Derek Sivers: Deliberate Change for Deliberate Happiness

February 7, 2012

It doesn’t get more real than breaking it down with Derek Sivers. In his Fear.less story, Dereks talks about fear, finding passion, and pushing himself out of his comfort zone to get even happier – and he’s already a pretty happy guy. I enjoy talking to Derek because of his ease and approach to life, but also because despite his enormous success, he’s a friend who digs out your own gifts and reveals them to you; He’s not all “Look how shiny I am, follow me,” (and he could be from his bio) but makes you think about why you make the choices you do. He also walks his talk: Derek’s crossed more new territory in the last year than most people do in a decade: moved to Singapore, gotten married, wrote a best-selling book, learned a new programming language. And yes, he’s done it all in the same 24hr/365 day cycle we all have.


When people speak of passion, they're usually expecting a big lightning bolt of inspiration. They’ll tell you, I haven't found my passion. I don't know what my passion is. But if you take a closer look, they're already playing video games five hours a day or playing with their kid every night or riding their bike or playing basketball each week. The things you love doing, when time seems to fly, that s your passion. You don't need to wait for a big lightning bolt: There s no such bolt!


Ever since I was 14, I knew all I wanted to do was play music. It was the same way that someone says, All I want to do is play basketball. Maybe I was just a confident little kid with rock stars as role models- I was determined that through hard work, I could find a way to make a living doing this thing that others call play. I knew that there was this life, whether it meant I would be a music teacher or something related, where life was play. And then I went off to music school. I heard about a dozen other careers I could go into: film, TV, music scoring, producing, or opening a recording studio to make music for a living.

That was my first experience following my passion. I got tuned into noticing what was capturing my interest. There was a time in the mid-nineties where I had already been a professional musician for about ten years when all of a sudden, I found out how fun it was to make my own website. It was the early days of the net in 1994, and I was making my own HTML website. Somebody gave me a bootlegged copy of Photoshop and I got the Photoshop 3 for Dummies. I stayed up all night, all weekend learning how to program. For some reason, Photoshop was a blast for me and that was what was capturing my attention. So for a few years I was both touring as a professional musician and creating my websites. I realized, This is keeping me up all night! That s actually how CD Baby was born. It really started to take off.

I think it's important to take notice of what fascinates you. I think you ve got to pay attention, even notice what books or articles you like to read a lot. If you find yourself fascinated with articles about religion, then maybe you re really into the topic of religion and maybe you should just admit it. Or maybe you re fascinated with pieces about agriculture. I say dive into it if it interests you. Take notes and dive in further.


Stephen Covey, in his book 7 Habits of Highly Effective People, speaks about how you can find the fine line between what s important and what s urgent. So many people take up things that have a sense of urgency; somebody comes by your desk, interrupts you, calls you or knocks at your door. You think this is urgent, but it's not important – There s a difference.

Important is doing the work that will make the biggest difference in your life or the life of others. Little distractions have a sense of urgency, but they're not important. We tend to place other people s requests as urgent and therefore give them more importance, when actually taking care of our own self, our destiny, our passion is much more important. it's a really hard lesson to learn.


The reason I've been thinking about it a lot lately is I just moved to Singapore, which is a major cosmopolitan city with people from all over the world. Word just got out that I moved here and I swear I'mgetting five emails a day, and I'mnot exaggerating, from people who say, Hey, I'd love to take you to coffee. I really want to pick your brain. I'mstarting X and I'mwondering if I can get your feedback on what I want to do and I'd just love to meet up sometime. Let s hang out.

For the first few months, it was appealing. I thought, OK, this is my new home. I want to get to know my community. And it was good for the first three months. Then I kept doing it for a few more months, even though it was really one-sided. Every day, I came home after four back-to-back meetings. My wife, who is an educational writer, would be sitting at home writing because people didn't want to pick her brain. She would get lots of work done whereas I would come home and look at her with jealousy.

I'mso jealous that you got to work all day. All I did was talk all day long. I've chatted over coffee all day, every day for the last three weeks.

She d ask, Babe, but why are you doing this ?

Because people keep asking, I'd say.

Finally I had to find the will power to say no. I ended up writing a really well-written form letter and now five times a day I send it out in reply to the incoming requests.

