Technology, Connected - Bruce Lee Put the Zen in Self-Help | Jeff Chang

Episode Date: October 10, 2026

Bruce Lee’s ghost influences us like very few others. Bob Marley, Muhammad Ali: these are the icons his legend walks with. In Water Mirror Echo: Bruce Lee and the Making of Asian America, Jeff Chang takes us inside kung fu, mindset and movies. In the second part of the show we get into AI and the creative act. Does Chang use AI? How about his friend DJ Shadow? (00:00) Bruce Lee, AI and the first draft(02:06) Who was Bruce Lee? (05:15) How Bruce Lee made Zen pop culture(10:05) Bruce Lee's letter to himself and Napoleon Hill(15:33) Bruce Lee's parents and wartime Hong Kong(18:37) Seattle, racism and the cha cha(21:19) The Big Boss, Fist of Fury and Enter the Dragon(28:17) Be water: Bruce Lee's mantra and the real fight(32:21) Water, mirror, echo: the meaning behind the book title(34:25) Does Jeff Chang use AI? (40:24) DJ Shadow on AI, sampling and Endtroducing(48:26) Auto culture: could you love art made by a machine?(54:28) Punch me: Bruce Lee's single-mindednessHow do you explain Bruce Lee to a 20-year-old who has never heard of him? Chang starts with John Wick and The Matrix: “he’s the guy that made all of that possible.”Stay with us and you'll learn:- How Bruce was a war baby in occupied Hong Kong, child film star and cha cha champion before being sent back to America at 18 to wait tables and learn about racism in Seattle- About his role as Kato in The Green Hornet, and the letter he wrote himself at his lowest point, promising world fame and $10 million- What's the difference between The Big Boss, Fist of Fury, Enter the Dragon.- How Jeff and is old friend DJ Shadow use AI. Or don't.Please enjoy the show.---------------📚 Jeff Chang’s books: https://jeffchang.net/📷 Jeff Chang Instagram: https://www.instagram.com/zentronix🖊️ Substack: https://zentronix.substack.com/----------------🌐 Thinking On Paper: https://www.thinkingonpaper.xyz📷 Instagram: https://www.instagram.com/toptechpodcast/🧭 Choose your own technology adventure: https://www.thinkingonpaper.xyz🎧 Listen on Spotify: https://open.spotify.com/show/00volKqMsQntToeho35W47🍎 Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/thinking-on-paper-technology-considered/id1713227258#BruceLee #JeffChang #ThinkingOnPaper 

His thought was that the purest fight is one in which somebody's going to be dead at the end of it. That's why he didn't like contests. He thought they were simulacra. He thought they were fake. He thought they were just copies of what the real struggle was about. Similarly with Bruce, you know, he's somebody who's of Asian descent. He's living in the U.S. He's learning about what it means to live in segregated, racially segregated neighborhoods.

That's how he actually becomes American, as he learns about racism. The reason that we can even talk. You know, me on The Daily Show talking about moments of Zen is like down to Bruce Lee, really, you know. I don't think that you have that stuff going pop outside of what he's injecting into his movie, Enter the Dragon. AI is a very poor writer because it doesn't have the quirks of the human mind. I'm going through a million prompts in my head to get from draft one to draft one and a half. And that struggle is, it's the worst thing in the world and it's the best thing in the world for me.

I don't want to give up the best thing about it, but I know that I'm going to have to go through the worst thing about it. Just like training, right? Just like Bruce used to do whatever, a thousand sit-ups a day. Disruptors and curious minds. Be like water, my friends. Today's guest is Jeff Chang, author of The Quite Fabulous Bruce Lerner. and the making of Asian America, Water, Mirror Echo. You might have seen his work in his other book, Can't Stop, Won't Stop.

So hip-hop and Bruce Lee today, we're going to learn about the real Bruce Lee, about Hong Kong and his background, the people in his life. And then we're going to end the show, learning how Jeff thinks about artificial intelligence and the creative act. Jeff Chang, welcome to thinking on paper. Thank you for thinking on paper with us today.

Thanks you guys. It's so nice to be here. I'm super happy to be here with you all. Thinking on paper and aloud. Imagine you go to a party. You meet a 20-year-old. They might not have heard of Bruce Lee. Some people won't have. Where in that situation?

Where do you start the story? How do you convince a 20-year-old to jump down the Bruce Lee rabbit hole and go and watch Enter the Dragon? Go and watch Big Boss. Go and learn about him. Where do you start the story? Wow, that's a great question. And it's actually come up quite a bit.

You know, there's a lot of young folks who are like, who's Bruce Lee? And I'm always taken aback by the question. But I'm like, you know, John Wick? You know, have you seen John Wick in The Matrix? And they may not even recognize, you know, the Matrix and that kind of thing at this age. But I'm just like, he's the guy that made all of that possible. You know, he's the guy that brought in Asian martial arts into the, the center of the action film.

He's the guy that was, he sort of put Asians on the map in terms of Hollywood and in terms of thinking about popular culture globally. Let's say there was something called the Bruce Lee Way, the philosophies, the things that extend through time. And you have 25 minutes

with the generation that we're talking about. What does the syllabus look like for that. Oh, wow. That's such a, that's such a great question. And I'm also, I'm also thinking that way these days because I'm going back into teaching in January. And so my mind is getting back into into pedagogical things, so to speak. But yeah, I think it, it has to do partly with explaining what it means to be an underdog, you know, to be somebody who, who comes from way outside and the fight that they need to take, the fighting path that they need to take in order to kind of get seen by the mainstream.

