29: Billy Oppenheimer - Attuned to Clues

Welcome to Dialectic Episode 29 with Billy Oppenheimer. Billy is a researcher and writer and works closely with author Ryan Holiday as well as Rick Rubin. He also has his own newsletter, Six at Six on Sunday, where he shares his favorite ideas, excerpts, and patterns from his extensive reading and research. The beautiful thing about this is that in many ways it's simply the exhaust of his incredible process. 6 at 6 is really about the inputs, not the outputs. Billy's also working on his first book, The Work Is the Win. Billy's someone I've admired over Twitter and his newsletter for years, and we got to meet earlier this year over a coffee that ran about 3 hours longer than it was supposed to. In this conversation, we sat down and I talked to Billy about so many of the wise, inspiring, and amplifying ideas he's uncovered over the years. We begin with a story of Billy's about working with Rick Rubin and Rick's process of discovery when he begins a new project. He calls this looking for clues, and it's hard to think of something that better encapsulates what Billy does day to day. If I'm honest, it's also the best framing I've encountered for what I do when I prep for these conversations. If you enjoy the episode, please give it a rating on Spotify, Apple, or a thumbs up on YouTube and share it with a friend. With that, here's Billy Oppenheimer. Billy Oppenheimer.

Here we are.

Here we are. Uh, this was, I'm, this was supposed to happen a few weeks ago and I had to push and I'm very glad to be here.

Yeah, I'm glad you made the trip.

We're going to start with one of my favorite things you and I have chatted about. I'm going to start with a quote from Twyla Tharp. She says, that's what I'm doing. I'm digging through everything to find something. You've talked about reading as a sniper. Can you talk about what it means to search for clues?

Yes. Looking for clues. So I started, I started doing some work on a kind of like research assistant basis with Rick Rubin a couple of years ago. And the first time I met him in person, he, he was like, maybe it'll be good if I tell you the story of how a creative project went from start to finish. So that you can get a sense of my approach. And he told me the story of a, of a documentary he was working on. I told him recently that I think about it all the time and like, it's perhaps my favorite story of creative process. It was a project that is still in the works. So I want to be careful about some of the specific details that I may leave out, but I think it's just so good and gives a real sense of like his approach and how I have come to think about my own sort of research process. He, he was approached by somebody who had seen a documentary Rick did with Paul McCartney. And the Paul McCartney documentary was just an interesting approach to an autobiographical documentary. In this case, it was Rick and Paul kind of standing over a soundboard and Rick would, would play some of the Beatles songs and then kind of—

I haven't seen this.

Yeah, it's amazing. And you know what it's called? Uh, 3-2-1, I think.

Okay.

And the stage design is just this kind of ominous black and white space, and it's just Rick and Paul McCartney. You feel like you're a fly on the wall as these two are walking through Paul's kind of musical career and breaking down some of the songs and how he wrote them and how they came together. But so, the person saw it and had been thinking about wanting to approach somebody about doing a documentary. I think was drawn to the uniqueness of the McCartney thing and reached out to Rick and asked if he would consider doing something. And Rick said, "I can't commit to it, but I can commit to thinking about it. And if I think of something that excites me, I'll do it." Great answer for a creative project. Yeah, which in itself was like a great lesson of— I've used that a lot since then where, you know, opportunities are presented and it seems exciting in the moment, but it's like, let me sit on this for a couple of weeks. And if I keep thinking about it and I'm excited about it, it's probably a good sign versus jumping on it right away. And oftentimes a week or two in, you kind of regret having committed to it. But so after he said that to the person, I'll commit to thinking about it. He, he began what he calls his clue stage, which is just gathering the components of what he ultimately ends up doing. He kept using the word clues. So the first clue was he was watching a lot of different documentaries in this genre of a main character and their life story and their work is explored throughout the whatever, 2 and a half hours of the documentary. And he talked about noticing they, they all kind of start the same way, which is a cast of characters that worked with, were friends with, family members of the main figure in the documentary. And the implication is these are the people we'll be returning to over the next 2 hours, and they'll help us tell the story of this person. And so Rick said, In the early stages, I like to learn things to rule out things. So he wants to know what are the conventions here? And I'm going to try to avoid those if I can. So some of the first clues are like, what are we not going to do?

There's a version of this idea from this guy Boyd Varty where he calls it the path of not here. He's like a lion tracker. And his notion is like, we often, when we take a wrong path, we can feel like, oh, what a waste of time. And in fact, you're like, by knowing it's not that path, you're actually getting closer to the thing.

Yes.

Which is cool.

Yeah, I love that. The path of not here. Yeah. So that was— he said that was the first clue that, like, it wasn't going to be 10 or 12 people on plush couches, one after the next. The next clue was he was watching interviews with Eddie Murphy, and he said, you notice that in an interview context, Eddie seems uncomfortable and different than his stage personality, where on stage he seems, you know, like very comfortable and like in his element. And then in a one-on-one, sitting next, sitting across from an interviewer, he just seemed out of place. And Rick was like, I, I couldn't tell if it was just the fact that he, he doesn't like to do interviews and it seems like it's a waste of his time, or if he's just shy and if he doesn't have a rapport with a person. It takes some time to warm up, but I just noticed it. And then he was watching Eddie's interview with Jerry Seinfeld in Comedians in Cars Getting Coffee. And he said he noticed that the first couple of minutes it was that kind of same uncomfortable Eddie in an interview setting. But then something switched and he became more like his stage presence. Mm. And he was like, I couldn't tell if it was, you know, just the format of Comedians in Cars is different. They're not sitting in in chairs with cameras directly on them. They're, they're in a car and then they're in a coffee shop and they're moving around. And, or if it was— this is— Seinfeld is a peer that he respects. But I noticed it. The next clue was he was listening to a podcast called Poetry Unbound. And the format of this podcast is the host reads a poem start to finish, and then for the next 10 or 15 minutes just gives more context about the poem. Or about the poet, the time period, some of the metaphors that they're exploring in this poem. And then he reads the poem again.

Wow. Cool.

And Rick was like, what I like about that podcast is that's on the second read. It's like a totally different poem.

Yeah. You have all this texture.

Yeah. He, he compared it to when you go to a museum and you get the headset and you're looking at a, at a a painting on the wall and, and then you, you know, you press play on the, the commentary on this painting. And with this information, you're seeing the painting differently.

Yes. Yeah. One of the— it's one of the things I've come to appreciate more over time is I used to sort of have this view that like I need to experience art sort of like purely. And if I like need to read a review, I watched this Miyazaki movie he made a couple of years ago and I was kind of confused. Then I read a review that I really loved that had all this context. And the second time I watched the movie, I loved it.

Yeah.

And I was like, wait, am I allowed to love it? Do I only like it because of the critic? But I actually think that this is like a really underrated thing of like, there's so many like different, or even just you watch something a second time or a third time or with like different ways that the texture can change the meaning of something.

I think about this all the time because some of my favorite things, movies and bands, writers, it begins with an initial attraction. And then I, I get wanting to know more about who made this. And then I go like an example would be I'm a big Vampire Weekend fan.

Likewise.

And that began with just like a song popping up on a random playlist or something. And I like the song and I'm like, maybe there was a lyric. I can't remember the specifics of it, but for some reason I wanted to know more about Ezra Koenig, the frontman of Vampire Weekend. And I started reading a bunch about Ezra. And I just like really resonated with his kind of path to becoming, uh, to pursuing music. Some of the ways he articulates and thinks about songwriting. And through learning about him and being drawn to some of those things, like my affinity for Vampire Weekend gets larger and larger. And so I think all the time about like the, just that weird phenomenon of how, how your interest and love of something can be informed by like getting to know more about the stories behind, or like if it doesn't have to be necessarily the person themselves, but like a cool story behind how something got made.

Context, whatever, right?

Yeah.

Right. Okay. So he's, he's inspired by Poetry Unbound. Yeah.

So that's another clue of this, like reciting a poem, giving more context, reciting it again. So he has this kind of nightly ritual where after the sun goes down, he turns off his phone. He puts on some blue light blocking glasses and he, he sort of unwinds by watching pro wrestling. And one night he's sort of deep into his pro wrestling stage of his nightly routine and all these clues suddenly kind of come together. And he said, I broke my rule. I turned my phone back on because I knew I, I'd forget it by the morning. And he just made notes of what he ended up eventually doing, which was a series rather than a standalone 2-hour documentary. It was a series of episodes, kind of that first clue of like, what are we not going to do? So this is, was that first initial instinct to, to go against the convention of a 1.5 or 2-hour long feature film documentary. And in each episode featuring a person that either worked with, collaborated, or was just influenced by the main subject of the documentary. Cool. And on the day of filming with this person that was either, you know, the, the main figure's collaborator or somebody that was just inspired by them, they're giving like a address to like a nondescript building and they're, they're, they do hair and makeup and they're given an earpiece and then Rick comes in. Through the earpiece and they're like, they do a sound check while they're doing hair and makeup. And then the person is led by the hair and makeup person to a door and they're just, I think it's through there. And he's like, I want it to be very vague. And they go through this door and there's like an X on the, on the floor and they, you know, they walk over to the X and then like lights come on and they're on like a recreated stage. Wow. And it's like they're in their element. And Rick is in the back of the building next to a projection screen. And he was like, the reason we did the sound check is like, otherwise they would have saw me and like had the instinct to yell up at me. But we'd been talking this whole time. So we continue our conversation.

Yeah, yeah, yeah.

At the same level. And he's like, is it okay if we watch something? And on the projection screen, he plays something related to the star of the documentary, the main figure. And they watch it start to finish. And then he starts it again and has the person, he'll stop and like kind of prompt and like, what are you seeing here? And I think so like in the edit, I haven't yet seen it, but my assumption it's going to be like that kind of Poetry Unbound style of show the appearance, break it down with the help of a, of a person and then we see it again.

Yeah. Yeah. Yeah.

Um, so it's like I was seeing how all these clues were coming together, like the Poetry Unbound thing. The clue of, of just watching all different kinds of documentaries and learning what he didn't want to do. Like, it's not going to be one 2-hour thing. It's going to be a series. The clue from Comedians in Cars of just like, you can do interesting things like on the move or like in different settings. I'm starting to see how they come together. I'm like, I remember getting just like, my arm hairs are standing up. I was so excited by like, this is how it, how it happens.

What's amazing about all these two is Rick didn't, at least as you tell the story, Rick didn't conclude anything from any of these clues when he observed them. It's a, it's a sort of a noticing first and foremost. Like none of these things are sort of necessarily, they need to be acted on or inherently going to like, uh, be made worthwhile. It's just an attunement that might lead to something.

Yeah. Yeah. I love, he was always like, I don't know what it is, but I noticed it.

Hmm. There's something.

There's something there. And I don't know if it will use it or not, but like, seems, seems it's interesting. And just like, that's enough for it to be like captured and like, yeah, yeah, yeah. You know, part of the, the catalog of clues for this particular project.

Yes. Yeah. We have a tendency to need to know why we're This is only worthwhile if I know right now why I'm doing it.

Yeah. Taking in those noticings, letting them marinate, and then at some point they coalesce into a unique creative output. And it was very helpful for him to, to tell me that story and to use this terminology of clues. So he finishes telling me that story and he goes, I can't remember why I'm telling you this. And I was like, you wanted me to get a sense of your approach to a project. And he's like, oh yeah. And he kind of like strokes his beard and I could tell he still was like, I don't know what this has to do with that, but I was like, so essentially we are in the clue gathering stage of this project we're working on. And he was like, yes, exactly. Ah, and it was very helpful because up to that point he would send me, he would text me like a link to a YouTube video, a screenshot from a book he was reading, a clip from like an audiobook he was listening to. And I was, I was sort of like, what are— I don't know what I'm supposed to do with these things. And now it was like, oh, those were clues.

Yeah. By the way, they didn't need to be acted on necessarily.

Yeah. And they might actually not have anything to do with what we're working on, but they might, you know. And so there's just like so many things I love about that. One of them is just like the suspending judgment of is this thing going to be useful or not? Because he's very much like, like I said, he's just sending lots of things that like he spent a lot of hours reading this thing. Not sure if it's going to like pay off in some way on a project in future, but just being in the habit of, of gathering things and, and not needing to know like, am I sitting down to read this book? Will, will this work pay off?

