could, but I can’t. I really need to focus on this one thing until I finish it.”

But if somebody is asking me to do something I say, “Please ask again someday if this offer still stands. It’s nothing personal. It sounds wonderful. I really, honestly wish I could do it, but I know that we all have limitations on time. I really need to focus on this one thing.”

It’s amazing that people almost always say, “Oh, man, that’s so cool that you’re staying focused. No worries. I totally understand. Man, I wish I would say no to more things in my life. I really admire that.”

I actually get rewarded doubly for saying “no.” I get the free time and I get the praise from the person that I said “no” to because they think it’s really cool that I’m staying focused on something else.


On top of that, you’re modeling for other people that they can say “no,” too. You help others’ find their own boundaries and align their focus.


It’s tough when you have to make the identity decision. At a certain point, I had to admit that I was no longer a musician. That’s why it’s always a tradeoff.

You have to understand that you can do anything in the world, but you can’t do everything in the world. You need to decide. And the Latin root of the word decide comes from the word to cut off. So, to decide is to cut off options.

I have to trust that if I really want this part of my identity bad enough, even if I’m cutting it off right now, if I’m saying, “I am no longer an entrepreneur,” I have to just know that if it’s something that I want badly enough, it’ll come back. Nothing will stop it.


It’s funny how you can get out of an identity and think, “Yes! I feel free!” It’s useful to have an identity. It’s nice.


It’s a human being thing [laughter].


But how do you decide?

I’ve definitely struggled with old identities popping back up. There’s still this nostalgia and longing for it. How do you deal with that? Do our identities really die that easily?


You have to admit when your mission has changed. It helps to look at your actions, not your words. If I’ve been saying I want something for a long time but not doing anything about it, I used to think that meant that I really wanted it.

I realized recently that the opposite is true. If I’ve been saying that I want something for a long time, it actually means I don’t really want it, because otherwise I would have done it already and vice versa.

If I’ve been repeatedly drawn to something, if my past actions keep doing something, then that must be something I want. Sorry, this isn’t really an identity thing, but it’s a recent example from my life about my identity. For years, I’ve been saying that I want to live in a dense, multicultural, international city but my actions always choose silence, solitude, and nature.

Even on a small, day-to-day level, I’ve been getting up early to go on like a 9:00 A.M. walk through a huge park here in Oxford. But there were too many people out at 9:00 A.M., so I started going on the walk at 7:00 A.M. I would still see pretty many people, but it was better.

Then, I started walking at like 5:30 A.M. Now, I only see a few people. This morning, by accident, I woke up at 3:40 A.M. I thought, “Huh? I’m wide awake. I’m going to go on that walk right now.” I was out the door by 4:00 A.M. and I went on a two-hour walk.

It was the best walk ever. I was the only human being awake. It was amazing.

The park was filled with all these little bunnies. Because I was like the first person to walk through, I saw around 300 rabbits and I got to see the sky turn from dark blue to orange to pink and I thought, “Oh man. This is my favorite thing.”

So, I say that I want the intellectual stimulation of living in a dense, multicultural city. But come on, look at my actions at every step, no matter what I say. I keep choosing more and more and more solitude and silence and nature.

And secondly, you need to acknowledge when you’re making these transitions. If a certain identity of yours has expired, you need to acknowledge that it’s not that one identity is true and the other one is false. Instead, you need to acknowledge that you actually do want both things. You need to figure out how to balance them and acknowledge both, as if both are actually little selves inside yourself.

Don’t completely banish one’s self down to the basement. You acknowledge both of these selves inside of you and find a balance. If you want to be a musician but you also want a steady income, instead of feeling like you need to decide between the two, acknowledge both.

Go get a good paying job that doesn’t suck your soul from 9-5. At 5, you’re out the door and you don’t let it exhaust you. Then, every night you come home and do at least two hours of uninterrupted music making just for fun. Just for love. Don’t try to make money from your love and don’t try to love what you do for money.


I really love that. I find myself thinking a lot about how I rank values and prioritize what’s most important and what’s not.


Two thoughts. Again, we’re recording this in May 2020. No matter when you’re listening, it’s a time in the world where everything has been flipped upside down.

