I stopped going to the office, I started shutting off my phone until I realized that I was running from my problems instead of solving them, and I realized like this was kind of a do or die moment, like I need to fix this or I'm toast.

Hello and welcome. I'm Shane Parrish, and you're listening to the Knowledge Project, this podcast and our website, F-stop blog, help you sharpen your mind by mastering the best what other people have already figured out.

If you enjoy this podcast, we've created a premium version that brings you even more. You'll get ad free versions of the show like you won't hear this early access to episodes, transcripts and so much more. If you want to learn more now, head on over to F-stop Blogs podcast or check out the show notes for a link. Today I'm talking with Derek Sivers. Derek is my brother from another mother. Derek started off as a musician and circus clown, created CD Baby, which went on to become the largest online seller of independent music.

Derek is the philosopher king and so thoughtful about his approach to everything, as you're going to see when you listen to this conversation. In this episode, we're going to talk about the benefits to being naive, to the ways of the world, how to decide what to work on and who to spend your life with. Delegation, the value of execution over ideas, reading mental models and Charlie Munger making decisions, living a meaningful life and the biggest mistake he's ever made.

I hope you enjoy this conversation as much as I did. It's time to listen and learn.

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Oh, thank you.

And we've been trying to do this for like so long. And we've been like, I'll just wait till the next time I'm over and then we'll do it in person to be so much better. And then.

Yeah, and I've been a paid member of Farnam Street forever and I've just been reading your stuff forever. And it it's great to finally have this conversation.

I'm looking forward to it very much part of the research that I did for this. Like it's fascinating because I mean, I know of you. I read your stuff and then going a little deeper behind the scenes is is always fun.

And I found this really interesting story. You worked as a librarian at the Warner Chapel Music and you quit.

And that is like one of the most interesting stories I have ever seen with somebody quitting.

Can you can you share that with me? Sure.

It was my first real job.

It was at Warner Brothers in midtown Manhattan, the music publishing division.

It was an office with about 14 employees. And I was 22 years old and I had been working there for two years.

Just the bottom entry level position running the music library. But I loved the job and I loved my colleagues.

But after two years, I was ready to quit so I could be a full time musician, like I was earning enough on the side as a musician that I could quit. So I found someone to replace me.

It was an old friend that I knew would be perfect for the job. I knew that she would do it really well. She had the right temperament. She was in the right stage of her life. I knew that she'd be psyched about it and really give it her all like I did.

So I offered her the job and she said yes, and she moved to New York City to do it. She stayed at my place for a while. I trained her and I taught her everything. And after a week or two of that, that's when I told my boss that I have to quit now.

But here's my replacement. She already knows everything and she's starting on Monday.

That is just phenomenally mind blowing that somebody at that age, let alone any age, would sort of like think to do that. But I didn't know otherwise.

Right.

Like, well, this is this is sort of the interesting aspect to this for me, because you started CDB after that. I think most people are generally familiar with that story. But the first time somebody quit, you were like, OK, who's your replacement?

Yeah, I still I guess when I quit that job at Warner Brothers, my manager just kind of went, oh, OK.

And I just walked out, you know, and I could just, you know, I basically said I quit and I walked out because everything was all taken care of.

So, yes, 12 years later, I had my own company. I was running CD Baby, and the first time one of my employees came up to me and said, Hey, man, I'm going to have to quit.

I said, Oh, wow, OK, no problem. Who's your replacement?

And then he looked at me kind of confused. He said, Dude, I think that's your job.

And then I was confused. I was like, wait, but you're the one quitting. Why is that my job now?

It just yeah, we were both confused.

There's definitely some benefits to being naive, but the ways the world can you can you share some of those with me first principles thinking maybe, you know, it will.

I honestly didn't even know it was called that until reading your site. And in fact, I still don't know that much about it. But I was really excited to buy your new books last night to learn more about it.

So to me, the world feels unnecessarily ceremonial, like people imitate others without questioning it enough. But I don't want to learn their ways.

I don't want to be like them.

So instead I just ignore at all and ask myself, what's the real point? Meaning like, what am I really trying to do here?

What's the real point of all of this song and dance? So if it turns out that that traditional complexity was actually needed, well, then I'd rather find that out for myself and notice that this approach is more creative.

Right? It's more inventing instead of imitating, which then means it's more fun. Let's pick a concrete example of software. Say I want a website to share my thoughts. So I look at WordPress.

That's what everybody else does. Let's just look at WordPress. So I got a WordPress.

Doug and I download the zip file and I look inside and it's like, what the hell are 884 files in here?

There's six hundred two JavaScript files in here. Nineteen database tables. What the. No way I'm going to learn all of that, I'm just I just want to put five paragraphs of text on a Web page. OK, so what's another option? Everybody seems to like medium dotcom. Let me look at medium dotcom. Pull up an article and like, what the hell?

It was like 2.5 megs of downloads, like thirty three as a JavaScript and see a JavaScript in case files just to display an article in a way that's like a thousand times bigger than it needs to be.

And to me, like if I were to tell all of my readers, like go to medium dot com to read this five paragraphs of text I wrote that would be like those companies, you know, if you order something small, like you buy a like a USB stick and they mail it to you in a big box full of Styrofoam, it's like, no, no, no, that's don't that's junk you're giving me.

Your garbage is dumping my garbage on everyone. So I'll ask, what's the real point here? I just want to post an article on a Web page. I'll just open up a blank document. I'll to type out the article and I'll put paragraph tags around it. I'll put the title in an H1 header tag and I'll just put a couple little HTML headers and footers. So it's a valid document and then put it on a server and OK, so I need a home page to list the articles.

Right.

OK, so we'll add some Ulli list tag to the homepage, H.F. to the article and I'm done so now I have to HTML files. No, no nova javascript, no database. And the file size is like less than one percent of the typical medium dotcom or WordPress blog post. Right.

So in the case of WordPress, I talk about complexity. In the case of WordPress, I understand that their complexity came from making generic software that pleases everyone from Disney to CBS. Right.

Like there are companies with hundreds of employees needing to use WordPress all at the same time to manage their content. But I'm just me and I don't need that complexity, so I think that this is a nice metaphor for life. It doesn't have to be so complex. You can do just what's best for you, not need to adopt the legacy software that everyone else uses.

That's really interesting. So two themes stuck out to me there, the complexity theme, but also the imitation versus innovation. If you don't imitate I mean, one of the byproducts of that that I can see is that you're going slower, like you probably took you longer to do that than it would have to download WordPress. And that goes back maybe to the complexity right where they're intertwined in the sense of like maybe we don't have to do as much as we think we have to do.

Right. Rich Hicky is the inventor of the programming language called Closure s.L. O.J. Jewelry, and he has a brilliant talk that's up on YouTube. I think if you search like simple versus easy rich hicky, he makes this beautiful comparison about how anybody can go to their computer and type like he says, JEMB, install, hairball, like you can type one command and install WordPress on your server.

And he said, yes, that was easy, but you just installed a big steaming pile of garbage on your server.

That is a massively complex because he defines complex as having the word root in the word complex, which means to brade two things together. So he says complexity is when you've got many things braided together, said yes, it was easy and fast for you to type gem, install, hairball or install WordPress.

But look what you've just done. You've now just installed thousands of complex files when, yes, it would be a little harder for you to just make your own HTML page from scratch. But notice that by definition that's simpler. So simple is not always easy. I like that a lot.

I'm just trying to figure out, like in my head, where to go with that. Like, I'm always I think of Farnam Street, right?

Like we're always trying to reduce I'm trying to reduce the size that people download. I'm trying to take away the things that people don't need and just sort of like leave what's left.

But that is not not easy at all. Like, that's hard.

Yeah. You have to kind of nerd out on it. Like, I really nerd out on this stuff. In fact, this my little rant.

But I just gave you about WordPress, for example.

I said this to a friend of mine and when I was done, she said. Yeah, but so what like I said, something like, you know, you're going to have to the average user is going to download like 98 files just to read your four paragraphs of text.

It's so unnecessary.

And she goes, so like most people think of it that, you know, she goes, almost nobody but you is actually looking at the code for most people. They just click a link on their phone and they read the article.

They don't care that behind the scenes. Ninety eight files were downloading like, oh yeah, I forget. Like, I'm just I nerd out on this, but you do.

And that's what's important though, right? Like it's something you you care about innate to what.

I mean you care about other people's experience with your stuff, which is really rare these days with that level of thought is really like and I was thinking like yesterday as I was preparing for this, I was trying to order some wine for some friends of mine and it was online and I was trying to do this thing and it was just so difficult.

And I was like trying to support local businesses and I was trying to do something nice for my friends.

And it's like 90 minutes later. Right.

And I'm still trying to order this wine and it's like copy paste the order number into your E transfer that you send to like this address with this password. And it's like, holy cow.

Like I like, have you used the product that you are getting other people to use, you know, innovation versus imitation from most things?

I just find innovation more fun and we're humans. Fun matters. If I get more joy out of doing it this way and it takes me six hours, but it's fun versus. Yeah, I could just click this link and be done with it in ten seconds, but it's less fun. I'm sorry. Now I'm back to the making a website, not ordering wine. I find it fun to order wine for 90 minutes.

But yeah, if you find the process like some people make their own furniture, right.

