Interviews → Art of Adventure

Derek Loudermilk:

This is episode 88 with Derek Sivers. Welcome to the Art of Adventure, the show that breaks down how to do something that has never been done before. I’m your host, lead and guide Derek Loudermilk. You can check out all the show notes and articles of the Art of Adventure on derekloudermilk.com.

In today’s episode we have Derek Sivers, founder of CD Baby, best-selling author, frequent TED speaker. He’s on the show joining us from windy Wellington, New Zealand. And tons of people email Derek for advice and today we’re going to distill some of that, his best thoughts on career building and discovering purpose from your work rather than the other way around. He also has this great new project where he shares simple one-sentence directives that he has condensed from over 225 books that he has read over the last seven years. So the category that he shares with us, there is several directives, is how to get rich. This is almost like his version of the Ten Commandments for how to get rich. We riff on the power of location, where you live, how it influences your work and, because he’s a known introvert, we talk about the differences working as an introvert or an extravert. And, this is very special to me, I’ve been a huge fan of Derek’s for a long time, and he doesn’t give a lot of interviews, so this is a special and rare moment. Don’t want you to miss any of it, so let’s get right into it.

Really excited today, because this is a momentous occasion. This is the first time we have another Derek on the show, spelled the same way so you know it’s the right way. Derek Sivers is the founder of CD Baby, he started that company and sold it for lots of money. He is a frequent speaker at TED conferences, there are some great ones that I have linked in the show notes. He’s done all kinds of things, he has the Wood Egg startup guides for southeast Asia, of which I read the one for Vietnam when I went there. He does some programming, he does a lot of reading and publishes his notes on the books he reads. He has written a best-selling book himself, Anything You Want. And we caught up in Wellington, New Zealand when I was there. There is lots more to say about him, but here is Derek Sivers. Welcome to the show.

Derek Sivers:

Thanks Derek.

Loudermilk:

Yeah, what a list of cool things that you’ve done. Another thing that I didn’t mention is that you write publicly on your website that you are an introvert and you don’t do a lot of interviews, so this is a fairly special rare unicorn to have you on the podcast. And one of the things you do is you have a lot of people, random people that you don’t know, that send you emails, just like I did several years ago. And that’s a pretty rare, I think. Why did you decide that that was the way that you wanted to be altruistic?

Sivers:

It seems like manners, to me. I wouldn’t feel good about being that kind of person that gets emails from people and just ignores them. Like, I can’t imagine doing that. But on the other hand I have good friends that have no problem doing that. It’s just a value system.

You know there is a business concept about the lifetime value of a customer. It’s not just about this one transaction, they might walk into your little five and dime shop and buy a candy bar today. You know what, if you are very nice to them and you provide a good environment and you’re friendly they might start doing more of their shopping and eventually all of their shopping at your corner store. So it’s not just about that one candy bar today. That person is worth more than just this candy bar, they can be a lifetime customer that ends up paying you thousands of dollars over years. So I think of that also in a non-monetary way that it may just be some random person I have no idea who this is, some stranger is asking a question, and I could choose to blow it off but instead by answering it develops a relationship, even if it’s just a loose, light touch relationship, we often never meet in person, it’s just an email, it’s just a couple of minutes of my time. But you never know what these relationships develop into over the course of many years. So I often think of the lifetime value of knowing someone, even a little bit. And it’s worth it to me.

So honestly, the main reason I do interviews like this, or even going and speaking onstage at conferences is for the people I meet one doing it, the people that reach out to me afterward saying “hey, I heard of you on the Art of Adventure podcast, I never heard of you before, I really love what you’re doing.” And that’s like a great way to meet somebody, you know? There is obviously plenty of people that listen to Art of Adventure that have never heard of me before venture. I love that.

Loudermilk:

Yeah. Here he is. This is Derek Sivers, everyone. Your hearing him? What are people asking you most commonly? Are there any big themes?

Sivers:

A lot of career questions, I think. Because people know that I sold my company and I often blog about entrepreneurship. I used to do some more in the past, I feel like right now I’ve said all I have to say. I don’t like talking outside of experience, you know, I like to only talk about things I’ve personally experienced. Not just spouting what other people should do without doing it myself, you know?

A few years ago I put out his book called Anything You Want, that was me trying to compress everything I learned in 10 years of starting, growing and then selling my company, trying to compress it into something you can read in under an hour. Like really succinct, you know? Of course I could go on for hours on the subject, but finding a way to compress it down into the most succinct delivery I could. So yeah, that’s my book called Anything You Want, that is out on Penguin Portfolio Publishing.

Loudermilk:

Just read that book. The interview is finished. Everything you need is in there.

Sivers:

Okay goodbye. No, but so I get a lot of questions about entrepreneurship from people that had read my book or articles. A lot of it is about how do you build your career or a lot of “I want to quit my job and follow my passion” kind of people or “I don’t know what my passion is”, it’s a real pet subject for people. Man I get people like, a guy in India asking me how he can deal with his frustrating parents or people asking me how to break up with their girlfriend or... I don’t know, it’s just kind of fun to open up my email box and put side like an hour a day to just…

Loudermilk:

You’d have a newspaper column if they were still newspapers. Well let’s talk a little bit about career building. You know, we talked a little bit about this and you were featured in Cal Newport’s book So Good They Can’t Ignore You and what are some of your thoughts about how to structure a career that leaves you happy and fulfilled?

