Derek Sivers

Interviews → Tim Conley from Foolish Adventure

On “changing your operating system” - my metaphor for making deep changes in my life.

Date: 2013-01

Download: mp3

0:25 Tim:

Welcome to another episode of The Foolish Adventure Show. I’m your host, Tim Conley and I’ve got a very special guest here. Mr. Derek Sivers of CD Baby fame, who had sold his company in 2008, which we’re not actually gonna talk about here. There are plenty of interviews of Derek out there about the rise and the sale of CD Baby. But what we’re gonna talk about the time between the sale and now. This is going to be more of a mindset episode and not a how-to episode. So, what’s up Derek?

1:00 Derek:

Hi Tim! What’s funny is that when I sold CD Baby, I thought that my greatest hits were behind me. You know like somebody who had a hit single in the 80s and that’s all they will ever be known for. I thought it would go onto my gravestone. “Here lies Derek Sivers. He made CD Baby and that’s about it.”

Then I spoke at all the TED conferences, a year after I sold CD Baby, and now I’m actually more known for that. As I go around the world, everybody’s like, “Hey, you’re that first follower dancing leadership guy from TED! Rock on Dude!” Then people sometimes ask, “So what do you do besides speak at TED?” That’s all they know me for now!

1:45 Tim:

So the sale happened in 2008 and from the stuff that I heard you just wanted to decompress from that. So where did you go? What happened to Derek after the sale?

2:00 Derek:

I don’t know if it was decompress as much as de-brainwash. In short, I wanted to change my operating system.

I think all of us have a way that we do things. Say when you’re like a teenager or early 20s, you’re constantly learning new things, growing, changing everything, deciding what your major is gonna be, then going out into the world and getting jobs, doing things, and changing wildly all the time.

Then people often hit a point in their 30s or so, where they just say, “Well this is who I am. This is the way I do things.”

2:37 Tim:

Ah, that just gave me shivers! Ah, that doesn’t feel good at all!

2:41 Derek:

Yeah! You know, “This is the way I like my eggs. This is the kind of music I like. This is my favorite team. This is where I live. This is what kind of person I am. I’m a social person, or I enjoy a beer on a Friday. This is who I am.” And people get that weird kind of stuck.

Here’s a version of that in the music business: I would go to these music conferences and I’d be invited to speak on a panel. It’s always a panel. And the moderator would ask: “What is the future of the music business?” The guy who’s in the business of selling MP3s would say “The future is selling MP3s! People want to buy MP3s”, and the guy who’s in the business of streaming radio would say: “People don’t want MP3s! People just wanna turn on radio but have it world-wide.”

Then they’d turn to me, and I was in the business of selling CDs and distributing things, so they’d expect me to say that the future is that. But all I could say is: “Look nobody knows the future. Nobody! Ben Bernanke doesn’t know the future of the world economy and he controls it! So even the people who control this stuff don’t know it. The record labels don’t know the future of the music industry and they somewhat control it. Nobody knows! And anybody who claims to know if full of shit and not to be trusted! Because they’re obviously not thinking clearly or being honest if they claim to know what the future is. Because they don’t. So if they’re opening their mouths and telling you what the future is, they’re lying. They’re not being honest. Or if they think they know, then they’ve deluded themselves or not thinking clearly.”

I felt that at CD Baby I had been seeing the world through one point of view for 10 years. I was immersed in my world of independent musicians mailing me a box of CDs directly and having me sell the physical CDs and distribute the digital files off to iTunes, Amazon, Napster, Rhapsody, etc. And that was my whole world for 10 years. I was very head-down at work on that.

The day I sold CD Baby, I went to sleep that night with an empty head and a big smile. I was like, “Wow! 10 years of my life. I’m done. I’ve moved on.” It was like graduation day. Wow, I just finished. I went to sleep that night so empty headed.

Then I woke up the next day, had breakfast and by lunch I had a great idea for my next company. And I started sketching it out. It’s called Muckwork. It’s gonna be this service firm, that’s like a professional network of assistants that are already pre-trained to help musicians with all the things that musicians need help with, so that musicians don’t need to kind of micro-manage them. They can just dump their problems on us and we’ll take care of it.

I was so excited about this idea that I immediately, like that day - January 18th is the day that I had the agreement to sell CD Baby, January 19th is the day that I woke up and had the Muckwork idea - (It’s kind of cute that you can see if you do the “whois” on the domain name, that everything was registered on January 19th, the day I had the idea.) Programming and coding, I registered the domain name, I did all the programming. I worked on that for a few months. I even hired a manager, and I was just about to launch it....

Then I had the feeling that I hadn’t yet changed my operating system. “If I do this, it’s going to be like CD Baby part 2. Like my life will not change!” Same guy doing the same thing in the same way, but just with a different company name over my head. I am too into the idea of personal growth and development to do something like that.

So, I kind of just quickly looked at my situation before charging people’s credit cards and beginning. Once somebody pays me the first dollar, I’m on the hook to deliver. And wait a second: I don’t know if I want that yet. So, that’s when I kind of intentionally put the brakes on it. I let go of the manager I hired. Luckily he’d only been working for me for a few weeks, so it was no hard feelings. And I lifted my head up.

