![[Dialectic/Art/29-Billy_Oppenheimer.jpg]] *Dialectic Episode 29: Billy Oppenheimer - Attuned to Clues - is available on [Spotify](https://open.spotify.com/episode/11JumTfj1RN4KXvuStgipE?si=89b4e7f50b824522), [Apple Podcasts](https://podcasts.apple.com/us/podcast/29-billy-oppenheimer-attuned-to-clues/id1780282402?i=1000725983978), and [YouTube](https://youtu.be/xOCB65L-NDo), and all podcast platforms.* <iframe data-testid="embed-iframe" style="border-radius:12px" src="https://open.spotify.com/embed/episode/11JumTfj1RN4KXvuStgipE?utm_source=generator" width="100%" height="152" frameBorder="0" allowfullscreen="" allow="autoplay; clipboard-write; encrypted-media; fullscreen; picture-in-picture" loading="lazy"></iframe> <iframe allow="autoplay *; encrypted-media *; fullscreen *; clipboard-write" frameborder="0" height="175" style="width:100%;max-width:660px;overflow:hidden;border-radius:10px;" sandbox="allow-forms allow-popups allow-same-origin allow-scripts allow-storage-access-by-user-activation allow-top-navigation-by-user-activation" src="https://embed.podcasts.apple.com/us/podcast/29-billy-oppenheimer-attuned-to-clues/id1780282402?i=1000725983978"></iframe> <iframe width="560" height="315" src="https://www.youtube.com/embed/xOCB65L-NDo?si=1pQTqgZvcbMGZkwK" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" referrerpolicy="strict-origin-when-cross-origin" allowfullscreen></iframe> # Description Billy Oppenheimer ([Website](https://billyoppenheimer.com/), [X](https://x.com/bpoppenheimer)) is a researcher and writer who works closely with [Ryan Holiday](https://ryanholiday.net/) and [Rick Rubin](https://x.com/rickrubin), and publishes the [“Six at 6” newsletter](https://billyoppenheimer.com/newsletter). Billy is also working on his first book, *The Work is the Win.* We kick off by discussing one of my favorite new ideas: "*looking for clues*," a process and philosophy for creativity that Billy learned from Rick Rubin. He shares the story Rick told him when he learned and adopted this language, which is so representative of how Billy (and I!) research in our work. From there, we talk about Billy's robust research process and how he has created an external brain of the ideas and patterns that inspire him rather than relying on memory. We also talk about the importance of time as a filter and a series of maxims that underpin his work and creativity. We discuss the importance of inputs over outputs and his big idea and book title, "The Work is the Win," as well many related ideas on success, complacency, compounding, standards, initiative, local maximums, and more. We finish with some lessons from Billy's favorite people. This conversation is a field guide for making things, pushing through the messiness of progress, and attuning yourself to the richness of the world that often takes the shape of clues. Full transcript and all links: https://dialectic.fm/billy-oppenheimer # Timestamps - 0:00 - Intro - 1:20 - Looking for Clues with Rick Rubin - 17:42 - Billy's Own Clue-Seeking - 24:26 - Balancing Listening to the Market and Finding Unique Influences - 31:17 - Memory, Notecards, and Billy's External Brain - 37:13 - Making Notes for an Ignorant Stranger, or Leaving Clues for Your Future Self - 45:09 - Lingering and Time as a Filter - 52:51 - Billy's Book and Big Idea: "The Work is the Win" - 1:00:07 - Be Great Regardless - 1:04:31 - Following Up Even When Your Abilities and Standards Don't Match - 1:10:10 - Fending Off the Wolf at the Door (The Comfort of Success) - 1:15:55 - Unfolding and Planting Seeds - 1:18:17 - Taking Initiative and Opening Doors: "He Who Hesitates is Lost" - 1:24:58 - Stupid Bravery and Getting Past the Sewage - 1:30:16 - Local Maximums and Resisting Personal "Folklore" - 1:36:14 - Some of Billy's Favorites: Ryan Holiday, Rick Rubin, Steve Jobs, John Mayer, Greta Gerwig, Jerry Seinfeld, Ralph Waldo Emerson - 1:56:45 - Side Quests - 2:02:26 - "I Know What We Do Here" and Creative Environments - 2:05:28 - Bringing Familiar and Unfamiliar Together - 2:09:26 - Mastery and Compounding - 2:12:44 - The Real Life of Appearances - 2:15:43 - "Ton-goo-ey" and The Gifts We Give Ourselves # Links & References - [‎McCartney 3, 2, 1 (2021)](https://letterboxd.com/film/mccartney-3-2-1/) - [The Way of the Tracker: The Path of “not this” - Boyd Varty](https://boydvarty.com/the-way-of-the-tracker-the-path-of-not-this/) - [Eddie Murphy Is Tracy Morgan's Favorite | Comedians In Cars Getting Coffee](https://www.youtube.com/watch?v=ehoV6LoIpKc) - [Poetry Unbound](https://onbeing.org/series/poetry-unbound/) - [When We Cease to Understand the World- Benjamín Labatut](https://www.goodreads.com/book/show/62069739-when-we-cease-to-understand-the-world) - [Fill Up To Pour Out - Billy Oppenheimer](https://billyoppenheimer.com/johnny-cash/) - [Atomic Habits - James Clear](https://www.goodreads.com/book/show/40121378-atomic-habits) - [The Subtle Art of Not Giving a F\*ck - Mark Manson](https://www.goodreads.com/book/show/28257707-the-subtle-art-of-not-giving-a-f-ck) - [The Psychology of Money - Morgan Housel](https://www.goodreads.com/book/show/41881472-the-psychology-of-money?from_search=true&from_srp=true&qid=adtiowcK8J&rank=1) - [LeBron James shows off photographic memory](https://www.youtube.com/watch?v=eNVJFRl6f6s&pp=0gcJCRsBo7VqN5tD) - [The Notecard System - Billy Oppenheimer](https://billyoppenheimer.com/notecard-system/) - [Robert Greene](https://en.wikipedia.org/wiki/Robert_Greene_(American_author)) - [Mike Nichols: A Life - Mark Harris](https://www.goodreads.com/en/book/show/53479533-mike-nichols) - [The Journal of Eugene Delacroix - Lucy Norton](https://www.goodreads.com/book/show/606409.The_Journal_of_Eugene_Delacroix) - [19. Henrik Karlsson - Cultivating a Life that Fits - Dialectic](https://dialectic.fm/henrik-karlsson) - [Stadium of selves — Steph Ango](https://stephango.com/stadium-of-selves) - [8. Steph Ango - Tools for Amplifying Our Light - Dialectic](https://dialectic.fm/steph-ango) - [The third chair - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/third-chair) - [Secrets of the Creative Brain - Nancy Andreasen | The Atlantic](https://www.theatlantic.com/magazine/archive/2014/07/secrets-of-the-creative-brain/372299/) - [Setting down the snow globe - Jackson Dahl](https://x.com/jacksondahl/status/1704182906837418113) - [Billy on REST](https://x.com/bpoppenheimer/status/1639281614013321216) - [Face it: you're a crazy person - Adam Mastroianni](https://www.experimental-history.com/p/face-it-youre-a-crazy-person) - [Tennessee Williams – The Catastrophe of Success](https://genius.com/Tennessee-williams-the-catastrophe-of-success-annotated) - [Critique of Pure Reason - Immanuel Kant](https://www.goodreads.com/en/book/show/18288.Critique_of_Pure_Reason) - [Billy on Constraint, Gide, and Kant's Dove](https://billyoppenheimer.com/may-18-2025/) - [‎There Will Be Blood (2007)](https://letterboxd.com/film/there-will-be-blood/) - [The War of Art - Steven Pressfield](https://www.goodreads.com/en/book/show/1319.The_War_of_Art) - [Billy on unfolding and my exploratory journey](https://billyoppenheimer.com/june-15-2025/) - [He who hesitates is lost - Joe Rogan & Jordan Peterson](https://youtu.be/ZCPcoDhlF9U?si=1KPG0XUil_398uU_) - [Everything that turned out well in my life followed the same design process - Henrik Karlsson](https://www.henrikkarlsson.xyz/p/unfolding) - [Billy on John Mayer, Huberman, Sewage, and Ouija Boarding](https://x.com/bpoppenheimer/status/1887557666001600522) - [Steve Jobs on folklore](https://www.youtube.com/watch?v=5S7MJ8042ak) - [The Making of Prince of Persia - Jordan Mechner](https://www.goodreads.com/book/show/52824295-the-making-of-prince-of-persia) - [Make Something Wonderful - Steve Jobs](https://book.stevejobsarchive.com/) - [‎Lady Bird (2017)](https://letterboxd.com/film/lady-bird/) - [‎Frances Ha (2012)](https://letterboxd.com/film/frances-ha/) - [Billy on Greta Gerwig and David Whyte](https://billyoppenheimer.com/august-24-2025/) - [Billy on "I know what we do here"](https://billyoppenheimer.com/october-15-2023/) - [The Art Spirit - Robert Henri](https://www.goodreads.com/book/show/207781.The_Art_Spirit)` # Transcript ## [00:00:00] Intro **Jackson:** 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. six. Six is really about the inputs, not the outputs. Billy's also working on his first book. The Work is the Win. Billy is 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 three 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 an 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. ## [00:01:20] Looking for Clues with Rick Rubin **Jackson:** Billy Oppenheimer. **Billy:** Here we are. **Jackson:** Here we are. This was supposed to happen a few weeks ago, and I had to push. I'm very glad to be here. **Billy:** I'm glad you made the trip. **Jackson:** 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? **Billy:** Yes. Looking for clues. I started doing some work on a research assistant basis with Rick Rubin a couple years ago. The first time I met him in person, he said, "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." He told me the story of a documentary he was working on. I told him recently that I think about it all the time and 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, I may leave out, but I, I think it's just so good and it gives a real sense of like his, approach and how I've come to think about my own sort of research process. He was approached by somebody who had seen a documentary Rick did with Paul McCartney. The Paul McCartney documentary was an interesting approach to an autobiographical documentary. In this case, it was Rick and Paul standing over a soundboard, and Rick would play some of the Beatles songs. **Jackson:** I haven't seen this. **Billy:** It's amazing. I think it's called \*3, 2, 1\*. stage design is just this 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 musical career, breaking down some of the songs and how he wrote them and how they came together. saw it and had been thinking about wanting to approach somebody about doing a documentary. They were 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. And... **Jackson:** Great answer for a creative project. **Billy:** Yeah. Which in itself was like a great lesson. I've used that a 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 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. After said that to the person, I'll commit to thinking about it, he 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." The first clue was he was watching a lot of documentaries in the genre of a main character whose life story and work is explored throughout the documentary. He noticed they all start the same way, which is a cast of characters—people who worked with, were friends with, or family members of the main figure. The implication is these are the people we'll be returning to over the next two hours, and they'll help us tell the story of this person. Rick said in the early stages, "I like to learn things to rule out things." He wants to know what the conventions are so he can try to avoid them. So some, some of the first clues are like, what are we not gonna do? **Jackson:** There's a version of this idea from this guy, Boyd Vardy, where he calls it the path of not here. He's a lion tracker, and his notion is that when we take a wrong path, we can feel like it was a waste of time. But by knowing it's not that path, you're actually getting closer to the thing. **Billy:** Yes. **Jackson:** Which is cool. **Billy:** I love that. **Billy:** The path of not here. **Jackson:** Yeah. **Billy:** So that was the first clue: it wasn't going to be 10 or 12 people on plush couches, one after the next. The next clue was from watching interviews with Eddie Murphy. He noticed that in an interview context, Eddie seems uncomfortable and different than his stage personality. On stage, he seems very comfortable and in his element, but in a one-on-one sitting across from interviewer, he just seemed out of place. Rick couldn't tell if Eddie doesn't like to do interviews, if he's just shy, or if it takes him time to warm up with a person he doesn't have a rapport with. But he noticed it. Then he was watching Eddie's interview with Jerry Seinfeld in \*Comedians in Cars Getting Coffee\*. He noticed that for the first couple of minutes, it was that same uncomfortable Eddie in an interview setting. But then something switched, and he became more like his stage presence. He couldn't tell if it was the format of the show—they're not sitting in chairs with cameras directly on them, they're in a car and then a coffee shop and moving around—or if it was because Seinfeld is a peer that he respects. But he noticed it. listening to a podcast called \*Poetry Unbound\*. The format of this podcast is the host reads a poem, start to finish, and then for the next 10 or 15 minutes, gives more context about the poem, the poet, the time period, or some of the metaphors they're exploring. And then he reads the poem again. **Jackson:** Wow. Cool. **Billy:** And Rick said what he likes about that podcast is that on the second read, it's a totally