Derek Sivers

Infinite Loops - part 1

host: Jim O’Shaughnessy

problem-solving, questioning norms, execution over ideas, exploring perspectives and beliefs

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Transcript:

Jim

My guest today is Derek Sivers. You almost go beyond description Derek and I actually thought of this line from Walt Whitman that I’m going to read, because it reminded me of you. And the line, is this, “The past and present wilt. I have filled them, emptied them, and proceed to fill my next fold of future. Do I contradict myself? Fine, I contradict myself, I am large, I contain multitudes.” Derek, welcome.

Derek Sivers

Jim, coming from you, that means a lot. That is such a wonderful quote. I think of it often, so thanks for associating that with me.

Jim

Absolutely. And I got to tell you, you just are absolutely beyond intriguing to me because you’ve been a musician, a circus performer and entrepreneur, an author. You accidentally started CD Baby to help your friends sell music, turned into this huge online company where you had 150,000 musicians that you were selling. You had 100 million in sales. You sold it for $22 million. And then you gave the money away to charity, which like, wow. But all I have to do is mention you. So I mentioned you to my head of Infinite Media, whose online handle is Liberty. His real name is Michael Graham and immediately got an email back from him and he goes, “I remember the email I got from him.” And then he typed it out from memory. And so he said your confirmation email to him was, “Your CD has gently been taken by CD Baby off the shelf with sterilized, contamination free gloves. We have lovingly put it on a satin pillow. A team of 50 polished it, and then our packing specialist from Japan lit a candle and did a ceremony, and we all put it in a gold lined box. The entire company had a celebratory march to the post office, and all of Portland waved goodbye. And your photo has been placed on our best customer wall of the year.” I mean, like, dude, tell me about this. Were you always like this when you were a kid? Was this the way you were enlighten me.

Derek Sivers

I’m going to rewind a minute first and then answer the question. I suspect that you and I recognize this in each other, because I didn’t get the chance to say yet that I am so excited to talk with you. I so admire what you’re doing, and I think that you and I have this drive of continuous expansion and improvement that I think of the musical metaphor of AC/DC versus, say, Miles Davis or David Bowie, that there are some musicians, like AC/DC, that they come up with something new at one point once long ago, and then they’re thoroughly happy to just do that one thing until they die. And no desire to grow beyond that. They’re like, no, this is my thing. This is what I do. That’s that. And then there are some of us and I’ll call this the Miles Davis or David Bowie model have a desire to constantly push ourselves into new territory. I’m definitely that way, maybe to a fault. And I sense that you are too, that you also are not resting on your laurels. So I think you and I can recognize that kindred thing in us. Agreed. You think?

Jim

Totally agreed. And Miles and David Bowie I love AC/DC, fine, but Miles and Bowie resonate with me far, far to a much greater extent.

Derek Sivers

There is some people that I assumed because they’re so bright that of course they would keep developing and growing. And it’s been really weird and surprising, a little, let’s say, confounding to me that some people don’t, that no matter how, let’s say brightly they shone in their early days, some just stay at that level of brightness and don’t have the desire to go beyond that. Which is fine I guess for them. It’s just hard for me to understand that some people would be content to go from 0 to 100, and then just stay at 100 and not push for a thousand. Or anyway, it’s a silly metaphor. Okay, so your next question or your first question is, was I always like this? I think not, I think somewhere along the way, in my 20s, I started questioning the things people do and ask, why are they doing it that way. Does it have to be that way? What’s the real goal here? Is there a better way to get to that goal? Kind of disregarding norms and breaking things down to their lower principles and finding my own way to get to that goal. So in that case, the funny email. Yeah. At first, just when I was building the store cdbaby.com, I quickly put together an email of just like, okay, your CD has been shipped, thank you. And that was that. And then just only about a week or two later, I thought, “Okay, hold on, that’s really boring. Is that all I really want to do is just provide people with another boring confirmation.” I was like, “Really? The reason I’m doing this is to make people happy. Isn’t there another way to make people happy? I think I should give them something a little lively in their inbox.”

Derek Sivers

And so that led to that. But it’s not the correct solution for everything. It doesn’t mean that everybody should now go write an email like that. It means questioning what you’re really about, questioning what your real purpose is. So I do this with so many things. I mean, I’m a computer programmer too. So many times there is the default way that people do things. They’re the current norms. And when I’m learning a new technology, I look at that and then I think, “Well, wait, the whole point is to launch a server.” And I know that Facebook does it this way, or Google does it that way, but that’s a lot of levels of bureaucracy in between. The real point, which is just to get a server going, I think I’m going to skip all of these other layers and just go right to the point. No matter what other people are doing, I don’t care if it’s not the norm, it gets the job done. It all depends what you’re after. I think it’s very good for us to question our goals, whether they are pleasure goals, business goals, even personal relationship goals to look at what you’re really after. If you really want to be closer with somebody, maybe you don’t need to go to Fiji to get closer to somebody. Maybe you can just turn off your phone and have a good conversation on the couch.

Jim

Totally agree. And I get asked a lot. And so I’m going to ask you because you’re probably going to have a better answer when you had that satori in your 20s, was there something that you remember that happened that served as a catalyst for you having this? “No, wait a minute. Maybe I should be doing it this way.”

