Interviews → Unmistakable Creative

Srini:

I’m Srini Rao and this is the Unmistakable Creative Podcast where you get a window into the stories and insights of the most innovative and creative minds that started movements, built thriving businesses, written bestselling books and created insanely interesting art. For more, check out our 500-episode archive at unmistakablecreative.com

In this episode of the Unmistakable Creative Musician, programmer, author and CD Baby founder Derek Sivers joins us to talk about creating a life that enables you to get anything you want.

Derek, welcome to the Unmistakable Creative. Thanks so much for taking the time to join us.

Derek:

Thanks Srini.

Srini:

It is my absolute pleasure to have you here because you’ve been long requested by many of our listeners and fans of the show just because I know the work that you do has impacted their lives in some way or another either through your TED talks, your books or even through CD Baby. And you’ve done all these sort of really iconic things like founding CD Baby and selling it for $100 million, writing these amazing books and having this multi-hyphenate career. I want to start out talking about what the formative experiences of your life have been and inflection points that have ultimately led to everything that you’re up to and all of these things that you ended up doing.

Derek:

That’s a hell of a first date question, huh? Let’s see. I moved every year. I think that was a big thing. Now that I have a kid, I’ve heard other people say, well, you know, kids need stability.

Srini:

I’m one of those kids who moved every couple of years.

Derek:

Oh cool. Maybe you get this then. To me, moving every year was my normal. That was just the thing to do. We just moved every year. And I remember this moment, I still can vividly picture this, when I was 6 years old, we moved to Chicago. I remember asking my mom ‘How long are we going to stay here?’ And she said ‘Maybe 5 years, maybe even 10 years.’ My lips started quivering. I went “whaaaaa!!!”. The idea of staying in one place for 5 years. Oh my God. That was a horrible thought. It’s kind of funny. We did end up living there for 10 years.

But sure enough, as soon as I was able to get free, as soon as I graduated high school, I was off to Boston for a few years, New York for a few years, and have just been bouncing around ever since. I haven’t lived anywhere for more than a couple of years since then. So that’s physical location wise. And actually just very recently somebody told me that’s a very American thing to do. They said, you know, Americans often deal with their problems by moving. And that’s just a side effect of this big giant country where you’re allowed to move anywhere. And a lot of people that settled there came from other places and they moved to be there.

Like my friend, Anna, who lives in this house in Padua, Italy that her family has owned since the 1600s. It’s just a different mindset.

But anyway, so, yeah, I move around a lot and that applies career-wise too. There’s this feeling of been there, done that. I read a quote from an artist, a painter who said something like ‘I like to do something until I know how to do it.’ And then I stop. I think that applies to things that I do.

Srini:

How did the experience of moving around so much impact the social relationships in your life and the way that you run and build companies and meet people and interact with people?

Derek:

The way that I interact with people, I’ve found that ever since I left my high school, when I graduated high school and moved off to Boston, I kept in touch with friends by phone. And really I think in high school, I did the classic high school thing of talking to my friends for hours a night on the telephone. And I still do that. Like, right now my two best friends are in Portland, Oregon and New York City and I’m in Wellington, New Zealand and, actually, there’s a third one in Sweden. Actually my three best friends. So yeah, Portland, Oregon; New York City; and Sweden. And we talk every day on the phone, or every other day. I think that’s just very normal to me. I think other people have this definition of friendship as friends are the people you go hang out with and you go and do things with. And if you were to move from your town, you’d lose those friendships because you’re not hanging out anymore. So I guess I’ve always been a remote friend.

As far as companies, this is kind of new to me. CD Baby I set up, it was a pay pack-and-ship warehouse business. It was very much based in a place, though I was kind of uncomfortable with that. So about 4 or 5 years into it, I made sure that it was autonomous. That it could just run without me. And then I went down to Los Angeles to be with my girlfriend while the company was up in Portland, Oregon, and I just ran it remote. And I guess I did that for the rest of the company’s history. I like working alone. I like being somewhere else from where everything else is.

Srini:

That’s interesting. You like working alone, yet you’ve done these really big things that involve other people. And I’m just interested in how that works. How the dynamic of that actually plays out. And how other people deal with similar situations. Like, I thrive entirely off of being around other people and that’s largely why I think I’ve chosen this as a platform.

