Interviews → Robin Zander

Robin:

Derek, thank you so much again for coming onto the show.

Derek:

Thanks Robin.

Robin:

There are so many places to start, but maybe just one little piece, before we started this interview I was listening to, not just your old interviews, but some of your old music. I think some of what you’re less known for is you spend the first decade of your career as a professional musician.

Derek:

Yeah.

Robin:

What kind of music did you play?

Derek:

I call that a cross between James Brown and the Beatles. It was kind of pop-funk where my favorite thing was to play all of the instruments myself in the recording studio. So my role models were people like Stevie Wonder and Price that would play all the instruments themselves in the studio. And that was my goal. Yeah it’s funny, you’re the first person I’ve heard in a long time that found that music link on my website. A lot of people have no idea that it’s there.

Robin:

Right. Of course, you’re best known as an entrepreneur and as a programmer and as somebody who’s builds incredible systems and businesses, which we’ll dive into. You have a fascinating story in your book about your first job, even before you started your career as a musician. So if you be willing, would you tell us the story of your library job and how you quit that job?

Derek:

Aah yeah, last time I had a job was in 1992, that’s when I quit my last day job. Which by the way, I didn’t find out until later in life that day job is not a term that everyone uses, that it’s like only us, musician/ entrepreneur types...

Robin:

Gig workers.

Derek:

Right! ...say “day job”, but yeah, I quit my last day job in 1992. The deal was, I was 20 years old, just out of college and got a job at Warner Brothers’ publishing division, which is called Warner/Chappell Music, in New York City, right in the heart of Manhattan next to the 30 Rock building and there is a big huge room that had every piece of music that the company owned, and that was in my room. I was in charge of that room, I was the sole guy in that room. So like every piece of music that came in and out of the company went through me. It was a really cool job. I mean it was at minimum wage, but it was a blast, it was a great way to get to know the music industry from the major label side of things. Because I spent the rest of my career, you know before and after, knowing it from the musician indie side of things. So it was really cool to be in the belly of the beast and see how things work and how people got to record deals and all that kind of stuff. It was really nice to understand that from that point of view.

Robin:

Nice. And in college, I’m backtracking a little bit here, but you are a musician from pretty young. From how old?

Derek:

Well yeah, I guess like a lot of people, at 14 I decided I wanted to be a rock star, you know? So from the age of 14 is when I got obsessed with music, but then I was really really serious about it. I didn’t just want to be famous, I just wanted to be successful by any means. So I went to Berklee College of Music in Boston for three years, I actually graduated. And yet, music was a really from the age of 14 until 29 when I started at CD Baby. Every waking moment was all about me me me me me and my music and projecting myself, my personal thoughts into a public address system and all that kind of weird egocentric thing about being a musician. So I think that’s why, maybe, when I was 29 and started CD Baby that I was really ready to turn my attention to others for the first time ever.

Robin:

Oh, how interesting. Okay. Interesting. So this library job I sort of put it in the category of public librarian handling book, that you were actually still very much, as you say in the belly of the beast, but looking at the music industry.

Derek:

Oh yeah, yeah. It was disheartening in a way.

Robin:

In what way?

Derek:

Because on the shelf were thousands and thousands and thousands of albums by people you’d never heard of, and each one of them, these were people that had achieved the dream, they got a record deal! And I just know so many musicians, that their dream was to get signed and get a deal. And here my shelf was filled with thousands of albums that did get a deal, and you still haven’t heard of them. It was like, oh my God, so even if the dream comes true and you get signed, you’re still not shit.

Robin:

And what did you take from that? Because you went on and had a career as a professional traveling musician. As a gig worker.

Derek:

Yeah. Well, let’s see. I got depressed about that for little while, but then I just kept my attention on the craft and just constantly working on my songwriting and performing and chops and all that kind of stuff. So sometimes, I’ve heard a lot of creatives say this, that whether you’re having a boom or a bust in your career, the craft is the thing that carries you through.

There is a brilliant talk by Elizabeth Gilbert, the author that wrote Eat, Pray, Love, she gave this TED talk about creativity, inspiration and the muse. She started out this talk saying: “I had this giant enormous huge success with this book Eat, Pray, Love, now I’m in this strange position of having to admit that my biggest success is almost certainly behind me. And how do you deal with that? Basically the answer was you keep on writing, like it’s in the craft itself, you just focus on the writing itself.” And I think the same thing with music, you might get famous, you might not, that you just keep doing the best you can grasp it is you’ve chosen.

Robin:

And that kind of a common theme across all of your work. Going into CD Baby, and even since. Where, maybe even in your teenage years or your 20s as you were developing the craft of the musician, where did that come from for you? That intrinsic motivation and desire to continue practicing.