You have to acknowledge when your values have changed. You might have said for the past six years, “Adventure and travel is the most important thing to me.”

And then suddenly this happens, and you go, “Huh? Actually, six months ago, adventure and travel were super important. But right now? I’d like a little safety and stability.”

It’s important to acknowledge when your values have changed and not think that you need to stay true to who you were before.

When I’m trying to decide what interests me, I like to reverse it and ask myself, “What do I hate not doing?”

That’s a thrill. It’s a much more fun question. If you banished everything from your life, what would you hate? What would you miss the most?

That’s a better indicator, but more than anything, like I said before, look at your actions. Look at your past self. Look at what you keep choosing again and again.

When I started CD Baby, I was a full-time musician. I was completely devoted to being a successful musician. Laser-focused.

But I was also spending almost 12 hours a day working on this new website that I made because it was so damn interesting. I worked into the night, sometimes until 2 A.M. because I was so fascinated. I was learning and growing and building every day.

I started to notice that I was actually disappointed when someone offered me a music gig because that meant I had to stop working on this website for a day. I thought, “Aw man, I just want to keep working on my site. I don’t want to go do another gig. Oh wow. . .I never thought I’d say that.”

I looked at my actions and then finally acknowledged that something in me must have changed. Now, I love this more than making music. So, again and again, my advice is to ignore your words and look at your actions and notice what fascinates you.


I really resonate with that because I teach a Mindful Money program. I have people come up with their expenses for last two months and we will analyze what they spent money on with the idea that your past actions are a good indication of what your actual values are.

Part of the practice is to simply be aware of it, because that’s how you can make different choices in the future

Do you have any practices for becoming aware of these values?


You have to remember, I’m old.

I like what you said about teaching students to pay attention to their actions. I didn’t learn that until I was 48. I’m 50 now. That’s a brand-new thing to me.

I’ve been paying attention to my words my whole life. And only at the age of 48 did I say. “Huh. That’s pretty inaccurate.”

I journal a lot. I spend one to three hours a day writing privately. If I’m going through a massive decision in life, like what country to live in, I may spend five hours a day in my journal. I like to ask myself questions.

And then most importantly, I like to question my answers. I like to doubt myself. I assume that I’m accidentally lying to myself. I assume that the person speaking is a liar, meaning me. I like to dissect my beliefs and habits and actions and see if they might be hollow. So, if I seem self-aware, it’s because I spend probably more time journaling than almost any other action in my life.


Was there ever any disappointment in yourself because you had these dreams of where you were going to be as a full-time musician, and all of a sudden you changed? Or was it really just a process of observing what you were doing and coming to rational conclusions?


I get what you’re saying, and I would have felt that, except the new thing I was working on was just so damn exciting. Nothing was pushing me away from music, I was just being pulled towards this new thing because I was so into it.

The world was rewarding me, too. I did pretty well as a musician – I wasn’t a super Rockstar – but I bought a house with the money I made touring. Technically, I’d say I was a success and I was proud of myself, but it was always hard. I always felt that it was a struggle. I was always having to pick the locks on the doors of opportunity. They never opened for me.

As soon as I started CD Baby, all the doors flung wide open.

Everything went my way. Everybody welcomed me. Everybody loved this thing that I made and gave me the red-carpet treatment. The world was rewarding me more than ever before in my whole life.

I’d also been a full-time musician for fifteen years at that point, so I was feeling like, “OK, that that was good. I had fun. I learned a lot. I did it. I can tick that box and say that’s done.”


Was there a particular transition that was very hard for you?


I recently gave away my musical instruments. I was torn on that one for a long time. Every day, I would look at all of my instruments and my soul would be a little torn thinking that I should spend some more time making music. I would always go to bed a little disappointed that I didn’t make music that day.

Those feelings lasted a few years until just a few months ago, I give away all my instruments to a full-time musician who’s friend of mine here in Oxford.

I felt good about it afterwards, but it took a long time for me to get to that point and really admit to myself, “No, I’m not making music anymore. That’s so weird to say. But it’s true.”


You have a really beautiful blog post on singing the countermelody. Can you share a little bit about this idea?


