Keep Talking
host: Dan Riley
Wonderful insightful questions about beliefs, money, intensity, motivation, imitation, and changing your mind.
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Transcript:
Dan Riley
Derek Sivers, it is lovely to see you again. Thank you so much for doing this. Welcome back.
Derek Sivers
Thanks. I'm actually really looking forward to this 'cause I figure the first time we talk, there's always a getting to know you, getting the basics out of the way. And the second time we can get into the better stuff.
Dan Riley
I'm down, let's do it. I wanted to start this one with sort of a continuation of some of the things we talked about in round one. I thought it might be helpful to begin with some of your truths, your key principles. And I wanna read something from you and then read a quote from one of my favorite guests of all time on this show, Kevin Kelly. They're very similar ideas. And this is the quote from you. It's about taking action and the importance of actions in your life. And I will read Kevin's first and get his statement out there and have him sort of set the tone for us. Let me find this here. This is the quote from Kevin Kelly. "You are what you do, not what you say, not what you believe, not how you vote, but what you spend your time on." And you have written a lot about actions and the importance of actions and how they reveal your values. And this is the line from you I wanted to read. Quote, "No matter what you tell the world or yourself, your actions reveal your real values. Your actions show what you really want." I wanted to set the table with that idea, those two ideas, and give you some time to flesh that out a little bit about what you mean by that statement and how you think about actions being really what matters in showing who someone is.
Derek Sivers
Sure, I'll start with the background context by the person that pointed this out to me is an old friend I've known for a long time, but we hadn't talked in a year or so. And he said, "So what are you doing? What you working on?" I said, "Well, you know, this year, I really wanna start that business idea I've told you about." And he said, "No, you don't." I said, "What do you mean, no, you don't? I'm telling you this is what I want to do." He goes, "No, you really don't." I said, "You can't just say no, you don't. I'm telling you, I'm the person with the desire to do this thing. I'm telling you that this is what I wanna do." And he said, "Derek, no, if you really wanted to do it, you would have done it by now. I've heard you talk about this idea for like eight years. If you really wanted to do it, you'd be doing it. I think you need to admit to yourself that you don't actually want to do it. Or go prove me wrong with your actions. Just saying you want to do it doesn't mean you actually wanna do it. Your actions are revealing your real value is that you don't actually want to do it." I went, "Whoa, dude, you're right." So that was my introduction to this idea. And I've just thought about it a lot since.
Dan Riley
There's another line I wanted to go over from you, which in version one, I was not able to get out. And I wanted to give you some space to talk about this quote which has been one of my favorite of all time. Let me just read out the quote you're referring to that is in your book. Actually, I'd written this down. Quote, "You have a goal you've been putting off. You wanna do it someday. You've been meaning to take real action on it, but could use some motivation. Let it go. It's a bad goal. If it was a great goal, you would have jumped into action already. You wouldn't wait. Nothing would stop you." This is the second line I wanted to read out, which I've thought about a lot since coming across it many years ago. Quote, "Everybody's ideas seem obvious to them. I'll bet even John Coltrane or Richard Feynman felt that everything they were playing or saying was pretty obvious. So maybe what's obvious to me is amazing to someone else." I think a lot of people who follow you are creative types. And this is another subject I wanted to put to you just to give you some time to talk about that idea of what's obvious to someone might be brilliant to someone else. I think you've given examples in your writing about people you've come across that you feel that way about and I wanted to give you some time to reflect on that.
Derek Sivers
Sure. I think a lot of it comes from knowing the source of our ideas. That say if you read two different books and got half of an idea from this book and half of an idea from that book and you put it together into something new, well then, duh, you know the source. It seems pretty obvious. But to somebody else, they go, "Whoa, I've never heard somebody say that before." But you go, "Well, yeah, it's just the combination of this and that makes this. So that's pretty obvious." But if somebody hadn't read your same source material, they wouldn't have come to that conclusion themselves. So it helps to remember this and just share everything you can, even if it seems obvious, because for somebody else, it's not.
Derek Sivers
Sorry, you're bringing up so many interesting things that we could dive into, but I think I'm gonna need you to lead the questions of how you want to dive into them.
Dan Riley
Yeah, I wanna get into, if you're open to it, a subject that we talked about the first time, which was money, and give you some time to talk about what money has really given you. I know after our first conversation, I was mentioning to you that I wanted to give you some time to talk about something you made in an offhanded comment about saving someone's life for a couple thousand dollars. And I wanna make sure to give you some time to talk about what you have learned in your life about how that's possible. I know you've talked about the difference between taking an economy flight and a business class flight, potentially being the difference between donating money that can save a few people's lives. But before I do, I wanna give you another opportunity for people that haven't seen our first conversation to talk about how you have thought about money. I mentioned in our first conversation that I've heard you talk about money after a certain point being something akin to hoarding for people that have so much of it. And you're not anti-money, as I understand your perspective. I know that it's given you a lot of freedom, which was something we talked a lot about in our first chat. If you could talk about the value that money has given you and also the point at which you felt like money was no longer something really of great value to you that you basically, I know, have donated a lot of money, which was a bit like giving a shirt to someone who could use it more than you. Maybe we could open up that conversation before we get into philanthropy specifically and give you some time to talk at this point about how you think about money in general.
Derek Sivers
Sure. It's so handy. It really is useful. I'm definitely not anti-money. Long ago, maybe 10 years, oh God, 15 years ago, there was a girl that I met in Portland, Oregon that really looked up to me. We were friends, but she was much younger. I think she was 22. She was a cool person, and we were friends, but she made it clear that she wanted to be like me. And I'm a really naturally happy person. And she said, she was talking about some scenario where maybe I mentioned something that happened in my life that other people would think of as a tragedy, but I found a way to just reframe it as something I can learn from and move on. And she said, "God, how can I be so happy like you?" And I was quiet for a second. I said, "Well, first you get a million dollars!" It really helps to protect against the downside.
Derek Sivers
I'll give a real concrete example that comes to mind. I was getting married and we were living in New York City, but getting married in Seattle because I was still technically a Washington resident at that time. And so it was one of those things where in order to get the marriage appointment, you had to book a time with the judge like two months in advance. So we were given this very specific time slot. It's like a Thursday at three o'clock, we were going to go meet the judge to sign the marriage certificate. And we were flying out of New York City that morning out of JFK to arrive in Seattle at say 1 p.m. with just enough time to go from the airport to get lunch and then go meet the judge for the three o'clock appointment. So we get to the JFK airport in New York City and look for our Delta flight. And they said, "No, Delta doesn't fly out of JFK." I was like, "What do you mean? No. Our flight...." And then we looked closer at the ticket. Oh crap, we're flying out of Newark. Oh my God, our flight's in 45 minutes. We've totally missed it. There's no way we're going to make it. Oh my God, that means we can't get married and it will be months before we get another appointment. We're so screwed." And the woman went, "Actually, there is a flight leaving in 20 minutes, but there's only two first class seats left and it's going to be like $7,000." And I went, "All right, let's do it. Put us on that flight." And we made it in time. That, to me, was a perfect example of how money can be pretty meaningless. I don't want any extravagances. I don't own luxuries, except maybe this recording booth I'm standing in right now. But man, it really helps protect against the downsides of life.
Derek Sivers
So I often think of benefits and drawbacks in terms of two different things. You can optimize for the upside or you can protect against the downside. And some people's life's philosophies, like go get a good college degree, that's not the greatest upside, but it can help protect against the downside. Things like that. So in this case, money protected against a huge downside. And I was very thankful in that moment.
Dan Riley
And as you got more and more money in your life, and I know you talked in our first conversation, I've heard you tell other people these stories about the first time you had something like $20,000, that that was to you, just an incredible amount of money. And when you hit $100,000, you basically had the mentality that you were set for life. And the point, as you accumulated more with CD Baby, as you earned more with that profitable business, did you always know that the end goal for yourself of having money outside of your basic necessities was to have a life of freedom? Was that always clear to you that you wanted independence and autonomy? Did you sort of grow into that realization as you had more? What's that story there?