Derek:

Good question. I think everyone has different reasons for doing what they do. So let’s look at one example. People often assume that if you know what someone does that you know why. That’s why the typical American question is “what do you do?” As if somebody says “I’m a doctor”, or “I’m a lawyer”, you think that you now know something about that person. But actually I’d like to suggest that you don’t actually know anything if you just know what they do. What really matters is why someone is doing what they’re doing.

Say for example you’re at a party and you ask four different people “what do you do?”, and two of them say “I’m a doctor”, two of them say “I’m a lawyer”, you think “oh, let me introduce you to this other doctor over here”, because you think “oh, you’re both doctors, you have a lot in common”, but now imagine if you ask them why they’re doing what they’re doing. And one doctor says that her mother died of cancer and she’s vowed to never let somebody die of this cancer again in her lifetime. And the all their doctor, you can tell is just kind of more into the prestige of it. And then you talk to the two lawyers and you find out that one lawyer is really just kind of into the prestige of it, but the other lawyer’s dad was wrongly jailed when he was a kid and he’s vowed to never let anybody be wrongly jailed again. Well now that you know the why, you find out that the why changes everything, and you can’t just assume.

So for me, personal development, has been the sole reason behind everything I do. So even as a musician, recording artist, song writer, I would always sing my own songs for example. And I wasn’t a great singer, so people would often tell me that I should just go find great singer. Like they’d say “Derek, you’re just not a singer, c’mon. You’ve got to get another singer, you’re just no good.” To me, that was just missing the whole point, to me being the singer of my songs was my way of improving my singing abilities. I wasn’t a natural, and it took 15 years of practice before I finally got pretty good, but I did it. After like 15 years working at it, I got pretty good.

But on the other hand, if my goal was just to get rich or get famous, well then yeah, it would have been smarter for me to find a gorgeous, great singer to sing my songs. That would have been the shortcut to fame or riches. But my goal was personal development. So that’s why I not only insisted on singing everything myself, I also produced and recorded everything myself, I did all the engineering myself, played all the instrument myself. Because to me, this was my self improvement challenge. The reason I was making music was as my personal development challenge.

Robin:

So what does personal development mean to you? Maybe, what did it mean to you then and what does it mean to you now?

Derek:

Hmm good question. It seems self-explanatory to me. It’s just improving at everything, right? Yeah, it can be every aspect of life, even giving yourself personal challenges, What’s that word? Whether it’s flexibility or your strength, and I mean emotional flexibility and emotional strength...

Robin:

I often use the phrase emotional resilience for myself.

Derek:

Resilience! Dude, that was the word I was looking for! Resilience, yes! That was the exact word I was looking for, thank you! That even that, for example, it’s not just about I want to lose weight or make more money or something as simple as that, it can be something as vague as I want to get better at thriving emotionally no matter what the situation may be. Things like that. That’s all personal development to me, just being smarter, being better, constantly improving.

Robin:

This might not be something that you have an easy answer to, but that internal intrinsic desire for continued improvement, why do you have that? What is that? This is a question I’ve often asked myself and a lot of people who do sort of resemble that remark. But why you? Why do you have that internal, lifelong drive to continue to improve? Even over fame or weight loss or anything else.

Derek:

I don’t know. I think lots of times we are avoiding something as much as we’re heading toward something. We’re running away from something as much as we were running toward something else. So I think I’m running away from stagnation, and those people who kind of flatline.

I think it’s almost a cultural norm that when we’re kids, when we are in our teens, in our 20s, we’re constantly learning and changing and growing, and especially people in their teens and 20s changed their identity constantly. Whether it’s like “now I’m a punker, now I’m really into meditation, namaste man”, you know, whatever. People change their identity so much. And then people hit their 30s and they just kind of say “well, this is just who I am, this is where I live, that’s how I like my eggs, this is my favorite team, this is just who I am”, and I don’t like that. Especially because our current life expectancy is probably going to be about 100. I don’t think that we should stop when we are in our 30s. So I think I’m constantly, actively trying to avoid that, running away from that situation and towards a constant improvement and change.

Robin:

I don’t want to downplay the profundity of what you just said, but I have this comical image of Derek Sivers running away from the stagnation monster.

Derek:

Well you know, I remember a lot of my drive early on as a musician was as a teenager in Hinsdale, Illinois and seeing that some of the best musicians in high school, these guys that were just amazing guitarists or drummers, with graduate high school and, a few times it really just pissed me off, I see the best musicians in school just get a job somewhere and they say like “well, you know, got to pay the bills” and they’d get a job working for the village of Hinsdale laying pipe or something like that or tarring driveways or whatever they to. And they ended up just putting their drums into storage and they just didn’t really play anymore. As an ambitious musician I just felt like “how could you do that? You are the best at school and now you just gave it up for some stupid job! How could you?” I vowed to never be one of those guys.

