Derek Sivers: No Wasted Words

My number one bit of advice about writing a book, don't think of it as a book. Put one idea at a time out into the world. And how does that help you write? Like, like, where does this show up in your writing process? What's going on? Get individual ideas online. Get them out into the world. Let them breathe. Then the world can give you some feedback on them. You can test them out. You can see where you might have been thinking about it wrong.

What I love about talking to you and reading your work is you're always making me question, why am I like that? Why do I believe that? There we go. Like, that's the ultimate reward. What is your process for becoming a master writer? I don't think I've ever talked about this publicly. Derek, welcome to the podcast. I've been a fan of your work for the better half of a decade now. I recently learned that you were writing a post-humus biography.

What are you learning about that? Talk about that. Okay. Well, it was inspired initially by one of my best friends, Milt Olin, who was just one of the wisest, smartest people I'd ever met. Every time you'd have a conversation with this guy, you'd come away just with your perception of life changed. I'd always go home and take notes after we talked. We'd have these great conversations over restaurants for hours. And then he died.

He was hit and killed on his bicycle by a police car, weirdly enough, steered into the bicycle lane. And he was killed, but the problem is that Milt never wrote down anything. And I was so sad after he died that devastated to lose my friend, but also double devastated that all of that wisdom he had was only ever going to be shared with the people that he had conversations with, not written down. And so I already liked writing what I'd learned to share with others, but that really emphasized it, right?

Like that really brought out this idea of writing lasting after death. My grandfather was not someone who I got to know super well. And now that I've become more interested in ideas, I was just working out, thinking about this, be like, oh my goodness, my grandfather understood the human condition. And yet, because there isn't that much writing that he did, those thoughts, those ideas, those memories are lost the time.

Yeah, I've been thinking about this idea of the personality. So imagine this, that everything you've ever learned, the culmination of everything you've ever realized or learned or taken in or experienced, it gets filtered so that you adopt the traits that meant the most to you or stuck. In your persona for some reason. And then when you share your personality with somebody, even let's like put writing aside for a second.

Let's say my friend Milt Olin, his personality lives inside me now. Like I can often imagine what would Milt say. In fact, I wrote this little article, uh, s-i-v-e dot r-s slash m-e-n-t, the first four letters of mentor. So s-i-v-e slash meant as I wrote this article about how I communicate with my mentors. So I say, I do this and I do that and I do this and I do that. And I ask myself what my mentor would say. And I do all this before I contact them.

And in the end, I often never contact them because I just needed this thought process of what would this person say. So Milt Olin was definitely one of my mentors. And I, and he still is that often when I'm in a situation, I wonder or ask myself, what would Milt say? And his personality lives on inside of me, right? So this is a wonderful motivation to write down everything you've learned or even just share your point of view on something.

Because just sharing your point of view, even if it doesn't seem that impressive or breathtaking, you're sharing yourself. And who you are is the culmination of everything you've ever learned, filtered through the things that you've chosen to adopt. And that's what we call our personality is the things that, like the traits that we've adopted. So just sharing that with the world is filtering the past for the future. You know, one of the things that I've always so admired about you, and you see it in, in, in How to Live, your new book, is your ability to distill, to compress, and you did an experiment where you said, I'm going to write every day for a month.

And then you said, I don't like that. How do you think about the balance between those two? Thanks for calling me out on that. I am not sharing enough lately. The past couple of years, I've just had my head down too much in other things. I also admire Seth Godin, like you do too, and I know that your interview with him was cold writing every day, because that's like the main takeaway I got from him too. He, he says it over and over again.

It's the most important thing he's ever done, is choosing to write every day, no matter what. And so, yeah, I was trying to channel my other hero, Seth Godin, when I tried writing an article every day. But I think the difference for me was, I wanted to raise the bar a bit, so that when I tell my

subscribers, my fans, my listeners, whatever you want to call them, when I tell them, hey, I've posted something new, I want it to be something worthy of their time. Whereas I think that a lot of the things that I, when I was posting every single day, I didn't find it quite worthy. What's funny is that somebody else from the outside once looked, who knows my writing very well and knows all of my posts, actually felt that the stuff I posted during those 30 days was of no lesser quality than anything else I've ever posted.

So maybe I'm just completely wrong, I'm an idiot, and I should just post it all and not try to pre-judge, pre-filter for the world. But I just, I feel better if I raise the bar a bit. And I think probably the sweet spot for me would be like posting once a week or twice a week or something like that, where I'm writing every single day, having ideas every day, but just the ones that feel like, damn, that is so worth sharing.

Then you put those out once or twice a week. You know what I struggle with is, a lot of times are my more polished pieces. I lose that fire that you can only get right after an epiphany. There's a childish excitement right after you have an epiphany and you run to the page, you write it down. And now I'm not saying that the things that I instantly come up with are the best, but I do think that as a writer, one of the things that I can improve on is keeping that excitement on pieces that I have worked on for a long time.

It's almost like there's a level of writing that's actually too polished. And I wonder if I run into that sometimes. Hey, you just finished reading my How to Live book, or at least some of it. Did you think that was too polished? It's careful. It's intentionally careful. The frame of How to Live is a very careful text. And I think that you set that out at the very beginning. I think that you say something like, read slowly one line at a time or something.

How will the reader, from the very beginning, this is a polished piece of work? For example, take the piece about Santa Monica beach running, okay? Where you basically say, you go as fast as you can. It took 34 minutes or something. And then you slowed down and took you 38. That story is an epiphany that you had that you likely then went to the page. And there's a freshness about that piece that isn't in How to Live.

But at the same time, I think that they're different contexts. Yeah, that's a really good point. I like that, the excitement. The childlike excitement you have of a new idea you're bursting to share. I think we always fear that we don't want to be like the stoner that gets really high. It says, do you ever look at your hand? And the problem with this idea of people connecting drugs with creativity is that the drugs make things seem more interesting to you.