It's really cool. It reminds me, there's this, there's this author, uh, Benjamin Labatut, who wrote this book called, um, When We Cease to Understand the World. And there's a video of him and he's talking about fiction. He's like, people act like fiction is like, you're, you're sort of making, it's make-believe, you're sort of coming up with stories. And he's like, no, writing, and even writing fiction, is, is more like walking and picking flowers up off the ground. And it's a beautiful metaphor for like what creativity is actually like. And so clearly Somebody who might watch this documentary, it's going to come out, or I'm sure other things Rick's done, might think, oh man, like he's just so creative. And in fact, like this is the peek behind the curtain. It's like, no, there's a process of discovery here. You're just combining a bunch of different ideas and parts from different places.

Yeah. There's a great interview with Johnny Cash and he was, you know, he's one of the most prolific songwriters of all time. At one point I like looked it up and the amount of songs that guy had written was just like insane. And he said his process is he has to fill up to pour out. He's got to fill up on, on inspiration and music and art, and even just like a walk in nature can do it, you know. I love that idea of filling up and pouring out. Like, these clues are just like, you get filled with them, and then at some point they do start to coalesce, and you, you form connections, and you see like Oh, these things put together in this way will make for unique creative output. Wow.

You spend a lot of time looking for clues. Mm-hmm. How does that manifest in your day-to-day practice?

A lot of reading. A lot of my clue hunting, I guess, is, is reading lots of biographies. I love like kind of journals of artists or like collections of letters of artists because I'm always just— I love reading about and finding stories of creative people and how they go about their work and how, how things came into existence. And so along with the reading of more biographical type content where I, I just find like those are the best sources for finding those stories, I also like to read I don't know if denser is the right word, but just like more like academic psychology, neuroscience, anthropology, things where like there's concepts and big ideas that my favorite thing is like you're reading a book on the kind of fundamentals of one field and you come across a concept that's like, oh, this story about James Cameron in that biography about how he made Avatar, Terminator, Avatar, Terminator, anything like this concept that, that story perfectly illustrates this concept. And I just love that, that kind of connecting things that, you know, this, the person that's writing about this concept in this anthropology book is not thinking of like Avatar.

Yes.

But, um, yes. So I, I just, I'm always reading. And listening to stuff, I like, I like podcasts, I like watching documentaries. Like, even if I'm putting on like a random playlist and as I'm working throughout the day, I'll often like, what was that line, that, that lyric? And I'll like make a note of a lyric. So just, yeah, everything that like it could potentially be clues. Like, you know, this morning we were having conversations and You're saying stuff that like I make a note of and could be a clue, you know? So just everything could potentially be, be a clue for a future project or piece of writing or whatever. But it's mostly books.

One of the things I love about this framing, and since you initially told me about clues, it's, it just so kind of embodies how I think about what I do for A lot of dialectic. And one of the things I love about it is it captures this sort of just broad attunement or attention that isn't demanding that it like immediately pay off. It's just an awareness. It's a keen awareness. And you're, you're looking for signal to be clear. You're, you're, there's judgment there, but it isn't like it doesn't have to have immediate payoff, which I think is really powerful. There's a, there's a couple of quotes I'd love to read. First from Emerson, who I know you love. He says, learn to divine books. Emerson once advised a friend to feel those that you want without wasting much time. He goes on to say, there is then creative reading as well as creative writing. Emerson said, the discerning will read only the authentic utterances of the oracle. All the rest he rejects. You have one other quote from— you're talking about Joseph Campbell. You say the mythologist Joseph Campbell talked about how reading is like a, quote, divining rod, a way to find what you are uniquely attracted to and meant to do. You've got to read, Campbell said. Find what excites you, and if it doesn't excite you, it's not yours. It doesn't excite you, it's not yours. If it doesn't grab your attention or etch into your memory, it's not yours. What this is pointing to, which ties into the clue thing quite well, is like there is a pretty significant sort of discernment or judgment here. And so I'm curious how you balance— someone who's consuming things all the time— how do you balance that really high bar for what actually makes a clue, or even what draws you in a piece of content, with the reality that oftentimes things aren't immediately the most exciting? Like, I think we've all had the experience where you start reading something, you're kind of not that into it, and you But if you just push a little further through the mud, you, you end up finding like the gem. Mm-hmm.

Yeah, it's a hard question. It's like the, the concept of taste is kind of like in the air right now of like this is the, the main way to distinguish yourself in the world of AI is do you have good taste? And I just, I think it's, it's just the, the ultimate perennial challenge of like making things is finding the overlap between what you find interesting and useful or entertaining and what an audience will find interesting, useful. Like that middle is a really hard thing to pinpoint or locate. And I think it's why like some of the conversation around AI tools is a little overblown because I just don't think that is an equation that can be scienced or solved. It's just always some uncertainty about— I love this thing that I'm publishing, I'm really excited about it. And then there's times where it's crickets, you know, and then other times where you're like, I really like this. I don't know if it's, if it's going to resonate with an audience. And then that thing goes crazy. So it's just really hard to to know how things are going to land and if your taste is going to be shared by, by an audience or a reader or viewer. So I honestly just don't— almost have given up on like trying to predetermine or predict and just really like, it's really just like a feeling and like everyone's had the experience of reading a book and like you can't put it down and You know, you're, you start to read in bed, I'm going to read it for 10 minutes and like the next thing you know, it's 2 a.m. and you're still like, yep. And so I'm just like always looking for those kind of books generally and just that feeling like specifically of something's like grabbing me here. I can't stop reading this. And I do think you just get better at noticing it and, and maybe developing a system for like what to do. When you have that feeling, capturing it and organizing it, coming back to it.

What about when presumably not all of you— you find all kinds of really interesting things and you are literally a professional researcher in some sense. What about when it feels like some of the time inherently, I'm sure it feels like you're searching for a needle in a haystack. Like, do you have a sensibility for like Knowing how far to keep going, like in, in a world where the first chapter of the book isn't that interesting, like how, how does that decision-making process happen? Or are you actually just, you're just like, I'm sniping only the good stuff. Like if it doesn't hold me, I'm out.

It's a little bit of that sniper thing. I do think part of the job of a, of a writer is the work of making a story or an idea compelling. And so I'm not— I'm quick to just like give— quit books. And like I said, that just that feeling of being hooked into something like that is what I'm always looking for. So if it's not happening, I'll put it aside. And there are times when it's like I've had it happen where on a first attempt, I'm not, for whatever reason, grabbed by this book and I'll put it aside and then come back to it a year or two later.

It'll find it when you're ready.

Yeah, you find it when you're— it's like I just didn't have the reference points yet for this to be really interesting.

Yes.

In the way that it now is. And so like now I think less that like I'm quitting this. I'm like, it's just not for me right now. I'll maybe come back to it. And at a later date it will hook me into it. But yeah, I just think like I do talk to a lot of people that are just like, when I start a book, I have to finish it.

Yeah.

And often they're stuck on a book that they've been trying to finish for—

and thus they're not really reading.

So they're not— it's counterproductive because it's like you think about wanting to sit down and read and you remember, oh, it's that book I'm not really enjoying, so I'll do something else. It's like, yeah, reframing it as like I'm quitting and I'm not finishing because I think there's some part of like people that are like, when I start things, I finish them. Yeah. And so I can't quit this book. It's like you're not quitting it. You're, you're putting it aside for now. And it's kind of just like a little bit of a mental reframe. But I do that a lot. And, and I just always have— anytime I see somebody that's like mentioning, like, you know, you might tweet about a book that you're enjoying or I'll listen to a podcast and they'll make an offhanded comment about some book. So I'm always like ordering books that are coming in. And so if something's not doing it, it's like, let me crack something else open.

Yes. Yes. One question that kind of relates would be you have this line somewhere where John Mayer is talking about top 40 music.

Oh, yeah.

And he says people aren't wrong.

Like, The audience isn't wrong.

Yeah, the audience isn't wrong. And so I'm curious how you think about sort of like mainstream influences and making sure you've talked about in that context, like making sure you're still tuned in to what the market wants.

Yeah.

And also finding the like really unusual or unlikely influences, like almost like the barbell.

Yeah. Yeah. I love that idea from, from Mayer of just like, and it's kind of contradicts what I was saying about like Rick learning things to rule out things like he's, he's, he's tuned in to the top 40, not to like mimic or like, let's, let's— okay, this song is a hit. Let's like follow this as a formula. I think that is a trap.

But it's also just like on the record to be like extremely just like, I don't care about anyone, what anyone else thinks.

Yeah, yeah.

I don't care about the market at all.

Yeah. But he's like, he is a voracious consumer of just like great art and great architecture. Like he loves just like great things. I think the mistake is like reverse engineering something. So I— you see this a lot in the nonfiction book space where if you go to a bookstore and pick up like a new nonfiction book, it's probably trying to be Atomic Habits. You know, it's like a 4-part structure, a dramatic opening story, diagrams, because that is the format of Atomic Habits. And I always think that's like the wrong lesson to learn because Subtle Art of Not Giving a Fuck, for example, another massive book, very different structure. Psychology of Money by Morgan Housel, very different structure. So I think the, the lesson is like that, that was perfect for James Clear's content and his ideas. And likewise, Mark Manson's structure was perfect for his ideas. And so it's, it's finding, it's being tuned into like what is working, but not following that as like scaffolding that like, all right, let me just like, yes, jam my things into a 4-part structure with a dramatic story. But then on the other side, you can, you know, there's like the anxiety of influence thing of not wanting to look at Atomic Habits because you don't want it. You don't want your ideas or like the structure you're thinking about to be contaminated by like thinking this book was a massive bestseller. Like my book doesn't really look like that. Maybe I'm off track, right? So there's like a fine line between being tuned in but not following it as a recipe book or whatever. And then on the other side, just completely like being oblivious to it and being like off in a cave and then coming out with this thing and like—

You're not tuned in.

You're not tuned in, you know.

What about the other side? What about like the really unlikely influences? How do you go about finding those?

I guess it's just kind of like following threads of— like, one thing I do all the time is when I'm reading a biography and it's like the person that the book is about, there's a section about how like they read and loved this book. It's like, okay, I'm going to check that book out. You're just following the rabbit holes. Following the rabbit holes and like, yeah. And I don't know if I'm not like really systematic about it. I just am like following curiosities and, and then you stumble on someone that's like, is more niche or less well-known. And, but I'm not like, uh, specifically conscious of trying to do that.

Yeah. Well, I think it would be hard to be systematic about finding the edges in some way.

Yeah.

I want to talk a bit about maybe the second part of the process downstream of clues, which is like how you build this cultivating an external brain, in your words, like how you build this sort of like scaffolding to, to collect all these things. First off, a quote from Goethe: "The greatest genius will never be worth much if he pretends to draw exclusively from his own resources." Which is a banger. Amazing.

Yeah.

You go on to talk about, uh, you're talking about Malcolm Gladwell talking about Paul Simon. He says, Simon's memory is prodigious. There were thousands of songs in his head and thousands more bits of songs, components which appeared to have been broken down and stacked like cordwood in his imagination. For Simon, songwriting is the rearrangement and reconstruction of those pleasurable sounds. I think this is you, whether you write screenplays or emails, design sneakers or PowerPoints, arrange music or spreadsheets. You create things. You use your brain to bring things into existence. To bring things into existence, your brain rearranges and reconstructs the material available to it. And then you, you, you say in that piece, I think he also is talking about LeBron James, maybe it's like the famous story about LeBron James remembering 7 minutes of a play. Like most of us don't have this LeBron James or Paul Simon crazy memory. And as a result, we have to cultivate an external memory. Can you talk about kind of at a very high level, maybe what you've learned about and how you think about doing that in your process?

I adopted adapted Ryan Holiday's note card system, which he learned from Robert Greene. And it's just literally boxes of 4x6 note cards. And on those 4x6 note cards are Ryan— I've never seen Robert's actual cards, but I have seen Ryan's and His are filled with kind of shorthands and maybe a phrase or a word or a single sentence that conveys a story from some book. So just little kind of like reminders and capturing like the broad strokes of something, knowing that You notate it with like, on this, in this book, on this page. So you can go back and find the specific details.