So from the age of 14 to 29 that was such a big motivator of mine, I was an absolute workaholic. Even at the Berklee College of Music my friends at school teased me and called me The Robot, because I would never stop to eat or drink, I never went to a single party. Actually I think I went to one party in my three years of college. I would just practice every night till midnight, and I set my alarm for 6 AM, and I’d get up and I just start practicing again, I was just like an absolute fierce monster at practicing. Because I was just so avoiding that situation like “I will never be stagnant, I will never be one of these ex-musicians, I will never do that”, I was just so fiercely avoiding that situation, that’s what drove me for so many years.

Robin:

I see so much pride in being busy, in being a so-called workaholic, in “I’m going to make my thing a success”, especially in Silicon Valley and in business. And yet you call that hustle that you had, that drive that you had avoidance, in your musical years, in your years as a musician.

Derek:

Well that changed throughout the years. Sometimes you’re running away from a scenario, sometimes you’re running towards scenario. So let’s flip it around. So let’s zoom forward to me at age 39. I sold CD Baby for a ton of money and I’ve been surrounded by… I’ve only been doing music for 25 years. For 25 years I’d been doing nothing but music, music business, music industry. And around that time is when I started watching TED talks and I felt like that’s the world I want to be in. I want to expand my horizons beyond music business. I want to be one of those people. I want to be invited to speak at TED. And I want to be a writer/speaker/thinker kind of person. And I made that my new ambition. That was clearly like a going towards kind of goal.

And I pursued it full on. I started saying OK, this is what I want, therefore how do I get there? I think I’m going to need to start writing a lot, I need my ideas to be punchy and succinct and clearly communicated and not vague, and maybe not even nuanced. Maybe just kind of short punchy things that people can read in a minute and spread around to their friends, I need to make a name for myself like this. And I spend like six hours a day working on that specific goal every morning and yeah, about a year later I got invited to speak at TED. Not just once, but three times. So I did three TED talks. So that’s a different kind of motivation, that was like something I was going towards. You’re driven by different things at different times in your life.

Robin:

What was the drive for sort of the space in between being a musician and the TED talks, which was CD Baby?

Derek:

That was all giving back. That actually to me felt quite charitable. So for example, to me the definition of entrepreneur is: it’s all about being of service and giving. Because, this is my personal take on it, business is not about you. People don’t open up their wallets to pay for something because you’re passionate or your following your vision or you’re expressing yourself or any of these other ridiculous self-centered reasons that people have, they only pay for what they need. So get over yourself. Forget yourself. This isn’t about you, this is entirely about them. This is what other people need. Therefore, being an entrepreneur is about being of service to the world.

So for example: you could just stay home and trade stocks on the stock market, or you get a safe job pushing papers around for a logistics company, there are better ways of making money, so it’s not about money. If money is what you wanted, there are other ways to make a lot of money. So being an entrepreneur is about being of service the world.

So for example, if you hear that statistic that 90% of new businesses fail, well that number applies to you too, those aren’t just the other people. You know, they’re not stupid. All of those other people are smart like you and convinced that their idea is going to be huge success, and yet 90% of them fail. So you should admit that you’re not doing this for the money.

And I kind of don’t really get that when people say like “I want to start a business”, and I’ll say “well, doing what?”, And they’ll say “well, I don’t know, I just want to start a business.” To me that would kinda be like saying “I want to write a novel”, “about what?”, “I don’t know.”

It needs to be driven, the work it’s going to take to writing a novel or producing a movie or starting a business, it has to be driven by this burning need for this thing to exist. Like, there has to be specific and need for this story to exist, or this business to exist. Anyway, that’s why to me being an entrepreneur is about answering the calls for help. To create something that doesn’t exist but that people need.

And yeah, that was my motivation when I started CD Baby. I’ve spent the last 15 years being very self-centered and was pretty successful as a musician, like I bought my house in Woodstock with the money I made touring, so I was already kind of living the dream. And on the side, as a hobby, I did this thing to kind of give back to my fellow musician. But then it just took off more than I ever expected and ended up pushing my music career side. But that was fine, I was ready to welcome that change. Yeah, the whole thing felt like quite charitable. The fact that it was profitable was just a nice, lucky circumstance. I was really just doing it to get back.

Robin:

If you were to teach that skill, because I think that so many people to start businesses with the desire to earn money, I’ve done that in the past for sure, rather than to be of service, how would you teach someone? Maybe someone just going into business school now or thinking about what they’re going to do next. How do you teach the skill of the desire to be of service?

Derek:

Well, I wouldn’t necessarily say that they should take that approach, that was my approach. But I think everybody needs to know why you’re doing what you’re doing and optimize for that. So say for example, maybe what you really want is famous, or maybe you want to leave a legacy, or maybe you just want as much money as possible, or maybe you are driven by charity, maybe you want to give and contribute back as much as possible. Or maybe you want personal freedom as much as possible, you want to never have a boss again. Or personal development. No matter what is your main drive, people are always going to be telling you that you are wrong for choosing it. You live in LA, right?

