What Got You There
host: Sean DeLaney
mastery, writing process, impact of quotes, beliefs exploration, personal utopia in business
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Transcript:
Sean
Derek welcome. Welcome. How are you doing today?
Derek Sivers
Sean, it’s nice to finally talk with you.
Sean
I know I was saying, six years in the making. Well worth the wait because of the impact that your ideas, your thinking, your books, your writing have had on me. So I’m truly grateful for this opportunity. But you know what, Derek? This makes me actually want to start here, that this is actually probably my favorite quote of yours. So I went through a ton of my notes, my private notes I have on you, recap stuff like that. And it’s this, “Mastery is the best goal because the rich can’t buy it, the impatient can’t rush it, the privileged can’t inherit it, and nobody can steal it. You can only earn it through hard work. Mastery is the ultimate status.” That’s what I love.
Derek Sivers
I love it too. I know we’re not supposed to admit a love for our own work. You know, it’s like the cultural norm, as we’re supposed to take a compliment and say, oh, well, that’s nothing, you know? But, oh, my God, that book, How to Live, that you’re quoting from. I am so damn proud of that book. It’s like my favorite book ever written, and I’m the guy that wrote it. I’m not supposed to admit that, but it’s true.
Sean
How do you gauge your work, that internal compass you have around this thing that I put out in the world, this was truly remarkable. I appreciate this. This lived up to my standards. I’m just wondering how you gauge the work you put out in the world.
Derek Sivers
I don’t know, I don’t know if we ask ourselves that when we listen to a song we love or watch a movie we love. It’s just like you hear a song and you go, “Oh my God, I love that song.” You listen to it ten times in a row and you go, “I still love this song.” And for whatever reason, it just works for you. There’s like something in your values or your preferences or your gut that just loves that song. And so I do remember that feeling as a musician sometimes. Well, usually I would create the songs that I wished would exist but did not exist yet. I’d say I wish there was a song that had this kind of like drum to it, but this kind of melody to it, but this kind of syncopation to it. And I’d go make that song that I wished would exist. And when I did it, I’d say, “Damn, I love this song.” And it’s because I made the song that I wanted to exist, you know? And so now I’ve done that with my most recent book, “How to Live”. It’s the densest book I’ve ever read, or the densest book I’ve ever known. Like, every word needs to be there. I guess you could say, like a book of poetry would be like that, right? But I just put everything I had into that one little book, and I’m so happy with it.
Sean
You even go further on what that means for you to put everything that you have into that book.
Derek Sivers
That book in particular. I tried to make it the culmination of everything I’ve ever learned. But if any of us were to do that, of course. I mean, oh my God, how do you put everything you’ve ever learned into one book. Right. Well, I tried to do it. And the rough draft was 1300 pages long, but I did not want to subject the world to a 1300 page book. So then my next job was for the next two years, basically full time for two years. I edited that 1300 pages down to 112, and I replaced entire pages with a single sentence like, you know what? When it really comes down to it, this sentence can represent everything I was trying to say with that whole page. You’ll have to read it slowly and think about it. But yeah, that one sentence represents that whole page. But now every sentence that you see in the existing book represents what used to be a page. So yeah, it’s everything I’ve ever learned put into one book. And compressed with a trash compactor.
Sean
Well, let’s explore. Your writing process in the path to mastery, and let’s say you’re on that path. I’m wondering for you what is important for me to understand about the path to mastery for you?
Derek Sivers
Well for me. And let’s take me out of that question. The path to mastery, I think it helps you slough off the noise. It’s almost like it doesn’t matter what you choose to master. You could decide to become a master at ping pong or Chinese poetry or archery. It doesn’t matter what it is. But when you get on that path to mastery and you say, this is what I want, I want to become great at this. This is what I’m doing. Then all the other noise that comes at your eyeballs and ears through the media. Or even just chatter from friends. You now know that it’s all just noise because you know what you want. It really helps you filter the world, and I think that’s its biggest benefit. Or maybe I should say that’s its secondary benefit. Its primary benefit is the deep happiness you get from making yourself proud. Like if you set out to do something and you achieve it. To me, that’s the deepest, deepest happiness. That’s my definition of success, is just achieving what you set out to do. Doesn’t matter what the rest of the world thinks of it. It doesn’t matter if you made a single dollar from it. To me, success is just achieving what you set out to do. So that’s the main benefit of mastery, but I love the secondary benefit of helping you shut out the noise. Since you know what your big yes is, then you know that everything else is a no.
Sean
Derek, when you were describing that, where did you go? Your eyes, they lit up in a different way than they had been the first few minutes.
Derek Sivers
I was thinking about my ten year high school reunion. Where I always knew what I wanted. Since I was 14, I decided I wanted to be a successful musician. And I was surrounded by other teenagers in high school that I thought also had a thing that they wanted. They had a passion, I thought so. Maybe I wasn’t analyzing it too deeply, because when I went to my ten year high school reunion. It was just a bunch of sad, fat people working in middle management positions at some dumb company. Looking really old at the age of 28, they looked 40 and they seemed pretty miserable. And I was just a full time touring musician at the time. Like I was just touring the country, playing music, and I stopped by my high school reunion in Hinsdale, Illinois, outside of Chicago and everybody commented like, “Oh my God, it’s so great that you’re still doing music, that you’re still doing what you want.” I thought, “Well, of course, like what? What are you people doing?” And then I realized in hindsight that they didn’t really know what they wanted. And then I get emails from strangers around the world that are like, “I don’t know what I want.” And I think that the biggest benefit of that path of mastery is that thing. Again, it doesn’t matter what it is, you can pursue anything, but by pursuing something you’re able to know what you want and stay focused and tune out the rest of the noise. That makes people kind of undecided and miserable. Adrift.