Sivers:

Have you discussed that book on Art of Adventure before?

Loudermilk:

Yeah. Cal Newport was a guest, I can’t remember which episode at the moment, but yeah he came on and we did talk about that book. And probably mentioned that you are in it.

Sivers:

Such a fan of that book. I mean, yeah I read it because he... well actually no, first and foremost I’m a fan of Cal’s work, I have been for years. So pretty much anything he does I’ll just read because it’s Cal. So he interviewed me for something and he asked me a bunch of random questions when it was a very vague idea, so a year later when the book came out, I didn’t know I was in it. I just picked it up like “cool! Cal Newport has a new book” and I was reading it and suddenly: Chapter 9, Derek Sivers, I was like “wow, I’m in it!” So, that was a nice surprise.

But it’s not why I love that book, I really do think that that book is a game changer, it’s a wonderfully different way and a very rational and a very wise way of thinking about your career. And I highly recommend that anybody that is thinking of quitting your job or following your passion or anything like that, please go get and read the book So Good They Can’t Ignore You by Cal Newport. So I often direct people to that book for advice.

I’m not a consultant, you know? I’m not trying to be a know-it-all. I think there are some people that they want to appear smart so that companies will pay them lots of money to be a consultant, but I don’t do that, so I have no problem admitting that I’m not that smart. I often defer to sending people to the best advice I read. So if people are asking me questions I’ll say “you know that’s a really good question, you should read this book.” So for career stuff:

I think the big lesson from Cal Newport’s book So Good They Can’t Ignore You is to forget this idea of passion and purpose. People just take it like as a truism, it’s just a fact that you should follow your passion and find your true calling and “what is my purpose? What is the meaning of life, what is my purpose?” And his wonderful point after studying so many careers is that these emotions of feeling passionate or feeling you have a purpose is the result of you working and developing expertise and a path. The work has to come first. You can’t just like sit around, drinking your beers in Bali wondering what’s your purpose is. You’ve got to really pursue something and be working at something for years often, before you really feel the sense of like: I’m an expert in this now and the rewards are starting to come to me for being an expert in something and being valuable to the world. You’ve got to do the work first before it starts to feel like passion at work that’s giving you a sense of purpose. That’s a huge man, that changes everything.

Loudermilk:

Yeah, and there is kind of a pressure of having to know your passion. Because hundreds of people right now, probably in Bali, drinking beer and trying to figure out what is my passion and hoping for divine inspiration to strike.

Sivers:

Yeah. I think it’s actually a little bit of the downside of affluence, you know? Being able to afford to just sit around wondering what your purpose is. There is a really something to that work ethic. Go get a job, go get some job, any job! It doesn’t really matter what that job is. I mean, ideally it’s in a field that has some room to grow, but you can go get any job and career and just start focusing on it and learning all there is to learn about it. And develop valuable expertise and then that turns into a fascination.

This is beautiful quote: “the ocean gets deeper the more you go into it.” Any field that you are going into, the more you learn the more there is to learn, right?

This guy emailed me once, he was working at, I think a FedEx warehouse or maybe an Amazon warehouse, probably an Amazon warehouse, like in Virginia or something. And he’s just like “I hate my dumb job, I just work in the dumb warehouse shipping boxes for Amazon. I am miserable! What should I do?” And I was like “dude! You worked inside Amazon, that’s amazing! You should be studying the logistics system they use, like that is some cutting edge stuff that’s going on there. If I were you, I would take a minimum-wage job at Amazon in the warehouse just to start to learn how the system works and I would like to talk to my manager during the breaks and learn how they decide where things are going. How do the systems work? Look at the robotics they’re using. Like, God there is so much to learn there. It’s not just some dumb job.”

So to me, ever since I started working when I was 16 years old — the day I turned 16, the day that I was legally allowed to work, I got a job the first day I was allowed to work — I got a job in telemarketing because I wanted to learn how to get better at selling things. I spent a few years doing telemarketing. I think the people sitting next to me just thought of it as some stupid dumb job, but to me it was like “no man, I’m getting better at selling, I’m learning how to do this.” And soon I became the top salesman on the floor, we were like 200 reps on the floor, I was the youngest one and I became the top seller on the floor. Yeah, I did telemarketing for a few years until I felt that I kind of cracked that nut, then I took some other dumb minimum-wage jobs because they were the path to teaching me other things.

Loudermilk:

So there is an important distinction there, that this guy was thinking of this warehouse job as just something that he’s doing for money, but you’re saying is that these jobs are all intentional because there is something you want to learn. It’s like an apprenticeship somehow, and I think that’s maybe like a mindset distinction that people have, they are getting a lot more than just a paycheck, or you Derek, are getting more than just a paycheck, and other people are just trading the time that they wish that they could be relaxing for money instead of learning the system.

Sivers:

I have a core philosophy, that I’ve had ever since the that very first job, that you should never work for money. Money should never be the reason you’re doing anything. It always has to be secondary, there has to be a better reason than just money. So everything I’ve ever done has never been for the money. And money can be like a nice measure of success or a measure of achievement or even a measure that you are providing value to the world, you know? But it’s never the point. So no matter what dumb job I was doing it was always about building my skills.

But actually, that brings us into a bigger subject that would be fun to talk about: present focused versus future focused. There is a book called The Time Paradox by Philip Zimbardo that I highly recommend. In fact, if you go to my book notes page on my website, that’s sive.rs/book. I sort them with my top recommendations up top. And if you scroll like one page down, I think it’s probably like the fifth book listed as at The Time Paradox. And this book changed everything for me.