I feel that there is a common narrative and a general accepted truth. I call that the melody. And the reason that my blog posts sometimes seem a little strange is because I feel that there’s no reason to sing unison with that melody that’s already out there.

Instead, I look for something to be the counterpoint to it. I’m not looking for something to harmonize with it.

In true harmony, if somebody is singing a C and somebody singing an E, they go up and down in the same direction. That’s singing harmony. But a countermelody is where you have two melodies that can intersect. They’re truly two different melodies, but they can go simultaneously and make a more interesting piece of music.

I think of what I write as not the definitive end all, be all, definitive truth.

Instead, I think of it as a countermelody that’s aware of the melody that it’s singing against.

I’m like this because ever since I was born, I moved around a lot. Wherever I lived, I felt that I’m not from here. And therefore, the norms didn’t apply to me. Their expectations didn’t work on me.

Then at 14, like I said, I decided I wanted to be a musician. During my entire high school experience, all the teachers talked about how to get into a good college so you can get a good job, but none of that applied to me.

And then from the age of 18 to 29, I was a professional musician and in a touring circus. The things that people do to try to be respectable adults didn’t apply to me. For example, wearing a tie and a watch, getting a salary, getting insurance, paying a mortgage, and trying to build stability. That never applied – I was surrounded by circus performers and musicians – none of us had any stability and none of us wanted it.

I quit my last job in 1992 when I was 22 years old, and I haven’t had a job since.

This has been my reality for so long that I don’t even think about trying to fit in anymore. In fact, I was born in Berkeley, California, we left when I was two and then I lived in California after that until I was 38. And I was about to sell CD Baby and I was seeing a girl that lived in San Francisco.

She said, “I can’t really come to you. Can you come to me?” I said, “Sure.”

So, I lived in San Francisco for the first time and thought, “Ahh, the mecca. I can’t wait till I get to know this place.”

My whole life, I thought San Francisco was my destiny and they had this booming whole tech world. And I fucking hated it. [Laughter] I hated it because everybody was like me.

I thought, “I fit in? Ew. I don’t like this at all!”

I lasted a couple months and I had to get out because I fit in. I was terrified.

Singing a countermelody is because I don’t do anything by the norm. I don’t pay attention to the norms. I assume they don’t apply. It’s especially weird in tech. In programming, I like coding everything myself with no frameworks. I use the OpenBSD operating system instead of Mac or Windows. I like doing functions directly in my database instead of JavaScript and I like managing my own server instead of using the cloud.

People can understand me not wanting a job, but not using the cloud? “Oh dude. Now you’ve gone too far, man. You’re not thinking straight if you’re not using the cloud. We’re all using the cloud.”

It’s funny how there can be this group think in these really specific pockets like programmers. I don’t use Google, Facebook, Spotify, Instagram, WordPress, or Netflix, and I don’t think I’m missing anything. I feel like the whole world is playing this game of cricket where I don’t even know what the rules are, and they don’t apply to me.


I have a suspicion that there’s one thing you might have left out. I know that you are an INTJ with the Myers Briggs personality test. I’m also an INTJ.

This singing a countermelody and not quite fitting in or wanting to seem to be in our DNA. Has being introverted has played a large role in your life? Was that something you had to discover? Or was it something that you were always fairly comfortable with?


That’s a really good question. I honestly never thought about that. You’re right. When I think of my extrovert friends, they really like being in a group. Some of my dear friends hate being alone. A really close friend said to me, “If I had it my way, I would never be alone for a single minute for the rest of my life.”

That’s a nightmare. That’s worse than jail. Jail doesn’t sound so bad [laughter].

But if you always want to be in a group because that’s your value system, then by definition, you want to fit in with the group. I almost always would rather be alone. That’s a great metaphor. I don’t want to be in any groups physically or belief wise.


It strikes me that the counterpoint is also the dialectic method to some degree. Tension between two opposites in life is often a catalyst for a new point that drives growth.

When you have two tensions, you have to navigate them and find a novel solution.


I like that. I’m an experimenter. If everybody’s doing something one way, we don’t need to experiment with that anymore. How else could it be done? It’s all a big, fun experiment. It’s good to ask, “What’s another way to think of this? What’s another way to do that?”


I really like that.

