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 parish and you're listening to the knowledge project this podcast and our website FS dot blog help you sharpen your mind by mastering the best what other people have already figured out. If you enjoyed 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 FS dot blog / podcast or check out the show notes for a link.
Today I'm talking with Derek severs Derek is my brother from another mother Derek started off as a musician and circus clown created cdbaby, which went on to become the largest online seller of independent. Music Derek is the philosopher king. And so thoughtful boat is 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
You of execution over ideas reading mental models 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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Derek's so great to finally get to talk to you
chené chené chené chené chené I am a super fan and super psyched to be here. There are only three podcasts. I subscribe to conversations with Tyler Seth godin's akimbo and yours.
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. No be so much better. And
then yeah, and I've been a paid member of
In Street
forever and I've just been reading your stuff forever and it's great to finally have this
conversation. I'm looking forward to it very much and 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/chappell 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
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.
Thing 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 I 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 the the interesting aspect to this for me and because you started CD Baby after that, I think most people are
Generally familiar with that story. But the first time somebody quit you were like, okay, who's your replacement?
Yeah. I still I guess when I quit that job at Warner Brothers my manager just kind of went. Oh, okay, and I just walked out, you know, did I could just you know, I basically said I quit 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. Okay, 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 about the ways of the world. Can you can you share some of those with me?
First principles thinking baby, you know it. Well, 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 right like people imitate others without questioning it enough, but I don't want to learn
Airways I don't want to be like them. So instead I just ignore it 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 go to wordpress.org and I download the zip file and I look inside and it's like what the hell you're 884 PHP files in here. There's
602 JavaScript
files in here 19 database tables. What the hell? No.
Wait, I'm going to learn all of that. I'm just I just want to put five paragraphs of text on a web page. Okay, so what's another option everybody seems to like medium.com. Let me look at medium.com pull up an article in like what the hell it was like two point five Meg's of downloads like 33 CSS JavaScript and CSS JavaScript and CSS files just to a display an article. No way that's like a thousand times bigger than it needs to be yo and to me like if I were to tell all of my reading
Readers they go to medium.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 USB stick and they mail it to you in a big box full of Styrofoam. It's like no. No, that's that's what don't that's junk. You're giving me your garbage and it's like 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.
A blank document I'll just 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 okay, so I need a home page to list the Articles, right? Okay. So we'll say add some Uli list tag to the homepage HF to the article and I'm done. So now I have to HTML files. No PHP, Nova JavaScript, no database.
And the file size is like less than 1% of the typical medium.com or WordPress blog post, right? So in the case of Wordpress like 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 of 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. I mean, so T theme stuck out to me. They're 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 you're going slower. Like you're probably took you longer to do that. Then 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 hickey is the inventor of the programming language called closure CL o j-- u re and he has a brilliant talk. That's up on YouTube.
I think if you search like simple versus easy Rich hickey, he makes his beautiful comparison about how anybody can go to their computer and type like jet. Yeah. He says gem install hairball. Like you can type one command and install WordPress on your server and he said yes that was easy, but you just did installed a big steaming pile of garbage on your server. That is
Massively complex because he defines complex as having the word root in the word complected which means to braid 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 it's simple is not always easy.
I like that a lot. I'm just trying to figure out like in my head how where to go with that. Like I'm always I think a furnham street right? Like we're always trying to reduce. I'm trying to reduce the size that people don't let him 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. Right like that's hard. Yeah it is.
That's the kind of nerd out on it. Like I really nerd out on this stuff. In fact this my little rant that 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, they don't know you're gonna 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 what like
not many people think of it that
You're too because 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 98 files were downloading like oh, yeah, I forget like this. I'm just I nerd out on
this but you do and that's what's important though. Right? Like it's something that you care about in a to what I mean you care about other people's experience with your stuff, which is really rare these days like 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 I 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 dress like have you used the product that you are getting other people to use,
you know, Innovation versus imitation for 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.