Because it starts out with the story of the four-year-olds and the marshmallow, and many of you have heard this, but just in case you haven’t it goes like this: a few decades ago they did some studies, some psychology professors at Stanford did some studies where they one by one they brought some four-year-olds into a room and they gave them one marshmallow, and they said “now I’m going to leave the room for a few minutes, if you don’t eat that marshmallow and if you can wait a few minutes I will give you two marshmallows when I come back. But if you need that marshmallow now then that’s the only one you get. So I’ll be right back in a few minutes.” And they had the hidden cameras rolling and they watched the kids. And they found that across the world, everywhere in different countries, Brazil, Japan, America, about 70% of the kids ate of the marshmallow right away. And across the world only 30% of those kids could wait the full, actually I think it was 15 minutes to get the second marshmallow. So yeah, those rates just stayed the same in every country. But here’s the interesting part: 15 years later those researchers followed up and they found that those kids that waited for the second marshmallow were now generally higher achievers. They were all around more successful, they were happier, I think they scored over an average like 250 points higher on the SAT test and they were just generally higher achievers in whatever field they had chosen, whether it was academic, athletic or artistic.

The point is delayed gratification. The ability to delay gratification is one of the best indicators of future success. And I love the marshmallow story. I heard that at a TED Talk and then I got to the guy’s book. And he elaborates much more on this idea of present focus versus future focus, being one of those things that, kind of like introversion and extraversion, that we all have our nature, it just comes to us naturally, but we can also influence it and change it. You can be painfully introverted or painfully shy and you can learn how to be a little more outgoing or appreciate the company of others more and vice versa, if you are one of those people that can’t stand being alone for single hour, you can find ways to learn how to be alone better. So with present focused and future focused, you can learn to change your focus of the world. But to me, it helped me understand all of these present focused people in the world, because honestly man, I’ve always been so off the chart future focused, everything I do is kind of like in service of my future self that I’ve never even understood why people seemed to like to go out to clubs and party. What is that for? How is that serving their future self? And this book actually helped me understand “ooh, they’re just being present focused, I never thought about that.” So, I think it’s the same thing. Sorry, we’re on a tangent about career paths.

Loudermilk:

Yeah, no. You’re saying that’s probably the majority of the people. I wish I had taken the marshmallow test now, because I have no idea whether I was that kid that could hold off on the marshmallow. Probably because I didn’t like marshmallows, so I would’ve been an easy...

Sivers:

It’d be tough if it was your favorite, you know, mint cookie… Yeah, anyway, so I think about this stuff all the time, I think ever since I read The Time Paradox it’s really helped me understand the world and understand other people and even in myself kind of questioning like: is this action that I’m taking, is this serving my future self or is is just some kind of immediate gratification need?

Loudermilk:

Let’s talk a little bit about your reading habits, because you read a lot of books. And I think you are one of the first entrepreneurs who I found their booklist. Well there is some other great ones: Gates Notes, Ryan holiday, Tai Lopez, they all have a lot of good book recommendations. And there is the idea, don’t know if it’s Charlie Munger who has the multiple frameworks of operation, he does a lot of reading. And I was wondering if in all the reading you’ve done, you’re starting to develop some grand theory of the way the world works or if you’re starting to pull interconnections between the different topics that you’re reading? Is there anything that’s been percolating in your mind about the world from all these books?

Sivers:

Absolutely! Thanks for a lovely segway into a thing that actually kind of currently fascinating me. My newest blog posts on my blog that I just posted a week or so ago, it’s at sive.rs/2do, it’s called “Just tell me what to do”: compressing knowledge into directives. Yeah, now I’m realizing that I’ve read and taken detailed notes on 225 books over the last seven years. And I review my notes often and, kind of initially in preparation for a conference talk I was giving, I thought it would be an interesting challenge to compress everything I’ve learned from all 225 books, not just into a summary of what I’ve learned, but how could we actually turn all of those observations into actions? That I think it’s a really useful thing to tell people what to do, you know? It’s hard to do, I think it feels weird to tell people what to do, because it feels like “who am I to tell people what to do?” But when I think about it...

Loudermilk:

It’s kind of what they want.

Sivers:

Well it’s very useful to others. So who am I not to tell people what to do, it feels like some kind of humbleness holding you back from being more useful to the world. Because a directive, if you remove some emotions around telling people what to do, like I’m nobody’s boss, all that kind of stuff, forget those emotions and just think of them as a useful sentence structure.

It’s called a directive when you say “do this”. Directives are a very useful sentence structure, because instead of just talking around the subject, if you say “do this”, they don’t have to obey obviously, they can choose to do it or not, but it kind of makes it a more digestible, palatable, useful format for communicating knowledge. You know like, the Ten Commandments, right? The Ten Commandments didn’t use up 25 stone tablets to discuss the various pros and cons and issues around the point, they just said “do this, don’t do that, don’t do this and do that.” It’s just a useful way of communicating an idea.