Derek Sivers
Yeah, freedom was always the point. I have never in my life wanted a Ferrari or a mansion or a boat. Those things always just seemed like stupid wastes of time. But maybe this is also because by my value system and my goals in life, I just wanna work. I don't hang out. I am the opposite of a hedonist. I don't do leisure. I don't enjoy relaxing. I have so many things I want to do with my life. I just wanna work. So, so many of those cliche, rich person indulgences are leisure things and those just don't interest me at all. I just wanna work all the time. So I think of money as giving me the freedom to work on whatever I want without having to work for somebody else.
Dan Riley
You said a minute ago that you were a happy person, that this friend of yours, this acquaintance, wanted to be happy like you. And is it, in your mind, do you think that lack of the hedonist materialist desires that I think a lot of people who accumulate decent amounts of money go for? They go for the Ferrari, the Country Club, the luxury home, that that was never particularly appealing because of your default state as a human being? How do you think about that lack of interest, almost like a repulsion from those sort of materialist items? How do you think about that for yourself?
Derek Sivers
I think of it more in terms of deep happy versus shallow happy. Shallow happy is laying on a nice beach. Deep happy is writing a great book. Shallow happy is eating ice cream. Deep happy is being fit and healthy because you didn't eat the ice cream. It's a deeper happiness. We're overloading this word happy. There's a more accurate term like fulfillment. This deeper happiness in your gut of living to your full potential and living according to your values or creating something that's going to live past yourself, it's being proud of what you've done. That, to me, is a far more fulfilling deeper happiness than eating some fancy meal. You know what I mean? So all I've wanted in life is to realize my potential. I say realize like to turn it into reality, not to just notice it. So I want to write the best books I can write. I wanna make the best music I can make. I want to turn my ideas into reality. I wanna make my ideas as great as they can be and then turn them into reality as great as it can be. All of that is my life's mission. That's what I'm doing all the time. I bounce out of bed at five in the morning to work on these things. Country club, Ferrari, boats, et cetera, those are the enemy of productivity. Shallow pleasures are like the devil on your shoulder that would steer you the wrong way to do the wrong thing. What you really want is to create and to make and those pleasures pull you away from doing that. So that's maybe, I think it's not because of my DNA happiness, but more of a sense of what I'm doing in life.
Dan Riley
You talked a lot in our first conversation as well about the importance of learning and that learning in your mind requires some space from information, some reflection to be able to take if this, then what, to be able to come to conclusions about what you're seeing in your life. And I wonder if you seem like a deeply intrinsically motivated human being. And I think many of us, myself included, aspire to be like that as much as I can. Do you regard that having your direction set towards the deep happy versus the shallow happy as a primarily DNA wiring that you were born with, or was that also a carrot that you gleaned over the years of coming back to the journal every day and asking yourself these difficult questions about what's really bringing you fulfillment in your life?
Derek Sivers
That's a fun question. And when you said carrot, I thought you were gonna say, was it the carrot that you tasted? I tasted the carrot of pride.
Derek Sivers
No, I think it's not DNA, it's learned values that I got maybe from age 14 where I set out to be a great guitarist. As soon as I put my first electric guitar in my hands, I was just like, oh yes, this is what I want. And I set out to be great at it. I started taking lessons and hours and hours and hours a day, like four or five, six hours a day, I would spend doing arpeggios and scales and chords and picking exercises and learning to play guitar solos off of difficult Eddie Van Halen records or whatever. Spent so many hours perfecting my skills and trying to learn this and just practicing so much, working so hard to be as good as I can. And that's when I started to get feedback from the world saying, "Dude, you're a great guitarist." And it felt a little bit like you telling a bodybuilder that they're buff. It's like, "Well, yeah, I know I put in the hours." That's what it takes. You put in the hours, you work hard, you get good at something. And it just, it was so much more satisfying to me that feeling of getting great at something or having a musical idea in my head and doing the hard work to make it happen, to record it and take that song idea and make it real. And I could listen to that song going, oh yeah, I did it. I had this idea and I made it happen. I recorded it. Now I just wanna play it over and over again. It's so good. I love this song. That was so much more satisfying than just going out and getting drunk with my friends. So I think that it's just been an ongoing continuation of that. Now, instead of music, it's writing and it's programming or even just learning new things, learning to speak another language. It's this challenge of pushing yourself to your potential.
Dan Riley
A lot of that requires an incredible amount of focus to be able to do it. Self-knowledge about what you wanna do, guitar writing, et cetera, and then the discipline, the interest to continuously come back to it.
Derek Sivers
When you say it requires an incredible amount of focus, I gotta disagree. I gotta challenge that point. If you're having sex with somebody that you adore, it doesn't require an incredible amount of focus to keep your attention on that person. It's just all you want. You're just filled with desire for this other person. I feel like that when I'm working, it's not an incredible amount of focus. It's just this intense desire. I want so badly for this book to exist. I want so badly for this program to exist that I'm programming. I want it more than anything else. Everything else can fuck off and disappear. I want this thing so badly. It's not focus, it's an intensity of desire.
Dan Riley
And do you think that intensity of desire is something, not everybody has that, right? I mean, is that something that you just have and you can tell it's there and then the desire drives you? Is it really that simple of a recognition that the desire is there and then you pursue it? Or do you think of it another way?
Derek Sivers
I don't know other people's minds very well, so I don't understand what it would be like to not have any desire. I guess that would be depression. People will email and ask me, "How do you get so excited about things?" Or "I'm just depressed, I don't know how to find my calling." I don't know what to say to them 'cause I've just always felt this way, yeah, since I was 14, I guess, and started playing guitar. It's just been this ongoing, intense drive towards my interests. It was just there. It comes from a love of it. It's starting with the music example I gave, just from this love of this music, I was like, "Oh my God, I wanna make music like that!" And then it became intellectual challenges. I would hear this Nigerian music from Fela Kuti mixed with these simple structured melodies from the Beatles, mixed with this deep '70s funk of James Brown and I'd think, "How can I mix these three things? This is a challenge! Can I?" And I would try it and sometimes it would fail and I'd try a different mix and it would work out and I'd make something new that nobody had made before. That was so deeply satisfying. And then say I'd read a business book on guerrilla marketing or something, I'd think, "Can I do this? Can I make this happen? Could I actually double the price I get paid for my gigs if I just try this technique I learned in this book?" And I'd try it and it would work. I'm like, "Whoa, I did it, this is so satisfying!" And then that led me to accidentally start my first business which then that became its own intellectual challenge. Like, hmm, "Can I make this site more appealing to browse so that somebody who came to buy one album will leave with 10 albums? Could I do that?" I take that challenge and it's just so interesting. So all of these things just kept leading one to the next. And now I just have this great love for well-written books. I say books, but I mean, it could be articles. Just a love of great writing that's not full of fluff that just gets to the point and blows your mind. It's so satisfying when you read something like that then I think, "Ooh, can I do that? Can I be that great of a writer? How can I do that?" So I'm just still so driven by this challenge.
Dan Riley
I would imagine a lot of people who follow you for as many years as I have, have gotten that sense from you that that love of work is obviously there and has driven a lot of what you have achieved, have produced in your life. And I don't know that I've ever had come across an interview where somebody has brought this up with you, but has there ever been a phase of your life more than a couple of bad days where that optimism, that excitement, that for lack of a better word happiness has not been there where you've struggled to find the next thing? Or is that really not a part of your life?
Derek Sivers
Yeah, there was a year and a half after I sold my company where I felt adrift. I had a vague desire to slough off all responsibility. I had all the money now, so I had total freedom. Sold the company, I had nothing I had to do. I had nowhere I had to be. I'd even just recently broken up with my girlfriend. So I was single, I was free, I was completely unattached. I had no responsibilities. And oh my God, it was like a blank slate, which is intimidating. Like a blank page to a writer. Where do you start? You have infinite potential right now, infinite options. Oh my God. The overwhelm was too much. And I felt vaguely and mildly interested in many different things, but I didn't feel intensely driven by any one thing. And so that left me feeling adrift. And that lasted for a good year and a half. I strongly considered legally changing my name and moving to Europe somewhere to just be an open source programmer in obscurity. But even that didn't inspire me enough to actually do it. Like we started the conversation with, I said I wanted to do it, but I wasn't actually doing it.