Ten seconds, but it's less fun. I'm sorry now, I'm back to the making a website not ordering wine. I wouldn't have let you find it fun to order wine for 90 minutes. But yeah, if you find the process for 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 took 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 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 Yuri, isn't it? You have this Fineman quote opening volume one of your book, right?
Yeah. I mean, we're the
Use people to fool that much is clear. But I mean, I also think that we tried it and like not consciously but we do try to to fool other people like if you think maybe Warren Buffett's a good example, right? There's the 2008 has in crisis hits and there's a whole bunch of people who imitate Warren Buffett, right? They talk like him. They go to McDonald's every morning and they eat their egg McMuffin and they say all the right things.
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 actually they're not but fed, 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 actually understands?
That's a great question.
I was hoping you have an
answer. No
Let's just leave that as 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 he'll know 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 a 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
His 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 closed and Vivid now you can see it clearly and ah, 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.
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 its 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.
Lately, 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 500 half-assed things. You know,
I think that applies to a lot of things right and it's better today. You knew be thoughtful and and tweet less than you know, just throw ideas out there and 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 instead of more. I still just say that it's just different like some people do get their best creative ideas by just reviewing out as much as possible and maybe you they spew out a thousand times more than most people but if one percent of those ideas are better than its the net better results, 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 rhubarb's 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 Rue Barth 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 that's all
and when you started implementing that was it a gradual process or like what was the
phone now? It was instant like as soon
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 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 rhubarb 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
Thing because it can be like lottery tickets. You know, like if you got nothing going on in somebody's 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 helya or no is something that should be applied to everything in life. You have to know when you're drowning an opportunity or starving for opportunity.
Is that the only criteria by which you would sort of like Gage one to use? This is like your opportunity
cost. I think so off the top of my head. Yeah
when you're running a seat.
See baby, you had to learn to delegate and you sort of like hinted in your book that we run into this like small businesses run into the ceiling. I think my friend Brent 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. Like can you expand on that? And like, how did you learn
this? So first let's okay. We'll Define it every
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 80 employees, but I was still doing everything else myself. Right? Like I was just working 7 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
King 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
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 is this is now super super super important. I'm on at the breaking point. So yeah 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 Derek you here? 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, okay been over here Tracy come. Okay. All right everybody.
He 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. Okay, 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 that 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
T' Milena over here to start a writing this in a manual I said, can you start a manual today? Like let's make this like the company manual and wrote down the answer to this one situation and the philosophy behind 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 in the QuickBooks or whatever myself even that I said, okay. This is the last thing that is still mine. So Amber 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 cdbaby like hey Dan its Derek. He's like, oh, hey man, like, how's everything going? He's like good.
You need anything? He's like no, we're all
set. Why are you calling?
Yeah, it was like, okay. 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 LA to go to film school. So I was like, all right, I'm gonna come join you so I moved down to La which I thought was like a nice symbolic show that it's like. Alright 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 4 million. Sorry.
Sorry, no Grew From 1 million to 20 million in four years. I could Grew From eight employees to 85 employees while I was away. Like just basically without me to me that was the lesson like the 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 if 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 in this is something you need. The best book on this subject is called e-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 years after I'd gone.
Gone through the process but when I read it, I was like yeah, there we go. This is the Masterpiece on this subject.
Somebody putting into words what you feel
right? Exactly.
That's a really interesting philosophy. Right? Like your you move. 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 like 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 like blow people's mind that I'd be down in ela 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 they're like dude. 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 hmm. I had to kind of tell
This tail 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 it 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 long term perspective. You have to know that it'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
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 yet. Look at the distance instead of today and know that it's going to pay off.
How do you
Think about the pairing between ideas and execution.
You know, I've got something to say about this, don't you
I do.
All right. So yeah, actually that was a funny like storytelling segue because this came from living in Los Angeles where the people I was around in ela we're all speaking in future tense, and it was always about what they were going to do.
The deals that are going to happen everything see how we're in talks with this guy at Emi and 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 man, 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 that soap. It was during that time that of good friend of mine asked me to do a favor to him to hear out his friends business idea to 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.
