616. How to Make Something from Nothing | Freakonomics Radio

Adam Moss was the best magazine editor of his generation. When he retired, he took up painting. But he wasn’t very good, and that made him sad. So he wrote a book about how creative people work— and, in the process, he made himself happy again. You can find the transcript and show notes for this episode on our website here: https://freakonomics.com/podcast/how-to-make-something-from-nothing/ FOLLOW FREAKONOMICS RADIO: YouTube: https://freak.ws/3yIl6dl Apple Podcasts: https://freak.ws/3yAvQh0 Spotify: https://freak.ws/3TsdCmV ABOUT FREAKONOMICS RADIO: Discover the hidden side of everything with host Stephen J. Dubner, co-author of the Freakonomics books. Each week, Dubner speaks with Nobel laureates and provocateurs, intellectuals and entrepreneurs, and various other underachievers to uncover things you always thought you knew (but didn’t) and things you never thought you wanted to know (but do) — from the economics of sleep to the future of education, from markets for marriage to the surprising utility of wolves. ABOUT THE FREAKONOMICS RADIO NETWORK: Freakonomics began as a book, which led to a blog, a documentary film, more books, a pair of pants, and in 2010, a podcast called Freakonomics Radio. Hosted by Stephen J. Dubner, it’s one of the most popular podcasts in the world, with a reputation for storytelling that is both rigorous and entertaining. Its archive of more than 500 episodes is available, for free, on any podcast app, and the show airs weekly on NPR stations. Freakonomics Radio is now the flagship show of the Freakonomics Radio Network, which includes the podcasts No Stupid Questions, People I (Mostly) Admire, and The Economics of Everyday Things. FREAKONOMICS RADIO NETWORK PODCASTS: Freakonomics Radio: https://freakonomics.com/series/freakonomics-radio/ No Stupid Questions: https://freakonomics.com/series/nsq/ People I (Mostly) Admire: https://freakonomics.com/series/people-i-mostly-admire/ The Economics of Everyday Things: https://freakonomics.com/series/everyday-things/ Special series: https://freakonomics.com/topics/ CONNECT WITH US: [email protected] https://twitter.com/freakonomics https://www.instagram.com/freakonomics/ https://www.facebook.com/freakonomics/ https://www.tiktok.com/@freakonomicsradio https://www.linkedin.com/company/freakonomics-media Subscribe to our newsletter: http://eepurl.com/bKm0cf

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:04Stephen J. Dubner?

  Hey there. It's Stephen Dubner, and I would like to remind you about two live shows that we are putting on soon. The first one is on January 3rd in San Francisco. The second is in Los Angeles on February 13th. We have got some excellent guests for both shows, so please come hang out with us. Tickets are at Freakonomics.com/liveshows, one word. Again, January 3rd and February 13th, San Francisco and LA. Meanwhile, today on the show, a conversation with someone I know quite well, or at least used to, someone who is smart, shrewd, very good at his work, and someone who taught me a lot, even if not always on purpose. Why don't you just say your name and what you do?

• 0:49Speaker 01

  My name is Adam Moss. That's easy enough. I am an editor by lifelong profession, and recently an author, and sometimes a painter.

• 1:00Stephen J. Dubner?

  For a long time, Adam Moss was widely considered the best magazine editor around. He was the founding editor of Seven Days Magazine, a clever and slightly transgressive arts and culture weekly. From there, he went to the New York Times Magazine, and after many years there, he took over New York Magazine, which he radically remade for the digital era. He won all the awards an editor can win. He directly shaped the careers of hundreds of writers and editors. Indirectly, he did the same for millions of readers. He left New York Magazine in 2019, still on top, but feeling a bit too old for the game, a bit burned out, and ready for something new. The something new eventually took the form

• 1:45Stephen J. Dubner?

  of a book called The Work of Art: How Something Comes From Nothing.

• 1:51Speaker 01

  The book is 43 cases of building something from first notion to finished product with all that kind of torture in between.

• 2:00Stephen J. Dubner?

  Many people who know Adam Moss were surprised that he wrote a book. He was one of the few magazine editors who didn't either start out as a writer, or want to be a writer, or think of themselves as a writer. He was a full-fledged editor. An editor is mostly backstage. There is a lot of power and a bit of risk. A writer, meanwhile, is out front, directly in the line of fire. You work on a thing for months or years, and then it goes out into the world with your name on it. So if people hate it, they know where to find you. That's why it was so intriguing that Adam Moss would write a book. So we will talk about that today, but some other things, too. Especially his tenure at the New York Times Magazine, where he happened to be my boss.

• 2:45Stephen J. Dubner?

  This was in the late 1990s. I was what's called a story editor, which meant I came up with ideas, assigned them to writers, and then shepherded those pieces through the editorial and publishing processes. The Times Magazine was considered a great magazine during this era, and it was a thrill to be inside of that. Also terrifying sometimes, but mostly a thrill, and mostly because our boss was really good at his job, and we all got to watch and learn. That said, I quit the Times after about five years. It used to be that when someone left that place voluntarily and was relatively young, I was in my 30s, that people would think you're crazy. I was doing well as an editor and an occasional writer.

• 3:30Stephen J. Dubner?

  The bosses told me I might be a boss before long. That was the last straw. I didn't want to be an editor or a boss. I just wanted to be a writer, and I wanted to work on my own, not within a hierarchy. So I quit, and I went off to write books, which is how I ended up here, talking to you. When Adam Moss's book came out in early 2024, I read it right away. For me and many others who worked for him, it was a bit like discovering his journal. Everything that made him tick as an editor, as a boss, was right there on the page. At the time, I was trying to make a podcast series about mentorship. The idea was that mentorship is this standard and successful practice in many realms, in

• 4:15Stephen J. Dubner?

  education, in sports, the military, in the medical and legal professions, and yet, in other realms, there's no standard mentorship at all. I wanted to know why not, and whether something should be done about that. But the mentorship series just never came together. We couldn't find a center of gravity and eventually we gave up, which is fine. That happens all the time in this kind of work. But there was one interview we did for the series that I was not willing to ditch. This one, the one with Adam Moss. Was he in fact, a mentor to me? Or maybe more like the master who teaches an apprentice? Or was he just an old fashioned boss trying to extract labor? That's what today's conversation is about.

