Derek Sivers

Interviews → Gary and Robbo / Mojo Radio

Beliefs expire. Add value to others. Understand what works for you. You don’t need more. Operating at a different pace, and more. Fun talk.

Date: 2020-01

Download: mp3


Host: Gary Bertwistle
Producer: Darren “Robbo” Robertson


So I’ve been chasing today’s guest for six years. I still remember I was on holiday on an island. I finished this guy’s book and at the very end of the book, he actually dropped his email address and said, “I’d love to hear your thoughts. Please contact me.”

His name is Derek Sivers. He wrote a book called Anything You Want. I really like the book. It is one of the books that I read again each year. To his credit, I wrote to Derek six seasons ago. He was one of the very first guests I ever wrote to and he said, “I’m programming. Now’s not a good time. I’m completely focused on this. I’m not doing anything else. Keep in touch.”

Then I wrote to him each year probably two to three times a year and asked is now a good time? He always wrote back and said, “Now’s not a good time.” Then he wrote a brand new book. In fact, he’d written three new books. And I wrote to him to say, “Would you like to talk about the books?”

He said, “No, I wouldn’t like to talk about the books because I don’t like coming on shows to promote and blow my own trumpet, but I will come on your show.”

This show was literally six years in the making. We kept this show back to start season seven because it is quite special. It is about resilience, persistence because those things can show themselves in lots of different ways, not just a sporting field or on the business boardroom table.

Without further ado, would you please welcome Mr. Derek Sivers to the radio show?


Thanks for the call.


When people Google you – Tim Ferriss, Ryan Holiday, Simon Sinek – are the names that come up around you. What do you think you guys all have in common?


Probably an aim to keep doing things in the public eye. I’ve found that to be a difference. When I was living in New Zealand, it was very easy there to just turn inward and do things for myself.

I saw a difference between that and my previous focus of constantly doing things for the public, in the public, keeping it out in the public eye. Trying to get a broad reach to what I’m doing. It takes an extra effort to put your ass on the public line instead of just on your private achievements.

You’re putting yourself out there for critique more. So it’s a bit of a pain. I don’t completely enjoy it, but it seems to be worth it. That’s the difference between just being a private success to yourself and being more of a public success.


What you do that’s interesting to me is that you’ve said you have a lack of interest in the existing game. Where does this stem from? What is this desire to not play the existing game that the majority want to play, yet the majority don’t want? Where does that come from?


I can think of two things. For one, the background that really shaped me was in the music business.

From the age of 14 years old, I wanted to be a famous rock star or at least a successful musician. My heroes were people like Prince or Miles Davis or David Bowie. They were people that would always do things differently from what everyone else was doing.

That was the strategy to success in the entertainment world, which is usually to do the opposite of what everyone else is doing. If you do what everyone else is doing, then you’re yet another one of those little names that pass by on the radio. There are the innovators then there are the followers.

If you want to be an innovator, if you really want to call attention to yourself and do something cool that people pay attention to, then you look at what the rest of the world is doing and you do the opposite. So that’s part of it, but then it also comes from the fact that I’ve been happy since the mid to late ’90s. I’ve just been happy with where I’m at in life. I ticked off most of my boxes for what I wanted out of life [laughter] by the mid to late ’90s.

Everything after that feels kind of light-hearted. Everything else is just dessert. I don’t need to do anything I don’t want to do. So I look around at what I don’t like about the world and I don’t do it.

I’ve never liked TV. I’m not gonna watch TV just so I can chat at the water cooler about Game of Thrones. Fuck that. I’d rather reclaim that 300 hours of my life.

Same with people who are all into Instagram. I look at that and go, “No. That doesn’t look like fun. That looks kind of disgusting [laughter].” So I won’t do it.


There are a couple of stories that I want to recount with you about people and circumstances that shaped who you are. I want to talk to you about the circus and what the circus taught you early on when you were starting out in your life, in work, and in business.

Take us back to that time in the circus and the greatest lesson you learned from that time.


When I was 18 years old, I got a call from a booking agent. I was living in Boston. I was going to Berklee College of Music. It was just a random call for a gig. It was my very first paying gig ever. A booking agent called offering $75 to play at a pig show in Vermont. I was like, “Hell yeah, a paying gig!”

I said yes even though it was a $50 round trip bus ticket to get to the gig and back and the trip took all day. Spending all day to make $25 doesn’t sound like a good deal, but I was psyched because it was my first paying gig. So I went to a pig show in Vermont and played for a few hours and came home. That’s how I got hired to play at the circus because that booking agent that booked me also ran a circus.

It was something that plopped into my lap. Two interesting lessons came out of that. I prepared some thoughts before our call. I was thinking about the subject of your show and why people listen to the show. I made what I call the Mojo Lessons.

So the Mojo Lesson here is about overacting. When I first started the gig, they needed me to be not just the musician, but also the ringleader M.C. I’d get up there on stage and I’d go, “Hey, everybody. Welcome to the circus. I hope you like the show today. We’re about to begin.”

I’d go backstage and they’d say, “No! You need to be more sensational. You’re being too casual.”

I’d get up on stage the next time and go, “Uhh hey, everybody. Welcome to the circus. Hope you like it. . .”

I’d go backstage and they’d say “No! Be more sensational! Be more entertaining. Come on! You’re the ringleader. You’re the M.C.”

So I went up there aggressively and rebelliously. Over the top. I thought, “I’ll show them.” I meant to go too far. I did it to punish. You know that thing you do ever since you’re a little kid when somebody does something and in anger, you do it over the top?

I went up there and I said very aggressively, “Ladies and gentlemen! What you’re about to see is one of most sensational things you’ve ever seen! We’re about to have dolphins coming out of the sky. We’re going to have bears jumping through hoops. You’re gonna see this and that! Ready for theeee circus!!”

I went backstage and they said, “There! Now that’s what we want!”

It worked. It was great. From that day on, that became my stage persona – this overacting, over the top version of fake it ’til you make it. Then years later, I was playing guitar for a Japanese pop star, Ryuichi Sakamoto. I had moved to New York City and I got this random gig offered to me. I said yes, so I went to Japan to play guitar for a guy that’s like the Peter Gabriel of Japan.