different poem. **Jackson:** You have all this texture. **Billy:** Yeah. He compared it to when you go to a museum and you get the headset. You're looking at a painting on the wall, and you press play on the commentary for this painting. With this information, you're seeing the painting differently. **Jackson:** One of the things I've come to appreciate more over time is that I used to have the view that I needed to experience art purely. I watched this Miyazaki movie he made a couple years ago and was kind of confused. I read a review that I really loved that had all this context, and the second time I watched the movie, I loved it. And I wondered, am I allowed to love it? Do I only like it because of the critic? But I actually think this is a really underrated thing. There are so many different ways that the texture can change the meaning of something, even just by watching something a second or a third time. **Billy:** I think about this all the time with some of my favorite bands, writers. It begins with an initial attraction, and then I want to know more about who made this. An example would be, I'm a big Vampire Weekend fan. **Jackson:** Likewise. **Billy:** That began with a song popping up on a random playlist. I liked the song, and for some reason, I wanted to know more about Ezra Koenig, the frontman of Vampire Weekend. I can't remember the specifics of it, but maybe there was a lyric. I started reading a bunch about Ezra, and I really resonated with path to pursuing music and the ways he articulates and thinks about songwriting. Through learning about him and being drawn to those things, my affinity for Vampire Weekend gets larger and larger. So I think all the time about that weird phenomenon of how your interest and love of something can be informed by getting to know more about the stories behind it. It doesn't have to be the person themselves, but a cool story behind how something was made. **Jackson:** Right. So he's inspired by Poetry Unbound. **Billy:** So that's another clue of this: reciting a poem, giving more context, and reciting it again. He has this nightly ritual where after the sun goes down, he turns off his phone, he puts on some blue light blocking glasses, and he 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 'cause I knew 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 documentary. It was a series of episodes. Kind of that first clue of like, what are we not gonna do? So this is, was that first initial, instinct to go against the convention of a one and a half or two 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. **Jackson:** Cool. **Billy:** On the day of filming with this person, that was. Either, you know, the, the main figures collaborator or somebody that was just inspired by them, they're given an address to a nondescript building. They do hair and makeup and are given an earpiece. Then Rick comes in through the earpiece, and they do a sound check while they're doing hair and makeup. The person, person is led by the hair and makeup person to a door and is just told, "I think it's through there." He wanted it to be very vague. They go through this door and there's an X on the floor. They walk over to the X, lights come on, and they're on a recreated stage. They're in their element. Rick is in the back of the building next to a projection screen. He said the reason they did the sound check is that otherwise, they would have seen me and had the instinct to yell up at him. But because they'd been talking this whole time, they continued their conversation. 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, They watch it start to finish. Then he starts it again and person, he'll stop and prompt “What are you seeing here?” In the edit, I haven't yet seen it, but my assumption is it's going to be that \*Poetry Unbound\* style of show: show the appearance, break it down with the help of person we'd see it again. I was seeing how all these clues were coming together. The \*Poetry Unbound\* thing, watching all different kinds of documentaries and learning what he didn't want to do. It's not going to be one two-hour thing; it's going to be a series. The clue from \*Comedians and Cars\* is that you can do interesting things on the move or in different settings. I'm starting to see how they come together and 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. **Jackson:** What's amazing about all these is that 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. Yeah. Like, none of these things are sort of necessarily, they need to be acted on or, or inherently going to like, uh, be made worthwhile. It's just an attunement that might lead to something. **Billy:** Yeah. Yeah. I love he, he was always like, I don't know what it is, but I noticed it. Mm **Jackson:** mm **Billy:** There's something, something there. There's something like, and I don't know if it we will use it or not, but like. It seems, seems it's interesting. Mm-hmm. And just like that's enough for it to be like captured and like **Jackson:** Yeah, yeah, yeah. **Billy:** You know, part of the, the catalog of clues for this particular project. **Jackson:** 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. **Billy:** Yeah. Taking in those noticings, letting them marinate, and then at some point they coalesce into a unique creative output. It was very helpful for him to tell me that story and to use this terminology of clues. He finishes telling me that story and he goes, “I can't remember why I'm telling you this.” And I said, “You wanted me to get a sense of your approach to a project.” He goes, “Oh, yeah,” and strokes his beard. I could tell he still didn't know what this had to do with that. I said, “So essentially, we are in the clue-gathering stage of this project we're working on.” And he said, “Yes, exactly.” It was very helpful because up to that point, he would text me a link to a YouTube video, a screenshot from a book he was reading, a clip from an audiobook he was listening to. I didn't know what I was supposed to do with these things. And now it was clear: those were clues. **Jackson:** Yeah. They didn't need to be acted on necessarily. **Billy:** Yeah. They might not have anything to do with what we're working on, but they might. **Jackson:** Wow. **Billy:** There are so many things I love that. One of them is suspending judgment of whether this thing is going to be useful or not. He's just sending lots of things; he spent a lot of hours reading something, not sure if it's going to pay off on a project in the future. He's in the habit of gathering things and not needing to know, "Am I sitting down to read this book? Will this work pay off?" **Jackson:** It's really cool. it reminds me, there's this, there's this author Benjamin Labatut who wrote this book called, \*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, you're sort of coming up with stories and he's like, no, writing and even writing fiction is more like walking and picking flowers up off the ground. And it's such a beautiful metaphor for like what creativity's actually like, and so clearly somebody who might watch this documentary, it's gonna come out, or I'm sure other things Rick's done might think, oh man, like he's just so creative. And in fact, t his is the peak 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. **Billy:** Yeah. there's a great interview with Johnny Cash and he's, you know, one of the most prolific songwriters of all time. at one point I like looked it up and the, 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. **Jackson:** Mm. **Billy:** He's got fill up 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 form connections and you see like, oh, these things put together in this way will make for a u nique creative output. **Jackson:** Wow. ## [00:17:42] Billy's Own Clue-Seeking **Jackson:** You spend a lot of time looking for clues. **Billy:** Mm. **Jackson:** How does that manifest in your day-to-day practice? **Billy:** A lot of my clue hunting is reading lots of biographies. I love journals of artists or collections of letters of artists because I love reading about and finding stories of creative people—how they go about their work and how things came into existence. Along with reading biographical content, which are the best sources for finding those stories, I also like to read more academic psychology, neuroscience, and anthropology. Things where there are concepts and big ideas. My favorite thing is reading a book on the fundamentals of one field and you come across a concept, and that story about James Cameron making \*Avatar\* or \*Terminator\* perfectly illustrates this concept. I just love connecting things. The person writing about this concept in an anthropology book is not thinking of \*Avatar\*. **Jackson:** Yes. **Billy:** I'm always reading and listening to stuff. I like podcasts and I like watching documentaries. Even if I'm putting on a random playlist as I'm working throughout the day, I'll make a note of a lyric. Everything could potentially be a clue. This morning we were having conversations and you were saying stuff that I made a note of, and it could be a clue. Everything could potentially be a clue for a future project or piece of writing. But it's mostly books. **Jackson:** One of the things I love about this framing, and since you initially told me about clues, it embodies how I think about what I do. I love that it captures this broad attunement or attention that isn't demanding that it immediately pay off. It's just an awareness. It's a keen awareness, and you're looking for a signal. To be clear, there's judgment there, but it doesn't have to have an immediate payoff, which I think is really powerful. **Jackson:** There are 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 another quote from Joseph Campbell. You say the mythologist Joseph Campbell talked about how reading is like a “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. 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 that there is a pretty significant discernment or judgment here. I'm curious how you balance that really high bar for what actually makes a clue, or even what draws you into a piece of content, with the reality that oftentimes things aren't immediately the most exciting. I think we've all had the experience where you start reading something you're not that into, but if you just push a little further through the mud, you end up finding the gem. **Billy:** It's a hard question. The concept of taste is in the air right now. The main way to distinguish yourself in world of AI is: do you have good taste? I think it's the ultimate perennial challenge of making things—finding the overlap between what you find interesting and useful or entertaining, and what an audience will find interesting and useful. That middle is a really hard thing to pinpoint or locate. think it's why some of the conversation around AI tools is a little overblown, because I don't think that is an equation that can be scienced or solved. There's always some uncertainty. I'll love something I'm publishing and be really excited about it, and then it's crickets. Other times, I'll really like something but not know if it's going to resonate with an audience, and then that thing goes crazy. It's really hard to know how things are going to land and if your taste is going to be shared by an audience, a reader, or a viewer. Honestly, I have almost given up on trying to predetermine or predict. It's really just a feeling. Everyone's had the experience of reading a book you can't put down. You start to read in bed, planning for 10 minutes, and the next thing you know, it's 2 a.m. and you're still reading. always looking for those kinds of books and for that specific feeling of something grabbing me, where I can't stop reading. I do think you get better at noticing it and maybe developing a system for what to do when you have that feeling—capturing it, organizing it, and coming back to it. ## [00:24:26] Balancing Listening to the Market and Finding Unique Influences **Jackson:** You find all kinds of really interesting things, and you are literally a professional researcher in some sense. But what about when it feels like you're searching for a needle in a haystack? Do you have a sensibility for knowing how far to keep going? For instance, if the first chapter of a book isn't that interesting, how does that decision-making process happen? Or are you just sniping only the good stuff? If it doesn't hold me, are you out? **Billy:** It's a little bit of that sniper thing. do think part of a writer's job is the work of making a story or an idea compelling. I'm quick to quit books. That feeling of being hooked into something is what I'm always looking for, so if it's not happening, I'll put it aside. There are times when, on a first attempt, I'm not grabbed by a book for whatever reason. I'll put it aside and then come back to it a year or two later. **Jackson:** You'll find it when you're ready. **Billy:** Yes, you find it when you're ready. I just didn't have the reference points yet for it to be really interesting in the way that it now