And in some ways, that's really the fundamental story of all of my books. I've realized, looking back, you know, from Can't Stop, Won't Stop, these kids in the Bronx that were abandoned and forgotten and how they come to change the world. And similarly with Bruce, you know, he's somebody who, who's of Asian descent. He's living in the U.S. He's learning about what it means to live in segregated,

racially segregated neighborhoods. That's how he actually becomes American as he learns about racism. And he also learns about the sort of American dream, the ideal of the American dream, you know, that people can pull themselves up by their bootstraps and that they can will themselves, right? They can sort of think themselves through

to prosperity and success. and fame and fortune, right? That's a very American idea, right? And so to be able to kind of talk about how all these things come together, how Bruce puts it all together, and is then able to popularize Asian fighting arts, but also Asian philosophy. I mean, to me, he's probably just as great,

a popularizer of Asian philosophy as some of the, you know, the beatnik poets or Alan Watts. who was influencing the beatniks themselves. And, you know, he's... That was my brain a lot. Yep. And so the reason that we can even talk, you know, give me on the Daily Show,

talking about moments of Zen is, like, down to Bruce Lee, really, you know? I don't think that you have that stuff going pop, like, outside of Bruce's, you know, what he's injecting into his movie, enter the dragon, you know, at the end of his life. And then subsequent to that, I think, There's been a lot of sort of focus, I think, primarily by Shannon, his daughter, on Bruce's, Bruce's, you know, they call it teachings, you know, it's sort of the way that he brought these philosophies together of

of Eastern philosophy with, you know, this sort of American thing of like, you can do this, right? This idea of self-actualization is what he called it. is something that I think is very much mainstreamed now. It's very much a part of the self-help industry, the happiness industry, the, you know, all of these industries. But, you know, but also just a part of this idea in this era, too, of when we talk a lot about trauma, of how you can work on yourself. You can continuously self-improve and you can continuously move to being a better person. So it starts with the movies and it starts with all these things that literally have to do with like just punching somebody or kicking somebody. And

then it expands to these fundamental ways that we actually think of ourselves and how we live in this racial capitalist society. It's a pretty big story in that kind of a way. So if I could fit all that into 25 minutes and make it interesting, I might have a good class. We have the tenacity and grit aspect of this, this perseverance, this is one of the key fundamental aspects, I think, to having a meaningful life, a life with purpose, is to kind of harness that ability. And then there's this mindfulness aspect, this accessible way to get into some of those theories and philosophies, I think. Is it fair to say? Absolutely. I think that, You know, he was very much a popularizer.

That was who he wanted to be. And in the magnetic performances that he has on screen and in his untimely, very premature death, a lot of that stuff then becomes much larger. It's elevated. And I think what's interesting to me is you mentioned Steve McQueen. Like, we don't actually talk about Steve McQueen. in the way that we talk about Bruce Lee all around the world these days, right?

Like, again, a certain generation of us is like, Bullet, oh, yeah, that's the guy, right? Like, Steve McQueen, but he's not thought of and talked about, you know, from here to Asia, to Africa, to Europe, all around the world, like we talk about Bruce Lee. And, and, Bob Marley is perhaps the only of the one who does traverse the world

that way. I think so. Muhammad Ali, Bob Marley, yeah, folks of that kind of caliber, it comes from who he was as an outsider, as an underdog,

as somebody that we can all believe in, as somebody who's five feet seven, right, five feet eight maybe in tall shoes, and he's like 120 to 130 pounds most of the time. And yet he's

taking on, you know, Kareem Abdul-Jabbar and Chuck Norris. So, like, we all can imagine ourselves when we see Bruce move. And I think that in that regard, you know, his story becomes something bigger, but all of the stuff that comes with it, right? The, the philosophy, the ideas that he was messing with, he was an inveterate reader. And how he actually simplifies this and makes it palatable to mass audiences, that is all part of the way that Bruce's image continues to grow and expand

in people's minds and imagination. The thing that really excited me about getting this opportunity to do this book was thinking about how Bruce has been, the image of Bruce has transformed from generation to generation. Every generation finds their new Bruce. I want to read the quote that you wrote in the book about his letter he wrote to himself.

I, Bruce Lee, will be the highest paid Oriental superstar in the United States in return I will give the most exciting performances and render the best of quality in the capacity of an actor. And starting in 1970, I will achieve world fame and having my possession $10 million. So he was very much into that. Okay, I'm going to do this. I'm going to visualize and I'm going to get there. So yeah, he really was a foreruner to the self-help, to the mindset, to the mindfulness, to the meditative industry that is so popular now.

He wrote that at the bottom of a period in which he thought that he wasn't going to be able to ever work again. 969 was it? Yeah. You know, he's really struggling in Hollywood because they don't see him, they see him as an Oriental. They don't see him as a full person, right? They don't see him as what we name ourselves later on, Asian American, right? Or actually it was happening simultaneously to that, but he wasn't, he didn't have access to those radical sort of identity. movements because he's working in this Hollywood bubble and he doesn't think that he's ever going

to be able to regain stature to get another part after he had been the co-star, the number two, on this national ABC TV show called The Green Hornet and he was like the sidekick, Cato. And so he thinks he's never going to be able to get there again. And so he draws on, and this is sort of going back to what you're talking about, right, Mark, in terms of somebody who is constantly absorbing forms. And whether they be martial arts forms or whether they be the form of this American self-help philosophy, right? That's literally an exercise in a book by this guy named Napoleon Hill, right, who writes these books about, like here's how you become rich and here's how you become successful. You will it from your head.