Robin:

I live in San Francisco.

Derek:

Oh, okay. I don’t know why I thought you were in LA. Sorry. Well, let’s look at the Hollywood situation, I lived in LA for six or seven years, and the richest people in Hollywood are the ones you’ve never heard off. Because all of the actors, their careers are really optimized for fame, whereas the investors and producers have optimize their careers for maximum profit.

First you need to know what drives you the most, but then when you optimize for this one, you need to boldly let go of the others. So for example, if you know that fame doesn’t matter to you and you want maximum profitability, well you can be more profitable if you let other people take the spotlight. Because there are other people that are willing to make less money in return for more spotlight fame.

Actually Trump, forget the presidential candidate, but even just as the real estate dude, he is an interesting example where he keeps putting his name on everything. You know, Trump Tower, Trump Plaza, he could actually make a lot more money if he let other companies put their name on it and made it the Sony Plaza or the HSBC Tower, but he’s chosen to make less money in return for more safe.

Point is, no matter what you choose, people are always going to tell you you’re wrong for choosing, that your values should match theirs.

So in my case, people would always tell me how I could be in making much more money with my business. They would just show me “well clearly, you could be making a lot more profits if you would just do such and such”, and I say “oh well, that’s not the reason I’m doing it”, and they say “but you’re in business”, and I say “yeah, well I don’t have any investors, is just me, I’m not doing this for maximum return.” Other people are.

Robin:

And CD Baby was there to be of service to the musicians that you were serving.

Derek:

Exactly. It was there to be of service and the other drive was just my personal development goal of learning how to program the back-end code and also learning how to provide a better service. And yeah, you see this common thread behind my other story too, about deciding to do my own singing for my own songs, then it was doing all of the programming myself when people would tell me “why don’t you just hire another programmer?” Anyway, your question was what would you tell somebody that was in business school or something.

Robin:

Just starting out, exactly.

Derek:

So my first bit of advice is to know your values, to know why you’re doing this, because it’s often, you can’t just emulate others and think “well, this is what Mark Zuckerberg did, So I’ll do that”, because your values, what drives you might be completely different from his. So first, you just need to know your values, and then boldly stick with them, and then optimize for those and don’t let it bother you when people say you’re wrong for being that way.

Robin:

What does to be of service or customer service look like in your life today?

Derek:

Today? It’s really just answering emails. The entire thing of putting my ass on the line and continuing to do things feels like service in a way. Of course it would be simple to just fuck off and disappear and hide, but I think that being famous, for example, is very useful to other people. You know, doing things publicly, doing things in public and for the public is a pain in the ass. But it’s actually more useful to other people. So therefore, being famous or getting famous can actually be a good way of being useful to others.

But anyway, to me right now, my main act of public service that I do every day is I sit down and I read every single email that comes in. So that’s actually part of the reason I do interviews like this, you hear I’m not here pitching anything, I’m not trying to get you to buy anything, so the main reason I do interviews like this is I really like the people that I meet, that listen to an interview like this and send me an email and say hello. Anybody that listened all the way through this, you’re welcome to send me an email and say hello. I answer every email.

Robin:

So, just in the nitty-gritty of that, I’m constantly battling my inbox is what it feels like, how do you manage... how many email do you get a day on average?

Derek:

Surprisingly, only about 20 a day. I mean, after I delete the spam and mailing list stuff.

Robin:

And I’m sure you get requests for all sorts of outlandish stuff, do just say no thank you anyway? How do you...

Derek:

Oh yeah, I say no to everything. I’m just at a stage in my career where, just a few years ago I was saying yes to everything, because I was living in Singapore and I was just at a phase in my life where I wanted to lift up my head and say yes to everything, and meet everyone, and taking all kinds of new input. And I did that for a few years, and it was wonderful. I got all kinds of new input, met all kinds of new people.

And then about two years ago I moved to New Zealand as a symbolic head down, focused on my work, no to everything, no I’m not going to do anything I haven’t already started, like I’ve started some things that are not finished yet and I’m going to put my head down and say no to everything else until I’m done with them.

So yeah, people asked me to speaking at conferences, or like “hey, we’re looking for an investor for this business”, I say “nope!” “Hey would like to ask you if you could help us with...”, “nope!” So as far as like getting me involved and helping with or collaborating or partnering or pitching and all that, my answer is just no for everything. But I do answer every question that people ask.

So I put aside a few hours per day to answer my email. And people ask me crazy giant life questions or business questions or whatever, and I’m happy to answer anything. I enjoy it.

Robin:

What are some questions that you’ve been asked recently? That you are willing to share.