is. Now I think less that I'm quitting it, and more that it's just not for me right now. I'll maybe come back to it, and at a later date, it will hook me. I talk to a lot of people who say that when they start a book, they have to finish it. Often they're stuck on a book that they've been trying to finish. **Jackson:** And thus they're not really reading. **Billy:** It's counterproductive because 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." Reframing it from "I'm quitting" or "I'm not finishing"—I think there's a part of people that feels, "When I start things, I finish them." And so they think, "I can't quit this book." But you're not quitting it; you're putting it aside for now. It's just a little bit of a mental reframe. I do that a lot, and I always have. Anytime I see somebody mentioning a book I might enjoy, or I listen to a podcast where they make an offhanded comment about some book, I'm always ordering books that are coming in. So if something's not doing it for me, I'll crack something else open. **Jackson:** One question that relates to this: you have a line somewhere where John Mayer is talking about Top 40 music. **Billy:** Oh, yeah. **Jackson:** And he says people aren't wrong. **Billy:** The audience isn't wrong. **Jackson:** Yeah, the audience isn't wrong. I'm curious how you think about mainstream influences and making sure you're still tuned into what the market wants, while also finding the really unusual or unlikely influences. It's almost like a barbell. **Billy:** I love that idea from Mayer. It kind of contradicts what I was saying about Rick Rubin learning things to rule them out. Mayer is tuned into the Top 40, not to mimic it or say, "Okay, this song's a hit, let's follow this as a formula." I think that is a trap. **Jackson:** It's also just on the record to be extremely, "I don't care what anyone else thinks. I don't care about the market at all." **Billy:** But he is a voracious consumer of great art and great architecture. He just loves great things. I think the mistake is reverse-engineering something. You see this a lot in the nonfiction book space. If you go to a bookstore and pick up a new nonfiction book, it's probably trying to be \*Atomic Habits\*. It has a four-part structure, a dramatic opening story, diagrams—because that is the format of \*Atomic Habits\*. I always think that's the wrong lesson to learn because \*The Subtle Art of Not Giving a F\\\*ck\*, for example, is another massive book with a very different structure. \*The Psychology of Money\* by Morgan Housel has a very different structure. So the lesson is that the structure was perfect for James Clear's content and his ideas. Likewise, Mark Manson's structure was perfect for his ideas. It's about being tuned into what is working but not following that as scaffolding, thinking, "All right, let me just jam my things into a four-part structure with a dramatic story." But then on the other side, there's the anxiety of influence, of not wanting to look at \*Atomic Habits\* because you don't want your ideas or the structure you're thinking about to be contaminated. You're thinking, "This book was a massive bestseller. My book doesn't really look like that. Maybe I'm off track." So there's a fine line between being tuned in but not following it as a recipe book, versus being completely oblivious to it, going off in a cave, and then coming out with this thing and realizing **Jackson:** You're not tuned in. **Billy:** You're not tuned in. **Jackson:** What about the really unlikely influences? How do you go about finding those? **Billy:** I'm just following threads. One thing I do all the time is when I'm reading a biography, and there's a section about how the person the book is about read and loved another book, I'll check that book out. You're just following rabbit holes. I'm not really systematic about it. I just follow curiosities, and then you stumble on someone that's more niche or less well known. But I'm not specifically conscious of trying to do that. **Jackson:** I think it would be hard to be systematic about finding the edges. ## [00:31:17]  Memory, Notecards, and Billy's External Brain **Jackson:** I want to talk about the second part of the process, downstream of clues, which is how you build this "cultivating an external brain," in your words—how you build the scaffolding to collect all these things. First, 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 beggar." **Jackson:** You go on to talk 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." 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." You also talk about the famous story about LeBron James remembering seven minutes of a play. Most of us don't have this LeBron James or Paul Simon memory. As a result, we have to cultivate an external memory. Can you talk about what you've learned and how you think about doing that in your process? **Billy:** I adopted slash adapted Ryan Holiday's notecard system, which he learned from Robert Greene. It's literally boxes of 4x6 notecards. I've never seen Robert's actual cards, but I have seen Ryan's. His are filled with shorthands: a phrase, a word, or a single sentence that conveys a story from a book. They are little reminders capturing the broad strokes of something. You notate it with the book and page number so you can go back and find the specific details. **Jackson:** They're little prompts, almost clues. **Billy:** Clues, yes. **Jackson:** A clue on a piece of paper. **Billy:** It's a physical clue. Ryan and Robert file them in boxes which are broken into themes or categories. If the box is for a specific book, there are chapter sections, and the cards are all the material for that chapter. I do a version of that. On my notecards, I found it was hard if I did the shorthand of a word or a phrase. A couple of weeks later, looking at that card, I don't remember the context or what I wanted to remember. **Jackson:** Implicit in all of this is that our memories are way worse than we think they are. **Billy:** Terrible. **Billy:** I try to add the necessary context. If it's a quote, it's sandwiched between some context leading into it, the way it might appear in a piece of writing. **Billy:** They go in one of five or six different boxes that are filled with cards. Usually, when I come across a story in a book, I think, "Oh, this is perfect for a section of notecards that already exists." So I make a note about it and put it in that section. But it also happens where I can't think of where it would belong. When I was first starting the system, a mistake I made was that if I didn't know exactly where a card went, I just wouldn't make the notecard and would leave it. **Jackson:** It doesn't have a place. **Billy:** It doesn't have a place. Now, in each of the boxes, there's a section at the front that says "waiting room," and a card will go there. **Jackson:** It's a seed waiting to grow. **Billy:** Yes. Then a couple of weeks later, I might read something and think, "Oh, this is like that story in the waiting room." Then those two cards become a section. **Jackson:** Yes. **Billy:** Once a section fills out with 15 or 20 cards, that's my cue that there's something here. **Jackson:** It's bubbling up. **Billy:** It's bubbling up. I realize I've got a lot on this, so I figure out how these pieces fit together. The writing is more or less fitting those Lego pieces together. **Jackson:** For anyone who's read your writing, it's very clear. You've talked about how your writing is just the exhaust of this process—the most obvious export of what you're doing. **Billy:** Yes. I'm totally reliant on it. All of my output is just a function of the inputs. For better or worse, I identify and feel more like a reader and researcher. The writing is like asking, "Here are some cool things I found. Does anyone else think they're cool?" The writing is just the urge to share these stories I've read and loved, hoping **Jackson:** the bubble up. It's the exhaust. ## [00:37:13] Making Notes for an Ignorant Stranger, or Leaving Clues for Your Future Self **Jackson:** There's an idea you started to talk about: communicating with your past and future self and what this external brain is doing. You were talking about Niklas Luhmann, who created the Zettelkasten method. of communication is that the partners can mutually surprise each other," which is awesome, especially when the partners are yourself. I know you think about this forward communication in two ways: your questions in the margin and your codes, like the less-than and greater-than signs. Can you talk about how you think about those two constructs and how they enable you to communicate with your future self? **Billy:** Niklas Luhmann also has another great idea about making notes for an ignorant stranger. **Jackson:** Wow. **Billy:** That's what you are when you come back to it. We think, "There's no way I'm going to forget this story." You come back to it, and it's highlighted and underlined. You're like, "What was I loving about this?" I try to make the note cards for an ignorant stranger. You should be able to pick one up and have enough context to make out what this thing is. In a similar way, in the margins of books, I try to do that for myself. I'm reading this biography of Mike Nichols right now, and a critical collaborator in his life was this woman, Elaine May. So Elaine May is introduced on page 34, let's say. On 35, 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's ridiculous. **Jackson:** You're adding little affordances. You're taking the burden of understanding a context in the present, when most of us do it in the future. We say, "Oh, they'll figure it out." **Billy:** In the moment it feels ridiculous. This happened three paragraphs ago. But when I finish that book and I go back through it and this page is dog-eared and it says "she," I'm not going to remember that it was the very page before. So I do a lot of notation. **Jackson:** You could imagine that's a pretty simple one, but I'm sure there are all different kinds where it's actually a little bit more of a complex context. It's so nice to have when you go back. You couldn't even just turn to the page before. **Billy:** I do stuff like the questions in the margin. For another specific example, I'm reading the journals of Eugene Delacroix. It was recommended to me by Henrik Carlson. I loved your conversation with him. After listening to it, I sent him this thing from a book that he made me think of. We hadn't communicated before, but he said, "Oh, you should read the Eugene Delacroix Journal." So I'm reading that right now. **Jackson:** Who is Eugene? **Billy:** He was a French painter. 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?" When I'm going back through the book, I'll see that and it'll quickly remind me of why I liked that, because I sometimes think a lot of what I'm writing is things that have already been said. And it was like, that's okay, according to Eugene. **Jackson:** You're giving yourself little alley-oops. You're making it so easy to come back and resume what was electrifying. It's cool. The other thing you do is very similar to the Christopher Alexander idea of patterns. You have these phrases that have compressed some latent set of ideas that you're putting on note cards and writing in the margins of books. **Billy:** The less-than sign, equal sign, greater-than sign is something I'll write in the margin, which means text next to that sign reminds me of blank. **Jackson:** This idea. **Billy:** 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 says, 'This is a big thing.'" So I might read a story where 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." **Jackson:** Is that usually how they come? You're taking them from some original source that has a version of this phrase, and you're turning that phrase into a muscle bucket for future ideas. **Billy:** With that example of Mike Nichols, I can think of a million examples of things I've read where little, inconsequential things became very important. I love this articulation of it and this idea that they don't wear a sign that says, "This is a big thing." **Jackson:** It's a personal meme in a way. **Billy:** Totally. **Jackson:** I've done this a little bit, and it's a really lovely way to organize ideas. A simple example is Steph Ongo, who creates the software Obsidian. I've interviewed him for the podcast, and he has this little essay called "A Stadium of Selves." It's about this idea of past and future selves. Every day, today's version of you is on stage performing in front of all of the past yous and future yous. Today is your chance to do something for the rest of you. Anytime I come across that idea—the Hendrix III chair is an example... **Billy:** I was thinking of that. **Jackson:** I tag it "a stadium of selves" or "audience of selves." It's a really wonderful way to improve your memory. If you're just trying to remember the individual isolated instances, good luck. But instead, I'm compounding this bigger idea that's growing in my mind. **Billy:** When you said it's like a meme, it made me think. The reason I remembered the Nichols quote was I first thought "little thing became big thing," which is my shorthand for it now. **Jackson:** It's your clue. **Billy:** It's the clue, and I work backwards from that. I've put that shorthand in a few different places. A note card about a story might go in one section, but then I'll learn this Mike Nichols thing and realize that story is better over here. So I've been reshuffling things around, making that section about things not wearing a sign that says "This is a big thing." My memory was first that little shorthand of it, and then the quote was in there too. ## [00:45:09] Lingering and Time as a Filter **Jackson:** Another part of this is creating space for things to grow and expand and linger or be idle. 