But then the ideas that you put out on drugs are often then less interesting to others because you found them too interesting at the time. And so others don't think it's so interesting to look at your hand. That's not a big idea, but it was fascinating to you at the time. See, I think it's funny. So I sometimes wonder if the moment I have a big epiphany, am I temporarily high with this idea? Well, one of the things that you've said is that when listening to a piece of music, that you're usually too analytical.

So we could almost transport this same conversation into music. So does the same thing happen when you read or what are you feeling? Okay, I'm curious if you have this too. When you've studied the craft of something so deeply, then you see details that most people don't see or hear in the case of music. So yeah, when I'm listening to music, sometimes I nerd out on like the recording engineering of how they did the high hat or they put a certain effect on the echo.

And I'm like, oh, listen to that. And anybody else listening just says, what? It's just a cheesy song, stupid lyrics. I'm like, shut up, listen to that echo, listen to that reverb. And it could be the same thing with writing. I shall do another musical comparison that there are a lot of songs that I like, even though it actually might be a bad song. But damn, it's got one really interesting chord. Like it goes to this one really unexpected place there.

I'm like, ooh, so I love it for that. I even found this with films. Sometimes I would nerd out on cinematography. And I'll give you an example of a bad movie that had interesting editing, for example, was Oliver Stone's movie, Natural Born Killers. So many people hate this movie. My friends hated the movie. But I just watched it again and again because I found the editing fascinating that they would often take a scene and break it into a different point of view and suddenly throw an effect on it and like show it again.

And it's just like, I just thought the editing was fascinating. So I watched the movie again and again, but I was really watching the editing. I didn't really care about the message or the meta point, you know, who cares? Actually, this is a great analogy. So here's where I've done some film stuff. And I've made, you know, movie or not movies. I called them movies at the time, but I made like YouTube blogs and stuff.

And I've, then when I was in college, I do college television. And what I found was after I would edit for a while, I couldn't actually see it anymore. I don't know if you've worked on design projects. I don't know if you've worked on film projects. You can't see what you've made. And what happens is because you've spent so much time with it, you become impatient. And what you think is the right speed is too fast for what the listener needs.

Brian Eno, the father of ambient music, had a heuristic. He would finish an ambient song and automatically take every part of it and double the length. And then he'd say, that is now what I'm going to ship. Interesting. You know, you and I have studied the craft of writing so deeply. And the problem is, yeah, when I read almost anything by almost anyone, I almost always feel it could be done better. Like almost every sentence could be improved.

I just, I can't help but look at things like an editor and I have to try to turn that off and get to the real point of what someone's saying. Because we have to separate the details and the point, right? Like the example I used earlier of the certain effect on the echo and the music. That's the details. I shouldn't miss the point of the song or I shouldn't think that if I put a cool effect on the echo, that I've made a great song if it's a bad song.

So it's the same thing with writing that sometimes say in poetry, for example, we appreciate a certain combination of words. Like we really love these three words together. And we go, ooh, that's so beautiful. But the idea underlying it might be, you know, banal. But we just love those words. So it can be the same with our writing that if we nerd out on the craft too much, we could end up saying something not impressive because we're showing our craft or we're too fascinated with our craft.

So yeah, it's distracting. Yeah, for sure. I mean, I think David Foster Wallace fell prey to this. He was so obsessed with the craft of writing that I think it often hurt his own writing. And so for me, what I find is I talk to other people. But I would love to hear this for you. Like, do you don't really hang out with people? So do you? How does this decision fuel your writing? Does it help? Does it hurt? Yeah, my situation's not ideal.

I live in New Zealand and I moved here because it's a great place to raise a kid. So I moved, I was living in Singapore when my kid was born and moved to New Zealand so that he could grow up in paradise. After like flying from Singapore to New Zealand, I looked back at my calendar of people I'd met. I met up with 490 people one-on-one in the two years I lived there. I had 490, like coffees basically, 490 conversations.

And I was so social and I overdid it. So moving to New Zealand was mostly for my kid, but also it was a time for me to just like put my head down, do my work instead of just being so hyper-social. But yeah, I've noticed that I miss out on the ideas. I got a caveat coming to that in a minute. Because yeah, most of my favorite ideas have come from this two-way banter in a conversation with somebody where first something they bring up sparks a reaction in you and you say, huh, I wonder if this and then either they can show just disinterest like, yeah, that's not interesting.

Or luckily they can push back. They can say like, no, I think that's not true because such as such. And you go, ah, you're right. That isn't true. I was thinking of it wrong. Or the best is when in a conversation you say, huh, do you think it might be this? And they go, oh my god, that's so true. I've never thought about that. And you go, oh, you know, mental note, like a like a comedian testing out new material. Um, you think, okay, cool, that one worked, that resonated.

Um, and so those are the things that I would turn into future articles is often things that my friends found amazing in conversation. Or I should say not just friends, but like people found interesting in conversation. Um, the caveat I was going to say though is the phone works just as well for me. I have wonderful conversations with friends around the world. So when you heard somewhere, I guess I must have said somewhere that I don't hang out with people.

Um, that's just a side effect of my remote location in the middle of the Pacific Ocean here. Um, but I do have great conversations on the phone with friends. And that's still where some of my favorite ideas come from. There was one thing to get super meta about this. There was one thing that I think you missed. Um, and it's this line from John O'Donohue. He's an Irish poet. I don't know if you're familiar with him, but I think you'd really like his work.

And he asks, when was the last time you had a great conversation? A conversation that wasn't just two intersecting monologues, but when you overheard yourself saying things you never knew you knew, that you heard yourself receiving from somebody words that found places within you that you thought you had lost. And he goes on to basically talk about how most conversations are a game of ping-pong, hit, receive, hit, receive, but that a good conversation actually elevates both people onto a new plane of thought.