It's because of this situation was 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. Finally. Okay. Nice to meet you. What's this big idea? You want to tell me and he said okay, you ready? I said, yeah, I'm ready and he goes
It's online dating with music and I said uh-huh. Hey guys, dude 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, dude, you have like any implementation of the like that anything like now it's an easy is again. He's like, it's like he's telling me something profound. He's like, dude. No,
Online dating with music and then he said so here's what I'm thinking dude, my friend that 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's 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 now like what? No. No, so I think I said, all right. Look, how do I explain this?
This is 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. All 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 week idea is A1 an okay idea is a 10 and a great idea is a 20, okay, 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 $1,000. Okay, execution $100,000 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 know, okay, let's take
take great idea worth 20. No execution one dollar. Okay, that great idea was worth 20 bucks if you don't do anything about it, but on the other hand you can have like an okay idea and okay 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 it'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
Fusion that's a brilliant Insight. I had another way of coming at this exact same philosophy with different words, but it was adding too much value. So we used to work in 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 the
people making the decisions were always trying to make the ideas just a little bit better. So somebody would come to it's like, you know what I mean? Like they would come to you with a 95% idea and you'd be like, oh my God, have you thought of this this is going to move this from 95 to 95.5 and I am a genius, right? And what I noticed was that the willingness of the person to own the idea to be motivated to execute went down.
It's the quality of the idea almost inarguably when up a little bit. How much is is sort of like irrelevant? But the ability the desire of the person on the other end 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 in sight.
Did you read I think it was Marshall Goldsmith
spell? Yeah, I think that's where I actually sort of like got the words around it. But you know like yeah what got you here won't get you there.
Yes. What got you here won't get you there. Yeah. He I think the way he put it there in America. The 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 word. It wouldn't make sense if you don't have that currency no matter where you're listening. But yeah in the Americans
As 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 just zip your lips smile say sounds great go for it,
which is weird that it took me so long to hit on this myself, right? Because I mean I 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 him like that that is you know, that just lowers my desire to sort of lead this project. And then when I got on the other seat, I was like, oh now I can have my value right like and then it took me awhile and then I stopped doing it. I found this really amazing thing like everything got better people work harder. They were motivated. They own things instead of just being
Somebody who executes what they're told I mean they actually like own the project as much as you can own a project in 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 write 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 expiry. I mean
everybody probably a probably everybody listening to this because yeah, I've had this situation to like my boss told me to make this one change and it's like I do it with a Grumble now listen to 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 reading books change your life at an early age you
Awaken the giant. How did it how did that change things for you?
Yeah, Tony Robbins awaken the giant within 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
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 realized 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
Read it at a very very formative time when I was like 18 or 19 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 a maximum maximum what he calls suggestibility. So, okay. Let me try to think the the things in my life.
Velocity 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 and event as crisis or as opportunity and he makes this great example of New Orleans funerals say
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 won't that and it turns into a celebration as they dance and celebrate this person's life. He said 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 the one you can feel. So yeah, your your emotions are completely under your control.
He gives specific techniques on how to do that about questions. So he talks about asking yourself better questions. And how as the questions you ask yourself change everything like when something goes wrong, you can ask yourself. What's great about this Andy 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, okay, I'm going to follow my own lesson. What's great about this. He said nothing.
Things great about this is horrible. He said okay 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 held him. I know 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
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 Shane. It's exactly like a feather.
No, but I mean like your lens if you put something hot in it's going to stay hot. And if you put something cold in it's going to stay.
Hey, I'm imagining some kind of like sci-fi thermos. We could go like and twist something that would you like 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 with 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 know you could have just tried a hundred things, you know, the old classic example of Edison with the light bulb filament. You just getting feedback like okay that didn't work from what else he talks about how people overestimate what they can do in one year but underestimate what they can do in 10 years and yeah focus on where you want to go don't focus on what you fear and he had no 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
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 want it to be going and he said that's a great metaphor for it's like a look where you want to go. Not at what you fear God. Yeah. Sorry. I guess I have a lot of these are just like these are so ingrained in me. Like they all just feel like well, yeah, duh, that's life that's reality. But the truth is I got all of these things from that book.