Sean
Yeah adrift. Did you know at 14 internally that this is truly what you wanted? I’m just wondering about how you become suddenly attuned to that inner knowing.
Derek Sivers
Actually, let me take it back. 14 is when I started playing guitar. 16 is when I knew. Yeah, I want this. I want to be a successful musician.
Sean
What changed in those two years?
Derek Sivers
Oh, just getting better and better at guitar and then probably getting the social rewards from people around me saying, “Dude, you’re awesome.” And you get a couple of years of that and you think, “I like this. This is working for me.” So I didn’t know what successful musician meant. It definitely didn’t mean mean making $1 million or being a rock star. That was one possible option. It might have even just been being a great guitarist that’s a guitar teacher, or something like that. That would have been still within my definition of success. But I knew that this is what I wanted. Like I became very monomaniacal, a word I learned recently monomaniac mono meaning one. You focus on one thing, you go maniacal for one thing. And so I was a monomaniac on music for 15 years, from the age of 14-ish till 29.
Sean
You think passion has to be a factor on that path to mastery?
Derek Sivers
Cal Newport has a brilliant book called “So Good They Can’t Ignore You”. And in that book, he makes a wonderful point that passion is the emotion that comes later, after you’ve started getting good and getting rewarded at something. You have to first start by just doing the thing even before you feel passionate about it. And then when the world starts rewarding you. And by the world, I don’t necessarily mean other people, I just mean once you start getting rewarded for pursuing something on that path of mastery. Then you start to feel passion about it. And he has a bunch of wonderful examples about this. And the one off the top of my head is that he said Steve Jobs was not passionate about computers. He was passionate about, I think, yoga and meditation. But then on the side, his friend Steve Wozniak said, “Hey, look, there’s this opportunity here we can make computers.” And Steve Jobs looked at it and said, “I think we could sell them too.” And he just started doing this thing on the side. It wasn’t his passion. But after that thing with Steve Wozniak he was doing started rewarding him it became the passion. I think that’s a great thing we should remember. If you’re not feeling passionate about something, if you’re just sitting there watching TV or listening to too many podcasts and thinking about, “I don’t know what my passion is.” It’s like, well, you can just pick something and start and just go down that path. And the feeling of passion comes later.
Sean
You were mentioning around your book, “How to Live”. The way you thought about this was the same as the way that you thought about new songs that you’d put out into the world, is you want to hear what you hadn’t heard before. And this makes me think about something you wrote around starting your company, CD Baby. And I had never thought about entrepreneurship or running a business like this. And you say, “You create your own utopia when you make a business.” It’s a little universe, I think you said, and you create the laws and I would love for you just to expand on this, because for me, as an early entrepreneur, years ago, when I first read that it was eye opening, I thought about a problem we had to solve and everything, and I forgot that I was creating a universe and I could change things to make that universe more magical. And for me, it was one of those moments where it’s ahh. The way I think about company building is forever changed because of this. And I would love for you just to expand on this.
Derek Sivers
Cool. That’s really nice to hear that my little book had that impact. To me, it was always just a given. It’s like you go into another business and you don’t like the way they’re doing things. So you say, “All right, well, in my business, here’s how things are going to go.” And I just got an email yesterday from a woman who’s thinking about doing a week long meditation retreat or some kind of retreat. Maybe it’s like a health and wellness retreat and was asking my advice and I said, “Go to 3 or 4 other health and wellness retreats. And ones that you think are pretty similar to what you want to do, and you’ll find a whole bunch of stuff you don’t like, and you can vow to be the opposite of those things. And you’ll pick up a couple of tips you do like too.” But I love that feeling of negative motivation of witnessing something you dislike. To me gives me a creative spark to to go right that wrong to say, “All right, well in my company we are going to always answer the phone right away. None of this layers of voicemail routing crap. And in my company, anybody who wants a refund gets a refund. And in my company, no paid placement.” It’s never fair for the people with more money to be able to buy up spots on the front page, and in my company--, you know, so just all of these kinds of personal utopian plans to right the wrongs of the world. To me, that’s my biggest motivation for making a company.
Sean
Talk about other motivations right now. I know you and I happen to both be fascinated on a similar theme, actually, and that’s around beliefs. And I didn’t know until recently just how interested in your new book that’s going to be coming out later this year is on this. And just dive further into beliefs and your current thinking. And there is a lot I want to explore with you.
Derek Sivers
Sure. Yeah. I’ll start out by just giving a quick little seed of it and then let’s talk more about it. “Useful Not True” is something I’ve been saying for years and years and years. I first noticed it in my diary like ten years ago, because there are many things in the way that I am choosing to think I’m choosing this belief because it’s a compensation for my tendency to go the other way. Right. So if I had a tendency to think that men and women are very different, and a lot of people have that, especially people who went to like an all one gender school, you know, if you go to an all girls school, then you think men are weird. Men are this. And if all of your friends are guys, you think women are weird. They’re so different. But actually, I think the differences among men and among women are much greater than the differences between men and women. So if you notice that you have a tendency to be thinking one way, you have a bias. Well, then, a good way to counteract that bias is to deliberately choose a belief that will counterbalance it. So I would deliberately choose a belief like men and women are the same. Exactly the same. And I would share that belief with somebody and they’d say, “But that’s not true. I’d say, “It doesn’t matter if it’s true.” It’s useful for me to believe this because it counterbalances something else, I think.