And both of them are experiencing something that they could not get to on their own. And he says that conversations like that are food and drink for the soul. And I say this because I think that this is the other thing that a conversation can do is it's two people dancing in tandem, ending up somewhere that they wouldn't have come up with on their own. And it's in that partnership, I think, that we often come up with new ideas when you get, oh, yes, oh, I didn't think about that.

Hey, have you thought of this? And there's a support that is inside of that. There's a famous little itty-bitty blog post I had called Hell Yeah or No, of course. And the thing is, I try to tell anybody who will listen that that idea, the core of it, actually came from my musician friend Amber Rubarth, who's a brilliant musician. And it was when I was on the phone with her and talking about like, I'm supposed to go to this conference in Australia, but I really don't want to.

And I was like talking about it. I was like, you know, I just feel that we just need to like raise the bar all the way up. So that we just say no to almost everything and only say yes to the things that were really just like, yeah, like super excited about. And then she's the one that said, so what you're trying to say is, it's like not a decision between yes and no. It's a decision between fuck yeah or no. And I laughed.

I was like, yeah, that's it. It's like a decision between fuck yeah or no. And, you know, then I wrote the article that night and at first the original version was longer and I gave her credit and I changed the word to hell. And then when Penguin published it in this book by Seth Godin, you know, they edited it down to just like 10 sentences, which I was okay with. But yeah, it was fully a conversation like both of us bouncing off each other.

And it's great. Amber Rubarth and I still have these great conversations like every week or two. She's amazing. I don't know why I missed your quote today. I'm not usually like this, but I'm feeling it right now, Derek. And there's a line from Tom Stoppard who says laughter is the sound of comprehension. And I think that that's what happened in your conversation with Amber is she says that you laugh and actually if you deconstruct what's going on is laughter is your body telling you that you have a very compressed unit of knowledge that has deconstructed your world view and reconstructed it in a way that's better in an instant.

Have you interviewed a stand-up comedian? No, but I got to do it. Yeah, stand-up comedians are I think they're still underrated and I think that that's comedy. Yeah, it's it's like philosophy. It's like it's I think like Louis C.K. I think is a philosopher. I love the insights of a great stand-up comic, the good ones. Yeah. Well, it's funny. I was talking to one of my best friends is philosopher and I was talking to him on the phone last night and he said that most of philosophers that he's learned with take the enchanted and make it mundane and then what a comedian does is they take the mundane and make it enchanted and I thought that was a beautiful way to put it.

What a comedian does what Louis C.K. will do so well is he'll take him getting the kids ready for school and it'll be this super mundane thing that he's just doing and he'll spin it into a story. He'll sort of rile it up and by enchanted I don't mean the magical sense of enchanted but it's adding a scaffolding to it that makes it hilarious that makes it ring in your mind afterwards and what a comedian would so often they do I think Larry David's the absolute master of this is like Larry David has this great skin about the chat and cut where like there's a bunch of people in line and rather than waiting in the back of the line you go up to person number eight in line and you say Derek haven't seen you in a while and it's totally bogus like you've met this person once and Larry David's in the back and he goes oh you're doing the chat and cut I'm not going to allow you to do this there have been no fewer than 10 times in my life now where I've been

in a line and I've had this thing where I've seen a long line I've started to think about the chat and cut and I do think maybe enchanted's the wrong word but what he was going for in the conversation is it's the most mundane thing ever that you've now brought they turn into a whole story and uh that's what he was trying to get at you know what I like the comparison of is drawing with what you were just talking about that my kid is 10 years old now and I think it would be wonderful for I was thinking about this for him but for any of us to learn to draw because of the way it makes you look at details so well right like there's this idea that anybody can take apart a car but can you assemble a car right so I think of drawing it's kind of like assembling I could see it's one thing to look at a tree sorry I'm kind of doing this I'm looking off camera at this imaginary tree it's one thing to look at a tree but it's like can you recreate

a tree it makes you pay attention to the details so much more so I wonder if comedians whether stand-up comedians are the other kind I don't know have to pay super close attention to these nuances in life like that like Larry David's specialty is social norms right like all that stuff going back to Seinfeld was all social norms um and call out social norms by paying close attention to them that's kind of fun this idea of like you have to pay attention to details to be good at what you do you have to pay attention to details to be good at drawing you have to pay attention to details to be a great comedian have you heard the David McCullough story on look at your fish neither no okay so David McCullough he just died which I'm really bummed about but he was a big painter he spent as much time painting as he did writing he said it forces you to look and I don't know if it's apocryphal but he says he had a a college teacher and the when day one he

it's a writing class and the teacher plops a fish on the table and leaves and goes right about the fish 20 minutes later teacher comes back and goes would you write as students go we didn't write anything you put a fish on the table there's nothing to write about and the teacher goes no keep looking and by the end of the semester they're expected to write like 3 000 words about the fish and the whole point is that you just weren't looking closely enough the fish was there you can write about the scales you can write about the color you can write about the history of the fish all these sorts of things and the whole point is just what you're saying to be more focused on the details why did you choose not to read when you were writing how to live oh because I was trying to put everything they had ever learned into that one little book um the rough draft was 1300 pages I was really doing like a life dump I've heard a few other parents

have this idea like when your first kid is born and you think oh my god what if I don't live until they're old enough I want to tell them what I've learned I wanted I want to share my wisdom I want you to tell put them everything I've learned into a book I've heard a few different parents say this to me and I'll admit how to live was a little bit of the same idea I was trying to put like everything important I had ever learned in my life into this one book and that's why I didn't want to read anything new because it's like I was already at a rough draft and what if I were to read an amazing book and suddenly learn something new about life I'd want to put it in there so it's like no please don't give me any new wisdom I'm on my rough draft I can't take it so um yeah that's why and you don't feel like reading could have helped you access things that you had known but had forgotten about no because I do my notes I started doing this in 2007 I ran hundreds of books