Derek Sivers

Yes. It started with my music teacher, Kimo Williams. Anyone listening to this, I highly recommend you go to the story. I wrote about it already, which is I posted it at sive.rs/kimo spelled k-i-m-o. Kimo was a music teacher I met randomly when I was 17. Just before I was about to go off to college, I was going to Berklee College of Music, and just a month before I met a guy in Chicago who said, “Oh, you’re going to Berklee, huh?” He said, “I used to teach at Berklee. You know what? I think I can help you graduate in two years instead of four. And I think I can do it in the next few weeks. Come by my studio at 9 a.m. tomorrow.” So I showed up at 9 a.m., eager to go, and and he said he was surprised. Apparently he often tells people, show up to my studio at 9 a.m. and nobody ever does, but I did. So he said, “Well, all right, you’re here.” So he gave me this crash course in music harmony, jazz harmony and arranging, and he basically just crammed this information into my brain and sat there with me on the piano bench next to me, and was going at this pace instead of the typical university pace, where he said, “Basically, universities have to adjust their courses to adapt to the slowest learner in every class.” He said, “But if you’re fast, we can do this much more efficiently.” So sure enough, I went to Berklee College of Music a month later and I tested out of, say six semesters of classes, and I did graduate college in two and a half years instead of four thanks to Kimo Williams. I think that started me on the path of questioning norms and asking myself, what’s the real point here? And is there a more efficient or direct way to do this?

Jim

That’s fascinating. And the reason I asked is because according to my parents, who are both in the great beyond now, I was that way from when I was a little kid. My mother used to tell me that I would always find the easiest way to do anything. And I said, “Well, what do you mean?” And she said, “Well, just yesterday, do you remember how I asked you to get something out of that bottom cupboard?” I went, “Yeah.” And she goes, “The handle’s been missing from that cupboard and the handles up at our waist level. And she goes, “Forever. When I want something out of that cupboard, I bend down and pull the cupboard open with my finger on my hand.” And she goes, “When I asked you to do it, you were like, yeah, sure, mom. You walked over, opened it with your toe and grabbed the thing.” And she said, “You just kind of do that naturally.” And I kind of thought about that. And I’m like, maybe my superpower is being just incredibly lazy. But then the more I thought about it, the more I think that some of us have a bit of a rebellious streak.

Jim

I guess I don’t believe in isms. I love Robert Anton Wilson, I don’t have any beliefs, but I have many suspicions. We’re going to talk about your own beliefs later because I completely agree with you. One thing that I do kind of am animated by is a natural suspicion maybe of that’s the way we’ve always done it. And it’s your example of the AC/DC. We figured it out. It’s this one way. Now we’re just going to keep doing it. And I just find if you want to be just dreadfully bored for the rest of your life, that’s what you’ll do. If you want to be continuously delighted, you’ve got to try different things. You’ve got to be willing to fall on your face. You’ve got to be willing to just make tons of mistakes. And that’s kind of my next thing that I wanted to ask you about, because I completely agree with this. And that is I love making--.

Derek Sivers

Wait wait wait.

Jim

Yeah, go.

Derek Sivers

Let’s not change the subject yet. You brought up so many interesting things already.

Jim

Okay. Brilliant.

Derek Sivers

You just made me realize instead of AC/DC, and Miles Davis, I wonder about, like, Michelangelo versus Picasso. You said Michelangelo kind of perfected a style of painting early on, and then just did that for the rest of his career. Picasso got to a style of painting in his teens, 20s, and then in his 30s he decided to try to push beyond that. Like, wait a second, there’s got to be another way. Michelangelo versus Picasso. Lazy. It’s so interesting that language has connotations that can be different per language, so it would be interesting to find the definition of the word lazy in many different languages, because in French I was surprised to find out that the word to expect something. I’m expecting it to rain today in French is the same word as to wait. It’s attendre. I think expect and wait are the same word. And I was so confused when I heard that, and it was because I was there speaking with a French person. I said, “No, no, no, those are completely different concepts. Expect means I’m like, I’m predicting it will happen and wait is just, I’m just sitting here.”

Derek Sivers

And he said, “No, no, no, these are the same. When you expect something to happen, you are waiting for it to happen. And when you’re waiting, you’re expecting something because you’re waiting.” No, those are so different. He said “No, they are the same.” So I wonder lazy in English we have a very negative connotation for that, you lazy bum, sloth. One of the sins, but I’ve heard it used for both programmers and musicians saying in a positive way I’m very lazy, so a programmer is saying, “I’m very lazy. I don’t write any lines of code that don’t need to be there because I’m lazy and I don’t want to type anything that doesn’t have to exist.” And I remember musicians saying-- actually I’m thinking of a particular guitarists saying, “I’m very lazy. The less movement I do with my fingers, the better. I don’t sweep my hand around with the pick, I just only go to the string to the minimum necessary.” And that’s why some guitarists were so much faster or seemingly more agile than others is because they were lazy. Using this word, it’s almost like we need a better word for it. Or Viva la Revolution will rebrand lazy as a positive thing.

Jim

You’ve got my vote.

Derek Sivers

It’s interesting that your mother noticed that. I really like that you said lazy as a superpower. I really think that we should reconsider this word and think of it as positive. Same as the word selfish. I think the word selfish can be a very positive thing that’s showing some self-worth or self valuing. Same thing with smug. Smug is another one we think of negative. But to me, I feel smug when I feel like I’m living in alignment with my values. I feel really good about myself. Like I woke up and I lifted weights first thing in the morning instead of waiting to do it begrudgingly in the afternoon. I ate really healthy. Today, I feel really smug, but that’s a good thing. It means I’m living anyway. I think those are the three I’ve identified. Lazy, selfish, and smug I think are all positive.

Jim

I couldn’t agree more. That reminds me of Bertrand Russell’s The Use of Language. I persevere, he is pigheaded using the various different definitions. And then I also think of the I can’t remember whose line it is. I think it was Wittgenstein. Maybe not, but the limits of my language are the limits of my world.

Derek Sivers

Yeah, I think that was him.