Derek Sivers
It wasn't until this one lightning bolt of a moment sitting in an airplane seat, reading a book, that comes back to another earlier thing you asked about the difference between a good goal and a bad goal. So here, I'm gonna tie a few of the subjects you brought up all together in this one moment, is yes I was adrift, yes I was feeling something akin to depression and a lack of motivation for a year and a half. And I'd had various goals, but they didn't spur action in me so therefore they were not good goals, no matter how impressive they might sound to others. And it wasn't until this moment, I was sitting in an airplane seat on my way to a friend's wedding in New York, and I read one sentence, it doesn't even really matter what the sentence was, it's what it sparked in me. But I believe it was about Benjamin Disraeli who was a prime minister of the UK and how he rose from nothing, from a commoner to prime minister in an age where typically only the aristocrats rose like that. And he did it by deliberately courting attention and going into the spotlight instead of away from it. And in that moment I went, "Right, I've been avoiding the spotlight because I didn't want the responsibility. But if I lean into it and just take on the extra responsibility, then so many great benefits will happen." Because my heroes are people like Seth Godin or Malcolm Gladwell that are known for being brilliant thinkers, writers, speakers. At the time I was really into TED Talks, it was 2009 and TED was a thing then. And I thought that these are my role models, this is who I wanna be. I just had this lightning bolt of like, "If I lean into this instead of away from it, I think I could be like that. I could be this writer, speaker, thinker kind of guy instead of this ex-entrepreneur." And that idea was maybe idea number 120 over the past year, but that was the one that made me go, "Oh my God, yes. And if I were to do this, here's exactly how I would do it." And I started making this plan, I was like, "I'm gonna do this, I'm gonna start writing an article every day, I'm gonna start reading, I'm gonna start reading books, but very deliberately in a way that I'm gonna glean things from them and I'm gonna combine ideas and lateral thinking very intentionally, I'm gonna keep a database of ideas and try to combine them together to make new things. And I'm gonna start meeting with people that other writer, speaker, thinkers, I need to publish one article at a time and call attention to it, then eventually I'll compile them into books, I need to get into the TED conference to be a TED speaker." And I got so charged up by how I was going to do this, I just noticed I was sitting up straight in my seat, I was typing like crazy, and then as soon as my plane landed in New York, I called a friend, I was like, all right, you're gonna cancel my return flight home to LA, I'm gonna stay right here in New York, I'm gonna make this happen, I need to get a place just right in the middle of town, I wanna meet with people, I'm gonna start publishing something every single day, I'm gonna make this happen, I'm gonna get invited to speak at the TED conference. And just like suddenly I had that drive and energy again that I hadn't felt in a year and a half. And who's to judge whether that goal was objectively a good or a bad goal, but that was the goal that made me take action and changed everything. So to me, that was the worthy goal.
Dan Riley
And for other people that might be coming across this, that waiting, you said it was the 120th idea that you had maybe considered in those, however long it was, a year and a half or so. For yourself, I guess this is the best way to ask it, if you ever were to be in a situation like that again, where you were rather adrift and uncertain about your next phase, and you may have just already answered this, waiting for that clarity, that energy, where you're beginning, you're so excited, you just begin taking action immediately. Would that be your advice to yourself?
Derek Sivers
Yeah, mixed with reading, lots of reading. I think I had to read 50 books that year before I came across that one sentence and that one book that made the difference for me. So that is my advice to people that email and ask about something similar. I say, when you're feeling adrift like this, just read a lot, take in a lot of possibilities and spend time in your journal to think of how you could apply this to your own life and what this implies. And that's what did it for me. So that's what I would do again if I were in the same situation again.
Dan Riley
Yeah, this is related, I think, to what we've just been talking about. This is an idea I came across in preparing for this conversation that I don't think I'd ever heard you say before, where you were noting a common idea or principle that a lot of people have, which is that you become the five people that you're closest with and that you disagreed with that idea. And you thought a better take on that was that you become like the people you emulate, if I remember that correctly. And in what I just heard about the people that you admired at that time in your life that you look up to, I think you used the word heroes, Seth Godin, Malcolm Gladwell, they were the kind of people it sounds like that you wanted to emulate. And I wanted to just give some space to you to talk about that concept. And I don't know if it's admiration is the right way to put it or just wanting to emulate someone, that that's the course a person is setting for their life. If they have these people that they admire that they wanna be like. Just wanted to put that to you to get any additional commentary you may have on that.
Derek Sivers
Yeah. It's the incredible power of heroes and anti-heroes. Anti-heroes don't get enough attention. I've been so driven by what I don't want to be. You hear this when people are dating. When somebody's single and dating, if you ask what they're looking for in a relationship, they will usually tell you all the things they don't want because they've found from their past relationships. "Well, I don't wanna be with somebody that watches TV all the time." "Well, I don't wanna be with another depressed person again." They'll tell you what they don't want. And eventually they narrow down what they, well, maybe they just get somebody that doesn't tick any of those don't want boxes and then they're happy. So I think of anti-role models a lot. When I see somebody that's living in a way that I despise and I go, "Oh, I never wanna do that." That can drive me away from it. I can see, okay, that's the direction that that goes. I'm going to run the other direction to make sure I never go that way. So whether it's the hedonists or the egotists or the preachers, people who go off on a branch of this path that I could go on if I wasn't careful.
Derek Sivers
Maybe it's almost like a trap. I'm imagining a walk through a jungle right now. And the person that accidentally walked over the deep roots and then tripped into the sand and now they're in quicksand. I go, oh, I never wanna go there. Note to self, never do that. I'm so driven by these anti-role models that squandered their talents, that gave in to egotism, believed all the flattery and thought that they're God. People that use drugs as a lighthearted escape, but then get addicted to it and then let it change their life and shape their life around getting more of the drug. I'm so driven by these things - by avoiding these things.
Derek Sivers
So yeah, and then same with role models on the flip side, the heroes. I think it's wonderful to straight up emulate your heroes because don't worry that you're going to be exactly like them. We're all imperfect mirrors. Even if I tried to be Seth Godin exactly, I would never be Seth Godin exactly because I'm just different. It's advice for musicians too. If you love Taylor Swift, go try to imitate Taylor Swift exactly. Guess what? You won't be able to do it. She's her, you're you. By you trying to imitate her exactly, you'll just be revealing your own fun house mirror and the ways that you were warped and create something unique anyway. So go ahead and imitate your heroes and definitely don't underestimate the power of propulsion away from your anti-heroes.
Dan Riley
Yeah, I love that idea of not giving as much time as necessary to focusing on anti-heroes. And I wonder if we can focus on that a little bit more. You mentioned egotist and hedonist. And I think for both, they can be a dangerous path through the jungle for people that have tasted at least a little bit of success. And I wonder for yourself, I don't know how much thought you've given to this, but those two paths, the egotist and the hedonist, what is it about that experience, that journey, that path taken that is so repellent to you? What have you seen that you find so distasteful and worthy of avoiding?
Derek Sivers
The two have something in common, which is that they are both paths to stop learning and stop growing. So the egotist believes all the compliments and believes that they are just higher than everyone else. They are smarter than everyone else. They're more talented than everyone else. They just are more valuable than everyone else. And because of that, you just see yourself as done learning. You're at the tip of the pyramid and everybody else is below you. So you don't listen as much. You don't consider other points of view because you think the ones you have are already the best they could be. So it's very important to me to keep learning and growing in life. And so the egotist is not only on the path to stop learning, but also is just cruel and inconsiderate to others around them. Because if you just think that you're higher, then unfortunately that means that consciously or not, you think other people are lower and you don't give other people as much attention as they deserve. And people eventually shy away from you once they can't get anything from you in a transactional way. And it's a path to lose friends and live a really sad, lonely, egotistical life. Living in Los Angeles, I met a lot of these types, formerly famous rock stars, fading movie stars, I had meals with these people and got to know them and saw how they treated others. And it's just a path to misery. But more important to me, this lack of learning.
Derek Sivers
And same with the hedonism, that you could say, "Wow, I've got a million dollars now. I can afford the penthouse suite at the top of the Hyatt Waikiki!" or whatever. And people go and spend thousands of dollars a night on some fancy thing. And "I'm gonna have the fanciest meal brought right to me." I just look at them going, "What are you doing? You already have all this pleasure. What are you optimizing for 9.8 versus 9.9 pleasure?" But it's just shallow pleasure. And you're losing that deeper sense of learning and growing or the longer term vision of you're not done. You're 38, you're 45, you're not done. You're only halfway there. There is so far to go that I just still see all of these hedonistic pleasures as an obstacle to real growth.