You say, this is what my chief objective is. My great aim is going to be. My chief aim is going to be. And you write it in a paragraph in this format, right? And he literally writes it in the format that Napoleon Hill dictates. He's learning the form. It's just like a martial arts form, like learning how to block, right, or something like that or learning how to counterpunch or something.

This is like him learning the American form of self-actualization. Napoleon Hill thing is such an interesting poll here because that book was written in the 40s or 50s, I think, right? And he was pushing stuff out into the ether as barely digestible like 10 years ago. Like, holy cow. And the one thing I pulled from this book, I'm not sure if you read it. A thing can grow rich, I think is what it's called. That's exactly.

Yeah. So there's a three or four pages that talks about this idea, this council of invisible advisors, which basically he sits at a table and he goes, pretends Thomas Edison's there, pretends Andrew Jackson. I'm making up these names, right? No, yeah. But this is all right. Yeah.

He has a conversation with himself through these personas. And it like that blew my mind and I start I've done stuff like that and it's really powerful But I didn't know Bruce Lee was kind of like motivated by that and your framing of it as a A martial art per se as a as a as a way a system for him to understand and apply really cool man I think that's how he thought about it you know I think that he he's trying to absorb all the tools that he can to better himself To make himself able to to move through situations and conquer all and so I think that he's He's absorbing this in the same way that he's absorbing Asian philosophy, right? The connection that he makes for himself.

He wasn't just basing, because Napoleon, wasn't he, I mean, his Wikipedia says he's a conman, so I'm sure there was, you know, very well versed. And this is part of the self-help industry history, right? It's the, it leads all the way up to the prosperity gospel, right, that we see now. and Donald J. Trump, right? The art of the deal, right? This is, it's a very deep sort of ideology within American culture. And so, you know, this is Bruce picking up all the tools that he can to basically figure out how to better himself.

So he writes this at a point in which he thinks, I'm never going to be able to get these jobs. But, okay, wait, maybe if I get this tool, that will help me to unlock things. And two years later, three years later, he decides, I'm not. not going to be able to do this in Hollywood and he has to go back to Hong Kong because they don't see him like he sees himself. He sees himself as a main character. They see him as a sidekick, you know, something just a little bit higher than a coolie. And, uh, but this is part of who he is. He's constantly evolving. He's constantly bringing these things and he's constantly absorbing all of these different types of things that he, he hopes will be able to help him

through all the battles that he faces in life. Reading the book, I know, there was two, in the early days of Bruce Lee, there was two things which were the foundation of the beginnings of where he went. That was Hong Kong and that was his parents. Could you speak to the role his parents played and then the role that Hong Kong played in? Sure. Well, first of all, Bruce was born in US citizen because he was born in San Francisco and

it was an accidental birth. not accidental I mean it's a birth but his parents had gone to the U.S. as the Japanese are moving through and occupying larger and larger

parts of China so they're concerned about the clouds of war gathering outside of Hong Kong not too far away and they're like we're going to have to stash them anyway his father is a Cantonese opera singer one of the most famous and so he

is invited to do a tour of Chinatowns in America. And they're like, this is great because this will allow us to be able to stash some money and be able to make it through the war. We'll have stuff for our growing family. And his mom gets pregnant. So Bruce is born in the U.S. But they move back to Hong Kong. And almost as soon as they move back, the Japanese invade Hong Kong.

And so he's a war baby. He's literally somebody who is buried. surviving the war period because he, like everybody else in Hong Kong, who are not, you know, the occupying army, are starving. And he's very sickly. He's very weak as a child. But then when the war ends, his parents, his dad, especially, is now in a position to move into the growing Hong Kong film industry, becomes a huge star. And so Bruce follows and becomes a baby, a baby actor. and then a child actor and becomes a star in Hong Kong as it's figuring out its identity. And so Bruce plays like this, you know, orphan, which is sort of how Hong Kongers see themselves during the war.

And I think that, you know, that's a deep part of who he identifies as, right? He's actually of what relative privilege, he's going to private schools and he's not doing so one of these schools. but he and his he and his mates are after school like walking up to the British school and like trying to get in fights with them because because of the anger. It's it's an apartheid state, right? Hong Kong is ruled by a small number of British folks. And so he identifies with the massive folks who are experiencing life as the colonized, as opposed to the colonizers.

And so I think that that is something that. that's latent within him. And when he comes to the U.S., he ends up having to come back to the U.S. because he gets into too many fights, and his parents are like, you're out of here. Like, you're going to get yourself killed.