Jim

Yeah. And so I’m fascinated by language, just like you are, because, for example, I’m a huge fan of the Dao De Jing, which is Lao Tzu. Another one of my loves is one of yours, stoicism. I kind of mashed those two together, and I think they make a pretty good user guide, so to speak. So I started reading the Dao De Jing when I was 18 years old, and I started to finally understand it when I was in my mid 50s. And the way it normally gets translated, the Dao is the way okay or the path. And I was reading a new translation and I was delighted because this translator chose to use the term the process. I loved that because I always want to live my life like a verb, not like a noun. The process to me seemed more like, okay, this is something that’s moving. The path can just be a path, a single path, the way that means there aren’t other ways, but process means movement means exploration means all of these things that are much more active. I love the idea around starting a new language movement. Another thing that I think you and I really share, and you, as usual put it better than I do, “Ideas are worthless unless you execute against them.” What I often say is an idea without action is a daydream. And sure, enjoy your daydreams, sit on your couch, have your ideas. If they’re not put out into the world. In my way of looking at life, it’s a pleasant dream, but nothing really happened. And you say something. They’re just multipliers, which I really like. I like that idea and I’m going to be stealing that from you going forward. And execution is worth millions. Talk about that. I love the way you talk about that.

Derek Sivers

First I should say it was a reaction against somebody that came to me introduced by a mutual friend, saying, “I really want you to meet this guy. I really think that you two need to meet. He’s got something he wants to show you.” Okay, okay. So now I’m a little socially obliged. So I meet the guy. He said, “Okay, Derek, I’ve got this idea, but I can’t tell you the idea until you sign this non-disclosure agreement.” And went, “Oh.” And again, it’s like, ordinarily I would have said no, but it was like a good friend that introduced us. So I had this kind of social obligation, like, “All right. Go ahead. Tell me your idea.” This is before I had this idea times a multiplier thing. He said, “Okay, here’s my idea. Online dating with music.” And I said, “Uh huh.” And he goes, “Yeah, dude, online dating with music.” And I said, “Yeah. Go ahead.” He goes, “That’s it. That’s the idea. So I figure that you’re a programmer. You can make this thing happen. I’m the idea guy. I give you the idea, you go make it happen, 50/50.” And I said, “Wait, is there any more to this idea?” And he goes, “No, dude, online dating with music.” I mean, okay, all right. Hold on a second. I said, “Look, those four words, that alone is not worth 50%. Anybody can say online dating with music. Remember the movie There’s Something About Mary, six minute abs, five minute abs, whatever anybody can say that. So the hard part is going to make it happen.”

Derek Sivers

And I said, “You can actually have a bad idea and make a great company from it, or you can have a great idea and just sit there and hold meetings saying online dating with music and it’s not worth a damn thing. I guess I’ll pay for this. Our Diet Cokes.” I thought later that night about how annoyed I was and I wrote up an article that’s at sive.rs/multiply, or I kind of put it into a grid. I said, let’s say a terrible idea is a negative one, an okay, ideas are one, a good idea is a ten, a great idea is 100, and an amazing idea is a thousand. I said, but terrible execution, let’s say, is a -$1 and no execution is zero and good execution is a ten. Or maybe bad execution is a ten. Anyway, I list these numbers and I say to make a business, you need to multiply those two so you can have an idea with great execution and do well, or a great idea with no execution. And it’s worth nothing. So that’s the idea. It’s one of those things I thought of in a few minutes and wrote it up in 20 minutes, and I’m glad that it’s traveled very far.

Jim

It’s so funny because it seems so simple. I’m a journal keeper, and I’m in the process of getting them all machine readable so that I can have some Jim AI explain myself to me. And so I was going through one of my old journals for people who are not watching but listening. I’m holding up one of my old journals here, and I found this thing that I wrote when I was a kid in my 20s and it was e energy mind X energy action X energy random squared, because lots of random shit happens in the world equals result. And if you just look at it as a formula, if you’ve got the best idea, let’s give it a rank of a million. It’s the best idea in the entire world that’s anyone has ever come up with. And your energy of action equals zero zero. That’s what you get. And it just seems to me to be such a truism. And yet we get people asking you to sign an NDA for online dating with music. I used to joke that the only reason you should either require an NDA if you’re the one asking for one or sign one, is to make absolutely certain that people tell everyone about what they’ve signed the NDA about.

Derek Sivers

Nice.

Jim

So how do you think you would help somebody get from this idea that they want you to sign an NDA for online dating with music to moving toward, like if you were a coach and a young person came up and they’re like, “Derek, you are amazing. I read all your books. This is fantastic. What you’ve done, what you’ve achieved. My God, the variety of stuff in your life. How do I move from this abstract thought that I’m having to action, iteration doing it?” I mean, can you teach that to a person?

Derek Sivers

That’s a lot of what life coaches do, or personal coaches or business coaches or whatever. A coaches job is to take your blah, blah, blah and turn it into observable action. What do you want to call it? Deliverables or whatever milestones. The first thing is, if somebody declares some intention to say, okay, well, what actions would you take to make that happen? So in the case of a business idea, right, like online dating with music, I’d say, okay, take action on this right away. So action. You could think that would mean registering the domain name, but I’d say no, no, no, don’t do that yet. Do something that’s actually useful for this idea. Say talk to a real person. It helps to do it with real people. So you don’t stay in the land of abstract for too long, no matter how big your idea. You can get it going with one person right now. Online dating with music, you can pick one person that you know is single and another person that you know is single and ask them what kind of music they like and write it down and then say, would you also like somebody if you knew was also into Miles Davis or whatever, John Coltrane, and you can just test the idea with a piece of paper. No technology, no programming, no domain name, no incorporating an LLC. Just begin by talking to real people and get the idea going that way. And I believe that if you just start doing that kind of action immediately and you do that for 90 days, for example, you will be so much farther ahead in 90 days than somebody else who took action and just started programming a database table, or setting up an LLC and calling lawyers and opening bank accounts and what not. If you begin by talking to real people and test things in the real world with real people, you’ll get so much farther than anything else.