Derek:

I don’t mind being in touch with people. So, like, my email Inbox. I put aside time every day. I get probably 30 or 40 emails a day and I answer every single one and I put aside some time to do that. Like my girlfriend, for example, thinks that I’m crazy social. But she’s a professor and she’s a real introvert.

I’m definitely an introvert. I like to physically be alone. If I’m in a room by myself, I feel that I have unlimited energy. I can just go forever. And then if there is just one other person in that room, it just drains all my energy away. I’m just tired within half a hour. Even if I’m not talking to that person. Even if that person is just on the other side of a big room. Just having another person around drains me. I just love total solitude for work like that.

But say for example my Wood Egg book publishing company that I did a couple of years ago, I had something like a total of 130 people working to make those books. It was a series of 16 books. Each one had three researchers, a couple of writers and an editor. And I just never met any of them in person. It was all just remote and I systemized the thing, so it was kind of like a little bookmaking factory. I slotted people in, I found people and put them into the slots, people that wanted to do it, and if anybody had to flake off or take off or change their mind, it was no big deal to slot somebody else in. And I’m really comfortable with those kinds of situations. I think that’s the hybrid for me. A way of working with other people, but yet physically being alone.

Srini:

So you’ve done all these things. I guess one of the bigger questions that comes from this for me as I’m thinking about all the people I’ve spoken with and wrestling with a chapter I’m writing in the book around mastery, like, how people become masters, you’ve had this sort of multi-hyphenate career and I’m just curious. How do you know when you’re reached a point where it’s time to move on to something else? And do you think that everybody is destined to have a multi-hyphenate body of work? Or are there some people who are just destined to be masters at one thing in particular?

Derek:

That’s kind of a trick question.

Srini:

I’ve been known to do that to people.

Derek:

It’s not about destined to be. It’s about, let me think for a second. Sometimes it depends just how broadly or narrowly you are defining what you’re doing. So to me, writing songs, writing copy, as you could call it, writing my site, all the communication, writing my essays, writing the blog posts on my site and writing computer code. Those things all feel pretty similar to me. It’s all just creative expression. Actually I think writing songs is kind of a hybrid between the two. So maybe I could see why those two things grew out of it.

So imagine this. When you’re writing a song, especially a song with lyrics, then your lyrics are successful based on how well they are received. If you write some lyrics and nobody has any idea what you’re talking about or they completely misunderstand you or they just generally don’t like the lyrics, then you’ve failed at those lyrics. Unless your only mission was just to scratch your own itch and you didn’t care about anybody hearing it. But for the most part, your lyrics are successful if people get it and they like it. So I think it’s the same thing with writing essays or copywriting the text on your website or writing articles or writing a book even. It’s all about how well you are understood. You have your thoughts in your head and you’re trying to get them into someone else’s head. So if you do that well, you’ve succeeded.

But then the other half of music is the music itself, sort of putting this all together and taking this sound or this idea in your head of this music or this song you want to write and having to go through some skittles to make it happen, whether it’s finger dexterity on an instrument or recording studio dexterity to make the sounds you want to make, that to me feels like of like programming. I have this idea in my head about a website or some app that I want to exist and now I’ve got to type the right code and wrestle with it and figure out how to turn that idea in my head into reality.

So everything I’m doing to me feels like one big thing. It doesn’t feel so multi-hyphenated until someone is asking me. Like if I do a blurb on the back of a book cover and somebody is saying, ‘How do you want to be credited?’ I’m, like, oh, I don’t know. Just say Derek Sivers. Do you know what I mean? It all feels like one big thing.

Srini:

Yeah, I do. My work has taken on a number of different forms in the form of producing events, products, books and producing this podcast, although the podcast is sort of the primary one. But it seemed like it had all these sort of extensions that I never planned or predicted.

Derek:

Right. Now imagine this. Different people have different reasons for what they’re doing. Some people may start a company because they want to make a lot of money. And that’s their main goal with that company, just make as much money as I can. That’s why I’m doing it. Other people, their goal may be to leave a legacy. I want to do this company. Say it would be a classic Silicon Valley thing of measuring your impact on the world. I want to change the world. I want to have a big impact on the world. And that’s how they would measure the success of their project.

But someone else, and this is my example, may do things just for the doing, just for the curiosity of seeing if this is something you can do. It’s more of a personal development reason for doing it. Like, I want to see if I can start a book publishing company. Or I want to see if I can make this little idea happen or I want to see if I can learn a new programming language and do all of the programming myself without asking for any help. That may be the personal challenge.