• 5:00Stephen J. Dubner?

  It's the latest in our series of one-on-one conversations to end the year. Even if you are not a big fan of magazines, even if you have never held a paper magazine in your hands, I suspect that you will benefit from hearing Adam Moss's perspective because all of us at some point try to make something from nothing. So you might as well learn from a good teacher like I did.

• 5:36Speaker 02

  This is Freakonomics Radio, the podcast that explores the hidden side of everything with your host, Stephen Dubner.

• 5:52Stephen J. Dubner?

  The title of Adam Moss's book, The Work of Art, is of course, a double entendre. He is the kind of person for whom entendres rarely come singly. There is a layer and then another layer and usually a few more. This book is ostensibly a set of interviews with a variety of makers. Stephen Sondheim, Twyla Tharp, David Simon, Samin Nosrat, Will Shortz. And their stories unfold on pages that are packed with sketches and graphics, sidebars, footnotes. It is very much a magazine in book form, which makes sense considering that Adam spent nearly 40 years making magazines and this is his first book.

• 6:35Stephen J. Dubner?

  Some people end up in magazines by accident, like me. I just wanted to write and that's where the writing jobs were. Adam was different. He was in love with the magazine form. So I asked what first drew him in.

• 6:50Speaker 01

  So many things. First of all, when I came to love magazines, it was the late 60s, early 70s. It was the heyday of the magazine form, but also it was a really interesting time. The world was blowing up in some ways that to a young kid were just very attractive. And the magazines that I loved, like the New Yorks and Esquire's, etc., they were little, smart ass. They were funny. I mean, my first magazine I read was Mad Magazine. So it had this kind of fabulous fractured idea of what the world was that really appealed to my adolescent brain. And there was the feeling that the whole thing was created by someone or something that felt very distinct. It had a personality. And that personality,

• 7:34Speaker 01

  if it appealed to you, it was very powerful. It felt very personal. So this was the medium that you loved, and then you sought it out? Yes. And then who? Okay, so I had all of this stuff in my head, but it was unformed. And I went to work at Esquire. And I was very young. I was a very unformed person at that point. What were you good at? I was probably fairly intuitive. I certainly was eager. And I'd read a lot of magazines. I had a lot of data in my head, based on my own fan taste. And this guy named Lee Eisenberg, he just, for whatever reason, took an interest in me. It could have been that he just wanted me to do his work for him, because he recognized that my enthusiasm

• 8:18Speaker 01

  was potentially valuable to him. But he also saw that my brain worked a certain way, and he wanted to encourage it. It was an act of kindness. Name some things that you would do there on a given day? We started a section on the entertainment industry. And one of Lee's ideas was that he would put a movie star with a big literary person. I remember William Styron and Candace Bergen. My job was to...

• 8:45Speaker 01

  Go to the thing and set up the tape recorder and then make sure everybody was happy. But then he would give me the transcript and he would say, what do you find interesting in this? Slowly but surely, I would see what he thought was interesting in it. And then I would watch him as he constructed this thing into an exciting little bit of conversation that worked in a printed form. He was extremely good. So just being able to watch him took all of that data in my head and started to organize it. That was invaluable. One of the things that I hear a lot from younger editors is that they really resent doing the older editor's job for them because they feel it's exploitive, and it is. However,

• 9:29Speaker 01

  it's an incredible way to learn.

• 9:31Stephen J. Dubner?

  I mean, it's apprenticeship.

• 9:32Speaker 01

  Yes. And you talk it through and in there is a sharing of ideas, but also a kind of teaching. And sometimes the teaching goes both ways. This is really, I think, actually crucial. In almost every case where there is a mentor or mentee kind of thing, it goes both ways.

• 9:49Stephen J. Dubner?

  Give an example of you as a young editor, as a mentee, let's call it. What do you think Lee Eisenberg got from you?

• 9:57Speaker 01

  There was a generational difference, not a huge one, but I brought a bunch of generational assumptions to the table that he didn't have. I think there is that element of-

• 10:07Stephen J. Dubner?

  New eyes, fresh eyes?

• 10:08Speaker 01

  Yeah, fresh eyes. And as you get older, you begin to dismiss certain things that aren't fully dismissible.

• 10:13Stephen J. Dubner?

  So you were the editor of a few different magazines for a long time. Can you explain the role, just briefly, of what it means to be the editor in chief of a magazine? I think a lot of people who aren't writers or editors-

• 10:25Speaker 01

  Don't really understand that.

• 10:26Stephen J. Dubner?

  Yeah.

• 10:26Speaker 01

  It's chiefly the person who decides where the magazine's going to go, what the magazine covers and doesn't, shaping the magazine's identity and its relationship to its readers. It's a manager job. The magazine is very, very much a group enterprise. That's one of the most wonderful things about it. And it involves getting a whole bunch of people, story editors, like you were, visual people, copy editors, production people, all sorts of different kinds of people to work together as one. So in that sense, it's like a conductor of an orchestra. It's very rarely what people think of as editors, which is the person who fixes sentences.

• 11:05Stephen J. Dubner?

  Although you did your share of that.

• 11:06Speaker 01

  I did my share of that, but that's not the chief job description. The chief job description is the overall direction of the thing.