before 2007 but it was in 2007 I realized I looked at this one book that I had read like only five years before and I went huh I know I read this but I don't remember a damn thing from it it's like this is sad it's getting lost all this stuff I've read is getting lost in my brain so I started at that time just keeping a pencil in my hand when reading books and underlining every cool idea or just circling a cool paragraph and then when I was done with the book I would open up a text file and type out my favorite ideas from this book often paraphrasing um that's the ideas that like or it was just to capture the idea so that later I could just go back to the text file and review it in a few minutes and I could just you know give away the book lose the book I wouldn't have to read the 300 page book again I could just read the two pages of the ideas that I found the most interesting in this book so I just kept up the habit ever since and after doing it

for a few years um I started posting them on my site I was worried that that would violate copyright somehow but nobody's complained yet um so if you go to sieverssive.rs slash book you will see I think it's up to 330 books now um every time I read a nonfiction book not fiction uh fiction I just enjoy like a movie but when I'm reading a nonfiction book I jot down the most interesting ideas and I post them and I review them often um I'd say every week I go back through my notes from old books I've read and I just scan the notes or sometimes if I'm wrestling with a particular problem I go back to the books that were written about that topic that I'm having a problem with and I review those carefully and I think about how I can apply what I read eight years ago to my current situation today it's so useful talk about one of the best things I've ever done like yeah taking book notes like this has been one of the best habits I ever did that's why I didn't when you

said like help me remember something or to kind of solidify something I knew I had already done that so I really just wanted to stop taking in new information and just output what I had learned up until this point just so I could get it done I'm choosing these words carefully I really admire there's a pairing of simplicity and discipline that I sense that you have are do you identify with those words are you saying yes or do either of those words feel like the wrong words oh no both dead on yeah you're so methodical you know you've been doing this for 15 years with booknotes and but then also there's a simplicity like even your URLs are so simple that you can just say on a podcast I'm not hyper disciplined but I am hyper simplified everything I do I'm constantly

trying to get to the like how can this be simplified whether it's an idea whether it's my life whether it's the essence of everything we do on a daily basis and how does that help you write like like where does this show up in your writing process what's going on well uh yeah if you go to sibe.rs slash seven you will see my bullet list of my writing process which is to dump out everything I'm thinking on a subject I do the full unfiltered brainstorm into a text document I just dump and I every single point I I argue against myself I question it and then I answer my questions and I question my answers and I do all this back and forth until it's exhaustive and I just feel like that's that's that's all I have to say about that but then I go back to it and I go okay this is a mess um what's the gist of what I've said here or what's the gist of my conclusion and then I literally make a good old-fashioned outline with a little bullet points and just a few

words in each point not even a complete sentences and so I like well and of all this hairball of a mess of thoughts I have here I think the gist is this and then I look at those few sentences and I think okay so really all I need to say is this and I'll maybe add in a couple sentences just for context maybe I'll take point three add a couple sentences that need to be said because it wouldn't make sense without those couple sentences and then I look at that it's like 22 sentences and I think there you go that's done and that's what I end up posting so I think the average length of an article on my website is 22 sentences and it's because of this process but it's it's everything in life I mean the where I live and the computer god even if you were to see the way I use a computer speak out my friend Amber rhubarth who I mentioned earlier let's just mention her again um she just was at my house and

like looking over my shoulder once as I was on the computer and she goes like I have never seen somebody use a computer like that this is so weird and it's because I spend most of my time in a black unix terminal like full screen there's not even a menu bar at the bottom there's not a clock at a right I don't want a single pixel on my screen that doesn't have to be there and so because of that I found I use an obscure operating system called open bst because it was like the most middle most I could find I and even on open bst I usually this obscure window manager called rat poison because it's the only one I've ever found that removes every single pixel from the screen except what you're working on no menu bar no icons in the top right corner I hate all that clutter so um yeah so then I do everything often without any graphics at all no mouse just like this raw unix 70s terminal plain text and it's like ah there simplicity I like this you know it

just gives me this deep sense of uh contentment like there this is how things should be even you know like when it came to the like the cover of my books I worked with like 12 different graphic designers that came up with like 36 different cover designs for my books and with everything I was like no it's just I want it simpler I want it simpler and eventually I thought wait a minute like why do I need images on my book cover I love it what you find a hard cover book and you take off that glossy shiny outer wrapping and what you have underneath looks like a library book you know like just the title the author that's it I thought damn that's so badass see those books look wise and you see those old books with just the title and the author and that's it and so yeah that's what my books look like and it's because of this I'm just so many things in life it my wife gets a little annoyed with it because I tried to do that in

her house too and she says but I don't like that that's too minimalist it's sad I'm like all right all right all right I'll draw the line there I'll do it and other things in my life including my my office and uh and my writing and my computer I'm just constantly pushing for the simplification oh my code I spent a lot of time programming yeah you mentioned my URLs all of this I'm just constantly asking like how can it be simpler what's the point of trying so hard to make it right it's not trying to make it right it's just trying to get to the essence of things because it the rest feels like clutter it feels like waste it feels like excess baggage it feels like pollution like it it's noise signal versus noise I'm trying to just get the signal and get rid of all the noise even you know in a sentence these words that don't need to be there they're just clutter they're distractions is those little comma phrases uh when people say things like well going forward