Jim

Could not agree more. When we were designing something at my old firm that we sold, gave investment advisors the ability to create custom portfolios for their clients and we thought, “Oh, this is cool.” I tried it way long ago, and a company called Net Folio in 2000 tech didn’t work in .com boom. But anyway, we kept working on it, working on it, working on it. And then we kind of came up with this list and several of my colleagues were like, “Okay, so we’re going to prioritize all these and then we’re going to start building against them.” And I’m like, “No, no, no, no, no, we’re not.” And my son had talked to me about talking to people. And the best advice that he got was, don’t do anything until you get 12 advisors actually in a room and ask them, do you want this or that? Do you like this or that? A/B test A/B test. And you could see some of my colleagues like, “Well, that’s crazy. That’s a waste of time.” And of course that’s the way we did it. And Derek, everything we would have thought would have been at the top of their wish list. Guess where it was? If it was even on the list, it was at the bottom of the list. And so this idea of asking real people what a wild concept. And yet we have this idea that we should do it the other way, and so much of business gets done the other way, and it just seems to me to be completely backwards.

Jim

It’s like the same sort of story when we were setting up O’Shaughnessy Asset Management, president of my company, said, “We got to decide on the trading systems.” And I looked at him and I went, “Chris, we don’t decide on trading systems, we don’t trade. We’ll make a horrible decision. What we’re going to do is push it down to the people who actually do the trading, and we’re going to use the systems that they want to use.” And it seems to me that C.P Snow’s The Two Cultures, art and science. Have you read that book?

Derek Sivers

No.

Jim

Yeah. It’s good you’d like it, I think, because what he talks about is this kind of split that happened. You could even say the left hemisphere and right hemisphere of the brain. They used to be conjoined. And then we had this split where the analytical was over here and the imagination was over here, and they stopped doing what you just recommended. We just got pitched on somebody who’s starting a company that’s trying to remerge the people who do the design and manufacturing. I didn’t know this. They’re split. So over here, there are the designers and they use computers to design everything, but then it has to go into a work order which shows the people who’s actually building it, how they want it done. Well, you can guess what will happen here. They don’t speak the same language, so they get it here and they’re all like, “No, no, no, no, no, that doesn’t work. We actually build these things and you’re missing steps A, B, C, D and E.”

Derek Sivers

So to apply that to your previous point, it’s important to ask the right people. If you’ve got a new business idea, you don’t necessarily go to the banker and say, “What do you think of this online dating with music?” You talk to single people that are looking to not be single. Or every now and then somebody pitches me on a new music startup saying, “Hey, here’s a thing musicians could use. What do you think?” And I always have the same answer, which is it doesn’t matter what I think. I’m not a musician looking to promote my music anymore. You need to talk to real musicians looking to promote their music because I have no idea their needs. And they think, “Yeah, but I want to get the VIP opinion.” But the VIP opinion should trail what the real customers and users feel. Yeah, I think you need to talk to the right people, like you say with the builder versus the designer.

Jim

I love that because that’s the other thing. This default to authority. And by the way, I’m not saying that we shouldn’t have experts. We should. I don’t want somebody off the street to come do brain surgery on me. I definitely want the person who knows how to do that. But the default to the VIP. The default to-- well, it’s the bandwagon effect, really. It’s kind of like, “Whoa, whoa, he’s got a good idea. Let’s jump on there and let’s ask him.” And maybe we’re asking the wrong person entirely. And I love that observation because if you want to find pain points, find them with the people who are going to potentially use the product. Single people in the case of the online dating, engineers in the case of the people building things, it just seems to me that’s such a straightforward and simple concept. One of the things that you write and talk about is the idea to get going, start iterating, just do that and just keep doing. Keep the iteration going. And I wonder, do you think it’s possible to like build a team that’s working together closely, not separate it like I just said about the engineer and the designers over here. But do you think it could work if there were like the idea people and they were cheek by jowl with the execution people? Or do you think it has to reside in one person?

Derek Sivers

There is a benefit to being a purely idea person, because I think the executor of the idea can trail a bit that I think that an idea person could say, “I know you usually do it this way, but what about that?” And even if the executor would say, “What? No, that’s crazy. That’s stupid. No.” But after sleeping on it, they might go, “Oh, actually, wait, I think you might be on to something. Nobody else does it this way, but that could work.” So in a way I think it can be useful to be a bit naive.

Jim

I agree, I think that cognitive diversity is something that people don’t pay close enough attention to because people think differently. They have different strengths, they have different weaknesses. Somebody who’s a great at ideas is necessarily probably going to think very differently than somebody who’s really great at execution. If you’re looking at companies everyone talks about, like Peter Thiel, you want 0 to 1. That’s where all the value resides. Yes and no. 1 to 100 can build a lot of value as well if that’s your goal. And so one of the things that I think is important is cognitive diversity. And if you have that you necessarily get access to like another brain that doesn’t think the way you think, and that can lead to really great combinatorial ideas and execution, because I also believe that the execution person can learn from the idea person, in other words, about how to better execute. And so the idea person, conversely, is going to say, “Well, that’s an interesting idea, but let me tell you why that’s going to be really hard for us to execute.” And then the idea person like, “Oh, okay.” You know what? I loved your story about how John Lennon met Yoko Ono. My nephew works for her and I’ve met her many times. She’s an amazing woman. And the story, for those that don’t know it, I didn’t know this story and I learned it from researching you. John Lennon went to an art gallery and saw this ladder, and being John Lennon, he climbed the ladder and he found a magnifying glass and it said yes. And then you told the story about running or catching up with an old girlfriend. And you said that you were still single, even though she was happily married. And her response was so delightful, which was just keep climbing the ladder. So you can learn things from a variety of perspectives which kind of leads me into your idea about beliefs. The book you wrote about beliefs.