This was the opposite where they put us in these black designer suits. I would get on stage. I loved this guy’s music! I’m up there in front of 10,000 people playing guitar, and I’d go backstage and they’d say, “You are moving too much. Could you please try to stay still?”

I’d say, “OK,” and I’d get up on stage the next day and I’d be a little more still. They’d say backstage afterward, “No. We need you to be much more still.”

Once again, I did the overacting. I went over the top like, “I’ll show them. I’m gonna be a fucking statue. I’m gonna be absolutely still! That’ll show them.” I went onstage and I did not move. I played my guitar and didn’t move an inch. I went backstage and they said, “There! Thank you. That is exactly what we want.”

I thought, “Oh, well alright.”

There’s a life lesson here. We’ve all heard the fake it ‘til you make it advice, but I think sometimes if you really want something and you’re just not getting the results, try overacting.


This is interesting. I’m gonna go a little off-ramp here because you just used the word stage persona. I’ve heard you quote Kurt Vonnegut who said, “You are what you pretend to be.” When you think today of your own persona today, based on that quote, what are you pretending to be today?


Nobody’s ever asked me this. There’s a funny thing among famous people. Which is your last name. If you use the full version of your name, that is your famous self. When you’re just among friends, you only use your first name or your nickname. I’m friends with Tim Ferriss for example, and people joke like, “Oh, look. Tim Ferriss says I shouldn’t do this.” [Laughter].

When you say the last name, you’re referring to the public persona. Ideally, I wish that everybody had a stage name. Bono from U2, his real name is Paul Hewson. If somebody calls him Bono, he knows that they’re referring to the public persona he’s created.

That has two advantages. For one, if somebody attacks the public persona, somebody says, “Oh Bono, he’s just full of himself, he’s a blowhard!” They’re not talking about Paul, they’re talking about Bono. Somebody can attack it all you want and it’s as if you drew a drawing of something and somebody is attacking your drawing. You know, it’s not you. It’s something you made.

It also works for compliments and praise. It helps you from getting too full of yourself. If somebody sitting is saying, “Oh my god Bono’s a genius! Bono’s a modern-day savior!” Then they’re still praising the drawing you made. It’s not the real you. It’s separation.

So I wish that we all had stage names. My kid’s only seven years old, but it just came up last year for the very first time. He was about to create some kind of a public profile I think on Minecraft. I said, “Well, it’s time to make up your Internet name.”

He said, “Internet name?”

I said, “Yeah. What is your Internet name gonna be? Because it’s not your real name. You’ve got to make up what name you’re gonna be on the Internet.” I gave him this as a fact of life. So he made up an Internet name. I think we all should do that. If you’re going to do something in the public eye, make up a name for it. Then that public persona can be whatever you want to call it.

You know those people that are public jerks? I’ve never seen the show, but there’s a cook, Gordon Ramsay. Isn’t that his whole thing? He attacks people in the kitchen and is just a raging jerk to them. So who knows if he’s like that in real life? Or maybe he’s a sweetheart that just crafted this public persona because he knows that people tune in to watch people being jerks.

So you can craft your public self. There’s an interesting book about this. I’ve felt this for years, maybe because of my background in music, but recently a book came out called The Alter Ego Effect that was surprisingly good. It was about how to apply this way of thinking to everyday life.

I think the author is a coach to many athletes, and he found that a lot of athletes have an alter ego that they think of when they’re about to go out on the field. When they’re back in the locker room they’re saying, “OK it’s time for the Tiger Ninja to come out.”

They have these code names for their performing self. He found that some executives have this too, “OK, here goes the dealmaker. Dealmaker’s going into action.”

It’s a really interesting subject. I did accidentally do that thing where you asked me one question, and I answered a related question. All that stuff I just said was more about alter ego than it was about the Kurt Vonnegut becoming what you pretend to be, because you’re right. That is a different thing.

If you really want to become something there is the classic fake it till you make it. Or acting like something until you become that something. So sorry, I didn’t really answer your question directly.


It was still a damn good answer though. We’ll take it [laughter].

What’s interesting is that if you look at creating an online name that your son adopts online for that game and so on, what he talks about is that it’s going to be a part of you and not the whole of you.

Todd Herman does talk about that fake it ‘til you make it, but it’s actually not that. It’s actually knowing the identity you step into to create the values and the persona you would like to use to go beyond perceived barriers.

Do you have an alter ego today in Derek’s world? Is there a character, a person, a persona, an animal, a piece of music that you step into when you need to get beyond your own perceived barriers?


Not like that. No, I don’t really have the backstage, here comes the Ninja Tiger kind of thing [laughter]. But I have found that, for example, my writing, which is what most people know me for now, has a very succinct, direct style that just appeals to me.

It seems like my persona because most people just know me through my writing. I like being very succinct. I don’t want to put a sentence out into the world unless that sentence is really needed. So I edit the hell out of everything I put out into the world.

So that makes me seem a little more sage-like than I really am when I’m sitting here talking and I get overly excited and tell these long-winded stories [laughter]. It’s not very sage-like. I’d say that’s a different persona. There’s my writing persona who really is me, but it’s focusing on a certain side of myself that’s trying to be as succinct as possible.


When I was writing to you – we have conversed over a number of years, there was a story you told of a music teacher that very early on impacted you.

You were very gracious to say “Yes, keep in contact,” but I knew that this music teacher was resonating in my mind to know that you have to follow through. Tell me about meeting this music teacher, the lessons you got from it, and how that impacts your world of learning today?


The Mojo Lesson of this story is the power of a different pace with Kimo Williams. I was 17 years old. I was living in Chicago and I was about to go to Berklee College of Music in a few weeks. It was the summer holidays before beginning the new school year.

In Chicago, I saw a classified ad in the paper about music typesetting and I had a question about it. I called the phone number and the guy answered my question. He goes, “Why do you want to know?”

I said, “Well, I’m about to go to Berklee College of Music...”

