You Can Too
host: James Brackin
self-identity, journaling, entrepreneurship
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Transcript:
James
Welcome back to the You Can Too podcast. On today’s show, we have Derek Sivers, formerly a musician, TEDx speaker, circus clown programmer. He sold his first company for $22 million, gave all of his money to charity. We have the pop philosopher himself, Derek Sivers. Thank you so much for being here.
Derek Sivers
Thanks, James. I really like your podcast and I admire what you’re doing.
James
The best words that I can hear from someone I admire so, so much. Derek you’ve been in this space for a very long time and not only just the business space, but the entrepreneurial space, the belief space. And I’m so excited to dive into your new book. But starting at a young age, what was the belief or the story that you told yourself that served you well?
Derek Sivers
Starting when I was a little kid. When I was five, we moved to England for a year. So I was born in California. But when we moved to England, that’s when it became really clear like, I’m not one of you people. You guys have a some different beliefs that I don’t subscribe to. So you do your thing, I’ll do mine. There was this I’m not from here kind of feeling right. But then I moved back to America when I was six. We moved to Chicago where I had never lived, and everybody called me the English kid because I had picked up the accent. And most of these kids had never left Illinois. So now I felt, “Well, I’m not from here either.” So that I’m not from here thing stayed with me all the way through my childhood. And then in my teenage years I was already dead set on being a musician, but I was surrounded by people that were talking about getting into a good college and getting a good job. So once again, this feeling of like, I’m not from here. Like mentally, I’m not one of you people was strengthened even more because it felt like what most people are pursuing in life is not what I’m pursuing. And I still feel that I’m 53 now and it still feels like what most people are pursuing. Whether it’s safety or security or ego boost or all these things that it feels like most people are pursuing, those are not my pursuits. So I think this has stayed kind of constant from age five till present.
James
Yeah. And your slow living is something I, again, I admire so much in the way that you live your life and the way that you prioritize your time and what you do with your time. It doesn’t matter what anyone else’s expectations about you. You do what you feel, do what you should do. And I admire that so much because we have so many external perspectives that we feel we should go a certain way. And at 14 you got into music, 16 it was where you really decided that was going to be the thing for you. How do you think more people can discover that intuition within themselves? Because I felt that as well with what I’m doing. It was like I was different. There’s a pole here. I know that it’s different than when most people are doing, but I think a lot of people don’t trust that intuition when it first arrives for them.
Derek Sivers
Maybe it’s the fear of sticking out. Maybe in my weird case. I got that out of the way at age five, I had already stuck out. It was too late. I was going to be the weirdo regardless. So maybe for people listening to this, you have to reframe sticking out as a benefit, not a downside. You see this in the creative fields, in music, in art. It’s more clear there that if you come on to the scene doing something radically different, that’s to your credit. That’s what will help you get known as an artist, as a musician, as whatever is to be radically different. But I think all of us can apply that approach to our life. No matter what field you’re in, even if you’re in-- I don’t know. You’re in sales, you’re in manufacturing, you’re in something that sounds generic like that. It’s sticking out. That’s the smart strategy. Yeah, that’s what Seth Godin’s book called The Purple Cow was about. That it’s best to stick out in a field full of cows. You want to be the purple one, not the normal one. So I think it’s a smart strategy in any endeavor.
James
I believe that as well. I’ve lived by the mentality that I don’t remember who brought it up to me young. But this perspective that there’s only one of you, right? Like no one can replicate what we can bring. Even if we had a twin, they still can’t replicate this exact what we can bring to the world. And so it’s almost like we’re doing a disservice in the world by not bringing our unique perspective and the thoughts that we have and the way that we live our life, because there’s going to be someone that resonates and there’s going to be a lot more than one person that resonates the more that you do it. I know your son’s 11 and now he’s he’s at a point where he wants to step into entrepreneurship and he has an amazing role model in this space. What would you say for someone that’s starting to step into entrepreneurship or struggling even just already in it?
Derek Sivers
Ooh. It’s funny. He only told me this last week. I guess you saw my now page. So everybody listening. If you have your own personal website, you should put a page on it called “Now” that just kind of says what you’re up to now in case people ask. So yeah, if you go to sive.rs/now, that’s my now page always saying what I’m up to. So James saw that just last week. My kid came home excited from school saying they’re studying entrepreneurship. And he says, “It’s the first time I’m actually into what we’re doing at school because I can use it in the real world.” And it’s funny, I’ve told him since he was like three years old. You have to master something. I don’t care what it is. It could be drawing. It could be Rubik’s Cube, it could be violin, it could be ostrich farming. I don’t care. Whatever it is. But you’ve got to master something. And so last week, he came home and he told me this and he said, “You know how you said, I always have to master something?” I said, “Yeah.” He said, “Can I master money?” I went, “Yes, you can. That would be pretty damn worthy thing to do.” Okay.
Derek Sivers
So with that context, my advice for people is to definitely read a lot of books. I mean, it’s amazing how much of the world’s wisdom has been compiled into these $10 books. Okay, maybe they’re $14 books, but no offense to all the video vloggers and YouTubers out there, but Youtube and blogs have a lot of noise. There’s a lot of hidden incentives to get clicks and views and to be sensational and to get people sticking around past that ten minute mark for advertising. But a book is about the last format that’s not pummeled with advertising or whose incentives are not swayed by advertising. So I really find much, much, much better value from books than from random articles and YouTube videos that a lot of people go to. So it’s like, that’s my first bit of advice, is find the great books on entrepreneurship and really ingest their wisdom. Okay. But the main thing so that’s like that’s number two. Number one, the most important thing is then to take all of these ideas that you’re reading about and hearing about and actually go try them. You have to just get into a mindset of this constant churn of trying everything, about having zero concern if it fails. To just get into this mindset that you’re like, “Let’s see what happens if I do this, let’s see what happens if I do that. Let’s try this, let’s try that.”