Derek Sivers

I’m still writing it right now. That’s the one I’m currently working on.

Jim

But one of the things that you said that I read was that sometimes you believe something, even though it’s not true. That really resonates with me because don’t get crazy about looking, searching for the ultimate meaning. Look for use. Is this useful to me or not? George Box famously said, “All models are wrong. Some are useful.” Wow. Ptolemy was entirely wrong about astronomy, almost entirely, and yet incredibly useful for the early seafarers who were using his astronomical system to navigate the oceans. I think that one of the things that I took from you when I was reading about it, and I’d like you to expand upon, is why is that a controversial idea at all?

Derek Sivers

For one, I think when people say, “I believe....” whatever follows that they believe, it’s just a fact. But I believe that any time you say I believe, whatever follows that is not necessarily true. That’s why you have to say, I believe.

Jim

Believe.

Derek Sivers

You don’t say, “I believe this apple is on the counter right now.” When you’re standing there looking at it.

Jim

Right.

Derek Sivers

You just say the apple is on the counter. You don’t say, “I believe that I’m 53 years old.” You say, “No, I’m 53 years old.” I believe tends to mean that you are taking your stance on something that’s debatable. And I like to reframe anything debatable as not necessarily true, because if it’s not necessarily true, and by that I mean inarguably, absolutely, observably, objectively, repeatedly and according to any perspective, including an ant or an alien. Only in all of those conditions will I consider something to be absolutely true, which means that almost nothing is absolutely true, especially not all the social stuff we say every day. This person is a bad president or the world is flat. Sorry, that’s like a physical reality and it may not do that one. I accidentally got mixed in with, you know, the people that spout opinions as if facts. This country is going to hell. This government is doing a bad job et cetera. They’re all spoken as facts. The person saying it usually thinks it’s a fact. But if you can poke any hole in it or say that any perspective in the universe could be otherwise. Well, then it’s not an absolutely, necessarily, observably, objectively, repeatedly true fact. So once you define something as not true, well, then you’re for creative agency can kick in. Your ability to negotiate life and challenge situations and choose a perspective that empowers you. Because ultimately, most of what we care about is our ability to do something. Or at least feel happier, tranquil about something. It’s mostly about actions, but sometimes, say if something’s in the past, maybe what you need to do is just come to peace with it. So if something has already happened, you can choose a perspective or a “belief” that says, “That was wrong. That person wronged me, what they did was bad, and I am mad.”

Derek Sivers

And that perspective is one that you could choose, but it’s going to make you upset, and you could choose another perspective that says, “That person was doing the best they could with what they had. They thought they were doing the right thing.” And where it gets interesting is even that is not necessarily true. That person might have actually done something intentionally ill willed, but you choosing to believe that they were doing the best they could and they meant well will make you feel better, since it’s something in the past that you can’t do anything about anyway. But more importantly, are the things that we can do something about. Where your choice to believe one thing versus another can mean the difference between you feeling helpless and resigned and plopping down in bed, just feeling angry and stewing, typing nasty comments into social media versus feeling empowered, feeling powerful and doing something about it. And all of this just goes on in your head. All of this is just the perspective that you’re choosing to take. And I think if we let go of this idea of true saying, it’s just true that this government is bad, it’s just true that I would be happier if I lived across the world somewhere. If you let go of all of that and say, no, no, no, none of that is true. The only thing that’s true is there my hands are clapping right now. That’s true. Physical observable things are true. Everything else is just a perspective that you can choose to take then the way to judge it, if we let go of the word true. Is whether this is useful to me or not.

Jim

Perfectly said. I wrote a piece or did a series of threads on Twitter called “The Thinker and The Prover” and I was borrowing from Robert Orr, who had borrowed from Robert Anton Wilson derivative all the way down. But I found it very useful because what it says is basically the thinker can think anything it wants, like the Queen in Alice in Wonderland. It can believe three impossible or six impossible things before breakfast. But the minute the thinker stops thinking, the prover takes over. And the prover makes that belief true for you and what it does if you want to talk about it scientifically, they call it the reticular activating system. And for example, if you want to do an experiment, this is actually fun. Think of something you don’t see very often. In the case when I was doing this experiment on myself, I thought to myself, I don’t see green cars very often, you know, I just don’t see green cars. And so I wrote down, I’m going to look for green cars. And then I wrote down, I think over the next two days that I will see five green cars. You know how many I saw? 49.

Derek Sivers

No way.

Jim

Well, and the reason was because I turned on my reticular activating system and my prover said, “Okay, we’re going to find green cars today. That’s our job today”.

Derek Sivers

Nice example.

Jim

The example of true that and we’re back to language and what words can mean to people. True to people means fact means indisputable means only correct answer. That’s true. And generally speaking, very little that we say or do or believe is true. Then if you can understand that and that you can understand that, it’s my opinion that doesn’t make it true, then you’re open to looking for useful beliefs that can get you where you want to go. So my next question for you is what beliefs of yours now are you leaning on to make your life a more pleasant or directionally superior experience to before you embrace those beliefs?

Derek Sivers

They’re tough to identify because you often don’t even realize that you’re choosing them. Off the top of my head, this is going to sound weird, but I was on my computer programming up until just a minute before we started this phone call. So I’m sorry. That’s just what’s on my mind right now.

Jim

That’s fine.