• 11:13Stephen J. Dubner?

  So you, as a magazine editor, are renowned. In the field of magazine making, Adam Moss is considered a great editor, and I certainly agree. And one of the many things that I and a lot of people think you did well was that you were very, the word that people like to use is exacting.

• 11:30Speaker 01

  [laughing]

• 11:32Stephen J. Dubner?

  There's a standard that is extremely high, but also a little bit elusive and ethereal. You don't quite know what it is, but you know you want to get there. Let's say you agree that you're exacting.

• 11:42Speaker 01

  I agree that I'm exacting. I would like to think that I was a little bit more clear about what it was that I was looking for, but I recognize that that's probably completely not true. And what I was doing was a kind of maddening mind control.

• 11:55Stephen J. Dubner?

  It's a spectrum, but let's agree that you're exacting. My question would be, when you are an exacting person, and I'm sure many people listening to this conversation either are or want to be that, but you also can't control every single thing. In fact, the process is set up so that you're not controlled. You're not writing the articles, you're not editing the articles heavily.

• 12:17Speaker 01

  Absolutely.

• 12:17Stephen J. Dubner?

  So how do you live with that paradox?

• 12:20Speaker 01

  Being an editor, it's both an act of grandiosity and humility at the same time. So it's like, you have to think big, but you have to understand that it really is a group project. And for any group project to work, everybody has to feel...

• 12:36Speaker 01

  Like there's some of them in it and they have to feel invested in it and they have to feel proud of it. They have to want to make it just as badly as you want to make it. And so part of the exacting hood was not just getting people to a certain standard that I thought was appropriate, but also getting people to care as much as I did.

• 13:00Stephen J. Dubner?

  How much of that was in the hiring, though?

• 13:02Speaker 01

  A lot of it's in the hiring, but a lot of it's also in the sort of day to day way that you all get together as a group. A lot of it is just familial as opposed to directed towards a particular task. A lot of it is helping people find their own independence as thinkers, but also obviously think the way you want them to for the purposes of this project. Like a parent, I suppose, I would always relish the first moment that a story editor was willing to fight with me because I just felt, okay, they've got it now. They have their strong point of view. Getting people to feel independent within an environment that they weren't entirely independent. It's a kind of weird little

• 13:46Speaker 01

  equilibrium, but that was what I was after.

• 13:49Stephen J. Dubner?

  I was very happy that you landed on the parenting analogy because as you were speaking, that's what it sounded like.

• 13:56Speaker 01

  Sure.

• 13:57Stephen J. Dubner?

  For sure. So, parent-ish, I think, applies. What about mentor? Do you think of yourself as a mentor? Or is that not a word that fits?

• 14:06Speaker 01

  I recognize that there's mentorship going on. It sounds pretentious to call yourself a mentor unless it's like an actual title. One's a little bit squeamish about using language like that. But the act of teaching someone I do recognize is crucial to being, definitely to leading, but also just, you're learning all the time. There's a kind of mentor menteeship that happens in every dimension of life.

• 14:31Stephen J. Dubner?

  How do you choose, though, as a teacher? How do you choose who to spend time with? Because you were supervising a lot of people at a place like The Times Magazine. I don't know how many story editors there were, maybe eight, 10, 12. You had very different relationships with each one. How does that work for you? Is it a choice?

• 14:50Speaker 01

  I don't think it's a choice exactly. You hope that everybody feels that they're the favorite child. That's what you're trying to do. But everybody responds to different kinds of help, prodding.

• 15:02Speaker 01

  Embracing all the various things that make for mentorships. Just back to the family thing, you have a different relationship with each of your children. That's not to say that somewhere in there, you don't have people that you think have more potential. Generally, there are people who show that they're eager to learn. They kind of put their hand up and say, "Teach me." And there's no teacher who isn't moved by that.

• 15:28Stephen J. Dubner?

  Do you have advice for people who are not naturally, you know? I do believe there's an astonishing amount of human capital in the world that is untapped. Because the possessor of it doesn't know how to export it, and others don't know how to import it.

• 15:45Speaker 01

  Import it, yeah, that's nice. I don't have advice except to recognize that it's an essential part of learning, to be open to learning and to teach. Then maybe you have to make a slightly more active effort at it. You certainly have to be open to it. You certainly have to know what you don't know and find ways to ask, maybe not out loud, but to signal your openness to being taught. I mean, it's an interesting period because what I witness in younger people these days is that they love their parents and they have, you know, they're very...

• 16:18Stephen J. Dubner?

  And very different relationships with their parents.

• 16:20Speaker 01

  Yes, very, very different. And also, they're very comfortable with adults in a way that was different from when I was young. But there are certain things they resent. And there's a kind of parenting, as it exists in a workplace, that they would bristle at, which I found very valuable growing up. You know, it's a sort of famous thing at Esquire when I was there. There would be these story meetings and people would cry at the end of the meeting. They would leave and cry because the editors in charge were kind of unstinting in their...

• 16:54Speaker 01

  Withering comments.

• 16:55Stephen J. Dubner?

  Now, you say this as if people didn't leave and cry at the end of a New York Times Magazine meeting when you were...

• 17:01Speaker 01

  Well, I...

• 17:02Stephen J. Dubner?

  You just didn't see it.

• 17:03Speaker 01

  The point is that I learned from my own mentors that this was the way you conducted a meeting. It was much more efficient to be brutally honest. That's an idea that doesn't work because blah, blah, blah, blah. One thought of that as teaching. I tried to bring some of that stricter method and people were gassed. And I would say, "Look, when I was growing up, you used to cry at the end of these meetings." And they said, "I don't want to cry at the end of the meetings and it's not going to work." And they were right. It wasn't necessarily the better way to do it, but because it was the way that I learned how to sharpen my mind as an editor, I had an expectation that I should do the same with those people I was trying to get to do the work a certain way. In that case, yeah, they taught me.