or uh on the other hand or you know come to think of it uh all these kinds of phrases just aren't necessary we could just say the thing um and uh yeah I'm trying to get to the essence of things to to get rid of the pollution like that's when I say the pixels on my screen and using rat poison um it's because that it feels that's visual pollution and I don't want pollution in my eyes I don't want to put out pollution into the world I don't want to put out sentences that don't need to be there um yeah that's that's the real point how much of this is a Derek saying versus what it means to have something of quality for example take something like the Sistine Chapel magnificent not distilled to its essence you know if you've been to Paris it's one of the most ornate cities you've ever seen just everywhere every little balcony every little uh the eaves on every building just have all those little squiggly squiggly squiggly it's just so ornate

yeah it goes against my sense of like uh none of that's necessary but I'm like yeah all right it's just a different approach I mean which when it comes down to that's what my book how to live was about is that life is not a problem to be solved but it's a paradox to be experienced that you can believe one thing and you can also believe it's opposite and you can even live one thing and also live its opposite both can be true so I'm a Paris guy that's my favorite city of the world the aesthetic of Paris like that's what I try to invite in my life and I struggle so much with simplicity every time I share an image of a space with someone whose taste I admire their response is always that it's cluttered but the spaces have life they have energy they look like they've been used they look like things are happening in the space and what I love about talking to you and reading your work is you're always making me question why am I like that why do I

believe that and I think that's something really it's really cool about the way that you do things is you're so aligned as a human and so clear on what it is that you do adult value and that that alignment that resonance with who you want to be and who you are and how earnestly you work to try to bring those two together I think it really shows up in your writing because that's what it is it's trying that refinement it's just cool to see the synthesis of how you live how you write thank you it's funny how we we must have different mental associations with certain traits it reminds me of when I moved to Singapore it was hard to find any silence Singapore is all dense there's almost none of it that's not dense it's just one little island and so shortly after I got there I thought god you know what would be wonderful is to make a co-working office space but call it solitude like solitude.sg and it would be

working spaces for people who want silence and so I batted this idea around all my Singaporean friends shortly after I arrived and everybody was against it in their gentle ways kind of like yeah maybe we'll see you know but then some were more confrontational and said like no that's just not gonna work here that doesn't work with the culture and they said you have to understand Singapore is like two-thirds Chinese heritage like Chinese ethnicity and in Chinese culture noise is life silence is death and we like noise like that's vibrancy it's life it's alive so people like to work in busy noisy spaces and it's just you know where you get your energy and and whoa okay so that's like culture you know in the same way that you're these things like you know in China people wear white for funerals so don't wear white because it means death or something like that or people have different cultural associations with different things so

I think about that when you say that you see a cluttered space and to you it means life and there's things going on here that's and Paris suits me and all that so it's like it's cool you've just got different mental associations with these values traveling is a fun way to go to a place not that's pleasant and similar to where you grew up but ideally to go to somewhere that's so different from where you grew up so you can see a different working philosophy like I think that the cultures of countries are philosophies in action they're applied philosophies and you can see a working culture that values very different things than you that does not value individualism or does not value ambition or does not value pleasure or does not value you know things that you think of is just um unquestionably true or unquestionably valuable another culture might not value those things and it's cool then to not just visit and take some pictures but to to get into it and try to

import try to adopt that mindset and try to see the world that way you wanted how to live to be very persuasive how did you go about achieving that you and I have a uh a mutual friend Ellen fishbunny yeah I worked with her writing doc coach service uh William I forget his last name George now thank you yes I worked with him on how to live I worked with a bunch of editors constantly trying to give me feedback like is this persuasive how I how can I be more persuasive in the end um I got some some advice I did the best I could um the only test I had because by the time it was like getting down to those final revisions I had been working on it almost full time for four years I just wanted to get it out so all I know is that I was persuaded as I was writing it that each time I was writing a chapter I felt like you know what forget those other chapters this is it this one has the answer this is how to live and I was completely convinced

myself that this was it and then I'd work on the next chapter which had the opposite point of you and I'd say you know what actually what was I thinking yesterday that one is this is it this is really the way to live and so I persuaded myself very well I don't know if it was persuasive to others but I had to just draw the line somewhere and say I think it's good enough people ask how do you know when you're done and you never really feel done and it's frustrating and I've published pieces too early where I needed to work on them more and I didn't have the courage to look in the mirror and say I needed to make a change and for whatever reason I was afraid to do that maybe I co-wrote a piece with somebody and I was afraid to tell somebody else that something that they wrote was a good enough for vice versa and then I've also written pieces going back to the beginning of our conversation that I spent too much time on in a way and now

I've been working through this and I think that when you were talking about the seven ways that you write one of the things that I think I'm missing is that you can have an epiphany after you've been working on something for a while and once you have that epiphany you can just run with it you can roar you can sprint take off like a cheetah and what I mean is that it's okay to be working on something for a while put that on the other side and just write from memory I think it's Jordan Peterson as that one of the best reasons why you should write from memory is that when you do that is this compression algorithm in your head where your brain is automatically separating what is the signal from what is the noise and I think that that's super helpful and so I've sort of worked my way out of this with something I'm going to try which is it's okay if I work on something for a while but often and the question is how do you

know when I probably need to start all over and write it and I'll run through that compression algorithm and still maintain that giddiness that I think is part of good writing nice I like that yeah Jordan Peterson says the same thing about things like the bible and fables where he said like you understand these oral traditions have let everything fall aside that wasn't important in these stories everything in these stories is important I like that buying this book was really fun and I don't think I've ever said that about a book I bought it on your website you had could follow up emails and then I got all your books in the mail at the same time why do you sell books in the way that you do few reasons I mean for one it's just you think things could be done better you don't just want to be a book on amazon with that whole mess and maybe you don't fully support amazon and don't think that they that the world should be giving them more money