I often think of life as having different phases. Sometimes you’re just head down and just working. And then sometimes you lift your head up and look around and see what’s up.

7:03 Tim:

So when you did this lifting your head up and taking a look around, doing a complete operating system reboot would be pretty difficult for any human, because we are so ingrained in our culture, our language, that sometimes even dictates our behaviours, and to do a complete reboot? What did you start with?

7:23 Derek:

Reading lots of books. Lots of non-fiction books. Particularly a lot about psychology, behavioural economics, studies of happiness - which is a fascinating idea, I’d like to study it directly. Learning what makes people happy, and taking it to heart.

Y’know there’s a cognitive fallacy that we all have, where we think that statistics don’t apply to us. When you hear “9 out of 10 people bla bla bla” you think “Ha, well I’m that 1 out of 10” And we all have that. 90% of people think they are better than average drivers. People asked in a cancer ward in the hospital, 95% of cancer patients say that they are in better health than most cancer patients. So it’s amazing to think that 45% of them are wrong. Like half the people that think they’re better than average drivers are wrong! They are actually worse than average drivers!

Then having to look at myself through this new fact. I think this is what I mean about changing your operating system. It’s taking in new knowledge and actually living by it, applying it. Not just reading and going “Hm, alright, well that’s interesting,” then going back to my normal way of doing things.

8:39 Tim:

So to be able to apply that… Let’s take happiness. I find that very interesting because we all have concepts of what’s going to make us happy, even while we’re not currently happy. So we have that, and when you read something about how you can be happy, the act of being happy. How do you put that into your life? And this is from somebody who’s now technically retired, right? What did you do that you could make use of that knowledge? Build a framework? Or just sit back and think happy thoughts?

9:11 Derek:

I guess that’s where your personal preferences come in.

Even in Buddhism, I never understood people who just sit in a temple on top of a mountain or under the Bodhi Tree and just sit there and smile. That’s not enough for me because I’d feel useless in the world if I’m just sitting there being happy. What’s amazing is that just a couple of months ago I went to Thailand, I didn’t even realize there was such a thing as active Buddhism. I’m not an expert on this, but apparently there is a whole chunk of people that believe in applied Buddhism, like this idea of be happy and go out and do things that improve the world. That it’s not enough to just sit there and be happy and meditate. Yes mediate, find your peace, and then go out and make the world a better place. So that’s the one that appealed to me more.

But I felt like I needed to shatter my habits. So my little mini slogan was, “Wherever you used to say ‘yes’ say ‘no’ and wherever you used to say ‘no’ say ‘yes’.” Reversing all of the things you used to do and trying the opposite.

10:25 Tim:

I want everybody that’s listening to actually think about that right now. Think about what it would feel like to actually say “yes” to something that you would normally say “no” to. I guarantee you, there’s going to be a twinge of fear, because that’s scary as it can be.

10:38 Derek:

Oh, absolutely! Well, that’s the whole point. If you’re not scared, you’re doing something wrong! The whole point is to find the fear.

I’ve had this slogan ever since I was a teenager. “Whatever scares you, go do it.” I would use that even on a little micro level. I see the gorgeous girl across the room and I’m like “Ahhh!” terrified to talk to her! Then I remember, “Whatever scares you go do it! So here we go..” and I would just walk up to the girl that intimidates me and say hello. Then of course she’s wonderful or not, whatever it is, but I walk away no longer scared. Now I just have that approach through life. I think whatever scares you go do it, because then it won’t scare you anymore.

I had never had an interest in travelling. I had never had an interest in anything but working. I was absolutely - from the age of 14 until 38 - just a workaholic. In college my nickname was “the Robot”. The guys would tease me that I wouldn’t even join them for dinner. The cafeteria had free meals. I went to Berklee School of Music. Everybody would stop for an hour at 6:00 and hang out and eat whatever the cafeteria food was. But I would just breeze through there, and slap some peanut butter and jam on some bread, grab some carrots sticks and throw it in my backpack and head up to the practice room. Friends were like: “Dude.. Common man, hang out!” But I'd say, “I don’t wanna hang out. I gotta work. I gotta practice.” I was always the first guy in the practice rooms in the morning and the last guy there at night. Everybody was going out to parties on the weekend and I would take that opportunity to read next year’s assignment, and do my homework in advance. So I was that guy that would get teased for never relaxing.

So to me, the idea of going to India for a month and walking around and experiencing it was so against my grain, y’know? That’s not me! That’s not what I do! So, therefore that’s what I need to do.

There were a bunch of examples that are like that. I just did a bunch of things that were not me, in the name of learning and growing, experiencing new things. The most obvious one that people point at is my wife.

I met this gorgeous girl in NYC. She was born in India, grew up in a Muslim family, and we had only been together a few months when I said, “Come out to California with me. Let me get you out of NYC. Come hang out with me there.” Because that’s where I lived. That’s my place! And she said: “Well I can’t. My Mom still thinks I’m a virgin. I can’t go with you unless we’re married.” I was like, “Hmm, married huh? I can do that.”