He said, “Berklee College of Music? I taught at Berklee College of Music. You know, I’ve got a theory that I think I think you can graduate that school in half the time it takes. Why don’t you come to my studio tomorrow morning at 9 a.m. and see if I can show you a few things.”

I said, “Great!”

I showed up at his studio at 9 a.m. the next morning, and apparently, he tells this to every young, ambitious musician that asks him questions. He says, “Show up at my studio at 9 a.m. tomorrow.”

I was the first one that ever showed up. He told the story years later at my wedding that he’d been saying this for years to students, but nobody ever shows up at 9 a.m., so I showed up early and ready to learn.

He sized me up and said, “Alright, now, look. The world goes at the pace of the lowest common denominator. Especially schools. They have to teach the curricula in such a way so that nobody gets left behind. If you are smarter than the average, if you’re more focused than the average, you can go so much faster than most people. So I think that the stuff that Berklee teaches you in four years, you can learn it all in one or two years. Let’s give it a try. Are you ready?”

I said, “Yeah!” He opened up this book of jazz standards and he asked, “What is the major scale?” I answered correctly.

Then Kimo asked, “OK. How do you build a chord off the second note of the major scale?”

I said “D F A C.”

He said, “Right. What kind of chord is it called?

I replied, ”That’s called a two minor chord.“

Kimo asked, ”So what is the five chord“

I answered, ”G B D F.“

He said, ”Right. That’s a five chord. A resolution in jazz harmony is a two to five to the one. Why does it resolve? Because you’ve got the tritone there in the five chord don’t you?“

I said ”OK. Yeah. What is a tritone?“

Kimo answered, ”It’s dissonant. It wants to resolve. Now building a scale – where else can you put the tritone into a seventh chord?“

I went, ”Uhhh the D flat seven.“

He said, ”Right! That is called a substitute chord. Now, make substitute chords for each one of the chords on this page. Go! I’m going to give you one minute!“

It was this intense pace. It was so amazing. It was like learning music theory, but with the intensity of playing a video game or something. It had this adrenaline to it. I loved it! We kept up like that for three hours. After three hours, I walked out of there around noon and went back home. It felt like what we knew later from the movie The Matrix, where they go, ”Hold on. I’m going to teach you how to fly a helicopter...“

”Got it! Now I know how to fly a helicopter.“

I learned so much in three hours, it blew my mind. I went back there for the following weeks for the last three weeks before I began Berklee School of Music. And by the time I got to Berklee after only five lessons with Kimo Williams, sure enough, on my entrance exams, on my opening day of school, I tested out of four semesters of jazz harmony.

That stuff that I hadn’t known a month ago. I would’ve sat through four semesters – two full years – of harmony classes, to learn what Kimo taught me in a few lessons. So that’s the story of what happened.

He just taught me this core theory that there’s the standard pace that is meant to include everyone and leave nobody behind. That stuff doesn’t apply to you if you’re more focused, more ambitious than most. You can go way faster than the norm.


What is the T-shirt that came from that, that Tim Ferriss wanted to produce?


The standard pace is for chumps [laughter].


I love that [laughter]. That is one of my favorite sayings of all time. I love that. The standard pace is for chumps.


What’s funny is after I said that story publicly, I went and tracked down Kimo. I hadn’t talked to him in a couple of years. I said, ”Hey, man. I just told the story of how we met.“

Kimo goes, ”Standard pace is for chumps? I never said that word before. I never said that. I think you made that up.“ [Laughter].


As Kid Rock would say, “That’ll be on a T-shirt by Friday.” Obviously, I love that story and I love that saying.

I mention it to people and credit you often. When you got married, you only had three people at your wedding. An ex-girlfriend, which is curious, Kimo Williams, and another lady called Tarleton, who was the wife of the booking agent, that we started this show with, the story you told about the circus.

Tell me, Tarleton was a special person in your life. Tell me what Tarleton drew out of you as a man?


I was only 18 and she was probably 33. She was my boss or manager in the circus. It would mostly be that the other guys in the circus were asleep in the back of the truck, and she and I would often be the two drivers. I’ve never been that into sleeping [laughter], so I would often be up front driving the truck with her.

We had hours and hours to talk for six years in my life. Of course, being 18, I went through heart-breaky kinds of things. Got dumped a couple of times. I’d be moaning to her about being dumped.

She just kept saying over and over again – it helped that she was super hot and this older woman at 35 saying this kind of stuff made a difference – she’s like Derek, ”I’ve been with dozens, maybe even hundreds of guys. You just blow everybody else out of the water. You’re smarter. You’re more considerate. You’re sweeter. You’re a better catch than anybody out there. People just puff up. Any girl that doesn’t realize that you are just fucking amazing? That’s her loss.“

She told me this sweet stuff for years, and I think for the first year, or two, or three, I thought, ”Eh well, thank you.“ I thought she was just trying to make me feel better. But after three years of her saying this stuff, I noticed it slowly sunk in and just changed my self-image.

After a few years, I think the next time I had some kind of breakup, I really to the core felt, well, that’s a shame that she’s gonna miss out on being with me. I’m fucking awesome! I noticed that it felt like a truism to me. When I tried to unravel that and wonder why did I think that? I think it’s really because of Tarleton telling me over and over and over again.

Mojo Lesson: It’s OK to have somebody else assist in your self-image.


I wonder where that middle ground is because alter ego or identity has been a thread through the show, which I’ve been really interested in for probably three seasons now.

Going into our seventh season with this show, the other thing that we’ve heard a lot about, which I’d be curious about your perspective on, is that one of the most important traits in leadership is humility.

Where is that fine line between, ”Yeah, I am awesome!“ versus humility? How do you see that place, that beautiful spot, the sweet spot right in the middle there between those two things?


I haven’t thought about this a lot, but I’ve thought about it a bit. I think the difference is, whether you look down on others or not. You can think, ”I’m awesome,“ without thinking, ”You suck.“ It’s fine to be as confident as can possibly be on earth as long as you’re not looking down on others because of it.