In your writing, what is the bigger value behind it for you? Do you share it because it’s just fun? Or is there a bigger purpose behind it?


That’s a great question. You’re making me realize there’s a difference between my life and my writing. Even talking about the countermelody, I didn’t say that my life is a countermelody. I said that my writing is a countermelody.

I’m not trying to live my life in some deliberately veering away path, but I do deliberately do that with my writing because I feel that it’s my job. Why put out words that have already been said? Why put out an opinion that’s already out there? We don’t need somebody to say that again.

Instead, I only try to put out writing that says something I haven’t heard anybody else say. I often stop and reflect on principles. I ask myself, “What do I really want? What’s the real point of this?” Ignore the world, ignore the norms, and be honest with yourself. Ask yourself what you really want.

When you answer that sincerely and it feels true, then ask yourself, “What’s the most rational, efficient, direct way to get that outcome? Do I need to go through this little ceremony that other people are doing, or can I go directly to it?”

My actual life decisions and how I live my life revolve more around that. I ignore the norms and I go for what I really want. Sometimes it turns out to be exactly what other people are doing, too. I don’t deliberately not do what other people are doing.

We’re talking right now from a normal little two-bedroom house in an Oxford suburb. It’s not like I’m dangling from a tree house in a helicopter right now or living under water in some weird alternative life [laughter].

But as far society’s influence going against societal norms, I think of it this way: imagine you’re in a very foreign land.

You guys are in Guatemala. I’m in England. We’re both from California. I was going to try and pick a place that’s alien to both of us, but who knows what they would be. So, let’s say imagine a fictional place. You’re in a foreign land.

Let’s say that all the local people all touched their left elbow with their right hand to ward off evil spirits whenever they say any word that begins with the letter K. If you were staying in this land, even for years, you probably wouldn’t adopt this belief.

Even if you felt like imitating this action out of cultural respect, you wouldn’t suddenly subscribe to the entire concept of the evil spirit and a belief that touching your elbow would keep it away.

Even if they said, “Oh, no, no, no. You really should do that. Otherwise, the evil spirits will get you.”

You’d say something polite because you’re considerate and empathetic, but still, you wouldn’t feel actual pressure to conform because you know that that’s not congruent with your beliefs. You’d be completely unaffected by it, no matter what they say.

That’s how I feel when people tell me that I need to do some societal ritual that’s normal for them. The world is filled with these things that even some dear friends of mine are shocked that I’m not following. They think that certain things are clearly, objectively true and I must do them. I think, “No, that’s just your belief. I don’t subscribe to that.”

They try to rationalize it with some belief system that I don’t believe and so it has no effect on me.


Do you have any advice for someone that feels like going against the norms is a leap of faith? Maybe someone in their 20s and experience isn’t on their side.


Experiment. The best place to start is by saying “no” to things. Get more practice saying “no.” It’s the easiest first start. Somebody tells you that you need to write a business plan? Say “no.”

Or somebody says, “You really should track analytics on your website.”

“You should really find a mentor.”

“You need to celebrate New Year’s Eve with us.”

“You should really take more photos when you travel.”

“Where’s your social media presence?”

“You need to follow your passion.”

Say “No!”

Know that the world is going to always, always, always tell you that you should be doing things. It’s really healthy to say “no” to all of it by default. Maybe quietly later, consider things after you’ve said “no” by default.


I like that because for most of us, the default is “yes.”

Saying “no” saves you a lot of energy.


And when you’ve said “no” to family Christmases for six years and you end up coming on the seventh year, people are thrilled you’re there.



That’s weirdly specific. You’re speaking from experience [laughter].


It hasn’t been six years yet, but I’m bordering on it.


I’m curious, when is it right to say “yes” to everything, versus the hell yeah or no concept?


I’m so glad you asked that because hell yeah or no got surprisingly popular as an idea. Some company in Singapore made tea mugs out of it and somebody in Bangkok has a T-shirt that says it. It’s sweet and flattering, but it’s weird when I get emails from people who say, “Hey, man, I love your hell yeah or no idea. I’m applying it to everything in my life!”

I think, “Oh no! That’s not the point.”

It’s a specific tool. It’s one tool in the toolbox for a certain situation when you’re overwhelmed with opportunity. Early on in your career, you should definitely say “yes” to everything.