And I think the philosophy is actually contained inside the directive, right? So my favorite example of this is Michael Pollan, who wrote a book called The Omnivore’s Dilemma. And I’d heard good things about The Omnivore’s Dilemma for a few years, but I just never got around to reading it, because it was like it’s 450 pages and it got rightly entire history of food and everything that got us up to the current point. And I thought “uh, I’m just not that interested in the subject.” So a couple years later he wrote a book called In Defense of Food. And that one sounded a little bit more appealing, like now he kind of took everything from his big giant omnivore’s dilemma book and compressed it into only 250 pages. You know, a much tighter argument. But even then it’s like “uh, I’m not that interested in food”, and I really don’t even want to read 250 pages so I never got around to it. And then he put out a little tiny, tiny book called Food Rules, that you can read in like 30 minutes. Maybe 15 minutes. And it compresses everything he’s learned from all of his research into just 64 sentences. Each one is just a directive saying “do this.” Like for example it would say things like “eat only foods that will eventually rot” or “don’t eat food products that make health claims.” And I love that! Those are the beautiful little simple rules of thumb that you can use when you’re in the supermarket and you’re trying to decide what to buy: what should I eat, what should I do? You know? “Do this.” That is so much more useful to me than a big giant 450 page book that discusses all of the issues.

So yeah, I started thinking about all of these two hundred and twenty something books I’ve read and maybe it’s my chore, my job to compress everything I’ve learned from all of them into some simple do-this style directives for people. So that’s a project I’m working on now, I’m not sure what shape is going to take yet, it’s a brand new idea. It’ll just be something I do for the sake of it.

Loudermilk:

Can you share some of your favorite directives that you’ve come up with so far?

Sivers:

Yeah, give me a second. Okay, you want to hear some?

Loudermilk:

Yeah!

Sivers:

I’ll do two of them. I mean I’ll do two sets. I think part of the fun is to categorize them into certain how-tos. So instead of just a whole string of hundreds of directives, you group them together. So for example, here is one called how to get rich, okay?

How to get rich: Live where luck strikes

Live where everything is happening, where the money is flowing, where the careers are being made, where your role models live.

Once there be as in the game as anyone can be, be a right in the middle of everything.

How to get rich: Say yes to everything

Meet everyone, pursue every opportunity, nothing is too small, do it all.

Like lottery tickets, you never know which one will win, so the more the better. Follow up and keep in touch with everyone.

How to get rich: Learn the multiplying skills.

Speaking, writing, psychology, design, conversation, knowing a second language, persuasion, programming.

Each one of these could be pursued on their own, but really they are best as the skills that can multiply the success of your main pursuit.

So for example: an airline pilot who’s also a great writer and a public speaker.

Or a chef that has a mastery of psychology, persuasion and design.

Those people will be much more successful than their peers because they’ve learned these multiplying skills.

How to get rich: Pursue market value, not personal value.

Do what pays well.

Don’t be the starving artists working on things that have great personal value to you but little market value.

Follow the money, it tells you where you’re most valuable.

Don’t try to make a career out of everything you love, for example: sex.

How to get rich: shamelessly imitate success.

Imitate the best strategies of your competitors.

The market doesn’t care about your personal need to be unique.

It’s actually rather selfless and humble to just use the best ideas regardless of their source, so that you can create the best service or product for your clients.

Get creative executing other people’s ideas just as well as your own.

How to get rich: be the owner, not just the inventor.

It’s tempting to try to be the ideas person - to have someone else do the dirty work of making those ideas happen.

But ideas don’t make you rich. Great execution of ideas does.

It’s a rule of capitalism that whoever takes the most financial risk gets the most rewards. So the biggest rewards will always go to those that fund it and own it.

So to get rich you have to be the owner. As close to 100% as possible.

How to get rich: benefit from human nature.

Instead of complaining about the downside of human nature, just find the ways to benefit from it.

Instead of complaining about their rules, just learn the game and play it.

Loudermilk:

Wow! That’s amazing! There is so much is there. Each time you said something my mind was like “wow…” totally blown.

Sivers:

Right. Okay, so now I can confess that actually I spent four months in writing about a hundred directives like this, thinking that it was going to be my next conference talk. Like I got asked to do a big keynote speech at this big conference with like 2000 people, and it was going to be really high profile thing. I was like: I want to do something new and bold and daring. I’m going to compress everything I’ve learned in seven years into a 30 minute talk of directives.

And, dude, I spent four months of writing it and it sucked. When I was all done, it was like the day before the slides were due, and I was putting my final touch on it and I started to reading it out loud to some friends. I said “can I practice my talk on you?” They said “sure! Great, can’t wait to hear it!” And everybody told me it sucked. They were like “eh dude, no it’s really bad. You shouldn’t do it.” And I thought the first friend that told me that was just stupid. And then the second friend that I tried it on said that. And then I tried it on a different friend that I really know and trust his opinion, and he’s like “no, that’s a really bad talk. You’re trying to cram in too much. The first four minutes were fascinating and then it was just, you kept going and you kept going and you kept going and there was just too much there.”

I want to talk about each one of those issues. Getting the idea that trying to compress everything I’ve learned into 30 minutes is probably unwise. But maybe each one of these things needs to be its own article, its own blog post and then I can link them together as a simple list of do these things with more details if interested.

Loudermilk:

But there is, like you mentioned, the power and the beauty of the simple directive like in the Ten Commandments because as soon as you said the multiplication of the traits, that one jumped out to me. Because I was thinking about my friends who were the most interesting people to be around, and I was thinking about their personalities. And they have multiple intriguing personality traits. So that idea can actually be applied in other different areas and there is just a whole lot to think about there. You know they’re the ones with the addictive personalities that you are like “oh my gosh, you tell good stories and you are really good at strategy and you’re really caring. Like you have all these things all in one person.” You know, and they’re multiplying.