I was thinking about the word smug. We tend to think of smug as a completely negative word, but I think smug is actually a feeling of pride. Meaning that you are living the life you want to live. You’ve been following your own best advice. You’ve been doing the right thing. You’ve been making the right choices. Now you’re really happy with where you’re at and who you are.

To me, that feeling is smug. It’s a positive thing, and I asked a friend of mine about that. I said, ”Why is smug a bad thing? Why do we think it’s negative?“

My friend thought about it for a second, and then he said, ”I think because it’s assumed when you say smug that you’re looking down on others. That you think you’re better than other people.“ There’s a difference. If we get rid of that secondary effect of looking down on others and just take the first half of it, those two don’t have to be inseparable.

Somebody was talking about sending their kids to a fancy, expensive, private school or not. He said, ”I don’t want my kid to be some kind of a privileged asshole,“

I said, ”Those two words don’t have to go together [laughter]. Your kid can be privileged without being an asshole. It’s not like everybody with privilege becomes an asshole.“

Why do we assume that there is always going to be this dark side? I like to separate those two things. I think being smug is a great thing as long as you don’t look down on others, but being smug is a wonderful feeling, ”Yeah, I’m living according to my values, I’m living the life I want. This feels great!“

Same with confidence. You could be as confident as anybody in the world as long as you don’t disrespect and look down on others.


One of the values you seem to live by is a world of extraction or minimalism as opposed to adding more in. The reason I bring it up is because you wrote a blog not long ago that said the adding mindset is deeply ingrained. It’s easy to think I need something else. It’s hard to look instead at what to remove.

We quite often quote Bruce Lee, who said, ”It’s not the daily increase, but the daily decrease. Hack away at the unessential.“

In your world, with your standard operating procedures, what have you hacked away at and/or removed from your world in recent times which had a profound impact on you, your life, your family, your world, your health. Is there something you have removed and taken out that’s made a difference?


Let’s look at productivity, for example, trying to get more done in one day. People often comb the Internet looking for productivity hacks, looking for things they can do to be more productive and I’ve done that, too. Over and over again, I have to catch myself when I realize I’m trying to add some new morning routine, or add some new way of thinking, or add some new technique to get things done better. But actually, why am I doing any of this?

This entire project, or this whole secondary thing I’m doing, it’s pretty secondary, isn’t it? Maybe instead of trying to get more productive at doing this thing, I should just say sorry, ”I’m not going to do this anymore.“ Why did I agree to this? It’s more of a constant reminder that the solution to things is not just always adding more things. You have to question when you find yourself trying to find a new way to do such and such.

Even the whole idea of, ”I need to find a new way, or a new approach, or a new philosophy, or another book, or whatever.“ For example, books. Sometimes what you need the most is to stop reading new books.

If you’re thinking there’s some kind of information you need, if you’re looking out there thinking, ”I need another book,“ maybe try to stop reading new books for a year. Go back through the ones you’ve read in the past and try to apply what you’ve already learned. All this information that’s sitting in your head unused, try to apply that or let go of more of your goals.

Here’s a huge one. You asked for an example. Just a month ago, I gave away all my musical instruments. I have officially closed that chapter in my life.

I am no longer making music, and it’s because every day I was looking at that piano over there, and those two guitars hanging up on the wall, kind of kicking myself for not putting aside time to make music like I know I want to. I’d say, ”Gotta get better at stopping my writing earlier and setting aside time. Or I need to work on this before I start my day with the other stuff because it’s just not happening otherwise.“

I was kicking myself daily thinking, ”How can I make more time to make music? This is something I really want to do.“ Then I looked at it again and I thought, ”Or, maybe it’s time to just let go of that goal. Something we never talk about is letting go of goals as a good thing. We often talk about goals as if they are something that must be achieved, do or die. Once you’ve set a goal, you must find out how to achieve it.

But the last few years, over and over again, I’ve been looking at old goals that I set. Things that I really felt like I must achieve. I’ve been looking at it going, “Huh, or not. I could let go of this entire thing. Would that be so bad?”

So I did a thought experiment with myself about getting rid of all my musical instruments and letting go of that part of my life completely. I was surprised that the thought didn’t horrify me. It’d actually be kind of nice. I’m living in Oxford, England, now and a friend of mine here is a full-time professional musician.

I called him up. I said, “Tom, it’s your lucky day [laughter]. You know that guitar of mine you love? It’s yours. It’s your lucky day. Have it.”


[Laughter] It’s your lucky day!


Tom goes, ”Oh my god, dude! I was just thinking about buying that keyboard because I like yours so much!“

I said, ”Well, it’s yours now. In fact, do you want these speakers, too?“

He said, ”Hell yeah!“

So I just gave him everything. I thought, ”Well, if I’m not using my room as a recording studio, I don’t need these nice big speakers either.“ It was so liberating.

I got rid of all that stuff and now I’m just monomaniacal [laughter]. I’m completely focused on my one single goal and I’ve just let go of all my secondary goals.


Earlier in the show, you told the story of the pig farm and the guy said, ”Hey, do you want this gig? It’s 25 bucks.“ You went, ”Hell yeah!“

You’ve become known as the ”hell yeah or no guy.“ It’s such a simplistic but profound way to go about thinking and making decisions. We had Jason J. Redman on the show, who is a former US Navy SEAL. He was shot in the face in Afghanistan very, very badly.

There’s a famous sign that he hung on his door, and it said something like, ”Don’t enter this room with sympathy. I did what I wanted for a country I love for a job I love.“ He wrote this story, which became very famous because one of the US presidents saw the sign and went to visit him in the hospital. He became the ”overcome guy.“

During the show, he said there are times when he catches himself and he wants to give in, or not do something, or take the easy way. Then he goes, ”Whoa hang on a second. I’m the ’overcome guy.’ All these people look up to me. I have this identity. I can’t let them down if I let myself down.“

Being the ”hell yeah or no guy,“ does that identity ever play in your decision making?


Again, I need to answer this sideways. It helps that I’m not that famous. It’s not like I’m going on TV every day being the ”hell yeah or no guy,” but even if I was, it’s more interesting to look at the things that you might even consider the absolute core of who you are and keep questioning those things and be ready to let go of them.