Right. It's a, they're little prompts almost.

They're little prompts.

Clues.

Clues. Yes. Um, glue on a piece of paper.

Yeah.

It's a, it's a physical clue. And then Ryan and Robert, they file them in boxes, which are broken into themes or categories, or if the box is specific for a book, it's like there's chapter sections and then the cards are all of the material for that chapter. So I do a version of that. My, my note cards, I found it was just hard if I did the shorthand of a word or a phrase, I would just a couple weeks later when I'm looking at that card, be like, what was I wanting to remember about this? I don't. I don't remember the context.

By the way, implicit, I think, in all of this is that our memories are way worse than we think they are.

Yes.

Terrible.

Yeah. So I try to add, like, the necessary context of if it's a quote, it's like it's sandwiched between some context leading into the quote, the way it might appear in a piece of writing. And yeah, and then they're just, they go in. I have 5 or 6 different boxes that are filled with cards. And usually it's like when I'm reading it, when I come across a story in a, in a book, I'm like, oh, this is perfect for this section of note cards that already exists. And so I make a note about it and then I put it in that section. But it also happens where I can't think of like where this would belong. And one of when I was first starting the system, The mistake, or for me it was a mistake of if I didn't know exactly where it went, I would just kind of like not make the note card and just leave it.

It doesn't have a place.

It doesn't have a place. Like now I have in each of the boxes, there's a section at the front that just says waiting room. Cool. And so card will go there and then it's waiting.

It's a seed waiting to grow.

A seed.

Yes.

And then a couple of weeks later, I might read something. It's like, oh, this is like that story in the waiting room. And then those two cards become a section.

Yes.

And then once a section kind of fills out and there's like 15 or 20 cards, that's kind of my cue. There's something here.

It's almost bubbling up.

It's bubbling up. Yeah, yeah, yeah. And there's just like, I've got a lot on this.

Cool.

Let's, let's figure out how these pieces fit together. And that the writing is like pretty more or less like fitting those Lego pieces together.

Yeah. Well, and it, it, For anyone who's read your writing, it's very clear and you've talked about this, how obviously your writing is just the exhaust of this process. Like it's just the most totally obvious, um, export of, of what you're doing.

Yes. Yeah. I'm totally reliant and yeah, it's all of my output is just a function of the inputs.

Yes.

For better or worse, like I, um, I personally, I do identify and feel more like a reader researcher. And the writing is kind of like, here's some cool things I found. Does anyone else think they're cool? You know, it's the writing is just the urge to like these stories I read about that I love. Like, will anyone else?

Yeah. It's the bubble up. It's the exhaust.

Yeah.

There's an idea that you started to talk about a little bit, which is sort of this communicating with your past and future self in a way, like what this external brain is doing there. You were talking about Nicholas Luhmann, who created the Zettelkasten method. This is him. One of the most basic presuppositions of communication is that the partners can mutually surprise each other, which is awesome.

Yeah.

Especially when you're talking about the partners being yourself. There are two ways you— I know that you think about this sort of like forward communication or future communication. One is your, like, questions in the margin, and then the other is like your codes or you're like less than, equal sign, greater sign.

Oh yeah.

Can you talk about like how you think about those two constructs and like how they enable you to communicate with your future self?

Yeah. So the Luhmann, Niklas Luhmann, he also has another great thing about making notes for an ignorant stranger.

Wow.

Because that's what you are when you come back to it. And like we were saying about art, we think like, there's no way I'm gonna forget this story. You come back to it and it's like, blank. It's, it's like highlighted and underlined. You're like, what was I loving about this? So the note cards are, I try to make them for an ignorant stranger. Like you should be able to pick one up and. Have enough context to make out what, what this thing is. And so in a similar way, in the margins of books, I try to, to do that for myself. Even if it's like, on the page before, he mentioned— for specific, I'm reading this biography of Mike Nichols right now, and a critical or like collaborator in his life was this woman Elaine May. So Elaine May is introduced on page 34, let's say. And on 35, it'll say, it won't mention Elaine May, it will say she. And I'll make a note that'll say, see page before. In the moment, it feels ridiculous.

You're adding little affordances. You're, you're taking the burden of understanding and context in the present when most of us do it in the future. We say, oh, they'll figure it out.

Yeah. In the moment, it feels ridiculous. Like, this happened 3 paragraphs ago.

Yes.

But when I come back, when I finish that book and I go back through it, and this page is dog-eared and it says she, I'm gonna, I'm not gonna remember that it was the very page before. So I do a lot of like notation of.

And by the way, you can imagine that's like obviously pretty simple one, but I'm sure there are all different kinds of ones that were, it's actually like a little bit more of a complex context.

Yeah.

That it's so nice to have when you go back.

Yes.

That like wouldn't be even— you couldn't even just turn to the page before.

Yeah. Yeah. So I do do stuff like the questions in the margin. Another specific example, I'm reading the journals of Eugene Delacroix. It was recommended to me by Henrik Carlsen, who I loved your conversation with him and I sent him after, after listening to that, I hadn't met Henrik or we hadn't like communicated before, but he said something that made me think of this thing from a book and I sent it to him and then he was like, oh, you should read the Eugene Delacroix journal. So I'm reading that right now.

Who is Eugene?

He was a French painter.

Cool.

And so this morning I read this line where he said artists are driven not by new ideas, but by the obsession that what has already been said is still not enough. So in the margin, I'll say, what are artists driven by? Something like that. So that when I'm going back through the book, I'll see that and it'll quickly remind me of like why I liked that. Because it's like I sometimes think like a lot of what I'm, I'm writing is like things that have already been said, you know? Yeah. Um, and it was like, that's okay.

Yes.

According to Eugene, you know, you're giving yourself like little alley-oops.

It's just like, you're making it so easy to come back and resume the, yeah, what, what kind of was electrifying. Yeah.

Yeah.

It's cool. And then the other, yeah, the other thing you do is these, it seems to me very similar to the Christopher Alexander idea of like patterns. Um, but this idea of like you have these phrases that have compressed some latent kind of set of ideas that you're, you're putting on note cards and writing in the margins of books and things.

Yes. Yeah. So the less than, equal sign, greater than sign is something I'll, I'll write in the margin, which means this text that the corresponding, the text next to that sign reminds me of blank.

This idea.

Yes. So I'm trying to think if I can think of a specific example. There's a thing in the Mike Nichols biography where he says, we don't know what things are. Big things often turn out to be little things and little things don't walk around with a sign that say, quote, this is a big thing. So I might read a story where it's like a small, a little thing became a big thing. And I'll write in the margin, less than sign, equal sign, greater than sign, little thing became big thing.

Is that usually how they come? You're usually taking them from some original source that has a version of this phrase and you're turning that phrase into almost a bucket for future ideas.

Yeah, it's like that, that example of Mike Nichols, when I read that, I was like, I can think of a million examples of things I've read where little inconsequential things became very important.

Yes.

And it's like, I love, I love this articulation of it and this like idea of it. They don't wear a sign.

Yes.

That says this is a big thing.

It's a personal meme in a way.

Yeah, totally. Yeah.

And I've done this a little bit and it's a really lovely way to like a simple example and certainly something that it's part of what we were just talking about is Steph Ongo, who creates this software Obsidian, I've interviewed him for the podcast and he has this little essay called, I think it's called Stadium of Selves. And it's about this idea of past and future selves. And every day you're getting up on stage, today's version of you is performing or like on stage in front of all of the past yous and future yous. And it's like, today's your chance to do something for the rest of you. And I've started to like, anytime I come across that idea of Hendrix, the third chair, as an example, I was just thinking of that. Like I tag it Stadium of Selves or Audience of Selves. And it's like, it's a really wonderful way to sort of improve your memory. Because if it's just trying to remember the individual isolated instances, it's like, good luck. But instead I'm compounding this like bigger idea that's like growing in my mind.

Well, it's interesting when you said it's like a meme, it kind of made me think the reason I remembered the Nichols quote, I'm pretty sure that was word for word, was I first thought little thing became big thing, which is like my shorthand now for it.

It's your clue.

It's the clue. And then I work backwards from that because now I've like, I put that in, in a few different places of where stories were like, and this happens a lot where a note card about a story, it goes in one section. And now I just learned this Mike Nichols thing. I was like, actually, that story is better over here. So like, I've been re- shuffling things around, making that section of like, it's not wearing a sign that says this is a big thing, but it— my memory was first that like little shorthand of it, and then the quote was like in there too, you know.

It's really cool. One kind of last part of this I think is creating space for things to grow and expand and linger or be idle. Uh, there's a quote from Robert Persig: if a plant only gets sunlight, it's very harmful. It needs darkness too. In the darkness, it converts oxygen into carbon dioxide. We are like that too. We need periods of doing and periods of non-doing. You've talked about putting a book aside, but more broadly, I'm curious how you think about sort of like creating idle time so that actually time can be that filter and that you can sort of like, I don't know, these things can sort of like bake in the oven.

Yeah. Yeah, it made me think of a couple of things. First, I'm, whenever I see someone say, I was reading this morning about, I'm like, immediately I'm out.

You know? That's hilarious.

I'm like, yeah, you were reading this this morning.

Oh, I'm guilty of that.

Um, and I just think, yeah, you just need more time to, you need to spend more time. Because the other thing that happens all the time with the note card system, which most of those cards are coming from, from books, and when I'm reading the book, I'm dog-earing pages. And then when I make the note cards, I'm going back through the book and there might be 100 pages dog-eared and only 10 note cards.

So it's a double filter.

Double filter. And so my, one of my takeaways from that is like often the attraction is just the novelty on the initial read. Letting time pass and if it still excites you on the second time through is just like a better, because, because often it's like those pages that were dog-eared that don't become note cards. It was just like, I hadn't heard this put this way before. It was interesting, but like, there's not really anything there. And so, yeah, when I see like, yesterday I read this great story, it's like, it needs more time to be determined if it was a great story, I believe. And so I'm a big believer in, in time as a filter. And then the Persig thing of doing and non-doing. There's, there's another great, uh, concept I love from this woman, Nanty Andreesen. Yes. She's a neuroscientist who, when she was coming out of school, most of the experiments for creativity were designed to, to be a control group where it was like, the people sit on a couch and do nothing. And like, they're, you know, they're using like brain imaging machines. And then they have like the experimental group do some puzzles or math problems or some sort of creative like task to see like what parts of the brain are lighting up when they're doing it. And she was going to, like, design her first study. And it was just this, like, baked-in assumption that the control group was always, like, people doing nothing. And then she— and Dreesen was like, when I sit on a couch and close my eyes, like, my mind is, like, firing, you know? I come up with so many ideas.

Yeah, nothing in quotes. Yes.

So she was the first, like, let's actually test that, uh, you know. And so, so she developed— or her finding from that study was like, when you're sitting doing nothing, like you're actually using some of the most creative parts of your brain.

Shower thoughts.

Shower thoughts. Like when you're sitting in bed before falling asleep.

I often call this letting the snow globe settle.

Oh, it's like that.

And what I'm implying there is a level of clarity. But it's like, yeah, if I'm shaking the snow globe, I don't actually get to like see what's going on in there. And then when I see that, it's like, oh, actually there's so much more here than I thought.

Yeah, yeah, yeah, yeah. So she, she coined this term REST, an acronym for Random Episodic Silent Thinking, which is just like a bunch of fancy words for like what your brain's doing when you're not having any inputs coming in. You're just, you know, you could be on a walk and if you're not listening to a podcast, it's like random episodic silent thinking is like what your brain is just naturally doing and And when it's doing that, like her brain imaging, it's not like lighting up, but it's like it's making connections, like parts of the brain are connecting things. So ever since learning about that, I, I like try to carve out time for that every day.

Yeah. Yeah. It doesn't just increasingly in our modern world, it doesn't happen by accident. No.