Derek Sivers
Or maybe if you’re starting a new venture and you need courage to help you take that first step. It helps you to believe that this is going to be great, that this is going to go well, that the world wants this, and a grumpy little Eeyore could come along and say, “Well, you know that’s not true. Nobody wants this.” You could say, “I don’t care if it’s not true. It’s useful. It’s useful for me to believe that people want this. Because if I don’t believe that, I won’t take any action at all.” And let’s do one more in the category of self fulfilling beliefs. If you’re put into a social situation, some party or some event, let’s say, where you don’t know anybody. If you believed that nobody here will like you, well then you’ll just sit in the corner by the punch and eat cookies and go home early and not talk to anybody. But if you believe that this room is full of fascinating people that are your future friends. Then you’ll go talk to people in an outgoing and interested way and make friends. And so then it’s a self-fulfilling belief. But somebody could of course point out, “But that’s not true. All these people are not interesting, and they’re not going to all be your friends.” You say, “I don’t care. It doesn’t matter if it’s true. It’s useful for me to believe this.” So over and over and over again, I noticed that I had this common thread of I don’t care if it’s not true, it’s useful. This is a useful belief.
Derek Sivers
And after I finished the How to Live book, I thought, “Okay, now I’ve got some time to explore this.” So I contacted one of my favorite philosophy writers, a woman named Sharon Kay, at University of Ohio is one of the clearest writers I’ve ever read on philosophy. And I said, “Okay, can I describe this useful not true thing? Some philosopher in the past must have thought of this already, right?” And she said, “Actually, it sounds a lot like pragmatism. You should look into pragmatism.” So she directed me towards four books, and I ended up reading like seven books on the subject of pragmatism. And it’s a little bit pragmatism, but first and foremost, it’s skepticism. It’s starting out by saying, almost nothing is true. Even whether somebody says, everybody in this room will like you or nobody in this room will like you, none of those are true. Optimists and pessimists are both not true. Anything that’s just a conjuring of the human mind is not true. To me, the definition of true is like there, my hand is hitting the table right now. That’s true. Anything short of that. Anything that’s not a physical, concrete reality that an amoeba or a spider or an alien would agree upon. There’s just a kind of workings of the human mind, and I think we should not call those things true. So if they’re not true, well, then everything’s up for grabs, and we can just decide what’s useful for us to believe. Sorry, I thought that description was going to be shorter.
Sean
This is wonderful. I’m wondering for you, how do you start uncovering what beliefs you want to go with? Or are you that clear in the moment at this point? Or you take some initial groundwork?
Derek Sivers
Yeah, I think it’s just a constant discovery about yourself when you notice that you’re holding a belief that isn’t working for you. Then you should question it. See if you can expire it or counteract it. For example, even though I’ve been thinking this stuff for ten years and working on this book for a year, off and on now, so far, just a few weeks ago, I caught myself saying that the city I live in right now, Wellington, New Zealand. I caught myself saying and thinking that this is a bad place to be. This is not good for such and such. And I’ve been saying that for years. And only a couple of weeks ago I went, “Oh, wait a minute. That’s not true, is it? I’m writing this book about how all these things for the mind are not true. This isn’t true. Wellington’s a fine place for such and such.’ Or I don’t even need to say another not true. Like Wellington’s a fine place for this. I just have to notice that this subjective thing I’ve been saying is not true. And once I realize it’s not true, it becomes this wonderful neutral that I can decide, what would be more useful for me to believe?
Sean
Let’s think if we’re building a house here, constructing a house, any foundational beliefs that essentially guide everything else?
Derek Sivers
No, I think it’s all just for the moment. There are times in your life where you need to have a foundational belief that everything’s going to be great. And there are other times in your life. Say before beginning a two week long camping trip. Where it would really help to have a foundational belief that many things could go wrong so I should prepare for them now. Do you know what I mean? We shouldn’t even be thinking in these religious type terms that want to have a single, monist, sorry, monist like monotheist belief that there is one truth, that there is one way. I think you should always realize that all of our beliefs, even the ones that feel like religion are actually just useful beliefs for us for now. And we should feel free to expire them if they’re no longer working for us.
Sean
What part of writing this new book has gotten you to pause the most? And I don’t know if that happens for you.
Derek Sivers
How do you mean pause?
Sean
Derek, you seem to have incredible internal awareness. Even back to your story at 14, I think you’re able to listen to things internally that most people pass by on the surface. And so when you hit either a roadblock or even the way I view it, almost like a cascading river that’s flowing really quickly, I think you’re subtly attuned to those. And I’m wondering when you’re on that flowing river, meaning everything’s pouring out. You feel like what you’re putting down in your book is incredibly helpful for you and for other people. I’m wondering if is there’s anything where you’ve stopped and almost looked at it from the side and been like, “Wow, that’s really interesting.” Meaning it made you pause.
Derek Sivers
Ahhh. Hmmm.
Sean
I’m glad you asked me to elaborate on that, because the initial just pause question.