So we had a Muslim wedding. And to make her parents happy I said a few syllables. In fact I Googled “How to convert to Islam” and apparently all you have to do is say these two sentences. I just memorized them phonetically. It’s just “Ash hadu alla ilaha illallah. Ash hadu anna muhammadar rasulullah.“ You say that in front of another Muslim and you have now converted. That’s it. So I read that, and I was like. ”Pffft! I can do that!“ I’m cracking up. Oh wow, I’m gonna do that. This is ridiculous. I was like ”OK, here we go.“

In the name of changing my operating system, it’s not like I’m gonna actually adopt new beliefs or anything like that but the change for me there was actually doing something that is not me to make someone else happy. I had never done that. I’m a California kid. I had always been so proudly, defiantly individualistic. I only do things for me. Always the rebel. So the idea of me, even just having that understanding how this would make her parents very happy. If I say these two sentences. It would let them tell the relatives back in India that their daughter had a proper Muslim wedding. Means nothing to me, it means everything to them. So here we go.

14:56 Tim:

That’s something I’ve always had a problem with, is doing things that for some reason I am against, right? It doesn’t mean anything to me, so therefore I shouldn’t do it. And that it something I’ve struggled with, is opening up and allowing other people’s feelings to actually get into my life. And that is something that I still struggle with today, because I don’t actually see my self as actually that empathetic. To look at, oh, y’know what would this really mean to someone else and even further for you, for your wife. Yeah, you could understand it for her, but why that extra layer, y’know? The family, then even further afield, the family back home. For me, that’s always been a struggle.

15:40 Derek:

I guess this is what fiction is good at. I don’t read a lot of fiction books, but I do watch a lot of movies. And when done right, the whole idea is to help you get into somebody else’s head really, and understand their process. I guess when fiction is done deeply and done well, when books often excel beyond movies that need to keep things kind of short and entertaining, it’s this idea of really getting into someone else’s head.

Like I don’t know right now whether you consider yourself liberal or conservative, but what’s fascinating is that all the places I lived were just extremely liberal. I lived in NYC, Los Angeles, San Francisco, Portland, Seattle. Y’know, all of the bluest parts of the bluest states, right? Then it was kind of cool starting to have friends, that were extremely conservative, and even going off on the whole Obama birth certificate thing. Having those people actually be friends of mine, that I love and care about. It’s kind of fascinating to get into the whole different mindset. Because it’s not just about the president. It’s like a whole different world view of the way things should be. And getting back to traditional values and all that. Whereas I’m always trying to get rid of traditional values. And how do you even stay dear friends with somebody that looks at the world in different ways? Well, you get into their head.

I guess we all have different sides to ourselves. Like, even if you’re 99% a certain way, like say introvert/extrovert or something, most people will say: “Well I’m kind of both. I’m mostly introvert, but sometimes I like to go out and be with lots of people.” It’s kind of like that. You can understand the other way of looking at things, even if it’s a smaller part of you.

I guess now is a good time to transition into talking about world-travelling, huh?

17:37 Tim:

Yeah, because having a world view and having it change. That is something that impacted me as well, when I left home. I couldn’t wait to leave home. I grew up in rural southern Illinois. And I knew that the world was awesome, because I could see it on TV.

17:52 Derek:

And then you found out you were allowed to leave!

17:54 Tim:

Yeah. But I grew up really not knowing how to leave. And my only thought was: “Oh, I’ll join the military.” So I looked around at what was available for militarily service. I was like OK, I don’t wanna be on the front lines, so the Marines and Army are out. I don’t wanna be stuck on a ship with a bunch of dudes for six months, because I like the ladies a little too much, and back then there were very few women deployed on the ship. And didn’t want to join the Coast Guard, because well that wouldn’t get me overseas to a certain extent, and I didn’t want to be involved in the drug war, because that’s pretty dangerous living too. And so that left the Air Force. So I joined the Air Force to travel the World, and they sent me to Texas and then to Arizona. And I had to travel on my own dime.

But one of the great things that really helped me out was that I grew up in a very racist area of Southern Illinois called… Southern Illinois! LOL. I always knew there was something wrong with racism. I didn’t know what it was, but I alway knew there was something wrong with it. And then I got into the military, and it was fantastic. Because I met the very first Puerto Rican man I’d ever known and he was just a couple of bunks away from me. Met my first Filipino man. And being able to become very close friends with Blacks, Hispanics, Asians, it was amazing. It was one of the most eye opening experiences of my life. That really rebooted my operating system, because I knew mine was kind of broken. And then I got into that one and then the military said. “Oh no, you’re not going to act like that. That is un-acceptable behavior in this environment,” and it was amazing. I loved it. And so then world travel really broke some of the cultural scripts that I had been ingrained with growing up.

So did you travel a lot up until you said you were working a lot? So did you travel much when you sold the company?

19:57 Derek:

No. I had the lucky benefit of when I was 5 years old, we lived in Abingdon, England for a year, because of my Dad’s work. And while we were in England we spent a lot of time in Sicily, Madrid and Paris.

At the age of 6 I moved to Hinsdale, Illinois, about 25 miles outside of Chicago. That’s where I went to grade school and high school and stuff. So I guess you can say that’s mostly where I kind of grew up.

When I moved from England to Hinsdale, even though I considered my self a California kid, I had an English accent from living in England for a year. Everybody called me “the English kid”! I was like (in an English accent): “I’m not from England, I’m from California! Mummy, tell them. Oh God, I hate England! No I’m from California!”