You can visit somebody's house. It's like I made that table. I made that chair.

Of course they could have gone to IKEA to buy one, but they chose to make it because they wanted to. So yeah, I take that approach to a lot of things in life.

One of the other things I've noticed with imitating is that we often don't know what's next. Right. So you consider hiring somebody with a skill, but a skill that they've just sort of like copied from somebody else. Then when things change or they're they're different, they have no idea how to respond or how to deal with that.

Right. Well, isn't that your interest in the first principles, thinking it's like get to the root of what you know you, isn't it?

You have this Phénomène quote, opening volume one of your book, right? Yeah. I mean, we're the easiest people to fool.

That much is clear. But I mean, I also think that we try to not consciously, but we do try to to fool other people.

Like if you think maybe Warren Buffett is a good example. Right. There's the 2008 housing crisis hits and there's a whole bunch of people who who imitate Warren Buffett.

Right. They talk like him.

They go to McDonald's every morning. They eat their Egg McMuffin and they they say all the right things. And being able to distinguish between Warren Buffett and these people, if you couldn't see them, would be really hard.

But then a crisis hits and they're paralyzed like they don't act if they're not Buffett.

Right. And it's only through that crisis that it's revealed. So like this this whole thing in life is also like, how do you tell the difference between somebody who's imitating and somebody who's the real deal?

Like who's who actually understands?

That's a great question. I was hoping you have an answer.

No, let's just leave. That is a beautiful rhetorical question for the audience.

How do you how do you decide what to work on? I mean, you have a unique framework. You're known for this hell, yes or hell no sort of framework. Like how did you come about that? Expand on that for me.

Sure. Hell yeah. Or no. To be clear, this is just one tool in the toolbox, right, like I don't have that much to say about my monkey wrench. It's not meant to rule the world. It's just a monkey wrench.

But here's the problem.

We tend to say yes to whatever we can. We like to stay busy. So when faced with the decision to do something, we ask, can I do that?

And if yes, then we often say yes, maybe it's the fear of missing out.

Maybe it's optimism. Maybe it's because time is like distance where we can't see far away so clearly. So we mistakenly think that we'll have more free time in the future. But then today comes and now it's all close and vivid. Now you can see it clearly and you're too busy.

And so you curse your past self for saying yes to that thing that you have to do today. You know, three months ago, it was easy for you to say yes to this thing in the future when you have infinite time.

So here's the solution, is to raise the bar all the way to the top, say no to almost everything, and leave space in your life, leave free time. But this is not relaxing.

It's strategic, because then when something great comes along like something that makes you say, oh, hell, yeah, that would be awesome, then not only can you say yes to that, but now you have the time and energy to throw yourself into it completely.

Like now you can give it your all, you know, the baseball metaphor. You can knock it out of the park. And I think strategically it's better to do five big things with your life instead of five hundred half assed things.

You know, I think that applies to a lot of things. Right. And it's better to, you know, be thoughtful and and treat less than, you know, just throw ideas out there and.

Right. How did you come up with this? Was this like an overnight thing or.

Yeah, I told you about. So I have to say one thing. What you just said, like, it's better to tweet less and of more. I still just say that it's just different, like some people do get their best creative ideas by just spewing out as much as possible. And maybe they spew out a thousand times more than most people.

But if one percent of those ideas are better than it's the better result.

So I don't want to say like this is the best approach to take for all things.

That's why I say it's just one little monkey wrench. I think it's a tool to use when you're overwhelmed and almost drowning in opportunities and therefore you don't have the time to give your full attention to any of them.

As for how it came about, it was just a situation where I was telling my musician friend Amber Ruba about a decision I was trying to make about whether to go to this conference or not. And as I was explaining my thought process behind the decision, just thinking out loud, Amber rubato is actually the one that said. So basically, you're not trying to decide between yes and no. You're deciding between fuck. Yeah. And no.

I just laughed and I loved it and I so I blogged about it the next day I changed the word to hell to soften it a bit and the idea caught on and that's all.

And when you started implementing that, was it a gradual process or like what was that?

Oh, no.

It was like, is it soon? It's like sometimes it takes somebody else to say things that you might have already been feeling or thinking, but then somebody puts it into better words. That's what we love when poets do that. You know, we love when books do that. When you read a little wise book like, you know, an old one, like think and grow rich or something.

And you go, Yeah, yeah, there we go.

Like, I already felt this, but he just put it so well, that's the way I feel.

And so, yeah, my friend Amber Roberts, who's a songwriter, just kind of gave me that nicer, simpler mantra. If it's not a hell yes, then say no. And yeah, I just started using that for everything instantly. But to be fair, I was at a time in my life where that made sense. You know, I had just sold my company a year before and everybody was throwing everything my way and everybody wanted everything from me.

So it was a good time to raise the bar all the way.

But strategically, there are other times in your career when really the most strategic thing to do is to say yes to everything because it can be like lottery tickets, you know, like if you got nothing going on and somebody offering you an infinite amount of lottery tickets for free will, then how many do you want? You know, I'll take all of them, please. So I don't think that hell yes or no is something that should be applied to everything in life.

You have to know when you're drowning in opportunity or starving for opportunity.

Is that the only criteria by which you would sort of like gauge when to use this is like your opportunity cost? I think so. Off the top of my head here when. You're running CD, baby, you had to learn to delegate and you sort of like hinted in your book that we've run into this like small businesses run into the ceiling. I think my friend calls it the ceiling of brute force. Right.

Which is like you you get caught in this trap of, like, not delegating, doing everything yourself. What can you expand on that? And like, how did you learn this?

So first, that's OK, we'll define it. Every solo freelancer or person doing anything knows this feeling where you're so busy, you're doing everything yourself and you know, you need help. But to find and to train someone would take more time than you have. And so instead you just keep working harder and harder and harder until you break how I learned it.

I broke I hit that breaking point. I did exactly that. And then I broke. My company was three years old. I had eight employees, but I was still doing everything else myself. Right. Like I was just working seven a.m. to midnight, seven days a week. And a lot of things in the company still went through me, meaning like every five minutes one of my employees would have some kind of question for me, like, what do we do about this?

What do you do about that? And it was getting hard to get anything else done.

Like, I felt like I would just show up to work and just answer my employees questions all day long. And I hated it. I hit my breaking point like I really like deep work.

I really love focusing, you know, for work to turn into this constant state of every five minute interruption just made it unbearable. I stopped going to the office.

I started shutting off my phone until I realized that I was running from my problems instead of solving them. And I realized, like, this was kind of a do or die moment, like I need to fix this or I'm toast.

I just kind of had a long night of writing and thinking and reflecting on this. And I just realized I need to make myself unnecessary to the running of my company like this.

I need to do this. This is now super, super, super important. I'm at the breaking point.

So yet the next day it was like changed, man. I walked into work. As soon as I walked in the door, as usual, somebody asked me a question, oh yeah, hey, what do we do about this?

But this time, instead of answering their question, I called everyone together for a minute. I was like, OK, bend over here, Tracy. OK, all right everybody. Nikki just asked me what to do when a customer asks this.

So I'm going to tell all of you my answer. But more importantly, I need to tell you the thought process behind it. OK, here's what I think we should do, and here's why.

My rule of thumb is if this then that, you know, the big philosophy here is this. I want to make sure that everybody's happy about it and I'll explain my philosophy. And then I asked around to make sure that they weren't just pretending to listen. And I made sure that everybody got it. And then I asked Marlana over here to start writing this in a manual. I said, can you start a manual today?

Like, let's make this like the the company manual and wrote down the answer to this one situation and the philosophy behind it. And then everyone got back to work. And of course, five minutes later, it happens again. Somebody asks me another question. So once again, I gathered everybody around and we repeated the process.

So I just kept doing that until every last thing that was my job, even like I think I was still doing the accounting or the putting stuff into quick books or whatever myself, even that I said, OK, this is the last thing that is still mine.

So, no, I'm handing this off to you. This is yours now. And that was it.

And suddenly I was completely not necessary. I started working entirely from home and there was a funny moment where I'd like call into the office.

After not being there for a week, somebody would pick up the phone and say, Kay Bailey, hey, Dan, it's Derek.

He's like, Oh, hey, man. Like, how's everything going?

He's a good guy. You need anything is like, no, we're all set. Why are you calling? Yeah, I was like, OK, well, I'm just home. If you need any help with anything, he's like, we're all set man. Thanks though. And that was it. Like I was unnecessary.

So at the time my girlfriend had just moved down to L.A. to go to film school.

So it's like, all right, I'm going to come join you. So I moved down to L.A., which I thought was like a nice symbolic show that it's like, all right, guys, I'm I'm no longer here. This is up to you.

And then what was most interesting about this is that once it was done, like once, I was really not necessary. I still was working these 12 hour days because I enjoyed it. But now I was only working on the improvements and the innovations like the new stuff.

And to me, this was the fun stuff, like this wasn't work. This is fun. This is creating while I was away in California, my company grew from for.

Million, sorry, sorry, no, grew from one million to 20 million in four years, like it grew from eight employees to 85 employees while I was away, like just basically without me. To me, that was the lesson, like the huge difference between being self-employed and being a business owner.