Go crazy, sleep less, drive yourself to the point of exhaustion, try everything, experiment a lot, come up with tons of ideas, try to execute as many as you can, meet as many different people as you can.

Say “yes” to every gig, hold down many jobs, or ideally don’t do any one single full-time job that will take all of your time so that you can actually hold down three or four different part-time jobs just to expand your networks and opportunities.

Then, when one thing takes off and is rewarding you, whether that’s rewarding you with praise, or money, or deep satisfaction, you can double down on that one thing and say “no” to everything else. You can put your head down and focus. That’s when hell yeah or no comes in.

That’s when you raise the bar all the way to the top and you start saying “no” to every invitation because you’ve already found your thing and it’s already rewarding you. Ideally, everybody wants that thing from you whether it’s a service or a product or whatever it may be.

But until then, the better strategy is to say “yes” to everything.

It seems like your life is very rooted in a deep sense of who you are and what you want.

Are there any tradeoffs for being the way you are?


Very little. Some people get frustrated with me. Some people are disappointed that I don’t value what they value. Metaphorically, I think of it like the family who says, “Why don’t you live next door? Wouldn’t that be sweet?”

But instead, that grown child goes off to travel the world. Yes, the family may be upset, but your travels are not only for your personal good, but also for the greater good to expand horizons. Even if the family is a little sad that you’ve chosen to travel the world instead of living next door, deep down, we all know it’s for the greater good.

Even when your friends or colleagues get a little frustrated with you for being weird, it is always for the greater good. It’s showing the world that there’s a different way to be. We don’t all need to step in line and conform. Something can be a totally valid and well thought through way of approaching this situation, even if it doesn’t match yours.


You have an amazing blog post about freedom.

You wrote, “What is personal growth anyways? What do you do when you don’t have to do anything? Where do you go when you don’t have to be anywhere? Is there such a thing as too much freedom?”

I’d love to hear your thoughts on this.


Sure. There’s a cute story about this. A friend once asked me, “If you could do anything, what would you do?”

I answered him and he said, “Good news. We CAN do anything.”

I thought, “Oh sweet! You’re right.”

But there’s a funny flipside of that. This question, “What would you do if you didn’t have to do anything?” No matter what you answer is, there’s good news. You don’t have to do anything. You can refuse any obligation – even the ones that seem like you can’t.

For example, you have to pay taxes. Well, no, actually you don’t. If you don’t feel like paying taxes for five years, you don’t have to. There will be consequences if you don’t. The IRS may flag your account and come back to you and say that you owe them tax plus interest.

But if you’re ever, ever, ever feeling like, “I have to do this, I have to do that.” Try to catch yourself and check back in. “Wait a minute. Hold on. I don’t have to do anything. No matter what.”

Is there such a thing as too much freedom? I have been asking myself that question for over 13 years now and I think I have an answer now.

There are times in your life when you need more options. And there are times in your life when you need less options.

Think of the stereotype of a brainstorming session, which sounds very corporate to me. Let’s have a brainstorming session. Picture a room of wacky people coming up with tons of ideas.

At some point in the brainstorming session, you have to stop opening up the floor for discussion and ideas. Instead, you have to narrow it down if you want to produce something or act upon something. You have to narrow down the options at some point and reduce. You can’t just leave it wide open forever, or you’ll never produce anything.

So, my answer to your question is that it depends on where you’re at in your life. If you’ve been too restricted and you feel like you need more freedom, then no, there’s no such thing as too much freedom for you.

But when you get to that point of feeling paralyzed and drowning in options, it’s time to reduce your options and narrow them down.


I’ll bring up another metaphor here since we lead wilderness retreats. At some point, you have to take the next step. And that is a limiting choice. You can only step in one direction before you stop. You could stop at 360 degrees. You could go in almost any direction, but you have to step in SOME direction.

Perhaps after you take 10 steps, the landscape opens up differently. New options show up that weren’t there 10 steps before.


I like that. I was thinking of the painting metaphor where every stroke of the paint brush on the canvas is reducing the options. There are infinite options on a blank canvas, but as soon as you put one stroke of paint on it, you’ve now greatly reduced your future options. Two strokes? You’ve reduced your options even further.