And that’s what I was actually doing with CD Baby and even with Wood Egg. Both of those things were just scratching a personal itch. That was just something that I wanted to see if I could do. It was like a little puzzle I wanted to solve. And so when people would come to me and say, you know, you could make a lot more money if you would do such and such. You should consider going for an IPO. Let’s get some investors involved. We could really grow this thing. Well, that was completely lost on me. I had no interest in that at all because I wasn’t doing it for the money. In fact, getting other people in to lead my company or even hiring other programmers would have made the whole thing moot for me. With CD Baby, I did all of the front and backend programming myself. There were no other programmers. It was just me. And that was why I enjoyed doing it. If you were to just bring in a team of programmers, I would just lose all interest and shut it down because there was no reason to do it anymore.

The same thing with even making music. For 10 years, I was a full-time musician. And I insisted on playing all of the instruments myself and singing everything myself. And every now and then, a well-meaning producer would listen to it and say, ‘You know, you really should just get a different singer. You’re clearly not a singer. Just get a better singer.’ And I would say no, out of the question, because that would lose the whole point of why I’m doing this. I’m not doing this in order to have the best final product. I’m doing this in order to practice my singing and see if I can improve as a singer. That’s the reason I’m doing this. If other people like it, that’s just a side effect. My primary reason for doing any of this is the personal improvement aspect of it.

Srini:

I love this. You’re speaking my language and I think this is really going to jell with people. I knew you’d probably take us down this direction because I read on your website the main reason you do anything is for intrinsic motivation. And I’ve always found this to be one of those things that is very complex to understand. We can understand something like what you’re saying very intellectually, but it’s lot harder to internalize. And I remember Danielle LaPorte told me in an interview ‘Your life can never be about the money.’ And my response was ‘Yeah, that’s easy for you to say. You’re Danielle LaPorte.’ And yet, when I finally got that, a lot of things started to change and I guess I’m interested in how people find their way to their own intrinsic motivation if that makes any sense.

Derek:

Well, I think we all start out there. If you see a kid playing with LEGOs, you don’t ask ‘Why are you doing that? What is the ultimate goal? It would be a much better castle if you would have somebody else do that.’ Nobody would say that to a kid. No, you understand he’s enjoying playing with his LEGOs.

So I just feel the same way. I’m doing this because I enjoy it. And I think people just get money-driven. You get this kind of necessary and fear. Like, I need money. I need lots of money. What’s the best way I can make a lot of money? I can make this big company and we can get a lot more money if we get all these investors and the investors will give some money. We can make some money that way. If you get really, really driven by that stuff, then it changes all of your further decisions. This isn’t play. This is work. This is serious. We need to get the maximum return for our investors. Otherwise they’re going to be upset and give me grief.

But I think the lesson I learned way early on was -- my very first long-term girlfriend when I was a teenager, 20 years old, she grew up in this hippie family. She grew up in a commune in Vermont with no electricity. She never had a TV. She grew up with almost nothing and her parents didn’t have jobs. They just did random little, odd jobs. And yet they were able to put her through college. Because they kept their cost of living so low, they could just do whatever they wanted. Just doing random projects was enough to pay for their cost of living. And that was a huge influence on me.

So, although I did get a job straight out of college - I got a job in the tape room at Warner Chapel Music Publishing in New York – I kept my cost of living low. I was earning $21,000 a year salary, but I kept my cost of living down to $12,000 a year just because I spent nothing. I was just renting one room in a house with three other guys. I spent no money on anything. I never even took a taxi. I would spend hours just waiting for the subway because it would save me $4 or whatever, but I kept my cost of living down to nil. So after two and a half years of working there, I had saved up $12,000 and I quit my job. That was the last time I had a job. It was 1992 when I quit my last job. And I’ve just found a way to live cheaply ever since so that I can have freedom to just do whatever I want and not do things for the money.

Srini:

This raises a ton of questions. Specifically around the internal narratives around money. It’s such a complicated issue that raises some real emotional hot buttons for people, myself included. It’s interesting. You went from that position to selling a company for a seriously large amount and, not only that, but donating all of the money. So I’m interested in how your internal narrative around money and wealth has evolved over time. And why do you think so many people struggle with this? More importantly, how do they start to change it?