So we're putting you back on a slow boat to San Francisco, and you're going to have to figure out how to make it on your own. And don't come back until your success, you know? How old is when you got put on the boat? 18. Oh, wow. He didn't even have, like, his high school diploma. He had to earn his GED in the U.S.

and then he's living in segregated communities. So he's meeting poor white folks. He's meeting all the folks of color who live in Seattle. He's living with them, right? The Chinese, Japanese, the black folks, the Latinos, and Native American folks. And so he's working as a restaurant worker. He was a movie star in Hong Kong, and now he's working as a restaurant worker. And so his whole sort of identity begins to shift from being sort of a

a privileged kid running around Hong Kong, getting into fights, and also doing cha-cha. He was a great dancer and he was like, cha-cha champion. He might have been. I mean, his girlfriends that I talked to were like, wow, like, you could just do a move. And like, by the end of the song,

he'd be like not just doing it, but like adding all kinds of flourishes to it. He was just physically gifted. So many parallels between martial arts and dancing, like in moving with something else. Absolutely. A partner or an opponent, right? Yeah, and you learn it as a choreography, right?

That's the pedagogy of it. And then out of that, you add your own style to it, right? That's, yeah. Physically, it was, he was all that. When he's on the boat coming back over when he's 18, Jamie, he was, so he spent every night on the deck of the boat teaching the rich white people, the Chacha, like Chachar was his dance, it seems. So he was doing a lot of that.

So he would do the teaching. They'd all fall in love with him because he was just incredibly handsome and doing this incredible, this incredible moves and this incredible dancing. And then he would, after the dancing lessons, do Kung Fu experts on the deck of the boat. And they'd be confused. Then they'd be like, what's that? I don't know what that is. There's pictures.

There's actually pictures in the archive that I was lucky to be able to see where he's, he's on the dance floor and he's in the middle of a kung fu form. and everybody else is kind of like looking away and sipping their tea. They're just like not interested at all. Little did they know, right? Like five, ten years later, he would be popularizing that for everybody around the world. I'm just going to say this is a very cool headspace to be in. I'm thoroughly enjoying this.

Yeah. Me too. Thank you, guys. Talk to us about his movies. Because I think we have to. So in preparation of this, I watched Big Boss. Okay. It's a Fury and I'll enter the dragon.

three very different movies that capture Bruce Lee in three very different roles and where in Big Boss he begins a film he's very shy he's timid he won't want to he doesn't want to fight he can't fight and it's only when he's pendant is pulled off and he has to get involved that he finally does it and then professor fewer is very violent from the outset and I guess that's much more political because it recounts how he felt possibly himself. And then you have End of the Dragon, which compared to those two movies,

you can feel the Americanization of the movie. You can feel the blockbuster feel. And when you watch End of the Dragon, you can understand how much influenced American movies for the next

well, until today. Until today for sure. Yeah. I mean, the through... How those movies received in his time? well the through line through them all is is that he's playing sort of an anti-hero right who is somebody who is called to fight to defend the pride and dignity of people who are being oppressed right so in the big boss he's he's on the side of the workers and actually the tragedy of the movie is that he's recruited by the bosses right they they they ply him with drinks and women and all that kind of stuff and he he has a drunken night and and and because of that loses the trust of his community and then that community gets rowded they get killed they get brutally killed and he has to go he he out of guilt feels like he needs to go and revenge avenge their deaths and you know kill the

big boss right and then fist of fury is like as you said it's a very anti-imperial movie it's a movie that's sort of documenting the point where the Japanese had occupied China in the early 1900s in the early part of the 20th century and and and sort of avenging his his first of all, his Kung Fu Kuhn, his, you know, sort of Kung Fu school, but also, you know, on the part of all of the folks who are colonized. And then an enter to Dragon, he's literally part of a three the hard way type group, right, including Jim Kelly's character, Williams, Black Man, and

Roper, the white man, who are there sent to free the slaves, free these drugged prostitutes and slaves from this underground evil layer of this evil sort of James Bond type of villain. So that's

what they were looking for at this particular moment. This is a moment which all of like Asia, Southeast Asia is in upheaval. There's, there are folks who are throwing off their colonial shackles. There are folks who are in labor protests, right? There are there are folks between fights between the communist students and the right wing fascist students in the streets all throughout Asia. And so it's a period of conflict and

upheaval and a period of uprisings. And so Bruce in some ways on the screen, he's enacting and acting out, right? Really what the moment is at that particular point. So we see, I think, in that particular, in that era, like Bruce Rising as an example of this new kind of anti-hero that is defending the poor, you know, as opposed to, say, in the American Western, right? And he's doing with his fists and his legs for the most part, and some sticks and maybe some, you know, little weapons and that kind of thing, but not with guns. And so that's what

makes these movies, I think, so different when they come to the, to the, to the, to the, to the, to the, to the U.S. and to Europe in, in many ways, because the Western is, is power comes out of, rarely comes out of your fist. It comes out of the barrel of a gun. And oftentimes that power is, is restorative power. It's restoring the authority or the order, right, that was supposed to exist there at that particular moment. Whereas Bruce is sort of on the side of these chaotic forces, you know, that are bubbling from the ground up. And yeah, so I think that's, that's, he's also, he's also in that way like a precursor to the anti-hero era that we've been in here in the movies in the West since the 1970s. What's your favorite? My favorite.

It's hard. It goes back and forth. I mean, my favorite, I think, is Fist's the Fear. They're all not Curacao movies. So, like, we should. They're not Ozu. This is not, like, high art. These are B movies.

So we can qualify it that way. But having said that, I think, you know, the fight scene in Where the Dragon is my favorite. And I think the plot of Fist of Feast of Feast of Feud. without all of the weird, romantic, awkward, weird scenes is my favorite. There are these themes that come up, Jeff, on the show quite a bit. And one of the thinking on paper main themes is this, you know, emergent, force, hierarchy, ebb and flow, right?