There was it's actually from the book Rich Dad, Poor Dad by Robert Kiyosaki that I kind of learned this idea of, you know, you're a true business owner when you could leave your business for a year and come back a year later and find that it's doing better than when you left, that's when you're no longer self-employed, you're a business owner.

And lastly, for anybody interested in this subject, like if you think if this is really speaking to you and this is something you need the best book on this subject is called Myth Revisited by Michael Gerber. It says it way better than I could. I didn't discover that book until after I'd like a year after I'd gone through the process.

But when I read it, I was like, Yeah, there we go. This is the the masterpiece on this subject.

Somebody putting into words what you feel, right? Exactly.

That's a really interesting philosophy.

Right. Like you, I like the idea that you move from self-employed to a business owner when you can walk away.

Did you have any sort of like, feelings of I'm not needed in a bad way?

Like, oh, I think only that one week that I described, like calling the office and being almost like a little sad that that they didn't need me for anything. But I mean, that was like it was a fleeting moment and then it was just joy after that.

And then it would blow people's mind that I'd be down in L.A. and meeting up with somebody and especially somebody else who was still in that trap right there, like, oh, my God, I can't can't handle everything. I'm so swamped and I'd like to. How do you do it? You're like sitting here at lunch with me. You've got a whole company going on up in Portland.

I'm like, mm hmm. And I had to kind of tell them this tale. Like, I it was hard work, but I delegated everything and it just I had to I was really at that breaking point where I was ready to walk away if I didn't.

So you're such a thoughtful person. I'm curious as to like what you've learned about delegating that most of us would find surprising.

You have to have the long term perspective. You have to know that's like, all right, this is going to be harder.

Yeah, it's going to be harder at first for the long term gain. Right.

Like, if you realize that you're at this breaking point, your time is already full. You're already not sleeping enough, you're already working too much. And now you've decided that you need to hire and train somebody. Well, yeah, sorry. It's going to get even harder before it gets better. You're going to have to sleep even less until you've found and trained somebody to do it.

But then you keep your eye on the. On the horizon, instead of the obstacles here, look at the distance instead of today and know that it's going to pay off.

How do you think about the the pairing between ideas and execution?

Oh, you know, I've got something to say about this, don't you? I do.

I hope so. All right.

So, yeah, actually, that was a funny, like storytelling Segway, because this came from living in Los Angeles, where the people I was around in L.A. were all speaking in future tense.

And it was always about what they were going to do, the deals that are going to happen, everything. So, yeah, we're in talks with this guy, Idi Amin. We're going to be working on this thing.

Yeah, the pilot for the show, it looks like FOX is going to be picking up this pilot.

Everything was always future tense. At first I was smiling and.

Oh, wow, that's great. But after a while, I realized, like. Oh, I'm in everybody's speaking in future tense about these things that are going to happen and they never do. So what was all that hot air about?

And I felt like wearing a T-shirt that says, tell me when it happens, you know, like, why are we talking about it?

So it was during that time that a good friend of mine asked me to do a favor to him to hear out his friends business idea.

So people tell me lots of business ideas. But this this one was a kind of a bit of a breaking point because this guy insisted on making me sign an NDA to hear his business idea. Like, ordinarily, I would have just said, no, I'm not going to sign an NDA to hear an idea. But it's because of this situation. It was like a good friend of mine asked me if I could please as a favor to him.

I was like, all right, all right, here's your NDA.

And then I drove across town sitting at a restaurant and finally, OK, nice to meet you.

What's this big idea you want to tell me? And he said, OK, you ready? I said, Yeah, I'm ready. And he goes. It's online dating with music, and I said, uh huh, and goes to online dating with music. I said, Yeah, is there more to this idea? And he goes, Dude, that's the idea, man.

Online dating with music like, wait, do do you have, like, any implementation of, like, anything else? Now again, he's like it's like he's telling me something profound is, I don't know, online dating with music. And then he said, so here's what I'm thinking. Did my friend, you know, our mutual friend tells me that you know how to program. So I'm figuring that, you know, you can make this thing, you do the programming to make this thing happen.

I'm the idea guy like you and I can go 50/50 on this man. This thing is going to be huge, man. Online dating with music. I'm the idea guy. You're the execution guy. Or he said, you know, you're the programmer.

I was like, no, no, no, no, no. So I think I said, All right, look, how do I explain this? It actually took me till later that night to think of how to think of a nice metaphor. That was easy to explain.

What I wrote is that I think of ideas as a multiplier of execution.

Right. So let's pretend that we have two columns of numbers here. So an awful idea. Let's say that's a negative one, but a weak idea is a one. An OK idea is a ten and a great idea is a twenty. OK, and now imagine another column over here. That's the execution column. No execution, doing nothing about it. Let's say that's a dollar weak execution. A thousand dollars, OK, execution, one hundred thousand dollars and great execution, let's say a million dollars.

But the real point is that to make a business, you need to multiply those two columns that the most amazing idea with no execution is just you. OK, let's take a great idea with twenty no execution, one dollar. OK, that great idea was worth twenty bucks if you don't do anything about it. But on the other hand you could have like an OK idea and OK execution and maybe make a million dollars. But if you have a great idea and times great execution then you can make 20 million dollars or more whatever.

So that's just my rule of thumb way to explain this, why I'm not really interested in hearing people's ideas.

It's just not interesting without the execution.

I think that's a brilliant insight. I had another way of of coming at this exact same philosophy with different words, but it was adding too much value.

So we were used to working in boardrooms and people would pitch ideas for projects sort of like Shark Tank.

I mean, a lot of organizations have these like gates where, you know, the people who can allocate resources, decide which projects to fund.

And one of the things that I noticed was that the people making the decisions are always trying to make the ideas just a little bit better. So somebody would come to you with, like, you know what I mean?

Like, they would come to you with a 95 percent idea and you'd be like, oh, my God, have you thought of this?

This is going to move this from ninety five to ninety five point five. And I am a genius. Right. And what I noticed was that that willingness of the person to own the idea, to be motivated, to execute went down.

So the quality of the idea almost inarguably went up a little bit. How much is is sort of like irrelevant, but the ability, the desire of the person on the other end that to own the idea, to execute it went down and it always went down by so much that the expected outcome from the project is always, almost always worse off.

I love that you brought this up. I think this is a very underrated insight. Did you read I think it was Marshall Goldsmith's book.

Yeah, I think that's where I actually sort of like got the words around it, but, you know, like, yeah. It what got you here won't get you there. Yes. What got you here. Won't get you there. Yeah. I think the way he put it there in America the slang term is you say here's my here's my two cents on that idea, you know, so I don't know if that would it wouldn't make sense if you don't have that currency, no matter where you're listening.

But yeah, in the American slang is, you know, here's my two cents.

So Marshall Goldsmith in what got you here won't get you there said yet.

Don't add your two cents. And he gives a very vivid description of somebody coming to you with an idea.

And he said even if you have an idea for how it could be better, I'll just zip your lips, smile, say sounds great. Go for it.

Which is weird that it took me so long to to hit on this myself because I mean, I, it was on the other end of that and so annoyed that these people it's like well can't you see like how.

How willing I am to own this and run with it and I want to execute on this and like you're telling me, like do this one little, you know, change the color of my button from blue to red.

And I'm like, that is, you know, just lowers my desire to sort of lead this project.

And then when I got on the other side, I was like, oh, now I can have my value right. Like and then it took me a while and then I stopped doing it. I found this really amazing thing. Like, everything got better, people worked harder, there were more motivated. They own things instead of just being somebody who executes what they're told. I mean, they actually own the project as much as you can own a project and an organization.

And everything was so much better. And even if I had ideas that were like, oh, here's a roadblock, I would let them go as far as they could right before they had to execute on that part and then have a conversation with them.

And nine times out of ten they figured it out. So I never even had to say anything because they figured it out because they were in the weeds doing the work.

I love that about books that it's like, yeah, you and I both spirit. I mean, everybody probably probably everybody listening to this because. Yeah, yeah.

I've had this situation too, like my boss told me, to make this one change. And it's like I do it with a grumble now and doesn't do it.

And I love when the authors of these books that just take the extra time to think something through deeper and take the extra time to put it into good words and take the extra time to edit it down to a way that makes it spread, makes it easy to remember and communicate. It's just such a valuable thing. I love it.

Books, books, reading and reading books change your life at an early age. You read Awaken the Giant. How did how did that change things for you? Uh, yeah.

Tony Robbins awaken the giant within. Um, God, that was it's like asking someone what they learned from their religion.

The stuff that Tony Robbins preached in that book is, like, so deeply ingrained in me that it just feels like reality.

I'm embarrassed because I've never actually read it.

Well, you know, it's funny when I Tim Ferriss and I met for the first time in 2007, and, yeah, he told me what book made the biggest difference in his life, and I told him what book made the biggest difference in my life.

And then the next day we both went out and read each other's, you know, favorite. And both of us were like, Huh, no, it does nothing for me. And so comparing notes later, we realize that we both read this formative book for ourselves when we were teenagers. And so I think it's more about timing.

Like, I don't know if Awaken the Giant Within is actually a great book, but I read it at a very, very formative time when I was like eighteen or nineteen and just super ambitious and ready to take on the world.

And then not only that, but someone who I cared about very much and was gorgeous gave me this book and said, you need to read this.