Sivers:

So the hardest part of this whole project is to take something that’s one of these big psychological studies that have been done and then one of these books will share their findings, and even they are compressing it down for the sake of making a book that’s readable by the laymen. They will take these very academic studies and compress it into a few pages of sharing the findings of these studies, but almost none of these books take that extra step of telling you what to do. It’s more like: here is our observations about the world so, good luck. Maybe you can put these to use somehow. I hope you enjoy our findings. So I like the idea of taking that extra step like saying: okay well, given this finding, this fact about how the way our minds work, how can I use that? Like what is the action that I can take or that everybody should take?

Loudermilk:

Books that had something that you just couldn’t figure out how to put into your directives.

Sivers:

Oh, all of them. Yeah. So what I really spent the last four months doing was just going through all of my notes, for all two hundred and twenty something books, and going to every single point that I had underlined. Every sentence, every paragraph and thinking how can I turn that sentence or that paragraph or that idea into a directive. So yeah, two thirds of them I just have no idea. But, you know, a third of them or so… I think it’ll just be an ongoing challenge for me, I could see these being something I work on for a few years. I really like it.

Loudermilk:

That’s really a valuable thing I think you’re doing. So I salute you for your effort on that. So many people are coming to you for advice, emailing you and now you have all these directives you are working on, you know a lot of things. But who do you turn to for inspiration or advice?

Sivers:

Well I’m going to sound like a total nerd repeating the same tune again, but generally books. Because I have this kind of introverted nature that… I really do enjoy one-on-one conversations, but in general I like the idea of trying to figure out things for myself. I’m not going to join a group or a mastermind of other entrepreneurs and have a whole bunch of people getting together to talk about things. I’d rather somebody would write up the conclusions afterwards and I can just read it. So I do turn to books for mentorship.

Actually it was kind of nice to see that James Altucher wrote somewhere he said “outsource 90% of your mentorship to books.” He said that a lot of people out there are trying to find a mentor: “will you be my mentor?” He said just let books be your mentor. Maybe I like that because it’s clearly what I have done my whole life. I almost never had a mentor. I didn’t just have one or two people. You know, Seth Godin was a bit of a mentor to me. I had one or two people that, just a little bit, helped at some key points. More like people that I could call when I was stumped. But for the most part I find books to be a wonderfully filtered, structured, well thought-through, well edited way of communicating an idea.

Loudermilk:

Yeah. And they are already sort of pre-compressed, all their experience, you know? Like you, seven years into one book.

Sivers:

Yeah, exactly! Yeah, I like that. And man, especially the bang for the buck. One of my dear friends is a real extravert, and books just don’t do it for her. She can’t just sit alone on the couch for nine hours and read a book, she falls asleep. But she loves seminars. So it’s so funny to me that she will go spend like $15,000 for some very high level mastermind seminar put on by this person that also wrote a $12 book. Everything they’re saying on stage was in their $12 book. And much more was in the book actually, that they can’t even get to on stage. But she’s happy to pay the $12,000 to go to the mastermind seminar because that’s just the way that she learns. That works for her more than a $12 book. But I’m thankful that $12 books do it for me.

Loudermilk:

So you’re saying let’s market to the extraverts.

Sivers:

Yeah exactly!

Loudermilk:

Because you know you’re an introvert you talk about it on your site, is there anything that you found to make you effective as an introvert that you’ve come to realize?

Sivers:

Good question! Sometimes your friends are very useful for things like this. When I was living in Singapore for two and a half years I’ve put myself very out there, I felt like, this is my new home, I want to meet everyone. I’m fascinated that we’re living Asia now, this is amazing. So I loudly put on my side “I live in Singapore!” And everybody that passed through Singapore knew that I was there, and everybody that came through for even just 24 hours on a layover would look me up and say let’s meet, and I’d say yes to everyone. And then of course all the Singaporeans that were there.

I ended up having like 500 or so one on one get-togethers. Just meeting in coffee shops for an hour or two, 500 times with 500 different people. And I would come home at the end of those days just exhausted. Say, like I’d meet three or four people in one day, you know, somebody at 10, somebody at noon, somebody at three, somebody at five. And then I’d come home at 7 PM and my girlfriend would say like “how was your day?” And I’d be like “ehhh...” And I said I met like four people and two of them were fascinating, and two of them were ehhh, you know, pick my brain. Is there anything that sounds less appealing than “I want to pick your brain”? Ugh! You know?

Loudermilk:

“Can I practice some dentistry on you real quick?”

Sivers:

Right! “Can I pick your root canals?”

So sometimes I would come home at the end of the night and she’d say “how was your day?” I’d be like “it was amazing! I was programming all day long. I got to my office at like 7:30 this morning and I just dove immediately into this postgreSQL thing I was doing and I figured out how to get to currency conversion to work with the JSON downloaded... Oh, it’s amazing! And I got this Ruby thing, I’ve been wanting to do this for years and I got this all working! Ah, what a day! I am like so pumped!”

And so finally she pointed out, she said “you know, all the days when you come home so psyched about what a great day you had, it was always those days where you just sat alone and were writing or programming all day long. The days that you come home and your most exhausted are always the days where you were just like meeting with people all day.” I was like “oh yeah.”