So I guess I’ve always at least had an awareness that there’s a world out there that you could actually live in and not just vacation in. But no, except for that thing when I was 5 years old, I had not travelled at all.

I travelled a lot around the US. I lived a few years each in Chicago, Boston, New York, Woodstock, Portland, Santa Monica, San Francisco and Seattle.

But when you’re in America, you feel that you’re at the center of everything. Because whether it’s Hollywood, the media, every movie, every TV show, everything is set in America. Everybody has American accents, except for the occasional odd foreign film or something.

21:15 Tim:

And all the aliens invade the United States!

21:19 Derek:

Exactly! That’s where they go, they’re not invading Uruguay. So, you can feel you’re in the middle of everything.

What’s amazing is that after leaving, culturally and in many ways, I realizes America is off on one far extreme of whatever chart you make. America is a very extreme end of things. One extreme end it’s not the middle.

So I was almost 40 years old, and I had really spent my whole life in the US, except for that one year when I was 5. So that was a big inspiration for me.

I’m on this mission to change the way I think, and move ahead in life instead of getting stuck in ruts. Especially when you sell a company and it’s like “Now I’m rich.” It’s so easy to just get stuck in a rut and be the cliché guy either drinking his margaritas for life or being the sad ex-success. Like somebody who had a big hit long ago and now is just stuck in those glory years. Y’know? The 80s musician trying to do things the 80s way still.

I wanted to make it impossible for me to get stuck in a rut. So my mission was to spend the rest of my life outside of the US, mainly because I loved it too much. Santa Monica in particular. When I got to Santa Monica, I just felt “This is it, I have arrived. Like I love this place. I love these people. I love the food. I love the weather. I love everything. This is it. This is my home. This is where I belong.”

But that feeling kind of scares me, because it’s like that thing when people get to a certain age and say “This is who I am. This is how I like my eggs. This is where I live.” I didn’t feel it was time to stop progressing, even in my physical location. So my challenge to my self is to live the rest of my life outside the US, because I love California too much.

I went to New York City for 3 days, passing through for a friend’s wedding, and I met this gorgeous girl and we had this great first date, we’re all swooning over each other. So on our second date I said, “How would you feel about leaving the US and never coming back?” She looked at me for a second, kind of squinted and said, “Yeah, I could do that.” And so then we had a third date and that’s my wife.

She’s joined me on this mission to spend the rest of our life out of the US, even if it’s uncomfortable. Even if it’d just be the easy and comfortable thing to just go back to Santa Monica to what I know well. It’s the idea of kind of forcing yourself to keep progressing. And so far we’ve only lived in pretty comfortable places. I mean we’ve lived in Singapore…

24:40 Tim:

… one of the most modern places in the world!

24:44 Derek:

Yeah, exactly! Everybody speaks English. She grew up in NYC, so Singapore’s another big city. It’s very easy and comfortable for her. The bigger challenge is the idea of this being a stepping stone to the idea of living somewhere like Brazil or Taiwan, and the idea of staying long enough until even that feels like your comfort zone. Can you imagine?

Right now I don’t speak Portuguese, I don’t know hardly anything about Brazil. But could you imagine what it would do for your life to move down there and put up with some initial discomfort and stay until it becomes your comfort zone, so that Brazil just feels like home? And Portuguese - you’ve forgotten that’s it’s your second language, cause it feels like your first, and all your friends are there, and you get it, and the mindset feels like your comfort zone?

And even better, that once you get to that point, then you do it again. Then you go to Taiwan. And at first it’s uncomfortable and it’s difficult, and then you slowly adapt and then it feels like home. And then you go to Berlin and do it again.

25:51 Tim:

Yeah, I found that when traveling I get drawn to comfort zones, where expats are everywhere. When you’re totally out of your element, like my first trip into Asia, I’m as shiny white as can be, and I was about a good 6 inches taller than everyone around me, and I was just being stared at. I’m riding on a bus in rural Sri Lanka and I’m being stared at and touched. It was a really weird experience. So that culture shock really drew me to hanging around other travellers, because it felt comfortable. Even though Americans try to pretend like we’re not much like the Europeans, but we’re very close. As soon as you travel you find out just how closely aligned we really are. And I’m hangin out with Europeans and everything and I’m thinkin’ “Oh man, how cultural of me” right? Where I’m hangin’ out with a guy from France and a woman from Germany and all this yet not hanging out with the people that I actually came to see.

So, how do you break from that comfort zone when you’re travelling?

26:56 Derek:

I think the main difference is to really live somewhere instead of visiting somewhere. I mean you could do it short term, you could just make yourself talk to people that you’re perhaps intimidated by and give the patience to get deeper.

I think whenever you first talk to somebody that’s very different from you, the first you thing you notice is difference in looks. You talked about racism, and the funny thing about racism is that you only notice somebody’s race for the first few minutes. Then it just disappears, and then you’re just talking to a person. If somebody would to say: “Hey, who was that Chinese guy that you were talking to?”, you’d think “Oh him?” You’ve almost forgotten their race, because it’s just a person.

Then to me the next level is the accent or the language differences. That takes a little longer to get past. To kind of hear through the language barrier and communicate heart-to-heart, despite your missing words or misunderstood vowels. Then you can do that when travelling. Like even if you just go somewhere for a week.