Especially you're talking about themes like imperialism, colonialism, you know, you have this like order being pushed down from the top and you had this like wait we don't like that new order from the bottom and just with technology with all the things we explore that is definitely a push pull that we see quite a bit yeah yeah and emergent force you're saying in a lot in a lot of ways and i and i think that i share that with the two of you and that that's those are the stories that i I find myself always coming back to thinking about, you know, what it means for folks to be able to develop the power, the force to be able to launch movements against oligarchs, against, you know, against authoritarian, against, you know, folks who are unjustly, you know, treating masses of people. Yeah, it's definitely a theme I keep on coming back around to.

I'd like to go back a little bit to this. It's an interesting mixture of his intrinsic motivations, I think, one being that, this bootstrap thing, this, hey, I've got to go do it, get after it, put the force in, struggle, persevere, that whole thing, with the philosophies that he's become, become famous for, making simple for people, which is a lot of like, forgive the basics of this, but like moving with things as opposed to struggling against things, some of the stoic themes that are now popular, you know, moving with things. Those are two very different things to wrestle with as,

as the main motivators. Did you run across any interesting little thoughts as you saw those kind of rub together throughout your research? Yeah, you know, the central contradiction is Bruce is is receiving these ideas from his teachers and his father and other people in his community that are, you know, about, I'm trying to find the right word for this. They're about how to move in and through things with the least amount of friction, right? right? That's the bewater piece, right? And, and of course, fighting is fighting. Fighting is, it's not dancing, right? He was very clear about the difference between fighting and dancing. You know, this is two people coming to blows. And, you know, his thought was that the purest fight is one in which somebody's going to be dead at the end of it, which one of the people is supposed

we did. That's why he didn't like contests. He thought they were simulacra. He thought they were fake. He thought they were just copies of what the real struggle was about. And so you trained to always be ready. And that's like something chemically, right, that's much different from finding like your flow and your piece, right? And so I found it so interesting how he read Asian philosophy over and over again and interpreted it to try to physicalize it. And it's not like this isn't a trend going back thousands of years, right? Like, you know, Miyamoto and Musashi, like all these fighters had also written books that were about Asian philosophy and drew on Zen Buddhists and Taoist ideas and that kind of thing.

So that was a really interesting contradiction that I kind of discovered and wrestled with. And there's no real solution to it, right? Like it's just sort of the yin and yang of it all. It's the sort of Tai Chi of it all. It's all mixed together and it's all flowing into each other. These are contradictions. These are paradoxes in Western philosophy. And in Eastern philosophies, this is life.

This is, these are the forces that are moving in one, direction sometimes and then they're moving back, pushed by the other force at other times. I coach lacrosse and high schools and stuff. We always talk about read and react. Right. So you have a situation and, you know, even though you have a plan in your head, you may have scripted this version of the thing you're doing, the situation doesn't present itself to where that will be successful, right?

So maybe it's this reading of things and then where it adds to the other side of like, persevere, get after it. Maybe that's the action. No, absolutely. There's always, what it was the saying, there's always a plan until you get hit in the face. Right? The famous boxing saying.

And yeah, and I think that that's, I think that that's exactly how he saw a lot of things, you know. These are tools to be able to kind of move through life. And the other thing is to say that B-Water is just the first part of this longer passage that gives the book, its title, Water Mirror, echo. So the first part is moving be like water, right? So that feels really adaptable to sports, to athletics, to contests, to conflict. Be elusive, move around, like take the path of

least resistance, the fastest point, right? Like move in the way that water does, move with, you know, move down the hill. Like, don't try to go up the hill. And it just feels very, and that's why I think so many folks in corporate jobs and athletics have adopted it but the other two parts are really interesting right it's still be like a mirror moving be like water still be like a mirror

respond like an echo and these last two parts he never really got to explore because he died so early and so it would have been really interesting to see if he ever would have moved beyond a martial phase into you know something that was

you know, it's still be like a mirror, reflecting. Who do you reflect now? What do you reflect? And I think that that's where he was getting to at the end of his life, where he's like, I have to reflect the best of Asian Americans in their fight and philosophy on the screen. He recognized that he was a mirror to many, many people. And then they respond like an echo.

It's like so beautiful. It's like the art of conversation, right? the art of exchange between people. How do you mirror them? How do you echo what they're saying and how do you then take that conversation up to the next level? And so that was what gave me the title for the book because he wrestled through that through his whole life.

And I think I still wrestle with that idea, those ideas every single day in my life too now. So we promised that we would, ask you about everybody's favorite subject, artificial intelligence. Okay. And we want to speak to you about this through the lens of your writing and your musical background. But I think we'll start on the writing. Do you use AI at all to write?

I do. I don't use it to write. I use it to research often. or is it to open up sort of new paths or new directions of discovery for me. You know, it's obviously this knowledge has been known by other people. It's out there. I just might not have been able to get to it without AI. So, so I do.

What I've found is, is AI is a very poor writer because it doesn't have the quirks of, of the human mind. And so I've done things like loaded up, you know, chat or Claude with my old writings and said, hey, you know, write something in my, in Jeff Chang's voice about, I don't know, you know, like, you know, why you shouldn't eat parrots or something. I don't know, you know, just like weird topics, right? And it'll spit out something that can mimic very well my paragraph structures. and even the ways that I like to construct sentences sometimes, but the stuff is garbage.