She said “why do you keep saying yes to these things if it exhausts you?” I went “that’s a very good question.”

And it was shortly after that that I moved to New Zealand, because I was actually just so immersed into Singapore, I was such a part of the scene there that it was just so hard to say no 50 times a week to everybody that wanted to meet with me or invite me to every event.

So moving to New Zealand was my way of kind of focusing inward. To me different places represent different things. You don’t always have to make one place your everything. So to me the New Zealand is my inward focused place and...

Loudermilk:

Yeah, because it’s hard to get to. I was like, I want to meet Derek Sivers, and I had to hop on a plane, fly really far away...

Sivers:

Yup! Not a lot of people passing through. But on the other hand not we’re not ever 100% one thing or the other, so I do go back to Singapore. I’m still a legal resident of Singapore and I’m glad that I am. And I would actually like to live there again someday, and kind of balance my time. Keep the home in Singapore and spend my time there when I’m feeling like being outwardly focused. Because sometimes those phases last for years even.

There was a time when I had like a couple of years that I was quite outwardly focused and loved it. Even my two and a half years that I lived in Singapore I really did love all that outward focus for about the first two years. And then my last few months that I felt like: I’m a little over it and I think I want to turn inward now, so that’s when I moved. So I think it’s okay to balance it.

So sorry, that was an answer to your question like how do I learn to work with my introvert tendencies. And I think you have to kind of boldly admit it. Even in Wellington, I’m living in Wellington, when you and I met I was living on the Wharf that was like right in the middle of the city, but now I’m leaving like off on the outskirts of the city, like right on the ocean looking at the big crashing waves coming in. I’m on the edge of town because I don’t like living near all the bars and the clubs and the people. I just like to be remote.

Loudermilk:

Cool. Yeah. It is useful. And feedback from other people can help us realize what we already know, but don’t have perspective on. I think if I recall when we were chatting you have residency, or maybe citizenship, in three countries: USA, Singapore, Belgium.

Sivers:

Yeah, New Zealand, Singapore and Belgium. To me Belgium is kind of my… or Europe in general is kind of my in between those two things. Like Singapore is total extrovert place, New Zealand is total introvert place and I found that Europe is kind of a nice balance for me where I’m very inherently, intrinsically interested in my surroundings, because I just don’t know Europe that well, I’m very curious about it. But on the other hand it’s a little more spacious there, it’s not super dense as Singapore. So it’s a kind of a nice balance, the way that I can be kind of inward focused sometimes, a few days a week, and outward focused a few days a week. So yeah, different places for different purposes.

Loudermilk:

So yeah, let’s talk a little bit about location and I’ve just come up with a thought experiment that I was ask you about. Because now we have digital nomads and people that can… You know, you left the States and we can all live wherever we want if we have a portable job. Let’s take that to the logical extreme. Can you imagine a world where everyone can teleport to anywhere. They can teleport to work, they can teleport to the grocery store, how would that change people’s behaviors and where they choose to live?

Sivers:

Well I think it’s funny that most people like being in the city, they love to be in a place with high entertainment value. Most people like to be entertained. I mean, most people watch TV, you know? They want the world to entertain them. So those of us that don’t, I don’t need entertainment, I don’t really have the need for cities that most people do. But I know that that’s a minority opinion, so I’m not going to project my own tastes and say that hey, if anybody could live anywhere then they would all live out in the beautiful rural countryside. No, the people have spoken, and they don’t want to live in that rural countryside. They want to live in the city where everything is happening.

I think there are different definitions to this digital nomad thing. I actually just went to a digital nomad conference in Berlin a month ago, and I was surprised to find that we had different definitions of this thing. So a lot of people are legal residents of America or Germany or wherever and they just want to kind of go backpacking around Southeast Asia, while doing some work on their laptop. And they want to go live that life in a hammock for a few years. But ultimately they see themselves as living wherever they’re from. You know, they talk about doing the digital nomad thing for a few years and then coming back or whatever.

But to me, I have a no interest in being somewhere for a short time, I really love moving to a place. Like everywhere I’ve lived, I’ve done than nine months of paperwork to become a legal resident of the place, you know? And plan on spending many many years there and even eventually getting citizenship if I can. That’s my definition of digital nomad. I love the fact that I can immerse myself into Singapore for a few years and immerse myself into New Zealand for a few years and Belgium and maybe even stay long-term or maybe I’ll just continue to have three homes around the world and spent four months in each and just keep moving like that.

But yeah, I don’t see myself ever going back to a place I’ve lived before. Like I certainly don’t want to live in the place that I’m from, that’s like the least ambitious thing I could do. I don’t want to live there, been there done that, I get America. Why would I go back?

Loudermilk:

Alright, cool. Well I guess some people, some digital nomads probably haven’t decided which they are yet. Kind of like me, I’m not sure.

Sivers:

Well you know, for experience. You might go hit the road and go spend a few months in Bali or spend six months in Thailand doing the visa runs every now and then and all that stuff and you may decide that you love that life. You may decide that you don’t.