but sometimes you just feel like things could be done better and so with selling books I just felt that I could do it better than amazon there was a time when I doubted that I thought what am I saying you know just and I thought wait a second I'm the I'm the guy that started CD baby I've done this before I've built a store before I can build a little store for my own books I can do this and it's part of that simplification by building my own store I got to simplify things even more instead of throwing people into a big grand bazaar full of noise and clutter it's just a nice simple site that says here's the four books but then there are also pricing things right like I never liked the fact that if you bought a paper book and now you want the audiobook you have to pay for it again to get the audiobook but now you want the ebook and you have to pay for it again to get the ebook I just thought you know it should just be that the means of delivery to get the words from

my head to yours the means of delivery shouldn't matter like you should just be able to buy the book meaning the contents and whether you want it on paper or ebook or audiobook or I am actually just releasing a video book today um that that shouldn't matter um it should all just be the same price and it should all be included so you buy my book now and maybe you have the paper book shipped to you and maybe two years from now you've given away the paper book but you just log into my site and you get the ebook and then four years from now you feel like listening to it on a hike you get the the audiobook and it's all included uh so that was one thing the other thing is I give all the money to charity hundred percent I keep nothing for myself so if I sell it on amazon much less goes to charity you buy it directly from me the entire fifteen dollars goes to charity that was another reason um another reason was the long-term relationship with the

person who buys it so if you buy a book from me I like that I know you and I know that you've bought this book and you I you get an email that's actually from me and you hit reply and it actually goes to me and it's like a direct conversation um and that I learned from experience um running cdbaby where I started to get some former rock stars that used to be famous in the 80s or 90s would put out an independent release directly through me through cdbaby and more than twice at least twice I can think of two concrete and I think I heard it a few more times these former rock stars would say you know I sold a million albums through Warner Brothers or EMI or something but selling a thousand directly through you means more like it feels better because I'm actually seeing the thousand people that bought it because the way I ran cdbaby is I would let you know every time you sold something here's who bought it here's the

name and address and email address of the person bought it and even often the comment on how they heard of it you know heard you on kexp went and searched your name found it you know and the these former rock stars would tell me that it meant more to them to have a direct connection with a thousand fans instead of just hearing from their label you've sold a million copies so um yeah having sold my first book on penguin I knew that that would feel better to sell directly so stack up all those reasons and that's why it was you know a no-brainer for me how do you think it changes your writing for one thing you don't have to go through a publisher but I've actually never had to please a publisher um the only publisher I worked with penguin just kind of bought my finished thing from Seth Godin um so I did I never had to like please a publisher but there's one thing you know we haven't talked about I don't think I've

ever talked about this publicly is when I made the decision to print hardcover books you know you're you talk a lot about online writing and I used to think of all of my writing as being online only but once I made the decision to print hardcover books it was like all right I'm gonna be killing trees and if I wasn't succinct before that made me even more succinct I was like I want these books to have the least number of pages possible it made me go back and look at every sentence like is this really worth killing a tree over and every sentence had to pass that test like all right this is murder worthy yeah here the same thing with people who used to hand write and then they'd have to put it at typewriter just say the same thing I was reading uh Shelby Foote he was one of the great civil war historians and he was a novelist and he was one of those Paris review interviews that are just incredible all of them like interview quality bar Paris review top notch and he said

that one of the big problems with writing on a computer is that there's a lastingness to things that you write on a computer because you can copy and paste it that there isn't with handwriting and putting it into a typewriter I like that again it's like what you're saying with the oral tradition the things that get worn down through writing from memory or retelling and just the just the stuff that needs to be there it's a cool common thread so then what is the role of online writing in your portfolio hmm my number one bit of advice when people ask my advice about writing a book is I say don't think of it as a book put one idea at a time out into the world like shine a spotlight on each idea because it would always make me sad that there would be these books that I would read all the way to the end and sometimes there would be a brilliant idea on page 280 and I've read the statistics of how few people will first how few people buy a book and how

few of those that buy a book actually read the book and I thought man there's so few people reading this idea on page 280 I wish this idea would have had its own spotlight and I think that's a reason to post individual ideas online as individual articles um get them out into the world let them breathe let them get some feedback um don't just keep them in your own private locked secret um area release them to the world then the world can can give you some feedback on them you can test them out you can see where you might have been thinking about it wrong or you can get people applauding and saying oh my god I love this idea and then you take all of these things you've these individual ideas you've posted online and then you can turn them into a book with a greater sense of confidence that these are the that these ideas are ready as a collection of ideas in a book that's how I see it how do you think that the shareability works

differently in the sense that when somebody shares a book with me the chance that I read it is much lower but the weight of the recommendation is much higher both in the added friction of sharing a book and if somebody shares an article with you they say hey check this out this is pretty cool someone shares a book with you they say this changed my life yeah I have nothing to add I agree you wrote anything you want in what 10 days yeah I didn't ever mean to write a book and then Seth Godin like literally called me out of the blue my phone rang from an unknown number and I answered and I said Derek it's Seth Godin I went oh my god hi and he said uh I'm starting a new publishing company and I want you to be one of my first authors will you do it I said of course so he said okay I'm imagining this he's actually the one maybe to blame for my short books he said where these aren't going to be like usual books they're going to be more like manifestos he said