Derek:

Remember the second half of that question because I’m going to forget it. I’m going to just talk about the first half of your question.

When I was a full-time musician living in New York City, and the way you do that is you just say yes to everything. If somebody says ‘Hey, we’re looking for a heavy metal guitarist for this recording session.’ Yep, I’m a heavy metal guitarist. Count me in. Somebody says ‘Hey, we’re looking for a jazz piano player for this art show.’ What does it pay? ‘$350.’ Yes, I’m a jazz piano player. Count me in. Then I’d quickly go practice piano and learn some basics, enough to get paid. And that’s how I made a living as a full-time musician. I even bought a house with the money I made touring. So to me, that was like the measure of success as a musician. My measure of success as a professional musician is that I was able to make my living doing it full-time.

But then I really enjoyed reading books on sales and marketing and applying those lessons to my music business. So I would get a call from a university saying ‘Hey, we’re looking for a solo acoustic performer for August 12. Are you available?’ I’d say probably, it depends on what you can afford because I’ve got to travel to get there. They’d say ‘Well, we can only afford $300.’ I’d say, sorry, I can’t do it for anything less than $500 because of such and such. They’d say ‘Well, that’s really the best we can do. Our maximum budget is $400.’ I’d say ‘Well, I can do it for $400 if you’re able to help me contact some of the universities next to you to line up some gigs the day before and the day after. Then I could do it for $400. And they’d say ‘Okay, sure.’ I’d hang up the phone and go Yes! I did it. I made an extra $100. I’m going to book two gigs now instead of one. And I’d get such a sense of achievement out of having done that. And the money was definitely part of that. It was like this neutral measure of success. I got $400 instead of $300 for that gig. It was easy to measure.

What’s funny is it wasn’t selling my company that actually got me rich. CD Baby was quite profitable on its own. I think it was making a net profit of about $4 million a year. I had no investors. I was the only owner. So already just 4 or 5 years into it, I was making enough that I could just retire right then if I wanted to assuming I keep my cost of living low. But there was a little bit of sadness around this. For the most part, when I was deep into CD Baby, it was completely intrinsic. I wasn’t doing it for the money. In fact, I barely even looked at my bank account. Just a couple of times a year, I would look at my bank account and go ‘Wow. That’s bigger than I expected. Cool.’ I wasn’t even really keeping my eye on the money because I was just busy making CD Baby what it needed to be for its own sake. There was a little bit of sadness, though, around missing having that clear measure of success. I missed getting excited about getting that extra $100 for a gig.

I’ve actually talked to a couple of famous musicians about this. They say that is one of the downsides of getting rich and famous. They kind of miss the hustle, the joy of booking a gig and getting 20 people to come down to a club or whatever. You can miss that aspect later as it grows. But all it means is that you just have to start doing things completely for intrinsic reasons or other reasons. Sometimes people turn their attention to charitable reasons. Am I able to help create a school in Cambodia? Or something like that. That can motivate them more than earning an extra $100. All that said, making a lot money is awesome. It’s a wonderful security. It’s like once you’ve got that covered, you just turn your attention to the other stuff and no longer really ever do anything for the money again, which is actually kind of a hard habit to break.

Srini:

Let’s talk about people and their internal narrative around money. Do you think you’ve got to get to that point of selling something for that much? Actually, this is the bigger question around this. Can we shift the narrative so that the circumstances change?

Derek:

How do you mean circumstances?

Srini:

Let’s say that you’re not where you want to be financially and a large part of it is driven by your internal narrative around money. Can you shift the dialogue you’re having with yourself around money and your relationship with money so that the situation financially changes?

Derek:

Good questions. Clearly, yes. You kind of knew the answer is yes.

Srini:

I knew the answer is yes. I want to know is how. And I’m wondering is this just isolated to certain individuals or are some people just destined to never be rich?

Derek:

We each have things that trigger us in different ways. I remember years ago reading a Tony Robbins book where he was trying to motivate the reader by saying imagine all the things you could buy. Don’t you want to have your own helicopter? Don’t you want to buy a private island someday? Imagine driving your brand new fancy sports car. I remember reading this feeling, nah, that’s all lost on me. That does nothing for me. Whereas I know some other people directly that are very, very influenced by this idea of I’m going to work extra hard. I’m going to focus on adding value to my customers. Or I’m going to create the best customer experience because I want to buy a Ferrari. And it’s not shallow.