Dan Riley
There's a great section from your new book, Useful Not True that I was reviewing right before we kicked this off where it reminded me of what you were just talking, particularly about the ego test of when someone is contradicted or comes in contact with someone who disagrees with their beliefs and they scream out, they get all upset because somebody disagrees with them. And your point was basically that it isn't that what they think is true objectively, their beliefs are not true objectively, but their identity depends on other people agreeing with them. That seems to be why, God, I see this all the time in our country, sorry, in America, your country of birth, constantly where people won't speak to each other because they need to have a certain framework reinforced. I don't know if there's anything else you want to add to that but that section of your book came to mind immediately when you were talking about people not growing, not listening anymore, not understanding other people's perspectives.
Derek Sivers
There's a beautiful idea of keeping your identity small - to not be a loud identity - to say, "This is what I stand for! I am on team blue! I believe in all these things and I'm gonna fight for this cause!" Okay, that's fine, if that works for you, like we said about the goals and the lightning bolt of inspiration that helps you jump into action, if that goal works for you and helps you jump into action, okay, great. But it helps to detach from that identity a little bit and to value change. If you think of change as growth, then changing your mind is the growth of your mind. And it helps to have a smaller identity so that if somebody with an opposing point of view says, "Actually, I think you're wrong on this point." Instead of you saying, "What, how dare you say I'm wrong?" You say, "Really? Okay, please tell me! I'd love to hear that I'm wrong on this point. That would be amazing. If at the end of the night, I've changed my mind, that would be an amazing day today. So please change my mind on this subject." And to not say that as some bullshit, you know, "Yeah, let's see you try to knock me off this post", but sincere desire to want to change your mind.
Derek Sivers
You might've noticed, I've been talking a lot about this lately, how when my boy said that he wanted a pet rat, maybe not knowing that in my past, I have killed so many rats. I used to live in a basement apartment down by the trash room and rats were the bane of my existence. Every night I'd come home, there'd be rats on the stairs and rats literally in front of my door, rats in my ceiling that I'd hear walking at night, just, I killed so many rats that year with great malice and revenge. And so for my boy to say, can we get a pet rat? I went, ew, no, hell no, I thought he was kidding. And then a week later he said, no, really dad, I really want a pet rat. Look at these videos, they're really sweet and they're clean and you can train them and they're cuddly. And I went, okay, let me see the videos. And I looked at these YouTube videos, I went, oh my gosh, wow, all right. I think I'm having my mind changed about rats right now. And he wanted it so badly, we thought about it for another week and then we got two pet rats and I love them. They're so sweet. But more than anything, I love that feeling of having changed my mind and reversed a prejudice.
Derek Sivers
Same thing with Dubai, I hated Dubai until I learned more about it. Same thing with certain kinds of music, certain foods that I said, no, yuck, I just hate that. And somebody said, come on, have you tried it? And I went, no, I haven't tried it, but I hate it. They make me try it and I go, oh, okay, actually that's really good. And how wonderful that feeling of changing your mind, it to me represents growth. So I really do want everyone to change my mind on everything I can.
Dan Riley
It's the rarest thing in the world these days to come across people with that attitude.
Derek Sivers
But it shouldn't be. If we let go of this social signaling: "This is who I am and I'm always right! But if you think of yourself more as a student instead of a preacher, and you think of yourself as somebody who wants a growth instead of somebody who's done and complete, then it should be more common.
Dan Riley
Yeah, I think I heard you say in an interview I came across that your definition of stupid is someone who stops thinking. That they have basically blocked themselves off from alternative perspectives or different information than what they've been exposed to. I'd love to give you an opportunity to expound on that if you'd like about how you think about stupidity and how it relates to what we've just been talking about.
Derek Sivers
Sure, there's no such thing as a stupid person. Nobody is stupid. They're just people being stupid. Somebody who might be objectively a very smart person can still be stupid and say stupid things on Twitter. And you have to catch yourself then to not just categorize people like "This is a stupid person, that is a smart person." And instead judge the actions. Was that action smart or stupid? So to me, the main stupid action that people do is to stop thinking. If they just say things like, "Well, you know, Arabs are just like that. That's just how Arabs are. That's it. That's why that person acted that way." What they're doing is saying, "I don't want it and I'm not gonna think about that. I'm done. There will be no more thinking." So that is being stupid. Whereas being smart then would be to say, "But why? Hold on. First, let's not over categorize. Let's not over generalize. And let's get to specifics. Why is somebody acting that way? Why are you reacting to it like that? Why are you judging this as bad or good? Is it because there's some empirical evidence that everyone would agree this is bad? Or is this some value system? And if it's your value system, where did you get that value system from? And is it a value system that is for a certain goal? There are certain value systems that would lead you to be a good soldier and a different value system that would lead you to be a good artist. So perhaps do you have a value system that's different from the people that you're judging? And you can see that this person you're judging has different values in life than you because they have different goals?" Well, just talking about this, now you're being smarter to talk about this instead of punting and generalizing and being stupid.
Dan Riley
So much of this to me is about maintaining openness. And I'm sure because of how much you read that you've come across the big five personality traits, the ocean acronym in assessing human personality and psychology and that the O in the ocean, ocean is openness, conscientiousness, extroversion, agreeableness and neuroticism. And the O in openness to me, that's what I hear a lot of in that response. And my understanding is that predictably, people that quality reduces typically as people age. And it's something that I may as well just read this now or bring this up now, because it was an idea that I loved in researching this conversation about how for yourself, we talked about these moments in your life where you obtained, I think it was a few million dollars before donating $22 million and how you wanted in your life to prioritize personal growth over status and wealth growth. And to me, a lot of this is interrelated that you have a life that is encouraging of that kind of growth. You seemingly have had a lot of intention around wanting to cultivate a mind that is open and is trying to see the world more clearly from as many perspectives as you can. I don't know if you agree with that, but I wanted to put that to you and talk about that, the prioritizing personal growth over wealth growth and status growth, which is again, so unusual people tend to just stay on that track where they have been successful rather than getting off and moving into prioritizing other areas of your life. I wonder if you have any comments on that.
Derek Sivers
Sure, I mean, well, first let's not fault people for whatever path works for them. If continuing to try to make another million dollars every single day is what drives you to do great things in life, invent new things, start new companies, good for you. If that's what works for you, that's great. I'm not against that. Same thing with status growth. If constantly seeking status is what makes you bounce out of bed in the morning, and if it's not objectively hurting the world and it works for you, then great. So, again, I'm not against it.
Derek Sivers
But kind of like fitness, where if you don't actively pursue it, then it diminishes through inaction. If you're not actively doing something to get fit, you will get weaker and weaker and weaker. I think it's the same thing with openness. And it's the same thing with growth. That if you're not deliberately, consciously taking actions to open your mind, then just through inaction, your mind gets more closed over time, just through time and habits. "Well, this is just how I do things. This is the way I like my eggs. This is where I live. This is what I do. This is who I am." If you don't actively work to open those up, through inaction, you'll get more and more closed. And I don't want that. If somebody else wants that, good for them. I don't want to get smaller and smaller and more closed in life. I want to keep growing. So I have to deliberately pursue openness. I have to lean into my prejudices - if notice I'm prejudiced against something, I steer towards it instead of away from it in order to learn more about it, because that is a strategy to keep being more and more open.
Derek Sivers
And same thing with personal growth. And by personal growth, I mean, whether it's say the skills you have, the knowledge you have, if you just think of growth as something that happens in your teens and 20s, and then you hit 35 and you say, "That's it. This is who I am." Well, again, that's like fitness. You're going to get weaker and weaker through time. You're going to get, what is anti-growth, shrinking? You're going to shrink just through inaction in time. So yeah, I very deliberately, like fitness, do the work. I'd say every day, but at least every week, I do the work to try to challenge myself and be more open, just to stave off the shrinkage that would happen through inattention.