When I went to India for the first time, at first I was terrified. Mostly thanks to a panic-stricken friend of mine who had been there once years ago and right before I left warned me that it was the most horrible place on Earth and that people are gonna be clawing at me and yanking money out of my pockets. Terrified me. So I went there with my guard up fully, right? Like prepared to be attacked. And I kind of hid at first. I hid in my hotel room. I’d go on little walks around then I’d go back to my hotel room and read a book.

It wasn’t until my last week there that I pulled up my CD Baby database and I emailed some musicians that lived in Calcutta. “Hey I coming through Calcutta for a week, would you like to meet up?” Until then I was scared of doing that, y’know I just wanted to be alone. So I set up like three different meeting with three different musicians from Calcutta. And with each of the three people we sat around and talked for hours. Unfortunately it was my last week there. I wish it was my first week, because then I finally got it. Then I kind of felt like…

29:20 Tim:

… it would’ve changed your whole experience had it been earlier?


Yeah! They spoke English. And, yes they had the accents, but y’know that disappears after a while. You hear through it after a while. We were sitting there having a really great heart-to-heart talk. It was this bass player from Calcutta and he was telling me about life in Calcutta, and the music scene there. Dude, I felt like I was hangin’ with somebody from Illinois. Y’know? It just felt as home as anything. And that was only just one week in India.

Now imagine that you decide to live somewhere, which is even a self definition thing. Like “I’m living here.” vs “I’m visiting here.” So when people say: “Where are you from?” you say: “Well, I live here now, but I moved here from the US” or something. It’s just a different status. But then it’s getting to know people deeper, having a circle of friends that you hang out with and you see each other every week. Get to know them dearly. Yes, they grew up in a very different environment than you, but you find your common ground. And this to me was the cool thing about it.

So we moved to Singapore two and half years ago. It’s an interesting hybrid where it has all the modern amenities. It has drinkable water and fast internet and stuff. It’s a very comfortable place to visit. Everything works. It will feel familiar enough.

But man, under the surface, there are some deep world-view differences. Actually my best friends in Singapore are native Singaporean. They’re very Christian. They are very conservative. And the Asian mindset: It’s one thing to have somebody tell you the Asian mindset is more collective than individualistic. (I’ve heard that a lot in my life and I kind of went “yeah, yeah, OK, whatever. ”) But to really get to know that mindset and to have people that you know and care about tell you that they chose a profession that they didn’t want to do because it was good for the family. My first reaction as an individualistic American is to say: “No, that’s wrong. You gotta stand up for what you wanna do man. What you wanna do is important!” But to understand that no, that isn’t right. That’s one way of looking at things.

That’s that whole thing I was talking about where America is kind of off onto one far end of the spectrum of individualism. Whereas a lot of the world values things much more by how good they are for the group. In Singapore in particular, the priorities are what’s good for your country and what’s good for your family. Only one or two generations ago, most people in Singapore were in poverty. It’s really lifted itself out of poverty in just a generation or two.

So when the parents say: “No, you’re not going to be a poet, you’re going to go to a good university and you’re going to get a good paying job at a bank.” It’s kind of non-negotiable, because you’re expected to take care of your parents. There is no social security that’s going to take care of your parents when you’re older. It’s up to the children to take care of the parents. So if you say: “I’m just gonna follow my passion and be a poet,” you’ve just told your parents that they might die sooner than they would’ve if you could take care of them well. It affects the whole group. And so you do what’s best for the group, not just what’s best for you.

I thought of a good way to explain this to a friend of mine. A friend of mine was having a hard time understanding this where it all sounded too high-level. So I said, OK, imagine if you found a car unlocked and the keys were left in it. And somebody were to say: “Hey Dude, you should totally steal that car”. And you say, “What are you, insane?” Like that’s just wrong. Why is that wrong? Well because it’s bad for society. It’s not what you do. That’s stealing from someone else. You have to be a sociopath to think like that. Well, that’s the way it seems to be too individualistic in Asia - you’re seen as somewhat of a sociopath. If you say: “Well yeah, I wanna be a poet, even though my parents want me to be a banker.” It’s a little bit like stealing a car and driving away. It’s just bad for the group. It’s bad for everyone. Why would you do this silly idea of following your dreams when you can do the thing that’s best for the group. You know what I mean?

33:52 Tim:

Yeah. One of my closest friends in University was from Taiwan. Over some drinks he admitted to me that he was being very selfish, he was dragging out his college education. We were both in Architecture School together and he was dragging it out. He’s like: “I really have to graduate within the next couple of years, because I have to go back and I have to start adding to the family estate.” He’s like: “I’m the oldest and I’m also a son. I have a ton of responsibility on me, so right now I’m kind of leeching off the family right now.” And he felt really bad about it. And for me as an American, I’m like: “Whatever. Like why would you even think like that? That’s insane.”

It took me a while of being friends with him for several years to really understand just how much pressure he was under. Because here he is in the US to get a great education, but also being able to look around and say: “You know if I just stayed here, my life would be amazing.” But instead he knew he was going back to Taiwan and do his duty to his entire family. And I had huge respect for the guy by the time we finished school. I understood exactly where he was coming from and why it was important for him to go back and do what his family wanted. Even though he wanted something else that he could’ve got in the US.