There was even an interview with the Beatles once, I think a couple of years after they broke up in the ‘70s. An interviewer was interviewing Paul McCartney, and he said something like, ‘You know. People like to glorify the Beatles and thinking that we’re all just peace and love, man. But when John Lennon and I were writing those early songs, we would sit down and say let’s write a swimming pool. Let’s write a song that is going to earn us enough money to buy a swimming pool.’ So it was definitely motivated by money.

You’ve just got to know what works for you. To me, it was the freedom. This idea of earning enough to feel free. To not have to do anything for the money, which clearly was pretty easy for me because I was able to keep my cost of living down to $1,000 a month. So if I was able to do just even a couple of gigs in the New York for a few hundred dollars each, then I had earned my monthly cost of living and everything on top of that was just extra. So there’s thing, like, you can keep your cost of living way low.

But on the other hand if you read Richard Branson’s autobiographies, he was driven by this sense of desperation. He would get himself into a jam somewhat intentionally. He would always go down to the last wire. He would borrow from the bank, spend it all on everything, get himself into a jam and then be forced to do some kind of big money-making gamble at the last minute in order to get the bank back their money by tomorrow when it was due. And a lot of his growth was driven by that sense of desperation. That wouldn’t work for me.

So anyway, if you’re talking about the narratives we create, I don’t think anyone can just hand you down one and say this is how you need to think about money. You’ll just listen to lots of different people talking about money and motivations and you’ll find that one clicks for you, one works for you.

Srini:

That’s interesting. It reminds me of a conversation I was having with a friend of mine the other day. I’d just gotten back from trip to El Salvador. I said it’s really bizarre. When you boil it down, my motivation for everything that I’ve gotten to do - write books, produce this show – the whole motivation right from the beginning was so that I could surf whenever I wanted to. That was my ultimate motivation. It trumped everything else. And all the other things, like you said, are just kind of byproducts. But that one thing has always been so consistent is that I’m willing to do whatever I have to in order to make sure that I have the ability to do that.

Derek:

That’s a great thing to realize. And sometimes you can only find that out through experience.

Srini:

Oh yeah. I’ve lost sight of it at times. I’ve definitely lost sight of it at times.

Derek:

I don’t think we should ever regret our bad times in the same way that we shouldn’t regret our bad relationships. So many people that you date early on, you’re together, your long string of boyfriends or girlfriends, each one is teaching you what you don’t want. You break up with that person and go, ‘Never again will I be with somebody who does that.’ And I think as you go through life, that’s how you learn what you do want. On that note, you brought up the fact that most people think it’s weird that I gave everything away or put everything into a charitable trust.

That to me just came from this aesthetic I have of understanding the word “enough.” I really like knowing what’s enough. So this even comes down to personal décor, for example. If you look at my house, there’s almost nothing in it. It’s only what I need for me and my kid. I don’t usually tend to entertain guests. In fact, I pretty much never have more than one person over. So for example, I only own two plates because that’s enough. I don’t need 8 plates because I never have 8 people over. I don’t want 8 people to come over. So I have two plates. That’s enough. And I only own one pair of pants because you can’t wear more than one. So things like that. I really like understanding the word ‘enough.’

And so by the time I was selling CD Baby, I already had a few million dollars saved up. And that was enough for me. That was enough for the rest of my life assuming that it’s just conservatively invested and I’m living off the interest and not touching the principle, then that’s enough. I spent a few months thinking what the fuck am I going to do with $22 million? And I realized that all of the ideas I was thinking of were violating my aesthetic of ‘enough.’ I don’t want the $22 million. All I’m really going to do is give it away. And I talked to my lawyer, who is also a friend and also had the tax law background. When I described to him that I was just going to give it all away anyway, that’s when he said, you know, if you really, really mean that and you’re sure you’re never going to change your mind on that, there’s something you can do where you can give it away in advance. And so that’s why I did that. Giving it away in advance had a few psychological benefits too. So the tax benefit was instead of me earning $22 million personally, then paying $2 million tax on that, and really only having $15 million to give away to charity, by giving the company away in advance of selling it, meant that all $22 million goes to charity and never touches my hands. It’s also had a psychological benefit because I would never have this sense of regret, like, maybe I should have just bought a Ferrari first and then given the rest away. Or even just having $15 million sitting in an account with my name on it might have been dangerous in a lifetime. If I get depressed or something, I might go do something stupid. So I really liked the fact that it took it out of my hands, so I didn’t have it to spend.