Derek:

Oh God, I don’t know. It’s a big blur, I don’t know. Sorry, I don’t have any specific stories. I thought it was really funny though, that like some kid in India that didn’t give me any context or interpretation just like “hi, my name is Maneesh in India, I’m really upset with my sister, what should I do?” I was like wow, he’s really asking me. Okay, well Maneesh... I don’t know... so anyway, it’s funny, the strange questions I get. But usually they are more career focused. And I’m used to helping with those.

Robin:

What kinds of questions, I promise this will be the last question about the questions you get asked, what kind of questions do you most enjoy answering or do you feel your sort of uniquely suited to? So rather then, okay don’t pitch Derek, but if you’re going to ask him questions, what kinds of questions people ask you?

Derek:

Oh boy. I like the philosophical ones. It’s hard for me to separate business and life, maybe as you can tell. For little while I was mentoring at this business school in Singapore and people would show me their 20 page PowerPoint presentation deck for their business idea and say “what do you think?” And that say “I don’t know. I mean, who are you? What do you want out of your life? Are you the type of person that wants to go public and have an IPO and have 1500 employees? Or are you looking to kind of chill and just have freedom and be profitable that disappear and go surfing in Bali? I mean, what you’re showing me in this PowerPoint kind of tells me nothing, I can’t just look at the business for its own sake. It all depends on you and who you are and what you want.” So I guess philosophy and business is all kind of tied together to me, if somebody just asks me a purely business question, like how to increase their Q3 returns, then I’m a little lost.

Robin:

So many people, even that I meet, and I think in the world much more broadly, are stuck. Are making decisions based on fear, are staying at work because they’re afraid to try something different. And I juxtapose that with your, you wanted to learn music, and you trained like a crazy person for 15 years, and then build CD Baby into something that sold for $22 million to charity, and then wanted to be a TED speaker and then were, three times. It sort of life, from the outside, one might say you’ just coast into these things, right? And it’s easier to say that when you’re not doing all of the hard work involved. What are the traits or the skills that you see that make for that growth trajectory that you’ve experienced?

Derek:

You know we talked earlier about the word workaholic, that I think that workaholic is not something that I feel I am. Maybe I said it earlier because it’s the word that other people have used to criticize me.

Robin:

Yeah, I think I might have put that word in your mouth actually, I think I used it.

Derek:

Oh it’s okay. To me it just feels like this: that I found what I love doing and I want to do it as much as possible. So I’m driven, I guess you could say, by many things, but I’m usually quite driven.

I don’t hang out. It sounds like a weird thing to say, it’s almost like saying I don’t eat. But no, it’s true, I never hang out. Except with my kid, but that’s a different subject. I have years of backlog of things I want to be doing, and so I bounced out of bed at five in the morning and often work until midnight and then sleep for five hours and do it again. That just how I’ve always been, because I have so many things that I want to do in life.

So what’s funny is, I generally feel that I’ve been really lucky. Like I’ve had some amazing luck, which is circumstances and being in the right place at the right time. And I mentioned this to friend of mine, and he said “bullshit man! Luck, my ass! You to reap the rewards of what you are doing, because you were always fucking working, you were working all the time, you did everything, you pursued every opportunity, you’ll learn shit more thoroughly than most people because it’s all you did, because you have no life, no friends, no girlfriends. I knew you in New York City for seven years, I never once saw you take a taxi. You never went out, you never went to any parties, I invited you to a hundred parties, you never came, because you are always working. You are now reaping the rewards of 15 years of doing nothing but focussing on a single goal. Fuck you with your luck! That’s not luck!” Okay all right, good point. So yeah, I still feel it’s luck, but okay, he has a good argument.

But you asked about the traits or the skills. I think you need to do what you need to do whether you feel like it or not. And this is a big one. I mean, maybe this just came out because I had a friend who like, just yesterday, is like sad that she broke up with her boyfriend and she was like “I can’t eat, I’m too sad”,I’m like “fuck you, you can’t eat! You put the food in your mouth and you chew! Because if you don’t do that you die.” I hate this kind of like “I can’t do something unless I’m in the mood to do it” attitude. It really bothers me.

Anyway, you need to do what you need to do, whether you feel like it or not. Most of us know what we should be doing. So it’s a matter of being smart, being deliberate, and planning ahead and being somewhat strategic like I said when I decided that I wanted to be a TED speaker.

But there is this other issue that is a related: not to expect passion. For example, I think inspiration only comes after you start something. So when I hear people say that they are just not inspired to write, or they’re just not inspired to work, I think inspiration, if we can personify it, I imagine her as this muse that will only come to meet you halfway. She will never make the first move, you always have to make the first move. And if you make the first move she’ll come and meet you halfway. So I don’t buy this thing about waiting for inspiration. I think you got to sit down and start working, and start writing, even without any inspiration.