Dan Riley
I quoted this man earlier at the beginning of our conversation, Kevin Kelly. And there's a section in his book, Excellent Advice for Living, where he talks about how this very concept, and he's a man who has lived many lives in a very open life, lived a lot of his life in Asia. And he noted that even for people who are trying to be open, people need a degree of stability and routine. And in his mind, what had worked for him was two thirds of his life was routine, going to restaurants he liked, eating foods that he knew were delicious and healthy, having similar habits, and a third of his life introducing complete randomness, going out and trying new things as a mechanism for growth. I wonder for you if, and I know you said, you don't know other people's minds, no one does, but is it your hunch that the prioritizing, the reduction of the winnowing effect, trying to consciously stay open and stay growing and curious would be generally a beneficial habit to adopt for more people, given what I know you and I must both know about the rates of depression and listlessness and loneliness in people's lives. In your mind, do you think that that's something that more people may benefit from incorporating into their life, or are you just really focused on an N of one yourself?
Derek Sivers
I'm just focused on myself, but yes, most things I say, hey, who am I to say what others should do? But I think you're right, that this is something that basically everyone could really benefit from. But let's not forget that a lot of people are just overwhelmed with the day-to-day trying to get through their day, trying to get through the week, just trying to get to Friday to get their work done. They're overwhelmed. All they can think about is this week. They're not thinking longer lifelong strategies. So I understand that some people need to be extremely narrow focused, the blinders on just to get through this week. They don't wanna open their mind to new ideas and suddenly start to learn how to speak Estonian or something, no, "I'm just trying to get through my week. Shut up with your open-minded crap, you luxurious retired dude." But yes, I do actually think that it would benefit basically everyone, even if like exercising, weightlifting, it hurts and it's inconvenient, but damn it feels good after you're done. Opening your mind deliberately - and steering towards the things you're prejudiced against - is hard work, but damn it feels good when you reverse a prejudice, when you start appreciating something you used to despise through ignorance, it feels amazing. And it becomes symbolic in your life then to say, "Wow, if I reversed my prejudice on that, what other things am I prejudiced against that I could also steer towards?" I think it could be symbolic and really powerful for basically anyone.
Dan Riley
I wanna read a quote that is related to all of this. And this is from you about learning and growing. The quote is, "You really learn only when you're surprised. "If you're not surprised, then everything is fitting into your existing thought patterns. So to get smarter, you need to get surprised, think in new ways and deeply understand different perspectives." Now, I have heard people who have spoken to you about a lot of these different topics, about staying open, about changing your mind, about reducing the prejudice you may have against cities or groups of people or ideas in general. I wonder for yourself to flip it around, are there, because that's a very kumbaya outlook on life, that everything can be understood and appreciated and respected. Do you think there are still systems in place of the way in which people are being ruled in this world, whether that's modern slaves or women who are experiencing FGM in certain areas of the world, where do you draw the line personally around, at least at this point in your life, of being open to a new perspective and really just as a human being who wants other people to be well and happy and prosperous, that there are things in this world that you are not okay with? I'm not sure I've ever heard anyone ask you that, but I've always been curious where you stand on that at this point.
Derek Sivers
There are plenty of things that I don't like. But it helps to try to understand them as much as you can first, instead of "knowing" that you're against it based on just a few sentences. Or because of what one person told you or one thing you heard, you're against it. I think it's way more challenging and interesting to try to hear out the people that are somehow for it and say, "Okay, please explain. Tell me what value system leads you to think that this is the way." Though that can be persuasive in the moment. A charming person can explain their point of view, like a charming villain in a movie that it's a brilliant movie-making technique where they get you to empathize with the villain, instead of just cartoonishly oversimplifying them as just evil, when they try to show you the villain's point of view, and that leads them to do bad things. But while you're watching it, you go, "God, yeah, I get it. Maybe I would have done the same thing if I were in their shoes." And only later, it takes a couple days to go, "No, even though I get it, it's still just bad." Then you can catch this in yourself. Sometimes you can say things that sound like they make sense and they're rational, but still lead you to do what zoomed out is a bad thing. So revenge is classic for that. "I'm not gonna stand for this. This person looked at me and said this, and I just, you know what I did? I just, I threw the milk in his face and I stormed out and I broke the glass on the way because he needed to know that that was wrong behavior and I wanted to make a point or I needed to protect my honor, self-respect. I couldn't respect myself if I didn't do that." And they explain it like it makes sense. And maybe if you care about this person, you might even for a second empathize, but then you go, "No, that's just the wrong behavior. That's just objectively bad." So yeah, I try to get it down to the individual level.
Derek Sivers
We could try to talk about the caste system in India, but let's get down to the individuals where a person is choosing to treat another person poorly. And what is it in that moment? Why did you treat the person poorly? It takes no more energy to not be cruel, to just be kind instead of cruel. It's not more difficult. So why are you choosing to do that? What's in your value system? Is this something about your self worth that you can only see yourself as higher if others are lower or where is that coming from? I find it more useful to get into the individual level instead of oversimplifying.
Dan Riley
Are there, for an individual, are there beliefs or lifestyles that at this point, even if, like you said in the moment, a charming, articulate quasi-villain or villain might be persuasive in the moment? Is there anything that comes to mind that you've come across that you still, and again, these are not being prejudiced against a city like Dubai. This is something else. I don't know if anything comes to mind where you're fairly confident that your prejudice is well placed and will probably be firm for your life? And maybe not.
Derek Sivers
I have a problem with public figures, like very famous, high profile people that are deliberately cruel and rude in public, even if it benefits them for political office. And I'm not just talking about America right now. I'm actually also thinking of examples that I've seen in India and elsewhere, that someone will blanket prejudice against one group of people because they know that it will get them more votes from the other group of people. And they justify their action through that. That even could just mean even snarky tweets. They can go, "Ha ha ha, well, you know, that unifies their fans." But it has knock-on effects that are multi-generational for legitimizing cruelty that grandchildren will see. And then their generation will continue 80 years from now to be cruel to this group of people because as kids, they saw it as a success strategy for somebody. And so then it perpetuates for multi-generations, all because this individual was trying to get more likes on their platform. So they were cruel to somebody and God, that shit has such long-term effects that that, I'm completely against that no matter what present benefits somebody tries to tell me it has.
Dan Riley
Yeah, I would echo that as well. I don't know if you're open to this, but one of the things I remember from our first conversation that we talked about, and I don't hear you talking a lot about your life or your personal life, but as a long-time fan of yours, I have often wondered how you would think about various aspects of life, of one's personal life. And we talked in our first conversation about, you phrase it in an interesting way, which I'd never heard of before, which is the problem of an optimist. You were talking about a relationship that you had been in for many years that had come to an end. And if you're not comfortable talking about it, I totally understand.
Derek Sivers
I'm open. Ask anything. I'm challenging myself more to talk about these things.
Dan Riley
Here's a quote from that conversation that I wanted to read out and go from there. Correct me where I'm wrong about any of this, but this is a live-in girlfriend of yours. For many years, you were considering, I think you were engaged to be married, were planning to have kids with her, and there was just a consistent, I don't know if they were overt fights or just friction there with her. And the line you said, you asked for a few days to go by yourself and consult your journal, which you had been writing in, I think daily for years. This is a very ingrained habit for yourself, I think for moments like this and for honesty and reflection and trying to make good decisions. And you ended up deciding to break up, to call off the engagement. And the line you said afterwards to me, which I wanna quote is, "It had always been hard, but my optimist memory made me think it was only right now. In general, it's great, but right now it's tough. But it turns out that almost the whole time, it had been tough." You can take that wherever you would like, but I really like that framing of the sort of the optimist dilemma. And if there's anything else that comes to mind about getting real with your study, obviously there's a cultural understanding about the negativity of depression and people that have a negative hue on everything. But I have seen this in my life with close friends, sometimes with myself of very optimistic people also having their own bias that needs to be checked. Just wanted to put that to you and have you comment on that in any way you would like.
Derek Sivers
Sure. For that specific story about that relationship, I don't think I have anything more to say about that. Not out of privacy, but I think that was the lesson from that moment.