Because there are some things that we decided as teenagers and think, “This is who I am,” and here we are 15 years later in your 30’s, still being that guy because you decided as a teenager that this is who you are.

You need to be willing to look at any of these things and try letting go of them and doing the opposite, or just saying, “OK well that that was a goal or even a persona I adopted years ago and maybe I don’t need it anymore. Maybe that goal, or that persona, or that approach got me through that time in my life.

Times change and people change and I think it’s more important to constantly look at where you’re at now. What your current goals are now and who you need to be, or who you are now. Either who you are now and what beliefs you need to get you to where you want to be, or you know who you need to be now to get where you want to be. Acknowledge that those goals change.

There’s a wonderful book by Marshall Goldsmith called, What Got You Here Won’t Get You There. It was written to successful business executives, and its core idea was that the collection of tools that got you from nothing to being the head of a successful company are different tools than you need to now get to the next level. To get to a certain level of success, you have to be selfish. You have to focus more on yourself than others.

Not for everybody, but for some people. Being selfish can work well to get you to a certain height. Goldsmith said to get to the next level in your career, you need to reverse that. Now you need to stop being the way you’ve been for decades and flip it around and be more focused on others. Be more of a team player and be more of a listener than a talker. For example, even in relationships, or let’s say romance, love, whatever you want to call that stuff [laughter].

There might be a certain way you need to be to find the person that you want to be with. Once you find that person and you’re in a relationship, there’s a different way of being that you need to be now. You need to close that toolbox and put it away and open up a new toolbox that you’ve never used before in order to stay in the relationship and make it a great relationship.

It’s a whole different set of tools. So now, going back to your question, do I feel the need to be the ”hell you no guy“ or does it shape my decisions? Hell no. Absolutely not [laughter].

I welcome myself or allow myself to completely sluff off anything I’ve done or said in the past because that was then, and this is now.


I’ve heard you talk about the saying ”Easy choices, hard life. Hard choices, easy life.“ – which I think ties into what we’ve been the last few minutes –

Do you still agree with that today? If you do, do you have an actual example of a hard choice that you have made recently that led you to have an easier life?


That version of that quote doesn’t work as well for me as the version that says, ”Is this what you want now, or what you want most?“ I think of it that way. Easy choices, hard life – that to me means easy present, hard future, but hard present, easy future.

That way of thinking about it works better for me. At any given moment, maybe five or ten times a day, I’m tempted to go do the easy thing. To stop writing my book and relax. Call a friend or go eat a donut [laughter]. Then I catch myself going, ”OK, what do I want? That’s what I want now. What do I want most? What I want most, is to finish this book.“

I stand up, crack my knuckles, sit down again, and keep writing. That’s one version. I also had this long-term goal of wanting to be more of a world citizen. A lot of us Americans get trapped into feeling that America is the whole world. Yes, we know there are some other little countries out there and they have very nice little Eiffel Towers and Sydney Opera houses, but this is the only real country [laughter].

A lot of Americans really feel that way. Whether they say it that way or not, being surrounded by Hollywood and the media that we’re surrounded by, it can really feel like America is the whole world. I shook myself out of that about the age of 40 after selling my company.

I thought, ”God, there’s a really big world out there. I don’t want to just see it as a visitor. I want to integrate. I want to freely attach myself to different parts of the world and feel it in my soul.“

That involves being uncomfortable in the present moment to be comfortable in the long term. There’s a specific example I can point to that I think back to when I was 20 years old and I moved to New York City.

Coming from a little suburban town in Illinois and moving to New York City, especially back in 1990, was more overwhelming than now. I actually found out very recently that the year I moved to New York City, crime was at an all-time high. It has never been that high before or since, and that’s the year I moved to New York. It was a really scary place. You really felt on edge walking through New York City.

It felt dangerous and coming from my safe little suburban upbringing, it was a scary place to move to. It was very uncomfortable. But within two years of meeting people, making friends, going to events in people’s houses and parties around the city, pretty soon the whole city was my comfort zone.

Everywhere in New York City felt like, “This is my city. I know this well. This is my home. This is my comfort zone.” I look back and think, “How cool is that? I went to this place that terrified me and now it’s comfortable.

How cool would it be to do that over and over again? To look at whatever place scares me and go there and stay until it becomes comfortable? Like Rio de Janeiro? That place scares me. It’s terrifying. How cool would that be to move to Rio and stay there a couple of years until it actually feels like home? Until I know this city inside out. All my friends are here. I speak perfect Portuguese. Cool. Now let’s move to Beijing and do it again. Now let’s move to Ulaanbaatar, Mongolia.”

How cool would that be as a life compass or playbook? Go wherever scares you and stay until it’s comfortable. By the end of your life, you can look at the globe of the world and spin the globe and every place could feel like home. You’ve got a circle of friends in all these places. That’s a really cool idea.

Even if you don’t feel like traveling the world, if that idea sounds kind of nice, but you don’t want to live in Ulaanbaatar, you can apply it metaphorically. You can look at what in your life scares you. What ideas or what approaches to life scare you? Look at your various goals in life and ask which one scares me the most? That could be the one that you should be aiming towards. Because then you get that transformational thing of whatever scares you, go do it and soon, it doesn’t scare you anymore.


What’s really interesting about your world, Derek, is that you said you prefer talking on the phone to hanging out with people in person. We’ve talked about it and you’re well known for your love of music and your history in music. You built a business on music.

You actually said you love voices, but then you hate noise because you don’t like crowds, cities, bars, parties, streets because they’re too noisy and you can’t pick out one voice from another.

When I read that, it seems you have a very strong auditory sense in that tone and sound is terribly important for you as a learning tool. Are you big on audiobooks? Because people quite often say, “Well, I don’t really enjoy reading books,” in which case they back out of learning at all. But they haven’t thought about their own preferences for how they learn best.

It seems you’re very auditory and even when you tell stories, you tell with this melodic tone. Is your learning style – when you are taking in information – is it an auditory sense? Is that your strongest sense?