And it's, I mean, it's really hard. 'Cause I do love like clue hunting, you know, it's like, I'm just gonna sit here and do nothing. Like I could be reading, I could be listening to a podcast on this walk, or I could have a speaker in the sauna and listen to a podcast or whatever it is. So I, I try to do like a half hour of just like nothing, just sitting and let it like, and not having like pressure on like something has to come up here.

Yes. But it's more of a curiosity of like, let's see what am I going to find here. Yeah, you might. Yeah, yeah, yeah. I have a friend who, uh, he's wonderful and he's brilliant, but very on, on his phone. And he created this thing where he basically has to sit on the couch and his phone is not there and he has to sit there for an hour and he calls it the itching hour. And I was like, dude, you just invented meditation.

Yes. Right.

Yes.

It's essentially. It's very— yeah, the, the random episodic silent thinking is basically like what you do if you sit down. That's another kind of interesting thing of— I, I like tried meditating and it— I just like could— I don't know, I couldn't— it just didn't stick for some reason. And this like 30-minute rest session that I do most days is basically a form of meditation, but I because I think of it differently.

It's a different set of rules.

Yeah. Um, which I don't really know what to make of that, but it's just like an interesting phenomenon of how, like, you haven't had meditation work, like, rethink it as totally something else. Um, totally. But yeah, that's often where in those rest sessions, like, things are bubbling up and I'm making connections. Often I'll do it on like Saturday, Saturday morning. I'll do like an hour of like 20 minutes in the sauna, 15 minutes out, 20 minutes in. And in that case, I am kind of like, let's see if anything surfaces that will be the newsletter theme tomorrow. You have maybe a slight intention, slight intention, and it often happens when I'm like, oh yeah, I have been like thinking about these 3 different things pretty regularly in the last couple of weeks. Like there's something here. Yes. Yes. And I still am like, man, I'd rather just like read or have a podcast. So it's, it's definitely like a difficult thing to carve out.

I think increasingly for all of us. There's a line in an interview you did where you observed that you sort of authentically actually get more dopamine from making connections in your research than like the dopamine you get on Twitter or in the newsletter from sharing them. Mm-hmm. Which feels, and I'm sure that's not always the case, but I think broadly that feels like very you. And it's representative of an idea that you're writing a book about, which is called The Work Is the Win. Um, you've been working on this for a few years. To start, maybe can you give us a one-sentence thesis for what it's about?

It's supposed to be about, uh, the book is about finding, doing things for their, their own sake rather than the fruits of that work or that effort. I'm reading, um, I got a bunch of different translations of the Bhagavad Gita. Okay. And one line that I'd seen, like, reference related to that book was something along the lines of, you have the right to action, not the fruit of that action. And so, wow. And the reason I got a bunch of different translations is like, for the introductions where different scholars or people who have had like a lifelong love of, in this case, the Bhagavad Gita and spent like tons of time trying to understand this text are detailing like the core themes, the core ideas, the impact it's had on people. So I've been interested in like that with this, with this book. In one of the translations, the writer of the, of the introduction used the wording, being utterly dedicated and utterly detached. And that felt to me like a pretty good—

wow—

forwarded summation of this book. It's like being utterly dedicated to what you're doing, detached from outcomes and rewards and status, prestige, expectations. Not to like, not to try to talk someone out of like wanting those things, because I do think scientists, for instance, like to be able to fund their research, like you need to like win grants and like some of those things are important to like being able to be utterly dedicated.

Yeah, any creative person or anyone almost doing anything, you can't tune out the market, right? You can't tune out the audience entirely, right?

Yes. Yes. So it's like acknowledging that, like, those things are— can be good and helpful and useful. And it's like— and the best way to get them is through this, like, approach to work.

You've talked about going immediately to the boring aspects of things. Comedians make money during the day and collect it at night. The coffee beans procedure. Robert Greene says to see if you enjoy what others find tedious. Can you talk about why that kind of like sinking into the monotony of something is so important to this?

That the get to boring, that phrasing came from Ben Gibbard, who's a musician, and he was talking about he was divorced and was asked about like, when did you know the relationship like fell apart? And he said he was like, he didn't have any regrets, but like, he realized they didn't get to boring in their relationship.

Whoa.

Before they got married.

Whoa, whoa, whoa, whoa.

Like, it was very exciting, the spark of like a new relationship. And they like quickly got married and like never like spent that time of just like sitting on the couch for a weekend, not doing much or like going grocery shopping together. And it struck me as like a good— not, not only like a way to find like relational compatibility, but like work compatibility. Yeah. Like get to the boring aspect.

You're going to spend your days doing this, your days and hours and weeks and years.

Yeah.

Ongoing long after the sexy part fades away.

Yeah. So the coffee bean procedure, is sort of related to that. Um, that comes from a, a writer named Adam Mastriani, and he was talking about how, like, he often hears from people that are unhappy in their work lives. And he said when he asked them what they think they'd rather be doing, like, they say something like, oh, I'd rather— I really would love to run a little coffee shop. And, and he was like, if I'm feeling mischievous that day, I'll ask them, what coffee beans would you use? And if that's a stumper, like, what espresso machines would you buy? Would you bake the goods in-house or have them, you know, a third party drop them off every morning? What point of sale software will you use? Like getting to break— breaking down the fantasy of, of running a coffee shop into like its day-to-day component parts.

Yes.

And like not that you have to have an answer to those things, but like, would getting— would finding out the answer to those questions, does that seem interesting to you? Because if not, like, that's— you're not going to like being a coffee shop owner because your day will be filled with that. So getting down to the boring day-to-day tediousness. So like for me, maybe the— on the surface, outside looking in, it's like the publishing and having pieces like be read or retweeted or whatever it may be.

Like, you have some pretty viral Twitter posts.

Yeah. So if you're like somebody that's thinking about wanting to be like a writer, like that looks cool to like have that.

Having published a book, sick.

Yes. Yeah. But like getting to the how I actually spend my time is what the person should like and see, because it would look very boring and like it's more or less the same few things I do like repeatedly day after day that I would imagine would be— get pretty monotonous and frustrating if you, if you don't really like doing those things. So getting to boring is just like, I think can apply to most like, you know, an NFL player they play 16 games a year. Like, what are they doing the other 350 whatever days? Yeah. Do you want to do those things?

Yes. Yes. Yeah. The other example I gave is in the comedians context is, is Seinfeld and somebody talking about making money during the day and collecting at night. The same exact idea of Kobe in the, in the gym at 4 AM shooting free throws. We all see the end product and we're like, oh, that looks good.

Yes. Yeah, that, that is Seinfeld and Chris Rock.

Cool. Oh yeah. Such a amazing one. Um, maybe kind of almost inverted version of this is the idea of being great regardless. You talked about, um, I think it's talking about Mayer and then talked about Harry Belafonte, the previously actor and then singer, where you're actually in the inverse situation where you're sort of doing something that you don't want to be doing. and it kind of isn't the end goal, but taking it radically seriously anyway.

Yeah. Yeah. Mayer's thing is like, just ace it for fun. Like it's, it's, and he was talking about, he was a, he worked at a gas station when he was in high school and like still his dream, like he knew early on he wanted to be a musician and there was some, it was hard to know that like, this is the thing I really want to be doing and like, being in school and that disconnect of like, no, I know, like he used the analogy of when you go to a restaurant and you know exactly what you want and the waiter's going on and on about the specials.

Give me a head— yeah, yeah, skip ahead.

I know what I want. Yeah, I want the burger. I don't want to like hear like that the lobster is cooked and put back in the shell. And so he had that like frustration, but he was like, that said, be great at whatever you're doing on the way to where you're trying to go. It's more— it's more fun to ace it than to be sitting around thinking about like, this isn't what I want to— what I really want to be doing.

And you're here anyway, by the way.

Yeah. And I just like that idea of like the things that we don't necessarily want to do. And it's also like the Belafonte story. I like that example because you just like don't know when you take something seriously, like who's going to see it and like what opportunities are going to come along. So he's like, wanting to be an actor, and this is in like the '40s and/or '50s, so there just weren't opportunities for Black actors. And he's going on auditions and everyone's like, we don't have a part. And then he goes to one and it's, uh, they're staging John Steinbeck's Of Mice and Men, I think. Um, and there's no— again, there's no part for him, but for whatever reason, the director takes a liking to him and he invents this role for him, which is like singing between set changes to give the stagehands more time. And you can imagine like being in that situation where it's like, I want to be an actor, not a singer.

This is— yeah, this is totally in serious—

the crowd's not even listening to me. It's changed. Like, they're talking amongst themselves as I'm up here singing. And like, this has nothing to do with the play. But he like he went out there and he was, he was like, the story I told myself was like, these songs are essential to knowing like the time period that we're talking about here.

And, and he went out and was just like, I'm going to act as a singer.

Yeah. I'm not, I'm not a singer. I'm an, I'm acting as a singer. Um, so he just like approached it that way. And then one night there's a few jazz men from a local like jazz club came down the street to watch the play one night. And they didn't think much of the play, but they're blown away by Belafonte's singing. And they, they stay after and like, you got to come sing at the— I think it was called the, the Roost or the Rooster or something. Um, it's like, no, I'm not, I'm not a singer. What you saw me do was acting. And like, no, you're a great dude, whatever. Yeah. And they— so they introduced him to the manager at the Roost and he starts doing Again, it was like a between when one band's breaking down and another band setting up. He was like singing to like keep the crowd entertained and then he's elevated into like he's a regular. And then he goes on this like one night they're recording the, the live set and like it's, it's ran on some radio station and like a label exec hears it and he signs with this label. And he just goes on this like legendary— he has a legendary career in music. And it starts with like taking seriously this random acting role that if he hadn't like approached it that way and just was like, you know, not taking it seriously on the night of those jazz guys coming in and like they didn't bring him over to the club, like his career wouldn't have happened.

The dots connect in reverse.

Yes, totally.

You have a thing where you're writing about Ira Glass and his producer Alex Spiegel and the time it takes to get good at things. The quote is, wow, there's no sign that you have any talent for it. This is her, excuse me, Alex is talking to Ira after hearing some of his earlier work. Yeah. Wow, there's no sign that you have any talent for radio. Like, there's no sign that you're going to make it. There's just nothing good in here. This is Glass. Not only was she right, Glass said, but he revisited other episodes from his archives and was struck by how even in his mid-30s, 15 years into his career, there was still hardly any sign that he had any talent for radio. Lewis laughs and says, I think we share this quality in that neither you— this is Michael Lewis— I think we share this quality in that neither you nor I cared all that much if there was a sign that you were going to make it. You were just going to do it anyway. Yes, that's very true, Glass replies. Yes, I like doing it, and I was just going to keep going. He was just going to keep following up. And then one more, André Gide. I have never produced anything good except by a long succession of slight efforts. No one has more deeply meditated or better understood than I Buffon's remark about patience. Genius is but a greater aptitude for patience. I guess I wonder, like, this sits a little bit in contrast to the idea that, like, we enjoy the things we're good at, or at least we enjoy the things we're improving at. So I'm curious how, for you, like, how do you think about just purely focusing on the inputs versus, like, actually experiencing the ramp up and improvement and taking stock of, like, getting better at things? Like, clearly there's some value to being aware of, like, what the market's telling you about what you're doing and these types of things.

Yeah. Yeah, I do think there's like, you should at some point start to get a little bit of feedback that it's what you're doing is working or resonating or you're improving.

And I'm sure Ezra, or she mean Ira, was on some level like, yeah, clearly wasn't terrible. He kept the job, right? It's the funny part is she's reflecting on the Ira Glass of today who's a master.

Yes, right. Yeah. So there's probably something of just like maybe it's overstating a little bit of like how bad it was in the moment because he's still like, you know, in the industry working in radio. It couldn't have been so bad that no one would give him a job. But I— so maybe, maybe more striking was just like the gap between Ira Glass today and how good he is versus like and how long it took to get there. But I do— I remember when I was about a year and a half into working with Ryan, I was getting— I was, I was getting frustrated by the gap. We kind of were working in like Google Docs where he would be drafting articles or Daily Stoic emails or whatever. And I could be in the document and see him writing. And to see him just kind of write without like breaking his flow of— it was as if he was transcribing something already in existence, but it was just like coming right out of him.

Wow.