I want like 10,000 words 11,000 words they're going to be a manifesto and I said all right he said so uh yeah go I said okay and so I just kind of looked at some of the things I'd written already um it's about half of it just telling my stories of how I started and grew and left CD baby and I realized there was a lot to be told but it was just it was because I was just telling stories from my life it's like things speaking of going back in our conversation these are things that I had all talked about with friends before I talked about them even to crowds before I had spoken at conferences to rooms of hundreds of people where I had told these stories and I had heard the audience laugh at this point and I knew that that was a point that should be kept I told these stories to friends and I wasn't having to conjure new insights I was just telling my tale so yeah I did it in I mean not just 10 days it was a probably a total of like 20 hours

and then I sent it to Seth going what do you think and uh he said yeah it's great we like it um and it came out like a week later and that was it how do you think about mastering this craft I mean you talk about I just love this idea of mastery because what happens is when you first learn to write right we know school this isn't a criticism it's honestly it's learning every single craft you got to learn the basics when I went to basketball camp through the legs spin move behind the mat behind the back the crossover the four dribbles that every point guard needs to know and I I still have my basketball coach Elliott Smith telling me that hundreds of times and when you write it's the same sort of things you got to know what is the role of a comma what is the role of a period what's the role of a semicolon delete it what when do you have a paragraph break all these sorts of things but then what I think is beautiful about mastery is mastery is divergent

mastery the road to mastery begins when you say that I need to start asking my own questions and start answering asking questions that haven't been asked so I can find answers that nobody else has found and how do you think about doing that well first I should say I'm not just saying this because I'm talking to you now if anybody were to ask me who do you think like who do you know is on the path of mastery to being a great writer it's like mastering writing I would say David Prell like I think thank you are the embodiment of the mastery path to writing I so admire that means a lot not just what you're doing now but every like the whole approach that you've taken I think it is the way to go like you are mastering the craft and I so admire it and I think that's what's what's amazing like you've dove in to this one thing a hundred percent I think I've always for forever if I thought about writing at all it was always secondary you know

like I was mostly helping musicians and then sometimes I would write a little story that I thought was worth sharing that I thought would help musicians but mostly I was like hands on helping musicians then I was mostly running a business and every now and then I'd write a little story about something I had learned from running a business but I always thought of my writing as just telling some tales on the side of the side effect of what I was doing I was never focused on the craft of writing the mastery of writing itself the story that I tell myself is I have way below average writing skills and therefore I need to work harder than everybody else to learn this craft what is your process for becoming a master writer okay you've you've made some quotes here I'm gonna quote somebody I don't know who said it but some musician at some point said if you can learn music you can learn anything and I love that because if you think of

the typical path of learning an instrument lots of playing your scales not just scales but arpeggios and this co-different chord patterns spread out tight it's digging into these little details um when you hear a musician practicing it should sound bad musicians practice what they can't play musicians don't just sit there and play what they know all the time or if they do they would suck they would just not ever get any better when a musician is practicing what they're what they're playing is the awful sounding things because they can't play it yet it's like

okay wait wait closer okay there we go I did it once let me try it again and they just they'll take this thing that they don't know how to do and they'll just do it again and again and again until they finally feel like all right I think I can do this now now let me go back 10 seconds into the piece and make sure I can play this difficult bit in context you know did it you know but even once you've done it once you practice it again and again um you focus on things you can't do oh and you you dive into others people other people's work that you admire and you try to distill what is it that I admired about that so we would analyze songs um and try to figure out what made that melody work so well like exactly what what note made that phrase intriguing what chord kept me listening instead of feeling like switching it off or what word pulled me into this lyric um and then you'd extract the technique and then we'd say or actually you know I took

songwriting classes at Berkeley School of Music they would say okay I've showed you this technique today um go write me three songs using this technique by Thursday and so people would have to just come up with three songs that use this technique let's say of when you've got an eight bar phrase the usual thing is to do a four bar phrase a four bar phrase instead they'd say try breaking it into three and three and two or other unusual combinations give me a five bar phrase five bar phrase and a three bar phrase to use the eight bars and that would be your challenge for Thursday go and it was so fun to write in this um let's say left-brained way we think of songwriting and writing is just pure creativity and so to take certain rules and apply it to me is is creatively liberating because it's just saying all right I'm just gonna do this technique and actually some great songs of mine came out from these little challenges look at what musicians do to master their craft

and think of how you could apply that to whatever you're trying to master not I mean we're speaking mostly to writers today but say if you're trying to be a great programmer or what would it look like to try to master entrepreneurship the way that musicians practice their instrument like could you actually like start a business every day but could you start a hundred businesses just to practice the craft of starting a business um the answer is probably no but there's an idea in there somewhere so yeah that that to me is the path yeah my little phrase that I like to use for this is practice analytically perform intuitively and it came out of a really cool experience that I had when I was 13 years old I wanted to compete as a college golfer and during my freshman year high school I started playing in these tournaments this tournament was in Fresno and I remember being on the driving range with this guy Bryson Dechambeau who was like one of the big 15 year olds at the

time or something like that and he won the tournament by eight shots I remember watching him practice he had his coach out there he was so focused so regimented and I remember driving home with my three best buddies from high school back to San Francisco and we were like we don't know who this guy is but he was so much better than us last time I checked he was the number five ranked golfer in the entire world and what I learned from Bryson was this this sense that you can practice like that but he won the US Open two years ago Saturday had a tough day Saturday night goes to the driving range and the last words to his coach before he left the range on Saturday and won the next day was all right I found my feel now I'm just going to go play like fun on Sunday and I love this idea that you would deconstruct everything when you're in that practice mode but then once you find the feel you let that analysis that learning that left

brain move through you the right brain kicks in the intuition flows there's a whole book about this called the inner game of tennis great book you know it oh cool yeah have you seen a youtube video on it no there's a youtube video where Tim Galway he shows basically takes these women and is working with them to hit and he just says ball hit or bounce hit bounce hit and they go from being in this analytical mindset to this intuitive one and they start rocking it it's it's impressive do you feel intuitive when you're writing even though you're doing some of that analysis I try to focus on the you know we've we've talked a lot about the craft today but going back you know I think that again the craft is pointless without a good idea underneath it so I try to mostly just focus on the core idea and then when you're talking about just sharing an idea you've had to me the whole idea like intuitive versus craft it's just for the most part it's