[Laughter] That was a sweet question, thank you.


[Laughter] But no?


But no. Let’s just say for heart stuff, I’m more auditory. For head stuff, I like text. Meaning, I like books. In fact, I actually prefer e-books now because I have my whole system with everything I’m reading. I take notes on books and I save clippings from them as text files. I put it into a database and I review it. I’ve got a whole system for taking in information and retaining it. Because of that, nonfiction audiobooks don’t work for me.

But yes, if I’m going to read a novel, then I’d rather it be audio. I don’t really listen to podcasts because anything I listen to feels quite fleeting. It kind of goes in one ear and out the other. Maybe a little bit of it sticks, but it’s too ephemeral to me.

Whereas if I really want to integrate something into my life, I really want to have it in text because I’m just a computer nerd. I’m a programmer. I’m sitting on the command line all day. If something’s not in text form on my computer, it feels gone. Even if I do listen to a podcast and learn something interesting from it, I have to immediately go to the computer and write it down in text. Otherwise, it’s just gone.


That’s really interesting. I wonder if there’s something in there with learning styles, which I’ve never, ever heard spoken about. Depending on the situation, and particularly when emotions come into it, whether you tend to favor a different learning style.

For you, if it’s something emotional, you want to have the conversation, it’ll be auditory. If you are processing something technical or it’s a learning environment, you prefer something in a written sense, which is more visual. Interesting. I wonder if there’s something in that.


My friends and I don’t text each other. We don’t email each other. We just call. At best, maybe my friends will text to ask if I’m free, and then I say, “Yeah, call me.” I don’t want to communicate by text. To me, that’s for information. That’s not an emotional connection.

It’s funny, I haven’t really tried video courses very much. When people put together a really good, multimedia presentation where you’re watching a course, not a TED talk where you just look at somebody standing and talking, I hate those [laughter]. But the ones where somebody puts together something really visual and can show mathematical concepts in visual terms.

That might be a really interesting way to learn math, for example. If somebody could show it to you, so it’s not just an abstract concept, but something you could see and go, “Ahh yeah, that makes more sense.”

I haven’t really experimented with that much, but that would be interesting.


At the head of the show, you mentioned the word “still,” then I read that you said you thrive in solitude. What does solitude bring to you that you so greatly desire?


A lack of friction. I think of obstacles. Obstacles to my concentration and obstacles to my productivity.

In fact, I was thinking once about what home means to me. To me, home is the place without obstacles. That home is a place where I don’t even have to think about my surroundings, I can focus on whatever I’m doing with zero obstacles.

That is what I want from home. Home is the place without obstacles.

Solitude is the place where I can just do what I’m doing. Think what I’m thinking, be lost in thought, or be lost in output, productivity, creating, and writing. Thinking without any friction of having to interact with other people in the community, or be understood, be considerate, or empathetic.

I have that sensitivity where even if somebody else is in the room, or even in the building with me, I’m too aware of their presence, and I feel a need to be considerate. Part of my brain is being used up on my thoughts of whether I’m being a good companion or host.

I don’t want to think about any of that. In fact, this makes me sound a little crazy, but I actually tried having a dog earlier this year. In theory, I wanted a dog. I love dogs and I love other people’s dogs.

In theory, I really want to have a dog, so I got a dog.

[Laughter] I just found that part of me was missing the solitude. Even though it’s just a dog. Part of my brain was always wanting to make sure that he’s happy. I thought, “I hope he’s alright. I hope he’s not too bored. I wonder if he needs something more from me right now. Am I exercising him? I can’t do this.” Part of my brain was always trying to make my dog happy.

My mom loved my dog so much. It was her dream dog. She was thinking of getting the exact same one. So I said, “Here, just take mine,” so my mom adopted my dog, and god, I love it so much more now. I mean, I always loved him, but solitude is so crucial. I really love around 12 hours per day of alone time. That’s when I get everything done.

Once somebody else is around, whether it’s a part of me or all of me, is just focused on the other person.


You just mentioned home, which is actually really interesting because you said that home can be that place without friction. Yet when you actually look at where you traveled, you spent a few years in a number of places: Singapore, India, Belgium, New Zealand, England, Portugal, and you don’t just go there to visit. You go there to become either a legal resident or a citizen of those places.

Yet you said each one feels like home in a way because you like to slowly expand your sense of home. So home must be a little more than just a place with no friction where you can create and feel comfortable. There must be something else that that environment brings to your sense of what home means, and how it’s different from what we commonly think of what home is.


It fits in with my New York City story earlier where I want to take things that used to be uncomfortable and make them comfortable. You could do it with your physical environment – that’s almost too obvious. You can rent a tiny crappy little apartment and then change it until it’s the way you like it. OK. Now, there’s no breeze blowing through that window. I fixed the radiator so it’s not making that clanging noise, whatever it may be.

Then, emotionally or intellectually, there are places that seem confusing at first. When I first moved to Singapore, I was coming out of my time at CD Baby in the music business. I’d meet a lot of Singaporeans that would say, “Oh, I used to make music, but my parents really wanted me to be a lawyer, so I stopped making music and I’m just a lawyer now.”

I’d say, “No! That is so wrong. You must follow your dreams. It doesn’t matter what they want. It matters what you want. You’ve got to follow your individual passion in the world!” I really felt this for probably my first six to nine months. I really felt like they were wrong and I was right.

Then it took me a while to really get to know my Singaporean friends and spend some time there listening instead of talking before I finally understood the mindset of this Confucian style of thinking, which is: What you want is a fleeting thing that shouldn’t be heated. You do what’s best for the group. The group meaning your immediate family, or your neighborhood, or your extended family, or your country. You do what’s best for the group and that is what’s right.

To me, it almost felt like meditation. When you’re meditating, you have thoughts that come into your head and you just let them go right back out again. You just say, “Oh, that’s just a thought. Let it go,” and you stay still.

The Confucian and therefore, Singaporean mindset that took me a while to understand is that these passions, these things you want to do, they can come in and they can go right back out again, like passing thoughts.