So of course I read it with like maximum maximum suggestibility.

So, OK, let me try to think the the things in my philosophy that that are like how that book changed my life, the philosophies that I got from that, I think the important ones are you can change the way you feel about anything in an instant.

So if your emotions aren't working in your favor, you can just change them. And related to that, events are neutral. Like you can interpret events as good or bad. You can interpret a neutral event as crisis or as opportunity.

And he makes this great example of New Orleans funerals saying, like, even if you think of something that we think of just as objectively sad, like somebody you care about has died, well, look at how they do funerals in New Orleans, like they play the sad music as they're marching down the street with the coffin.

And at a certain point, the drummer comes in and around and it turns into a celebration as they dance and celebrate this person's life.

He's a perfect example of how you can change your emotions in an instant and you can feel about an event however you want. You can celebrate somebody's death with joy.

And the big idea then is you can choose whatever interpretation works for you. Whichever one you feel like taking on is is the one you can feel. So, yeah, your your emotions are completely under your control. And he gives specific techniques on how to do that about questions. So he talks about asking yourself better questions and how the questions you ask yourself change everything. Like when something goes wrong, you can ask yourself what's great about this. And he again, he gives this colorful example, some horrible thing that happened in his life, like a manager of his ran off with millions of dollars of his company, like Embezzled.

And he said, OK, I'm going to follow my own lesson. What's great about this?

And he said, nothing, nothing is great about this. This is horrible. He said, OK, keep asking.

Keep asking until he found something. He found a perspective on this neutral event that now empowered him instead of disempowered him.

He talks about what? You focus on changes everything, and again, the colorful story here, I can't believe I'm like remembering all the I got how old am I now? I'm 50. I read this book when I was like 18, 32 years ago. I'm remembering all these vivid stories.

Right. So he talks about you go to a party, just imagine yourself going to any random party full of a bunch of people and you take a bunch of photos at that party of people and then later you decide to show just the happy photos to somebody. And they would get the impression that that was a really fun, happy party.

But you could also take just the photos that you caught candidly, where someone was looking sad or alienated or lost and show somebody only those photos.

And now it looks like a really sad, depressing party. It was actually the exact same party. But you've just chosen a different filter. And of course, metaphorically, we all do that in life.

Like you could just look at a newspaper today and you can choose to get outraged by it or you could choose to get depressed about it. You could choose to get excited about it.

It's almost like a thermos, right? Like it reinforces whatever you're bringing to it.

Yes, it's exactly like a thermos, you know, but I mean, like your lens, if you put something hot and it's going to stay hot and if you put something cold and it's going to stick, I'm imagining some kind of like sci fi thermos where you could go, like and twist something and instantly turn from hot to cold if you.

Anyway, let's do one more.

So I think I got my idea of long term focus from him or the big ideas, like there's no such thing as failure until you give up, because until that point you're still just getting feedback like, no, you could have just tried a hundred things.

You know, the old classic example of Edison with the light bulb filament, you're just getting feedback like, OK, that didn't work.

What else? He talks about how people overestimate what they can do in one year, but underestimate what they can do in ten years.

And yeah, focus on where you want to go. Don't focus on what you fear. And he had he had a little story about how he learned racecar driving and he was like suddenly getting terrified. And he found himself looking at the wall like, oh, no, I'm going to hit that wall.

And he said, my trainer literally grabbed my head and turned my head towards the road where I wanted it to be going.

And he said, that's a great metaphor for it's like, look where you want to go, not at what you fear.

God, yes. Sorry. I guess I have a lot of these. These are just like these are so ingrained in me, like they all just feel like, well, yeah, that's life. That's reality. But the truth is, I, I got all of these things from that book that's so powerful.

What makes for good writing for you. Have you read it again. Actually since then I OK so I think I read it when I was 18 and like again when I was twenty and again when I was 22 and maybe one more time when I was like 25.

But that was like a paper book which then I've given away.

And so I think just like a year ago I tried getting it on Kindle and I looked through it again and it was just.

It was like somebody telling you that water is wet in the sky is blue, it's like, yeah, yeah, yeah, it was like, OK, this stuff is just too ingrained in me. I just I don't sorry, I can't read it again. It's just it's all just obvious.

How do you filter what you read now? It's usually either to solve a current problem in my life, like say if I'm I'm having issues with parenting or having issues with keeping up with my habits or or even like a knowledge problem, like I don't know who those old philosophers are. People keep talking about Nietzsche. I don't know anything about Nietzsche.

So I'll let go read a book to solve that problem. I often read just because I think that this book's insights could help my life right now, even if it's not a concrete problem. But like whenever I read anything by Mark Manson or Steven Pressfield, I always come away feeling like, yeah, that's a really cool insight. Like it wasn't to solve a concrete problem. I just I like their philosophies.

And then often it's just for curiosity.

Like, I just two days ago finished a big, long course on linguistics and that was a blast. John McWhorter, the history of language was fascinating.

I love reading about geography. I love reading about the culture of different countries. Yeah, I just read a book a few months ago about the culture of Finland and just found it fascinating. So, yeah.

How do I filter, though, knowing that what I'm looking for is what I just described, then how do I choose exactly what book?

I think I probably rely too much on Amazon reviews or just if there's a wise person that I like that I'm a fan of them. And they say that, you know, this book is a great book, then I'll go read that book.

Do you read it cover to cover? Like when you pick up a book, are you searching for something that you wanted to learn?

Like what's your process for picking up a book and then reading it?

Yeah, I don't skim. I know that some I know a lot of people skim, but I know I try.

Whenever it's like reading time I try to slow down my internal clock just OK, focus on just this.

Like this is a different pace than being online and clicking and surfing and clicking like this is. So yeah I try to read, just start to finish unless a book really sucks, unless it's like I'm a third of the way through, I'm like, yeah, I don't like any of this, then I'll trash it.

But for the most part I hear them out.

I go start to finish and most importantly, which we can really nerd out on if you want, as I underline every surprising or interesting idea that I want to think more about later.

And so then when I'm done, I take all of those underlying ideas and I put them into a text file. I usually just kind of put them into my own words. I remove their unnecessary words. I think I'm more of a harsh editor than most people. So yeah, I chop every unnecessary word. So now I have the core of this idea in eight words and then in that text file I separate each idea with two line breaks. So you no idea is on one line or maybe two or three lines.

But whatever it is, I hit enter twice to leave two line breaks before the next idea so that later I can write a little ruby programming script to pass them when needed.

Then later, yeah, I reflect on these ideas. That's why I saved them. I'm never trying to summarize the book.

I actually don't care about the book. I just want the interesting ideas inside so that I can reflect on them later and ideally, you know, add more to them myself.

Talk to me about the reflecting on them later. I mean, a lot of us highlight a whole bunch of things in a book. We're like, oh, that was amazing.

This is great. And then we're next book. Like, we never we never sort of like go back and think about or digest or do the mental work. It's sort of like making those ideas our own right.

OK, so I have a new approach to this. So I used to just take this one big text file with all my notes from one book and I would just keep those text files on my phone.

And if I was just sitting on the bus to get somewhere, I would just look at my folder of textiles and I would open one up and just kind of reread it and just kind of stop and look out the window and think about something interesting.

But then I found that, again, I don't really care about the book. I like the ideas inside. So here's a project that I've been working on for a long time.

I've just been dabbling with this for a long time.

I'm tagging every single one of those ideas from every book I've read since 2007. I'm tagging them with keywords and loading them into a database.

So now if I'm thinking on a subject like, you know, commitment or regret or hedonism or memory or pain, then I can just search for my notes around that subject and I can pull up like 173 ideas that came from twenty eight different books instantly.

But just browse these ideas because again, I don't care what books that came from anymore, I just want the ideas.

So I've separated them from the book and I'm keeping them as their own little atoms to play with, but then the main thing I do now is to pull up on my notes on a subject like this, like, say, hedonism.

And then with all of these notes in front of me, I open up my own text document to start from scratch with my own thoughts on this. So now it's almost like I'm in a room of some really smart people talking around this subject. And it's inspiring, really interesting thoughts of my own that are often like a reaction. It's like I'm it's like I'm joining the conversation of these thinkers.

I want to see what I can add.

That's honestly what my next book called How to Live. The book that I'm writing right now. This is kind of what the book ended up being. It's or it's grown out of this process of surrounding myself with a bunch of thoughts around one subject and then writing my own thoughts around that subject as it kind of a reaction to the others around me. It's metaphorically it almost feels like if I was a painter and I was allowed to bring a blank canvas into a great museum and I could sit in a room of my favorite paintings ever and paint my own, which is not imitating theirs, but it's influenced by I'm kind of building on that, inspired by that.

Does that make sense? I think so.

I mean, what what I one of the geeking out part of me is like, OK, so you have this private database and you tag things so that you can easily search it. And when you're thinking on a topic, you look at it and through that regular digestion and hitting on those things, you make them your own and then you you write about them.

Yes. So it's about internalizing it, not memorizing it. I used to so I'm into Anqi and flashcards and spaced repetition. So I used to think I wonder if I should somehow feed all of these ideas from all of these books into space repetition so I can memorize them.