like talking I try to mostly I like to write like I talk you know my last book how to live was an exercise and like how can I take 1300 pages and instead say it in 112 so that's why you got this kind of hyper compression or every page what was a page is now just a sentence but for the most part I think my writing is just a simplified version of how I talk and so I don't no I don't really put conscious craft into it so much you're right yeah I guess if you'd call that intuitive that that almost feels like all over glorifying it um because it's not even like sports it is just like talking but editing out the unnecessary words did you see the movie midnight in was it midnight in Paris the Woody Allen movie where so Owen Wilson goes back to 1920s Paris the my favorite thing about this movie are two characters for one um the guy that plays Salvador just does this great like I'm dali dali but the guy that plays Ernest Hemingway he talks

like Ernest Hemingway writes and it's powerful I love the way that he says these direct sentences he says them he concludes them and he stops talking and I love that and watching that movie I was like damn it see that's a way to kind of like to walk your to walk your words to walk your talk the way you write um is the way that actor plays Ernest Hemingway in midnight before Paris I recommend it just for those scenes alone a lot of people struggle with that like if you read the writer of somebody who's just left sixth seventh grade and they're trying to write based off the novels that they're reading and stuff it's so over the top it's just trying too hard and write like you talk is the most obvious advice that no writing teacher ever told me I don't know what's going on with that to me I think the biggest problem to unlearn from school is page count is feeling like something has to be 10 pages on a subject um and if you think you get a book deal

that it has to be 300 pages um I'm constantly trying to say like how can I make this shorter how could I say less whereas I think we spend so many years because of needing to turn in assignments like you said about the fish where we feel we have nothing to say about this and so you use all of these padding words because they fill up more space and it makes it sound like you're saying something when you're actually saying nothing and um that's to me the the hardest lesson from school to unlearn Jason freed at base camp has a little post called the writing class I'd like to teach and he says take an idea write two pages about it write one page about it write one paragraph about it write one sentence about it there you go communicate the same amount of information yeah we're kindreds I love his style how did you meet Tyler Cowan did you just reach out to him out of the blue I think yeah I I reached out to him and I said hey I'm 22 years old

I am living in New York City I would like to go interview I'll take uh I'll go down to DC I had no money at the time so I took a five dollar megabus and it was packed I'm sitting it was the last ticket so I'm sitting in one of those you have the middle table and it's like seats of four and traffic the whole way down and our legs are just like rubbing against each other terrible experience but I go down have a have an hour with Tyler and I remember at the end he said you're a kindred spirit I didn't know what a kindred spirit was at the time I didn't know what that was so I get out of the room I look up what is kindred kindred spirit mean I'm like oh well that's a really nice compliment and a year later I get a 20,000 dollar grant from Tyler Cowan which allows me to start right a passage otherwise without that money I wouldn't have been able to and you just you cold called him I love that I think there was even a story I listened to the

interview you guys did together where you said that you emailed him some long piece you had written and he replied back almost instantly you were like how the hell did you read that in time and he actually had like critique on your piece and had read it it's just I think yeah people underestimate how effective it can be to just cold email somebody and make that introduction because ideally if you have enough um self-esteem you think of yourself as worthy to speak with too and the people that are putting themselves out there publicly are the ones that like this two-way connection there are plenty of people doing what we do that just stay head down and silent and don't talk to anybody but the ones that lift their heads up to the world and put themselves out there like this are the ones that like the two-way interaction with people so like Tyler obviously does it's really nice to just get somebody who reaches out with something earnest and that is

it just some kind of templated email because it just reminds you that what you're doing is moving people in some way and there's always some insecurity that you have when you're a writer like am I actually reaching people am I actually are these just like words that are being lost to time are they just evaporating or are they actually reaching somebody you can look at page you numbers but like one email does so much more for you than seven figures on a page for your number it's just a number do you know that actually again I know a lot of famous musicians from my years in the music industry and all of them sincerely love it when somebody would come up and do that thing that we think of as like oh I'm just fangirling I'm just fanboying I'm just gushing we go up to a musician that you love you're like oh my god like this song you wrote made such a big difference to me you know I love this work and and it's like I think it's actually their favorite part of the job

it's like that's what they live for is getting that kind of sincere personal gushing feedback when somebody says that it means everything to them right and so yeah when I as people ask why answer my email every day it's because every day I check my email there's something really nice in there and somebody's telling me like I don't know just telling me nice ways that something how something I've written has helped them and in fact I'd say that's probably the single biggest motivation for my writing at all is because of how much it's meant to me when I've read a book that introduced a new way of thinking of something that blew my mind made me think of everything differently and how powerful that was and how it like permanently changed the way I see the world and then so when I have some kind of epiphany or insight I try to put it out in the world in the hopes that somebody somewhere from Nepal to Nebraska will read this idea and go oh my god yes this helps

me live my life this helps me see the world in a way that works better for me like that's what I'm trying to do and so when somebody emails to tell me like oh my god this idea of yours made a big difference to me it's like there we go like that's the ultimate reward and one thing I'll add to that is actually do it when people hear something like that what goes through their head is I'm not going to do that because a lot of people don't do it and this person isn't actually going to read it I promise you not nearly as many people reach out as you think and I know from email like you that you're actually going to read it yeah you should always cold call uh cold email people like in fact I do this with every book that I love um all those books that you see on my book list like the ones you see at the top on my website of my the book notes that I've read every time I love a book I stop and I just

find the author even if I have to dig hard to find her email address I will find it and email them and say thank you I loved this book and here's why and they almost always reply it's so rewarding the reason I do a lot of these uh podcasts is the main thing is because of the people that I meet afterwards you know the kind of the kind of person who listens all the way to the end of an interview like this is my kind of person so if you listen to the end go to my website and email and introduce yourself Derek this was a blast I feel like this was was years in the making and it just was one of the most fun conversations I've ever had about writing so thank you me too thanks David