When I work with people financially, many of them say, “I want freedom.”

My question to them is always, “ Freedom for what?”

I always get a mental picture of an astronaut floating through space.


He has total freedom, but he can’t do anything. In my own experience, when I experienced the most freedom, I felt detached from everything else. This leads me to question, can you be in relationship to the world with total freedom?


Personifying the world like that is sweet and poetic. But I think that you can’t be committed to “the world.” You have to make sure you know what you’re really committed to. Are you committed to a specific place, person or outcome, even if you think you’re committed to freedom?

The whole time you were talking about the astronaut, I’m thinking, “You need to dig deeper and decide what you really mean by that.” And by you, I mean, whoever you’re speaking to that says they want more freedom.

It’s probably a good time to ask more questions and get specific. Freedom is a word that needs a target.

Because one person’s definition of freedom might be that they want freedom from their parents. Another person might say, “I want freedom to live where I want to live and do my work.”

I say, “Ok. You want to be nomadic. That’s different than the vague idea of freedom.”

Some people want freedom, but they have a dog and have to care for it.

For other people, having a dog and going out on long walks is freedom.

Get more specific – even with yourself. If you’re listening to this interview and feel like you want more freedom, go to your diary and ask yourself, “Freedom from what? What does that really mean in concrete, actionable terms?”


Imagine a life where you have endless options and it’s overwhelming. I remember having enough money and enough time in front of me that I could go live anywhere in the world and it was paralyzing. I ended up not travelling to many places because of it.

In a bigger sense, I’m also coming to this conclusion that you need the contrast. That’s what makes it exciting. That’s what makes for a full life. In one of your podcast episodes, you shared a story about going from an ice bath to a hot sauna. You talked about the contrast between very, very hot and very, very cold and how you found relaxation in the in between.


Nice. You have to feel the pain to know what it’s about. Same with minimalism. You can’t just preach at people saying, “You should be more of a minimalist.”

People would just think, “OK. There’s another person telling me what I should do.”

It’s not until you felt the pain of having too much stuff and you’ve tried to take care of your suffering. You had to move three different times and put all of your stuff into a truck and take all your stuff back out.

When you feel the pain of having too much stuff, then you’re ready to wholeheartedly pare down because you’ve felt the pain personally, not because some blogger tells you to.

It’s the same with freedom. If you’re feeling like you don’t have enough freedom, go all the way, say “no” to all obligations, get completely free, go be the astronaut drifting in space with no cord, and then feel that pain of indecision and too many choices.

Then you’ll say, “Now I felt the pain. I get it. I see why I need to commit to some things.”

It feels like a very Derek move to say, “You say you want more freedom, but perhaps you just want to be less overcommitted? Flip the question around. What’s getting in the way of that freedom?”


There was a time, four years into the start of my company, CD Baby, where I was about to move to Hawaii and work remotely because I was sick of everybody.

I felt that all of my employees were dumping all of their problems on me and I needed to be far away from all of them. I was about to book the flight. I contacted a landlord in Hawaii, and we made an agreement to rent her apartment.

I was going to send the money the next day, and then I slept on it. That night before I fell asleep, I decided to get more specific in my journal. I thought, “I’m sick of everybody? Hm. It’s really just Nicky. Nicky is really a complete pain in the ass. Everybody else is wonderful.”

I realized that I really needed to deal with Nicky, and I cancelled all Hawaii plans. I went in the next day and said, “Nicky, I’m sorry, this isn’t working out. You got to go. I almost moved to Hawaii to escape you. I’m sorry. This isn’t a good fit.”

She was in customer service at the time and it wasn’t a good fit. It really helps to get more specific and make yourself answer very, very specifically, “What is it that’s bothering me? Exactly what do I want freedom from?”


You wrote a great blog post called Local versus Global. It’s found at

Can you talk about why you wrote that blog post?


Sure. The idea in a nutshell is that you can focus your time locally or globally. If you’re local, that means that you’re focusing on your community, doing things in person, but that means that you have less time to focus on the rest of the world.

If you’re global, that means that you’re constantly making things for the whole world. But this means you have less time to be part of your local community.