• 17:48Stephen J. Dubner?

  Meaning the younger people taught you, like, "This doesn't feel good."

• 17:50Speaker 01

  This doesn't feel good.

• 17:51Stephen J. Dubner?

  But did you stop?

• 17:51Speaker 01

  And this doesn't... Well, I found workarounds. I found other ways to try to accomplish the same thing.

• 17:57Stephen J. Dubner?

  For instance, just different language?

• 18:00Speaker 01

  Probably I learned to praise and then to withhold.

• 18:04Stephen J. Dubner?

  So that was a strategy?

• 18:04Speaker 01

  Come over... It wasn't a conscious strategy, but I realized that's what I was doing. I was certainly told it enough times that I came to realize that, "Oh, yeah, this is what I do."

• 18:14Stephen J. Dubner?

  I did speak with five, six, seven former employees of yours, some of whom I overlapped with at the Times Magazine, some of whom I didn't. If we were making a word cloud, I think withholding was probably the big word.

• 18:27Speaker 01

  Oh, no.

• 18:29Stephen J. Dubner?

  But let me just say that, on balance, the overall experience was overwhelmingly positive because what I got from working with you and what they all got was just a deep, deep satisfaction of accomplishment and a recognition that you don't get that satisfaction without having a lot of failure and bumps along the way. Not humiliation, and you didn't humiliate people ever, as far as I know. I don't know.

• 18:58Speaker 01

  I don't think so. I hope not.

• 19:01Stephen J. Dubner?

  So when I left the Times Magazine, working for you, I left because I just wanted to be a writer. I loved being an editor. Editing was the best training for me to be a writer, in part because I saw how many big-time writers, when they would turn in their manuscripts, they were terrible. And I thought, holy cow.

• 19:19Speaker 01

  If they can turn in stuff like that, I can do this.

• 19:21Stephen J. Dubner?

  Yes, Pulitzer Prize winners. I was shocked, but it was also just amazing experience and fun. It's really fun to do the work. But then you gave me a six month leave to go start working on my first book. And I remember coming back and saying, this is the life I want. I like alone. And then I remember, at least my recollection is that I said, I'm really appreciative of the leave you gave me and I love this place. I love this work, but that's what I want to do long term. And so I'd like to stay here for another year. That's the deal that I remember crafting. And then I remember our relationship changed because it was, I was a lame duck.

• 19:59Speaker 01

  So what, did I just not care about you anymore? Because you are not going to be a long-term asset for me? Was I that calculated?

• 20:08Stephen J. Dubner?

  I wouldn't say it was that. I think it was more like plow horse idea.

• 20:12Speaker 01

  Get as much out of you as I could.

• 20:14Stephen J. Dubner?

  And it wasn't bad. The work was still really exciting, but another reason I left was that I recognized when you succeed in a place like that, I mean, this happens in many occupations. When you succeed in some kind of maker role, you end up getting promoted into a manager role, a boss, and I did not want to be a boss. So leaving the times to write meant I would never have to be a boss of anyone other than myself. But then I wrote books and then the books turned into this thing that we're doing now.

• 20:44Speaker 01

  You're a boss.

• 20:45Stephen J. Dubner?

  Yeah, we have 20 people. And I think the boss that I became is very much like the boss that you were.

• 20:53Speaker 01

  Oh, really?

• 20:54Stephen J. Dubner?

  Oh, my God.

• 20:54Speaker 01

  Now, is that just natural? Or do you think that you learned certain attributes of a boss person from me?

• 21:01Stephen J. Dubner?

  Not natural, all learned. That's what I'm saying. That's why I would call you a mentor, even if an unintentional or accidental mentor.

• 21:09Speaker 01

  Oh, how interesting. God, that's scary.

• 21:11Stephen J. Dubner?

  I'm a writer. You know, writers are writers. You have a way of seeing the world. You have a way of, and a lot of this is what I learned from you. You have a way of assessing, is this idea worth doing?

• 21:22Speaker 01

  Definitely. That's a big part of it.

• 21:24Stephen J. Dubner?

  Execution is important, but I always think of it a little bit like pro athletes. Like, you wouldn't be here if you didn't have the talent. And then you realize that what you're really after is developing your taste or your sense of what's interesting, what's important, what's fun, what's new.

• 21:42Speaker 01

  Right.

• 21:43Stephen J. Dubner?

  And those are all things I learned from you.

• 21:45Speaker 01

  You may have learned some methods from me, but your taste and sensibility was not something I had much influence over at all, because it's just who you are.

• 21:53Stephen J. Dubner?

  Maybe to some degree, but I think anybody who's learning, who takes their thing seriously, it's thrilling when you encounter someone who sets a standard high. But the problem is, when you go from being a writer to then being a boss, my first producing partner is, the word that got attached to me was like, Dubner's too exacting. And I was pissed because I thought, like, what's wrong with that? I learned from Adam Moss.

• 22:21Speaker 01

  Even hearing it back to me, I don't think that's a bad thing. I think that's something that you should wear proudly. I'm very glad to hear that what you felt as a person working with me, for me, whatever.

• 22:34Stephen J. Dubner?

  You can say for you. It's okay.

• 22:36Speaker 01

  Was that you found delight in making something great. That's the main thing that I was trying to teach. Even though it's painful in the moment, you're going to feel so good at having made something that you put everything into and that you can be proud of at the end. I hope that I conveyed that and that I worked with the kind of people who would feel that and who would be willing to work pretty hard because they wanted to make something they felt really, really good about. That's not everybody, but that is a certain kind of person, and you're that kind of person, and I'm that kind of person. And there's a reason we ended up in the same place.

• 23:12Stephen J. Dubner?