You know what I mean? I know that nine times out of ten, were I to write an essay on why you shouldn't eat parrots, it's going to come out better than AI. And so I just gave up on that a long time ago. I'd rather go through the work of developing the drafts, and it's always the fourth draft where I begin to actually hit my velocity. It's always the, I don't know why.

It's always the fourth, but it's always the fourth draft in which I'm like, oh, this is, now we're moving. At the fourth, at the fourth, it hits the inflection point. But I know that I'm going to have to struggle through the first three. And that struggle is, it's the worst thing in the world and it's the best thing. in the world for me. So I don't want to give up the best thing about it, but I know that I'm going to have to go through the worst thing about it. Just like training, right? Just like, like, you know, Bruce used to do whatever, a thousand sit-ups a day. But he was doing that so he could

get on screen and do his thing, I guess. And so the three drafts are the thousand sit-ups, I guess. On this four-draft thing, do you ever get to the tail end of the third and you start the fourth? Do you get anxiety that the fourth might not be the one? Do you usually, start going, oh shit, what if it's not the fourth? Sometimes it's not. Sometimes it's like, you know, the fifth or the sixth, but usually it's the, I don't know why, but honestly, like, I look back at all the drafts that I've written, like, for decades, and it's

always the fourth. It's, there's just something about, like, the iterations, you know, in which the first one, the first draft is usually, like, random thoughts thrown onto, like, vomited onto a paper. Or, or random thoughts plus a few good sentences vomited onto a paper and there's no connecting them. And then through the first, second, and third draft, it's, that's the process. The process is the iteration of, of going through eliminating, adding, going, oh, that's, I didn't want to talk about that at all. I wanted to talk

about this. And then, and then the digressions, the other digressions that might come in that actually begin to form and fit into that. And that's where I think AI will never have judgment on on those kinds of things, right? Like on what is, what creates the original thought is this, is this process of, of elimination. And that's where AI is needing the prompt to come back in and say, no, let's go back in this direction. Let's go back in that direction.

But, but it's, it's still the, the user, the human user is still, I think, at a primitive state of where that idea is developing. Like, I'm going through a million prompts in my head to get from draft one to draft one and a half, right, to draft 1.75, then to draft 2. I'm going, like, that would require, I'm saying, a million prompts on my behalf. If you were directing yourself as the engine, right? Right, right. You're making a million split-second decisions as you're reading through these sentences and you're reading through these ideas and you're thinking about what's not there as well. And so that's partly why I'm bullish about AI never overtaking art, human art in that way.

But it's a good tool. What I wanted to say was, is we did a, I do a podcast called Notes from the Edge for KLWI here in San Francisco. And we had brought in, this is last year, Karen Howe, right, who talked about imperialism, did Empire of AI. And Ramon. Yeah. We did a, we did a whole book club series on that book, chapter by chapter. Yeah, it was amazing. Isn't it one of the, I think it's one of the best books really of this century so far.

Without, without qualification. And I've told her that. And Ramon Chaudry, who was there from the very beginning as an ethicist, as an AI ethicist, and has been working through. So we went through this. We had this great conversation about AI, which now actually sounds, we did. just did this maybe a few several months ago and it sounds so dated now. But the other thing that we did that I did was I wanted to talk to a good friend who's very close to technology about how he

approaches it. So I invited my old friend DJ Shadow, you know, soul sides, shout out soul sides in house. Right. Yeah, he's there on doing the 30th anniversary now. But I wanted to talk to Josh to shadow about how he thinks about technology, you know, because, and I was surprised because he was like, oh, I've toyed around with AI. He doesn't use it because he doesn't think that he was surprised with some of the results that they were able to get with some of the pros, but he doesn't use it because he thinks it's corny. He just thinks it's corny. And the other part of it was, you know, he's agnostic, I think, about technology in, in, in, in, in, in, in, in, in, in, in, new ways. And so I wanted to talk to him about, like, what are, what are the ways that you

would use it and what the ways that you wouldn't use it? How do you develop, how do we develop a relationship to technology? Was really the question I was trying to ask him. And he said something that was really deep and super interesting to me, which is like, hey, you know, these are all tools for us, right? The thing to remember, he said was if you're, if you're listening to somebody who's, like, really high in the technology, it's probably because they're making money off of it. And if you're hearing somebody who's like really, really down on the technology, well, you know, like they might have some, like, there's probably truth in both sides, but the people who are against it and stuff like that, there's probably a little bit more truth to what they're saying around it and how it's going to impact people. But he compared it to sampling, the advent of sampling technology. And I remember him when he first got started, he had a belt drive turntable in a four-track task cam recorder.

And out of that, he made some of the most amazing music one would ever imagine. You know, a lot of that stuff he's kind of put out on little CDs and recordings and that kind of thing. By the time he got to introducing, he did introduce it on his first sampler and Akai, right? And by the time he got to the Akai, he could freak that Akai in ways that nobody else would have been able to think about because he had been working with such low-tech, low-fi technology. And he was able to hear things that, you know, that whoever, that P. Diddy wouldn't hear, would never hear in a million years, right? because he had literally spent his 10,000 hours on that cassette, four track and that belt drive turntable, like looping things one measure at a time to build like four or five minute songs, 10 minute songs sometimes.