And something never felt quite right about that. They took me a while to realize what it was, is that no, I don't want to memorize these people's thoughts. I just want them to lift up and inspire my own thoughts, which I just I really need to internalize these things. And to me, that only comes from reflection and giving it time. So, yes, like you said at the beginning when you said I often would read a book, go, wow, that was really good.

And then on to the next book. But as time went on, I thought, wow, I'm not I'm not remembering these books unless I really stop to reflect. I feel like the reflection time is when you really learn the moment when you read somebody else's idea. That's a wow moment, but you don't really learn it until you've put aside the time to reflect on it.

And is that where you come up with your directives? Oh, the directives.

The directives I think came from sorry, everybody listening. Shayne's talking about. Oh sorry. Yeah.

Something I've something that I've blogged about a few times, which is this idea of taking taking an idea and turning it into a a directive which is meaning telling you to do an action.

If you go to my site, if you go to Sivers Dog or if you read anything I've written or even the TED talks I've put out into the world or whatever, you might notice that I like being very succinct, maybe not in conversation with shame right now, but when I put something out into writing, I like being very, very, very succinct.

I like chopping out every possible word, leaving only the words that need to be there. So I noticed that as I was learning about certain things, I felt like most books use way too many words. And I came to this idea that probably the most succinct way to communicate an idea is to focus on the action itself. Like if you command the action, then the action like a seed.

I think there's like a nature metaphor in here somewhere that the the action has the seed of the idea in it, that the action carries the idea along with it. You can talk for 400 pages about calories and this kind of fat versus that kind of fat and protein versus that. But instead, you could just tell somebody, eat this, don't eat that.

Those actions would carry that two hundred pages of information in the actions.

And so, therefore, the the succinct directives, the actions, please my minimalist, ruthless editor sensibilities more.

I want to talk about characters a little bit more. And what's interesting to me when I think about objectives is.

They're great if you can get them from other people, but they're different again, going back to this imitation versus like knowing and understanding.

So you're coming up with these directives, like you're doing the work, the mental work, like you have an experience, you're reflecting on it.

That experience can be yours or it can be from reading a book or somebody else's story. But you're doing the mental work of reflecting, integrating, digesting, and then you're coming up with these directives, like so much of life today, is like just give me the directive.

And we haven't done the work in space.

Repetition like Anqi as well as flashcards. A lot of people say, yeah, just give me somebody a deck so I can learn JavaScript or whatever, but I'm like, no, no, no, no, no, no.

Like the whole point of flashcards and memorization is like after you've learned this thing, you make the flashcard to help your future self remember it like the flashcard is not the moment of learner.

So yeah, I feel the same way about the directive's, although there are different subjects in life where I want to know more about this or not.

So the actually the example that I gave about this kind of fat versus that kind of fat in these calories versus those calories, I don't care about that subject so much. So I would not want to read a 400 page book about nutrition and diet. That's an example where I just want somebody to tell me what to do, tell me, you know, eat this, don't eat that. That's all. I don't need the details. And so because I feel that way about nutrition, I can imagine somebody else feeling that way about, say, technology or stoicism or language learning or whatever it may be like.

No, I don't want to talk around this subject for 300 pages. Just can you tell me what to do in one page and then I'll just do that like and I think this comes down to trust.

If you trust the source, then you don't need all of the supporting evidence.

I would add one caveat to that, which is I think and the environment's not changing rapidly. Right.

So the source came up with is in a certain environment and you just have to make sure that that environment still exists, because if it changes rapidly, then the source is likely to be right. But right at the time or right for that particular environment and then you won't know what happened.

Why would you be thinking of that in April 20, 2014?

Let's do a deep dive on directive's. Why don't you give me some of your categories and like go through some. I don't want to put you on the spot, but.

Oh, sure, I don't like how to be antifragile or thriving and unknowable world.

This is like this is like you're you're a talk show host and you say, hey, why don't you perform one of your songs for us?

Sure. I'll be glad to do that. No, really, I don't mind. All right. Hold on. Let me pull up.

We all like the Antifragile concept.

It's really out right now to exactly how to thrive in an unknowable future. And again, to give context, this is where I've read a bunch of books on this subject. I took a bunch of these book notes, lots of paragraphs, and kind of condensed them down into these, what is it, six directive's one, prepare for the worst since you have no idea what the future may bring.

Be open to the best and the worst. But the best case scenario doesn't need your preparation or your attention. So mentally and financially prepare for the worst case. Instead, like insurance, don't obsess on it. Just prepare, then carry on appreciating the good times. How to thrive in an unknowable future. No to expect disaster. Every biography of a successful person has that line. And then things took a turn for the worse.

So fully expect that disaster to come to you at any time, completely assume it's going to happen and make your plans accordingly. Not just money, but health, family, freedom. Expect all of it to disappear.

Besides, you appreciate things more when you know that this may be your last time seeing them three own as little as possible depend on even less. The less you own, the less you're affected by disaster for and this is straight out of antifragile. Choose opportunity, not loyalty. Have no loyalty to location corp or your past public statements. Be an absolute opportunist doing whatever is best for the future in the current situation. Unbound by the past have loyalty for only your most important human relationships.

Number five choose the plan with the most options. I got that one from Kevin Kelly. The best plan is the one that lets you change your plans. For example, renting a. House is buying the option to move at any time without losing money in a changing market, and number six, avoid planning for maximum options.

Don't plan at all since you have no idea how the situation or your mood may change in the future. Wait until the last possible moment to make each decision. Funny thing is, I posted that in 2016 on my site and I just like last month in March 20, 20, in the middle of quarantine and all that like went back and read it, just kind of smiling and nodding like.

Yup, prepare for the worst expect disaster. Yup.

Dude, this is like gold. I just want to sit here and listen to you like keep going on this stuff. What are the other what are the ones that stand.

We've got to do the younger one. You and I are both. Hey, hey. Actually Shane, have you heard of Charlie Munger.

I think you would vaguely. I mean, I think I remember coming across him in a headline somewhere.

So you and I are both Mongar fans, so I'll just do this one more.

That is totally a not a ripoff, but Charlie Munger's idea, I think it was in poor Charlie Charlie's Almanac, one of his speeches to one of the schools where he did the reversing it like prescriptions for misery, guaranteed prescriptions for misery.

How did you just happen to know that?

Yeah, thank you. That was it.

And I just I loved that format. And so, yeah, I tried my own version of that, which was how to stop being rich and happy. No. One, prioritise lifestyle design.

You've made it so it's all about you now. Make your dreams come true. Shape your surroundings to please your every desire, make your immediate gratification the most important thing. How to stop being rich and happy. No, to chase that comparison moment, this is from the book Stumbling on Happiness. You have the old thing. You want the new thing. Yes, do it. Be happy for a week. Ignore the fact that the happiness only comes from the moment of comparison between the old and new.

Once you've had your new thing for a week and it becomes the new norm, just go seek happiness from another new thing. Number three, buy, not rent.

Why rent a house, a castle, a boat or a car when you can buy?

It's not about the thing, it's about identity. This shows who you are now. Number four, internalize your new status. You worked hard to get here, celebrate, relax, admit that you're in a different class of people now with different needs. Understand there is no going back.

Number five, how to stop being rich and happy to be a connoisseur. Learn what others say is the finest. Insist on only the finest. You will now be unhappy with anything but the finest No.6. Get to know your possessions. Now that you own the best, it's time to focus on what you've got. Learn all about the features of your new possessions. Spend more time getting your surround sound and your heated floor just right. Work out the whole solar panel charging of your Tesla car.

This is important. And lastly, number seven, how to stop being rich and happy, acclimate to comfort, eliminate every discomfort from your life. Blame others when the world seems hard and is not living up to your standards.

So beautiful and so true. I just I really like this format of. Making things as succinct and as actionable as possible, so I really need to turn all of these into a book I have just like a rough draft of a book called Do This. That would just be a book full of these directives.

I love that idea. I hope you do that. I think the world needs. I hope.

I hope you all email me and tell me to do that and keep annoying me until I do it.

I well, I'll just you know, what I'll do is I'll just because I can program I'll just create a script to email you every five minutes. Yeah.

I'm curious, like how you go about making important decisions.

Well I, I don't aim for reality and I'm actually really interested to read your book because right there the first like I said, I just started reading your new volume one last night. But the first thing I underlined in it was the thing about blindspots. It was like right there in the first few pages. And he said about blind spots.

And I think, OK, this is actually a new idea to me because. I'm not used to aiming for reality. In fact, I used to have a record label called Artificial Records and my slogan was, quote, Why settle for reality? I think the Tony Robbins stuff I said earlier was a bigger influence on me than searching for reality. Because you heard maybe the common thread in there is it's about looking for a perspective that helps me. Right.

Like, I don't remember what book I got this from, but credit to this goes to some book out there that says. It gave this idea that you imagine that you need to walk across an elevated plank, but you're too scared, so you're not doing it, so does it help you to think that the plank is lying on the ground?

Right. Like, if it was just lying in your back yard, you'd walk across that plank.

No problem. You wouldn't fall off of it. You wouldn't be scared falling off of it, because why would you fall off of the plank just there?

You walk across it. What's the big deal? So does imagining that that elevated plank is just lying in the grass in your yard help you? Yes or no? Does it help you to believe that there's a safety net below you? Yes or no. Does that make you walk across it?