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. More broadly, how do you think about creating idle time so that time can be that filter and these things can bake in the oven? **Billy:** Whenever I see someone say, "I was reading this morning about..." I'm immediately out. You were reading this this morning? **Jackson:** I'm guilty of that. **Billy:** You just need to spend more time. The other thing that happens all the time with the notecard system is that most of those cards are coming from books. When I'm reading the book, I'm dog-earing pages. Then when I make the notecards, I'm going back through the book. There might be a hundred pages dog-eared and only 10 notecards. **Jackson:** So it's a double filter. **Billy:** Double filter. One of my takeaways from that is that often the attraction is just the novelty on the initial read. Letting time pass to see if it still excites you the second time through is a better filter. Often, the pages that were dog-eared but don't become notecards were just interesting because I hadn't heard something put that way before, but there's not really anything there. So when I hear, "Yesterday I read this great story," I believe it needs more time to be determined if it was a great story. I'm a big believer in time as a filter. Then there's the Pirsig thing of doing and non-doing. There's another great concept I love from this woman, Nancy Andreasen. **Jackson:** The REST thing. **Billy:** Yes. neuroscientist who, when she was coming out of school, most experiments for creativity were designed with a control group where people sit on a couch and do nothing. They used brain imaging machines, and then the experimental group would do puzzles, math problems, or some sort of creative task to see what parts of the brain were lighting up. She was going to design her first study, and it was this baked-in assumption that the control group was always people doing nothing. But Andreasen realized that when she sits on a couch and closes her eyes, her mind is firing. She comes up with so many ideas. **Jackson:** Nothing, in quotes. **Billy:** So she was the first to actually test that. Her finding from that study was that when you're sitting doing nothing, you're actually using some of the most creative parts of your brain. **Jackson:** Shower thoughts. **Billy:** Shower thoughts. When you're sitting in bed before falling asleep. I often call this letting... **Jackson:** ...the snow globe settle. **Billy:** Oh, it's like that. **Jackson:** What I'm implying is a level of clarity. If I'm shaking the snow globe, I don't actually get to see what's going on in there. But when I let it settle, there's so much more here than I thought. **Billy:** She coined the term REST, an acronym for Random Episodic Silent Thinking. It's just a bunch of fancy words for what your brain is doing when you're not having any inputs coming in. You could be on a walk, and if you're not listening to a podcast, Random Episodic Silent Thinking is what your brain is naturally doing. When it's doing that, her brain imaging showed it's not only lighting up, but it's making connections. Parts of the brain are connecting things. Ever since learning about that, I try to carve out time for that every day. **Jackson:** Increasingly, in our modern world, it doesn't happen by accident. **Billy:** No. And it's really hard because I do love clue hunting. It's hard to just sit here and do nothing when I could be reading, listening to a podcast on this walk, or having a speaker in the sauna. So I try to do a half hour of just nothing. Just sitting, and pressure that something has to come of it. **Jackson:** Yes. **Billy:** It's more of a curiosity. **Jackson:** Let's see what I find here. **Jackson:** I have a friend who is wonderful and brilliant, but very on his phone. He created this thing where he has to sit on the couch for an hour without his phone, and he calls it the itching hour. I told him, "Dude, you just invented meditation." **Billy:** The random episodic silent thinking is basically what you do if you sit down. That's another interesting thing. I tried meditating, but it just didn't stick for some reason. This 30-minute rest session that I do most days is basically a form of meditation, but I think of it differently. **Jackson:** It's a different set of rules. **Billy:** I don't really know what to make of that, but it's an interesting phenomenon. If meditation hasn't worked, rethink it as something else. That's often where, in those rest sessions, things are bubbling up and I'm making connections. Often on Saturday morning, I'll do an hour of 20 minutes in the sauna, 15 minutes out, 20 minutes in. In that case, I am trying to see if anything surfaces that will be the newsletter theme tomorrow. **Jackson:** Do you have a slight intention? **Billy:** Slight intention. It often happens when I realize I have been thinking about three different things pretty regularly in the last couple weeks. There's something here. And I still would rather just read or have a podcast, so it's definitely a difficult thing to carve out. I think increasingly for all of us. ## [00:52:51] Billy's Book and Big Idea: "The Work is the Win" **Jackson:** There's a line in an interview you did where you observed that you authentically get more dopamine from making connections in your research than the dopamine you get on Twitter or in the newsletter from sharing them. Broadly, that feels very you. And it's representative of an idea that you're writing a book about, which is called \*The Work is the Winner\*. You've been working on this for a few years. To start, can you give us a one-sentence thesis for what it's about? **Billy:** The book is about doing things for their own sake rather than the fruits of that work or that effort. I got a bunch of different translations of the Bhagavad Gita. One line that I'd seen referenced related to that book was something along the lines of, "You have the right to action, not the fruit of that action." **Jackson:** Wow. **Billy:** The reason I got a bunch of different translations is for the introductions, where different scholars or people who have had a lifelong love of the Bhagavad Gita and spent tons of time trying to understand this text are detailing the core themes, the core ideas, and the impact it's had on people. I've been interested in that with this book. In one of the translations, the writer of the introduction used the wording, "being utterly dedicated and utterly detached." And that felt to me like a pretty good forwarded summation of this book. **Jackson:** Wow. **Billy:** It's about being utterly dedicated to what you're doing, detached from outcomes, rewards, and status expectations. Not to try to talk someone out of wanting those things, because I do think scientists, for instance, need to win grants to be able to fund their research. Some of those things are important to being able to be utterly dedicated. **Jackson:** Any creative person, or anyone almost doing anything, can't tune out the market. You can't tune out the audience entirely. **Billy:** It's acknowledging that those things can be good, helpful, and useful. The best way to get them is through this approach to work. **Jackson:** 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, as Robert Greene says, is to see if you enjoy what others find tedious. Can you talk about why sinking into the monotony of something is so important? **Billy:** The phrase "get to boring" came from Ben Gibbard, a musician. He was divorced and was asked when he knew the relationship fell apart. He said he didn't have any regrets, but he realized they didn't get to the boring part of their relationship before they got married. It was the exciting spark of a new relationship. They quickly got married and never spent that time just sitting on the couch for a weekend not doing much or going grocery shopping together. It struck me as a good way to find not only relational compatibility but work compatibility. Get to the boring. **Jackson:** You're going to spend your days doing this—your days, hours, weeks, and years, ongoing, long after the sexy part. **Billy:** The coffee bean procedure is related to that. It comes from a writer named Adam Mastriani. He was talking about how he often hears from people who are unhappy in their work lives. When he asks them what they think they'd rather be doing, they say something like, "I really would love to run a little coffee shop." If he's feeling mischievous that day, he'll ask them, "What coffee beans would you use?" If that's a stumper, he'll ask, "What espresso machines would you buy? Would you bake the goods in-house or have a third party drop them off every morning? What point-of-sale software would you use?" It's breaking down the fantasy of running a coffee shop into its day-to-day component parts. Not that you have to have an answer to those things, but does finding out the answer to those questions seem interesting to you? Because if not, you're not going to like being a coffee shop owner, because your day will be filled with that. Getting down to the boring, day-to-day tediousness. For me, on the surface, looking in, it's the publishing and having pieces be read or retweeted. If you're somebody thinking about wanting to be a writer, that looks cool. **Jackson:** Having published a book—sick. **Billy:** But what that person should see and like is how I actually spend my time, because it would look very boring. It's more or less the same few things I do repeatedly, day after day, which I would imagine would get pretty monotonous and frustrating if you don't really like doing those things. Getting to boring can apply to most things. An NFL player plays 16 games a year. What are they doing the other 350-whatever days? Do you want to do those things? **Jackson:** The other example I gave in the comedian's context is Seinfeld, with somebody talking about making money during the day and collecting it at night. It's the same exact idea of Kobe in the gym at 4 a.m. shooting free throws. We all see the end product and think, "Oh, that looks good." **Billy:** That is Seinfeld and Chris Rock. ## [01:00:07] Be Great Regardless **Jackson:** An almost inverted version of this is the idea of being great regardless. You talked about Mayer and then Harry Belafonte, the actor and then singer, where you're in the inverse situation of doing something that you don't want to be doing. It isn't the end goal, but you take it radically seriously anyway. **C:** Yeah. **Billy:** Mayer's thing is to just ace it for fun. He talked about working at a gas station when he was in high school. He knew early on he wanted to be a musician. It was hard for him, being in school and feeling that disconnect. He used the analogy of when you go to a restaurant and you know exactly what you want, but the waiter's going on and on about the specials. **Jackson:** Skip ahead. **Billy:** I know what I want. **C:** Yeah. **Billy:** "I want the burger. I don't want to hear that the lobster is cooked and put back in the shell." So he had that frustration. But he said, "Be great at whatever you're doing on the way to where you're trying to go." It's more fun to ace it than to be sitting around thinking about how this isn't what you really want to be doing. **Jackson:** And you're here anyway. **C:** Yeah. **Billy:** I just like that idea of the things that we don't necessarily want to do. The Belafonte story is a great example because you just don't know when you take something seriously who's going to see it and what opportunities are going to come along. He wanted to be an actor in the '40s or '50s, so there just weren't opportunities for black actors. He was going on auditions, and everyone said they didn't have a part. Then he goes to one where they're staging John Steinbeck's \*Of Mice and Men\*. Again, there's no part for him. But for whatever reason, the director takes a liking to him and invents this role for him, which is singing between set changes to give the stagehands more time. You can imagine being in that situation where you're thinking, "I want to be an actor, not a singer." **Jackson:** This is totally unserious. **Billy:** "The crowd's not even listening to me. They're talking amongst themselves as I'm up here singing, and this has nothing to do with the play." But the story he told himself was, "These songs are essential to knowing the