And same thing with passion. I think passion is a feeling you get only after things are going well. Like if you’ve spent years building up your chops, like to say as a kid you did scales for hours and hours on the piano and now you’re quite good at piano, well now you can start to feel passionate about piano, because you’re good at it and you’re feeling some rewards. And now that you’ve studied the subject for years you can hear the language inside music, you can listen to McCoy Tyner playing and you can get what he’s doing and to why he’s so brilliant. And now you can start to feel passionate about this thing. That this idea of like sitting around like “I don’t know man, I’m not feeling my passion”, well it’s because you’re not…

Robin:

So I have to ask, I never heard you get heated before, and it’s really interesting to see this passion against waiting around to find passion. Why the heat? I don’t mind, I think it’s amazing, and I’ve never heard you speak of is before.

Derek:

Maybe it’s that thing I get by email a lot, I hear a lot of people kind of whining about not knowing what their passion is. Or “I want to start a business but I don’t know what I want to do. I don’t know what I’m doing with my life, I’m just not feeling energized. I’m not feeling passionate, therefore and just sitting around an existing and watching all of Game of Thrones and all of Orange is the New Black, because I don’t know what my passion is.”

No wishing, no hoping, lots of action. Daily unpleasant, difficult action.

You know, it’s like this word “happiness” that I think this over-emphasized. Unfortunately in English we tend to use the same word “happy” to mean a few different things. One is this shallow, hedonistic kind of short-term pleasure. But there is also this deep satisfaction you get only from accomplishing something really difficult and rewarding. So I’m not really interested in pursuing this short-term happy, maybe because I’m already happy by nature, it’s not something I really need to focus on so much.

But long-term happiness often requires short-term discomfort. Like say, writing a novel for learning a new language. I mean, learning a new language is fucking hard! And a lot of that work is unpleasant. But man, when you’re actually fluent in this other language, well that’s a deeper reward. So I’m interested in that.

I feel that a lot of people out there are never getting that deeper happiness because they’re so focused on this short-term happiness. It’s kind of like “I don’t know, I’m just not happy in my job, I’m just not happy with what I’m doing.” You know what I mean? And it’s focusing on the short term. Whereas if you are strategic and you see the path where this is going and you do some short-term things, some immediate actions that might be unpleasant, that lead to a longer term payoff, that’s where this feeling of passion and deeper happiness comes from.

Robin:

One of my signs that I’m on the right track is if I’m doing something that I’m afraid of. Not afraid like I’m jumping off a building because I’m afraid of heights, but in the thing that I see in front of me looks scary, that’s almost always a good sign for me.

Derek:

Oh dude, that has been one of my life mottos since I was a teenager. I don’t remember where I heard this phrase, or maybe I even came up with myself, I don’t know, but I think I heard somebody say “whatever scares you, go do it.” And I think hearing that at 17, it just made this profound impact on me, because I started using that rule of thumb in every situation. Even the super tiny ones like: well, there is this gorgeous girl that is totally intimidating right now. Oh, whatever scares you go do it, here I go! “Hi, my name is Derek.” Even on the moment to moment level, or even on a big life level.

So for example, I was living in Santa Monica, California and it is paradise! I love Santa Monica! It is just so… The weather is always like 69°, it is always perfect, it is always beautiful, it’s right next to Los Angeles, which is just such a major entertainment center with so many interesting people. I loved living in Santa Monica. But I loved it so much that I caught myself feeling that stagnation feeling of just like “yep, I’ve arrived! This is the end of the rainbow, this is where I lived from now on!” And you know, like we said in the beginning of the call, there’s been one of my running away from values, like my comfort zone makes me uncomfortable. I don’t like being in my comfort zone. So I noticed that’s what scared me was the idea of letting go of Santa Monica, leaving it behind and going off to places that were unknown and uncomfortable and all the way across the world in a different culture. So that’s why I filled out nine months of paperwork and became a legal resident of Singapore and moved to Singapore for a few years.

Things like that. Even on a big big slow grand level, whatever scares you, go do it.

Robin:

Is there any domain in your life, in your career, or careers where you have actually rested on your laurels? Where you got to a certain point and said “no, I’m done, I’m never going to touch it again, and just going to continue enjoy it as it is.”

Derek:

Good question. Well CD Baby just cruised along for most of its existence. Like, let’s say the first three or four years it was lots of invention and development. But then the next three years just kind of coasted, like I didn’t touch the website at all, the code just worked, the site just ran. And so for three years it coasted. And then say the next one year there was a lot of developments as I added digital distribution to the service. But then the next three years of CD Baby just cruised along again. That’s when the business was coasting, and you could kind of call that resting on your laurels, instead during those times that’s when I turned my attention to improving other things. Like I started a little web hosting company called Host Baby, or I would build new services for CD Baby, or improve the back-end infrastructure.

Robin:

The business was running and maybe even coasting, but you certainly weren’t. Your skill sets and what you were working on.