Ultimately what’s most important is doing what’s best for the group. Now, I don’t think that’s wrong anymore. I understand it’s just a different way of looking at something. Now I have comfort in that mindset or in that culture, and it’s no longer an obstacle to my tranquility [laughter].


Your zen [laughter].


I don’t get upset anymore. That’s me expanding my sense of home. So now Singapore is also my comfort zone. I’m legally a permanent resident of Singapore. I own a home in Singapore. It’s my comfort zone. I still have more friends in Singapore than hardly anywhere else and I love it. I’m very, very comfortable in Singapore.

How cool is that? I got to expand my definition. Ultimately, I’d like to keep doing that and make new places home and expand the places that are home, which to me means no obstacles.


So our show is all about the guests, but we also love our music.

Robbo and I used to work in a rock radio station together, so that’s important. At the start of the show, you combined a number of things that are right up Robbo’s laneway. You mentioned Prince, Miles Davis, Bowie. You tell stories of Brian Eno, who worked with Talking Heads, and Bono, and U2. You mention some of our favorite artists that we play here in the studio.

If I could play a song that when I listen to the lyrics, it represents Derek Sivers as a person, as a man, what song would I play?


I’ve never been into lyrics. It’s funny, some of my favorite songs that I’ve listened to 100 times for years, I still don’t know what the lyrics are.

There was some Björk song that I’ve loved for 20 years, and I’ve listened to it so many times. I just ran across the lyrics to it online and I went, “Whoa. What? Really? I had no idea!”

The relationship that a musician has to music can sometimes be kind of twisted. In the same way that a programmer looks at computer code.

Now I’m quoting The Matrix twice [laughter]. Remember in the Matrix where the guy sitting in front of the screen with all the little green symbols going across? He goes, “You know, I just see a woman in a red dress.”

When I look at computer code, because I’m a programmer, I can look at this stuff and it’s like, “OK, it makes sense. I see what they’re doing here.” Whereas somebody else would just look at that screen full of symbols. Music is a bit like that, too.

I’ve learned almost too much about music theory. Often what I love about music can be interesting little nuances about what they’re doing with the way they arranged a chord. For example, they’re spreading out the voices instead of doing a tight cluster, or vice versa, or the way they’re layering the rhythms.

My favorite thing in music is the combination of instruments and how the arranger or the producer combines instruments. I’m never so interested in an instrument on its own. If somebody is strumming a guitar and singing, I’m not interested.

On the other hand, if you’re combining a flute with a harp and a bass in some way that I’ve never heard before, now you got my attention. I love the combination of instruments that I’ve never heard before.


Well, let me throw this at you then, because this year, coming from a rock and roll background, I truly discovered jazz. I’ve always had it on in the background, but this year, I really focused on it and for a myriad of reasons, I discovered a love of jazz.

One of the artists you mentioned at the beginning of the show is a guy called Miles Davis. If there was a track of his that made you stop and go, “Wow!” Would you be able to put your finger on it?


I’m playing it with my hand, but what is it called? All Blues? I think it’s track four or five from the album Kind of Blue.




Bill Evans starts out with piano. I’m doing this with my hand. [Plays music in the background.] You hear this?


It’s beautiful. You’re absolutely right. It’s a great track.

Speaking of audiobooks, I just listened to my first audiobook in a year or two, which was Miles Davis’s autobiography.

I just finished that last week.




Speaking of music, it’s funny if you go to a jazz club and you’re sitting there with a few other people that understand jazz, the person can be onstage soloing and suddenly they may play something where two people in the club will laugh at once because they get the inside joke of what that musician just did. The rest of the audience didn’t get it, but two people in the room got that joke.

I feel a little bit like that. Especially when it comes to music production, too. In the song Closer by Nine Inch Nails, I love the fact that as soon as the track starts, there’s a little digital glitching underneath. It’s a sizzle.


Oh really? I’ve never heard that.


Check it out. The sizzle starts at the beginning, as soon as the kick and the snare come in, there’s a sizzle underneath and it stays there almost for the first minute of the song. Suddenly when it gets to the, “Help me,” part, the sizzle disappears.


Is it like a distorted kick and snare? Like they’ve copied and distorted it, or is it actually a digital glitch?


It’s a sizzle. It’s like the sound of bacon on a frying pan, but it’s very subtle. As soon as the lyrics go, “Help me,” the sizzle stops and its absence is delicious. I love those little tiny music production things!


So Derek Sivers, don’t tell me you’re not auditory [laughter]. To pick up a little sizzle in there, don’t ever say, “No man, I’m not auditory.”


This is what happens when you put two audio guys in the room and see where the conversation goes.


This stuff is so much more interesting to me than the lyrics. I don’t care about lyrics, but the nuances of music...


I’m with you.


In fact, as long as we’re on the subject. I’ll tell one other tiny story. When I bought my apartment in Singapore, I talked to a friend of mine who’s an interior designer. I said, “You know what? You’re my oldest friend. Have a go at it. Why don’t you go design my new home.” So she went into the place and did a whole bunch of visual things to it that she felt were right.

Then I moved in. I spent my first night there, and everything she did visually was moot because the windows were really noisy [laughter].

I thought, “Wait! No. The sound is all off!” She got so mad at me because I replaced her fancy little boutique windows with soundproof windows.

She said, “But it looks horrible,” and I said, “But it sounds great.”


I’m not going to spend time going through what you’re well known for, which has been well covered in different shows – about the directives that you have written for how we should approach our life. Just to finish off, what I’d be really interested in knowing is, what’s the directive that you think is the most misunderstood, yet if people embraced it, would probably have one of the most profound impacts on them as people?


I’m biased to the one that’s on my mind a lot. You know what? I have to give the meta answer to this. I recently found out that “meta” is the Greek word for “about”. I never knew that. I just took meta for granted, so I’m going to talk about that subject.

We often ask a stranger, “What book do you think I should read or what’s something you would tell your younger self?” It’s a type of question that assumes there is the best answer for everybody. But I don’t think there is one bit of wisdom that I think the world should know because everybody’s in a different place, at a different time.