Neither approach is right or wrong, but you need to be aware of the tradeoffs.


We have a very global focus right now. We’ve been living in Guatemala for six months. We know very few people in town, and we don’t have any friends. We’re introverts, so that doesn’t help.

We don’t we go out. We just work on our laptops and a lot of our social interactions are online. By the end of the day, we’re tapped. Then, the weekend arrives, and I just want to relax, so we don’t end up going out.

Obviously, right now, this situation is preventing us from going out further. But we already weren’t doing that.

I do find a lot of value in focusing my attention on the local, but as I’m developing more global things and as I’m trying to build businesses that can be done from anywhere, I find that I don’t have the mental energy or the time to invest it locally. And we don’t stay long enough in places to invest a local environment.

Do you feel like you’re more local or global these days? Have you found a balance?


I think it’s a natural preference, kind of like introvert versus extrovert. But I think we all have a natural inclination to go for one or the other. For listeners, if you’re not sure where you stand, I have some questions that I would ask yourself.

Are you an active part of your local community where you live? Do you actually know lots of people where you live and get together all the time?

Here’s an important question, does an in-person conversation feel more real than an over the phone conversation? If so, then you’re probably more local focused, even if you might be nomadic right now.

In general, if you believe in person is the real deal versus phone, you’re probably local focused in your heart and vice versa.

Like I said, look at your past actions. Even if you said, “I want to move to Berlin and be part of the local community. Wouldn’t that be great?”

In theory, that’s great, but look at your actions. Next, you have to acknowledge your preference and go with it, even if it’s unusual. As always, people will always tell you you’re wrong over and over and over again.

Whatever way you’re doing it, somebody is going to say that you’re wrong. When I posted that article in 2012, I was 42 years old. Only then, I finally realized and admitted that I’m not local. I prefer phone conversations to in-person conversations.

That infuriates one of my best friends. We’ve been best friends for ten plus years. We talk on the phone every day and she always talks about getting on a plane to come see me. I’m like, “No, don’t do that. Save the airfare.”

I prefer talking with friends on the other side of the world over talking to people where I live.

I’m more globally oriented, but I’ll admit that the whole COVID thing had me re-evaluating this. I am one of the lucky few on Earth to be a New Zealand citizen. New Zealand is closed to all but citizens right now.

It’s really tempting to move back to New Zealand and decide that for the next many years, travel is not as appealing as it was a year ago.

This whole idea of being global and constantly fluttering around from one place to another? I think I’m going to try the opposite for a while. New Zealand is a place that in my heart I could actually commit to. And for the first time ever in my life, maybe I’ll be a part of a local community. That’s really exciting to me now. We’ll see. Ask me again in a year. We’ll see what happens [laughter].


Travel is such a huge part of our lives. This virus has left us really conflicted. Travel seems like a really integral part of who you are, too.


I have so much to say about this. I’ve been talking with many friends about travel recently and realized that we all travel for different reasons.

Let’s say four people fly to Zanzibar in Tanzania.

One wants to escape to a luxurious beach resort. One wants to learn Swahili from the source. One wants to take impressive photos and get Instagram attention. One wants to understand the local music scene.

You could question each of those motives and ask if you really need to hop on a $2,000, 12-hour flight to that place to do that.

If you really want to escape, couldn’t you drive somewhere nearby without your devices? Leave your phone at home and be completely unreachable in a serene cabin an hour away by car somewhere. You might only be an hour away but you’re infinitely away from your regular life if you don’t bring your phone. So that can actually be an amazing escape.

And if you really want to learn Swahili? You can do that in your own home.

If you want Instagram attention, more now, you can challenge yourself to get the attention from something you’re creating, not consuming.

And lastly, if you want to understand the local music scene in Zanzibar – I’m actually using this example because that’s something that I wanted to do. I actually booked a flight to go there and I was going to go stay at a recording studio for two weeks. It fell through at the last minute, but you could hire a local assistant to be your eyes and ears.

If you make the pessimistic assumption that travel will now be near impossible and assume that the cost of a flight goes up 1,000%, then you can be resourceful and find a way to do whatever you wanted to do without actually getting on a plane and going somewhere.