Derek Sivers

But I take an approach to computer programming that always looks for the absolute minimum lines of code necessary, the minimum number of dependencies necessary. So I don’t want to include 19 JavaScript libraries to do something that I could do with a shell script, even if including 19 JavaScript libraries could mean I only need to type ten lines of code, and a shell script means I have to type 50 lines of code. Well, technically, typing 50 lines of code is the simpler solution because it has less dependencies. Simple and complex are misunderstood words. The word complex is an adjective describing the verb complect, which means to braid things together. When things are braided together with other things, they are complected and therefore they are complex. Simple is a version of simplex, which means unbraided not connected to other things, and we mistake those for hard and easy because it can be very hard to make something simple that has less dependencies, that’s not complected with other things, and it can be very, very easy to make something complex, especially with computers. You can just type install WordPress and it will install millions of lines of complicated code. Or you can write your own blog from scratch with no dependencies. And it will be harder, but objectively it’s simpler. A current belief in my programming is that I believe for me, it’s more important to be simple, even if that’s harder. See what I mean? That was a trivial one, but sorry, that’s the one on my mind right now.

Jim

No, it’s not trivial. It makes the point nicely. And I love the differentiation between simple and complex. I think that’s another bug in our human OS. I think that we are designed to think the complex is going to be the more correct answer. In fact, I wrote an entire piece about this, about a thing. It takes too long to tell the entire story, but the punch line is one person was using a very simple way to determine if something was a yes or a no, and he was getting the correct feedback on his guesses. So he was soon getting like all of them, right with his very simple approach. This person over here was given incorrect feedback. His feedback was based on this guy’s guesses. And so his methodology, when described necessarily was very complex. He had to weave this great tapestry of sometimes it’s this and sometimes it’s that. And the thing that was amazing from this study was that the guy was getting them all right with the simple solutions, was in awe of this other guy, and felt that his own pedestrian explanations were horrible and so we’re kind of trained to think that the complex is smarter or more complete. And yet I find the exact opposite.

Jim

I find that a real superpower is the ability to take something that might be complex and make it simple in terms of use, in terms of understanding, in terms of all of those things. And I think it was Charles Mingus, the musician. His son was an artist, and he showed him some of his work, and it was the abstract. And Mingus looked at it and he went, “Go and learn how to draw an apple.” And his son was like, “What do you mean? This is my art.” And he goes, “No, no, no, no, learn how to do a drawing of an apple that looks like a fucking apple. And then you can play Picasso and you can do the bowl that Steve Jobs embraced.” First you show the Picasso bull that is just a bull. And then you just are the lines at the end of Picasso’s. That was his journey. And so I think that’s a very empowering belief, because it doesn’t apply just to programming. It applies to a lot of things it can apply to if you’re writing something out, if you’re writing a story, if you’re doing any of those kinds of things.

Derek Sivers

Okay, Jim, I just realized so your listeners might have a bit of a financial bent because of your past. I was actually just asking myself this yesterday, when it comes to the infrastructure of my personal finance, that I could value simplicity and say, I could just have everything in one bank account. And then I started think about the trade off between simplicity and safety, going, ooh, in a way, what I’m defining as simple could make me more fragile. Because if something happened to that one bank, or if somebody hacked that one account everything’s gone. So should I separate things into two accounts? Well, if I’m doing that, maybe separate things into four accounts. But oh, my God, I’ve just made something very complex. But maybe is that safer? I don’t know, where do you fall on that when it comes to financial things?

Jim

There’s a great quote that there are two schools of investing thought. The first school is don’t keep all your eggs in one basket. In other words, diversify. Make sure that you have a well-diversified portfolio or in your case, you have multiple banks. So if one fails, you have all the other ones as backups. And then the other school of thought is no, no, no, keep all of your eggs in one basket, but watch that basket very closely. And so they’re equally applicable depending on the person. That is ultimately what it comes down to. What type of person are you trying to help? I put my investment advisory hat on here and I haven’t had on for a while. So what I would do is ask a series of questions to determine who am I dealing with here. Am I dealing with somebody who just really values that simplicity and therefore is going to get this much more simple plan, but then we’re going to have to watch it really, really closely and have to explain to them that, okay, this is simple but not necessarily easy. Or are we going to say they’re the type of person who we’re going to give a widely diversified portfolio of different asset classes and everything, and typically one rising the other fall. That’s the correlation between things.

Jim

But, you know, when you have a financial crisis, guess what happens. All correlations go to one and everything, it’s baby bathwater time. So we all have unique irises. We all have unique fingerprints. And yet that doesn’t stop us from saying, okay, so here are some general guidelines that are good. Then you got to match it to the person. Then you’ve got to say, because ultimately, Derek, what I’ve found in investing is the point of failure is the human. Remember the Pogo cartoon? We’ve met the enemy and it’s us.

Derek Sivers

Yes

Jim

That is so true. It is just so true. And generally speaking, we are the point of failure. And generally speaking, it is usually an emotional, volatile time where we make a bad choice. That’s human OS. That’s the way we’re designed. And so to try to help people, it can’t all be intellectual. My friend Jason Zweig, who writes for the Wall Street Journal, he has a great metaphor for this. He goes, “The difference between intellectually understanding that your portfolio could go down 50% and then actually experiencing it in real life is the same as showing a person a picture of a snake and then throwing a snake in their lap.”