Saying no is hard work. Not a single day goes by when I'mnot practicing diplomacy, and emails are a great way to do it. When you re talking to someone in person and they say something rude and you say nothing, but three minutes later you walk out swearing, I should have said this! and I should have said that?! With email you can catch yourself in those moments and avoid regretting it later. So every day with the emails that show up in my inbox, I've found a way to practice diplomacy. A while back, I got a very long email from the head of a book publishing company I really admire, telling me that he read my book, how everything was wrong with it, and how companies like The Domino Project were ruining the quality of books. Of course my first reaction was to somehow defend myself and correct all of his wrong assumptions. And I even started to but then stopped midway. I went back, erased it all and started over with, Thanks so much for your message. I'mhonored that you took the time to write all of this and appreciate the feedback. I really appreciate what you re doing and I love your company.

And that was it. I was like, OK. Diplomacy: check!

I taught diplomacy to my whole customer service staff at CD Baby. You know what the great metaphor for customer service is? If you ve ever stayed at a really nice hotel, the people at the front desk are always wonderful, no matter what. You could come in and throw up on their counter and shout obscenities at them and they would say, Oh, thank you sir. Right away, we will make sure to get someone to clean that up. If we can help you in any way let us know.

I would try to teach my customer service staff to imitate those people at the hotel. No matter what bile somebody s throwing into your face, just thank them for it and ask if there s any other way you can help!


During the last few years of CD Baby, once I had delegated away everything, my life was the same as it is now, which is pretty sweet: I wake up every day and do whatever I want.

Earlier, I'd have the pressures of employees and customers and each day a lot of things would get thrown my way. I had 85 employees and wherever they weren't happy, it became my fault. I'mglad that s over. So my life has less pressure now.

They say that everybody s got their amount but there s a point when you have something they call F U money, when you don't have to please anyone ever again. It feels nice that I'mup to that point because I don't have a company anymore and I can just say, No to anyone I want to. I don't have to worry about repercussions to the health of my company. Not having to worry about a company is awfully nice. But that s it. And here I am about to start a new company now, so we ll see how I'mable to balance that.

Everybody has their own measure for balance. My wife, for example, loves her work, but she loves to do it for eight hours and then stop. I love my work too, but I love to do it 16 hours and then stop. I've found what I love in life, so I get a little sad when it's time to turn off the computer and stop working to watch a movie or have dinner. I ll say, Well, I could do that I guess. But I'd much rather be figuring out my next Ruby on Rails problem or programming something – this is my sandbox – what I love to do.

I don't think there s one answer for everybody. Everybody has to find their own balance. Instead of trying to do what other people say, just pay attention to your own balance and what makes you happy and honor it. So if you enjoy working 16 hours a day, of course there s always going to be someone telling you you re wrong. But just go for it anyway. And if you prefer working eight hours a day or four hours a week, then of course, again there s always going to be someone to tell you you re wrong. But you need to honor your own preferences and do it the way you like.


The term happiness is vague. But we all know what it means. I've noticed that a lot of this comes from a place that once you are personally happy with what you have in life, it really can change your focus. So if you re truly happy, you don't need to push so hard to make money and you don't lust after a Lamborghini.

I'minnately happy. I guess it's what we said at the beginning about noticing what fascinates you and to honor that. To pay attention to what drains your energy. If something s draining you, stop doing it. If something s fascinating you, keep doing it. I've also always been pretty non-conformist. So I'mnot really affected by other people s expectations of me. I've always tried to pay close attention to my own, personal tastes and that keeps me even happier.

I don't know if it's just my natural decision or something, but I think I got to that happy level very early on. Perhaps even before starting CD Baby. I was living the happy life as a pretty successful professional musician already. I was pleased with myself. So everything I did with CD Baby just felt like giving back. It was my favor to the world. I wasn't lusting after riches or something else. I think that really helps because there are some people who even if they have a hundred million dollars are not happy. They need to get five hundred million because they just have a different set point or something.


In 2007, I started reading two books back to back. One was Stumbling on Happiness by Daniel Gilbert and The Paradox of Choice by Barry Schwartz and there was some overlap between them. But Stumbling on Happiness, especially, it was an interesting read about a Harvard psychology professor who had done a multi-year long study on the subject of happiness, sharing objective findings with tests run on hundreds of people. The book had these findings, averaged across all people. I took a lot in those books to heart. And there are some things that I'mdoing in my life now – actively making changes in my life based upon the advice of my elders.

I might have just been comfortable in my California apartment on the beach in Santa Monica, carrying on with my habits, riding my bike on the beach and doing my thing in my comfort zone. But reading these books taught me that I would be happier if I kept myself out of my comfort zone and kept growing. So I moved to Singapore deliberately – I moved across the world because it scared me. I have a motto where you go and do whatever scares you. And whatever excites you, you go do that.