Derek Sivers
And if you just get into this flow of trying lots and lots and lots of things. It’s like the metaphor of a lottery ticket. Now it’s dumb to play the lottery. Anybody you know, doing Statistics 101 knows that, but the metaphor works because the more lottery tickets you buy, the more likely you are to hit the jackpot. And so it’s like that with entrepreneurship. You just got to go try lots of stuff. Don’t go banking on one precious idea that you think, “I’ve got a billion idea. If only somebody will listen to it.” It’s like, no, you’ve just got to try lots of stuff. You never know what’s going to work. You don’t know what the public will want. So just go try lots and lots of things and lots of approaches to a single thing that you’re doing. Even if you’ve got just one business that you’re focused on, go try every little marketing approach that you’ve heard about. Go try crazy, weird things. You just never know what’s going to work. That’s my main advice.
James
It’s so, so powerful. The most concise way that I can explain it, is that volume negates luck. The more the more action that you take the more likely you’re going to get lucky in life. And that’s really kind of what it comes down to. But I think there’s so many points that I can touch on here, and I want to touch on a part that I think I heard you and Tim Ferriss speaking about. And it’s the difference between maximizing and satisficing and finding like a balance between that. How do you know what to go all in on, how to maximize and then also what to allow things to just be okay at.
Derek Sivers
I think we all probably have an inherent value system that you care so deeply about some things that you can’t just slough it off and care half ass. Say, for example, for me, it’s like the quality of my writing. Absolutely. I can speak like this somewhat carelessly, but when I put things into writing, I love to chisel and polish every word. Like, dude James, one minute ago, when he just said volume negates luck. Like my inner writer went, “Ooh, that’s good. That’s succinct. That’s nice.” Volume negates luck. If you came up with it, man that’s a good one anyway. So I definitely maximize my effort on writing, and I know that I’m not being efficient about it, but this is something I care so deeply about that I’m going to nerd out on it in an irrational way. But I think for everything else, you have to remind yourself why you’re really doing this right? I’ll just pick a dumb example. Some people nerd out about like traveling with frequent flyer miles and the credit card rewards and they try to get the best possible deal and they end up getting like 12 different credit cards and passing the balance back and forth between them. And they get into this obsession with trying to get the best possible deal. And I think somewhere in there you have to ask yourself like, wait, why am I doing this? To get frequent flyer points? Why do I want frequent flyer points to travel? How much is your time worth? How much are you spending on this? Like, shouldn’t you perhaps just book a cheaper economy flight and go somewhere instead of spending all this time opening 12 credit card accounts? So that’s an example where you have to ask yourself why you’re really doing what you’re doing. Remember the real point. And then most importantly, just go right to the point. Just go draw a straight line from where you are to your destination. And go directly there without all the crap in between. Yeah.
James
As you were speaking about all of that, I think there’s a point where your writing is simple to read, which means it was hard to write and for you to take How to Live from 1300 words to 112. Blows me away.
Derek Sivers
Sorry pages not words. 1300 pages down to 112 pages. Yeah.
James
The fact that you were able to break that down into almost every single word needs to be there. How were you able to distill your thoughts so clearly? And then how would other people even start to be able to do that?
Derek Sivers
Oh, well, first, I don’t know if that’s important to other people. So again, somebody listening to this writing succinctly might not be your top priority. And that’s okay. You don’t have to. Yeah, in fact, you could even argue that if you’re too succinct, it can be a little off putting. It can be almost like poetry, where people really have to slow down and go, “Whoa, hold on. Tell me those three words again.” You know, volume negates luck. Okay. I need to think about that for a second. Whereas somebody who’s more verbose and conversational. Right. Might actually be a more effective communicator. So first, I don’t think everybody should try hard to be so succinct. That said, if you’re just asking how I did it. Just a lot of sweat and caffeine. I just sat there chiseling away at these ideas, going, no, I want to make it shorter. I don’t want to release a 1300 page book. Yeah, I want to get these ideas from my brain to yours in a way that’s more enticing, that’s more appealing. A 112 page book is not intimidating. I like that. I like little books that are unintimidating. Yeah, I like that. Most of my books can be read in about an hour, so that’s just my value system for what I was doing for that project. If I was just writing something else or giving a talk to an audience. I wouldn’t be so succinct.
James
Yeah, I ask because it’s prolific to see and to read and it doesn’t matter where you’re from or what year you’re in, you’re still able to read that. It’s like just another book, right? Like it’s normal. And your ability to be able to do that is prolific and I know “Useful Not True” is coming soon. And I am so excited for this and I would love for you to dive into the four main areas.
Derek Sivers
Yeah, this seems to be right up your alley. So, yeah, let’s talk about this. Ask me anything. It’s a fun subject.
James
What are the the four main areas that you touch on so far that you have for it?
Derek Sivers
Actually, do you have them? They’re on my now page, aren’t they? Do you have them in front of you? Could you read them out. I don’t have them off the top of my head. Yeah.