Derek Sivers
Wow. That’s interesting. Pause. I think the fact that most people I think have a natural internal pull towards a need to believe that there is one truth, that there is one correct diet, that there is one correct way that our culture should be. That there is one correct spiritual belief. There’s one correct way to be approaching your life and business or parenting or whatever it may be. But yeah, that pull towards religion. I think of it as a pull towards religion. It’s a pull towards wanting a doctrine that’s a congruent top to bottom, “This is correct doctrine” I think is harmful. Because it’s like delegating our thinking to someone else. It’s like trying to subscribe. It’s like choosing a membership program that you want to subscribe to instead of picking and choosing. I think that it can be useful. A congruent top to bottom lifestyle philosophy. Or I should say, a lifestyle built around a congruent philosophy or religion can be really useful to bring you peace of mind. Social harmony. If you’re in a place where the people around you believe the same thing. But I think a lot of people are also harmed by this because they are following beliefs that their parents told them. For example, your parents said, “Never trust anybody. People that look like this are out to get you. Don’t go there. Those people want to harm you.”
Derek Sivers
And we listen to these things as if it’s like our Bible, you know, to go, “Oh, yeah, okay.” You internalize that stuff. And then you realize in your life that it’s working against you, that you’re not going places because you assume that people there don’t like you, and you’re not having open conversations with people because you assume that they are people you won’t like because they look so different. And it takes a while to realize how these things are working against you. And where those beliefs came from, and it’s time to expire those beliefs because they’re working against you. So to me, this “Useful Not True” book that I’m working on or idea that I’m diving into, the most pausing well aspect of it has been realizing how emancipating it is. That if you can choose your beliefs piecemeal from here and there and stop this tribalism of saying, “Those people are bad.” You know, the red versus the blue, the black versus the white, where you think that anything the other side believes is bad. And I’m on this tribe and everything my tribe believes is good. If you can get out of that and stop all of the isms. And open your mind to everything piecemeal for what works for you now. It’s very emancipating.
Sean
So what have you done Derek, to be able to step out of that and to be able to view these different things and see if they’re working or if they’re not.
Derek Sivers
Meditation. No, not meditation as much as reflection. I write in my journal a lot, sometimes for hours a day. I just keep my fingers on the keys in an open text file. A blank text file. Just asking myself questions, “Wait, what am I really doing? Why am I doing this? What was the real point? What do I hope to get out of this? Is this really what I want? Am I following an old script? What do I hope to get at this? What’s the end game here? Where is this going? Is that the most efficient path? Why am I doing this? What if I let it go completely? Would I be equally happy to not do this? Wait. Would I be equally happy to do nothing at all? Huh? If I’d be equally happy to do nothing at all, what’s worth doing if I’m happy either way?” You know, I ask myself questions like this every day and dive into the answers and and also doubting my answers. A lot of this stuff stems from a talk about a foundational belief. A foundational belief is I don’t believe anyone or anything. Not that I think everyone’s lying, I think that for most of us, the real answer to every single question is I don’t know. But we feel the need to come up with an answer anyway. So I don’t trust myself first. No matter what answer I give to a question. I suspect that I might just be saying that for reasons unknown to me, and it might not be the real answer if there is a real answer. So I start from that doubt.
Sean
So then all this reading, all this reflecting, all this learning, what are you searching for?
Derek Sivers
In this case in particular for my Useful Not True book. And by the way, thank you, this is the most I’ve talked about it with anyone, but maybe a dear friend or two. What I’m doing with this book in particular, I’m trying to learn more about this subject. So I’ve still got like five more books on my reading queue that I want to read that have written about subjects similar to this. The next one I’m reading, probably starting tonight, is something about like why we have religion and it’s an anthropologist who’s been studying religion for decades, tries to say why she thinks religion exists in the first place. Because I know everybody who’s really religious believes that their religion is true. But they are aware that there are other religions on Earth, so they can’t all be true. Unless you’re Baha’i. I think the Baha’is believe that they’re all true, but that’s going to be a fascinating one to kind of think about why we have religion, then not just take that literally, but think of that metaphorically, like, why is it when a book like Atomic Habits comes out that people read that and they go, “Oh my God, yes, this is the way Atomic Habits, this is the way I’m going to live my life from now on.”
Derek Sivers
And then a different book will come out, you know, 12 Rules by Jordan Peterson. They’ll go, “Oh my God, yes, yes. Sorry never mind that last book. This is the way.” Or to me, most disturbing is when they have a yes this is the way moment, let’s just stick with 12 Rules by Jordan Peterson. They’ll read a book like this, but then they’ll hear that Jordan Peterson got addicted to his painkillers and then they’ll see a picture where he has a messy room and they’ll go, “Oh, never mind. He is not the prophet I thought he was. This is not the way.” And suddenly, because of one person’s character flaw, they will trash and disregard hundreds of wonderful, useful ideas because that profit is now flawed. I think it’s a really harmful way to be all or nothing like that. I want to learn more about this human tendency to do that, because I think it applies to the “Useful Not True” book.
Sean
Yeah, that curiosity for you is clearly coming out. I’m actually generally curious about this. You mentioned the habits book for your habits that you’ve actually stuck to over years. Did they actually follow the framework laid out there, or were they either based on either you had so much pain that you needed to change, or you felt that inner compulsion that it didn’t matter? I’m bringing this up because I feel like you hear about, “If you want to start new habits, you need to break it down to the simplest thing. You got to reward yourself.” Everything like that and I was like, reflecting with some people who’ve done some remarkable things in the last few months around this and the times that I’ve made habit changes that have stuck for years, I can’t remember ever one time following that framework.