If you chase what makes you feel great, you usually think of that saying, I feel so alive. it's usually hand in hand with fear. Isn't it? Somebody says they feel so alive when they're jumping off cliffs or sailing with sharks or whatever it may be. They say, I felt so alive! Well, I think whatever makes you feel so alive is usually hand in hand with what scares the hell out of you and that s what you should be doing.

So, yes, I've had to make some very deliberate changes in my life. I was scared to get married. I got married. I was scared to abandon my comfortable country and move to a strange place all the way across the world. I moved. I was scared to sell my company, let go of my identity as Derek at CD Baby but I did. it's constantly pushing yourself out of the flow, not just going with the flow. In fact there s a great saying, Only dead fish go with the flow.

Sometimes you need to make these deliberate changes in life, based on the advice of people who ve been there, done that, whether it's a Harvard psychology professor sharing findings on happiness or somebody who s a real role model to you, whether it's Seth Godin or a Charlie Munger, and honoring these people s advice, gained from decades of experience.


Once it becomes your comfort zone, you tend to adopt it. You say, Ok, this is now my identity. This is my thing. This is something I know how to do.

Here s what s funny about me. I have the opposite fear that most people have it's the fear of not being on stage. I have extreme stage comfort because for 12 years I made my fulltime living performing. I've done over a thousand shows on stage and that s what I know how to do. I know how to get on stage and entertain people. What I don't know is to sit in the audience and not be on stage. That makes me feel uncomfortable and weird, so any time I'msitting in the audience, I'malways a little bit uneasy. But put me on stage and I m, Ah, yes, this is my comfort zone!

Yet again, it's tough to keep your spirits up, honestly, when you re constantly beating your head against the wall. You feel, Oh, God, it's tough. For me, it was submitting your music to try and get picked to do a showcase at South by Southwest or impress a booking agent or a record label. You re constantly sending your music to people who reject it and it gets really stick to it and not let it bother you too much. I think it's the hardest thing.


I've been learning and doing all kinds of new things like moving across the world, but I'mstill also in my comfort zone because I'mbeholden to no one, as an independent guy. I just read, write, and blog but I'mnot responsible to anybody. Nobody s paying me to do something. I'mabout to put my ass on the line again with my new company, so we ll see how that goes. But the hardest thing for me, my fear right now is programming in a new language and programming things I've never done before.

So, the way it really goes is this: First you build up this pressure that you ve been wanting to do something and haven't done it the pressure of procrastination. Then it gets almost physically painful and the best way I can describe it is that feeling we all know where you just think, Shit, Shit. Shit. Ok. I HAVE to do this. Shit! And then you say, Err, OK, damn it, I do not want to do it. OK. All right. I've got to do this. I've got to do this. OK, all right, I'mturning off my phone. I'mpulling the Ethernet cable out the back of my computer. I'mdoing this now. Shit!

And it's that horrible feeling of facing something that you know you want to do, you re scared to do, and you have to do it. You know you re going to hate yourself more if you don't do it. You can't live another day with that pressure of procrastination. The funny thing is that once you sit down and start doing it, you realize it's hard at first and we all know that feeling, whether it's fifteen minutes or an hour into it, but all of a sudden you don't find it that bad. Slowly, you re into it. Cool, I'mgetting work done. Woo hoo!”

it's just funny how long you can let that pressure build up before you do something about it. And even as I talk about this I'msuch a hypocrite right now. I announced Muckwork, my next company, three years ago, and I worked on it for a couple months and then it got hard and I decided to do other things for a while. And then I took this three-year sabbatical that at first I thought it was going to be a few months and then it became a year and then it became two years and now we're coming up on three years. And everyday I think to myself, OK, it's been three years. I've got to do this thing. I've got to make this happen.

I often think of this as a brain exercise where you think about What if you realized that you only had fifteen minutes left to live, and your plane is crashing? What if, in that moment, you have no more chance to fix anything or call someone and tell them something? it's done. What would you regret in that moment the most? That goes in your bucket list. Stop whatever you re doing and do those things first. You need to die happy. So, work on those things.

If I were to jump off this fifty-first floor of my building right now, on the way down I would be thinking, Shit, I didn't make Muckwork! it's actually a deathbed regret for me now. So, now I realize that I just have to do this FIRST before I spend hours letting someone pick my brain over coffee.