It's kind of like that Beastie Boy story where they run the tape all the way around the table through the delay and the drums and all of a sudden it's like, whoa, that's the sound. And it's like you start thinking about that. And it's like creativity is is the unique arrangement of things you find, right? Those elements can be different. You know, now technology can influence the elements. They can make new elements. They can push the boundaries on stuff.

Like when he was with the Akai, knowing where to go beyond with that, I think. Are we looking at this in the same way? Well, so in that sense, you know, I think that that was liberating for me, you know, to hear, oh, yeah, I've tried it and maybe one day I'll use it. But for the most part, why? Why should I do that? It does, I'm not, the whole point, he says, is like, it's about getting the sound that you need, right? For the part of the song that you need it for.

And that, for that sound to fit in with everything else. And, you know, at least right now in terms of the way that folks are musically using AI, it strikes me that they're getting, you know, you're using these sort of catch-all phrases and prompts, you're doing sort of a, and this I think mimics the thought processes. You want to get into the philosophy of it, right, of the designers of large language models is it's a mountaintop sort of, you know, godly type of view. This is actually, that's a very Western thinking, right? Very Western philosophy, this mountain top type of view, like looking down on how to use

the technology, as opposed to somebody like Josh who was building these beats, like I said measure by measure. And so he's thinking about it in terms of units of sound and how that builds up to things. And he's like, usually I can find much more surprising sounds rating my record collection. Rating my record collection. Analog records. You know, yeah, it's unpredictable. It's weird. It's quirky. It's eccentric. And ultimately, it's what he believes. He believes. will set his aesthetic off from everybody else, including the, including, you know, the person who's sitting there with Suno

and just typing in things. I can't believe your best friend is DJ Shadow. I literally spent two years in the 90s with that record on constant, constant loop. Absolute joy whenever, even the album cover, that green, the record shop, just, ah, genius, genius. That was the shop that we used to go to, Sacramento, yeah.

There you go. A quote from Bruce Lee on technology, perhaps. Tools, goals and equipment are merely means to an end. The ultimate goal is the expression of the individual, not the mastery of tool. So all that said, many people aren't creative. So it does give people a way to be creative. But are they genuinely being creative if they use AI in that? ideation phase?

That's, I mean, you know, that takes us maybe to the question of creativity and how to define it. And I, you know, I sort of take a populist view of creativity. Like everybody can be creative and, and in that way that intersects, I think, with the idea that AI can be a tool to use. Maybe there'll be one day in the way, in the same way that Josh made this album that was all sample based and blew a lot of people's minds. about it, you know, which he wasn't the first to do it. There are other people that, I mean, like you're talking about the Beastie Boys, they learned from the bomb squad, right, from Public Enemy, who were the first ones who had done the loop of the tape around the thing

to make songs like Rebel Without a Pause. But, you know, I think there's, like, the level of creativity, the, I'll put it like this, the level of creativity that is meant to be able to make something that persists and endures, that, well, that first surprises and delights and moves many, many people, and then indoors because of that, right? I would say that the odds are against AI at this point being used in that kind of way, although somebody might come along and do it in a different kind of way. There might be another 18-year-old prodigy, you know, who in two or three years might make something like, you know, an avalanches type of record or a DJ Shadow type of record with AI sounds using AI methods.

And people will be like, oh, how did that person do that? But it's still the human being at the core of that orchestrating it. Yeah. which needs perfectly to the follow-over question, Jeff. I don't know if you're aware of this, but every show on thinging on paper, we ask the guest to leave a question for the next guess. And then you answer the question from the last guest

and you pose a question for the next guest. And last week's guest was Harry Kumar, the CEO of a quantum computing entertainment company. So they're using quantum computers to make music and game. And his question for you, was, quote, do you believe you could enjoy a piece of media, music, art, or film

that was generated solely by an autonomous system, what he describes as autoculture, so we're coining that, yeah. Autoculture. Completely autoculture, coined here, solely by an autonomous system. Do you believe you could enjoy it? That I could enjoy it?

Hmm. Yeah. I'm going to have to head. my bets and just say maybe, maybe. Would it matter if you knew it was made by a completely autonomous system? It would. Yeah. It would.

It would. It would. I think, I think though that I would, if it were to move me, I would be curious as curious about myself as to why it had moved me. I'm very much in the school of thought aligned with the with the folks who are, um, are, are,

are, are, are, are, are leaning against, you know, the use of AI. But, you know, you're,

I'm, I'm also aware that delight can happen in all kinds of ways. Right. It's just human. And, and, and I would be curious about, like,

what, what created that delight for me. And, and then to, and curious about how, that delight was engineered. Let's put it that way, I suppose, right? To be very

specific about it. So I'd be open. I think it's a, that's an easier question to ask than to ask the question whether or not, to ask questions about the relative aesthetics of, of, of, of, of, of, of, of, of, of the work, you know, over time. and the implications of those aesthetics and stuff. I think it's a little bit of a different question.