35:23 Derek:

Yes! And what’s so hard to get over as an American, is to not think that that’s wrong! Y’know? I still, I find myself - even right now as we’re just talking about it - cringing and still feeling like “That’s wrong! He should stand up for himself and do what’s best for him!” But no, hold on, hold on. That’s my American roots talking. That’s just one way of looking at things. That’s my American point of view.

My whole mission of not living in the US again - it’s because I feel like I’m already about American as I can possibly be. I get it. I lived in five corners of America. And it’s true, I haven’t lived in Mississippi or Montana yet, but for the most part I get it. I get America about as much as anyone can. And now it’s time to push out of that. So it’s still hard for me to get over my American way of looking at things.

What’s so cool, is to have dear friends now that are the opposite. When I talk about my individualistic things, they cringe because they grew up in India or Singapore, and for them it’s so hard to get over the feeling that individualism and following your passion is wrong, y’know? It’s so cool to be really close to somebody that sees it from the other point of view.

36:43 Tim:

So the time you spent in Singapore - I read your recent post about global thinking vs local thinking and you had decided you were really gonna think local in Singapore. Was this business or music focused or was it a little more holistic?

36:57 Derek:

It was holistic. It was just everything. It was entirely like, “I live here now.” I’m a permanent resident of Singapore. It’s the equivalent of getting a Green Card in the US. I’ve got permanent residency in Singapore. I might even get citizenship someday. I’m here. So, I want to get to know my community. I want to be a part of the community, and just immerse myself totally.

For the last two years, I’ve been totally immersed into the community of Singapore. Mostly just giving, in every way I can. I was immediately, upon moving here, tapped by every university, group, hackerspace and everything, asking, “Come speak to our group. Come speak to our class. Come speak to this. Come speak here.”

So I did a lot of speaking, a lot of mentoring, and a lot of meeting. I had hundreds of one-on-one meetings. I spent a few thousand hours of the last couple of years just sitting down one-on-one with people. Mostly just letting them pick my brain. It’s always somebody else initiating it saying, “I’d really like to meet with you. I have this idea for a business. Can I pick your brain?” and I would just always say yes, because it’s like well, this is my new home, so yes!

I did really most of the last two years. Online I appeared to be pretty silent. Online people would say, “Hey Dude, I haven’t seen a new blog post from you in like 4 months!” But it’s because every day, for 6 or 8 hours a day, I’m giving to my local community here. Meeting with everybody that wants to meet with me and letting everyone pick my brain. Speaking to every group that asks me to speak.

I think I finally had to admit slowly to my self that it was very one-sided. Not 100% one-sided, because I definitely got something out of it. With every person I speak to, of course, I learn something as well. But the nature of the conversations, not quite as lopsided as this one where you said: “Can I interview you?” That’s designed to be a lopsided conversation. But sometimes they were almost this lopsided. Like people who had a bunch of questions that they wanted to ask me. Wanted to ask questions about what I had learned in life or from experience or whatever. So, I would do most of the talking unfortunately. But I would learn a little something about Singapore or about their mindset.

Then at the end of last year, I realized what I really need to do in my life is get back to the idea that I have paused for almost 5 years ago now - that Muckwork idea that I was describing. Really, it’s still gnawing at me. I still think it’s worth doing. This company idea that I had the day after I sold CD Baby. I still wanna do it, and it’s been on hold for 5 years and it’s been gnawing at me. I really think that I need to stop doing all this one-on-one meeting, and I need to just focus on my work.

Around this time I read a few books that really helped speak to that feeling. The author’s name is Steven Pressfield, and he’s written 3 different books about this: “Do the Work”, “The War of Art”, and “Turning Pro” They’re like three of a series, speaking to the same thing. He’s a novelist and he calls it “The Resistance”: That feeling like when you’re sitting down, “facing your demons”, forcing yourself to try to sit in that chair and work, even though everything in you just wants to get up and grab a snack or take a nap or watch TV or call a friend. But no, you need to sit in that chair and wrestle through this difficult paragraph or chapter or idea or whatever it is.

Looking at my actions in that new light really, really resonated with me. Like sometimes if you’re reading something and you hear some new bit of information you go “Hmm that’s interesting. I never thought about it that way before.” And other things you hear and they just hit you in the gut. Like yeah, that is something I’ve known and felt all along and just never put into words before.

41:23 Tim:

Because you were resisting it!

41:25 Derek:

Yes! And for five years now!

Like I told you earlier, how I had that company idea, the day after I sold CD Baby, I spent a few months on it but then I halted.

We spent most of this conversation glorifying the world traveller, nomadic, adventure seeking culture of rebooting my operating system kind of life. But what’s kind of crazy is to look at that all again through a different lens now and realize that was all resistance! Resistance against just what I really needed to be doing - to shut up, sit down, and get back to the really difficult work of creating something, and struggling through that painful resistance of making it happen instead of just leaping off to another country and learning another culture and having another conversation with another stranger.

The really difficult work can be to shut up, sit down, and do your work. So that’s where I’m at right now.

42:34 Tim:

Ok Derek, so you’ve been battling this resistance of traveling and getting into new cultures. You’re saying it was mostly resistance. So, what’s that going to do now? How has that actually informed what you’re doing right now?