  I think the thing that's most important or attractive about what you just said, but also very much animates your book, is that it's not just the thrill of accomplishing because something is good, it's doing something different.

• 23:26Speaker 01

  Yeah. One other aspect of this whole business is that artists, or any one, we're talking creative people, they need to not be bored. It is incredibly difficult to make something, and you have to have reasons to go on. And one of those reasons is simple interest. You have to feel stimulated. And if you do the same thing over and over and over and over again, you're just going to bore yourself to tears. The artistic person, creative person, I don't know what you want to call them, person who wants to make something, will constantly find new ways to do it because they're trying to keep themselves engaged. In my book, I mean, everybody remembers their childhood as lonely, of course. But it is definitely true that one after another,

• 24:11Speaker 01

  they describe childhoods of isolation and of need. And then something came along to fill that need. Among other things, they learn to talk to themselves. This is a big theme of my book. I think of all of this as ways of talking to yourself, as ways of translating what your imagination produces.

• 24:33Stephen J. Dubner?

  And what happened when Adam Moss's imagination started producing something new?

• 24:38Speaker 01

  Whatever lessons I might have gotten from my own magazine life that might apply to my painting life, I didn't.

• 24:46Stephen J. Dubner?

  I'm Stephen Dubner. This is Freakonomics Radio. We'll be right back.

• 25:02Stephen J. Dubner?

  In 2019, Adam Moss stepped down as editor in chief of New York Magazine. Here's what he said at the time. "I've been going full throttle for 40 years. I want to see what my life is like with less ambition. I'm older than the staff. I'm older than the readers. I just want to do something new." That new thing, at least for a while, was painting.

• 25:23Speaker 01

  When I thought I wanted to paint, I was up in Cape Cod, where I have a place, and without any, any schooling whatsoever.

• 25:32Speaker 01

  Didn't know how to do a thing. My schooling was really when I went to buy paints, I talked to the salesperson and asked them how this worked. Like, I didn't understand what a medium was. I didn't understand any of it. Nevertheless, I had this idea that I would do a painting a day. And that's what I did. One day I'd do a flower, and then the other day I'd do some crazy, stupid abstract, and then I would just make an effort at doing a person or something. The whole idea was that, at the end of the day, painting would be finished and thrown away and started over. It was fun. Came back, and I thought that was the end of it. I thought it was just a sort of fun little summer thing. And a friend of mine said, "Well, you really seem to have liked it. You really should get some training."

• 26:16Speaker 01

  She then connected me up with the head of painting, I think, at the Yale School of Art, and-

• 26:24Stephen J. Dubner?

  I can hear many listeners' heads exploding. First teacher, head of painting at Yale-

• 26:28Speaker 01

  Well, no, she wasn't my teacher. She had a student who had just graduated, who she thought was really good. And her name was Maria de Los Angeles, and she's in the book. She is a beautiful artist, but also a really lovely person. She would just come over to my house. She taught me how to draw, and she taught me how to paint at the beginning. It wasn't a particularly structured learning process, but she was my friend, my painting friend.

• 26:55Stephen J. Dubner?

  Was it built around ideas, or mostly execution, technique, et cetera?

• 26:59Speaker 01

  There was a certain amount of technique. There was a lot of just helping me find my confidence as a painter. And there was just a certain kindness that I found empowering, and a sense that she had that I had something to make.

• 27:15Stephen J. Dubner?

  Was kindness in a mentor/teacher important to you?

• 27:20Speaker 01

  It's important to me. It may not be important to other people.

• 27:23Stephen J. Dubner?

  If you look through history at creators of all types and people of all types, people who have mentors, if you had to guess, would you say that, on average, kindness is a benefit, or an attribute at least? Because when I think of a lot of- What people claim, at least, to be successful mentorships, there's often, I don't know about an absence of kindness, but a presence of something else.

• 27:48Speaker 01

  Certainly, there is an expectation that this person can do better. And I guess that can be experienced in a lot of ways as being stern and forbidding and all of that kind of thing. And I've had mentor types like that. But I personally respond to kindness. I need to feel a little loved.

• 28:06Stephen J. Dubner?

  If you were to generalize what a successful mentor is, would you use that as a template? Or do you think that's just for you?

• 28:13Speaker 01

  I think there has to be a bedrock of they have a belief in you and you have to feel it. Otherwise, the mentorship doesn't work. You have to believe that they are rooting for you.

• 28:27Stephen J. Dubner?

  I have never seen one of Adam Moss's paintings.

• 28:30Speaker 01

  That's quite on purpose, yes.

• 28:32Stephen J. Dubner?

  He insists that he is just not a very good painter.

• 28:35Speaker 01

  I'm more mediocre than bad. I'm OK, but that's not good enough for me.

• 28:39Stephen J. Dubner?

  When someone is exacting, which we have already established Adam Moss is, then mediocrity can feel worse than death. So he needed to find something else to make, something that he would be good at. And that's how he came to write The Work of Art, a book about how other creative people make something from nothing. It's a book about the process of making.

• 29:01Speaker 01

  I've always loved process because essentially I love narrative. And the act of how something comes to be is just a perfect story. Starts with nothing and then ends up something. But there's a whole other part of this book that's trying to understand the personality attributes that make someone successful as an artist. It's about half-visual, and it works almost like a giant diagram where the text itself winds around the images.

• 29:29Stephen J. Dubner?

  Tom Udic, but also magazine.

• 29:31Speaker 01

  And then it has all this footnote material, which is the me in the book, for the most part.

• 29:35Stephen J. Dubner?

  Although you're in the-

• 29:36Speaker 01

  I'm in the introductions, too.

• 29:37Stephen J. Dubner?

  Yeah, but also chapters differ because in some chapters, they're through written by you-

• 29:42Speaker 01

  Right.