Even Singapore. In Southeast Asia Singapore is kind of unique in how crazy expensive it is and how clean and developed in this. But what I loved about Singapore is that you could become a local. Singapore has always been a melting pot of influences and the British have been there since the beginning, they were the founders of Singapore. There was basically nobody there before the British came in and made it this thing. So it’s always had a white people as a minority, but still just as local as anyone that have lived there for many generations. I like the fact that I was completely accepted as a local in Singapore and part of the scene, even if I didn’t grow up there. Whereas, I imagine that if you’re in a place like Japan or Thailand or Indonesia, you’re never really like fully integrated. You’re always kind of the outsider. I kind of like that about Singapore, that you really could really make it your long-term home. My son was born there. He’s born in Singapore and he’s proud of it. So even here in New Zealand, he’s three years old, but he’ll tell anybody that listens that he’s like “I was born in Singapore! I’m from Singapore!” And I love that fact that that’s part of his identity. In fact it’s funny, both he and I are permanent residents of Singapore which means that, unless something changes, he will have to do two years of military duty in the year 2030 for the Singapore military. I’m into that kind of immersion, you know? Not just breezing through and drinking some beers and moving on, but I love to get immersed into a place.

Loudermilk:

Well and beers in Singapore are so expensive, why bother? I want to shift gears real quick and ask you, because you are well known for CD Baby and you were a performer for a long time and that’s probably what led you into helping so many other artists produce their work. And since you’ve already written a book about this and you’ve talked at length about it, I wanted just to ask you if there was a big shift in your thinking from who you were as a performer to who you were as a CEO, business owner, someone who has sold a large business. How do you view the world differently after going through CD Baby?

Sivers:

I never viewed myself as a CEO of a large business. In fact I think that that was the root of the lot of misunderstandings and how I was running my company, I was still treating it kind of like an art project or kind of like a band.

For example: if you have the band, if you are the songwriter of the band, nobody ever tells you like “hey man, you should outsource your songwriting to somebody else, have somebody else write your songs.” Because no, it’s clear, this is your creative outlet. Why would I have somebody else write the songs for my band, right? But as the sole computer programmer of CD Baby people would often say “hey, why don’t you just hire some programmers?” And to me that was the same thing, I would never do that.

This is my creative outlet, this is my venue for self experimentation or self-improvement. Why would I have somebody else do it? That’s silly. It’s like running a marathon saying “hey, why don’t you just call a taxi to take you to the end?” It’s all about the journey.

Loudermilk:

Some people would be like “great idea!”

Sivers:

Yeah, exactly! The Tim Ferriss shortcut. “Hey, here is a hot tip: here is how to run a marathon in three minutes. The 3-minute marathon: call a taxi.”

So I never really saw myself as that big business CEO. And that was a source of frustration for people that were trying to deal with me or wondering why I was making the decisions I was making. It seemed like I was a quirky oddball, but it’s just because I never really considered it to be a business, that’s not why I was doing it. It was just helping some musician friends and doing it as a creative experimentation for myself. So no, I don’t see that much difference.

I think the main difference, or maybe the only difference is that from the age of 14 to 29, everything I was doing was me me me me me. It was like MY music, MY thoughts, MY songs, out there promoting myself. It was all about me. And when I was 29, that’s when I started at CD Baby and I guess because I had spent 15 years in me-me-me-mode, I was ready to switch. So CD Baby was not about me. It was all about helping my musician friends. It was them them them.

Which is funny that people that knew me as a musician would ask “hey man, so you are still making music?” And I would say “no.” Like, something switched in me. Like, it’s not about me anymore. Maybe it’s a little bit like the former athlete that is now a coach. It’s like that athlete had his day in the spotlight and now he’s a really ready for his players to take the spotlight. And I felt like that with CD Baby. That was just like I’ve had my time in the sun and my time in the spotlight, whatever you want to call it, and now it’s my time to help everybody else have some of the success that I had. Or more. That was a difference in mindset, but definitely not like a CEO business kind of thing, I never adopted that mindset or that self-image.

Loudermilk:

Gotcha. Yeah and thanks for this sports analogy, that really helps people like me. Okay Derek, I got two questions that I ask all my guests. The first one is, if you could change or add anything to the world, what would you want the world to have?

Sivers:

More peanut butter. Easier access to peanut butter from all around the world.

Loudermilk:

I’m right there with you. Love peanut butter. Alright! Second question is what’s your definition of adventure?

Sivers:

I think it has to stretch your self-image. I really like those moments in life where you have the previous prejudice, something that you used to think that you hated. Something that you thought you would never do, like you have this self-image of like “I am this kind of person, this is who I am. I am not that kind of person.” And I love when you change that.

To me the adventure is changing who you are. In the classic definition of an adventure it doesn’t count as an adventure if the hero goes out into the world and comes back exactly the same. You know, the way that stories are written is the hero is changed somehow in this adventure.

So the definition of adventure to me is the things that change who you are. Even tiny little examples like: so you’re in Bali right now, right? So when I first started CD Baby I was in New York and almost right away, like only one year into it, I started getting some big orders from Indonesia. I was like “whoa, that’s amazing!” People would come through and buy like $200 worth of CDs. And I’d be shipping them off to Jakarta. I was like “wow, who knew that there was like such a market for indie music in Jakarta, Indonesia? How cool!” And then I would get one of these big orders every week. Hundreds of dollars of CDs, ship them all off, even though the postage cost a lot, and after about two months I got contacted from the credit card company saying those are all fraudulent orders. So we’re taking the money back from those. I don’t know if everybody knows, but that’s how it works by the way, whenever there is like fraudulent activity on the credit card it’s the store owner that gets screwed. The credit card owner is protected, they’ve got their insurance on their Visa card. Visa and MasterCard sure aren’t gonna take any loss. No, it’s the store owner that gets screwed. So yeah, I got to really screwed by people in Indonesia over and over and over again. To the point where I was just like “Indonesia, it’s an nation of criminals. I hate those people!” And I ended up blocking Indonesia completely from the cdbaby.com website. Actually it to let you visit, but it wouldn’t let you complete any order. So all those thieves in Indonesia would think that they were getting away with some credit card fraud, it’s just that the order would never arrive and I would never charge the card. I would just destroy the order silently without…

Loudermilk:

They’re just wasting their time.