time period that we're talking about here." **Jackson:** "I'm going to act as a singer." **Billy:** Yeah. "I'm not a singer. I'm acting as a singer." So he just approached it that way. One night, a few jazz men from a local jazz club came down the street to watch the play. They didn't think much of the play, but they were blown away by Belafonte's singing. They stayed after and said, "You got to come sing at the Rooster." He said, "No, no, I'm not a singer. What you saw me do was acting." They replied, "No, you're great." **C:** Yeah. **Billy:** They introduce him to the manager at the Roost, and he starts performing. Between when one band was breaking down and another was setting up, he would sing to keep the crowd entertained. He was elevated into a regular performer. One night, they were recording the live set, and it ran on some radio station. A label exec heard it, and he signed with this label. He went on to have a legendary career in music. It all started with taking this random acting role seriously. If he hadn't approached it that way and wasn't taking it seriously on the night those jazz guys came in, they wouldn't have brought him over to the club, and his career wouldn't have happened. **Jackson:** The dots connect in reverse. **Billy:** Yes, totally. ## [01:04:31] Following Up Even When Your Abilities and Standards Don't Match **Jackson:** You write about Ira Glass and his producer, Alex Spiegel, and the time it takes to get good at things. Alex was talking to Ira after hearing some of his earlier work and said, "Wow, there's no sign that you have any talent for radio. There's no sign that you're going to make it. There's just nothing good in here." Glass said, "Not only was she right," 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. Michael Lewis says, "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 liked doing it, and I was just going to keep going." He was just going to keep following up. Then there's another from 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." This sits a little bit in contrast to the idea that we enjoy the things we're good at, or at least we enjoy the things we're improving at. I'm curious for you, how do you think about purely focusing on the inputs versus actually experiencing the ramp-up and improvement and taking stock of getting better at things? Clearly, there's some value to being aware of what the market is telling you about what you're doing. **Billy:** I do think that at some point, you should start to get a little bit of feedback that what you're doing is working, resonating, or that you're improving. **Jackson:** I'm sure Ira was, on some level, not terrible. He kept the job. **Billy:** Right. **Jackson:** The funny part is she's reflecting on the Ira Glass of today, who's a master. **Billy:** Yes, right. **Billy:** It's probably overstating a little bit how bad it was in the moment because he's still in the industry, working in radio. It couldn't have been so bad that no one would give him a job. Maybe more striking was the gap between Ira Glass today, how good he is, and how long it took to get there. I remember when I was about a year and a half into working with Ryan, I was getting frustrated by the gap. were working in Google Docs where he would be drafting articles or Daily Stoic emails, and I could be in the document and see him writing. To see him write without breaking his flow—it was as if he was transcribing something already in existence. It was just coming right out of him. **Jackson:** Wow. **Billy:** And how quickly, and the quality of what he was writing. I could see that, and then I would go sit down and try to write. I was very aware of the gap between what I just saw him do and what I was able to do. **Jackson:** Totally. **Billy:** I was really frustrated by it. At that time, I had read a lot about your early inclinations being a clue to what you should do in your professional life, and early aptitude being a signal of what you're meant for. I thought, maybe this isn't it because I'm a year and a half in and it's not working. I remember having a conversation with my dad where I was thinking about quitting and going into a different line of work. He asked, "How long has Ryan been writing?" I said, "I don't know, 15 years?" He asked, "How long have you been writing?" And I said, "A year, year and a half." I played lacrosse in college, and he said, "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?" It immediately landed for me. That is an absurd comparison. It would be weirder if I was on his level. A lot of my attraction to those stories is trying to tear down this idea of aptitude and ability happening quickly being a sign to keep going. I love stories where it took longer than most people give themselves to see if there's anything there. Your attraction and your level of engagement is enough for a while. You don't have to get great. If it's engaging, just keep following it. **Jackson:** Yes. ## [01:10:10] Fending Off the Wolf at the Door (The Comfort of Success) **Jackson:** Maybe the inverse of this—one of my favorite things you've sent me is Tennessee Williams's "The Catastrophe of Success." **Billy:** Yeah. **Jackson:** 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 effete 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 acuity 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've also written 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. You've come a long way yourself, and you've also worked with some real masters, whether that be Ryan, Robert Greene, Rick, or others. Ryan has written 15 or 19 books. How do people who've reached that level of success fend off the wolf at the door? **Billy:** Keep doing the thing. Tennessee Williams was writing about when he was coming up as a playwright. He worked odd jobs, making minimum wage and writing in the margins of the day. He had a play, \*A Streetcar Named Desire\*, that was a \*Hamilton\*-type success of its time. Suddenly, everyone was wanting to do things for him. He was staying at a hotel and everyone was waiting on him hand and foot. He realized that the effort his previous life required was essential. **Jackson:** Without constraint. Constraints are powerful. **Billy:** The constraints thing. You mentioned that André Gide quote about the series of slight efforts, and no one has lived that patience quote the way he has. He has this other line about the importance of constraints in creative work and the way we romanticize a life of complete freedom to do whatever we want, whenever we want to do it. But he said something like, "Like Kant's dove, without the wind's resistance, the wings can't soar." I didn't know what he meant by Kant's dove, which was a reference to Immanuel Kant's Critique of Pure Reason. He uses the metaphor of a dove needing the resistance of the wind to fly. What I like about Tennessee Williams' "The Catastrophe of Success" is how it ties to what I'm thinking about with my work: The work is the win. I hope that book finds people that are chasing some finish line, this amount of money, or this amount of success, thinking... **Jackson:** "if only, then..." **Billy:** Yeah. One of my all-time favorite movies is There Will Be Blood. Daniel Day-Lewis's character is aggressively greedy will do anything for money and power, and he goes on this chase for those things. In an interview, Daniel Day-Lewis was talking about his character and said, "It's really about the false promise of the horizon." When the interviewer asked what he meant, he said, "You get there and, of course, the world is round. The horizon just keeps receding and receding." Ryan, Robert, and Rick all seem to still get up and do the work that they do, despite having the luxuries of financial or social resources to have other people do it or not have to do it at all. Why do they still do it? I think it's because without effort and striving, it's just the sword cutting a daisy. **Jackson:** Yes. It seems to be a much more internal thing for those guys—an internal battle. Ryan talks about reading The War of Art before every project. If it's the external thing, as you say, either the horizon will recede or it will feel like you're going through the motions. ## [01:15:55] Unfolding and Planting Seeds **Jackson:** 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 process, a budding, a flowering, an unpredictable, unquenchable unfolding." **Jackson:** You and I share an affinity for this idea. Why is it so resonant for you? **Billy:** I love your metaphor of holding seeds in your hand without ever planting or watering them, trying to figure out what these are going to become before I plant them in the ground and try to cultivate them. That tripped me up for a while. To use that metaphor, it was like holding seeds and wanting to know, "Where is this going to go?" before I would commit to it. I see it tripping up a lot of people: sitting around, thinking, and wanting to know with certainty if a job is going to lead to something or if they should go to a social event. They want the certainty of the payoff and the outcome, and they let that determine whether or not they're going to do this or that. It's also happened enough times where it would have been absurd for me to predict a lot of the best things that are now in my life. I couldn't have said, "Okay, this seed here is going to..." **Jackson:** Yeah, we were talking about that earlier. Exactly. **Billy:** Yeah. It's just one of those absolute truths: things just unfold. The time spent trying to predetermine them just creates a lot of misery. **Jackson:** Yeah. You have a metaphor from Ryan's advice about trying to plan out the full nine innings: Just throw the first pitch. That feels very similar. ## [01:18:17] Taking Initiative and Opening Doors: "He Who Hesitates is Lost" **Jackson:** I'd like to talk a bit about the thing downstream of this idea, if you really internalize it, which is actually taking initiative. I have a set of quotes. One of them resonates with what you just said, from Robert Greene on uncertainty: "The need for certainty is the greatest disease the mind faces." This is you on Hannah Arendt. "Hannah Arendt identifies initiative 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." Then I have two more quotes. "David Mehmet was asked the advice he most often gives. 'Differentiate yourself,' he said. When he auditions actors, after the third person, he can't remember the first. 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 they have to do things by the book, but there isn't any book.'" Finally, this is Jordan Peterson on Rogan: "You don't want to oversimplify things, but once you've made a decision, 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 is this confusion about acting: 'I don't know what to do. So what should I do? 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." [Joe:] "He who hesitates is lost." **Billy:** Whoa. Did I use that? **Jackson:** Yeah. **Billy:** Really? **Jackson:** You sent that to me. **Billy:** I did? Wow. **Jackson:** Where do we get initiative? How do we improve on our ability to take initiative? **Billy:** A lot of people have a sense of what they would like to take initiative on, and then they're blocked or delayed by wanting to do the pre-calculation of how this step is going to lead to that step. Somebody sent me a quote the other day from E.B. White that was, "The world is immensely complex because of course, one thing always leads to the next." When you think about one thing leading to the next, when you do that thought exercise, of course you can't know. **Jackson:** It's a fantasy. **Billy:** A big part of initiative is suspending the need to know. You and I have talked about this in the context of making contact with reality, because reality has a lot of nuance, information, and feedback. **Jackson:** Yes. This is our friend Henrik's amazing frame. **Billy:** Letting go of the need to know how things are going to unfold goes a long way. Everyone has a sense of what they would like to take that first step on, whether it's a creative project or some vague interest they've always wanted to pursue. The initiative is just to go and let go of where it's going. **Jackson:** Do you remember why or how or what caused you—what the emotion was—when you first reached out to Ryan? That was a pretty amazing gift from past you to current you. **Billy:** The subject line of that email was something like "Just Some Words of Admiration." It truly was the impulse of being a fan of his work. I found his books at a time when they were really helpful to me and had a tangible impact on my life. The impulse was pure fandom and appreciation. **Jackson:** On some level, you were uninhibited, which goes back to the beginning of how you answered that question. A lot of times we know how we feel about things, or we even know what we need to do. But we come up with all these reasons, "If I write him an email, he probably won't respond." **Billy:** There are all sorts of mind games that could have talked me out of it. I couldn't have possibly held a seed in my hand and known, "Should I send this email? I