42:48 Derek:

Well, I think there are some things you have to work through.

Like you just said that traveling inspires you and all that, and helps you be more creative. It’s true that all of this world traveling has opened my mind to many things and there is so much more to go. I feel like I just barely begun. I haven’t yet been to so many countries that I still can’t wait to understand more about. So, I feel like I’m just beginning.

But most minimalists are people that used to have too much stuff, and they were pack rats or they were shopping freaks, and they got too much stuff. And then they felt the pain of having too much stuff, and then they got rid of it and felt the greater joy of realizing that you don’t need that stuff, right? So, I feel that way culturally.

Like the last few years I’ve just been like binging on the culture of the world, and not in a leisurely way, it’s actually been in a very focused working kind of way. In fact one of my first projects that I’m gonna be launching soon: For the last year I’ve been producing 16 books about doing business in 16 different countries in Asia. I’ve been to most of these countries recently, and interviewed a ton of people and gathered all this research and hired researchers and all this stuff. So I’ve been really binging on the cultures of the world.

And now that I’ve been through that, I felt the pain of not having created anything. That’s what it took for me to get back to the point of where it’s like, yeah, I could go to yet another country, and meet yet another stranger and learn more about that, but I need to sit down and program.

I wanna make Muckwork happen. I have another idea called Songtest, which is like an open source song feedback contest. I had an idea called Cyrano, like a Cyrano de Bergerac tweet kind of thing for people who don’t wanna tweet for themselves. I wanna sit down and make that happen. Each one of these things, the way for me to make it happen is to sit down and program for a few weeks, or a few months, and launch it. And then maybe lift my head up again, then probably keep my head down for a couple of years, and follow through. Get some momentum for it, and make it something that rolls on its own. That’s the hard work that I need to do next.

The question of where to do it becomes moot, because the focus is inward again instead of outward. So I can sit in my apartment in Singapore, I could rent a vacation home in New Zealand. If anything, I’m still banning my self from going back to the US for now. It’s still too familiar to me. It’s too much my comfort zone. Even though I’m inward-focused, I’d almost rather still be in Brazil, India, Sweden, or anywhere else. We’re talking from New Zealand right now. I’m in New Zealand now. I’m down here for a couple of months. One thing I like about New Zealand is it’s so far away from everything that it’s kind of like the antidote to the travel bug. Because when I’m in Singapore, there are so many fascinating cultures, just one hour away.

46:18 Tim:

A little hop on a plane, right?

46:20 Derek:

Yes! And not only that but with the discount airfare. For like $65 I can be in Bali, or Thailand, or Cambodia, or Malaysia, or Borneo. Ahh, it’s all right there and it’s so tempting. I rented a little vacation place for a few months down in New Zealand to fight the travel bug and stay focused. So that’s what I’m doing right now.

46:44 Tim:

One thing you said that I really liked was how you hadn’t created. I think a lot of people have this hollow feeling in themselves where they know they could be creating - and some of them even attempt to do it through business - but it just doesn’t transfer. They fall prey to resistance. They don’t actually get it done. And that hollowness really ends up tainting their own world view. So how do you take that hollowness that you felt of not creating and turn it around, and actually make something from it?

47:22 Derek:

Do the work. Shut up, sit down, fight the temptation to do other things, to follow your distractions, and just work.

Most of us know what we need to do. That’s what’s crazy! I think in any field, any person, what you need to do is usually painfully obvious. We’re all searching for distractions or reading yet another book with yet some more advice. But no, we’ve heard enough advice, we’ve all got enough advice. Really you already know what you need to do. It’s different for everybody.

For me, it’s programming. In order for all of my ideas to happen, it has to start with the website. To me business is still art. It’s something that I create as a personal expression of something that I want to exist. So the idea of saying, “just hire somebody to program it,” is a little like telling the songwriter in the band to just hire somebody to write the songs for them. It’s like, “Well no, this is what I do. This is my art. I want to write the songs.” So, I still want to program my websites, my ideas.

I’ve never learned JavaScript before. Talking about changing my operating system - I’ve been doing nothing but PHP for 10 years. Then learning Rails. I’ve never touched JavaScript. It always was kind of a silly decoration until a few years ago - it always felt a little like an unnecessary flourishes. Now it’s really become more core. So I picked up a 1200 page book that everybody says is the best way to learn JavaScript. And I’m going through it, chapter by chapter, jotting down everything I’m learning into flash cards and memorizing it all, and spending hours a day just making little exercises for myself. Learning JavaScript with the idea of applying it to programming those ideas that I was talking about.

So how do I combat that emptiness and feeling? It’s just willpower. It’s almost like meditation. Again, I’m no Buddhist, but when you learn about mediation first thing you hear is that yes, all of these distractions come into your head, and you’ll be sitting there trying to stay silent and focused and all of a sudden you’ll think about something that somebody told you yesterday, and you have to just learn to let it go - to say “OK, that’s just a distraction. I can let that go now”, and to let it run back out of your head instead of doing something about it.