Derek Sivers

Nice. Good one, I like that. It’s so interesting, by the way, to get meta for a second, I hope that your listeners find this useful. A thing that I try to remember to do, and I sometimes forget to do, is when you ask me a question about me, if I’m being a good interviewee, I should actually answer it on behalf of the listener in a way like something that the listener would find useful. So in a way, I think I kind of failed myself when I talked about this very specific programming thing that probably almost nobody listening can relate to. And so I hope that we rescued it a bit with that financial one. I love that you brought up that one thing, but watch that one thing very carefully. I had heard that quote, but like ten years ago and I’d forgotten it. So thank you for that. This idea of simplicity even applied to relationships. Again, we may think that simplicity is a good thing. But if you’re following that to its logical conclusion with relationships, that would mean that you only have one relationship, or maybe none would be the ultimate conclusion. And we don’t want that. So in some ways in life, we want the complexity of many friends, many connections, the warm cocoon embrace of having so many friends and loved ones around. But let’s admit it, that’s very complex. That’s almost the most complex thing in the world, your relationships with other people. But yet we like that complexity. It’s really interesting to think of simple versus complex as detaching them from ideas of easy and hard and good and bad. They’re not correlated.

Jim

That’s a great example. There is not a one size fits all for anything. We’re both into stoicism for example. Stoicism is really useful because, at least for me, the core understanding that I take away from stoicism is it is not the event, it is my reaction to the event that determines my state of mind. I also kind of extrapolate it to your either outer oriented or inner oriented, and I find I’m inner oriented. In other words, even though I get a 98 on the big five on extroversion, I’ve trained myself to understand that no no no no no, it’s not that person’s fault. It’s mine. If I react really badly, let’s say you told me, “Hey, Jim, I hate your podcast. I listened to it once. It’s awful. You’re dumb. You’re stupid. I don’t want to talk to you.” I could say, “That Derek is an awful, horrible person.” Or I could say, “Huh? Guess he just doesn’t vibe with the way I do things. And that’s fine. He’s different than I am.” One reaction is going to have me wallowing, right. And oh my God, I really love Derek and I read all of his stuff and he hates me. And now I’m a failure. Or like, yeah, he’s just not into me. Who’s controlling that reaction? Me. And if you get that, that’s the only way, in my opinion, where you can act with high agency. And I know you’ve written quite a bit about agency. I read all these people, “Free will is a myth. Here’s why.” And don’t spend a minute of time thinking about that. Why do I not do that? Well, first off, at least now.

Jim

Now we’re getting back to true and false. You can’t design an experiment that proves the sun is up, that there is no free will, or that there is free will. It’s like the Middle Ages, where the theologians would argue, how many angels can dance on the head of a pin. That’s a waste of time. And so instead of thinking about free will versus no free will, I choose to believe that I have free will. Because guess what? My outcomes get a lot better when I have free will. And I choose to have agency. Because guess what? All of my outcomes are much better when I accept the agency. Now, a lot of people don’t want to accept agency because they want to blame somebody else. And you have a really interesting-- you’ve written about this somewhat extensively. Talk to me a bit about that. But answer, by the way, I think you were wrong about I should answer on behalf of the audience. No no no no no, they want to hear you. They want to hear this whole thing. The only reason I do this podcast is because I wanted it to be a series of interesting conversations with super interesting people. You’ve been in a restaurant or a bar when you sit next to the table and there’s a movie even My Dinner with Andre, which when I finally got convinced to do this podcast, I’m like, “Okay, but it’s got to be my Dinner with Andre. It’s got to be fly on the wall listening to these guys having a cool conversation.”

Derek Sivers

Okay. Good comparison. So agency. Yeah, you and I have that in common. When I sold my company, to the outside world, it looked like a success. But to me, it was a personal failure because I wanted to run that company forever. And after ten years, I had mismanaged it so bad. Wait. I’m sorry. Reverse that. After ten years, those jerks that worked for me were so evil. They were terrible. Those assholes tried to kick me out of my own company. I was just surrounded by idiots. So I had to sell now. Okay, so that’s truly how I felt for the first year or two after selling. After a year or two, I realized that is a mindset that makes me weaker. A mindset that makes me stronger is to admit that I mismanaged things. That they were just playing their inevitable role in a situation that I created, that I could have done things better. Or let’s just say I messed up and that’s why they acted the way they did. That to me, is a way more empowering mindset and in a way actually gives me more tranquility at the same time. Because if I think that they were jerks, then I can just stay mad forever.

Derek Sivers

If I think that they were just playing their inevitable part in the situation I created. I can forgive myself. I can say, “All right, I messed up.” I will feel the pain from that mistake and aim to not do that again. But let’s just say for anybody listening, that what I’ve just said is not necessarily the right and true way to think about things. This is a way that worked for me. There are some people who are raised with or by parents that filled them with guilt, and they have a terrible time feeling that everything is their fault, and those people might actually find it more useful to believe that some things are not their fault. That might be the more empowering mindset for them. So let’s just say any time we’re talking about mindsets, please always know that there is no right or wrong, no matter who’s saying this worked for me, or even if somebody says this is the right way to think about it, what they’re really saying is this works for me. So yes, believing everything is my fault that works for me.

Jim

And for me. And one of the things that I always kind of scout for is, directionally speaking, when I find intriguing people such as yourself, they do have some things in common, and one of the things that they have in common is a sense of high agency. I do appreciate your caveat, though, because I think you’re right for many things in life, for people who are actively trying to get better or be happier, I don’t care. Fill in the blank. What you have to do is you have to investigate as best you can the various ways you could do something, and then find the thing that resonates with you. Because honestly, you’re not going to do it if it doesn’t resonate with you. This expert said that I have to follow this diet and do this specific kind of exercise, and that’s what I’m going to do. And it’s something that you hate, and then you just never do it. And so you want to continually look until you find that click, that click in that is like, I can do this. This is something that I think I can stick with. Because honestly, persistence is another thing that I think one of the things that as I was preparing for chatting with you that I just love about you is you do look at things from so many different angles, which is something that I really, really admire. Robert Anton Wilson is somebody I love. I’ve read all of his stuff.