James
Number one is: Almost nothing is objectively true. Disprove limiting mindsets should we stop at that one.
Derek Sivers
Should we stop at that one and talk.
James
Yeah. Dive into it all. Yeah.
Derek Sivers
So I’d actually like to hear your take on this because some people have emailed me. Objecting to this idea that almost nothing is true. And I think they have negative associations around some kind of US politics and politicians lying in denying things that actually happened. But I’m only talking about personal effectiveness. I’m talking about your belief system that most of us live in a social world, unless you’re a scientist working in a lab all day and you’re not doing anything social. But most of us live in a social lab of the world. Where people say things like, “You can’t do that.” Or maybe, “You better try something safer.” Or, “I’m just no good at this” Or, “There are no jobs here.” Or, “You need to apply in the line with everybody else.” Or, “That’s not the way it’s done here.” All day long we’re surrounded by thousands and thousands of things that people say as if they’re true. They say them like facts, like, here’s how to get a job here or here’s how to make it in this industry. Or here’s what you can’t do. Here’s what you can do.
Derek Sivers
And I think it’s so important to point out that none of those are true. None. Not a single thing that anybody says that subjective is actually true. If it can be, possibly disproven with a single case, well, then it’s no longer true. I put the bar of true all the way up to mean physically undeniable things, right? Like I’m standing on one foot right now as I talk to you. That’s true. New Zealand is a nice country, that’s subjective. That’s not necessarily true. Right? There are so many things, so I’d say. In our day to day lives almost nothing is absolutely true except for physical, provable facts. And the way I think of it right now is the things that both an octopus and a cat and an alien would all agree upon. Something that somebody from Mars could use their equipment and take a picture of it and send and agree with you. But all these things that are internal in our heads, these statements that people make, basically none of those are true unless it’s a physical fact. So first, I think it’s liberating. It’s emancipating. It’s empowering to realize that almost nothing is objectively true.
James
Yes. And I am in so full support of this this entire topic. When I came across it, knowing that you were writing about it, I was like, “I hope to write a book on this exact topic years from now because I would love to because I’m curious as well.” I think you’ve noticed it as well is no one really talks about like the ideas that are beliefs, we see them as concrete but they’re really just like malleable, just like our mind is. And so, yes, when we recognize that so much becomes possible. Like I think the big mindset shift for me growing up was I always believed that life was happening to me. I know you talk a lot about identity as well, and it’s like that was the frame of reference that I viewed life through. I lost a lot of family growing up. I had a lot of surgeries growing up. I almost died when I was born. There’s just like so many different things where I felt like life was just piling things on top of me. And I think Awaken the Giant Within was a big book that had a really massive impact on your life. Me as well. And I think there was a moment where he talked about the power of the questions that you ask yourself. And so there was a moment in my life when instead of asking, “Why is this happening to me?” I asked, “How is this happening for me?” And my life genuinely changed within a second because I asked a different question. And so it kind of comes down to the same thing with beliefs. It’s like we don’t question them and so they are true. But when we recognize that it’s all objective, that’s when things really start to become malleable and that’s when things really start to become possible in our lives.
Derek Sivers
Yeah. You just said it’s all objective. I think you mean subjective. Yes, yes, yes.
James
Yes, yes, yes subjective.
Derek Sivers
To be clear for the transcript.
James
Yeah. Yeah. But I think it’s really important to talk about this. But why now is this coming across to you that this is going to be the main objective that you want to speak on or write on?
Derek Sivers
It’s been underlying everything I’ve thought and written about for over ten years. And it was something I was constantly having to explain to people. Yeah, like when I would say, I choose to deliberately believe that I’m below average because I was reading a book, I don’t know, 15 years ago I was reading one of these psychology books where they said that whenever surveyed, 95% of people say that they are better than average drivers and 96% of people in a hospital say that they are in better than average health or in better health than most people in the hospital. 94% of whatever, anything, everybody thinks that they’re above average. So hearing that, I thought, well, then I think it makes more sense for me to assume that I’m below average. I often do these things to deliberately counterbalance a bias. So if I have a tendency to do something that’s wrong. To think something that’s wrong. Well, then I’ll deliberately counterbalance it by stacking up beliefs on the opposite side knowing that the ideal outcome is a more balanced view. But I don’t think that you can put just a little pebble on the other side of the scale to balance out a lifetime of bias. You need to stack a whole bunch of bricks on the other side and acknowledge the historical weight and subconscious influence of these biases. So I will deliberately stack beliefs on the other side of my bias. And then when people push back saying, “But that’s not true. It’s not true that you’re below average and everything.”
Derek Sivers
Then I say, “Well, it doesn’t matter that it’s true. It doesn’t. I mean, let’s not even think about whether it’s true or not. Just is this a useful belief to hold? And if it’s useful to me, then I’ll choose to believe it.” So this has been coming up again and again and again in everything I’ve written for ten years. And so finally, after finishing my last epic masterpiece that took me four years to write, I had that feeling of, “Oh, like I gave that everything I got. There’s nothing left to say, is there?” Then once again, people were pushing back on something and I was trying to explain, “No, it doesn’t matter if it’s true or not, it’s useful.” And I thought, “You know what? I need to write about this.” So this time I’m writing not from a place of having a lot of answers and a lot to say, but I decided to make it a curiosity project, a research project like I’ve held this gut level belief that I should follow what’s useful not true. Maybe it came from Tony Robbins. Maybe it came from who knows where, growing up in California. I don’t know. But maybe it came from my background of constantly feeling like I’m not like you people. I don’t know. But I decided to look into it more. So I’m looking into the history of skepticism and pragmatism and philosophers of old that have thought these things already and learning more about it so I can write about it.