If you really care about this one thing, like the Zanzibar music scene, then you could make a website promoting the Zanzibar music scene before you even know anything about it.

Use your website as a key to get in the door because everybody wants promotion. Everybody’s happy to talk to somebody that’s going to give them some promotion. You could schedule interviews with all the movers and shakers in the Zanzibar music scene and ask a million questions.

You can do all of that from wherever you are without getting on a plane.

Too many people say, “Look at me! I got on a plane to Istanbul and walked around and saw the Grand Bazaar. I can take that off my list and I can tell everybody I’ve been to Istanbul.”

But did you really understand Istanbul by walking around it?

Or perhaps would you have made a better use of 20 or 30 hours of your time instead of booking flights and travelling and figuring out the logistics of picking out a hotel and then walking around the Grand Bazaar?

You could have spent that same 20 or 30 hours reading books about Istanbul, booking one on one phone conversations with people from Istanbul. Find people through friends of friends or go to and ask them a million questions about Istanbul.

You could have hours of one on one conversations with people in a way that you wouldn’t if you were just walking around the Grand Bazaar and everybody’s just trying to sell you something.

A few months ago, I would have told anybody who asked that travel is one of my top three priorities in life.

Now, I’m hypothetically assuming that it’s impossible and by doing so, I’ve realized that it’s not necessary. There are more direct ways to get what I want from the reasons I was travelling.

I can relate to the fourth person in my example. The only reason I was travelling is because I wanted to understand the culture so badly. It’s been funny talking to friends about travel. My friends all shook their heads and said, “No. That’s not why I travel at all. I travel because I just want to get away and be in a different place.”

I’m slowly realizing that maybe sitting in the nature paradise of New Zealand and doing all this over the Internet is a more efficient way to do it.

I’m also not polluting the air as much. Maybe those thousands of dollars I would have given to Delta Airlines or Marriott, I could give directly to somebody who needs it in the place I would have gone.


I really like the creative ways of asking yourself, “What am I really after here?”

I’d be the fifth person in your example [laughter]. Looking back on my travel experiences, what I really appreciate about it is the journey of self-discovery and culture shock.

Putting myself in a completely different environment shocks me into thinking in different ways than I could have imagined.

I’m conflicted because I still feel that travel is one of the best ways to do that. But I do look at the negative consequences of travel.


I’m going to do an experiment and I might even suggest this for you, too. Pick a country that you guys think you would have gone to next and instead, make a little self-directed course where you read three or four books about that place –not just Lonely Planet – but deeper books about that place.

Go watch three or four of the top, all-time best movies from that place with subtitles so that you can understand what’s valued in that culture through fiction, and then use or another random service that’s out there for people that are willing to talk to strangers.

Book twenty hours of one on one phone calls with people from that place and come prepared with a list of 100 questions you have about that place.

In a perfect world, you would be physically present in that country, but since it’s not possible to be physically present there, these things will pull out the same reaction in you. You can still realize how your beliefs match or clash with the beliefs of this foreign place.

In theory, it sounds like a nice idea. Who knows? I might hate it. I might be completely wrong.

But as of right now, if I’m pessimistically assuming I won’t be able to travel anymore, this is a nice way to, in theory, to continue to get what I want from travel.


That’s a great suggestion and it’s definitely worth exploring.

We came to the realization you share a lot about how you spend your days. I think you have the nickname “The Machine” [laughter].

It seems like you sleep for about 5 hours each night.

I need a lot of rest and I feel like I never get everything done. How do you have the mental energy to do be so monomaniacal?


People always seem more impressive from the outside.

I usually feel the same way as you. I can’t get it all done. That’s why I am pretty sleepless.


It’s good to know you’re human like us [laughter].


Derek, thank you so much for coming on the podcast. This was a great conversation and I learned a lot.


Thank you. You too. Thanks for having me.


Is there is there any place that you want to direct people to find you?


Zanzibar [laughter].

Go to I don’t really use social media. Everything I’ve ever done and will do is on my site. And just like Alasdair emailed me back in 2012, you should click the “Contact Me” link and send me an email and introduce yourself and say “hello.”

I love meeting people from all around the world. It’s one of my favorite things about what I do. So, introduce yourself.