Srini:

Can we bring about these psychological benefits even in small ways? Like in our day- to-day transactions with money?

Derek:

Oh God, yes. That’s what’s brilliant about reading these books about behavioral economics. Like “Predictably Irrational.” You read “Predictably Irrational” or you read “Thinking Fast and Slow” by Daniel Kahneman. There’s a whole series of these books. “Stumbling on Happiness” and “The Paradox of Choice.” A lot of them are around the subject of behavioral economics, which is learning about the faulty wiring in our brain and then ideally setting up your life in such a way to take advantage of or protect yourself from your faulty wiring.

Srini:

Can you give us a tactical example of how we might apply this in a day-to-day transaction?

Derek:

Let’s see, “The Paradox of Choice” is quite popular. We all know this idea of having some choice is good, but that doesn’t mean that having more choice is always better. And when you read and understand that message, you realize that you don’t need to give yourself the maximum number of options. In fact, you’re happier if you do what they call ‘satisficing’ instead of ‘maximizing.’ If you say the phrase ‘good enough’ a lot when making a decision. Like, this car is good enough. I don’t need the best possible car that’s available to man. I don’t need the best possible computer. I just need one that’s good enough. Believing that and really internalizing that can save you a lot of money.

There’s also the book “Stumbling on Happiness.” It sounds like it’s new agey, but it’s not. It’s written by a professor of psychology at Harvard that’s been studying happiness for decades. And one key finding is that when people buy some new thing, the happiness it generates is actually only in the moment of comparison where you’re comparing your new things to your old thing. In that moment, yes, you are happy. But once you’ve had this new thing for a while, and it might only be a week, you’re no longer comparing it to your previous thing anymore. It now has just become your new normal. And the happiness from that item fades away because you’re no longer comparing it.

So if you really understand that, then there’s no need to buy every new iPhone just because you hear of all its benefits. You understand that I could go spend $1,000, even it’s subsidized, when you add it up, it’s still coming to $1,000 or something. I could spend $1,000, but it’s really only going to make me happy for a week. Is that worth it to me? There are people who spend extra to fly business class or first class. It’s like, how much is 6 hours of happiness worth to me? Because the moment I get off that plane, I get there at the same time as the people in economy, so am I really going to spend an extra $4,000 to be happier for 6 hours? Use these kind of behavioral economic questions, understanding and realizing that the studies that have been done also apply to you.

Srini:

I think that is a perfect transition to something else I want to talk about. One of the things you said on your website is that you’re fascinated by usable self-help. I actually really appreciated that because I felt so often that so much self-help material is just a bunch of inspirational psychobabble that doesn’t translate into actual results for people. And what they end up doing is just becoming addicted to self-help. I love that idea of making self-help usable. So I’m curious. Why is so much of it unusable? How do we translate it into something usable? And how have you translated it into something usable in your own life?

Derek:

Most of it I think just is a way of thinking that makes people feel better. And that’s totally valid. I have nothing against that. If you had some very difficult things happen in your life and you are able to read something that helps you reframe that in such a way that it makes you feel better about it, then that’s great. And I think that’s maybe why people become addicted to it. It’s because while reading that book, while the author’s words are still echoing in your head, written in that beautiful inspirational way, you feel so much better in that moment. And maybe you feel better about your future. Maybe you’re reading something that is inspiring you for the future. And in that moment, you’re filled with a sense of hope and optimism. You feel really good about it. You finish the book and you go to sleep the next day and you don’t change anything.

And you’re kind of, like, I miss feeling that good. I’m going to read another book. So you read another book. Now you think, I can be anything I want. The world is mine. This feels really good reading this. And then afterward, the feeling fades because you go back to doing the same old thing.

I’d still have to say, though, that’s valid. Sometimes you really do need to feel better about things that have happened in your past. I’ve definitely had that with books that made me feel a lot better, just thinking of things that have happened to me in the past that were really annoying me, still stuck under my skin. And I read something by this author that just made me feel like, oh, that’s a really nice way to think about it. That feels really good. I don’t know if I actually changed my actions in that moment. I think it just felt really good and I made my peace with this thing in the past.