Does it help you to picture that on the other side of that plank is a burning building and your child is inside? And also there's a hungry tiger behind you chasing you, and it's going to kill you in three seconds if you don't walk across that plank. Now, does that get you to walk across the plank?

OK, well, then that's the winning perspective.

Whatever makes you take the necessary actions is the perspective that helps you. I'm never aiming for reality. I'm trying to make decisions usually based on finding the perspective that helps me take actions like I'm not even aiming for results or effectiveness. The real answer is I think I'm usually making life decisions because they're fun.

Granted, I'm not an investor. I'm not making investment decisions.

Right. I usually I choose things more based on the the compass of fun and adventure. Right.

Like having a different perspective can make something more of an adventure. If you think of the stereotype, the old classic stereotype of the Explorer with the the pith hat. Right. Going off into darkest Peru to places that no one has explored. Well, I like doing that with perspectives. I often think of any random thing and I think of what approach could be fun or could be exciting or could be new and uncharted, then that's creative, right? Like, I don't even care very much if this fails, because my only goal was to just try it out.

Like, let's see what happens if I take this approach.

I think it's sometimes like, you know, just like you asked me about Awaken the Giant within and I have to try hard to imagine what of me came from that book.

I think it's actually the same thing with music. We haven't really talked about music itself, but I think I'm so damn influenced by the fact that I was a full time musician for fifteen formative years, like from the age of 14 until twenty nine.

All I wanted from life was to be a successful musician. And so I think now I still approach life like I approach to music with lots of, you know, let's see what happens if I do this.

Let's see what happens if I run my voice through this guitar pedal. Let's see what happens if I use this flute like a drum. And I think that music thinkers were probably my first favorite thinkers like Brian Eno, for example, or John Cage here.

I have a I have at all times and some of my favorite Brian Eno quotes.

I love these quotes so much, not just Brian Niños, but like from a collection of musicians that whose ideas inspire me. I ended up making a little website called Music Thoughts Dotcom, where I put all of these inspiring quotes about music. Here are four from Brian Eno. Just to give a concrete example, art doesn't end at the edge of the canvas. Its position in the world, both physically and culturally, can completely change the meaning of the art.

OK, that's one idea. Instead of writing songs, let's make a hypothetical film and then make a soundtrack for that film. That's an idea. A favorite one, cut a vital connection, find what's holding everything together, then eliminate that. And last one, when you listen to Miles Davis, how much of what you hear is music and how much is the context, like all the things you know about Miles Davis.

So when you're listening to music, you're actually, you know, quote unquote, hearing all the stuff around it, too. OK, so I've got like a thousand of these on this website called Music Thoughts dot com. And I think I forget that I'm still taking, like, this experimental musical approach to life. So when you ask how I make decisions, I think it's very similar to like Brian Eno making musical decisions in the recording studio. Like this approach.

Sounds fun. Let's try this. I like that a lot.

I want to go back to something you said at the beginning of this, which was whatever compels you to take action. But how do how do you decide what actions to take in in a situation?

Hmm. I don't know. I think that's just one of those. Every situation is different. I think you just sometimes you have a concrete goal, right?

Like, I need to exercise more. What philosophy what mindset is going to help will help me.

Yeah, right. But other times you just don't really know what to do. All right. I'm going to give a concrete example from my life that is kind of personal. But after I sold CDs, baby, I felt really lost and lethargic for a year or two.

I didn't know what to do with myself. I felt like I had peaked.

And I dabbled in this and dabbled in that and thought, maybe I'll do this, maybe I'll do that. But then there was one moment on one airplane where I was just reading something. And what it was doesn't matter because it was just a random story about Benjamin Disraeli or something.

But there was a sentence in there that made me go, oh my God, I know what I want to do. And it was just talking about how Benjamin Benjamin Disraeli never shied away from the spotlight, that he he courted attention and took on the extra responsibilities of courting attention. And that tiny idea to me, just like it just set off a bunch of other things in my head, like, oh, my God, I've been running from responsibility because I didn't like having 85 employees at KDDI baby.

And so I've been wanting to avoid all responsibility for the rest of my life.

By doing that, I'm glad I'm turning invisible. I was considering legally changing my name, but oh my God, if I step into the spotlight. More instead of less, and just take on that little bit of responsibility, that extra responsibility, then, oh my God, I know what I want to do now.

I don't want to be this like X music store guy. I want to be like a writer, speaker, thinker. Got a guy. I want the TED conference to invite me to speak and I want people to want to hear my thoughts on things.

I'd like to buy books of my thoughts.

Like at the time I was just a guy running a music store and this was a totally new idea.

But Shane, it was like the first thing in a year and a half that made me, like, bolt up out of my seat and like instantly I was like, oh, my God, yes, yes, yes, yes.

I know exactly what I want to do.

And it just it turned into action. Like when the plane landed, I just bolted into action and made things happen for the first time in a year and a half. So it's like I didn't know what was the right action to take. And I didn't even try to ask myself, is this the right action to take?

I think it's just you can tell when something feels like the right action to take.

That's really interesting, because when you said that was what I sort of like, internalized a little bit was like, it's not the tactic, it's the direction. So you knew where you wanted to go, not necessarily how to get there. I mean, you've lived it.

No, I didn't know. Sorry. But like, until that moment, my plan was to legally change my name and disappear into Europe and be an open source programmer.

Yeah, yeah. But I mean, like but then you changed. You wanted to be this thinker, you wanted to do this. So you came up with this this direction that you wanted to get to. And then it was a matter of like establishing those tactics or, you know.

Oh yeah. And then making a plan kind of, you know, relatively easy. The easy part, once you know where you're going, once you pick a place on the map and say, I want to go there, it's like, all right, well, just that's northeast of here.

Let's head northeast.

And of course, you're going to adjust along the way to continue to use our explorer with the atmosphere.

I don't know if a lot of people think that way. I mean, I don't think that's maybe as common as as we're assuming. I think a lot of people are just like what's best for me in this particular moment without necessarily a direction. I'm no expert at this.

But to me, that would sound like. That's how I felt in my year and a half of muddling around, right? Oh, I think we all feel that way at various points in our life. Right. Switching gears a little bit, what's the biggest mistake you've ever made? Oh, and how did you recover from that?

Did I try?

The biggest mistake is the only one that I can say like a really objectively.

Yeah. That was a big, huge mistake. Was carelessly wrecking what could have been a great romantic relationship.

So, yeah, sorry, Ray, but let's talk about my second biggest mistake, because that was financial. So it feels like it would fit in better here. I want to dive into this relationship.

One, if you're OK talking about it, what happened with your knowledge was give it over.

There's not really I mean, I don't mind. I've never talked about it publicly, but yeah, I'm going to change her name and call her Ray. And yeah, she was amazing and wonderful and we were totally in love. And then in some, like, split weird split second weird moment when we were hanging out in Singapore, just I got like some bug is something in my head that bothered me about something she said.

And I just kept it to myself instead of bringing it up. And then while she was asleep that night, I called a friend of mine to say, yeah, what should I do? And my friend was like, just run, run the other way. This is clearly not working. Just get out of there. It just tell her sorry and get on the next plane out and. And I went, yeah, I guess you're right, you know, giving me a whole bunch of giving me that perspective, speaking of, you know, different perspectives on any given thing, my friend gave me that perspective in that moment.

And so when she when Ray woke up in the morning, I said, sorry, I'm going to get out of here on a plane today. We're done. And she was devastated and and I called. They left. And so a couple epilogues to this that actually make the story is that. A couple of months later, that same friend that gave me advice on what to do in that moment was doing some reading about relationships and going to see a counselor and learning some stuff and said, hey, guess what?

I found out I'm what they call love avoidant and and just feel me like what that means.

And I was like, oh, my God, I have those tendencies, too. And I thought, man, I really called the wrong person that night, like I was in such and in a suggestible, influential state of mind that if a different friend would have told me, like, dude, go back in there, that you love her and she loves you, do not let this go. Relationships have like times that you need to work through.

Do not get on that plane, get, you know, get stay with her.

I would have said, yeah, you're right, you know, but instead I randomly called the other friend.

In fact, I actually tried to call three or four different friends.

And the one that I talked to was just the one that happened to answer the phone just by chance.

And so I destroyed a great relationship.

And so another epilogue is that sometimes when that happens, you never talk to the person ever again and you never get to apologize. You never find out what they were thinking. But in this case, I I did talk to Ray again many times. And I think like a whole year later, I told her the full story of what happened that night. It was just that one thing she said on the subway that bothered me. But I kept it to myself and I didn't talk with her about it because I didn't know how.

And she said the sweetest possible thing.

She said, like, you know, you and I were always so good at talking on the phone because this is actually, you know, we're doing this over the phone. And she said, I wish she would have just like gone to the next hotel room or like called me from the lobby. And we could have talked about it over the phone. I went, oh, God, that is such a beautiful thing to say.

And then when I told her the whole story of what happened, she said, Yeah, I'll admit I don't think I've ever tried so hard in my life.

She said, I don't I've never been that in love ever in my life. I've never been so hurt in my life. That was really devastating. But then we continued to talk about it. And the funny thing is, she's probably my best friend today, like we talk all the time, but relationship wise, it's like it's too late. Like it's it killed that thing. So, yeah, that's probably my single biggest mistake.