think this is how the seed's going to blossom." There were no considerations in that moment of wanting something out of the email. His reply was just, "Honored to hear my work has been helpful." It wasn't an immediate, "Yes, you are now my apprentice. Congratulations." I sent him that email, and then a couple months later, I sent him another one. Over time, it evolved. **Jackson:** A lot of times, initial initiative breaks the dam a little bit. It almost breaks the emotional dam we have. Okay, he responded. Great. I'll send him a future email if something bubbles up. Now you start to get a little downhill. **Billy:** It makes me think of that Mike Nichols thing we were talking about: little things don't carry around signs that say, "This is a big thing." It didn't feel like this was going to make or break me. It felt in the moment like just a little "thanks for the work that you do." ## [01:24:58] Stupid Bravery and Getting Past the Sewage **Jackson:** A part of this is a kind of courage. You have a newsletter you wrote that's ultimately about this John Mayer clip, but in one part of it, you're talking about Huberman. There's a clip where he's talking about getting out of the sewage before you get to the clear water. " 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've got to keep forcing it, forcing it, forcing it. You've got to get fearless, fearless, fearless." In this clip, he's sorta of Ouija boarding, like in that famous Zane Lowe interview, just ripping the song out of nowhere. And he uses this phrase, "stupid bravery." How do you practice stupid bravery? **Billy:** I do love that. It’s the detachment from... the stupidity is like... In the context of Mayer, the bravery of his Ouija boarding is that when he's trying to work on songs and doesn't have a lyric, he allows himself to say nonsense. It doesn't need to make sense. Just let things come out of your mouth. The stupid part of that is you are going to say stupid things. In my case, with writing, it's the cliche that the first draft of everything is terrible. It's allowing yourself for it to be terrible. **Jackson:** You got to write a bunch of bad stuff to get to the good stuff. **Billy:** Huberman says you got to wade through the sewage to get the clear water. And the stupid bravery is just allowing yourself to be bad and say dumb things on the way to it becoming better and better. I still struggle with this because one of the hangups on the book has been wanting to know what a chapter will be before I write it—wanting it to be fully formed in my head. And it's related to Henrik's piece about unfolding. Having that articulation has been helpful to let the writing process unfold, to let it be bad and trust that it's getting you to places you can't predetermine. It also happens all the time where, in the flow of saying terrible things, you find a phrase you didn't know was in there. Then you get something and you follow that thread. But you couldn't have gotten that phrase without the stupid bravery of letting it be stupid for a little bit. **Jackson:** Seinfeld has this frame about creating two different versions of yourself for your writing. The reader/editor and the writer are two very different demeanors. At first, you have to have this gentle, accommodating, "Great job. You're doing so beautiful." Then the mean editor can come over the top. I did this thing where I wrote 30,000 words in a month; I wrote a thousand words a day. I often tell people the hardest thing every day was figuring out what to write about. It was getting the first hundred words. If I get a hundred words, I usually get a thousand words. The single best thing to figure out what to write about, to get those first hundred words, was literally the Ouija boarding. It was sitting down at my keyboard and writing, "I am writing and I don't want to be," and just getting the wheels turning. **Billy:** Yes. **Jackson:** It's crazy. **Billy:** I do morning pages most mornings—just three longhand. It comes from Julia... are you familiar? **Jackson:** I'd never done it. But I know it well. **Billy:** The only rule is the pen can't stop. What was hard for me about it initially was not knowing the starting point. So now I do the same thing every time: the date, the time when I'm sitting down, where I am, and what I've done so far up to that point. I'm describing it. At some point, it's: " 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." Then it's, "Okay, what do you want to journal about? What's on your mind? What do you want to get off your mind?" These are literally the questions I ask. Then I will literally write, "Oh, you're thinking about this. Let's just observe. Explore this." **Jackson:** My friend Peter used to do morning pages extensively, and he would call it "unkinking the hose," which is back to the Huberman thing. **Billy:** Yes. **Jackson:** Yeah, yeah. You have this line about how you become creative by creating. It's very embedded in this. The inspiration you need is just on the other side of starting. **Billy:** Yeah, yeah. ## [01:30:16] Local Maximums and Resisting Personal "Folklore" **Jackson:** There's another related idea. I think you sent me this. We were talking about local maximums in the context of Henrik, and you sent me this old Steve Jobs video about folklore, which is amazing. He says, "Throughout the years in business, I found something. I'd always ask why you do things, and the answer you inevitably get is, '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. In business, a lot of things are what I call folklore. They're done because they were done yesterday and the day before." When you sent me that, you sent another note alongside it saying it's interesting to combine this with folklore and inertia stuff. It said, "Thinking of it as your current self being a slave to your younger, less knowledgeable, experienced self is pretty jarring." **Billy:** Oh, yeah. **Jackson:** Which is just such a beautiful way to think about how devastating local maximums can be. I have this image of being at the top of this local hill, just clinging to whatever you can find up there unless you have to go downhill. **Billy:** Yeah. **Jackson:** I'm curious if there are ways, as you reflect, that you've gotten out of personal folklore—things you've realized in hindsight you were really clinging to, or that you've observed in others. We all have it. There's global folklore in industries and the ways that we write, and we also all have these personal ones. If we were anyone other than us, it would be easy to get past these things, but we're hanging on to them. **Billy:** It may be because we were just talking about morning pages, but I did that for three years. I almost never missed a day in that three-year period, and then I stopped doing it for a while. At a point where I was getting stuck on the book project, and since it's my first book, I had decided this is how I was going to approach the process. I started doing it that way. A lot of it came from what I've observed in other authors and what seemed to make sense with my research system, so I started going down this specific process path for the book. I'm embarrassed at how long it took before I realized this isn't working. **Jackson:** We all have those stories. **Jackson:** So painful in hindsight. You see the water and you're just like, "Agh..." **Billy:** Yeah. For a year, I've been stuck and struggling with writing, and it's not working. But it never occurred to me to switch up the process. **Jackson:** Yes. **Billy:** So I went back to morning pages. One of the things I like about it is that it facilitates crappy first drafts. It allows for it. It's what we were saying earlier about approaching something thinking you're meditating versus thinking you're doing something. **Jackson:** Totally. **Billy:** This is like that. I'm doing morning pages, but almost every day something comes up that's the start of a chapter. The folklore of just, "This is how I've been doing the process for the last year," without stopping to think that it doesn't have to be this way. I arbitrarily decided on this process, acknowledged that it's not working that well, and then started experimenting with different pieces of the process. **Jackson:** I've been reading this Stripe Press book called \*The Making of the Prince of Persia\*. It's about a video game that was made in the 90s, and it's a rare book. It's literally just this guy's journals as he's making the game, when he's 22 to 26. It's the rare time where you get the process as it's actually happening, rather than the narrativization that's on the other side of success. I'm not going to say it's unbiased or objective, but the process is actually happening. It's amazing. One of the things that happens earlier in the book is he ends up spending a year distracted, working on a screenplay, and you see it happening in front of you. At one point, he has the realization, "Wait, what was I doing?" It's validating to see somebody who ended up being really successful in this project and how that can happen so easily. You feel such an idiot when it happens, but it happens to the best of us. It's slow and insidious. **Billy:** Wow, that's amazing. It reminds me of the Steven Pressfield resistance idea in \*The War of Art\*. Resistance, with a capital R, is all the various ways in which we do not do the book or the video game we're working on. **Jackson:** Yeah. **Billy:** A form of resistance is writing a screenplay instead. **Jackson:** There's a separate meta point: a great way to do really cool things is procrastinating something else. You might end up doing something great. ## [01:36:14] Some of Billy's Favorites: Ryan Holiday, Rick Rubin, Steve Jobs, John Mayer, Greta Gerwig, Jerry Seinfeld, Ralph Waldo Emerson **Jackson:** I have a fun section where I'd love to go through a bunch of people who are particular favorites or influences of yours. I'll start with the most obvious, which is Ryan Holiday. A couple of things I wrote down: "All success is a lagging indicator." "Creativity is a function of the previous work you put in." More broadly, he's somebody you've spent an immense amount of time with, an apprentice under. I'm curious what most immediately comes to mind when you think about him and his influence on you. **Billy:** This is always hard because when I think about the things I do on a day-to-day basis, almost all of them have been informed by observing Ryan go about his work and his life in a very tangible, hands-on, pragmatic way—not an ideological way. For example, I sit down and read first thing in the morning, I make notecards, and I see a story in one place and want to find it everywhere. That's one of the things Ryan always does. If you read a story told in one Churchill biography, he wants to find everywhere the story is told, triangulating and following those threads. I stop and go for a run in the afternoon. These are just very practical habits and routines that were all picked up from him. I started the notecard system because I read his article about it before meeting him, but then I got to see with my own eyes how he goes about his work. One of the interesting things about him is that if I didn't see him on a day-to-day basis, I would think he's always at his computer or reading a book. He's so prolific that it seems like he must never leave his computer. The reality is he spends a couple of hours in the morning, then he's outside with his kids and takes them for a walk. Then he comes back and works a little more, then he's out on the back porch having lunch with his family, and then he comes back in and does a little more. One of my big takeaways from him is day-to-day consistency. It's not about spending 20 hours a day killing yourself. His phrase is "small contributions." Make small contributions every day, and if you do that over time, it becomes pretty drastic. **Jackson:** Tim Urban talks about this. The best great writers are not the people who have these crazy days; they're the ones who write every day. A little bit every day. **Billy:** He's really informed for me the idea of small contributions and letting that compound over a long period of time. The first rule of compounding is not interrupting it unnecessarily. He's also done a really good job of not interrupting his process, not jumping on the new format that every creator is jumping on. He's been so consistent for 15 or 20 years that his output seems insane. But it's because there are 20 years of those slight efforts—a series of slight efforts every day. **Jackson:** If you want to understand how this magic trick happened, look at the process, look at the machine. **Billy:** It's so hard to quantify. When I think of the way I was living previous to finding his work, and then later meeting and working with him, it was like two different people. **Jackson:** Another person is Rick Rubin. One idea from Rick: "I never try to judge an idea based on the description of an idea. Always musically try the idea." This relates to our and planting idea. On that note or otherwise, does anything particularly stand out from the time studying and working