One thing you can do, by the way, to solidify these events, which I think is really great about blogging, is that when you take something that you’ve recently learned and you share it in that moment, especially if you share it publicly in a way like that, you internalize it more. It becomes part of your self-identify. See, I’ve blogged this. This is who I am now. This is a part of my public self and therefore my real self. So that’s a good way of internalizing a way of thinking about something.

As far as action, I wish more authors would give directives like do this. The most recent blog post on my site, at least as of now, is about this new project I’m doing where I felt like I’d read 225 books in the last few years. A lot of them were these really interesting observations about life and psychology and what-not. Most of them don’t want to take that extra step into telling you want to do about it. They just leave the reader up to their own devices. Well, here are some really interesting observations about the way the world works. So hope this is useful to you. Good luck. Most people don’t turn it into something.

There was this paragraph that had a huge impact on me in this book about stoicism called “A Guide to the Good Life,” where he said back in the days of the classic stoic philosophers, they would tell you want to do with your life. If you were to ask one of them ‘How can I live a good life?’ or ‘How should I live my life?’ they would tell you here’s what you should do. But I get the feeling that today if you were ask a philosophy major or philosopher ‘What should I do with my life?’ they’d say, well, depends on what you mean by do, it depends on what you mean by life, and it depends on what you mean by my. They would just talk in circles all around this thing and you’d never get to the simple directive of ‘do this.’

Thinking of the Ten Commandments. The Ten Commandments were not there to discuss all of the various issues. They just said do this, don’t do that, do this.

I think there’s really something powerful about prescribing an action. In fact, I think the action carries the philosophy inside of it, kind of like a seed. Like trees, their seeds go flying in the wind and it carries the seed inside of it. So the philosophy is carried inside of the action. You can just give the action, and you’re prescribing the philosophy inside of it at the same time. I wish more books did that, but they don’t.

And so a new project I’m just barely starting, I’m not even sure what form it’s going to take, I’m in the process of taking everything I’ve learned in the past however many years and however many books and turning it into specific actions to prescribe.

Srini:

I’ve asked this question to a lot of people. Still to this day, I wonder if I get an answer because I’m asking the question or because it’s a universal experience. Throughout this whole trajectory of yours, have there been any sort of rock bottom, dark down to the soul, no hope for the future moments?

Derek:

No. I’m really lucky that when I was 16, my grandma had a book on her shelf called “How to Win Friends and Influence People.” I read that and it had a big impact on me. And I’m lucky that I was an ambitious 16-year-old, 17-year-old, wanting to be a rich and famous musician. I saw a little book. W. Clement Stone was the author. I forget the name of the book now. But it was just one of those classic 1930s self-help books. I just devoured it when I was 17. I just really internalized it.

When I was 19, my boss in the circus – I worked in the circus for 10 years. I was, like, a ringleader, MC of a circus – and my boss at the circus really cared about me and she said, I read this book called “Awaken the Giant Within” by Tony Robbins. I think you’d really like it. And oh my God, when I read that at 19, it just floored me. I read it again and again. I just totally internalized everything he was talking about. I read it again when I was 20, again when I was 22, again when I was 23 and listened to everything he put out and all of his interviews with other people and I really internalized those philosophies.

So much so that things that were very deliberate at first, like a classic a Tony Robbins line is ‘Whenever anything bad happens to you, you have to ask yourself what’s good about this?’ And remember the first time I heard that, I was like oh, okay, maybe and then the next time something bad happened to me, I didn’t remember to be that, of course. But the next day, I was, like, I probably should have asked myself what’s good about this? And the next time something bad happened to me, I remembered to ask what’s good about this? And eventually, over years, it became an instant reaction. Now the very second something bad happens to me, I catch myself saying what’s great about this? And therefore, I don’t really ever get beaten down by things. I’m just in the habit of finding a useful aspect to it immediately.

Srini:

So you worked in a circus. That is really interesting. I’m curious. What kinds of lessons did you bring from working in a circus into all the work you ended up doing in the rest of your life. What did you learn from that?

Derek:

The way to entertain a crowd is to make it all about them, not about you. I think when I was 18 years old and I got up on stage at the circus with almost no performing experience, - I’d been a musician for a few years, but hadn’t been a great entertainer really – I was really bad at first. And then my boss at the circus and the whole crew there kept pushing me. No, you’ve got to be more entertaining. These people are looking for entertainment. Don’t just get up there and stare at your feet. Put on a show. It took a long time for me to finally understand that lesson.