Derek Sivers
Yeah, actually, honestly, sorry, I read Atomic Habits long enough ago that I don’t remember the framework he describes there. But instead, I’ll answer the question sideways. Which is I think that all of my habits that have stuck started with a deep value belief. Meaning I can’t even think of one off the top of my head because they’re so internalized. Say that you’ve got a value that you believe that say--. Okay. Here’s one. Everybody knows I’ve got an open inbox. Anybody listening to this, you go to my website, you go to sive.rs and you click contact or email or whatever it says. And that will come to my eyes only, and I will reply within a few days. That’s important to me. I’ve been doing that for years. I’ve answered something like a quarter million emails from 80,000 people in the last ten years, and I love it because I have a value that says this is a good thing to do. People deserve to be respected and honored. I am benefited by the people I meet from around the world, especially when I meet people from places I know nothing about. A man from Riyadh, Saudi Arabia, said, “I want to meet you. I want to have dinner with you.” I went, okay, I’ve never met somebody from Saudi Arabia. He flew to Oxford, England, and we had dinner and he showed up in the big the white thing. I forget what it’s called that all white gown with the black thing around his head and a beard. And I was like, “Wow, I’ve never met somebody like this before. This is fascinating.”
Derek Sivers
And we talked for hours over dinner and I was like, “God, I love my inbox. I love the people that I can meet through this thing.” And same thing happened recently. I went to India for a week, and I met with 50 people in one week that I had been emailing with and I mean 50 one on one, like 1 to 2 hour long conversations. And it was fascinating. And I thought, “God, I love my inbox.” Okay, so sorry you’re asking about habits. So you could say that I have a habit of answering every email. But how did I keep that habit is because it comes from a deeply felt, profoundly powerful belief that this is a good thing to do and could stack up a whole bunch of reasons, like legs on a table. I like that metaphor that our supporting reasons can be like legs on a table. If you’ve just got one leg on a table supporting your belief, it’s like a diving board that might tip over. But if you’ve got a whole bunch of reasons that support this belief, you know it’s good because I meet a variety of people. It’s good because it makes other people feel happy and respected. It’s good because I’m developing these long term connections, and if I’m ever broke and homeless someday, I’ve got a lot of people I could call on to say, “Can I stay at your house, please?” It’s great because of this, because of that, because of this, because of that. I’ve got a whole bunch of reasons that support that value. That value is what really fuels the habit.
Sean
How did you uncover the ones that took the longest to deeply internalize?
Derek Sivers
Mhm. How do you mean?
Sean
How were you even aware that was the underlying value that drove all the essential decisions after that.
Derek Sivers
Because you asked. I mean, sorry, that’s kind of true. I mean, if you ask because you just asked about habits and I had to come up with one, I was like, “Well, what’s a habit? What’s the only thing that I consistently do, no matter what it’s like? Well, I always answer my email, why do I do that?” I just had to quickly ask myself, because I’ve got a value. Yeah. So I uncovered it because you asked.
Sean
Yeah, I’m just curious. Didn’t need to have this mapped out. Well, prior before that.
Derek Sivers
Thanks, Sean.
Sean
You mentioned deeply internalized. Have there been other--. What I mean by this is in your book, when you talked about the utopia with creating a different business, I feel like that was an idea that instantly got deeply internalized in me. And I’m wondering what ideas you’ve come across from other people that hit you like that.
Derek Sivers
Uh, dude thousands. That’s why I read. Sorry. I would just have to list thousands of them. But let’s say this if you go to my book list and again, anyone listening, if you’re unaware of this, you should know about this because it’s amazing on my website. I keep a list of every book I’ve read since 2007, every nonfiction book I’ve read since 2007, and for every book I read, I underline and highlight my favorite ideas from it. And then when I’m done, I put all of those into a text file. For my own future reference. So instead of having to read the whole book again, I can refer back to just my favorite ideas from that book. And then I post it on my website and it’s all free. Free for the taking. So if you go to sive.rs/book, you will see over 450 books there now. But I said 2007, that’s when I started doing this. That’s when I realized that I had already read a couple hundred books that I was forgetting. And so in 2007, I started keeping these notes at the age of 36. And there were some books that I read before that I thought, “You know, I’ve really forgotten this book. I want to reread it.” So I went back and reread “Awaken the Giant Within” by Tony Robbins, which I read at a very formative age of 19, and oh my God, Sean, it was like a Christian reading the Bible. It was like a Hindu reading the Upanishads. It was like, “Oh, this is where all of my beliefs come from.” I had forgotten I had internalized these things so much. That I think this is where a lot of them came from. So a lot of the way I see the world comes from the book “Awaken the Giant Within” by Tony Robbins.
Sean
That’s interesting. You mentioned doing the highlighting and posting those, which I think is literally one of the most incredible resources, free ones on the internet. I’ve shared your site countless times over the years, but would you say that became a ritual for you? And I’m asking because I know you put nuance in the differences here between habits and rituals.