James
Yeah, skepticism has been the thing that’s been most foundational in the past few years. That’s really changed a lot of things for you, right? I mean, I will be the first one to purchase that book, and I’m already on the email list, so I’m prepped for all of the incomings because I’m so excited for that day. I think this idea is something that’s really important to take into perspective. Is there a belief or a story that you’ve told yourself throughout your life that you feel has been foundational in your your evolution, would you say?
Derek Sivers
Well, maybe it goes back to that very first question you asked, like just feeling like what I’m pursuing is not what most people are pursuing. So therefore the usual rules don’t apply to me. Yeah, and that sounds so egotistical or something, but I think it’s healthy for all of us to think that. I think for all of us, the rules don’t necessarily apply to you. Yeah, that’s it. The word necessarily is important there. The rules don’t necessarily apply to you. It’s wise to understand why those rules are there, right. And their usefulness in maintaining an orderly society. But I think it’s also wise to realize that kind of like childhood games, those rules are just arbitrary. When you’re a little kid, you make up these games like, okay, “Now I’m going to put my hand on the couch and you have to run at me. But if I touch you first, then you’re out. But if I put my foot on this or if my fingers are crossed, then it doesn’t count.” And we make up these rules as kids and we know that we’re just making up rules to play with friends. But then people grow up and they wear suits and have mustaches and make these rules and we think, “Oh, well, now these are facts.” Somebody told us that these following 78 rules are applicable here and we act like they’re there absolute undeniable facts, laws of nature. These are not negotiable. These are the rules. But I think it’s really healthy to remember that somebody just made them up. They’re all arbitrary. They’re not laws of nature. You can change the rules. You can negotiate. You can ignore them. You can just say, “Actually, that’s not the game I’m playing. I’m playing a different game and make up a new one.”
James
Yeah, I think back to like when the chair that I’m sitting on right now was once not a thing. And so if it was once not a thing, then the thing that I’m thinking about doing, that people are telling me that is impossible. Well, it’s going to be impossible until it’s proven wrong. Right? So like you said, beliefs are placebos and it’s living through that lens that I think you always have to be in a constant state of questioning. And you do a lot of reflection. Like I think the ideology of “I don’t know” is something I practice a lot because whether overthinking was something I struggle with a lot growing up. And so I always felt like it was concrete, like what was going to happen in my future was concrete. It was going to happen. I had to overthink about this outcome. But as soon as I realized that I don’t really know what’s possible, I really don’t know what’s going to happen. I really don’t know if this is true. And it’s exactly what you’re saying here and it’s useful. It makes me feel safe like that pattern of overthinking makes me feel safe, even though it’s not objectively true, nor is it helpful. And so, yeah, choosing more beliefs that are actually helpful in that serve us, is the kind of path that you’re going down, which I find so admirable. And I’m so grateful that you’re putting this out here because there’s not many people that talk enough about this. And as soon as I came across this idea of the story that we tell ourselves and the beliefs that we have, and there wasn’t many people that were speaking about it, I thought, what are we doing here? Everyone’s living in through this lens of life that is not serving them. And it’s like, we need to break people out of this.
Derek Sivers
Yeah.
James
It is so powerful what you’re doing. And I feel a lot of us and even if we do get to the point where we can intellectually understand that it’s a belief that isn’t serving us, we still get trapped into that. So what is your actionable route passed into? Of course, you said it’s kind of like creating more proof, but what would that look like?
Derek Sivers
It helps for anybody to take time out to journal like whenever something’s going on in life that’s bothering you. You’re not feeling like you’re completely thriving. Number one, turn off the outside inputs, even just symbolically, like power your phone off all the way. You know, where you hold down the power button for a full five seconds off. Yes, maybe even if you know your laptop is still on Wi-Fi, well then go to that little broadband router in the closet and power it off. And just to feel that like, “Okay, I am disconnected now no matter what the media is saying.” Like my reality right here is just like, okay, the wind is blowing the trees, the rain is hitting the grass. Whatever’s going on right like this is what’s real. My butt’s on this seat. My feet are propped up on the table. And I’ve got this diary in my hand or this text document, whatever it is like. Okay. Starting from that. What’s the real problem here? Yeah. What do I really want? Why do I want that? What do I think I’m going to get from that? Is this the best approach to get it, you know? And at every point, no matter what you say. Then you take everything you say and you ask yourself, “Is that true? Can I disprove that?”
Derek Sivers
I don’t remember if it’s in one of my four bullet points that I put on my now page. But you’ve got to start with disbelieving yourself. Maybe you start by realizing that what other people say is not true. Yes, but then do the more difficult thing of realizing that even the things you say are not true. You might say, “I’m an introvert.” And you just take that as a fact. As if just saying like, I was born here and I’m an introvert. These are just facts. But actually it may just be that you don’t like crowds. And you hate boring conversations because you’ve got an active intellectual mind. Whenever six people get together, it’s just nothing but small talk. So maybe you’re not an introvert, you’re just smart and you don’t like small talk. That doesn’t mean you’re necessarily an introvert. You might love people. You might have been accidentally designing a life for yourself that’s avoiding people because you told yourself once you’re an introvert or somebody else told you that and you’re just holding it like a true fact. Or you might tell yourself like I’m not interested in-- I don’t know making money? I don’t know. Pick a different one. I’m not athletic. Let’s pick that one. You might think, “Well, I’m just not athletic.” But it’s like, that might not be true either.