That's so powerful it what makes for good writing.
You have you read it again? Actually since then
I thought okay. So I think I read it at eight when I was 18 and like again when I was 20 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, it's like okay first 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 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.
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 books 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 is 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 and I just read a book a few months ago, but 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 and how do I choose exactly?
Book, I think I probably relied 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 buck are you searching for something that you wanted to learn? Like how 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 tried whenever it's like
Reading time. I try to slow down my internal clock. Just okay 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 the 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 is 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 got to 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 words. So now I have the core of this idea in eight words and then in that text file I separate each
Each idea with two line breaks. So you know 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 parse 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,
More to them
myself talk to me about the reflecting on them later part. 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? Okay, 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 texts.
Files on my phone and if I was just sitting on the bus to get somewhere, I would just look at my folder of text files 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
Words and loading them into a database. So now if I'm thinking on a subject like 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 a hundred and seventy three ideas that came from 28 different books instantly, but just browse these ideas because again, I don't care what books they came from anymore. I just want the
a ideas so I've separated them from the book and I'm keeping them as their own little atoms to play with but then yeah the main thing I do now is to pull up all my notes on a subject like this like say he did some
And then with all of these notes in front of me, I open up my own text document to start from scratch it 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 other surrounding its 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.
Umm of my favorite paintings ever and paint my own which is not imitating there's but it's influenced by I'm kind of building on that inspired by that is that make sense? I
think so, I mean what I one of the the geeking out part of me is like, okay, 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 write about them.
Yes, so it's about internalizing it not memorizing it I used to so I'm into Anki and flashcards and spaced repetition. So I used to think huh. I wonder if I should somehow feed all of these ideas from all of these books into spaced 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
Those 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, I'd like you said at the beginning when you asked that 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 stopped 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
the directives the directives I think came from sorry everybody listening Shane's talking
about sorry. Yes something I
something that I've blogged about a few times which is
This idea of taking taking an idea and turning it into a directive which is meaning telling you to do an action. If you go to my site if you go to servers dot org, 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 Shane right now, but when I put something out into writing I like being very very very succinct. I like chopping out.
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
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 like those actions would carry that 200 pages of information.
In the actions and so therefore the succinct directives the actions, please my minimalist ruthless editor sensibilities more.
I want to talk about directives little bit more and what's interesting to me when I think about directives 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 your 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 directions.
Dev and we haven't done is the
work in spaced repetition like Anki as far as flashcards. A lot of people say you just give me somebody's deck so I can learn JavaScript or whatever but like 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 flash card is not the moment of learn Ray. So yeah, I feel the same way about the
the directives although there are different subjects in life where I want to know more about this or not. So the way actually the example that I gave about, you know, 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 environments not changing rapidly, right so that the source came up with these in a certain environment and you just have to make sure that that environment still exists because if it changes rapidly than 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 2029?
Let's do a deep dive on tractors. Why don't 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 in a knowable
world. This is like this is like your talk show host and you say hey, why don't you perform one of your songs for us? Sure. I'll be quiet. No, really? I don't mind. All right. Hold on. Let me pull up we all like the ante.
A fragile
concept it's particularly accurate No 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 booknotes lots of paragraphs and kind of condensed them down into these. What is it six directives one prepare for the worst, since you have no idea what the future may bring be open to the
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 number 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
Anytime 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 Corporation or your past public statements be an absolute opportunist doing whatever's 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 6 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 2012.
D in the middle of quarantine and all that like went back and read it just kind of smiling and nodding like yep prepare for the worst expect disaster. Yep,
dude. This is like gold. I just want to sit here and listen to you. Like keep going on this Dev. What are the other? What are the ones that
stand among her? We gotta do the Monger one you and I are both. Hey, actually Shane. Have you heard of Charlie Munger? I think you would
Begley. I mean, I think I remember coming across him in a headline somewhere.
So you and I are
both Monger fans. So I'll just do this one more that is totally a not a ripoff. But Charlie munger's ID. 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 descriptions are misery guaranteed prescriptions for misery.