• 29:42Stephen J. Dubner?

  -with quotes.

• 29:43Speaker 01

  Right.

• 29:43Stephen J. Dubner?

  In other chapters, it's more oral history.

• 29:45Speaker 01

  Yes, right.

• 29:46Stephen J. Dubner?

  And in that way, it's very much like a big, big, big magazine.

• 29:49Speaker 01

  Absolutely.

• 29:50Stephen J. Dubner?

  But it was a new pursuit.

• 29:51Speaker 01

  It was new, and yet I hope it had the benefit of a lifetime's experience as a magazine maker. I had never written a book before, and I was really scared of writing.

• 30:00Stephen J. Dubner?

  It's harder than it looks, isn't it?

• 30:01Speaker 01

  It's so hard. Unlike you, I never wanted to be a writer. I would never have left magazines for writing, but I did leave magazines at a certain point because I just felt that I didn't want to be a boss anymore. I started to write this book and I was just a terrible, terrible, terrible writer, really. And I had to teach myself. I had to use my editor head. At first, my editor had recognized that it was terrible, but didn't have any solutions in mind. And then, over time, I just began to strip it of its ridiculous ornamentation.

• 30:34Stephen J. Dubner?

  Was that all by yourself, though, or did you go to people for it?

• 30:37Speaker 01

  No, I did that mostly myself. And then eventually, OK, I got to a place where I was happier as a writer and also the work itself was better.

• 30:46Stephen J. Dubner?

  Let me just point out, the difference between being an editor and being a writer might seem not that large.

• 30:52Speaker 01

  It's huge.

• 30:53Stephen J. Dubner?

  It's like marathon versus sprint. They're both running, but I wouldn't think it could have felt so similar to what you'd spent your life doing.

• 31:01Speaker 01

  Well, OK, let me, I created the book, in the way that I created the book, in order to assemble a community. I wanted the group thing, which I always loved in magazines, and I wanted a sense of a lot of people doing something together. And so I kind of invented one. And that invention was a whole part one, which was to engage all these artists in my project. "OK, Amy Silman, show me how you made a painting and we'll go from beginning to end. OK, George Saunders, let's talk about how you wrote Lincoln in the Bardo and David Mandel, how you wrote a joke, or Kara Walker, how you built this magnificent

• 31:41Speaker 01

  sculpture, or Stephen Sondheim, how you wrote a song." And that process was essentially me recreating a context of group creation, because I thought of them as my collaborators, not as my subjects. So that was part one. Part two was writing. I described already what a hell that was.

• 32:00Stephen J. Dubner?

  And was it hell because the collaborator was no longer there?

• 32:03Speaker 01

  I'm just alone in the room again. It's the aloneness, it's the dialogue in your head that was driving me completely crazy and why I never was a writer in the first place. I just found it unbearably lonely. And also, I didn't know how to act all the parts in my head, where I could talk to myself and make myself better, which I didn't know how to do when it's different people, but I didn't know how to do in my own head.

• 32:25Stephen J. Dubner?

  So for some of the creators in your book, the people who influenced them were often people that they never interacted with.

• 32:32Speaker 01

  Yeah, possibly never met, you know, Gregory Croodson, who talked about his work as almost a mathematical formula from like William Eggleston to Ray Carver Short Stories to David Lynch in Blue Velvet. Some combination of people with sensibility that in his own mind came together.

• 32:51Stephen J. Dubner?

  Describe what a Croodson photo looks like.

• 32:53Speaker 01

  A Croodson photo is a gigantic photograph that resembles a movie still, lit like a movie with enough narrative portent, but with no before or after. So the viewer is meant to supply the narrative by looking at this picture and putting it into a context of his or her own imagination.

• 33:18Stephen J. Dubner?

  So Eggleston and David Lynch and all those make a lot of sense.

• 33:21Speaker 01

  Yeah, I in general don't much care about the strict definitions of anything. This book is a book about artists, but really I've bent the term artist just pretty much as far as it can go. And I also believe that about mentorship, which is, in the end, it doesn't matter.

• 33:36Stephen J. Dubner?

  I guess the big distinguishing factor for me would be an influence can be distant and unaware of you, whereas a mentor, there's necessarily some kind of estuarial exchange.

• 33:48Speaker 01

  Yeah, well, one interesting thing about the book was I kept looking for who is the person who encouraged you when you were young. They weren't necessarily the person who was by your side when you were an adult. But there had to be somebody, could be a parent, could be an art teacher, could be anybody, who basically saw something in them. And that seeing was crucial to the development of their confidence that they could make the thing, which of course, confidence and what I, in the book, call faith. The faith that they are actually able to make the thing that's in their head, which they can't, but you have to believe you can in order to go forward.

• 34:28Stephen J. Dubner?

  I think the book is a bit of a, not a smoke and mirror, but a bit of sleight of hand in that it's called The Work of Art, and it's plainly about the process of making creative things. And it's plainly about what it took for those creators to even get to the point where they were able to create something. I know you love process. That was a word that you said probably 30 times a day.

• 34:52Speaker 01

  And it's a word that I just have come to despise.

• 34:54Stephen J. Dubner?

  Oh, seriously?

• 34:55Speaker 01

  Well, I just, the word sounds so ugly. It's so beautiful, the thing that it's describing. And the word itself is so crude, really.

• 35:02Stephen J. Dubner?

  I feel like as a magazine editor, some of your favorite stories, or at least my conception of some of your favorite stories, were when there was a process of something being described over time.

• 35:13Speaker 01

  Absolutely.

• 35:14Stephen J. Dubner?