Derek Sivers
There might be people who call themselves athletes right now that are really no different than you. And I don’t know, pick any number of things that you might be telling yourself, “I need to stay here in my hometown. I can’t move to France.” Yeah, it’s like, that’s not true. So it just helps to disbelieve everything you say to acknowledging that your subconscious might be saying these things and might even be arguing that they’re true. Whereas in fact, you don’t actually know that to be true. You can disprove it. So yeah. Then in your journal, just kind of look at your situation of what’s bothering you and try to scrape away all the cruft around it and just get to the real point of what you really want and what you’re really pursuing and ask yourself, “What’s a great way to get directly there?” It really helps to shut out the noise of the world and all the things people say to just completely disregard all of it and just think that everybody’s just spouting their stuff for attention, trying to get their clicks, trying to get social status among their peers. And a lot of it is just nonsense and noise. And so you can shut it all out and just think of what’s actually best for you.
James
Absolutely. You spend about an hour to three hours a day journaling?
Derek Sivers
Yeah, at least.
James
Doing doing that for such a extensive period of time because, I mean, you’re writing books, you’re keeping us posted on what you’re doing, even though you don’t stay on socials. It’s like, how is that relationship with your self built up knowing that you’ve taken a step back from what 99% of the population is on? Because I admire that so much.
Derek Sivers
I don’t know. Is 99% on social media and stuff?
James
I mean, of people that I speak to, I don’t know one person that other than you that is that is not on social media, to be completely honest.
Derek Sivers
Wow, that’s funny. A lot of my friends are much less, of course, online than me. Yeah, a lot of my friends not only do they have no social media, they also have no website. They just kind of live their lives and do their thing and they’re just kind of away from all of that. So, yeah, maybe these are the people I surround myself with, but it helps to be in a place where you’re connected with the real world. Like I could imagine if you just lived in an apartment in Singapore and everything around you is man made and everything is human construct. I think you could get into the mindset that the world is all human construct. It helps to get out into a place that’s just trees and dirt and oceans waves crashing on rocks and remind yourself like, this is the real world that this thing you’re like this thing that humans have made is just like the last five seconds on the clock of time. It’s a thing that came recently that will go away soon. That’s all ephemeral. And I don’t mean that in some kind of woe and death kind of way, but just like just realize how ephemeral all of this stuff is, that when people tell you in the media that this is important, imagine just saying like, “Okay, well, I’m busy right now. I’ll get back to this in five years.” And five years from now going, “Okay, what was that you were saying on that day in April, in 2023?” And they’ll go, “Oh, never mind. It wasn’t important.” Well, then why bother with it today if it’s not important in five years? It’s not actually important now.
James
Yeah, I love that perspective. I haven’t watched the news ever. I don’t think for that reason. It’s like a lot of that stuff is mostly negative and it’s just more input to the brain that you’re taking in the things that are actually helpful, as in your books, which I want to share with everyone.
Derek Sivers
Thanks.
James
I think it’s important to know what your inputs are so that what’s going on in your brain when you’re not thinking about what’s going on in your brain is serving you well. And you do that really well, I think through journaling so much. What’s something that you’ve learned about yourself that maybe you at first didn’t question? But throughout so much questioning you’ve realized wasn’t true?
Derek Sivers
For lack of creativity, I used one as an example five minutes ago. Where I’ve always called myself an introvert. And just a few months ago, I started questioning that. I went to India for just ten days. Sorry, ten days includes travel. I was there for seven days and had 52 hour long conversations in seven days. So basically 9 a.m. to 10 p.m. for seven straight days I had back to back conversations every day from 9 a.m. to 10 p.m., 13 hours a day. And loved it. I loved it. It was one of the best things I’ve ever done in my life. And most people I tell this to go like, “Oh, it sounds exhausting.” It’s like, “No, it was great.” You know, I’m not a fan of TEDx anymore, but ten years ago, like, I used to love watching those TEDx talks and this was like having my own personal TEDx. I was like an audience of one where I got to make the talks. I was sitting there meeting with like 50 really interesting, smart people, asking them whatever I wanted, and it was mostly about them. I was more of a listener than a talker and it was fascinating. And I got so much energy out of it, I thought, “Huh? So introvert. Huh? Maybe not. Where did I get on that idea?” And it’s like, maybe it’s just that I hate when people get together in groups of five or more and just start talking shallow nonsense, and I’m just like, “Ugh, get me out of here.”
Derek Sivers
I’d rather be home with a book. So maybe it was just because of that circumstance that I started thinking, I’m an introvert, but maybe that’s not true. Okay, so that’s one recent big one. But things come up all the time. Like even though I’m writing this book, I catch myself saying things like--. Just this morning before our interview, I was saying, “Well, I need a bank account.” And I thought, Well, do I actually need a bank account?” There’s a service called wise where it gives you like a kind of a virtual card account. It’s not officially a bank. It’s like, isn’t that sufficient? Yeah, I think that does everything I need. Maybe I don’t need a bank account, and I catch myself stating opinions as if facts. Like the city I’m in Wellington, New Zealand is not my favourite. It’s not the worst. It’s pretty good. But I catch myself saying bad things about it as if they are facts and then I have to catch myself going, “Wait. That’s not true.” I mean, I could argue the other way, couldn’t I? Somebody could argue the other way. And if somebody could rightfully argue the other way, well, then it’s no longer true. So, yeah, maybe I should shut up about that. Maybe I should stop saying that these things come up all the time.