Derek Sivers
But something that has happened along those lines since we last spoke is the downside of my optimism towards other people, assuming the best in everyone, trusting everyone by default. This got me screwed just six months ago when a house builder that I had a good relationship with and he was close partners with the architecture firm that I'm working with. And he had come recommended from somebody that I trusted. And we all have this little happy family. This was my team, this was my builder, this was my architect. We're building this house, we're doing this thing. We had met up multiple times, had multiple references, whatever. And then the builder said, "All right, so in order to do this, "I'm gonna need a $20,000 deposit to lock in the time to do this." And I went, "All right, well, you're my guy, let's do it." Gave him the $20,000. And literally a few days later, he declared bankruptcy. And this implies that he knew when asking me for the $20,000 that this was not a deposit, that he was deliberately screwing me, that he was getting my 20,000 to pay off some other people that maybe he was better friends with. So that, you know, "Fuck you, Derek. I'm deliberately screwing you very intentionally in order to benefit somebody else." And it was just devastating. I contacted a lawyer, they said, "No, there's nothing you can do, you know, bankruptcy. That's that." And then even contacted the architect that we were working with. And he said, "Yeah, Jeremy's a great builder, but a bad businessman." And he said, "I'm sorry to say, it sounds like he very deliberately screwed you. There was no way to justify it from his point of view. It's not like that $20,000 was to buy materials tomorrow." He said, "If you would have asked me about it, I would have said, no, don't give him that deposit." Even before I knew he was gonna declare bankruptcy, you don't give somebody deposit unless it's for a specific thing. So, sorry, I'm going into too many details. Point is, it's made me think about, the default optimism of trusting everybody.
Derek Sivers
By the way, I just wanna get into the transcript of the conversation, Kevin Kelly is one of my top five heroes in my life. I think of him all the time. He's a very deliberate role model for me. I want to be like Kevin Kelly. He's a straight up hero. It was great when I finally met him years ago in India, and I just went running up to him and was like, "Oh my God, Kevin Kelly." And one of his questions was, "What are you trying to optimize your life for?" And I said, "Well, honestly, I wanna be like you." And that was the start of our friendship. So, we've spent quite a few days together now. And yeah, I love getting to know my role models. It's such a treat.
Derek Sivers
Okay, one of my other role models that I got to know very well is Erika Lemay, who is an acrobat in short, although it's oversimplifying. She does performance art, aerial performance art. She's a hero of mine because she has found the perfect balance of graceful distrust. Because her career has her hanging from ropes where one slip up and she dies. And four of her friends have died from such slip ups. She doesn't trust anybody, but she's graceful about it. She's kind, but distrustful. She's pleasant and polite, but show me double proof. Let's put that into writing. And what is the backup plan when this fails? And who else is going to check your work to make sure that what you say happens and what assurances do I have? And I will not proceed unless I have all of the assurances in the world. She and I were out to dinner in Sicily at a really nice restaurant where the waiter was super nice, the staff was super nice. And after the end of the meal, they said, "Oh, should we get you a taxi home?" And we said, "Yes." And she speaks fluent Italian, so we walk out of the restaurant and the guy at the restaurant said, "There's your taxi, he's waiting for you. He'll take you home." And she said, "Give me a minute." And she walked up to the taxi and said something in Italian, and then the guy drove off. I said, "What was that? What happened?" And she said, "I asked to see his medallion. He could not show me his medallion." And this mindset blew my mind: She said, "You know how these things go. Oh, the nice man at the restaurant. Isn't he so nice? Oh, his friend brings you home. And in bringing us home brings us through a dark alleyway where two people come out and mug us and pretend to mug the driver too. And the driver goes, 'Oh my God, what a horrible situation.' But of course they were all in on it. And then they split the money. So no, I didn't see his licensed medallion. So we'll just walk a little farther to the Plaza and get a licensed taxi." I went, "Whoa, how do you even think like that?" And not be bitter, not be rude, but to continue to be graceful and kind, but distrustful? That's still the balance I'm trying to find. And I've clearly been burned by not having that yet.
Dan Riley
Do you feel like you are approaching that level of graceful distrust? Is that a work in project or in progress for you?
Derek Sivers
Mm, slowly. It does not come naturally to me. It blew my mind getting to know her and seeing that in action.
Dan Riley
I don't know if you're comfortable talking about this, but I have always been interested in learning more about your life, your life with your wives, your girlfriends.
Derek Sivers
"Wives" makes it sound horrible!
Dan Riley
Yeah, sorry. I don't know how many times, I think it's twice you've been married?
Derek Sivers
Neither time for real. To be clear, both times were just a bit of technicality so that she could travel. The first one was, she was my girlfriend from Sweden, and we were together for a few years and she kept coming over to visit for six months at a time and just maxing out the tourist visa. And the third time she did it, the guy at the airport said, "Look, you're not allowed in here again unless you've got a work visa or you're married or something, 'cause you're clearly, you're going too much, using the tourist visa too much. So I'm gonna let you in this one last time, but I put a note here on your record. You're not allowed in America again unless you get a proper visa." So I actually tried to get my company to hire her because we didn't want to get married. We knew that we weren't like life partners, but she was my girlfriend. I loved her, I wanted to be with her, but forever was a different conversation. So I did a lot of work and spent thousands of dollars on lawyers to try to get her a work visa, but it was gonna take years and that meant I wasn't gonna be able to see her for years. So instead we went down to the county clerk's office and signed the piece of paper. "There. Now, can you not kick her out?" So that was my first marriage. And it was a great relationship for six and a half years. And then we just like naturally went our separate ways and it was wonderful.
Derek Sivers
And then the next one that I told you about earlier with the flight was again, her parents said that she couldn't travel with me unless we were married. And I wanted to leave America forever. So that means travel. And I said, "Well, we'd only known each other for nine months." I thought, "Well, let's see what happens." All right, fine, "There, signed the piece of paper. Now can she go?" So those are my two marriages. Neither one was intended to be life partners.
Dan Riley
And I know, I mean, just from knowing you for so many years and the lifestyle you have led is to me so exciting and interesting and you've lived in so many different countries. And I don't know in that many years journey, I know you've been in New Zealand for a long time. If you have felt like you wanted to have, you know, girlfriends in your life at that time, I know you've prioritized freedom and independence, but how do you think about that, the role of women and girlfriends and potentially longer term partners in your life, given your propensity for growth, for travel, for freedom? The two often do not go well together in my experience. And I think in many people's experience... I don't think I've ever heard you speak about this. In your life and your experience of prioritizing either how they work together, don't work together, the role of prioritizing women in your life. I'd love to give you an opportunity to talk about that and what you've learned from your many years on the road and traveling and being in many different countries.
Derek Sivers
It's funny, the role of women in my life is almost everything! Because the first best friend I ever had at the age of 12 was a girl. Sharon Danesi was basically the start of my life, like the start of my conscious memory and feeling like I am who I am, started with the deep, deep friendship with Sharon Danesi from age 12 to 17. We were inseparable best friends, totally platonic, nothing romantic at all ever, she was like my sister. But damn, we were such good friends. And then at the age of 17 or so, so she moved off to Italy and we lost touch.
Derek Sivers
But then at the age of 19 or so, I met my next best friend, Meredith, she was my roommate's girlfriend. And so she was just over all the time and we just clicked and hit it off and just became inseparable best friends for 18 years. Meredith and I talked many times a day. We lived together a few times, we were roommates, just like if one of us was moving to a new city that the other one already lived in, we were roommates a few times, just inseparable best friends. And then she got married and we kind of drifted apart.
Derek Sivers
Basically, point is, all of my best friends have always been women, 100%. Not even 99%, 100%.
Derek Sivers
So, romance is a different kind of relationship that has this kind of animal attraction with it as well. And so I've had lots of those, and I would have liked to have found a life partner to learn and grow with. And I had a couple really wonderful long relationships. I had two long relationships, we were like six and a half years each. That one was the Swedish girl that we got married as a technicality. She was great, we had this great relationship for six and a half years, totally nourishing and healthy and just wonderful. And then it was just different life paths. I just wanted to work and she just wanted to be in the LA scene and I wanted to be up in Portland working. So we just kind of said this sweet goodbye and never saw each other again. And that was it. And it's funny when people say, "Oh, It's a shame that relationship failed or it didn't work out." And I say, "No, it didn't fail, it was wonderful!" Just 'cause something doesn't last forever doesn't mean that it fails! Not every relationship is meant to last forever.