Wow. I just told that story to Shane on the podcast. Hello, World.

What is love avoidant. I mean, I don't know exactly. Here, let me Google that for you know, I don't know.

I haven't dove into that. I just took it as a I think it taught me to to take these things more seriously, to not be lighthearted.

There's a beautiful line in the movie before Sunset with Ethan Hawke and Julie Delpy.

I believe that's the third one. They made three of them.

So the first one was before sunrise when they were in their 20s. Then they made before midnight, I believe, in their thirties, and then ten years later they made before sunset. I think I think that's the correct order of the titles.

But it was in the third one, which I generally didn't like that movie because they were all like, now they're married and they're just fighting for the whole movie. And I didn't really like seeing that.

But there was one killer line where they're reflecting back on when they met twenty years earlier and what they did in that first movie twenty years earlier is they just decided to trust the universe and they didn't even trade phone numbers or last names.

They just said, I'll meet you back here in a year at this spot. And she said, OK, see you here in a year.

And then they departed. And so now, twenty years later, in the third movie, they're going, God, why did we do that?

Like, what were we thinking? Like, why not just trade phone numbers?

And one of them said, I know why we did that is because when you're in your 20s, you think that these amazing loves will just come all the time and think, oh, there's a you know, that was a really sweet meeting.

But, you know, if this one doesn't work out, I'm sure there are plenty of others. You said then you get to your 40s and you realize they don't.

Those are really, really rare. So I think that's why I still objectively, when you ask what's your biggest mistake, the first thing that comes to mind is like that, me messing up that relationship that was like me not taking it seriously enough. And I think it's so impressive that as I continue to know her now, she's still like the most amazing person I know.

And I messed it up. And what's funny is after that all happened and I told some friends about my deep regret, different friends than the love avoidant friend, all of my friends do, the thing that friends do to each other is they say like, oh, dude, it's all right. You know, I'm sure, you know, it's for the best.

I'm sure something inside you probably knew that this wouldn't have worked out anyway. Like, no, no, no, no, no, no.

Hold on.

We should not sugarcoat everything because we really learn best from pain, like pain teaches us like nothing else, I think I need to feel the pain of this mistake and not write it off. It's like, oh, it's for the better anyway. No, it's not. I need to feel that pain so that the next time something like that comes into my life, that I don't make the same mistake. Yeah, man, you definitely messed that one up.

Is it hard being friends with her? No, no. She's amazing. She's like the most forgiving. Wonderful.

I don't know how to. Her heart is enormous. It's amazing. So, no, we're just. We're awesome.

That's awesome. What's your your compass? Who.

Uh huh. It's situational, it's not steady, sorry, that's not the admirable answer, but I think I think maybe because I'm exploring so much, I like that metaphor today. I've never used that the you know, the pith hat in the in the darkest Peru is not what they say in the Paddington book, the jungles of Peru. Anyway, explorers don't go in a straight line very much. We're exploring. So I often focus on an aspect of my life that's lacking and then I'll enhance it until maybe it's almost overflowing.

And then I turn my attention to whatever aspect is now lacking after that. So I think it's really interesting that we all have conflicting needs simultaneously. At the same time, we have a need for stability and a need for adventure, that we have a need for the comfort of the known and for the excitement of the unknown, like we have those needs at the same time. So I imagine that the perfect person would plot a path exactly like perfectly between those two needs.

But more likely and in my case, I tend to be a bit of a pendulum swinging back and forth. So yeah, I think my compass is not steady. It's situational.

I think that's really interesting that you said plot this perfect path between them. I think that would be less interesting life maybe.

Well, you know, some people like this approach to life like so James Clear wrote this masterful piece of a book called Atomic Habits.

And if you take that book all the way to heart, I could imagine someone taking all of their important values and making sure that they address them all every day or every week. You know, I need a little bit of time for adventure.

I need a little bit of time for what's known. I need a little bit of learning, a little bit of creating, a little bit of family time.

And that is amazing and admirable. And I'm sure there are some people that would thrive.

I mean, I would probably thrive if I lived like that. But I guess we all have a nature that a way that comes sort going say comes easiest to us. But maybe maybe our nature amplifies certain ways, like we can do things that are against our nature. But if we do things that are in line with our nature, then those things are really supercharged. Right. Because that's just our nature. You know, cheetahs can also swim, but a dolphin does it better.

I just don't find myself to be that kind of person that can do one thing for an hour and something else for two hours.

And then there's for an hour and this for 30 minutes that I just I throw myself completely into whatever I'm doing, almost to a fault. I love just doing one thing all the way.

And I'll do that for hours or days or weeks or months or sometimes, like in the case of Cry-Baby, I did one thing for ten years and then at a certain point I think, OK, I'm done now.

I'll do something else, but I obsess. That's beautiful. I love that.

But I wanted to make a point before I went back to habits, but which was sort of like working with the world versus working against the world.

Right. And the the way that you sort of mentioned that made me think of that.

I'm going to look up a quote by Joseph Tuzman, and it's so indicative of this.

He says, What the people must learn if he learns anything at all, is that the world will do most of the work for you, provided you cooperate with it by identifying how it really works and aligning with those realities. If we do not let the world teach us, it teaches us a lesson.

Holy crap, that's good.

And I think that's just a beautiful sort of like what you were hitting at. And I think that's just another way of looking at it right where we can fight our reality.

But it takes a lot of work and effort or we can align with with who we are and our realities or how the world works.

And it takes a lot less work and effort. And when we do that, we're amplified. So you can think of it as like tailwinds versus headwinds or a nice one.

Yeah. Thanks for pulling up that quote in. And bringing up that subject, because I think I spend a lot of time feeling a little bad about my nature, like I loved the book Atomic Habits and James is a phenomenal writer.

Yeah, but then I just look at I look at my actions and I just dive completely into one thing at a time.

And then I feel like I should be more like the atomic habits role model. And I just I'm not. So I that's a really nice way that you put it with TED headwinds and tailwinds and nature and just calling it the world instead of calling it your nature, like, well, this is your reality. We're all experiencing our own reality. And in my reality, yeah, diving into one thing at a time is the way that the world rewards me.

I think that we're should is really interesting. Right. Like a right. You said I should be this way. So you're feeling some sort of like guilt about not being the way that you feel you should be. But like, do you actually want to be that way? Like, I mean, there's there's so many ways to dive into that.

Like, I'll do one more Tony Robbins quote. He calls that shooting all over it. So.

OK, so. Yeah, well, I mean, look, I love changing my mind. I love having my mind changed. I love changing. So, yeah, when I'm reading Atomic Atomic Habits, for example, I'm sitting there going, yeah, yeah. This is the way to live. Right on. Yes. And in that moment, yes, I want to be like that. There have been many ways obviously like where we're all walking instead of crawling.

Right. We've all learned to we've all changed in our lives. And so there are some ways that you might have said when you were 16, hey, this is just the way I am.

I'm always going to be this way. But then at 36, you are very different than you were at 16. And no, it's it turned out not to be true.

So I'd like to think that that can keep happening. So even at the age of 36, you could say, you know, this is just my nature. This is how I am. But then at fifty six, you can be very different. You could have taken on some new skills and maybe it was gradual, but you can be a very different person that you used to be. So, you know, we can all construct who we are.

I think, speaking of who we are. Do you have foundational values? Is probably change on situation.

Yeah, change on situation, too, based on a situation like a few months ago. Again, here we are in April 2020. A few months ago, I would have said that travel and cultural exploration was one of the most important things to me.

This is why I moved to Europe. I'm living in England right now. I moved here so that I could travel my ass off and visit. I have a list of 50 places in Europe that I've read about, learned about, know about, but never been to.

I want to go to all these places. I want to learn the culture in each of these places.

If you would have asked me a few months ago, Derek, what are your foundational values? I would have said, well, shame No. One, cultural exploration, travel.

And yet here we are in a quarantine, which I was sad about for a minute. And then I had to just question that, like, OK, really, is that the only way I'm going to learn about other cultures is to get on a plane and go there and walk around like or is that a bit of a red herring?

Like how much did I really learn about Turkey from walking around Istanbul? Wouldn't I have learned more about Turkey by reading three books about Turkey, maybe watching the top five most popular movies in Turkey, and maybe scheduling phone conversations with twenty people from Turkey?

You know, that's the same number of hours invested, but I think I would learn more about the culture in that way.

So, hey, I can do that from anywhere. So. All right, my values have just changed.

You know, travel is no longer my most important value, which means that I guess it was like friends of convenience, you know, like those friends in high school that you were friends with because they lived next door. But and you weren't really that good friends. You know, as soon as you moved away, you never talked again. So I guess you weren't that good friends. So I guess travel wasn't really that much of a foundational value for me, was it?

If it's if I was ready to let it go in a minute.

So if I ask myself what doesn't change now, what's invariant invariant good one.

I love changing my mind. I love understanding a different point of view. I love creating useful things, whether that's books or articles or software companies or who knows what in the future. Yeah, I think those are my big three. I love changing my mind, understanding a different point of view and creating useful things. If I look back decades, those are always there. Those don't change.