Derek:

Yeah, I think I’m just not the vacationing type. Like when I read The 4-Hour Workweek book, Tim Ferriss talked about putting his business on autopilot so he could go down to Argentina and learn tango dancing. I’ve never really being that type to go hang out and sit around and do nothing, so I guess I just always have that drive to do something to improve myself.

Robin:

I don’t know Tim personally, but I’ve gone to Argentina and did a lot of tango and it is hard work!

Derek:

Okay, maybe I shouldn’t use that example.

Robin:

Interesting. For you, when does learning stop? Is there a point? I’m thinking about your musical career or your TED talks career, where you were just like “I’m good enough, I’m going to move on.”

Derek:

Yeah, I think it’s when you lose interest. When you no longer want to pursue that path. Like for example, right now, I’m not learning anything more about business. And I haven’t in seven years, because business is not one of my goals right now. But I’ve been learning a lot about psychology, programming, languages, philosophy and other things that I think can help me with my future goals.

Robin:

What are your future goals? Or what of them are you willing and able to share about?

Derek:

Finish programming and then launch my web app ideas that I’m working on right now. Learn French and Mandarin. I’d like to learn two more radically different programming languages.

I think learning a programming language is like learning a spoken language. I think that’s part of my interest in Mandarin for example, is that it’s just so different from English. French is a different thing, because I became a legal resident of Belgium last year too, so I actually have to learn French for that. I think otherwise it wouldn’t interest me so much. But Mandarin, I love how it’s so different from English. It’s just such a different way of looking at language, the written language as spoken language is just so difference with the phonetics, I mean the tones, the pitches changes the meaning and all that.

So same thing with programming languages, that it’s like I spend so much of my day programming. And if you learn a programming language that’s radically different from what you’re using already, it just helps you think in a whole new way.

I also want to hike the nine Great Walks of New Zealand, they have these kind of nine hikes that are kind of like the seven wonders of the world, but for the hikes of New Zealand. It’s like, these are the Great Walks of New Zealand. Just look at Google: Great Walks of New Zealand.

I want to continue to thrive despite adversity, and get healthier as I get older and live to a hundred and be a world citizen and feel at home in almost every part of the globe. That’s like a big one for me, I want to understand all of the different cultures and mindsets of the world, I just find it fascinating. Yeah, those are my goals now.

Robin:

You’ve written about quitting your library job, because you were too comfortable. Would you mind sharing that story?

Derek:

Sure. So here I was working in New York City. I was 22 years old, and when I first took that job it was like a mind blowing. Like, my God, every single day I was learning so much. Plus, I was living in terrifying New York City, which, honestly, in 1990 was a scarier place than it is now. Now it’s all kind of post Sex and the City, post-Giuliani, post-gentrification, Friends, Seinfeld etc. But in 1990 it was still a really rough place that felt dangerous and intimidating and scary, and I was 20 years old.

So yeah, at first I was learning tons. But then I realized, okay I’ve been working here for two and a half years, and the last six months I think I’ve just being kind of coasting. Like I just show up every day to work and I do my job, but I haven’t been learning a ton. And so it was at that time that two things happened.

For one, I read the book Island by Aldous Huxley, and the book kind of describes this kind of paradise, utopia society, like the most healthy society that you can imagine. And they were describing that, it’s a fictional book, but there is a character that’s leading a bunch of kids on a mountain climbing group, and he said something like: that was my physics professor, and now he’s doing mountain climbing? And the tour guide says: oh yes, we all switch careers every few years, we just found it was important to be a well-rounded human being that you should never do one thing for more than three years. You should always switch it up, it gives you all kinds of perspective. Especially if it’s the opposite, like if you’ve been doing a sedentary job for a few years, well now it’s time for you to go do something physical for a few years and vice versa. And I read this just at this time when I had been kind of stagnating in my job, feeling like I wasn’t learning anymore and I thought “that’s it, I’m going to make myself quit and go do something else now, because this is like the learning growing opportunity.”

I was also driven by Abraham Maslow’s hierarchy of needs. The pyramid itself is quite interesting, but I think he said something about it, he said “every day we’re presented with the choice between safety and growth, or safety and risk, make the growth choice a hundred times a day.” And I think I really internalized that as a teenager, and ever since I tried to live by that. Like whenever you do have this choice between safety and growth, you make the growth choice. So originally, moving to New York City and taking that job was a growth choice and after two and a half years, quitting was the growth choice.

And lastly, the other thing that happened is my girlfriend at the time was this kind of child of hippies that lived on a commune in Vermont, and she didn’t even have electricity until I think she was 10 years old, or something like that. And her parents never had jobs, and still don’t, they would just do random odd jobs around town, fixing things for people or taking photos and selling them to the local paper or something. And yet they were able to put their daughter through college. And I got so inspired by their story, because I still felt it was a necessity to do the rat race and go make as much money as possible. But looking at them as an example, I realized that you could lower your cost of living down to almost nothing. And if you can do that, like if you can live on under a thousand dollars a month, well now you really only have to do a few days of work each month. You do a few gigs for a few hundred bucks, and now you’ve paid your cost of living. And it gives you all kinds of freedom to just pursue whatever you want.