How did you just happen to know that guarantee? Ya thank you. That was it and I just I loved that format. And so
I
tried my own version of that which was how to stop being rich and happy number one prioritize 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 written. Happy number to Chase that comparison moment.
And 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 by not rent. Why rent a house a castle a boat or a car when you can buy it.
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 5 how to stop being raped and happy be a connoisseur. Learn. What others
I'd say is the finest insist on only the finest you will now be unhappy with anything. But the finest number 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 in your heated Floor Just Right work out the whole solar panel charging of your Tesla car. This is important.
And lastly number 7 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 need I hope I hope that email me and
tell me to do that and keep annoying me until I do it. I
will I'll just you know, what I'll do is I'll just cry because I can program I'll just create a script to eat.
You every five minutes. I'm curious like how you go about making important
decisions. Well, 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 blind spots. It was like right there in the first few pages and he said about blind spots and I think
Okay, 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 then searching for reality because you heard maybe the common thread in there is it's about looking for a perspective that helps me write 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 backyard, 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 to check there you are.
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 is going to kill you in 3 seconds. If you don't walk across that plank now.
Is that get you to walk across the plank? Okay. 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 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 pith hat right going off into darkest Peru to places that no one has explored. Well, I
Doing that with perspectives. I often think of any random thing and I think we'll 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 I 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 15 formative years like from the age of 14 until 29. All I wanted from life was to be a successful musician. And so I think now I still approach life like I
Coach to music with lots of young. 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 cure. I have a have at all times handy some of my favorite Brian Eno quotes. I love
these quotes so much not just Brian Eno's but like from a collection of musicians that whose ideas inspire me. I ended up making a little website called music thoughts.com 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. Okay, 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. Here's a favorite one cut a vital connection find what's holding everything together than 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 quote unquote here.
During all the stuff around it too. Okay. So I've got like a thousand of these on this website called music thoughts.com and I think I forget that I'm still taking like this experimental musical approach to life. So when you asked how I make decisions, I think it's very similar to like Brian Eno making musical decisions in the recording studio like hmm. This approach sounds fun. Let's try this.
I like that a lot. I want to
Back to something you said at the beginning of this which was whatever compels you to take action. But how do you how do you decide what actions to take in this in this situation?
Hmm. I don't know. I think that's just one of those every situations different. I think you just sometimes you have a concrete goal. Right? Like I need to exercise more right what philosophy what mindset going to
help will help me?
Yeah, right, but other times
As you just don't really know what to do. All right, I'm going to give a concrete example from my life. This is kind of personal but after I sold CD 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
Sing 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 complete just set off.
Of 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 cdbaby. And so I've been wanting to avoid all responsibility for the rest of my life by doing that. I'm going to die. 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 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 what I sort of like internalised a little bit was like it's not that the tactic it's the direction. So you knew where you wanted to go not necessarily how to get the I mean you've lived
it. No, I didn't.
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 change 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 knew.
Oh, yeah, and then making a plan kind of relatively is the easy part once you know where you're going once you like pick a place on the map and say
I want to go there. It's like all right, we'll just that's Northeast of here. Let's head north east and you of course, you're gonna adjust along the way to continue to use our Explorer with the pith happen.
If I don't know, if a lot of people think that way I mean, I don't think that's maybe as common as or 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? And how did you recover from
that did I did I the biggest mistake is the only one that I can say like a really objectively they had that was a big huge mistake.
Jake was carelessly wrecking what could have been a great romantic relationship. So yeah, sorry Ray, um, 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 okay talking about it what happened? We should not do it 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 sky like some bug is something in my head that like 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. Just tell her sorry and get on the next plane out. And and I went yeah, I guess you're right and 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 gonna get out of here on a plane today. We're done.
