The Exchanges

Q because I mean, I know of you, I read your stuff, and then going a little deeper behind the scenes is, is always fun, and I found this really interesting story. You worked as a librarian at the Warner Chapel Music, And you quit. And that is like one of the most interesting stories I have ever seen, um, with somebody quitting. Can you, can you share that with me?

A Sure. Uh, it was my first real job. It was at Warner Brothers in Midtown Manhattan, the music publishing division. Uh, it was an office with about 14 employees, and I was 22 years old, and I had been working there for two years, just the bottom entry-level position running the music library. But I loved the job, and I loved my colleagues, but after two years, I was ready to quit so I could be a full-time musician. Like, I was earning enough on the side as a musician that I could quit. So I found someone to replace me. Um, 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. Uh, she stayed at my place for a while. I trained her, and I taught her everything, and after a week or two of that, uh, 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.

AI assessment note: “that's when I told my boss that I have to quit now, but here's my replacement.”

Q There's definitely some benefits to being naive about the ways of the world. Can you, can you share some of those with me?

A First principles thinking, baby. You know it will. I honestly didn't even know it was called that until Reading your site. Uh, 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 their ways. 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, uh, 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? There are 884 PHP files in here. There's 602 JavaScript files in here. 19 database tables? What the hell? No way I'm going to learn all of that. I'm just, I just want to put five paragraphs of text on a webpage. Okay, so what's another option? Everybo…

AI assessment note: “this approach is more creative, right? It's more inventing instead of imitating”

Q How did you become a minimalist? Like, where does that come from? Were you always that way?

A Uh, no. It's because I moved house a few times. And I think, uh, like I said earlier with, uh, my, my woe is me story of the relationship, I think you learn best by feeling the pain. Uh, so you can preach minimalism to people, but then they can still go by that desirable thing. I think it's only, uh, When you've felt the pain from having too much stuff that you finally get it, right? So I used to have too much stuff, and I moved house like three or four times, and every single time I'd load up the big U-Haul van full of my stuff, and then get to the new place and unload the stuff, and, and, you know, the first time it was annoying, the second time it was really annoying, the third time I was like, oh my god, why do I have, like, Every time I unpack this stuff, what is it for? Why do I have all this stuff? Yeah, then it was an accident of fate that I moved to, uh, I moved to Portland, Oregon while CD Baby was in full swing. Like, it was just taking off when I moved from the little village of Woodstock, New York, out to Portland, Oregon. And because I was just so damn busy with work, I put all of my stuff into storage temporarily. Meaning it to be like for a few weeks until I could find a home. But then I ended up living at my grandma's house.

AI assessment note: “Uh, no. It's because I moved house a few times.”

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

A Oh, no, it was instant. Like, as soon as, 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, 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 Rhubarth, who's a songwriter, just kind of gave me that nicer, simpler mantra. Um, 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, and everybody was throwing everything my way and everybody wanted everything from me. So It was a good time to raise the bar all the way, but strategically, there are other times in your career when really the most strategic thing to do is to say yes to everything because it can be like lottery tickets, you know, like if you got nothing going on and somebody's offering you an infinite amount of lottery tickets for free, well, then how many do you want? You know, I'll take all of them, please. So I don't think that hell yeah or no is something that should be applied to every…

AI assessment note: “Oh, no, it was instant... I just started using that for everything instantly.”

Q Do you read it cover to cover? Like when you pick up a book, are you searching for something that you wanted to learn? Like how, what's your process for Picking up a book and then reading it.

A Yeah, I don't skim. I know that some, I know a lot of people skim, but I, no, I try, 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. Um, unless a book really sucks. Unless it's like I'm A third of the way through, I'm like, yeah, I don't like any of this. Then I'll trash it. But for the most part, I hear them out. I go start to finish. And most importantly, which we can really nerd out on if you want, 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 kind of put them into my own words. I remove They're unnecessary words. I think I'm more of a harsh editor than most people. So yeah, I chop every unnecessary word. So now I have the core of this idea in eight words. And then in that text file, I separate each idea with two line breaks. So, you know, idea is on one line or maybe two or three lines, but whatever it is, I hit enter twice to leave, uh, 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 …

AI assessment note: “I don't skim... I try to read just start to finish.”

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

A Sure. Um, 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, uh, here's the problem. We tend to say yes to whatever we can. We like to stay busy. So when faced with the decision to do something, we ask, can I do that? And if yes, then we often say yes. Maybe it's the fear of missing out. Maybe it's optimism. Maybe it's because time is like distance where we can't see far away so clearly. So we mistakenly think that we'll have more free time in the future, but then today comes and now it's all close and vivid. Now you can see it clearly and 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, is to raise the bar all the way to the top. Say no to almost everything, and leave space in your life. Leave free time. But this is not relaxing, it's strategic. Because then when something great comes along, like something that makes you say, oh, hell yeah, that would be awesome. Then not only can you say yes to that, but now you have the time and energy to throw yourself into it completely. Like now you can give it your all, you know, the baseball m…

AI assessment note: “here's the solution, is to raise the bar all the way to the top.”

Q Um, That's a really interesting philosophy, right? Like you're, 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.

A I think only that one week that I described like calling the office and being almost like a little sad that, uh, 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 LA and meeting up with somebody and especially somebody else who was still in that trap, right? They're like, oh my God, I can't, I 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, mm hmm. And I had to kind of tell him this tale. Like I, it was hard work, but I delegated everything and it just, I had to, I was really at that breaking point where I was ready to walk away if I didn't. So.