Derek Sivers
Ritual implies regularity. Ever since I moved to New Zealand in 2012, I have a ritual of waking up and making breakfast by pouring a half bag of baby spinach into a bowl, cooking a can of organic black beans, and pouring that over the baby spinach and sprinkling a little cheddar cheese on top. That’s my morning ritual, and actually always putting on a pot of boiling water and making a cup of black tea. That’s my morning ritual. The book notes I think it’s a little bit like flushing the toilet. It’s just something I always do afterwards when I’m done with a book. Even if I don’t feel like it, I don’t take great joy in doing it. Honestly, it’s quite tedious. But when I’m done reading a book, I go like, “All right, let me copy down all these notes into a text file.” It’s not fun, it’s tedious, but it prevents me from ever having to read the book again. And it benefits me greatly by being able to refer back and remember and most importantly, internalize what I’ve read.
Sean
Interesting. Well, through all your learnings and all the knowledge that you have, how do you approach your fears?
Derek Sivers
I don’t have any fears.
Sean
And why is that?
Derek Sivers
I don’t know. Well, maybe I do know, because I either heard of or thought of an idea when I was a teenager. And it’s whatever scares you, go do it. So ever since I was like 16. I’ve had this little rule of thumb. Whatever scares you, go do it. And it’s often just used in the moment. Like if I’m feeling intimidated and scared to talk to some-- I’m thinking a teenager now, so I’ll say cute girl. I’d be like, “Oh, I’m scared. Okay, I’m going to go do it.” Because the end of that thought is whatever scares you, go do it. Because then it won’t scare you anymore. That every time you do these things that scare you, you realize it wasn’t so bad. And then you come away not scared of that anymore. And so then you go on to the next thing that scares you. Or just whenever you notice you’re scared of something. I turn towards it immediately and do it, and then it doesn’t scare me anymore. I ended up making this a lullaby for my son when he was like three years old. I would just sing to him every night, and I’d sing Over the Rainbow and Blackbird and whatnot. But I thought, you know, I’m a songwriter I can do this. Like I want to put this subliminal message in his head. So I started singing him a song at the age of three that just went, “Whatever scares you, go do it.” And that’s his nightly lullaby, has been for years. I still sing it to him sometimes. And he’s 11. So I think I’ve been following that habit, ritual?
Derek Sivers
No habit, for so many years that there’s not much left that scares me. But when I do notice something. Not even scares, but even feels like a little weird, intimidating, unusual, unknown, even just those variations on fear. I steer towards it immediately. So, for example, I’m going to the United Arab Emirates for the first time. Yes, I mentioned earlier like this guy from Saudi Arabia that flew to Oxford to have dinner with me. But besides that one dinner I don’t know anybody from the Middle East. I know nothing about that part of the world. And so I realized, okay, yeah, that part of the world kind of scares me. So here I go, I’m going to United Arab Emirates in a month and a half.
Sean
So what is the internal dialogue for you like Derek, in that in the moment where the opportunity gets presented? And you feel that inner tension.
Derek Sivers
Oh. Sorry. It’s just as simple as I just described. There’s this feeling of like, “Oh, wow. I know nothing about--. Wow that part of the world is alienating, people are they’re so different from me. Yeah. I’m kind of scared of that, aren’t I? Huh. Well, whatever scares you, go do it. All right, hold on. Let me look at booking a flight.” It’s really as simple as that. Like, I just try to take action immediately. When I notice that something’s scaring me. I feel it’s almost my duty or mission to steer towards these things and demystify them.
Sean
You know, a lot of people. You’ve met, a lot of people. Have you found that to be common?
Derek Sivers
I don’t know. No. Maybe not. No. I think a lot of people use their fear. They rationalized their fear. They justify their fear and use it to stay safe.
Sean
One of the things that’s becoming very obvious for me about you, and I know you’re probably going to blush it and go humble here. You have incredible deep internal awareness in the present moment.
Derek Sivers
Thank you. What does that mean? I don’t really understand.
Sean
So just ease of conversation, right? You have stimulus response, right. And so obviously you’re trying to expand that time. So most people doing that’s very hard right, between stimulus and response. When something happens and you react, you not only are able to expand that time, you are actually able to go internal. Most people have to wait till after the experience happens. You get cut off in traffic. Okay, maybe I can expand that moment, but I’m not going to be able to really process my emotions, my feelings until a later date.
Sean
From what I’m getting from you is you can go inside through the moment.
Derek Sivers
You know, I’ve known Tim Ferriss for 15 years. I met him in 2008, but just a month ago he was here in New Zealand visiting, and we spent a whole week together. Every day, like, whatever, 30 hours of just walking around the forests and talking and I was amazed at how much he was remembering things I had said offhand, like three days ago. Three days later, he’d say, “Let’s come back to that thing you said three days ago where you said this sentence.” And I say, “Whoa, dude, how did you remember that?” And he’d say, “It’s a side effect of the podcast is that I’ve been doing this podcast for so long, it’s become a trained skill that’s developed to remember conversational threads that were left open. To take those threads and come back to them.” Wow. Okay, so it’s just a side effect of something he spends a lot of time doing. Right. So this thing that you just said that I do, I guess you’re right. And I think it’s a side effect of all the journaling I do. Like I said, for years and years and years, I’ve spent so many hours in my journal asking myself questions and then questioning my answers. That you’re right. It’s probably just a skill that’s developed over the years to just do that in the moment and do it all the time.