She was devastated and and I called the left and so a couple epilogues to this that actually make the story. Is that a couple months later that same friend that gave me advice on what to do in that moment was doing some reading about real 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 tell me like what that means and I was like
My God, I have those Tendencies to and I thought man. I really called the wrong person that night like I was in such an in a suggestible influenceable 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 in
Dead I randomly called the other friend. In fact, I actually tried to call three or four different friends in the one that I talk to is just the one that happened to answer the phone just by chance a 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 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 how 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 he 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 cried 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 if we continue 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
mean? I don't know exactly here. Let me Google that for you. I don't know. Um, 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 light-hearted. 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 30s and then 10 years later. They made Before Sunset I think in 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 20 years earlier and what they did in that first movie 20 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, okay see you here in a year and then they departed and so now 20 years later in the third movie there going God. Why did we do that? Like what were we thinking like why not?
Trade phone numbers and one of them said I know I we did that is because when you're in your 20s, you think that these amazing loves will just come all the time you think oh, there's another 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. He 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 what's funny is after that all happened and I told some friends about my deep regret different friends than the love of avoidant trend all of my friends do the thing that friends do to each other is they say
Like I'll do it. It's all right, you know, I'm sure you know, it's for the best. I'm not sure something inside you probably knew that this wouldn't have worked out anyway, like 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 as like, oh, it's for the better. Anyway, no.
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 now?
No, she's amazing. She's like the most forgiving wonderful. I don't know how she did her heart is ginormous. It's amazing. So no, we're just were
awesome. That's awesome. What's here your
compass who?
Huh, 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 deepest Peru. Anyway explorers. Don't go in a straight line very much. We're exploring so I often focus on
Aspect of my life that's lacking and then I'll enhance it until maybe it's almost overflowing and then I had turned 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
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
National 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 likes it. So James Clear wrote this masterpiece, if 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 get dressed 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 a little and that is amazing and admirable and I'm sure there is 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 away that comes it's going to say comes easiest to us, but
Be 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 super charged right because that's just our nature, you know, cheetahs can also swim but at often 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 this 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 cdbaby. I did one thing for 10 years and then at a certain point, I think okay. I'm done now, I'll do something else but I
obsess that's beautiful. I love that bit. I wanted to make a point before we went back to habits. But which was sort of like working with the world versus working against the world right? And that the way that you sort of mentioned that made me think of that.
You know look up a quote by Joseph taught us men and it's is so indicative of this is 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 Tailwind versus head wits.
All right. Nice one. Yeah. Thanks for pulling up that quote and
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 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 wins and Tailwinds and nature and just calling it The World instead of calling it your nature like
Is your reality we're all experiencing our own reality and in my worry ality. Yeah diving into one thing at a time is the way that the world rewards me. I think
that word should is really interesting. Right? Like I 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 okay shooting all over it.
It's okay. So yeah. Well, I mean look, I love changing my mind. I love having my mind change. I love changing. So yeah when I'm reading a topic Atomic habits, for example, I'm sitting there going. Yeah. Yeah. This is the way to live right on. Yes in that moment. Yes. I want to be like that. There have been many ways. Obviously. Look we're all walking instead of crawling right? We've all learned.
Ooh, 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 that you know, this is just my nature. This is how I am but then it 56 you can be very different you could have taken on some new skills and it maybe it was gradual, but you can be a very different person that you used to.
Be so yeah, we can all construct who we are. I
think speaking of who we are. Do you have foundational values?
Mmm, at least probably change on situation. But yeah change on situation to based on situation like a few months ago again here. We are in April 20-21 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 on living in England right now. I moved here so that I could travel my
Assaf 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 Shane number one cultural exploration travel and yeah, here we are in a quarantine which I was sad about for a minute and then I had to just question that like, okay really, is that the only way I'm going to learn about
Our culture's is to get on a plane and go there and walk around like where 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 may be watching the top five most popular movies in turkey and maybe scheduling phone conversations with 20 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 alright my values of 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 are friends with because they live next to her but 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 friend. 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 yeah, what's invariant?
Invariant who 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 or 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 are those don't change.