It comes back to something I said an hour ago about letting go of your old goals and even your old persona, your old beliefs, things that you might have formed years ago, maybe because of the circumstances at the time, and now you’re still holding onto it because you’ve defined that this is who you are.

I think we need to acknowledge that those things change, that we need different tools for different times, different beliefs, for different phases in our life. We need to let go of the old ones, even let go of goals that aren’t serving us.

So I don’t think there is one thing for everybody unless you want to count that as my meta thing about letting go of old beliefs, old goals, and constantly questioning them and letting yourself slough them off and walk away from them with no loyalty to your previous proclamations.

Even if you’ve announced it to the whole world, “This is who I am and this is what I believe!” – if you are in a different phase now and change your mind, you should loudly say, “I’ve changed my mind.”

I don’t know why people don’t do that more often. We feel like we need to be consistent for some stupid reason. We need to be loyal to what we’ve said in the past. I’m constantly disloyal to everything I’ve ever said and done.


Derek, I’ve been looking forward to this for – it’s fair to say. . .


Gary you’ve been talking about it for years. Let’s be honest.




We made it happen. You’ve been very, very gracious with your time. We have gone way over. But honestly, I’ve got another page of stuff that I wanted to ask you about, but I’m very conscious of your time and how you allocate it. I know that you are very precise about what you do. I’ve never had anybody send me an outline of topics to discuss that directly relate back to Mojo.

Honestly, it’s uncommon. So we started the show with common versus uncommon. Having you as a guest and how you approach it, Derek, is uncommon. It’s such a privilege, and an honor to spend time with you because I know how precious it is, and how you allocate your time, and how you think about what you want now versus what you want most. So thank you, mate. It was fantastic.


Yeah, I really like hearing from strangers around the world. It’s actually part of why I do what I do, and part of why I do podcasts. I think it can be a little beacon to hear from kindreds around the world. So anybody who listened all the way to the end of this show, please send me an email and introduce yourself.


That would be everybody [laughter].


So how do they find you, Derek? The people who want to speak to you. Find out more about you. Find the directives. You’ve got some new books that you’re about to release into the world. Where is the hub for Derek Sivers?


You know the answer, don’t you? [Laughter]. is my site and my email address is there in a big font. I don’t hide it.

I actually really, really do like hearing from people that introduce themselves and just say hello. Go to my site, say hello, it’s all there.


Well, thank you. We’d like to extend an invitation to you that when you decide to add Australia to Singapore, India, Belgium, England, Portugal and so on, when you finally decide to come and spend some time here and call Australia home for a while, we promise we will record live with you on Bondi Beach in front of the famous Bondi Lifesavers Tower.




We’ll have tea, or coffee, or beers, or. . .


Beers and fish and chips.


I almost moved there instead of New Zealand when I was living in Singapore and deciding what to do next. It actually looked at Bondi Beach.

It actually came down to that or New Zealand. I chose New Zealand, but I am now a New Zealand citizen, so I have a legal right to live in Australia.


Yeah, New Zealand is a special kind of place. Let’s be honest.


Yeah, it’s wonderful.


That was cool. Worth a six-year wait.


The thing I’ve been pondering over the break is the discipline to take the things that these guys talk about, or the discipline to take the stuff that you read about in your book and then apply it.

The big thing I’m hearing from people like Derek, or Tim Ferriss, or the Jacko’s, the Leif’s, Pat McNamara, the difference with those guys versus the rest is consistency. Derek does his thing. I’ve been following him for almost a decade and he is consistently showing up. He’s got his rules. He knows what he wants to do. He’s very, very intentional.

Something Colin Wright talked about in the show is that he’s very intentional with what he wants to do. That’s something you’ll hear Ryan Hawk, from the Learning Leader Show, on our show, talk about a lot – being very intentional and then doing it consistently.

The issue today is people start off really good, they fall off the wagon, off the path, and think, “I gotta get back on the path!” They do it again for a week and then fall back off. I really admire guys like Derek because he is consistently intentional. Year after year after year, I thought he was great.


OK, I hear what you’re saying and that certainly rings true about getting on the horse and falling off. You deal with people one-on-one, on a daily basis who are trying to stay on the horse. Give us some tips. What do we do? How do we stay on the horse?


You build your rituals, you build your routines – the way you start your day. You are very intentional about having your day planned. You know what’s important in your day. You know what your priorities are. You limit your distractions. You get to the end of the day and you review your day. The night before, you plan for the following day and if you’re going to do it, get it done and limit distractions.

The people who say, “Ah, I’ve got so much to do,” but spend an hour watching YouTube and spend a half an hour down the rabbit hole in their socials, or by doing something that’s inconsequential to them that just wastes time. The consistency is how you allocate your day. You do it the night before. You’re very intentional. You’re focused around what’s important to you, what has to get done as a priority in all areas of your life.

If you go back to your book review, look at your priorities the night before and plan. Where’s my reading time? Where’s my thinking time? Where’s my family time? Where’s my me-time? If it’s playing with the dog, if it’s work in a particular project.

You block out all other things and get them done and compartmentalize. We’ve got a few guys coming up on the show that are going to talk through this. The famous David Allen who wrote Getting Things Done. Thirty years, he’s at the top of his game about planning. A guy called Charlie Gilkey wrote a book called Start Finishing. It’s an excellent book about how you actually finish. Because we start a lot of things, but then we don’t finish. So build your rituals, build your routines, be intentional, plan the night before, limit the distractions. When you’re focusing, just do that. At the end of the day, review what you’ve done. Do what Christian Boucousis talked about – what did I set out to achieve? What happened? What was the reason? What will I do differently?

As Charlie Gilkey talks about in his book, we don’t need an accountability partner to eat ice cream, but we need an accountability partner to keep us on track for these things because we lack discipline, we lack planning and intentionality. That leads to us having a lack of focus and a lack of consistency. So I think these are all things we’re talking about, and a lot of people do these things, but a lot more people don’t.


Yeah, there you go. A few plans of action there.