Sean
That’s what I’m so intrigued by. And so many of the questions are basically around trying to get to that core. What are the things that you did that led to these things being a side effect, even being able to step outside your own beliefs around what your parents told you, around what society told you and question them. It’s essentially a side effect of things that you’ve done in the past, and it’s going to be very hard for someone to be able to do that, to be able to question those beliefs unless they’ve done the work prior to that, to allow that to unfold.
Derek Sivers
Yeah. And this will be a hard thing about my next book Useful Not True. Is, a few people have said when I described the idea to them, “Yeah, but how can I just choose a belief?” I say, “Well, what do you mean how. You just choose a belief. You just choose it. You decide that this is what you need to believe. You stack up some reasons why you need to believe it, and you decide to believe it.” And they look at me like I’ve said, you know, just pick a tall tower and climb it. So, yeah, I’ve got to work on that if this book is going to be useful to others. I’m going to have to figure out how others can get better at this. Interrupting and choosing beliefs.
Sean
This is why I asked you a question. I actually loved James Clear. I love a lot of things he said. The reason I asked you is because I think most changes, most of these big changes, like being able to adopt a belief, comes from you, goes through something so painful that you’re so tired and sick of the pain you need to change, or you are so compelled and so internally driven that you will run up that hill, no matter how much it hurts.
Derek Sivers
Right? Right. Yeah, I think I’m so driven to run up that hill.
Sean
Yeah.
Derek Sivers
Maybe because of all the books that you and I have read, it sounds like we’ve read a lot of the same ones. My favorite moments in life are when I’m reading a book that makes me go, “Whoa. I never thought about it that way.” The recent-ish one that comes to the top of my head is “The Courage to be Disliked.”
Sean
Oh yeah.
Derek Sivers
A fascinating book that had so many things in it that made me go, “Whoa, wow. That’s a different way of looking at it. And that works. That’s interesting. I had never thought about it that way.” And it blows my mind because when you take in something like that. You could put the book down, walk out your door the next day and just see the whole world differently because of something you read yesterday. And I love that feeling. I think that’s one of my favorite feelings in the whole world, so I guess I’m constantly trying to find or make those moments.
Sean
This has me thinking about something that you actually have to quote here too. It’s, “Most actions are a pursuit of emotions. You think you want to take action or own a thing, but what you really want is the emotion you think it’ll bring. Skip the action. Go straight for the emotion. Practice feeling emotions intentionally instead of using actions to create them.” What’s your approach for this? Yeah that’s this is a good one too Derek.
Derek Sivers
Was that from How to Live?
Sean
Yeah.
Derek Sivers
See when I hear these quotes, I’m like, “Oh, that’s good. Who wrote that? I wrote that. Wow. Damn. That’s good.” So. All right.
Sean
I’ll fill you in on how I do a similar process to you. I probably adopted it from you. When I read a book, I get to go through my notes. I was going through my notes on How to Live. So I’ve got like bulbs, I’ve got yellow highlights which are like, this is good. And then I have these green ones and there’s probably like 6 or 7, maybe eight green ones. And so like mastery is one of the green ones. And so I’m going through and I’m like, “Oh these are really fricking good.” So that’s my process. So it was very easy for me to go through and pull some of the things that have really hit me over the years. And How to Live really was one of those books. I put it down, I was like, “Holy shit, this is awesome. This is really awesome.” I mean, I’ve bought a ton of them for people. But yeah, I’ll let you expand on the pursuit of emotions.
Derek Sivers
Oh, right. That idea might have come from Tony Robbins in the first place when I was a teenager. But sometimes it’s just practical that if you think, “I want to go to Fiji. Why do I want to go to Fiji? So I can relax. So I could sit on the beach and exhale and relax.” And I think, “Well, that’s a lot of money and a lot of time. How would I just feel relaxed right now.” And I can just ask myself that question. And then you may even come up with some bad answers first, right. “I could go have three beers and feel pretty relaxed. Well, that’s not a really sustainable solution, is it? Can’t do that every time I want to relax. What else could I do? I can lay down and close my eyes. That sounds pretty passive or that’s probably not effective enough. What else could I do?” And you keep challenging. Never, never stop at the first or even the second answer. Keep pushing yourself for more, and you might go back and find out that the second answer was best, but keep coming up with more just to know. And somewhere along the lines. So I was living in Singapore and I was feeling very claustrophobic. Not claustrophobic like I’m in a tiny recording booth right now, which I am, but I mean, like urban claustrophobia.
Derek Sivers
Like. Oh my God, everything around me is a city. I just want to be, like, out in a field of tall grass blowing in the wind. I think, “All right, well, I can’t do that right now. There are no tall grass. There’s no tall grass blowing in the wind in Singapore.” So I just say, “All right, I’m just going to close my eyes and I’m going to lay down, and I’m going to vividly put myself into a field of tall grass blowing in the wind.” And I go, oh, okay. This actually helps, you know. And I would really vividly imagine it. I’d often fall asleep imagining tall grass blowing in the wind. But then that also helped steer some life decisions, because after doing that enough nights, I thought, “All right, I love Singapore, but I think I need to get out of here now. I think I need to move somewhere with tall grass blowing in the wind, because my soul is clearly needing that. Or at least I think I need it. Let me go find out.” So I moved to New Zealand and I was right. There’s lots of tall grass blowing in the wind here and it makes me very, very happy.