And, you know, it's really nice that I actually just thought about like yesterday morning when I woke up, this was one of those like five thirty a.m. before.

I feel like getting out of bed thoughts is that I love that all of the things I love that mean the most to me in life. Don't take any money. Like, Oh, that's interesting.

Like, I often ask myself what I would do differently if you were to suddenly give me a hundred million dollars or a billion dollars. I'm like, just open up my journal. In fact, I have a recurring journal on this subject I. A journalist that I call them topic journals are thoughts on where I come back to certain subjects repeatedly, so I just give them their own diary on that subject. So this one is called Richard Text. What would I do if I had a hundred million dollars?

And they often do that as some kind of like brainstorming thought experiment. And over and over and over again, every time I try, I'm always stumped, like I actually try really hard.

I ask really hard, I really try. But every time the answer is basically nothing like if you were to give me 100 million dollars, I just give it right away because I just won't use it for anything.

I just don't want it. All the things that I love the most in life, just learning, thinking and creating it doesn't take any money. And in fact, money is probably a distraction that would take me away from those things if I suddenly had to, you know, attend events or whatever, because, you know, wearing a tuxedo to attend to this event.

Now that I have been given the Nobel Prize, like I don't want a Nobel Prize because that would take me away from these things, you know what I mean? Like, put in whatever example you want there. But no, that was a nice thing to realize in bed yesterday morning.

It goes back to the notorious big man. More money, more problems.

I thought that was Warren Buffett that said that he doesn't he doesn't strike me as a guy with a lot of problems.

True. How did you become a minimalist? Like where does that come from? Where you always that way?

No, it's because I moved house a few times and I think, like I said earlier with my my woe is me story of the relationship, I think you learn best by feeling the pain so you can preach minimalism to people, but then they can still go by that desirable thing.

I think it's only when you felt the pain from having too much stuff that you finally get it right.

So I used to have too much stuff and I moved house like three or four times and every single time I'd load up the big U-Haul van full of my stuff and then get to the new place and unload the stuff. And and, you know, the first time it was annoying. The second time it was really annoying.

The third time I was like, oh, my God, why do I have every time I unpacked the stuff, what is it for? Why do I have all this stuff?

Yeah. Then it was an accident of fate that I moved to. I moved to Portland, Oregon, while Cry-Baby baby was in full swing, like it was just taking off when I moved from the little village of Woodstock, New York, out to Portland, Oregon. And because I was just so damn busy with work, I put all of my stuff into storage temporarily, meaning it to be like for a few weeks until I could find a home.

But then I ended up living at my grandma's house. And you realized you didn't need all this stuff.

This stuff stays in storage for six years until finally, six years later, I just as a present to my employees, I'm like, OK, everybody, help yourself to my stuff. Everybody can have one thing.

So, you know, somebody took my guitar, somebody took my speakers, somebody took my mixing board, somebody took this and that. And, yeah, I just gave away everything I owned.

The last thing that I had to do that nobody wanted to take, of course, were my diaries. I used to have like twenty or thirty big notebooks that were my diaries every since I was a teenager.

And I looked at them and I was like, yeah, I really had to lug these around for the rest of my life. I just threw them in the dumpster.

If your house was burning, what would you grab?

My kid? That was easy.

OK, what what non-living thing or turtles living?

Yeah, I guess now I know you're going to say your kid. I was like just Fraserburgh actually.

Yeah. I have a real answer. I have all of my passports and yes, it's plural in a little Ziploc bag for that specific purpose. That's like. I actually get you all of my, like, debit or either Espie or, you know, I mean, I've just, you know, it's it's just different subject. It's, you know, I left America ten years on my Explorer mission, you know, and seeya. I've I have five different driver's licenses from five different countries.

And I have like four different resident I.D. cards and a few different passports from different countries.

And. Yeah, and I keep them all in one folder. So it's like in case of emergency, actually, I put them into one safe place for that purpose, like. My one thing that's irreplaceable and I keep a little USB backup of my hard drive in there so that I've had this happen where my computer just completely dies and like, all right, I just take this little USB stick. I stick it into any new computer. I'm good to go in 30 minutes.

So, yeah, those things are in one grab bag like everything else can be bought and replaced. Those things would be really hard.

How old's your son now? Eight. That's a great age, man. Like that is such a fun time. Yeah, well, they've all been fun times.

It's funny, I did that to somebody once. I was like when my kid was four, I talked to a dad whose kid was eight and I said something about like, oh, I can't wait till he's that age. And he said, you know what I mean? We always say that, like, not the time you're at. It's always the best time.

Yeah, I've noticed that the people that are around me that are the unhappiest parents have almost something universally in common, which is you can tell when they first have a child that they're going to be an unhappy parent because they're always hoping for the next phase. Right.

And so this is my heuristic for identifying people who are sort of like unhappy parents but haven't admitted it to themselves. So it's like when their child's in diapers, it's like I can't wait until they're out of diapers. And then when they're out of diapers, it's like, I can't wait until they go to school. Right. Like, my life will be so much easier when just this next and you're always like you're never in the moment with them.

You're always just like, I can't wait to the next phase.

Wow. But they tend to be like that across the board. Like I if only my spouse or partner was like this, then I would be happier if only work recognized my value, if only like it's always this conditional, you know. It's a really interesting I don't know how accurate it is, but I mean, anecdotally, it seems to hold. Yeah, to me, the person I knew that was most like that didn't have a kid, but she was in a perpetual state of quote unquote.

I'm going through a hard time right now.

And at first I thought I just happened to meet her when she was going through a really hard time.

But I knew her for years and years and years and years and years. And nope, she is always going through a hard time right now. It's just a way of seeing the world, it seems. Yeah.

I mean, there's a great quote. I forget who said it, but it's like people show you who they are. Let them. Hmm.

Which is interesting because we often meet people going through like a hard time or we write this off. Right. Like somebody is like, oh, you know, I just can't wait till they're out.

They're having a bad day. But then it gets reinforced over and over again. And then you're like, you know, but you've mentally just sort of like walked away from it.

What's the most common mistake? You see people repeat over and over, the most common.

Drinking alcohol. Sorry, that's not profound, no. Do you drink a little bit, I mean, every few months I'll have a drink, but it's, um. Yeah, sorry, that's not profound. I just tried to quickly think, what's the most common. Yeah. You didn't ask me what's the most important to addressing humanity, but yeah, that's the most common comment. But I don't I don't like drinking or abusing like walk me through that a little bit more.

A lot of people, you know, are on that grey area between them. So I think the the mentality that says it's, hey, you know, anytime you get together with friends, of course you need alcohol.

I'm having friends over get the wine. I think that that Blur's kind of quickly into like, well, we need that. We're having friends over. We need wine.

I wish that at that point becomes like something a little close to addiction. But I don't know that sorry. I don't have profound thoughts on this, though. Was just off the top of my head.

Now, that's really interesting. I have a friend who just to add to this for a second, because he he showed me something that I or he put things in a way that made me see things in a new light.

And he said I was in that grey area for a long time.

And he's like the how I realized it was I realized I was like hanging out with people I didn't want to hang out with just to consume, like to have a few beers or a few glass of wine.

Wow.

Yeah, I'm very I'm almost unreasonably averse to anything that looks like addiction. Like like even recently I had I used to always keep mints in the car and when I was driving I would have a mint. And then I one time I noticed I was like, oh my God, I'm out of mints. Oh my God, hold on.

I need to find a gas station to pull into to go get some mints because they have no mints.

I was like, whoa, whoa, whoa, hold on. What was that? Why do I think I need mints? I was like, OK, no more mints for me.

Like, so just even little tiny examples like that I am wary of.

But but the thing is with people who drink. I don't think of things as mistakes, much like, you know, your real question was what's a common mistake? So I don't know if I could call drinking alcohol a mistake.

And in fact, I actually really appreciate it when people think and act differently than me. Right. So if I think that it's wrong, that makes it even more interesting, because now I want to understand their strange perspective.

Like it's more interesting when somebody thinks differently from me.

I actually I tried living in San Francisco for a little while. I had to leave after a few months. I hated it because everybody thinks like me.

And so I'm happier living in a place like Singapore where most people don't think like me. I'm like, oh, there we go. This is much more interesting. I want to know more about people that are not like me. That's they're more interesting to me. All right.

Final question. But it's a big one. I mean, it's a big gnarly one to go is in detail now.

I don't know if you're being sarcastic or not. No, not at all.

What does it mean to live a meaningful life? I don't think life has meaning. I don't think anything has inherent meaning. I think it's all just a blank slate that we can project whatever meaning we want onto.

Like my example of walking the plank before.

And sorry if anybody wants to remind me what book that came from, you try on different meanings. And none of them are correct.

They're all just different ways of thinking of something. And then if one of them makes you take better actions, well, then congratulations. But it's nice to remember that meaning is not a fact. It's just a belief that you're wielding for now. It's just a perspective that you're choosing. So when you have people ask about the meaning of life as if, you know, it's a God, you're going to crack open and find some factual answer inside. I find it useful to remember that it's just a just a perspective.

It's just a belief that you're taking on for today. That's beautiful.

Thank you so much, sir. This was a phenomenal conversation. Thanks, Jane. You ask great questions, and I am so psyched to continue reading your book tonight.

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