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 5:30 a.m. Before I feel like getting out of bed thoughts. Is it 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 like just open up my journal. In fact, I have a recurring journal on this subject I have
A journals that I called them topic journals or 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 dot txt. What would I do if I had a hundred million dollars and I 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 asked really hard. I really tried but every time the answer is basically nothing like if you were to give me a hundred 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
They
had to you know, attend events or whatever because you know wearing a tuxedo to attend this event now that I have been given the Nobel Prize like I don't want a Nobel Prize because it 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 problem. It's true.
How did you become a minimalist like where does that come from? Were 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 the people but then they can still go by that desirable thing. I think it's only when you felt the pain.
In 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 like every time I unpack this stuff? What is it for? Why do I have all this stuff? Yeah, then it
Is an accident of Fate that I moved to I moved to Portland Oregon wall CD Baby was in full swing like it was just taking off what 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
Cause you didn't need all this
stuff this stuff state in storage for six years until finally six years later. I just as a present to my employees and like okay 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, just gave away everything. I owned the last thing that I had to that nobody wanted to take of course where my Diaries I used to have like 20 or 30 big notebooks that were my Diaries ever since I was a teenager.
And I looked at them and I was like, yeah my Really Gonna lug this around for the rest of my life. Like just threw me in the dumpster
if your house was burning what would you grab my kid?
Hey, that was easy.
Okay, what what nonliving thing regime
Turtles living? Yeah, I guess
I knew you were gonna say her kid that I was like it's phrase that
wrong actually.
Yeah, I have a real answer. I have all of my passports and yes, it's plural in a little ziplock bag for that specific purpose. It's like actually Kia all of my like debit.
Are there a spy or
you know, I mean, I've just you know, we could it's just different subject. It's you know, I left America 10 years on my Explorer Mission, you know and see I've I have five different drivers licenses from five different countries and I have like four different resident ID.
Key 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 is your son now 8
that's a great age man. Like that is such a fun
time. Yeah. Oh they've all been fun times. It's funny. I did that to a somebody once I was like when my kid was for I talked to a dad who's 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 man, we always say that like no the time you're at it's always the best time.
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 there are other diapers and then when they're out of diapers,
Like I can't wait until they go to school right? Like at 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 till the next phase. Wow, they tend to be like that across the board. Right? Like 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 Ya
to me. I 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'd just happened to meet her when she was going through a really hard time. But the I knew her for years and years and years and years and years and no she is always going through a hard time right now. It's just a way of seeing the world.
It seems yeah people I mean,
Is 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's like, oh, you know, I just can't wait till there are two type row 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. I don't you drink. Is it 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 moment, 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 gray area between them. So I think the mentality that says it's hey, do you know any time you get together with friends? Of course you need alcohol and hey, I'm having friends over get the wine. I think that that blurs kind of quickly into like well we need the well, we're having friends over we need wine, you know wish that at that point becomes like something a little close to addiction, but I don't know. That was sorry. I don't have profound thoughts on this those just off the top of my head.
You know, that's really interesting. I have a friend who just add to this for a second because 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 gray 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 class. So on.
Wow, yeah. I'm ver 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 compile into to go get some mints because I have no mins. I was like whoa! Whoa, hold on. What was that? Why do I think I need men so like, okay no more mins for me. So just even little tiny examples like that. I am weary 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. 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 right. 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 on like, ah, there we go. This is much more interesting. I want to know more about people that are not like me that's their 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. And now I don't know if you're being sarcastic or not. No. No, 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 on to like my example of walking the plank before
Sorry, if anybody wants to remind me what book that came from you try on different meanings and none of them are correct you 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.
If that you're choosing so when people ask about the meaning of life as if you know, it's a geode you're going to crack open and find some factual answer inside. I'd 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 Sarah. This was a phenomenal conversation. Thanks Shane.
You ask great questions, and I am so psyched to continue reading your book tonight.
Hey one more thing before we say goodbye. The knowledge project is produced by the team at Farnam Street. I want to make this the best podcast you listen to and I'd love to get your feedback. If you have comments ideas for future shows or topics or just feedback in general. You can email me at Shane @f s dot blog or follow me on Twitter at Shane a parish. You can learn more about the show and find past episodes at f-- s dot blog /
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