And how quickly and like the quality of what he was writing. And so I could see that and then I would go sit down and try to write. And I was like very aware of the gap between what I just saw him do and what I was able to do.

Totally.

And I was really frustrated by it. And I was like, at that time I had been— I had read a lot of the stuff about like, you know, early inclinations being a clue to like what you should do in your professional life and like early aptitude being a signal of like, this is what you're meant for. So I was like, maybe this, this doesn't seem to be it because it's like I'm a year and a half in and it's not working. I remember having a conversation with my dad where I was like, I was thinking about quitting and just like going into a different line of work. And he was like, how long has Ryan been writing? And I was like, I don't know, 15 years. And he's like, how long have you been writing? And I was like, a year, year and a half. And he was like, imagine— I played lacrosse in college. He's like, imagine if a kid that just picked up a lacrosse stick came to one of your practices and compared himself to you on the field. Wouldn't that be a little ridiculous? And it just like immediately landed for me of like, yeah, that is absurd. I didn't— it's— it'd be weirder if I was like on his level, you know? So I just like sort of want to, like a lot of my attraction to those stories is trying to like tear down this idea of aptitude and ability and having that happen quickly being a sign that like to keep going. And I love stories where it just, it took longer. Than most people are giving themselves to see if there's anything there. And like, just your attraction and your like level of engagement is enough, like for a while. Like it doesn't have to— you don't have to get great, but if it's engaging, like just keep following it.

Yes. Maybe the inverse of this. One of my favorite things you've sent me is Tennessee Williams' The Cast— Catastrophe of Success.

Yeah.

Speaking of, of like the patterns, you, you wrote in the margin of this one, a sword cutting daisies. I'll read the excerpt. It's amazing. This is an oversimplification. One does not escape that easily from the seduction of the effeté way of life. You cannot arbitrarily say to yourself, I will not continue my life as it was before this thing. Success happened to me. But once you fully apprehend the vacuity of a life without struggle, you are equipped with the basic means of salvation. Once you know this is true, that the heart of man, his body, and his brain are forged in a white-hot furnace for the purpose of conflict, the struggle of creation, and that with the conflict removed, the man is a sword cutting daisies, that not privation but luxury is the wolf at the door— which you also wrote in the margin— and that the fangs of this wolf are all the little vanities and conceits and laxities that success is heir to. Why then, with this knowledge, you are at least in a position of knowing where danger lies. Oh my gosh. Good writing is special. Maybe from the perspective— I mean, obviously you've come a long way yourself. You've also worked with some real masters, whether that be Ryan or Robert Greene or Rick or others. How do people who really have kind of ascended— Ryan's written whatever we were talking about last night, 15 books, 19 books. How do people who've reached success fend off the wolf at the door?

Just by keep doing the thing. Um, yeah, Tennessee Williams, he's writing about when he was coming up as a playwright, he, you know, it was like one of those stories of just like he worked odd jobs making minimum wage and writing in the margins of the day. And he had a play, I think, A Streetcar Named Desire, that was like a Hamilton-type success of its time. And then suddenly, like, everyone was wanting to do things for him. He's staying at a hotel and like everyone's waiting on him hand and foot and, and realizing that like the the effort that his previous life required was essential.

And by the way, without constraint— constraints are powerful, man.

Yeah, the constraints thing. You mentioned that Andre Gide quote about the series of slight efforts and like no one has lived that patience, quote. The way he has. He has this other line. He was talking about the importance of constraints in creative work and the way we romanticize like a life of complete freedom to do whatever we want to do whenever we want to do it. But he's like, like Kant's dove without the wind's resistance, The wings can't soar, something like that.

Yes.

Um, and I didn't know what he meant by Kant's dove, which was a reference to Immanuel Kant, his Critique of Pure Reason. He just like uses the metaphor of a dove needing the resistance of the wind to fly. And so I just What I like about the Tennessee Williams, Catastrophe of Success is like, and it's, it ties to like what the, what I'm writing about or thinking about with The Work Is the Wind. And one sort of class of people I hope that book resonates or like finds is just people that are like chasing some finish line. Or this amount of money or this amount of success.

If only then.

Yeah. Like there's a— one of my all-time favorite movies is There Will Be Blood. And Daniel Day-Lewis's character in that movie is this kind of like aggressively greedy, will do anything for money and power. And he goes on this, this chase for those things. And in an interview with Daniel Day-Lewis, he was like talking about his character and he's like, it's really about the false promise of the horizon. And the interviewer's like, false promise, what do you mean? He's like, you get there and of course the world is round. Like the horizon just keeps receding and receding. And I think there's something that Ryan, Robert, Rick all seem to like, for some reason, they still get up and do the work that they do despite like having the luxuries of the financial or social resources to have other people do it or not have to do it at all. But like, why do they still do it? And I think it's like just without like effort and like striving. It's just the sword cutting daisy thing.

Yes. Yeah, it seems to be for those guys a much more internal thing and an internal battle. Ryan talks about reading that The War of Art book before every project. Like there is something, because if it's the external thing, as you say, either the horizon will recede or yeah, it will feel like you're going through the motions. I want to talk next about an idea that I think both of us are fond of, which is a set of ideas we could collapse into what Christopher Alexander calls unfolding.

This is you.

In Making Art or Life, Alexander writes, this is a common source of frustration and misery, thinking that desired end states, the fully formed, beautiful, and coherent work of art, relationship, career, etc. Can be abstractly conceived or predetermined, forgetting or failing to realize that they are products of a, quote, process, a budding, a flowering, unpredictable, unquenchable unfolding. You and I share this affinity to this idea, but yeah, why is this so resonant for you?

Well, I love your metaphor of holding seeds in your hand without ever planting or watering them, trying to figure out what are these going to become before I'm going to plant them in the ground and try to cultivate these seeds. And it was something that tripped me up for a while was to use that metaphor. It was just like holding seeds and wanting to know where is this going to go? And then I'll maybe commit to it. And I just see it with Tripp. I just see it tripping up a lot of people of sitting around and thinking and wanting to know with certainty Is this job going to lead to something? Should I or should I not go to the social event? Like wanting the certainty of the payoff and the outcome and letting that determine whether or not you're going to do this or that. So that, that's part of it. And then also just like having it happen enough times where like a lot of the best things that now are in my life, like it would have been absurd for me to like, okay, this seed here is gonna, you know, um, yeah, we were talking earlier.

Exactly.

Yeah. And so I just think it's just like, so just like one of those like absolute kind of truths of like things just unfold and the time spent trying to predetermine is just creates a lot of misery.

Yeah, you have a metaphor. You were talking about advice Ryan gave you about you're trying to plan out the full 9 innings, just throw the first pitch. It feels very, very similar. I'd like to talk a bit about maybe the thing downstream of this idea, if you really internalize it, which is actually taking initiative to do things. A set of quotes, one of them that resonates with one of the things you just said, which is Robert Greene on certainty. He says, the need for certainty is the greatest disease the mind faces. This is you on Hannah Arendt. Hannah Arendt identifies in The Human Condition as the core trait inherent in all human activities. Everything that happens in this world, she writes, rests on initiative, on those willing to take the burden, the toil and trouble of life upon themselves. And then I have two more quotes. David Mamet was asked the advice he most often gives. Differentiate yourself, he said. When he auditions actors, he He said after the third person, he can't remember the first person. So he tells actors to make themselves memorable, to throw some interesting jobs on their resume. No one takes his advice. He said, actors don't want to do this. They think we have to do things by the book, but there isn't any book. And then finally, this is Jordan Peterson on Rogan. You don't want to oversimplify things, but once you've made a decision, well, That's when it's necessary to put doubts behind you because otherwise you just act in half measures. One thing I see a lot of, I'll see a lot of is this confusion about acting. Quote, I don't know what to do, so what should I do? Well, nothing. I'll wait around until I figure out what to do. This is Jordan again. No, you should put together a bad plan and you should implement it because even if you fail in the implementation, you gather information and then you can rectify the plan. Staying in that malaise until you know what to do makes you get older and more miserable, and you've gathered no information along the way. A bad plan is a good idea. Any plan is better than none. That's a good rule of thumb. A bad plan can be incrementally improved with experience. He who hesitates is lost.

Whoa. Did I use that? Yeah. Really?

You said that to me.

I did. Wow.

Where do we get initiative? How do we improve on our ability to take initiative?

I think it— I mean, what's coming to mind is just sort of what we're, we're talking about is I think a lot of people have like a sense of what they would like to take initiative on and then they're, they're blocked or delayed by just like wanting to do the, the pre-calculation of like, how is this step going to lead to that step? Um, somebody sent me a quote the other day from E.B. White that was like, the world is immensely complex because of course one thing always leads to the next. And it's just like when you, when you think about like one thing leading to the next, leading to like when you just like kind of do that thought exercise, it's just like of course you can't know, you know. Yeah, it's a fantasy. Yeah. And so I think the initiative, a big part is just like suspending the need to know. And I think you and I have talked about the, in the context of the make contact with reality, because reality has a lot of nuance and a lot of information and feedback.

Yes, this is our friend Henrik's amazing frame.

Yeah. Yeah. So letting go of the need to know how things are going to unfold goes a long way into like, because again, I just think like everyone has a sense of like what they would like to take that first step on or whatever, if it's like a creative project or some like vague interest they've always wanted to do, like the initiative is just like, just go and let go of where it's going to go.

Do you remember why or how or what caused you— like what the almost the emotion was when you first reached out to Ryan? That was a pretty amazing gift from past you to current you.

Yeah, I don't— I think it was just— I mean, the, the subject line of that email was something like, just some words of admiration or something. And it like truly was just like the impulse of being a fan of his work and having it, reading it. I think I found his books at a time when they were really helpful to me and they had like tangible impact on my life. And so I think the impulse was just like pure fandom slash like appreciation.

But you were, you were on some level, you were uninhibited, which maybe goes back to the beginning of the way you answer that question, which is actually like a lot of times we know how we feel about things.

Yeah.

Or even we know what we need to do.

Yeah.

But we're like, ah, with all these reasons, I don't know if I write him an email, he probably won't respond.

Yeah. Yeah. There's all, all sorts of like mind games that like could have talked me out of it. And again, like I was saying, having it happen enough times where like, I couldn't have possibly held a seed in my hand and known like, should I send this email? Like, I think this is how the seed's going to blossom. Like, there was no considerations in that moment of like wanting something out of the email. And and it wasn't— his reply was just like, honored to hear my work has been helpful. It wasn't like an immediate like, yes, yes, you are, you are now my apprentice. Congratulations. It was like that. I sent him that email and then like a couple of months later sent him another one. And then just like over time it evolved.

And a lot of times initial initiative though can it sort of breaks the dam a little bit. It almost breaks the emotional dam we have. Like, oh, cool, I can— he responded, great. I'll send him a future email if there's something that bubbles up. And like, yeah, now you start to— you get a little downhill.

Yes. Yeah. And it makes me think of the— that Mike Nichols thing we were talking about, like, little things don't carry around signs that say this is a big thing. Like, it didn't feel like this is gonna, this is gonna make or break. Yeah, it felt in the moment like that, just a little thanks for like the work that you do.

Hmm. A part of this I think is a kind of courage. You have a newsletter you wrote where you're, it's ultimately kind of about this John Mayer clip, but in one part of it you're talking about Huberman. There's this clip where he's talking about sort of like getting out of the sewage before you get to the clear water.

Oh yeah.

Every morning when I sit down to read and again, when I begin to work, I say to myself, accept the initial agitation. Essentially, you become creative by creating. You get more creative the more you create. And then John, you gotta keep forcing it, forcing it, forcing it. You gotta get fearless, fearless, fearless, fearless. In this clip, he's sort of like Ouija boarding the like the famous Zane Lowe kind of like just like ripping the song out of nowhere. And he uses this phrase, stupid bravery.

Yeah.

How do you practice stupid bravery?

Stupid bravery. Yeah, I do love that. Again, it's coming to mind just like the detachment from the stupidity is like, like in the context of Mayer, it's like the bravery of his thing about Ouija boarding is just like when he, when he's trying to work on songs and he like doesn't have a lyric, he allows himself to just like say nonsense. Like it doesn't need to make sense. Just like let things come out of your mouth.