James
I love the way you think. And just hearing your experience with talking with that many people and thinking you’re an introvert. And because I think the same thing, like small talk, that kind of stuff, that’s the last place I want to be. But these interviews, I could do these all day. You know what I mean? Like, it’s such a different perspective. And if we don’t question it, then we’re going to live through that paradigm. And as you said, you went there, but you’ve been around a lot. What’s something that travel has taught you not only about the world, but about yourself?
Derek Sivers
A lot of the subjects that we’ve been talking here came from my travels. And not just traveling. Not just, you know, taking a picture of the Colosseum, but getting to know other cultures. Living in Singapore, living in Belgium, living in India, living in Portugal. You get to know people that have a very different outlook on life that you do and again, have some core foundational beliefs that go against your core foundational beliefs, which then make you realize that what you thought were just true because you foundationally believed them. You realize that’s just one way of looking at it. So I think that’s the biggest benefit of travel, is realizing that all these things you thought of as true were actually just one perspective.
James
I love that perspective as well. You’re someone that’s very introspective and you’re a deep thinker and there’s so much that you’ve built that is just-- it’s amazing to see, but I feel like I want to know where did you start? Whether it was your books, your everything that you’re doing. Like I think of your books right now, like where did the first thought of stepping into this space even come from for you and how were you able to actualize it, if that makes sense?
Derek Sivers
Books, you mean? Or like this kind of pop philosophy stuff we’re talking.
James
I mean, both, really. It’s kind of like the identity that you’ve taken on almost, right?
Derek Sivers
I mean, books in particular. I never intended to write a book. People asked me for years if I would write a book. I said, “Nah, I’m happy just doing blog posts.” But then Seth Godin asked me to write a book. He said, “I’m starting a publishing company and I want you to be my first author.” So I said, “Okay.” And that was that. Then people really liked my first book, so I kept making them. Also, I just realized that thing I said earlier where I don’t like ingesting content from YouTube and clicking and clicking and clicking articles, I really like to lay down on the couch with a book. And I thought, “Well, in that case, why am I saying that I don’t want to make one of these things that I like so much?” So now I flipped on that. I realize I’d rather make books. I’d rather make a damn good book every year. Than generate a lot of shallow content elsewhere. Okay, so that’s one thing. But everything else I think is just personal effectiveness being who you want to be, being a better version of yourself than you thought you could be. That’s always mixed into whatever we’re pursuing, right? So even all those years, I spent 15 years as a full time musician. And then another ten years speaking to full time musicians, because I was running a music distribution company, I was serving musicians. So for 25 years of my life, I was in music and talking with musicians.
Derek Sivers
And so much of that is a mental game. Whether it’s the actual creation of music and the beliefs that go around the creativity we talked about. Standing out instead of fitting in is essential. If you want to make it as a musician, you don’t want to fit in. You want to stand out, call attention to yourself. Then there’s the whole mentality of calling attention to yourself. And then that leads into a mentality of marketing, thinking of marketing, marketing as another term for being considerate, if the best marketing should be being considerate. And then that’s a mindset of looking at things from the other person’s point of view and your self-identity of how you see yourself in the world. Yeah, whether you’re pursuing music or business or who knows what this. The psychology controls everything. Your mindset controls everything. So I found myself speaking a lot about the mindset stuff. At first speaking only to musicians. And then it was kind of weird to me. I guess it happened accidentally because I started speaking at the Ted conference. And so then I started getting random biologists and, I don’t know, forestry investors telling me they liked my writing. And I thought, “Oh, I don’t know anything about you people, but thank you.” So now I guess most of my writing is about that general stuff about mindsets.
James
How were you able to not disassociate, but almost like step into that identity of I’m a writer, I’m an author now because going through like you said, you were in that space for such a long time. I feel a lot of people say it’s a sport, for example, that’s their existence. And that’s why, like I think Tom Brady couldn’t retire until he had to get so many different Super Bowls. I’m a Steelers fan, so it was disappointing to see. But like, he did it because that was his identity. He seen himself as a football player. I mean, not like secondary to a father and all of that kind of stuff, but like, how were you able to shift your identity?
Derek Sivers
Oh, man, I’ve had to do it a few times. Yeah. That’s a lot of reflection. It’s a lot of work to think of yourself in a different way. But honestly, I think it’s one of the most fun exciting things you could ever do in life is to change your self-identity. Again, I said that one little example earlier where it’s like somebody who always thought I’m not athletic. And to get to the point of realizing like if you just show up at the gym for X number of days for say, 45 minutes a day for a number of days, and you do a few of these things, well then you’re athletic. Now you fit the criteria. And that can be the same with anything. You know, I’m not an investor. That’s not me. That’s what rich people wearing ties do. And, you know, hey, just read this book and do what it says and move some money from here to there, even if it’s $100. And guess what? You’re an investor now. This applies to so many things in life. Self-identity can really change everything. I’ll tell you something sad I’ve never talked about publicly. One of my favorite people in the whole world has such a terrible self-identity that she keeps herself in prison. With a co-dependent family. She’s one of the smartest, most interesting and loving and wonderful people I’ve ever met.