with Rick? **Billy:** One interesting thing I've noticed after working with him for about two years is that not once have we talked about or has he had me look into something music-related. It's all outside. I see a very small part of his universe and what his life actually is. But in my experience, the things we've worked on that he's had me look into and track down have been incredibly diverse and vast. I've taken the lesson of being curious and interested in learning about all different sorts of things, and they find their way into music or a book he's working on. I have found it interesting, the genres of things he's consuming—the clues he's gathering and letting into his process. **Jackson:** What do they say? If you want to produce something unique, you need to have unique influences. What do you love about John Mayer? A frequent mention in the Six at 6 Newsletter. **Billy:** I love the way he articulates things and the way he thinks. In interviews, it's like a peek into his brain working in real time. He doesn't have his greatest hits of things he wants to talk about. He's Ouija boarding in his interviews. The analogies and the metaphors he uses are great. He has a comedic ability, like my favorite comedians, to articulate something you walk by every day. They articulate it in such a way that you realize it happens all the time, and there's humor in that ability to observe and articulate. Mayer does that a lot with his use of analogies and metaphors. I also love his utter dedication. From what I've read, his dedication to studying the craft of music and studying the greats that came before him is clear. He started learning the Grateful Dead catalog prior to playing for Dead & Company. It was just this instinct of, "I love this music. I want to know it." **Jackson:** By the way, he discovered it in 2010. **Billy:** Right. **Jackson:** He was already way successful. **Billy:** Yes. Yes, exactly. From what I can tell, his approach to his craft is really admirable. The way his mind works, I find interesting. **Jackson:** Steve Jobs. We were talking about this this morning. You were joking that it's cliche, like, "Oh, you're going to tell us another Steve Jobs story?" We had a fun conversation about how he's still underrated. What do you admire about him? **Billy:** He's another great communicator and user of metaphors and analogies. He's also one of the greats at making complex things and getting to the essence of what they are. In that \*Make Something Wonderful\* book, he's talking in 1985, so computers haven't yet hit the mass market the way they're so entrenched in the world today. They were coming, and there were fears similar to today's fears of AI—what it will mean and what it is. Steve Jobs had this great thing about computers: 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, and came back in the snap of a finger. You would think I was a magician, but I just did a basic series of steps really fast. I walked over there, grabbed the bouquet, came back, and snapped my fingers. I often have the experience of him articulating something that helps me make sense of things, better understand them, or become less fearful of technology. That's what comes to mind. **Jackson:** A technologist who really deeply cared for communicating simply, which is rare amongst anyone. What about Greta Gerwig? This also came out this morning. **Billy:** I love Greta Gerwig. We were talking about the affinity for somebody increasing once you get to know their story or hear them talk. This was my experience with Greta. I had seen \*Lady Bird\* and \*Little Women\*, and I loved \* Lady Bird\* especially. That was the movie where I did what I often do: ask, "Who made this?" and then go pull the thread and read about them. One of my favorite stories I've read about her is that she had this vague sense of wanting to be a director in seventh grade. She tried to direct a school play and got made fun of for being the "bossy girl." She was so bullied in that experience that she stuffed down this inkling of wanting to direct. Not only that, but she receded into the background to not stand out and expose herself to the possibility of being made fun of again. **Jackson:** It's pretty amazing too, that she literally went on to be an actor, which is arguably more in the spotlight. For her, there was some version of that that was like, "This is the thing I can't do." **Billy:** Yes, that's what I was going to say. Instead of directing, she thought, "I want to be in this world, so I'll act and let people tell me what to do." **Jackson:** Wow. **Billy:** And so she spends 10 or 15 years. **Jackson:** Frances Ha, by the way, amazing Greta performance. **Billy:** Yes. She spends the next 10 or 15 years stuffing down this sense that maybe she would want to try this thing. She tells the story of being at a party where this woman, Sally Potter, another filmmaker, was there. Greta went up and was asking her about acting, and Sally stopped her and said, "You want to ask me about directing." Greta asked, "How can you tell?" and she said, "It's written all over you. You have to do it." **Jackson:** Whoa! Oh, my gosh. Wow. **Billy:** great for that to happen, but then Greta did something about it. She wrote what became... **Jackson:** The world sometimes slaps you in the face with a hint. **Jackson:** And then you still don't do anything about it. **Billy:** She said that happened with Sally Potter, and then another director gave her shoes. If a director gives you shoes, it means you're next. She was telling that story, and the interviewer said, "All these things were happening to you. This doesn't happen to everyone." She replied, "Yes, they were happening, but I was looking for them." Then she did something about it. She wrote \*Lady Bird\* and then directed it. That initial attraction to the movie \*Lady Bird\*, and then learning that about her, made me so admire her and her career path. Another aspect of why she was putting off directing was the mythology around directors—that they are these big, brash personalities who have been obsessed with movies and cameras since they were three years old. She felt that wasn't her. She wasn't that personality and wasn't the kid obsessed with movies at an early age, so she didn't think she had the personality for it. Then she ultimately attempted to do it, and in hindsight, she learned you're not born with the personality. It's in the making of movies that you develop a certain personality. The idea of using early inclinations and ability as a clue to whether something is in your DNA or not is a hoax. It's in doing the work that you develop. You don't have to have the Steven Spielberg story of coming out of the womb with all the signs of being a great director. You can develop it. **Jackson:** I think it's in that same newsletter about Greta. You have an excerpt where you're talking about David Whyte and you say, "No one is born with a certain personality hardwired to be a director, a radio host, a writer, a standup comedian, or a gang member. It's like anything else. Where's your follow up? There's your personality, filed 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.'" It's powerful stuff. **Billy:** He goes on and says you should ask what you're doing in the hours of the day. **Jackson:** What are you harvesting? **Billy:** He's saying it's not a passive process. The things you're spending time on are working on you. **Jackson:** One of your favorites, and mine, is 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." What about any of those, or about him? **Billy:** I think the through-line is humanizing great artists and creators, and the many years and slight efforts that accumulate in someone like Seinfeld. Regarding "All art is disguising work," he was saying that some other comedian said to him, "Your whole act is a tremendous amount of work to make it look casual." From what I've read and interviews I've listened to, my surface understanding was that he just had some sort of natural comedic gene. But to learn that he's put tons of time and effort in, and thrown thousands and thousands of jokes away to make it seem like **Jackson:** It's easy. Find the torture you're comfortable with. Find the struggle you're comfortable with. **Billy:** He was describing what he does all day. It's just sitting down with a yellow legal pad, working on jokes, throwing stuff away, and playing with ideas. The person said, "That sounds like torture." And he said, "Your blessing in life is when you find the torture you're comfortable with." **Jackson:** Back to the boring. **Billy:** When you describe the things do to somebody, they say, " That sounds exhausting or a waste of time or frustrating, monotonous." But if you say, "No, I like it," that's probably a good sign. **Jackson:** I have a couple of 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, "I cannot remember the books I've read any more than the meals I have eaten; even so, they have made me." I don't have a question, but that's very cool. It's very cool to discover that through you and also see you in those quotes. **Billy:** What was the first one? **Jackson:** "Many times the reading of a book has made the fortune of the reader, has decided his way of life." **Billy:** It's similar to the Joseph Campbell thing of reading as a divining rod. There's the great story of James Cameron going to the USC library and just reading and stumbling across some obscure film technology PhD thesis. For whatever reason, he found it really interesting and followed that interest. In that, he discovered he had an interest in filmmaking. It was a divining rod—this initial interest discovered in a book and then pursuing it. That's been my experience of books: discovering interests and following them. I couldn't imagine what I would be doing if not for the guidance of so many books and being introduced to ideas and interests. It makes me think of Henrik's idea of unfolding. I think he has something in that piece about reflecting on how your favorite books became your favorite books, or your friends became your friends, or your favorite food became your favorite food. It was just stumbling on something, and then following through on that and learning more. **Jackson:** It's following the clues. **Billy:** You just can't predetermine or know beforehand what those things are going to be. ## [01:56:45] Side Quests **Jackson:** I have a few final questions before we wrap up, across some miscellaneous topics. You were a ski bum for a little while across different parts of the world. You've talked about side quests broadly. Why are side quests worthwhile? **Billy:** My ski bum few years was a classic cliche: I didn't know what I wanted to do or who I was, and I wanted to get out there and discover that. It was also rooted in the "find your passion" type books I was reading at the time. My interpretation of the "find your passion" thing was that you're a key and there's a keyhole out there, and you have to perfectly match those things. **Jackson:** As Henrik says, "the opposite of unfolding is a vision." **Billy:** Yes. **Billy:** For whatever reason, I had to go out and find this keyhole. I also remember reading about the idea that nobody actually likes to work or make lots of money. What they want is what they think those things can uniquely afford, which is complete freedom. The freedom to live in ski chalets and on the beachfront. So I thought, I'll just— **Jackson:** Skip to the freedom. **Billy:** I'll skip to it. I'll go be a ski instructor and do the bare minimum—meet the quota of ski instructing days, but then just ski. For my first year of doing that, I thought, I've unlocked the secret of the universe. This is what I'm going to do forever. **Jackson:** Be without obligation. Right. **Billy:** It was like the sword cutting daisies. It ultimately got to a point where I was just sad. I wasn't happy. **Jackson:** Totally free and without meaning. **Billy:** Yeah, there was nothing. I wondered, did I make a horrible mistake? Now I'm two years behind all my college friends who are on more traditional career paths. That was the time when I discovered Ryan's work. I was struck by a story of him leaving Hollywood. He was working in Hollywood when he first dropped out of school, and he left that job to be Robert Greene's research assistant. I remember being struck by not only the pay cut I imagine he was taking, but also losing the status of "I work in Hollywood" and replacing that with, "I am a research assistant for an author you've probably never heard of." When I first met him in person at a conference where he was speaking, I asked him about it. He said that he looked around at the people ahead of him in Hollywood and what they spent their time doing. Then he compared that to what Robert spends most of his time doing. He even called Robert, and it went straight to voicemail. He thought, "He's writing, he's reading, he's making notecards. That's probably what he's doing right now." Robert's life resembled what I wanted mine to look like. Conversely, I didn't want to spend my time doing what the people 