Yes.

And the stupid part of that is like you are going to say stupid things. Or in my case, like some of the writing of, of like the cliché of first draft of everything is terrible, like allowing yourself for it to be terrible. Yes. Yeah.

You got to write a bunch of bad stuff to get to the good stuff.

Yeah, yeah, yeah. Yeah. Huberman's like, you got to wade through some sewage to get the clear water. And yeah, I think that this stupid bravery is, is just like allowing yourself to be bad and say dumb things on the way to it becoming like better and better. And I still struggle with this because one of the hangups on the book has just been like wanting to know, like before I write a chapter, like wanting, wanting it to be like in my head, knowing that certainty. Yes. And it's, and it's related to like now since reading Henrik's piece about unfolding and like having that articulation of it, has been helpful to like let the writing process unfold, start like, let it be bad and trust that like, that that's getting you to places like, again, you can't predetermine it. And it also happens all the time where it's like in the flow of saying terrible things, it's like, ooh, I didn't know that phrase was in there. You know, I didn't know that. And then you get something and then you follow that thread and But you couldn't have gotten that phrase without the stupid bravery of like letting it be stupid for a little bit. Yeah.

Seinfeld has this frame about like almost creating like two different versions of yourself for your writing, like the editor and the writer, the reader/editor and the writer are like two very different demeanors. Yes. And like at first you actually have this, have this, have to have this like gentle, accommodating, like great job. You're wow. Like you're doing so beautiful. And then by the way, the mean editor can come over the top, but it's Well, I think for so many of us, it's really hard to say. I noticed I did this thing where I wrote, I wrote like 30,000 words in a month. I wrote like 1,000 words a day. And I often tell people like the hardest thing every day was figuring out what to write about. It was, it was getting the first 100 words. Cause if I get 100 words, I usually get 1,000 words. And the single best thing to figure out what to write about to get those first 100 words was literally the Ouija boarding. It was sitting down on my keyboard and being like, I am writing and I don't want to be and blah, blah, blah, blah, blah. And just like getting the wheels turning. Yes, it's crazy.

I do morning pages most mornings, like just 3 longhand. It comes from like Julia— are you familiar with it? Okay, so it's just like—

never done it, but I know it well.

The kind of only rule is just like the pen can't stop. And I— what was hard for me about it initially was like not knowing the starting point. And so now I do the same thing every time, which is just like the date, the time of when I'm sitting down to do this, where I am, what I've done so far up to that point.

Describe it.

Describing it like, and then at some point it's like, took a shower, got dressed, filled up my water bottle, made a coffee, sat down, read for a little bit, took out the journal, and here we are. And then it's like, okay, what do you want to journal about? What's on your mind? What do you want to get off your mind? Like, these are literally the questions I ask. And then I'm just like noticing, oh, you're thinking, and I literally will write, oh, you're thinking about this. Let's just observe, explore this.

My friend Peter calls this, he used to do morning pages extensively, and he'd call it unkinking the hose, which is so good. Back to the Huberman thing, right?

Yes.

Yeah.

Yeah.

There you have this line about sort of like you become creative by creating. It's very embedded in this.

Yeah.

It's like the inspiration you need is just on the other side of starting.

Yeah.

Yeah. There's another idea that's kind of related, which I think you sent me this. We were talking about local maximums in the context of Henrik, and you sent me this Steve Jobs, old Steve Jobs video, which is amazing about folklore. He says, you know, throughout the years in business, I found something, which was I'd always ask why you do things. And the answers you inevitably, you inevitably get are, oh, that's just the way it's done. Nobody knows why they do what they do. Nobody thinks about things very deeply in business. That's what I found. So in business, a lot of things are, I call it folklore. They're done because they were done yesterday and the day before. And I think when you sent me that, you sent me another note alongside it saying, interesting to sort of combine this with folklore and inertia stuff. Thinking of it as your current self being a slave to your younger, less knowledgeable, experienced self is pretty jarring.

Oh yeah.

Which is just such a beautiful way to think about like the, the how devastating local maximums can be. It's like I have this image of almost like you're at the top of this sort of local hill and you're just like clinging to whatever you can find up there unless you have to go downhill.

Yeah.

Yeah. I'm curious if there are ways as you reflect like that you've gotten out of personal folklore, like things that you've realized in hindsight you were like really clinging to or that you've observed in others? Like we all have— there's sort of global folklore in industries and the ways that we write. And we also all have these— if we were anyone other than us, it would be easy to get past these things, but we're hanging on to them. Mm-hmm.

Well, I may— it may just be because we were just talking about morning pages, but like I had taken I did that for like 3 years, like very, almost never missed a day in that 3-year period. And then I took, I don't even know why, I just kind of like stopped doing it for, for a while. And then at a point where I was getting stuck on some of the book project stuff and I had sort of like thought You know, it's my first book. So I was like, the process is going to be— this is how I'm going to approach it. And I started doing it that way. And a lot of it's just like from what I've observed in other authors, what seemed to make sense with like my research system. And so I started like just going down this specific process path for the book. And I wish it would have, like, occurred to me sooner. I'm, like, kind of embarrassed at how long it was like, oh, this isn't working, you know.

We all have those stories.

Yeah.

So painful in hindsight. And you see the water and you're just like, oh yeah.

And it's like, for a year I've been, like, stuck and struggling and writing stuff and, like, it's, it's not working. But it never occurred to me to be like, switch up this, the process.

Yes.

Um, so I went back to morning pages because morning pages is what one of the things I like about is just like it facilitates crappy first drafts. It allows for it. And like what we were saying earlier about like approaching something thinking it's you're meditating versus thinking no, you're doing something.

Yeah, totally.

This is like that. It's like I'm doing morning pages, but almost every day something comes up that's like, this is the start of this chapter. And so the folklore of just like, well, this is how I've been doing the process for the last year, like, and not stopping to think like, it doesn't have to be this way. You know, like I arbitrarily decided on this process. Acknowledging and noticing that it's not like working that well and then experimenting with different pieces of process.

I read, or I've been reading this Stripe Press book called The Making of The Prince of Persia, and it's about this video game that was made in the '90s. And it's a truly, I shouldn't say it's completely unique, maybe there are other, but it's a rare It's literally just this guy's journals as he's making the game. He's like 22 to 26. And it's the rare time where you get the process, like, as it actually, like, I'm not gonna say it's unbiased or objective, but it's the process is actually happening rather than this, like, narrativization that's on the other side of success. And it's amazing. One of the things that happens kind of earlier in the book is he like basically ends up spending like a year distracted, like working on a screenplay and you like see it happening in front of you. And at one point he's like, wait, what was I— he like has that realization. Um, but it's, it's a little bit at least like validating to just like see somebody who ended up being really successful in this project. Like just kind of like how that can happen so easily. Like it, you feel such an idiot when it happens, but happens to the best of us, and it's like slow and insidious, and it just sort of—

yeah, yeah. Wow, that's amazing. It reminds me of like the Steven Pressfield, like, resistance idea of like—

I don't know this—

in The War of Art, like, resistance, like capital R resistance, is just like all the various ways in which we do not do the book or the video game we're working on.

Yeah.

And like a form of resistance is like writing a screenplay instead.

Yes. You know? Yeah.

Yeah.

There's a separate meta point, which is like a great way to do really cool things is just like procrastinating something else. Like you might end up actually doing something great, but yeah.

Yeah.

Yeah. I have a fun section where I just love to go through a bunch of people who I think are particular favorites or influences of yours. And maybe some of them, a few kind of ideas. I'll start maybe with the most obvious, which is Ryan Holiday. A couple things I wrote down: all success is a lagging indicator, creativity is a function of the previous work you put in. More broadly, I guess somebody you've spent an immense amount of time with, you know, apprenticed under, I'm curious what most immediately comes or obviously comes to mind when you think about him and his influence on you.

This is always hard because it's like when I think about the things I do on a day-to-day basis, almost all of them have been informed by like observing and seeing, seeing Ryan go about his, his work and his life in a very, by the way, in a very tangible, hands-on, like pragmatic way, not like an ideological way. No, just like that I sit down and read first thing in the morning, that I make note cards, that I see a story in one place and want to find everywhere this— like, that's one of the things Ryan always does is if you read a story told in one Churchill biography, for instance, he's like, I want to find everywhere the story is told and triangulating and following those threads. That I like stop and go for a run in the afternoon. Just very practical, like, habits and routines that were all picked up from either things— at first it was just like I started the no card system because before meeting him I read his article about it, but then getting to see, like, with my own eyes how he goes about his work. And I think one of the interesting things about him is, if not for getting to see him on a day-to-day basis, I would think this, that he's like always at his computer, always reading a book, just because he's so prolific that it seems like he must never leave like his computer. The reality is like he spends a couple hours in the morning and then like he's outside with his kids and he takes them for a walk and then he comes back and works a little more. And then he's like out on the back porch having lunch with his family and then he comes back in and does a little more. And so one of my big takeaways from him is just like consistency day to day and letting— and not being like so— not spending like 20 hours a day killing yourself, but like put in a little— make, makes like— his word is like small contributions. Yes, make small contributions every day. And if you do that over time, like it becomes pretty drastic.

I think talks about this, he's like, the best great writers are not the people who have these crazy days, they're the ones who write every day. Yeah, yeah, a little bit every day.

Yeah. And so he's just like really informed for me of just like small contributions and letting that compound over a long period of time and not like— there's that thing of like the first rule of compounding is not interrupting it unnecessarily. I think he's also done a really good job of like not interrupting his process, not jumping on like this new format that every creator is jumping on or like Yeah, he's just been so consistent for now 15, 20 years that like his output seems insane. But it's like, it's because there's 20 years of those slight efforts, like the key thing of like a series of slight efforts every day.

By the way, you want to understand how this magic trick happened? Like, look at the process, look at the machine.

Like, yeah, again, it's just like, it's, it's so hard to quantify, like, And if I think of like the way I was living, like previous to finding his work and, and then later meeting and working with him, it's just like those two different people.

Another person is Rick Rubin. One, one idea from Rick: I never try to judge an idea based on the description of an idea. Always musically try the idea. Relates to our seed, seed implanting idea a lot. Yeah, anything either on that note or otherwise, anything that, that particularly stands out in the time studying and working with Rick?

One, one interesting thing I've noticed or have like been reflecting on is it's now it's been like something like 2 years that I've been working with him and he not once have we talked about, or has he had me look into something music-related, it's all like, it's all outside. I should say that, like, I see like a very small part of like his universe of what he actually like, what his life actually is. But in my experience, like the things we've worked on and like that he's had me look into and track down, It's been interesting to see just like how diverse and vast those things are and taking the lesson of just like being curious and interested in learning about all different sorts of things. And like they find their way into, in his case, his music stuff or like a book he's working on. Yeah, I just have found that interesting that the sort of genres of of things he's consuming, the clues he's, he's gathering and letting, like, into his process.

What do they say about if you want to kind of produce something unique, you need to have unique influences? What do you love about John Mayer? A frequent mention in the, uh, 666.

I just, yeah, I just, I really, I, I just, I love the way his, like, the way he articulates things, the way he thinks about things. I love in interviews where it's as— it's, it's like a peek into like his brain working in real time. He doesn't have like his greatest hits of like things he wants to talk about. He's like Ouija boarding in his interviews and he's— and like the analogies and the metaphors he uses. I just knew, knew. And it's like he has a sort of comedic ability, like the great— or like my favorite comedians, it's like their, their ability to like articulate something that you walk by every day and they, they articulate in such a way that like, oh yeah, I like that happens all the time. And there's like the humor in that, like, yeah, ability to observe and articulate. Like I find Mayer does that a lot with his use of analogies and metaphors. Yes. And I just, I love his, like, we use the phrase utter dedication. From what I've just read, it's just like his dedication to like studying the craft of music, studying like the greats that came before him. Like he started learning the Grateful Dead catalog, like prior to him like playing for Dead Company, it was just like this instinct of like, I love this music, I want to know it.

By the way, he discovered it like, I think in like 2010, right? He was already way successful.