I put on over 1,000 shows over the next 10 years and got a lot of experience in how to entertain a crowd. If you can entertain a crowd of 4-year-olds, you can entertain anyone. It’s kind of funny. When later I was performing at universities across America and did the exact same tricks that I learned for captivating a crowd of 4-year-olds, I found it also works for 20-year-olds.

So the bigger life lesson learned is that if you want to entertain an audience, it’s about them, not you. You can’t just get up there and talk all about yourself and dive too deeply internally unless you’re also going to do the masterful work of finding a way to dive deep and make it entertaining to others. To me, it’s a priority to make it about other people. So everything you see on my site, sive.rs, I’m doing for others really.

Srini:

I want to talk about another component I saw on your site. I want to talk about the idea of if it’s not a hell yes, it’s a no. I want to talk about where that came about, how it’s impacted your life and how it might impact our lives. And how that ties into this whole idea of anything you want.

Derek:

The ‘hell yes or no’ philosophy says it’s when you’re feeling overwhelmed, overbooked, there’s too many opportunities and not enough time, then you should beware when you’re thinking just say yes about something. If somebody says ‘Can you come speak at our conference?’ if you’re internally feeling like ‘I could. They’d pay for my travel to San Francisco and I could also see my sister. So I guess I could do that. I guess it could be beneficial.’ My point is that should be a no.

When you’re overwhelmed, if you’re feeling anything less than ‘Oh hell yes! That would be amazing!’, then you have to say no. When we say yes, we end up filling our lives with this little tiny crap that we’ve obliged ourselves to do. It just fills up all of your time so that you don’t have enough room in your life for those big ‘Hell yes!’ things that come along rarely. On the other, if you said no to all the stuff that that you don’t feel that strongly about, then when you get the occasional ‘Oh hell yes!’ opportunity, then you can just let it fill up and expand because you’ve got lots of room in your life to dive into those things.

This has worked really well for me, but I have to emphasize that it is a technique that applies only when you’re feeling overwhelmed. When you have more opportunities than time. When you’re starting out and you have more time than opportunities, then the correct strategy is to say yes to everything.

It’s kind of like what I was saying earlier about being a professional musician in New York. Any time anyone had a paying gig of any sort, even it’s not a ‘Hell yes!’ sort of thing. My very first paying gig was $75 to play guitar at a pig show in Vermont. And it was a $60 round-trip ticket to get to Vermont. But I said ‘yes’ because it was my first paying gig and you’ve got to say yes to everything. Every little tiny thing you say yes to can lead to more opportunities when you’re first starting out.

The point is that we need to learn to change strategies along the way. So yeah, if you’re starting out and you have more time than opportunities, just say yes to everything. Go to Craig’s List and say yes to a bunch of stuff on there for people asking for help. Go make yourself available to the world and say ‘I’m here to help anybody do anything. What do you need?’ Just do everything. Chase every opportunity. And only later when you’re overwhelmed with opportunities and you’ve got more money than time, then you can start changing strategies and apply the ‘hell yes or no’ approach.

Srini:

This has been fascinating, Derek, as I expected it would be. I have one final question for you, which is how we finish every interview. What do you think it is that makes somebody or something unmistakable?

Derek:

Unmistakable. I was thinking about that word before we got on the phone. I’m assuming that if you interpret ‘mistakable’ as the ability to be mistaken or as able to be mistaken, kind of like the word ‘misunderstood,’ then to be unmistakable, you must be very clear and unambiguous. It reminds me of one of my favorite bits of advice about writing. ‘The key to good writing is not to be understood. It’s to not be misunderstood.’ That’s the bigger challenge. People are very likely to misunderstand what you’re saying unless you’re very clear. So what makes someone unmistakable is to be very clear in your own head and in how you’re living according to your beliefs. To be very clear and unambiguous makes you unmistakable.

Srini:

I really appreciate you taking the time to join us and share your story and your journey and your insight. This has been great.

Derek:

Thanks Srini. For anybody who makes it to the end of this interview, as I mentioned earlier, I actually enjoy putting aside a little time every day to answer every single email I get. So feel free to email me. Introduce yourself. Ask me anything and I’m happy to help.

Srini:

I’ll be sure to link up all the books that Derek mentioned in the show, along with some of the blog posts we’ve talked about. We’ll wrap the show with that. Thanks for listening to The Unmistakable Creative.