Derek Sivers
But before I could go move to New Zealand, we can’t all do that. Just putting myself directly into feeling the emotion I want. I don’t even really officially meditate. I don’t, you know, cross my legs and do a position with my hands. It’s just as simple as you just lay down and you think. You just close your eyes and you vividly imagine something. Maybe you’re not feeling loved right now. And you can vividly imagine the time when you did feel most loved. Just think of a moment where you felt really, really loved and you could just vividly bring that back to fill your soul. Right. Fill your mind with that. And then it’s kind of the same as the senses, right? Like even when our eyeballs and our ears take in something, it’s just converted into signals in our brain anyway, so you can just fill your head with those signals directly. Yeah, I think people who have a great need for adrenaline, a great need for feeling important, and they think that they need to go make 1 million. No, wait 10 million, no, wait 100 million to feel important. You can instead just try to go straight for feeling important and not have to go through all these annoying steps.
Sean
You were essentially describing what an elite performer would use as a visualization practice. You essentially are tapping into a total sensory experience. Yeah. It’s pretty interesting. I didn’t know you did that deeply.
Derek Sivers
I don’t have to do it that often. It’s when I’m feeling in need of something, or I’m feeling like the strategy I’m pursuing is very inefficient and doesn’t work for me in many ways, like the Singapore and the tall grass example. Then I’ll do it to get there directly. But there are other ones that I think you know what? I want this thing. And this is a good thing to do. So it was really just three months ago where I was feeling that I want more friends. And yes, I could go out here in Wellington, New Zealand and make some more friends. But you know what? I feel like going somewhere where I predict that I will likely be more in the future. I want to think long term. I want to think like Derek in ten years from now. Where will Derek in ten years be? And I thought for many, many years I’ve wanted to live in India. I even have the legal right to live in India. I’m what’s called an overseas citizen of India. So I have the paperwork that’s basically a passport giving me the legal right to be in India. But I’ve never spent more than a couple of weeks in India, so I thought, “I’m making a decision now. I’m going to start going there more often, and I’m going to start by reaching out to a whole bunch of interesting people that have emailed me over the years. I’m just going to pick two cities. Let’s just pick Chennai and Bangalore. I’m going to start there and I’m going to go meet with these people face to face.” And that’s what made me hop on a plane and do that. Was that I wanted to consciously develop friendships. And just laying down and closing my eyes was not the right solution for that. Getting on the plane and meeting these people face to face was.
Sean
Consciously develop. That’s one of the keys. That for you. Mr Derek Sivers, I think is one of the keys. I think that’s one of your superpowers. I’m saying that because I’m looking at this the past hour. You have a deep self awareness journaling practice where you can go in, you can ask yourself questions, very good questions you’ve cultivated over time. And then you can go further and ask yourself harder questions and go towards your fears in the moment. And then you don’t stop on the surface and you go ten layers deeper. And then, like you said, you’re able to to visualize if you need to. And that is how you consciously have developed some of these different skills over the years.
Derek Sivers
You basically just sum me up, add a shaved head to that and that’s me.
Sean
No, I’m just like, it’s fun to see. There’s this great line by Martin Scorsese and he’s talking about DiCaprio, and he says, “You’d never get to see how the watch is made.” It’s something along those lines, meaning I’ve watched this kid meaning DiCaprio from a young age, do what he’s done for years, and I still don’t know how he does it. It’s so well executed on the surface. And so I feel like I’m getting a peek behind into how this watch is slightly made. And it’s incredible because a lot of the things that you do, everything i was just listing out there is very hard to do, and it needs to be cultivated over years. So I have even a deeper amount of respect for you because that path to mastery where we started is true. You can only face your fears and actually go towards them. You can only challenge and change these beliefs because of your path to mastery on being able to go further into these things. And so I just say, you know what? I appreciate you sharing these types of things publicly so other people can learn how to go after and do similar things. So thanks, Derek.
Derek Sivers
Thank you. And by the way, I wasn’t kidding. I did feel that you summed me up very well. Probably better than I could have myself, that is the core of what I do and what drives me. So thank you.
Sean
Final one. So I love doing this, interviewing someone and say, you could do this, but you’d get to spend an evening interviewing anyone, dead or alive. Who would you love just to ask any question of?
Derek Sivers
Guess what? I went through this recently. The answer, surprisingly, is my kid, age 11. He is alive, and I thought for hours about all the people that I could meet, could get to know better, could spend a day with. And we could go into the deeper reasons why, if you want to hear it. But the conclusion I came to is actually, the one that’s to me the most meaningful, the most rewarding, the most future focused. It’s my kid. I would rather spend a day with my kid than anybody that ever existed in history.
Sean
I have two young sons at home, and I can guarantee you I’m different now because of that. Derek Sivers this was well worth six years in the waiting. Let’s not wait another six years.
Derek Sivers
Thanks, Sean. And, hey, anybody listening to this, you heard it. Go to my website, send me an email, say hello. It’s the reason I like doing these things. I’m not here to promote anything. I like doing these things because of the people I meet afterwards. So anybody listening to Sean’s show, “What Got You There” Go to my website.
Sean
I’ll have everything linked up like we always do. So some of the things we mentioned, all the books that Derek has written over the years, I’ll link up some of the key articles that I’ve enjoyed as well. You guys can find out all of those at the show notes as always, but Derek Sivers can’t thank you enough for joining us.
Derek Sivers
Thanks, Sean.