Yes. Yes. Yeah, exactly. Yeah. So I think those things have just like, from my, what I can tell, he's just like his approach to like his craft I find really admirable. And, and then, yeah, he's just like, oh, ability and like the way his mind works, I find interesting.

Steve Jobs. We were talking about this this morning. Yeah. What do you think makes— you were joking that it's like cliché. It's like, oh, you're going to tell us another Steve Jobs story.

Yeah.

We had a fun conversation about how, like, he's still underrated. What do you admire about him?

He's another just like great communicator, metaphor/analogy user. Um, and I, I, he also just like one of the greats at like making complex things, getting to the essence of what they are. Like we're in that Make Something Wonderful book. He's talking, I think he's in like 1985. So like computers haven't yet like, you know, hit the mass market the way like they're so entrenched in the world today. It was like they were, they were coming, you know, and there was the similar to today of like the fears of AI and like what, what it will mean and what it is. And like Steve Jobs had this great thing about like computers, like we think that they're magical, but they're really just doing a basic series of steps really fast. It'd be as if I were standing here, walked over there, grabbed a bouquet of flowers, came back in the snap of a finger. You would think I was a magician, but really I just did a basic series of steps really fast. I walked over there, grabbed the bouquet, came back, snapped my fingers. And I don't know, I just like always have or often have the experience of him articulating something that like helps me make sense of things or better understand or like become less fearful of technology or whatever it is. So yeah, I think that that's what comes to mind.

Yeah, he's a technologist who really deeply cared for communicating simply, which is, I think, rare amongst anyone. What about Greta Gerwig? This also came out this morning.

I love— yeah, I love, I love Greta Gerwig. Well, we were talking about like the affinity for somebody increasing once you get to know their story a little bit or hear them talk a little bit. Like, this was my experience with, with Greta. Like, I had seen Lady Bird, Little Women, and just like I was a— Lady Bird especially, what was— I just like loved the, the movie itself. And I think that was the, the movie where I was like And I do this a lot where it's just like, who made this? Yeah, let me go pull the thread, read about them. And from what I've read about, like, one of my favorite stories about her is she had this, like, vague sense of wanting to be a director when she was, like, in 7th grade, and she went and tried to direct a school play and got made fun of for being, like, the bossy girl. And so she, she kind of, like, she was so sort of bullied in that experience that she just stuffed down this, this inkling of wanting to direct. And like, and, and not only that, but just like receded into like the background of things to not stand out and expose herself to the possibility of being made fun of again. And so she was like—

pretty amazing too that she literally went on to be an actor, which arguably is more— but there was some version of that for her that was like, this is the thing I can't do.

Yes, but so the acting, yes, that's what I was going to say is like, so instead of directing, it's like, I'll be, I want to be like in this world, I'll act and let people tell me what to do.

Wow.

And so she spends 10 or 15 years just like, Greta Thunberg, by the way, amazing Greta acting performance. Yes. Um, so she spends like the next 10, 15 years, like just stuffing down this like sense that maybe she would want to try this thing. And she tells the story of being at some, like, party. And this, this woman, Sally Potter, was there and who was another filmmaker. And Greta went up and was asking her about acting, and she stopped her and she was like, you want to ask me about directing? And Greta's like, how can you tell? She's like, it's written all over you. You have to do it. You have to.

Whoa.

Yes.

Oh my gosh.

Yeah. And then like, wow, the next— she was like, like, it's great for that to happen, but then, then you gotta— Greta did something about it and she wrote what became—

yes. Um, yeah, the world sometimes slaps you in the face with a, with a hint.

Yeah.

And then you still don't do anything about it.

Yeah, yeah, yeah. Well, yes, she said— she was like, so that happened with Sally Potter, and then another director gave her shoes, and that's like If a director gives you shoes, it's like, you're next.

Wow.

You know? Wow. And so she was like telling that story and the interviewer was like, all these things were happening to you. Like, this doesn't happen to everyone. She's like, well, yes, they were happening, but I was looking for them. And then like, and then she did something about, she wrote Lady Bird and then directed it and So like that inkling, that like beginning attraction to like the movie of Lady Bird, then like learning that about her, I just like so admire her and her career path. And she has another great thing about another aspect of like why she was putting off on directing was like once she got into that world, she's the kind of myth, the mythology around directors is like these big brash personalities and like they've been obsessed with movies and cameras from the time they were, you know, 3 years old. And she, she was like, I didn't— that wasn't me. I wasn't that personality. I wasn't the kid that was obsessed with movies at an early age. So I didn't think I had the personality for it. And then she ultimately like attempts to do this thing. And then in hindsight, she was like, what I learned was like, you're not born with the personality. It's in the making of movies that you develop a certain personality. And, and like we were talking about, the, the idea of like using early inclinations and early, um, ability as like cluing you in, like, is this in your DNA or not, I just think is like a hoax. And it's just like, it's in doing the work that you you develop and like, you don't have to have the Steven Spielberg story of like coming out of the womb, like with all of the signs of being a great director, like you can develop it.

I think it's in that same newsletter about Greta. You, you have an excerpt where you're talking about David White and you said, no one is born with a certain personality hardwired to be a director or radio host or writer, a standup comedian or a gang member. It's like anything else. Where's your follow-up? There's your personality. File next to what David Whyte says. You are harvesting your identity in whatever it is you're dedicating yourself to in the hours of the day. Yeah, it's powerful stuff.

He goes on, he's like, so you should ask, and like, what you're doing in the hours of the day, like, yeah, what are you harvesting? You're hard— like, he's like, it's not a passive process to work. Like, the things you're, you're spending time on are, are working on you. Yeah, yeah.

Yeah. One of, I know, your favorites and mine, Jerry Seinfeld. A few amazing ideas from him. Find the torture you're comfortable with. All comedians are slightly amazed when anything works. Maybe a favorite that I didn't know about until you told me recently, all art is disguising work.

Yeah.

Yeah. What, what, what about any of those or about him?

Yeah. I think kind of like the through line is just like the humanizing like great artists and creators and like just the long, the many years and like the slight efforts that accumulate in like someone like Seinfeld. Um, like the All Art Is Disguising work. Um, he, he was saying that like some other comedian said to him like, your whole act is a tremendous amount of work to make it look casual. And, and again, like, from what I've read and like interviews I've listened to after having been like somebody that was— had watched a lot of his comedy and, um, just, you know, my surface like understanding was just like he had some sort of natural comedic gene. And to learn that, like, no, he's put, like, tons of time and effort and thrown thousands and thousands of jokes away on the way to, like, making it seem like it's easy. Yeah.

Um, yeah, find the torture you're comfortable with. Find this struggle you're comfortable with.

Yeah, yeah. He was saying, like, he was describing kind of like what he does all day. It's just like sitting down with yellow legal pad and like working on jokes and like throwing stuff away and playing with ideas. And, and the, the person was just like, that sounds like torture. And he's like, your blessing in life is when you find the torture you're comfortable with.

Yeah, back to the boring.

Yeah, yeah. And like the things that like, that look were— when you describe them to somebody, they're like, that sounds like exhausting or a waste of time or frustrating, monotonous, and you're like, no, I like it. Like, that's, that's probably a good sign.

A couple quotes from Ralph Waldo Emerson that I thought really embodied you: many times the reading of a book has made the fortune of a reader, has decided his way of life. And then, I cannot remember the books I've read any more than the meals I have eaten. Even so, they have made me. Yeah, I don't have a question, but just very, very, very cool. Like, very cool to both discover that through you and also like see you in those quotes.

Yeah. What was the first one?

Many times the reading of a book has made the fortune of the reader, has decided his way of life.

Yeah, well, it's similar to what the the Joseph Campbell thing of reading as a divining rod.

Yes.

Of like, and I think I used that quote or that Campbell thing, like there's a great story of James Cameron, like going to like the USC library and like just reading and like stumbling across like some obscure film technology, like PhD thesis. And for whatever reason, like, finding it really interesting. And, and then, like, following that interest in that, he discovered, oh, I really, like, have an interest in filmmaking. And it was a divining rod of, like, this initial interest discovered in a book and then pursuing it. And, like, that's been my experience of, of books and discovering interests and following them. And yeah, I just couldn't imagine like what, what I would be doing if not for like the guidance of so many books and like the being introduced to ideas and, um, and interests. Um, and it makes me think of like the, like Henrik's idea of unfolding. I think he has something in that piece of just like if you reflect on like how your favorite books became your favorite books or like your friends became your friends or your favorite food became your favorite food, it was just like a stumbling on something that was like, oh, this is— and then the following through on that and like learning more. And yeah, it's following the clues. Yeah. And you just can't predetermine or, or know beforehand. What those things are going to be.

I have a few final questions before we wrap up across some miscellaneous topics. You were a ski bum for a little while.

Yes.

Across different parts of the world. And you've talked about side quests broadly. Why are, why are side quests worthwhile?

Well, my skiing, that ski bum few years was a like kind of classic cliché, like, don't know what I want to do or who I am, and I want to get out there and like discover that kind of a thing. And it was also rooted in like the— at the time I was reading a lot of like the kind of find your passion type books and like find— and my interpretation of like the find your passion thing was like It's like there's a— you are a key and there's a keyhole out there and you have to like perfectly match those things.

As Henrik says, the opposite of unfolding is a vision.

Yes.

Yes.

Yeah. And so like for whatever reason, like I was like, okay, so I got to go out and like find this keyhole. I also remember reading— I want to explicitly say the book, but it was like that. The idea was that nobody actually likes to work. Nobody actually likes making lots of money. Like, what they want is like what they think those things can uniquely afford, which is complete freedom. The freedom to like live in ski chalets and—

Oh, I see.

Beachfront. And so I was like, I'll just skip to the freedom. I'll skip to it. I'll go, I'll go be a ski— I'll go be a ski instructor and basically like do the bare minimum, like meet the quota of ski instructing days, but then just like ski. And for like my first year of doing that, I was like, I've unlocked the secret of the universe. This is what I'm going to do forever.

And then at a certain point, without obligation, right?

Yeah. It's like the, the wolf cutting daisies things or the sword cutting daisies was like what ultimately got to a point where I was just like, kind of like sad, you know, of like this. I'm not happy doing this.

Totally free and without meaning.

With, yeah, there was nothing. And I was just like, did I make a horrible mistake? Now I'm like 2 years behind all my like college friends who are on more traditional career paths. And like, and that, that was the time when I discovered Ryan's work. And I remember I was struck by a story of him leaving Hollywood He was working in Hollywood when he like first dropped out of school. He left that job to be Robert Greene's research assistant.

Oh, wow.

And I remember being like struck by not only the— what I imagine it was like he was taking a pay cut, but also losing like the status of I work in Hollywood and replacing that with, right, I am a research assistant for an author you've probably never heard of. And when I first met him in person at like a conference he was speaking at, I asked him about it and he said that he looked around at like the people ahead of him in Hollywood and like, what do they spend their time doing? And then he compared that to like what Robert spends most of his time doing. He even— he called Robert and it went straight to voicemail. And he's like, he's writing, he's reading, he's making note cards, he's engaging with— he's, you know, he's— that's probably what he's doing right now. And that is what his life resembled what I wanted mine to look like. And like, conversely, the people 10 and 15 years ahead of me in Hollywood, like, I didn't want to spend my time doing those things. And there was no amount of like money or or status that can really fix being miserable.

Yes.

All day long.

Yes.

And like at that time I was still doing the ski stuff and it forced me to like look at the, the instructors and other like resort employees who were like 50 and 60 years old. And it just like really scared me to think like that could be me one day. And I would look back and be like, I just spent 50 years skiing every day. And that sort of began like my shift from like thinking I'd solved the universe of skiing and not working at all to like making my way towards like what now is mostly just like doing work that is, you know, it's like not— it's not like all bliss all the time. It can be frustrating and monotonous and tedious, but there's still like the reward of, of doing that. And so I have like mixed feelings of like my years as a ski— of a ski bum.

Will you still tolerate side quests of any kind?