Derek Sivers
And she lives in East California. And she just has this self-identity that just tells herself like, “Well, this is just my lot in life. My mother needs me to be here. She calls me five times a day and just needs things from me. So I have to be here. I’m just not the kind of person that travels. I just don’t do that.” And it’s so frustrating for me as somebody that cares about her so much that all it takes, you know, you click and you book a ticket. There you go. Now you’re a world traveler because you clicked that button. You moved a little bit of money from your credit card into Delta’s account. And now you’re a world traveler. Self-identity can change with just a couple clicks. You just take a couple actions and then you have to show yourself like, “Well, I took this action, so therefore my previous self-identity has been disproven.” Yeah, but some people just won’t. And they just don’t because they tell themselves, “I’m just not that kind of person. That’s just not me.” And so I think it’s just one of the most limiting beliefs that anybody can have that can just keep them from having a wonderful life. Is this sad belief of like, “Well, that’s just not me.”
James
Yeah. That’s why I’m so grateful for all of your work and and the new book and everything, because it’s going to change so many people’s lives. Just the concept in itself, like the fact that we have an identity. And I don’t remember exactly who it was some philosopher but, “You’re under no obligation to be who you were five minutes ago.” I don’t remember who it was exactly. Maybe it was Alan Watts or someone. But taking on that perspective is so foundational. It goes back to like what I said earlier is, I changed the question I asked myself and it changed the direction of my life, genuinely changing the question. And so when you change the way that you look at yourself by providing new truth, as you’re saying, is you just take a few actions and you’ll realize that it’s possible. But we’re just stuck in this box that we place ourselves in. You’re someone that future proofs themselves very well. Like you’re living for your future self, almost like you’re doing the work for that person. How have you been able to find the. I don’t like to use the word balance, but almost like a harmony of setting your future self up for success while also being present and enjoying where you are?
Derek Sivers
Haha I don’t balance those very well. I live almost entirely in the future in my head. It’s funny. So like we said, my kid is 11 and his mom sometimes says to me like “God, I can’t believe he’s 11.” And she means that like in her head he’s a little baby. Yeah. And the funny thing is I’m like, “God, I can’t believe he’s only 11.” Like, in my head. He’s 20, he’s off into the world because that’s where my plans are. That’s where my focus is. So as of now. I think the main thing I do to be present, honestly, is just my time with him. He’s just at that age still where-- God just realizing it might not be this way soon. He’s still at this age where just everything is massively present, focused, right? Like we’re just fully engaged in whether it’s Lego or Frisbee or building a fort in the forest or racing leaves down a creek or whatever. I just spend a ton of time with him, just fully engaged. Just let him lead the way the whole way. So I just have to let go of me entirely, right? Like, my ego is just parked back at the laptop when I closed the lid and power down.
Derek Sivers
Now I’m just like his follower, right? His playmate. And he leads the way and I just follow. So that’s my main way of staying completely present. I would have even said walking in nature. I do take long walks in the forest. I live right next to a forest, so I take long walks in the forest for almost two hours a day. But I’ll admit, James, like a lot of those times, I’m walking in the forest, my head is running through all of my projects and things that I’m planning and doing. So yeah, I think we don’t have to balance it. You know, anybody listening to this, if you love living in the future, if that’s what excites you, that’s what you should do more of. I think that using that compass of what excites you and what drains you. Is the ultimate life compass because that’s a life well lived. If your whole life you kept pursuing what was exciting you the most, even if later it turned out to be not the wisest strategy to meet your ultimate goals, it wasn’t optimum. That’s fine. If you were excited and having fun, that’s a good life. So use that compass.
James
Yeah. How do you keep it fun? I think that’s the path of sustaining in it for so long and that’s why you’re able to do what you do now is you’ve made it fun almost, right? It was a part of it?
Derek Sivers
Let me think. Yeah, I guess if you just pursue what excites you the most. And is something absolutely necessary to be done. And not only do you strongly dislike it. But you can’t even find anything interesting about it. Well, then see if you can stop doing that, whether it outsourcing it to somebody else or just shutting down that side of your life and saying, you know what, I don’t need to be everything to everybody. I don’t need to keep a perfectly clean bedroom. I’m just not going to clean my bedroom. Never mind. There’s only two of us here. I’m the only one that sees it. Fuck it. Just let it go. I’m more excited to do other things, whatever it may be. Mowing the lawn, you know? Hopefully you can find a way to get excited about those necessary things. Like I think if I had to mow the lawn every week, if I lived in a place that had a lot of grass, I would make the best of it by putting on a podcast like yours and just engaging my mind in something while my feet were just moving in a pattern until I noticed that the lawn was all cut. You could do things to that that don’t excite you like that if they need to be done. But otherwise I think it’s it’s best to just keep steering your life towards whatever excites you most.
James
Absolutely. And with everything that you talk about, there’s like this idea of saying no to so many things. So you can say yes to the one big thing.
Derek Sivers
Exactly.
James
How do you--
Derek Sivers
Yeah go ahead. Go ahead.
James
How do you get clear on what that yes is? Like, I feel a lot of people are out of touch with their intuition. You do a lot of journaling and questioning, but how were you able to figure out what that yes is for you so that you can say no to everything else?