Derek Sivers
The first one I had though, I thought it was gonna last forever. And I was devastated when she dumped me after six years. But we've stayed friends over the years. And now in hindsight, I'm like, "Whew, God, I'm glad she dumped me. That would have sucked to still be with her." 'Cause we're ultimately a real clash of values. But no, I've looked, I've tried. I think it's a bit of a, just a bit of a life failure for me that I haven't found somebody that feels like a real life partner. But instead I've just had great long relationships and great friends.
Derek Sivers
And I'm very open to it. Except that like we said at the beginning, I just wanna work all the time. I'm just not a leisure person. Just 5 a.m. to 11 p.m. I'm working and I love it. I just wanna be doing my thing all the time. I can't hang with a lifestyle that just means six hours a day of sitting around on couches, watching TV. I just don't want that. But yeah, I don't know.... There are very few people that are the same way and don't want leisure.
Dan Riley
And I think you've just answered that, but given your preferred lifestyle, that's been difficult I would imagine. It's tough to find somebody who aligns with that level of workload and lifestyle choices. Is that fair?
Derek Sivers
Yeah. I did meet someone once that I thought was a perfect fit and it's somebody I've mentioned earlier in this conversation, but it didn't quite work out. But they are out there somewhere. It's not a big priority in my life. As you can tell, I wake up bolting out of bed, excited about what I'm doing. I have great friends and I'm just not yearning for a life partner.
Dan Riley
You have a full life.
Derek Sivers
Yeah. I mean, we haven't mentioned my kid, but oh my God, like the exception to so much of what I've said earlier. My kid and I spend 30 hours a week together, just one-on-one undivided attention, usually with him leading the way and me being his patient sidekick in his adventures. I mean, 30 hours a week, just giving him my full attention. It's a lot. There's not a lot of room left over after that and work.
Dan Riley
Yeah. I know we're getting close to an hour and a half, so I don't wanna take up too much of your time. Maybe we can do another few minutes if you're open to it.
Derek Sivers
Yeah, I've got no cutoff.
Dan Riley
Okay, maybe we can close on your most recent book "Useful Not True". We've alluded to some of the concepts in the book. Before we do, I wanna make sure that we get this kind of recorded for today's conversation about something I wanted to talk to you in our first chat, which is about what you learned from givewell.org about what it takes to save a human life. And I actually just learned this today, that the 22 million that you put in a charitable trust, which has been growing and will be donated upon your death, which probably will be many multiples of what you put in that trust initially, will be donated. My understanding is to GiveWell, which is associated with the Against Malaria Foundation. I wanted to put the subject to you about what you have learned in your research. I also know it doesn't sound like the philanthropy world is that interesting to you, just as you're being extraordinarily generous with how much of an impact you're gonna have, but you don't spend a lot of time researching these subjects from what I understand. But I wanna talk about that incredible fact that I heard you say on a podcast once that with, I think it's roughly $2,000, anyone can reasonably believe that they have saved a human life with that amount. And anything else you wanna say about the importance of keeping that in mind in your life and anything else that may come to mind about that subject?
Derek Sivers
Yeah, that really messes with your sense of value when you learn that. And the idea is it's not just the Against Malaria Foundation but a few different efficient charities that are saving people's lives. The idea is to be clear, and again, yeah, like you said, I'm no expert in this. I'm not the data nerd that goes into all the statistics. I defer that to the nerds that do nerd out on it. But the nerds that do nerd out on it say that for every $2,000 that you give to buy malaria nets, that this many cases of malaria are prevented, which therefore saves this many lives. Like not every case of malaria leads to death, but if you prevent, say, 1000 people from getting malaria, statistically, maybe two of them would have died. And so by giving this much to pay for nets, you are saving this many lives. Once I learned that, ooh, you start to look at $2,000 very differently. You mentioned earlier, yeah, economy versus business class. I think, okay, so I could be more comfortable for 12 hours, but two people will die? Hmm. And whenever I say this, almost everybody I mention that to, pushes back right away. They're like, "Yeah, but you know, come on. You gotta have comfort. You can't just completely sacrifice yourself for others." But I guess everybody draws that line where they want to, and it's definitely moved the line for me to learn about this. I hear about things that technically I could afford, a fancy thing that I could buy, and I just think of it in terms of how many lives will be lost because I bought that thing instead of donating it to the people that are saving lives. Then somebody says, "Well, then if you don't donate that money to saving the life instead, then it's all just moot anyway! You're not saving the life. You're just stopping yourself from buying the thing and then just keeping the money." I say, "That's a really good point!" It's a good reminder to keep giving if you really are being steered by this value.
Dan Riley
You have maintained that concern for people that, I guess I should just speak for myself, that I think as I've gotten older, that fact, that desire to help people who are less fortunate than I am, it's easy to have that begin to fade away, I think, as you don't interact with people who are struggling. And I wonder for yourself, I was thinking about a recent podcast guest I had, Pico Iyer, I don't know if you know that name.
Derek Sivers
Of course! I love him!
Dan Riley
You remind me of Pico in a lot of ways, honestly. Your writing style, your energy, he's such a lovely man. He just wrote a book about silence called "A Flame." And it's about his 100 plus experiences going to a Benedictine hermitage in Big Sur throughout his life. And living with monks in this beautiful landscape in the middle of nowhere where no one is there except for the few people that live on this compound. And the point is to be in silence for the duration of your stay and how important that has been for such a busy, interesting, cosmopolitan man. And I wonder if you think that concern for strangers you'll never meet is buoyed in you because of the time you intentionally spend in solitude. I'm projecting a little bit because for me, that's a lot of when a lot of my more, I think, decent moral sentiments come out rather than the stress of a normal day. I don't know how you think about that if the space you've carved out for solitude has helped you grow your heart or maintain your heart to care about people that you'll probably never meet.
Derek Sivers
Thanks, I'd never heard that idea before. If that's the case, I'm completely unaware of it. And it doesn't feel like that's the case. My hunch is no.
Derek Sivers
I'm not actually that empathetic of a person. I'm not very altruistic. It's just common sense to me that if I have a hundred cupcakes and I know I'm only gonna eat two, well then you don't just hoard the other 98. You pass them around because people like cupcakes. So I feel like this with money where if I know what I need to live but I've somehow been given way more cupcakes than I can eat, it's just basic one-on-one common sense to just give them to people that need them. And it's not coming through some giant, dripping, bleeding heart. It's just common sense. I'm actually not that empathetic.
Derek Sivers
When people do this empathy thing, I'm gonna say something bad about myself right now, is I've read these books about veganism that try to make your heart swell when they show, look at the poor pig living in the confines of the small thing. I read that with an open heart and I even look at the pictures and the videos, I'm like, just not feeling it. And it's the same thing with a lot of other things that people try to do to stir empathy. I'm like, feel it a little bit, but I'm just not a super empathetic person. I'm not a sociopath, but that's not the reason I'm doing it to me. It's more just rational common sense, which is why it makes more sense for me to find an organization like GiveWell that's filled with charity nerds that are actually crunching the numbers to find out which organizations are saving the most lives per dollar given, which also, by the way, in their algorithm, it has to factor how much this organization still needs money. Like if you give money to the Red Cross right now, they've got billions in savings, giving them $100 won't make a difference, but there are still organizations that if you give them another $100, it will be immediately put to use to save people now. And they're very charity neutral. So yes, they recommended the Against Malaria Foundation two years ago when I was giving, but who knows, I might look at the website today and it'll be a different foundation 'cause maybe the Against Malaria Foundation has enough money now and they'd say, actually, here's a bigger problem right now. The money spent towards this will save the most lives today. So I'm open to just whatever will save the most lives without some swollen heart leaning towards a particular cause that then would feel weirdly egotistical and selfish to me to put into that. Although I'm glad that some do. If somebody really has a cause to save these trees or save these piglets, then I'm really glad that they do. But for me, because I'm not leaning so much one direction, I just am happy to give it to the people that crunch the numbers and tell me where my unneeded money is best used.
Dan Riley
Would you group that into the deep happy component of your life or is it more, as you just said, the rational, I've got 100 cupcakes, I'm only gonna eat two, here's 98 of them?
Derek Sivers
Yeah, it's not even a source of deep happiness for me. No, it's just rational.