I think that a problem of our “always on, always connected” internet thing is that a lot of us, all day long, as soon as you have any kind of whimsy or curiosity or thought in your head, you immediately just type a Google query or go check on something. Let me just see how my friends are doing. Let me just check in. Let me make sure I’m not missing anything. Let me go look at Hacker News or whatever. It’s like mediation: feeling that urge and just saying, “Hello urge, I’m not going to acknowledge you. I’m busy, go away.” To just let it go and not act on it. I think it’s the biggest challenge for me right now.

50:38 Tim:

Very cool. Very cool. So, any final words of wisdom you can give everybody listening? We’ve talked about mostly just a philosophical discussion and giving them just a little bit of what not to do. What can they do? What would you say to people that are ingrained in their life, in their culture, in their rut, but want something different out of life? What can you say to them?

51:04 Derek:

Well, if you’re feeling in a rut, there are 2 ways out of it, and we talked about both of them here:

Sometimes what you need to do is to change everything, to just quit your job, move somewhere different. If you’re stuck in a bad relationship, get out of it. If you’ve been with somebody for too many years and it’s a bad relationship, get out and go be single. If you’ve been single for too many years, well then commit. Y’know? If you’ve been doing things one way for too long, do the opposite.

But then the other way out of a rut - the last thing we just mentioned - is to finally have the willpower and discipline to do the thing that you’ve been avoiding all these years. You know what you need to do. To understand that you really need to do it now. That your life is going to get worse and worse and worse if you don’t act on what you know you should be doing.

For some people that means starting a company. For some people it means joining a company. For some people it mean making calls that they’ve been scared to make, or confronting their parents about something. Whatever it is, it’s usually the difficult, often long thing.

It’s too tempting to say that it’s going to be a short thing. It’s like “Hey, just make that call that you’ve been meaning to make.” No, you need to learn that programming language that you’ve been meaning to learn, and it’s going to take you a year, y’know? It can often be that really long, hard, difficult thing. How about like changing your eating habits? You’ve been eating crap, you need to start eating mostly vegetables, and it’s gonna be hard!

Sometimes I felt like when I was living my travel adventures, jumping off to these new countries and strangers, I often felt that what I was doing was very good for other people. That other people could say: “Wow, that looks so fun. What an adventure.” Whereas telling people no, I need to say no to the 20 people a week that want to meet with me, and say no to the many conferences that want me to come, and say no to all the projects people are asking me to join. And I need to say no to everything, and I need to sit here and spend 6 hours a day programming, and 3 hours a day writing.

53:24 Tim:

Ah, but that’s not glamorous.

53:25 Derek:

Right! It’s not glamorous! It’s not interesting to others. It’s what needs to be done. It’s the more difficult thing.

So only you know which of these two paths is your path out of a rut. It’s really tempting to think it’s the exciting quick fix adventure thing of hopping on a plane and quitting your job and breaking up your relationship. That’s fun but be really honest with yourself that maybe the thing to get you out of your rut is finally acting on the thing that you have been avoiding for years.

53:57 Tim:

Fantastic, fantastic. Derek, it’s been a pleasure. I’m very happy to have been able to sit down and just chat with you for a while.

Can I get your philosophical view on the world and how that informs our business decisions?

54:15 Derek:

I don’t know how much any of this refers to back to business!

54:17 Tim:

Well, I think it does. I think everything we do in our lives, there’s no separation. I use the word business just to be able to say that there is this artificial separation, but what we do in our business is a part of our lives. It’s an active creation. It’s active, as you say art. You can’t separate the art from the artist. That’s why I love these kinds of philosophical mindset discussions. You can’t just go, “I just listened to Derek for an hour and now I can go and succeed in business.” That’s not what it’s for. What it’s for is to, as you said in the very beginning - change your operating system. Put a new program in there. And that new program in time could be the thing that actually helps you out in your business goals.

55:07 Derek:

Yeah, definitely.

The one thing I mention in passing but I didn’t emphasize enough is the importance of reading books. Not just scanning articles. If you think about how many hours and hours you spend skimming articles and reading the news, that quick-fix kind of stuff. If instead, can you imagine if you didn’t do that but instead you put aside two hours a day to pick up some books that speak to something that you either don’t know anything about - like architecture - or to make you a deeper expert in something in an issue that you really care about? So often you learn so much more from that than you would just skimming around.

The idea of thinking something through deeper and then putting aside time to reflect on your perspective. It’s one thing to just sit and read and read and read. Sometimes you need to put aside an hour and half to write your own thoughts about it. Internalize it instead of just taking it in and moving on.

Yeah, you’re right, so it’s inseparable, this whole business and personal thing. It’s funny sometimes when people would want to pick my brain about their business, and they’d say “Here’s my business idea, what do you think?” and I’d be like “Um, I don’t know, what kind of person are you?” It depends. Do you want some big IPO, or are you looking to get bought, or are you looking to have an adventure? Y’know? It depends on what kind of a person it is. You can’t just say “This is my business advice” until you know who the person is you’re speaking to.

56:35 Tim:

Right, right.

56:36 Derek:

And thanks for mentioning that’s it’s inseparable.

56:37 Tim:

Again, I really appreciate it, and I know you’ve got to get your head back down, and back to work.

56:44 Derek:


56:45 Tim:

And I need to do the same over here. So same thing with all the listeners, I want you to go out, and after you’ve taken some time and reflected on your life and put your head down.

56:56 Derek:

And enjoy your foolish adventure.