Derek Sivers
Well, I think that doesn’t take introspection. It’s supposed to pound you over the head. There’s that thing that only comes along. It might only be every few years when something comes along and makes you go like, “Whoa, Oh, my God, yes! Whoa, This is what I want. That would be amazing. Oh, my God.” When something makes you feel that way, then you throw yourself entirely into that thing. So my message that I was trying to get across with Hell Yeah or No, which was first a little article and then a longer book. The whole point of Hell Yeah or No is to deliberately leave empty space in your life. Don’t fill it with all of these like, “I’m not really sure. How do I know if this is my yes or not?” It’s like, well then just know. If you’re not sure, then just know. Leave emptiness in your life. Leave empty space because sometimes occasionally, even if every few years something’s going to come along that excites you. And then because you left space in your life, you can throw yourself entirely into this thing. Whereas if you just filled up your life with lots of little tiny projects and obligations and little crap that you’re doing, well, then something amazing comes along and you’ll look at it and you go, “Oh yeah, that looks exciting. But I just can’t. I got this, I got that, I got this, I got that. There’s just no way I could.” And you’re going to miss out on that amazing thing because you filled your life with this and then that and this and then that. So, yeah, leave space. Just emptiness. Leave time in your life. Say no to almost everything. Just read books and walk in nature and play with your kid and chill so that when the big thing comes along, you have space and time in your life to throw yourself into it all the way.
James
Yeah, the way that you live your life and like just diving into your work. I want to emulate that so much. And just the way the way that you think, the things that you put out, like everything that you do, I admire so much. And as I said earlier in this podcast, I think questions are something that’s really important. And with you doing so much journaling and reflection and introspection, I’m curious, like if you had to have a sticky note by your bedside table and had to be a question that you read every single morning, what would that question be?
Derek Sivers
Oh, sorry. I’m in the phase of writing Useful Not True right. Now so first thing I thought of is, “Is that really true?” Could you imagine you wake up first thing you see is like, “Is that really true?” No, actually. I’ll give a longer lasting answer. On my book list. And I don’t mean my books. I mean the books I’ve read. If you go to my website, it’s sive.rs/book. There you will find a list of almost 400 books that I’ve read in the last 15 years, and my detailed notes on each one and sorted with my highest recommendations at the top of the list. The books that I think everybody should read. And near the top of that list is a book called “Almost Perfect” by an acrobat named Erika LeMay. And she talks about her morning routine. Every morning she goes to write to her notebook and reminds herself what she’s doing today. Like, what’s the real goal? What is she after in life? And she said almost every morning it’s the exact same thing. And she said, “I just write it to myself every morning as a reminder. I’m here to be the best acrobat in the world. I’m here to express beauty through movement. I’m here to be world renowned, whatever it may be.” She writes it to herself every morning as soon as she wakes up to remind herself like, okay, what am I doing? This is what I’m doing. So that’s a pretty good one. In that case, I guess the post-it note by the bed would say, What am I really doing?
James
I really like that answer because I think a lot of us are going through life through the motions, not questioning enough what we want to do, what kind of life that we want to live. Right.
Derek Sivers
Yeah, you’re right. Yeah.
James
Which is why I admire so much of what you’ve been able to do. Because it’s something I’m trying to get better at. I walk a lot as well. And I think for people that are listening, they probably know me as the person that posts on my story every day going to walk because it’s been so foundational for me growing up. It was something that I didn’t really like, didn’t realize consciously how much of an impact it had on my introspection and the thoughts that I was thinking and the life that I was like creating in my mind of what I wanted. And it’s so impactful to do that kind of stuff. And there’s one question I ask every single guest. The last question I ask, and it kind of encapsulates what I’m trying to do with the podcast is unlearning versus learning. I think we have to unlearn a lot more than we need to learn. To be honest, at least from what I’ve been able to experience. And I want to know, what belief are you currently unlearning?
Derek Sivers
Not a belief, but another self-identity. For the last 15 years since I sold my company. I’ve said that I have no interest in making money. That been there, done that, got plenty. I’m done. Done with that game, playing a different game and just ten days ago, sparked by that thing we said of my kid coming home from school, being excited about his entrepreneurship class. I started rereading some books on making money. I went back to Rich Dad, Poor Dad by Robert Kiyosaki, which is not a great book, but has a great mindset in it. Definitely. And just the past ten days getting excited about the subject again. I think it’s fun. If you think of money as a neutral transfer of value that people just use it to say, “This is valuable to me.” So I’m going to take some of these digits and send them over here because it’s giving me this value in return. Well, then pursuing making money is really just pursuing being valuable to others because it’s all social. I think I’ve spent the last 15 years focused on being valuable to myself, more than valuable to others. So maybe this is just a little bit of rebalancing. And who knows? If you ask me again in a week, I might not be interested in this subject anymore. But hey, you’re asking me today. So you get today’s answer, which is right now I’m unlearning the self-identity that I have no interest in making money.
James
Prolific and you definitely are giving value to the world. It’s just not the intention through the lens that you see it through. You’ve provided so much value to me and everyone that’s listening to this podcast right now and everyone that’s purchased any of your books or read any of your stuff, I’m so thankful for you and everything that you’ve put into this world. Thank you so much for coming on the show Derek, you are an absolute legend.
Derek Sivers
Thanks, James. And hey, anybody listening to this, please? I actually really enjoy hearing from strangers. It’s one of my favorite things. Once a day for about an hour or two, I go to my inbox and see which strangers have said hello and I reply to every single email. So if you’re listening to James’s podcast, go to my website and send a little hello, introduce yourself.
James
Absolutely. And it’ll definitely be in the show notes as well. Thank you so much, Derek.
Derek Sivers
Thanks, James.