Dan Riley
Interesting. I would love to close with your new book and get the just sort of maybe a high level take from you about Useful Not True, which I've been reading over the last couple of days. I wanna set the table with a quote, which I kept coming back to about Useful Not True. I think that I was reluctant to read the book initially because of the title Useful Not True. As somebody who is trying to find the truth, I think my own pride was reluctant to seek out a book that was trying to potentially dispel the truths that I may hold about the world. And this line actually really helped clarify what I think you mean by Useful Not True. Obviously, please add anything you would like to it. But this is probably a third of the way in the book where you have this quote, "Remember, not true does not mean false, "but just not the only answer." And I don't know if there's anything you wanna add to that or additional context you wanna provide about the book Useful Not True, where it comes from, why you wrote it, why you think it matters.
Derek Sivers
Thanks for telling me that. That helps to hear.
Dan Riley
It does define in the very first page of the book that yes, but when I say the word "true", it's shorthand for "necessarily, absolutely, objectively, empirically, observably true for everyone, everywhere, always." And if it matches all those criteria, we can call it true. And the reason to set that bar so high is because once you define something as true, it's closed. No questioning. It's a fact and that's that. We're done thinking about that. It's just true. So the point of raising the bar that high is to help you see all of these other things that are true-ish, but not necessarily true for everyone, everywhere, always. So things like morals and values and obligations and stories that you've told about your past, your self-identity, all of these things are still negotiable. You've been telling a story about your childhood. You've been telling a story about that person that wronged you. You've been telling a story about who you are in life and what you're doing. And you say it like just a fact, like, this is me. I'm this many inches high. This is my age. And this is my childhood. And this is where I'm going. It's like, well, hold on a second. Your name and your height, those are facts. Your childhood, that's a perspective. Let's not intertwine these things and think that because you rattled them all off as who you are, that they're all true. This story you've been telling about you being an unpopular kid in high school or whatever, I don't think that's necessarily the only way to look at that. This story you're telling about what you're good at and what you're bad at, that's not an absolute fact. That's worth looking at again. That's still negotiable. So that's the reason for setting the bar so high.
Derek Sivers
And then the flip side of that is once you realize that certain thought patterns lead you to certain actions, then you can deliberately choose your beliefs just because they create the actions in yourself that you need. So if you need to help yourself get out of bed in the morning, you can adopt a certain belief that says, it's great for me to start early. If I start my day early and get an early start on the day, I'm gonna be successful in life and I'm gonna be healthy. I'm gonna be a good person. But on the other hand, maybe you don't get enough sleep. And the belief that you need in the morning is like, it's 5 a.m., no, I need more sleep. Sleep is the healthiest thing I can do for my body. Go back to sleep. So conflicting beliefs that you would adopt and not because either one is necessarily absolutely empirically observably true for everyone everywhere always, but it's the belief that you need in that moment to help you generate the action that you needed, which is either to get up and get going or to get more sleep. And these just come up a hundred times a day in everyone's life. We choose the belief that helps us do what we need to do.
Dan Riley
Do you see a lot of overlap between this book and I forget if it's the beginning or the end, I think it's the end of "How to Live" where you have the 27 different instruments. These 27 different chapters are basically, it's an a la carte option for beliefs to adopt in a certain context that may help you thrive, do better in life, et cetera. How do you see the parallels between those two books?
Derek Sivers
I didn't intend for this new book to be a prequel to my last book, but as I was writing it, I realized it is because my last book called "How to Live", I just put that weird book out into the world with no explanation. I went, all right, everybody, here's my weird book. Do with it what you will. And yes, it's 27 chapters, each one very opinionated and telling you, this is how to live. You must live for the present. Living for the present is the right way to live and here's why and stacked up the reasons and this is the way to live. The very next chapter said, live for the future. Forget the present. Everything you're doing is serving the future and it stacks up these arguments. And then the next chapter is, here's how to live, get rich. It's the only worthy thing to do in life because money is a neutral representation of value. So by pursuing money, you're pursuing being valuable to others. It's the most generous thing you could do with your life, stack up the reasons. And it's a weird book to just have these 27 chapters back to back and then there's basically no explanation except that the end, there's just two pictures. One of a duck and bunny, you know, optical illusion, is it a duck or a bunny? And then one that's just like you said, the orchestra seating chart, which if you count, there are 27 instruments. Surprise, surprise, or coincidence, coincidence to go with the 27 chapters.
Derek Sivers
So it wasn't until the "Useful Not True" book, the newest one, as I was writing it, I realized this is actually explaining to people why that last book was the way it was. So that's why I included the story of Stravinsky and the instruments in the orchestra. And then I just straight up explained that, yeah, there are so many ways to look at life, so many different value systems you could follow, that now having heard this, if you look again at my book, "How to Live," you'll see that this book is actually the prequel to that. So now I tell people to read "Useful Not True" first and then read "How to Live" and it'll make more sense.
Dan Riley
Hmm, maybe we can close on this, but I would love to know if you think, I can, and this is probably my, was my initial response to "Useful Not True," is that it's potentially destabilizing that it's undercutting the principles that people hold to be accurate about the world that they live in and potentially rupturing that could be challenging and difficult for people to accept. The inverse perspective on that is it's a liberating observation that you can choose the perspectives that you want in life for that given time. I would imagine you take the second perspective on this, that this is an outlook that is a liberating fact about being a human being in life in general, but I wanna ask you that. Is that where you come down on the main conclusion from "Useful Not True" or is it something else?
Derek Sivers
Oh, the main conclusion, I would say, I don't know, different people are going to get different things from it based on what aspect of this is surprising to them. Some people might read it and go, "Well, yeah, well, duh. I know I'm just choosing my beliefs." And other people might go, "No...." Like you said, the word rupture, that was a good word. Like, "You're rupturing my beliefs. No, I believe this because it's true! No, you must say being a great parent is the most important thing in the whole world that anybody on earth can do! It's the reason for living. It's the meaning of life! This is just true!" And if this book or thought ruptures that for you, then it was rupturable anyway. And I think you would eventually see that it wasn't necessarily true for everyone, everywhere, always observably, you know, any creature or alien machine could observe it and agree it's absolutely necessarily true. No, it was always one way of seeing the subject. And when you realize that it's not absolutely true, but you're choosing it, like I choose to give my kid my undivided attention whenever I can. I know that I could flitter off and be a bad dad, but I choose not to. I'm not doing it because it's an absolute truth. It's a choice for my value system, and then becomes more considered and reasoned. And I think then it becomes more sound to know that you're choosing it for these reasons. I have this value system. This is what matters to me. This is what I want my life to be. Therefore, I'm choosing this value because it creates this emotion, which then creates this action in me, and that's why I'm choosing it. Now it's sound. Now it's not rupturable. So I do hope to rupture people's beliefs that are founded only on the fact that they think it's absolutely true. And I'd like them to realize that they can continue to choose it because it's sound and it creates the actions that get them where they wanna go, help them be who they wanna be.
Dan Riley
Yeah, and maybe align more clearly with who they are as a person. That to your point, when you have thought through a belief like that that actually aligns with you, it's much more difficult to rupture it because it's genuine.
Derek Sivers
Yeah, it's considered. You're not defending it only by saying it's true, to which there's somebody somewhere in Sri Lanka or Kyrgyzstan that would argue the opposite and tell you that their belief is true, and then you're just gonna argue with each other. No, instead, if you realize that your point of view is a choice that supports these values, which support these actions, and that's what you want, then that's such a better argument than insisting that it's true.
Dan Riley
Yeah, Derek, it was so great to see you again. And when I first started this show, I forget if I told you this the first time, three and a half years ago now - this will be episode in the 140s - you were on my top five or 10 people that I wanted to connect with and have a conversation like this with at some point. And I was thinking about that when you were talking about setting goals and making the creative act and making something real. And this is one of those experiences for me. And that kind of deep satisfaction from somehow convincing you to give me an hour and a half of your time to talk about whatever I want is pretty amazing.
Derek Sivers
Well, back at you, I do a lot of interviews and you are one of the best interviewers I've ever met. I love your questions. I love your style of getting directly into the question and you keep it so challenging and interesting and informative to the listeners. So thanks for being a great host.
Dan Riley
Thanks Derek, it means a lot.