Sivers:

Yes exactly. Okay so here’s the punchline. So now it’s six, seven years later. I’m living in Singapore and some guys in Indonesia invite me to speak at TEDxJakarta. Attending it changed my life. Oh man, it was the most wonderful outpouring of Indonesian pride. Those speakers at TEDx Jakarta were doing amazing work. I was like tears in my eyes with like the amazing people doing amazing things. And even the whole staff and the people that were putting it on, everybody was just so cool! And so amazing and so brilliant. I wanted to be Indonesian that day, I was like “I love this country! I love these people!” And so ever since then I’ve been a big fan of Indonesia and I’ve gone back many times since and I’ve got involved with some universities there.

And then suddenly I remembered, like I had actually completely forgotten, it’s like: oh yeah, I used to hate this country. I used to have such prejudice. I used to think it was a nation of thieves. I guess I’ve really changed and opened my mind.

And more recently, just two years ago, with weightlifting. Because I used to go to a high school where you were sharply divided between the jocks and the freaks, you know? So there were the jocks and then there were the freaks, the people with the denim jackets with Judas Priest and Iron Maiden patches and hanging out in the smoking area with their Corvettes, you know? So I was clearly in the freaks category. Long hair, heavy metal patches, hanging out in the smoking area back when high schools actually had a smoking area. That was allowed, those were the days. So I was anti-jock, right? The jocks were the enemies.

So even up until two years ago I would actively make fun of people that spend time lifting weights. I’m like “what a stupid thing to do with your life, to spend your life lifting pieces of metal up and down. What a ridiculous stupid vanity thing to do!”

But two years ago a couple of different people that I know and respect showed me that the weightlifting is not about vanity or getting big, in fact to weightlifting and bodybuilding are two very different things, and you don’t have to look like one of those big lunkheads. In fact weightlifting is one of the best things that you can do for your skeletal system, it’s just good for your overall health and all that. And I thought “okay, I’m ready to change my mind about this.” And so I tried it, and I love it! It turns out I’m good at it and I really enjoyed doing it. So yeah, for the last two years I’ve been doing weightlifting and loving it. And I think that wow, I really changed my mind about that, that’s a really cool feeling.

Long answer to a short question. I think that’s the definition of adventure, is going out and changing your mind and changing who you are on a subject.

Loudermilk:

Those are great stories and I think that’s a special trait to be willing to change your mind and embrace it when it happens. So I salute you for that. And of course, I salute you for all the great work that you do and all the thought that you’ve put in the writing that you put out there on the things you say. Conferences and stuff like that. All of us appreciate it so thank you.

Sivers:

Thanks! You know, like I said earlier, the reason I do interviews like this is I think it’s kind of cool to meet people that are the kind of people that listen to Art of Adventure. So if you’ve made it this far to the end, please send me an email. And feel free to ask me anything, I answer every single email I get. I enjoy the challenge. Or just say hello.

Loudermilk:

Is there anything you’d like to point people towards, where they can find out more about you?

Sivers:

Just my website sive.rs. It’s all free, there are no ads. It’s not commercial, in fact for those of you that are into this kind of thing, even if you view source, you’ll see that I don’t even do any Google Analytics tracking, there are no cookies, it is just totally non-commercial static free site that I just enjoyed doing to share my thoughts. So yeah, hit sive.rs and that has everything.

Loudermilk:

Perfect. Boom. Well Derek, thank you so much for coming on the show, I really appreciate you.

Sivers:

Yeah, thanks for having me!

Loudermilk:

My pleasure. We will talk soon.

Sivers:

Okay. See you!

Loudermilk:

Bye!

Hope you guys enjoyed that episode with Derek Sivers. I am not just a big fan because he has the same name as me, but I feel that I can just sit and listen to him talk for hours. He is one of the greatest thinkers of our day. You know, he is in a great position to do it, he says he doesn’t like to talk about anything that he doesn’t have experience with. Well luckily he has a lot of experience. I hope you think about some of those directives that he shared with us about getting rich. I have some links to another one of the talks he gave about some of those directives. Check out his website, there is a lot of great articles, straightforward simple thoughts on there. You know, I first got in touch with him by sending him an email. He offered the same for listeners of the Art of Adventure. If you like, if there is something that you think he is the man that can answer this question, give him an email. He’s a great guy. I am just, again, so thrilled to have him on the show. I really appreciate all his work. So if you like this interview, if this is the first time you listen to the Art of Adventure or if you’ve been listening for a while now and you’re not subscribed, I’d love it if you would subscribe on iTunes or Stitcher. And if you’re so moved, leave a review and let me know what you think of the show and what you thought of this interview in particular. If you have any questions for me or the other Derek you can leave them there, you can send me an email at derek@derekloudermilk.com. It’s been a pleasure talking to you guys today. Now go out there and be adventurous!