  And written text, not that documentary film can't do it, a lot of things can do it, but text is great at that because it can move in and out of time and it can magnify and shrink. So as much as you say that this book is about process and artifacts and so on, it was a thrill to read because I love your work and I loved working with you, but you never talked that much. You dropped hints about what made something great or not. We all learned the language of Adam Moss, but it was often fragments, rarely sentences, never paragraphs.

• 35:45Speaker 01

  I sound maddening from your description. I sound like I must have been just a horrible person to work for, but okay.

• 35:51Stephen J. Dubner?

  Maddening maybe a little bit. Horrible, definitely not. Definitely not. But maddening among nine other things.

• 35:56Speaker 01

  Yeah, okay.

• 35:57Stephen J. Dubner?

  But what it struck me the book was really about was something separate than the process of creation, really more about what it takes to become the kind of person who can create things from whole cloth. That's really hard to do, and I don't think people understand the bravery it takes to do that.

• 36:14Speaker 01

  Yeah, the book is not self-help, so I'm not sure a lot of these things can be learned. I mean, you can get better at everything, but you're either a person who can focus or you can't. You're either obsessional or you're not. You have a high tolerance for TDM, which you need to, to be an artist, or you don't. You have drive. Or you don't.

• 36:35Stephen J. Dubner?

  What about taste?

• 36:36Speaker 01

  You have taste, or you don't. Or you have a certain sensibility, or you have a certain sense of humor. These are all things that you acquire for all sorts of mysterious reasons that you and I don't understand, no one has ever understood, how personality is formed. And that all said, the book is, I hope, very encouraging to artists. Because I think most people who are trying to make things don't need to be James Joyce, or Pablo Picasso, or Louise Gluck even. They can be themselves, and they can find immense joy and satisfaction in making art. They improve their ability to focus. They improve their ability to persevere, to not give up when things get hard.

• 37:18Speaker 01

  A lot of art making comes down to something as rudimentary as being able to learn to fail. Again, like parenting, it's a little bit like a child learns to walk because they understand how they can get up from falling. They have to fall.

• 37:35Stephen J. Dubner?

  Your book nods at failure.

• 37:39Speaker 01

  I think it's a lot about failure.

• 37:41Stephen J. Dubner?

  Okay, but ultimately...

• 37:43Speaker 01

  Everybody succeeds.

• 37:44Stephen J. Dubner?

  Everybody succeeds. And so, as I'm reading it, I'm thinking, yeah, this failure is instructive and real, and useful to hear about, but it's an exercise in what some people call survivorship bias, right? We read about the winners.

• 37:58Speaker 01

  Sure, of course. And I was very well aware of that, that this is a retrospective history of success. And so, everything has to be viewed through that lens.

• 38:06Stephen J. Dubner?

  I've always had this theory that I think is wrong. But as a writer, or if you're a creative person of any type, an editor, or an entrepreneur or whatever, I think it's natural to try to mimic success.

• 38:18Speaker 01

  Yeah.

• 38:18Stephen J. Dubner?

  But I think that most successes are pretty singular.

• 38:21Speaker 01

  I completely agree with you.

• 38:23Stephen J. Dubner?

  And so, I felt that learning from failure was really the way to go.

• 38:27Speaker 01

  I wanted very much to give people permission to fail. Because failure is, if you go through the narratives in the book, there's just failure right and left. When you're trying to create something, your brain is trying to subvert you in so many ways. There are so many obstacles, and there is this kind of animus you need to have in order to barrel ahead.

• 38:47Stephen J. Dubner?

  An animus toward what?

• 38:49Speaker 01

  Animus is the wrong word. You have to have a fighting spirit, I guess I would say, where you're just not going to be daunted. Which, as I was going through this, I found very reassuring. Because of course, the reason I did the book was because I... I'd recently taken a painting and felt enormous frustration and enormous sense of failure in that. And truly, what I didn't understand is, in a group, there is a conversation that happens that's external. You and I, if we're working together making a magazine, we talk about something. There's a phrase that came up in the David Simon chapter called "The Bounce." Our method of making something better is by bouncing. I say something to you, you say something to me, bang, bang, bang. In the end, something happens which

• 39:34Speaker 01

  is better than it was when we started. In most artists' lives, that conversation has to happen in their own head. I became very confused. How does someone have this kind of inner dialogue? And that's what I was trying to understand.

• 39:49Stephen J. Dubner?

  David Simon was a police reporter for the Baltimore Sun before he started writing books and making TV shows. One of those shows was "The Wire," which many people consider one of the best TV shows ever made. If you would like to hear an interview with him, check out the "People I Mostly Admire" podcast, another show on the Freakonomics Radio Network. It's episode 109, called "David Simon is on Strike: Here's Why." We'll hear more from Adam Moss in a minute. I am Stephen Dubner, and this is Freakonomics Radio.

• 40:37Stephen J. Dubner?

  So would this book exist had you been a better painter?

• 40:41Speaker 01

  Probably not. I would not have had the drive, which was born of my own frustration. Also, I would have been satisfied painting all day, because I would, I hope, have taken a certain kind of satisfaction from the painting itself that, you know, why do you want to do anything else? I just want to do this all day long. Which now I feel, actually, not because I've gotten to be a better painter, but because I understand something about my relationship to painting that I learned from the book.

• 41:06Stephen J. Dubner?

  Which is what?

• 41:07Speaker 01

  When you say this in this context, it sounds so banal, but here I'll say it.

• 41:11Stephen J. Dubner?

  It's a hobby?

• 41:12Speaker 01

  No. Well, there's a way in which that's a description. But what I would really say is that I was trying to create narratives. And so for the narrative to work, I wanted a happy ending. I wanted an exaltation. I wanted that- Moment in the rom com with the big kiss at the end where everyone lives happily ever after. And the artists themselves, when they would get to that point in their own storytelling of their own work, refused to give me that. They would express a certain amount of relief that the thing was over. Maybe they would say, yeah, it was nice. I was glad other people got to see it and I heard some nice things about it. But you never got the big firework.