I've been delighted by a lot of stuff that I've been surprised that I've been delighted about, and it's led me into that sort of thinking process for sure. Jeremy, for you? You always have an opinion that you love speaking about this. Yeah, it's tough. I love the open-mindedness that you bring to that, Jeff, and I think we all have to because we don't know

what is going to be the next example of what Shadow did with his record, what Dilla did with his stuff, to squash it completely. But also I think there's something that I appreciate about someone who's gone through the four drafts. You know, someone who has wrestled with the idea enough who had the thoughtfulness and intentionality

and got after the reps to land on a final point that I would take away and be like, damn. So I think if I knew, If I knew it was full auto, I would probably have a little bit of a, I'd bring some, bring some energy to that. Yeah. I don't know. Yeah, I definitely hear that. I definitely hear that.

Yeah. Yeah, and that's where my solidarity's with lies. All the other folks who are struggling to create something new, novel, delightful for, for folks. Yeah, I think it's important to just have the stamp on it. it that it is this or it isn't this, right? You know, to let us make the, put that in the right bucket for our navigation, I guess. Yeah. But the other part of it, though, is this like, this melding, right?

Like, where does the, where does the human end and the technology begin? Or maybe the other way around, right? Where's the technology end and where does the human begin? Kevin Kelly says it doesn't. They are part of the same kingdom. Yeah, yeah. That's why he said on thinking on paper. Much to think on.

Much to think of, yeah. Would you have a question? So it can be in that vein. It can be about anything else. There are no rules about the question that you leave for the next guest. I will not tell you who the next guest is where they work. It can be about anything. Oh, this is such a great.

I love this. And that was a pretty profound question. I guess maybe one of the questions I'm constantly having is, if not for humans, then what is technology for? or who is technology for? I think about that now as we're kind of entering this particular point. I won't be alive to see if there's the change that all of these folks say is going to come with the advent of the so-called advent of superintelligence.

I won't be alive. But it feels, yeah, it feels like an existential type of question that many people need to struggle with. That's a big one. could spend some time with that. Yeah, I want to hear you guys on the next episode. Yeah. Yeah, for sure. Jeff, this was fun, man. Thank you so much for your work. Thank you so much for your four drafts and your wrestling of awesome ideas that are that are being brought to light. It's great and enjoy talking with you. Really enjoyed talking with you too as well. Thanks for the invitation.

Thank you very much. Do you have a a closing Bruce Lee quote anecdote little tip bit that you could leave for the disruptors and curious minds of thinking on paper there's so many in that book it's got 600 pages um what would be a good one for us to to to kind of talk through to think to to sleep on to sleep on geez there's so many what would be good one what would be a good one were there any that struck you? And this is like, I didn't know that. And that changes everything for me. In terms of quotes, no, but we speak a lot on thinking on paper about serendipity and sliding doors and moments that make us or break us.

And reading about his, the first, well, all of his life, really. He just seemed to slip through those doors in such an incredible way. So many opportunities, so many moments where a different path was open and he could have chosen or forced to take. And just that path, those steps that he took. And it just makes me think about life and opportunity in the decisions we make lead us to where we are. we are just a collection of our choices and he just, yeah. I don't say, yeah, but being just an incredible, incredible life. Yeah.

I think I was struck in reading his papers and speaking to his friends and family by actually how vulnerable he was in many of these moments, right? So we're talking earlier about the chief great aim quote, right? And that that came out of a period where he was getting no jobs in Hollywood. And so to be able to kind of align the papers I was seeing in the archive with, like, the events that were happening in his life, because a lot of these types of things have been written about, the narrative about Bruce is that he was always destined to be this guy. And I think in writing the book, I was just always struck by the fact that he, he, he had to make it.

He had to forge his way. And so you're pointing out his persistence and his sort of, some folks would frame it as sort of his one single-mindedness, you know? And I think the biggest kick I got out of thinking about that was hearing the stories from his friends at the university. He went to the University of Washington for a few years.

And he would hang out with folks. And even then he would go up to folks and he'd be like, hey man, punch me. And they'd be like, no, no, but just punch me. Just try to punch me. And of course, they'd be like, what are you talking about? We're just like, we're just eating lunch here. What's like, just chill out, man. And you'd be like, no, punch me, punch me.

And so people would, you know, half heartily or sometimes hardly, hardly. they would they would half-heartedly or heartedly throw a punch and he would just like grab them and twist him up in in a in some sort of a lock and they'd like Bruce dude chill out like what's going on here and they'd be like oh man like just we don't want to hang out that guy he's so single-minded he only thinks about this stuff and he doesn't think about anything else you know and to think about Bruce as that person who was actually, like, not naturally, he, he was very, very showman-like and presented as an extrovert in some ways, but he was very, like, in some ways, very not confident in himself, right? So he didn't have a lot of social graces. He sort of had, he had a way of being about him that presented as, as, like, single-minded.

But that was how he engaged people. And what's so interesting is that that particular thing, right, which socially like maybe might be looked down upon and that kind of thing, was maybe a lot of what it took for him to not hear no, right? To like ignore the noes and to just keep on pushing and pushing and pushing to get to the point where folks would finally be able to say yes. And I think that that was just a good reminder for those of us who are always trying to please other people

all the time or work to kind of support other people or that kind of thing. Hey man, you know, like sometimes you just got to be about it. Yeah. Water, mirror, echo. Bruce Lee, in the making of Asian America, Jeff Chang. Thank you. you for thinking on paper with us

today. Thank you guys, boys. I so appreciate it. Thank you. Yes, Mark doesn't believe in destiny. You make your own fate. See next time. Be disruptive. Stay curious.

Keep thinking on paper.