So that’s what I did. My rent was $333/month, because I was living with a few different people, just kind of renting one little room in a crappy apartment somewhere. I never ate out, I never took taxis, I just made the way of bringing my cost-of-living to down under a thousand bucks a month. So I was able to quit my job and live as a full-time musician, just because a reduced my costs.

Robin:

Nice. And then that sort of paved the way for you to actually pursue that career as a musician, which you couldn’t have done without that.

Derek:

Yeah, exactly. And you know when I hear people every now and then, kind of say “I’d like to do such and such dream, but I have kids, I have a mortgage, we got a big house, we’ve got a way of life that I need to maintain peers” I think “well, you made your choices in life. You chose this expensive life, and this is the consequence of that.”

Robin:

Yeah. And do you think that that’s a reversible decision?

Derek:

Oh absolutely. If your family is on board, you can say let’s move to the Ozarks. Or hey there is this family friend that has a guest house there almost never using, let’s go live there for free and do odd jobs and quit our jobs. Like yeah, of course. I think in that 4-Hour Workweek book we mentioned earlier, he has these examples in there on a family that decided to go sailing around the world and found out that it only costs $18,000 a year to go sail around the world full-time. So don’t say that you can’t afford this. If you can find a way to make $18,000 a year doing some remote work, then you can afford to travel for the rest of your life around the world.

Robin:

Speaking of families, you have a young son, yeah?

Derek:

Yep.

Robin:

How old is he?

Derek:

Three.

Robin:

What have you learned being a parent?

Derek:

I didn’t pursue parenting with my same ambitious type-A drive. I know some parents that did, and went to read a whole bunch of books on parenting. I really only read the book or two about it when he was first born. And then I just realized that, at least for me, I’m not going to prescribe this for anyone else, this is just me, people love to get into fights about what’s the right thing to do for parenting, some not suggesting that for anyone else, but for me, parenting is just like meditation in a way. Where it’s all about being completely present, undistracted, let go of all other thoughts and just be 100% present in the moment for him.

This is partially because I split my time, it used to be that I would hang out with him every morning from 6 to 9 and then again from 5 to 7 when he’d go to sleep. And now instead we split the week, where I’m on full-time duty from Thursday afternoon until Sunday afternoon. And during those three and a half days I just completely shut down everything. I turn off my computer, I turn off my phone, and I’m just 100% present. We just do nothing but whatever he wants to do. He leads the way, he’s the boss and I just follow to help keep him out of trouble. So if he wants to throw rocks into a river for three hours or just big with a stick in the mud for an hour, well then that’s what we do. I just follow him.

I think the biggest friction I’ve noticed with my other friends that are parents are when they try to make the kids live in adult time. You know, it’s kind of like “hurry up! It’s 1 o’clock, we need to go, hurry, hurry!” The kid doesn’t know what’s 1 o’clock means, like that’s just a silly bit of fiction adults invented. So I found I’m happiest, and he’s happiest when we let go of all clock time, I have no other goals or ambitions, I’m just full on, fully present. So that’s my approach.

Robin:

Nice. When I was working with parents of kids with special needs, and specifically autism, the thing that I would see that was the most useful, even if it wasn’t for a full day or full three days, but you know, for 10 minutes, okay sometimes you have to get the child out of the street because they’re going to get hit by a car, but more often you don’t need to get their shoes tied right this moment. Have you found that that meditation, that that practice of being present has transferred into the rest of your life? Or is it really an on/off switch, where you do it there and not other places?

Derek:

It’s kind of on/off switch, I think the only way that it affected my work life is that I have this deadline now, because I don’t like being conflicted or distracted when I’m with him. I want to make sure that I started up all my loose ends before I’m on duty. So it makes this kind of weekly, or sometimes daily deadline for myself that I have to finish everything that I’m doing now before I’m on duty. So that I just completely shut down.

Robin:

Well Derek, it’s been such a pleasure in such an honor to talk with you. And you’ve been really generous with your time. Where can listeners go to learn more and to keep track of you and your projects?

Derek:

sive.rs is my website. And you’ll see I have my email address in the big font at the bottom there. Because, like we said, I really kind of enjoy the random daily questions I get by email and I enjoyed the challenge of answering them. Even if you don’t have the big question for me, Robin’s listeners are my kind of people, so send me a little email and say hello.

Robin:

Great! Well, such a pleasure. Thank you very much and I look forward to more at a later date.

Derek:

Thanks Robin! Take care.

Robin:

Bye for now.