• 41:54Speaker 01

  And I found that as a writer of the book, somewhat frustrating. I kind of needed it for closure. I needed it for my own purposes, but I also needed to feel that they made something great. I was rooting for them. There was a great deal of transference involved in this book and I fell in love with all of my subjects. So I wanted something spectacular for them in the end and it never came. When I would talk to them about that, I said, well, you don't sound like that was very important. And they said, it's not about the thing I'm making. It is really about the work. I just get up every day because I like, or I need more than I like to work in this way. And the endpoint is not that relevant to me. And I just thought this was bull.

• 42:38Speaker 01

  And I thought it was bull over a long period of time. And then I was just worn down and I came to kind of grok the truth of it. I absorbed that and suddenly my relationship to my own work changed.

• 42:52Stephen J. Dubner?

  How so?

• 42:53Speaker 01

  I got enormous pleasure from what I like to think of as the verb of it rather than the noun of it. Making one mark as a painter, just like one little chew that pleased me for whatever reason, released me from this incredibly punishing attitude I had toward the work itself. I do care about the work itself. I really still want to be a good painter, but I can get pleasure out of the making.

• 43:17Stephen J. Dubner?

  It's interesting as you're describing you coming to accept what these people were telling you about their perpetual dissatisfaction because you make it sound so foreign, but that's exactly the way that I and everybody else, whoever worked with you, we describe you. When you were happy with the work that I or anyone else did, everyone described it as this like great thrill. It was like a high. Getting your approval or praise was incredibly powerful. Then there's the corollary, getting your dissatisfaction could be demoralizing for many people. You had to kind of fight through that. But the steady state was more like, yeah, it was a really good issue this week. That was it. And that implies many other things.

• 44:01Stephen J. Dubner?

  Like it wasn't a great issue and more important, there's next week also.

• 44:07Speaker 01

  That's one of the things that's fantastic about magazines. You always have next week or, you know, in a digital world, you always have five minutes from now. That's why I was particularly suited to magazines, but none of us know ourselves very well. Whatever lessons I might have gotten from my own magazine life that might apply to my painting life, I didn't.

• 44:27Stephen J. Dubner?

  To the degree that it's hard to know oneself, let's call it the internal versus the external. On a scale of zero to five, how bad or good do you think you are?

• 44:37Speaker 01

  Well, certainly not zero and certainly not five. So somewhere in that two to four range.

• 44:41Stephen J. Dubner?

  Did you become more self-aware over time and experience as an editor?

• 44:45Speaker 01

  Yeah, I think so, maybe to a fault.

• 44:48Stephen J. Dubner?

  What do you mean by that?

• 44:49Speaker 01

  Sometimes experience can be a hindrance. You stop yourself from making something. The Samin chapter, Samin Nosrat chapter, the title of the chapter is With Beginner's Eyes, because she makes this observation about salt, fat, acid, heat, that when she very excitedly at the beginning of her cooking life tells a fellow chef, the fellow chef says, well, everybody knows that. And she says, no, they don't. They don't know that. And anyway, I've never seen that anywhere. And I think people need to hear this, that this is really how you should think about cooking. And she goes on and builds this fabulous book and then a little empire off of it. Sometimes experience stops you from doing something because you know it has failed too often

• 45:34Speaker 01

  and you don't want to go through that failure again. You have to believe you can in order to go forward.

• 45:46Stephen J. Dubner?

  That was Adam Moss, the most influential boss I ever had by a mile, who did me the great favor of showing me that I didn't want to be boss, that I just wanted to make things, but who also taught me how to be better at making things. So, thanks, Adam. His book is called The Work of Art, although it might just as easily have been called The Art of Work. And the other book he just mentioned, Salt, Fat, Acid, Heat, is also well worth reading, and you can hear its author, Samin Nosrat, on a couple Freakonomics Radio episodes from 2023. One is called What's Wrong With Being a One-Hit Wonder, and the other is Samin Nosrat Always Wanted to Be Famous.

• 46:27Stephen J. Dubner?

  Coming up next time on the show, we ask, why is there so much fraud in academia?

• 46:33Speaker 03

  If you were just a rational agent acting in the most self-interested way possible as a researcher in academia, I think you would cheat.

• 46:40Speaker 04

  The most likely career path for anyone who has committed misconduct is a long and fruitful career, because most people, if they're caught at all, they skate. She was at the center of everything, being a prestigious faculty member at Harvard and all of her public speaking and her books.

• 47:00Stephen J. Dubner?

  That's next time. Until then, take care of yourself, and if you can, someone else too. Freakonomics Radio is produced by Stitcher and Renbud Radio. You can find our entire archive on any podcast app, also at Freakonomics.com, where we publish transcripts and show notes. This episode was produced by Morgan Levy and Zach Lipinski. The Freakonomics Radio Network staff also includes Alina Coleman, Augusta Chapman, Dalvin Abouaji, Eleanor Osborne, Ellen Frankman, Elsa Hernandez, Gabriel Roth, Greg Rippon, Jasmine Klinger, Jason Gambrell, Jeremy Johnston, John Schnars, Lyric Bowditch, Neil Carruth, Rebecca Lee Douglas, Sarah Lilly, and Teo Jacobs. Our theme song is "Mr. Fortune" by The Hitchhikers. Our composer is Luis Guerra. As always, thank you for listening.

• 47:50Stephen J. Dubner?

  I'm gonna shut up. Can you just say that again? Gigantic. No, say it the way you did. Gigantic.

• 48:00Speaker 02

  The Freakonomics Radio Network, the hidden side of everything.

• 48:07Speaker 04

  Stitcher.