Jim

He was 50 years ahead of his time, and he took up the term that I think Tim Leary came up with, which was Reality Tunnels. And he makes the point in his work that we all have different reality tunnels. We don’t have the same exact nervous systems, and we don’t have exactly the same minds. And he proves it in a variety of ways, like having 30 people in a class he taught, sketched the hallway on your way to the classroom, and guess what? All 30 sketches are different. And then when you really understand this and you try to put yourself into a different person’s reality tunnel, your aperture opens up so much more widely because you’re like, “Oh, well, of course.” If I actually believed this, it’s easiest to do in either religion or politics and put yourself in the reality tunnel of somebody who is the espousing things that you disagree with, and by doing it, you can immediately understand a little bit better, not only yourself, but that other person as well. And when you put it in those kinds of terms, your advice resonates because you’re right. Well, you and I are very high agency believers, and acting with that, you were probably smart to say, by the way, if you were raised to be guilty, guilty, guilty. Member. Game of Thrones. Shame, shame, shame with the bell. That’s not going to work for you. But what do you think? Are these things teachable?

Derek Sivers

Teachable? Yeah, I mean, you and I learned them. We’re sitting here talking about them. Yes. To somebody who’s interested. Again. Let’s go all the way back to AC/DC, aka Michelangelo. Who says, “I’m good at what I do. I’m not looking to be different than what I am. I’m happy with who I am. I’m not looking to change my perspective.” Versus Picasso, Miles Davis, who says, “Okay, I did that. Now what’s next?” Maybe it’s a type of personality that’s open to wanting new perspectives. I’m personally obsessed with it, and I didn’t even realize how much I’m obsessed with it until just a few days ago, when somebody was asking for my recommendation for a book on understanding another perspective, and I said, “Oh, sure, yeah, you should look at the Time Paradox, which helps you understand people who have different perspective on time.” I said, “Oh, but you should also consider the Prisoners of Geography, I think it was called, which helps you understand how geography can shape philosophy.” The people that grow up in mountainous places or cultures that developed in mountainous places, have a very different culture than cultures that developed on the plains, versus ones that were in the cold versus in the temperate equatorial zones.

Derek Sivers

And I said, “But you should also understand that someone with countries, I said, you must read Au Contraire, Figuring out the French.” I said, “It’s the best book on a single country’s culture and Watching the English is the second best book on that subject.” And then I named a few more, and I said, “And you should also read the--.” And suddenly I listed out, I think, something like eight more books on the subject. And I went back and I looked, I went, “Oh my God, I’ve read like almost 20 books on the subject of understanding other people’s perspective. Wow. No wonder I think this way.” I mean, how many time does it take to read a book? 5 to 10 hours or something like that? Oh my God, I’ve probably spent at least 200 hours just reading other people’s thoughts on understanding other people’s perspective on the world. And I’m like, wow, I think I’m really obsessed with this subject.

Jim

And that’s the challenge because I seek out people who are incredibly insatiably curious, because to me that’s a great marker for a lot of other things. People who are just I think of Dorothy Parker’s line, “Curiosity is the cure for boredom.”

Derek Sivers

Oh, nice.

Jim

There is no cure for curiosity. And then I add in Steven Wright the comedian’s “Curiosity killed the cat. But for a while, I was a suspect.”

Derek Sivers

Nice.

Jim

I do find that there are some markers, if you will, whereby an intensely, insatiably curious person is going to have other characteristics as well, usually. And it’s this idea of trying to come up with a way that this could be taught, because people come to me and they’re like, “How do you know all this stuff? Or why are you interested in that? And how can I do that?” And if you got any advice there, I would love to hear it.

Derek Sivers

I just had the idea that maybe this starts with realizing that you are not right, that all of the things you think of as true and right are just one way of looking at things. It might start with that. If we can help people understand that they are not right.

Jim

I love that because the only way, if you look at Claude Shannon and information theory, information is that which surprises you. So in a poem, a poem can be densely information rich, a political speech, zero information because you’re not surprised. When do we learn? When we’re wrong. That’s when we learn. And one of my founders in one of our portfolio companies says, “I always try to make novel mistakes.”

Derek Sivers

I might have to take it back. I think the thing I just said about realizing that you’re not right has to come after another step, which is people valuing the very idea of learning and growing. Because let’s go back to again to Michelangelo, AC/DC. You might believe that, “Nope. I do not want to learn any new things. I see no value in it. I am Michelangelo, I am the best there ever was and there ever will be. I have perfected my style. I have no desire to change.” A lot of people believe that on a, let’s call it a more pedestrian level, that “No, I’m good. This is me. This is who I am. This is where I live. This is how I like my eggs. This is it. I’m good.” And somebody comes along saying, “Hey, I’ve got a way that you could be different or better.” And they’re like, “Nope, I’m good.” I think it has to start with that before anything else. But you know what, I have a proposal. I would love to split this conversation into half. I have loved this subject so much. I got to tell you, if you don’t mind me praising you on air.

Jim

Flattery will get you everywhere.

Derek Sivers

Actually, I do a podcast like this every week. I’m a guest on someone’s podcast every week. I think this is the most times I’ve ever wanted to interrupt to write down something the host has said. You mentioned so many things that I’m going to beg you for a copy of this recording as soon as we’re done. But also, there are so many things. Let’s keep talking about this. Should we break this into two parts?

Jim

Done, let’s start at two and then maybe see if we iterate. It might even go beyond two.

Derek Sivers

Yes. All right audience, we will see you again. My name is Derek Sievers. Nice to meet you

Jim

And I’m Jim--

Derek Sivers

Go to my website.

Jim

Intermission right now because we’re coming back for part two soon.