AI assessment note: “I think only that one week that I described like calling the office”

Q I think that word should is really interesting, right? Like, 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.

A Like, uh, I'll do one more Tony Robbins quote. He calls that shooting all over it. Uh, okay. So yeah, well, I mean, look, I love, uh, Changing my mind. I love having my mind change. I love changing. So yeah, when I'm reading 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, we're, we're all walking instead of crawling, right? We've all learned to, we've all changed in our lives, and so there are some ways that You might have said when you were 16, hey, this is just the way I am. I'm always going to be this way. But then at 36, uh, you are very different than you were at 16, and no, it's, it turned out not to be true. So I'd like to think that that can keep happening. So even at the age of 36, you could say, you know, this is just my nature. This is how I am. But then at 56, you can be very different. You could have taken on some new skills, and maybe it was gradual, but you can be a very different person than you used to be. So yeah, we can all Construct who we are, I think.

AI assessment note: “In that moment, yes, I want to be like that.”

Q I think that applies to a lot of things, right? And it's better to, you know, be thoughtful and, and tweet less than, you know, just throw ideas out there. And, um, how did you come up with this? Was this like an overnight thing or?

A Yeah, I totally, also, I have to say one thing, what you just said, like, it's better to tweet less instead of more. I'd still just say that it's just different. Like some people do get their best creative ideas by just spewing out as much as possible, and maybe they spew out a thousand times more than most people, but if one percent of those ideas are better, then it's the net better result. So I don't want to say like this is the best approach to take for all things. That's why I say it's just one little monkey wrench. I think it's a tool to use When you're overwhelmed and almost drowning in opportunities, and therefore you don't have the time to give your full attention to any of them. As for how it came about, it was just a situation where I was telling my musician friend Amber Rhubarth 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 Rhubarth 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, I changed the word to hell to soften it a bit, and, uh, the idea caught on, and that's all.

AI assessment note: “As for how it came about, it was just a situation where I was telling”

Q From episode number 88, Derek Sivers. And is that where you come up with your directives?

A Oh, the directives. Um, the directives, I think, came from Sorry, uh, everybody listening, um, Shane's talking about something I've, something that I've blogged about a few times, which is this idea of taking, um, taking an idea and turning it into a, a directive, which is meaning, uh, telling you to do an action. If you go to my site, if you go to Sivers.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 every possible word, leaving only the words that need to be there. So I noticed that as I was learning about certain things, I felt like most books use way too many words, and I came to this idea that probably the most succinct way to communicate an idea is to focus on the action itself. Like, if you command the action, then the action, like a seed, I think there's like a nature metaphor in here somewhere, that the, the action has the seed of the idea in it, that the action carries the idea along with it. You can talk for 400 pages about Calories and, uh, 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 20…

AI assessment note: “the succinct directives, the actions, please my minimalist, ruthless editor sensibilities more.”

Q That's so powerful. What, what makes for good writing for you? Have you read it again, actually, since then?

A I, 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 and the sky is blue. It's like, yeah, yeah, yeah, yeah. I was like, ok, this stuff is just too ingrained in me. I just, I don't, sorry, I can't read it again. It's just, it's all just obvious now.

AI assessment note: “I think I read it at eight, when I was 18, and like, again”

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

A Hmm, I don't know. I think that's just one of those, every situation's different. I think you just, sometimes you have a concrete goal, right? Like, I need to exercise more. What philosophy, what mindset will help me? Right. But other times you just don't really know what to do. All right, I'm going to give a concrete example from my life. 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 reading something, and what it was doesn't matter, because it was just a random story about Benjamin Disraeli or something, but there was a sentence in there that made me go, oh my god, I know what I want to do. And it was just talking about how Benjamin Disraeli never shied away from the spotlight, that he, he courted attention And took on the extra responsibilities of courting attention. And that tiny idea, to me, just like, it just set off a bunch of other things in my head, like, oh my god, I've been running from responsibility, because I didn't like having 85 employees at CD Baby, and so I've been wanting to avoid all responsibility for the rest of my life, but by doing that, I'm, I'm turning invisible, I was consider…

AI assessment note: “I'm going to give a concrete example from my life.”

Q How do you filter what you read now?

A It's usually either to solve a current problem in my life, like say if I'm, I'm having issues with parenting, or Having issues with keeping up with my habits or, or even, like, a knowledge problem, like, I don't know who those old philosophers are. People keep talking about Nietzsche. I don't know anything about Nietzsche. So I'll, like, go read a book to solve that problem. I often read just because I think that this book's insights could help my life right now, even if it's not a concrete problem. But, like, whenever I read anything by Mark Manson or Steven Pressfield, I always come away feeling like, Yeah, that's a really cool insight. Like, it wasn't to solve a concrete problem. I just, I like their philosophies. And then often it's just for curiosity. Like, I just two days ago finished a big long course on linguistics, and that was a blast. John McWhorter, The History of Language, uh, was fascinating. I love reading about geography. I love reading about the culture of different countries. Yeah, I just read a book a few months ago about the culture of Finland. And just found it fascinating. So, uh, yeah. How do I filter though? Knowing that what I'm looking for is what I just described, then how do I choose exactly what book? I think I probably rely too much on Amazon reviews, or just if there's a wise person that I like, that I'm a fan of them, and they say that, you know,…

AI assessment note: “I think I probably rely too much on Amazon reviews, or just if there's a wise person”