10 and 15 years ahead of me in Hollywood were doing. There was no amount of money or status that could fix being miserable all day long. **Jackson:** Yes. **Billy:** At that time, I was still doing the ski stuff, and it forced me to look at the instructors and other resort employees who were 50 and 60 years old. It really scared me to think that could be me one day. I would look back and realize I just spent 50 years skiing every day. That began my shift from thinking I'd solved the universe by skiing and not working at all to making my way towards doing work. It's not all bliss all the time; it can be frustrating and monotonous and tedious, but there's still the reward of it. I have mixed feelings about my years as a ski bum. **Jackson:** Will you still tolerate side quests of any kind? **Billy:** I think so. It's the idea of taking initiative on these little inklings of things that might be interesting, not completely writing that off. That side quest was really about wanting to have no constraints—to just be totally free and do whatever I wanted, when I wanted. I'm definitely learning from that. It took me to a pretty dark, miserable place. ## [02:02:26] "I Know What We Do Here" and Creative Environments **Jackson:** One of my favorite newsletters you put out was on the phrase, "I know what we do here." Why are our environments, especially physical environments, helpful for creativity? **Billy:** The "I know what we do here" idea came from Seinfeld. Another comedian was saying to him that he had been struggling to write and develop new material, and Seinfeld asked, "Where do you work?" He said, "I have an office at home." So his kids are there, his family's there. He didn't have undivided attention. It was his office, and there were no boundaries around it. **Jackson:** So, constraints again. **Billy:** Yeah. Seinfeld told the guy, "I assume they're paying you to do this. Take the money they're paying you and get a little shack somewhere. It doesn't have to be crazy, just a little writing spot that's yours. And when you walk in that door..." **Jackson:** I know what we do here. **Billy:** I know what we do here. **Jackson:** Yes. **Billy:** He talks about treating your brain like a dog you just got. **Jackson:** I love this. I love this. Sad little dog. **Billy:** Yeah, in the way of training it: "This is where you eat. This is where you do your potty. When you're here, you just sit here and you do nothing." I do think the brain is pretty good at getting habituated to environments, especially once you train it. **Jackson:** Right. **Billy:** Yeah. And it doesn't have to be physical. I'm thinking of the morning pages, where that sparks a sort of, "I know what we do in this journal." **Jackson:** Yes. Yes. Yeah. Even in that newsletter, you had one about James Cameron having two different desks while he was writing Terminator and some other movie. **Billy:** Yes. **Jackson:** Yeah, and he literally had the desk separating the different movies. **Billy:** Yes. One was for Terminator; I can't remember the other one. He had a tight timeline to finish them, so he came up with this idea of the two desks. You get primed and you're able to more quickly drop in. **Jackson:** Change context, change gear. I have a group I go to on Wednesday mornings to write for an hour. I do not write very consistently in my life; I just write in that session. Yet when I'm in that room—it's this little greenhouse in a backyard—it is so easy to write in there. It's automatic. It's powerful. ## [02:05:28] Bringing Familiar and Unfamiliar Together **Jackson:** Why is it so powerful to bring familiar and unfamiliar together? **Billy:** The idea of combining a known and an unknown, or something familiar with something unfamiliar, is captivating for an audience. If I think of some of the stuff that has gone the most viral that I've posted on social media, it usually has this element of known and unknown. There's a story of Tom Hanks when they were making \*Forrest Gump\*, and I told the story of how he came to way he speaks in the movie. **Jackson:** Right, with the kid. **Billy:** That's a very well-known movie, character, and voice. Everyone can think of that \*Forrest Gump\* voice. The unknown was how he came to it. **Jackson:** Everyone has a touch hold there, a point of entry. **Billy:** There's this paper I read not too long ago about motivation theory. The sweet spot is something that's not too hard and not too easy. If you're playing tennis with a four-year-old and you're just dominant, you get bored. **Jackson:** Or a video game. Video game designers are really good at this. They're good at making it get harder as you improve. **Billy:** There's a sweet spot between it being way too easy and it being impossible or pointless. And there's something similar with a sweet spot between, "This is so obvious, it's boring," and "What even is this?" **Jackson:** "You've lost me." **Billy:** When I reflect on some of my favorite reading experiences, it usually has that element of slight familiarity with, "I've never heard it put this way," or "I've never heard this story about this person." I like it as a reader and a consumer, and then it's fun to try to bring those elements together in the writing as well. **Jackson:** You said, "I found a really great idea, and now I have to execute on it." That was regarding the book, I think a year or two ago. **Billy:** I said that? **Jackson:** Yeah. What does that feel like? You were speaking about the opportunity and the burden of having found something and knowing when it's actually ready or done. **Billy:** It makes me think of the Hannah Arendt quote that you mentioned earlier about taking the burden. Everything that is in existence, somebody took initiative. They took the burden of labor and toil upon themselves. There's the great excitement of the spark of an idea that you can imagine would be a great chapter. And then the work of bringing it into existence is a whole other thing. What immediately follows is, "This is something," and then, "I know how long it takes to write a chapter, so we've got our work cut out for us." ## [02:09:26] Mastery and Compounding **Jackson:** There's an amazing quote about this designer. You say, as Scher got up to leave the room after 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." On the other side of what you were just describing—the arduous process of creating that you've observed in others or found yourself in—what does it feel like when you can pull on the work you've done in the past? In many ways, you're doing this with the note cards in the newsletter. This quote is pointing at what we've talked about: the four stages of competence. Unconscious incompetence, conscious incompetence, conscious competence, and then finally the unconscious competence, the mastery. If you ask a true master how they did something, a lot of times they're not even sure. They can't explain it to you. I'm curious if there's been any ways that you felt that or that you've gotten to witness it in others. **Billy:** I don't think I've felt the experience of Paula Scher. She was hired when Citibank and Travelers were merging, and she was brought in to create a new logo. It was going to be just "Citi," and she drew it on a napkin. That's what the Citi logo is to this day. I don't think I've ever had the experience of it happening fast and easy. **Jackson:** Right. **Billy:** For me, it's more the joy of it. This piece has stories in it that I've been collecting for three years. I didn't know when I was going to use it, but I experience the work of my past self having put in the time to read the thing or make the note card more than I experience the artist who's lost in the flow of mastery over their craft. I don't think I have the mastery of craft to tap into that. It still feels very conscious. What were the stages? **Jackson:** The first one is ignorance: unconscious incompetence. Then awareness: conscious incompetence, when you realize you're incompetent. Then learning: conscious competence. And then finally, mastery: unconscious competence. I feel like you're in number three. **Billy:** Three, and then also sometimes two, where I'm aware that this is not good. **Jackson:** Fair. **Billy:** But also three. Conscious that this is good because there are many years behind this good thing, and I like that. **Jackson:** I've done the work. ## [02:12:44] The Real Life of Appearances **Jackson:** I want to read an excerpt from Robert Henri's \*The Art Spirit\*, which you sent me. "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 tools 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 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 line in the margin on that one is, "The real life of appearances." Why did that quote stand out to you? **Billy:** That was... I was draw to... **Billy:** The real life of appearances we've been talking about is when something seems to be magic, lofty, or the result of innate talent. But when you peel it back, you find a lot of work and years went into making it appear that way. Tom Hanks tells a story of meeting Joe DiMaggio at a restaurant one night. The waiter came over and said, "Hey, Mr. DiMaggio wants to meet you." Tom Hanks goes over and they have this conversation. Tom Hanks made a comment about how DiMaggio made it look easy out on the baseball field. He leaned in and said, "There's a lot of f\*\*\*ing work to make it look that easy." I did a newsletter on the Joe DiMaggio principle of those that make it look easy. **Jackson:** That's like the magician. **Billy:** Yeah. It's so similar. The real life of appearances. Things that look one way or seem effortless, or they're just a natural—there's usually a real life of knowledge, information, and practice under that appearance. ## [02:15:43] "Ton-goo-ey" and The Gifts We Give Ourselves **Jackson:** I have one last question. We were talking about this a bit with Greta Gerwig and in a whole bunch of other contexts. There should be signs early on in your life that you are inclined towards a certain thing. You used the term, "For me, writing should have probably been off the table." Can you tell the story and reflect on where you've landed in your life of "ton-goo-ey"? **Billy:** Yeah. Wow. I think it's probably my earliest memory, and it's definitely my most vivid. I can still close my eyes and go back to the room and the chair I was sitting in when I think about this story. I was in second grade, and I was really struggling and slow to learn the alphabet, words, vocabulary, and spelling. It was recommended that I start seeing a specialist at the school who worked out of one of those trailers detached from the actual school. I would walk over, and kids are on the playground, and they know why you're going in there. It's the walk of shame. In one of the first sessions with her, she put a sheet of paper in front of me and read this list of words to me. I get a third of the way down, and I get stumped by a word. She's like, "Just sound it out." And I said, "ton... ton-goo-ey?" And she goes, "Tongue." Immediately, I was so humiliated. I can still feel that feeling. **Jackson:** Yeah. Oh, man. The things that happen to kids. Talk about the things that stick with you. **Billy:** I remember reading a lot of those books about early inclinations and early aptitude being signals to follow what you're meant to do. There was a time when I read those books that I would sift my memories for what inclinations and aptitudes I had. I would always first think of the ton-goo-ey story. Okay, not words. Nothing to do with spelling, clearly. It's why I resonate with the Greta Gerwig thing: you're not born with this personality. It's developed, and it's through doing the work that you can develop the personality. I now think on that story fondly, like the Henrik's third chair essay. It's one of the most beautiful, total-chill pieces of writing I can remember reading recently. He talks about going to this library where he spent years wanting and struggling to be a writer. Now, however many years later, when it's starting to happen for him, he walked in there. The feeling that 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. His appreciation for this person, this past him that stuck it out. **Jackson:** Who was feeling so lost and unmotivated. Why am I even doing this? A waste of time. **Billy:** And that present-day him that is getting to do what that person wanted is just being like, thank you for your persistence and for showing up when it was a struggle, frustrating, and lonely and you didn't know. Having gratitude for that person. The piece ends where he says, "And then I turned around and there was a third chair." I remember reading that and I got chills and was almost teary-eyed thinking of the version of me that did Hooked on Phonics and worked on figuring out how to spell and on vocabulary. Now my day is filled with **Jackson:** Reading and writing. **Billy:** Yeah. With those things that took a long time to develop and cultivate. Some past versions of me showed up and did those things. **Jackson:** Thank you, Billy. **Billy:** Thank you.