Yeah, I think so, because it— I mean, it's, it's like the, the idea of like taking initiative on like these little inklings of things that might be interesting, like Totally. Not, so not completely writing, writing that off, but I guess it like, it would, I'd be less likely to be like, that side quest was really a wanting to like, have no constraints, like the constraints thing, like just be totally free and do whatever I wanted when I wanted. And definitely learning from that, that like, took me to like, a pretty dark, miserable place.

One of my favorite newsletters you put out was this one on this phrase, like, I know what we do here. Why are our environments, physical environments especially, why are they helpful for creativity?

That, um, I know what we do here, that was again, it was Seinfeld. Another comedian was, was saying to him like that he was, he had been struggling to like write and develop new material. And Seinfeld was like, where do you work? It's like, I have an office at home. It's like, so you're like, your kids are there, like your family's there. So he didn't have like, you know, undivided attention. And, and it was just like, it was too— it was his office and it was too like, there were no boundaries around which was which.

And so it's kind of like constraints again.

Yeah. So Seinfeld was like, it was a guy that was hosting like a Netflix, like, presented by podcast. He's like, I assume they're paying you to do this. Like, take, take the money they're paying you and get like a little shack somewhere. It doesn't have to be like crazy, but just like a little writing spot that's just yours. And when you walk in that door, I know what we do. I know what we do here.

Yes.

And so like, and he talks about like treating your brain like a dog you just got.

Yeah, I love this.

I love this.

Sad little dog.

Yeah. Like they, like in the way of like training it to like, this is where you eat, this is where you do your potty. Like when you're here, like you just sit here and you do nothing. And so yeah, I do think the brain is pretty good at like getting habituated to environments, especially once you train it, right? Yeah. And it can also be like, it doesn't have to be a physical, like the, I'm thinking of like the morning pages of like that sparks some sort of like, I know what we do in this journal.

Yes. Yes. Yeah. Even in that newsletter, you had one about like James Cameron having two different desks while he was writing Terminator and some other movie.

Yeah.

And he literally had the desk separating the different movies.

Yes. Yeah, yeah, yeah. So yeah, like one was for— I think it was Terminator. I can't remember the other one. And he had some like tight timeline in which he had to finish them. And so he just like came up with this idea of like the two desks and one being— yeah, just like you get primed and you're able to quickly, quick, quicker drop into like—

yes, change context, change gear. Yes, yes, yes. I have a group I go to on Wednesday mornings to write for an hour and like, I do not write very consistently in my life. Most weeks, honestly, I just write in that session. And yet when I'm in that room, it's like this little kind of like greenhouse in a backyard and like, it is so easy to write in there. Like, it's not even a question. Yeah. Automatic. Yes. It's powerful. Why is it so powerful to bring familiar and unfamiliar together?

This is, uh, the idea of like content or songs or whatever it is, like combining a known and an unknown, or something that's familiar with something that's unfamiliar, is just like captivating for an audience. If I think of some of the, some of the stuff that like has gone the most viral that I've posted on social media, it usually has this element of known and unknown. It's like there's a, um, a story of Tom Hanks when they're making Forrest Gump, and I told the story of like how he came to the way he speaks in Forrest Gump.

Right, right, with the kid.

Yeah, so that's like, that's a very well-known movie character, like voice. Everyone can kind of think of like that Forrest Gump voice. Unknown was like that, how he came to it.

Yes. Yes. Everyone has a touch hold there. Like everyone has a point of entry.

Yeah. There's a, this paper I read not too long ago about like the idea of like in kind of motivation theory. The sweet spot is something that's not too hard and not too easy. Yeah, yeah, yeah. If you're playing tennis with a 4-year-old and you're just like dominant, it's like you get bored.

Or a video game. It's like a video game designer is really good at this. They're really good at making it like it gets harder as you improve.

Yeah, yeah. So there's a sweet spot between it being like, this is way too easy and like, this is impossible. It's pointless. And there's something similar about like sweet spot between like, this is so obvious that it's boring and this is like, what is so obscure? What even is this?

You've lost me.

Yeah, yeah, totally, totally, totally. And I just like, if I, when I reflect on like some of my favorite reading experiences, it usually has that element of like a slight familiarity with like, never heard it put this way or never heard like this story about this person. So I just, I like it as a reader and like a consumer. And then it's, it's fun to like try to bring those elements together in like in the writing as well. Yeah.

Yeah. Yeah. You said, I found a really great idea and now I have to execute it, execute on it regarding the book. I think that was a year or two ago, maybe a year ago.

I said that?

Yeah. What does that feel like? You're— you were speaking about the— maybe the opportunity and the burden of having found something.

Yeah.

And knowing when it's actually ready or done.

Yeah. Yeah. Well, it makes me think of the Hannah Arendt quote that you mentioned earlier of like taking the burden everything that is in existence, like somebody took initiative, they took like the burden of labor and toil upon themselves. And just like there's the great excitement of like the spark of, of an idea that you can imagine, like this would be a great chapter, like great. And then it's like the work of bringing it into existence.

Yeah.

Is a whole nother— Yeah, that's like where the— that's the immediate kind of like what follows. This is something. And then like, I know how long it takes to write a chapter. So we got our work cut out for us. Yeah.

There's an amazing quote about this designer. You say, as Cher got up to leave the room, someone from the city team asked, she'd just done this logo, someone from the city team asked, how can it be that it's done in a second? She says, it's done in a second and 34 years.

Yeah.

Maybe on the other side of that, what you were just describing, the just arduous process of creating, either that you've observed in others, that you found yourself over time, like, yeah, what does it feel like when you can start to like, it's sort of like the magic thing about Steve Jobs. Like, what does it start to feel like when you can actually just like pull on the work you've done in the past? In many ways, you're kind of doing this with the note cards in the newsletter. And of course, that's what this quote is sort of pointing at is almost this— we've talked about like the four stages of competence, like the unconscious incompetence, the conscious incompetence, the conscious competent. And then finally, the unconscious competence, the mastery. It's like almost this, like, if you ask a true master a lot of times, they like, how they did something, they're like not even sure, or they can't even explain it to you. But yeah, I'm curious if there's been any ways that you felt that or that you've gotten to witness it in others.

I don't think I felt the experience of like, like the Paula Scherer when she's, she basically in a second. She was hired to like— Citibank and Travelers were like merging and she was brought in to like create a new logo for— it was going to be like just Citi. And she drew it on a napkin and like, that's what the Citi logo is to this day. And I don't think I've ever had the experience of it, like feeling like it happening fast and like easy, right? For me, it's more like the joy of— I've been— this piece has stories in it that I've been collecting for 3 years, you know?

Yes.

And like, I didn't know when I was going to use it, but like, that work of past me having like done— put in the time to like read the thing or make the note card that I experience more than the other thing of just like, you know, the artist who's like lost in the flow of mastery over their craft. Like, I don't think I like have the mastery of craft to like tap into that. It still feels like very conscious. What were the stages?

It's the first one is ignorance, unconscious incompetence. Yeah. Then awareness, conscious incompetence. You realize you're incompetent. Then learning, conscious competence, and then finally mastery, unconscious competence. I think I feel like you're in number 3.

3, and then also sometimes 2, where it's like, I'm aware that this is not good.

Yeah, yeah, fair, fair.

Yeah, uh, but 3, yeah, conscious, like, of this is good because, like, it took a— there's many years of the— of this good thing, and I like that.

I've done the work.

Yeah.

I, uh, I want to read an excerpt from Robert-Henri in The Art Spirit that you had sent me. Uh, there are many craftsmen who paint pleasantly the surface appearances and are very clever at it. There are always a few who get at and feel the undercurrent, and these simply use the surface appearances, selecting them and using them as to express the undercurrent, the real life. If I cannot feel an undercurrent, then I see only a series of things. They may be attractive and novel at first, but soon grow tiresome. There is an undercurrent, the real life beneath all appearances everywhere. I do not say that any master has fully comprehended it at any time, but the value of his work is in that he has sensed it and has His work reports the measure of his experience. It is this sense of the persistent life force back of things which makes the eye see and the hand move in ways that result in true masterpieces. Techniques are thus created as a need. Your, your line in, in the margin, I think on that one, is the real life of appearances. Why did that quote stand out to you?

That was— I was drawn to, yeah, the, the real life of appearances like we've been talking about, of just like something that seems to be magic or like lofty or somebody with innate talent or like, but then peeling back and finding out that there is like a lot of work and years to make it appear that way. Like, there's a, um, Tom Hanks tells a story of meeting Joe DiMaggio at a— he was at a restaurant one night and the waiter came over, he's like, hey, Mr. DiMaggio wants to meet you. And Tom Hanks goes over and they have this conversation, and Tom Hanks made a comment about like how, how DiMaggio made it look easy out there on the baseball field. And he like leaned in and it was just like, there's a lot of fucking work to make it look that easy. And so I did, I did a thing, a newsletter on like the Joe DiMaggio principle of just like those that make it look easy.

That's like the magician.

Yeah, yeah, yeah. And it's so similar, like the the real life of appearances. Like, things that look one way or seem like effortless, or they're, they're just a natural— there's usually like a real life of knowledge and information and practice and stuff that's just like under that appearance.

I have one last question. We were talking about this a bit with Greta Gerwig and a whole bunch of other contexts about there should be signs that early on in your life you are inclined towards a certain thing. You, you use the term, for me, writing should have probably been off the table. Can you tell the story and maybe reflect on where you've landed in your life of Tongui?

Yeah.

Wow.

Yeah, my, I think it's probably like my earliest memory and it's definitely my most like vivid, like I can like still close my eyes and like go back to the room and like the chair I was sitting in when I think about this story. I was in second grade and I was like really struggling and slow to learn like the alphabet and words and vocabulary and spelling. So it was recommended that I start seeing this kind of like specialist at the school who worked out of like one of those trailers detached from the actual school. And so I would walk over and it's just kind of like kids are on the playground and like they know why you're going in there, you know, it's like the walk of shame. And one of the first sessions with her, she just like put a sheet of paper in front of me and just like, read this list of words to me. And I get like a third of the way down and I get kind of stumped by a word. And she's like, just sound it out. And I was like, tongue, tongue, tongue-gooey. And she goes, tongue. And then just immediately it was just like so humiliated and like, um, and I can still like feel that feeling. Yeah.

Oh, um, funny, those man things that happen to kids, talk about— yeah, just the things that stick with you.

Yeah. And yeah, so I remember like reading a lot of those, those books about like early inclinations and early aptitude of like those being signals, sort of like, follow those. That's what, like, you're meant to do. And so there was, yeah, there was a time where I was just like, when I read those books, I would like sift my memories of like what, what inclinations and aptitudes like did I have. And like, I would always first think of like the Tanguy story. I was like, okay, not words, you know. Not nothing to do with spelling, clearly. Um, and it's why I resonate with like the Greta Gerwig thing of like, you're not born with this personality, like it's, it's developed and like you, it's through doing the work that like you can develop the personality. So that, yeah, that's, that story was just like, I now think on it fondly, like, uh, the Henrik's Third Chair essay where he— it's just like the most— one of the most like beautiful—

total chills—

of writing I can like remember reading like in recent. But he talks about like going to this library where he spent years like wanting and like struggling to be a writer. And now, like, however many years later where it's like starting to happen for him, he walked in there, he's like, the feeling that like past me was sitting there at that table I used to go to was so strong that I pulled out a chair and sat next to him. And he just like, his appreciation for this person, this past him that like stuck it out.

Who, by the way, was feeling so lost and unmotivated. Why am I even doing this? It's a waste of time. Yeah, I can't.

Yeah, yeah. And like that present-day him that is getting to do what that person like wanted, of just being like, thank you for your persistence and like showing up when like it was a struggle and it was frustrating and it was lonely and you didn't know, like, and having gratitude for that person. And then that, I mean, the piece ends where he's just like, and then I turned around and there was a third chair. Like, it's just like the best. But I remember reading that and just being like, I was so— I got sort of like chills and like almost like teary-eyed of like the version of me that like did Hooked on Phonics and like worked on like figuring out how to spell and vocabulary. And now it's just like my day is filled with reading and writing. Yeah. With like those things that were like took a long time to develop and cultivate and like some past versions of me, like, showed up and did those things. And yeah, I don't know. That's all I got.

Thank you, Billy.

Thank you.