How to Make Something from Nothing

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 L.A. 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.

DUBNER: Why don’t you just say your name and what you do. 

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

For a long time, Adam Moss was widely considered the best magazine editor around. He was the founding editor of 7 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 of a book, called The Work of Art: How Something Comes from Nothing.

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

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’s 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’ll 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. 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 thirties — that people would think you’re crazy. I was doing well as an editor and an occasional writer; 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 for 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 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 just 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; 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.

*      *      *

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’s 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. 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.

MOSS: So many things. First of all, when I came to love magazines, it was the late ’60s, early ’70s. It was a 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 was just very attractive, and the magazines that I loved — like the New Yorks and Esquires, etc. — they were a little smartass. 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, if it appealed to you, it was very powerful. It felt very personal. 

DUBNER: So this was the medium that you loved, and then you sought it out? And then who —

MOSS: Okay, so I had all of this stuff in my head, but it was unformed. And I went to work at Esquire. I was very young. I was a very unformed person at that point. 

DUBNER: What were you good at? 

MOSS: I was probably fairly intuitive. I certainly was eager. And I had 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 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. 

DUBNER: Name some things that you would do there on a given day.

MOSS: 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 Candice Bergen. My job was to 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, it’s an incredible way to learn. 

DUBNER: I mean, it’s apprenticeship. 

MOSS: 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/mentee kind of thing, it goes both ways. 

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?

MOSS: 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 —

DUBNER: New eyes, fresh eyes.

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

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 the magazine? I think a lot of people who aren’t writers or editors —

MOSS: Don’t really understand that. 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. A 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. 

DUBNER: Although you did your share of that. 

MOSS: 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. 

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.” 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 —

MOSS: 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. 

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 controlling — you’re not writing the articles, you’re not editing the articles heavily. So how do you live with that paradox? 

MOSS: 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 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 exactinghood 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. 

DUBNER: How much of that was in the hiring, though?

MOSS: 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 equilibrium, but that was what I was after. 

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

MOSS: 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. 

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 8, 10, 12? You had very different relationships with each one. How does that work for you? Is it a choice?

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

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. 

MOSS: 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 —

DUBNER: And very different relationships with their parents. 

MOSS: 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 withering comments.

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 the boss. You just didn’t see it.

MOSS: 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 aghast! 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. 

DUBNER: Meaning the younger people taught you, like, this doesn’t feel good.

MOSS: This doesn’t feel good, and this doesn’t —

DUBNER: Did you stop? 

MOSS: Well, I found workarounds. I found other ways to try to accomplish the same thing. 

DUBNER: For instance? Just different language? 

MOSS: Probably I learned to praise and then to withhold. 

DUBNER: So that was a strategy? 

MOSS: 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.”

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.

MOSS: Oh no.

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? 

MOSS: I don’t think so. I hope not. 

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 —

MOSS: “If they can turn in stuff like that, I can do this.” 

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 I was a lame duck. 

MOSS: So what, did I just not care about you anymore because you were not going to be a long-term asset for me? Was I that calculating? 

DUBNER: I wouldn’t say it was that. I think it was more like plow-horse idea. 

MOSS: Get as much out of you as I could.

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’d 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. We’re a company. We have 20 people. And I think the boss that I became is very much like the boss that you were. 

MOSS: Oh, really?

DUBNER: Oh my God, yeah. 

MOSS: Now, is that just natural, or do you think that you learn certain attributes of a boss person from me? 

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. 

MOSS: Oh, how interesting. God, that’s scary. 

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?”

MOSS: Definitely. That’s a big part of it. 

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. And those are all things I learned from you. 

MOSS: 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. 

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 partners, 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.”

MOSS: 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 —

DUBNER: You can say “for” you, it’s okay. 

MOSS: — 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. 

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. 

MOSS: Yeah. One other aspect of this whole business is that artists or anyone we’re talking about — 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, they describe childhoods of isolation and of need. And then something came along to fill that need. Among other things, they learned 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. 

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

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

*      *      *

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.

MOSS: When I thought I wanted to paint, I was up in Cape Cod, where I have a place, and without any schooling whatsoever, 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 I 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 start it 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.” She then connected me up with the head of painting, I think, at the Yale School of Art, and — 

DUBNER: I can hear many listeners’ heads exploding: first teacher, head of painting, Yale School of Art!

MOSS: Well, no, she wasn’t my teacher. She had a student who had just graduated, who she thought was really good. 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.

DUBNER: Was it built around ideas or mostly execution, technique, etc.? 

MOSS: 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. 

DUBNER: Was kindness in a mentor-slash-teacher important to you? 

MOSS: It’s important to me. May not be important to other people. 

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. 

MOSS: 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. 

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? 

MOSS: 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. 

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

MOSS: That’s quite on purpose, yes.

He insists that he’s just not a very good painter.

MOSS: I’m more mediocre than bad. I’m okay, but that’s not good enough for me. 

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.

MOSS: 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 with 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 —

DUBNER: Talmudic but also magazine-ish.

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

DUBNER: Although you’re in the —

MOSS: I’m in the introductions too.

DUBNER: Yeah. But also, chapters differ because, in some chapters they’re through-written by you, with quotes. In other chapters it’s more oral history. In that way it’s very much like a big, big, big magazine. 

MOSS: Absolutely. 

DUBNER: But it was a new pursuit. 

MOSS: 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 — 

DUBNER: It’s harder than it looks, isn’t it?

MOSS: 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 — and at first my editor head 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. 

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

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

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

MOSS: It’s huge. 

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. 

MOSS: 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. “Okay, Amy Sillman, show me how you made a painting, and we’ll go from beginning to end. Okay, 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 sculpture, or Stephen Sondheim, how you wrote a song.” And that process was essentially me re-creating 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.

DUBNER: And was it hell because the collaborator’s no longer there?

MOSS: I’m just alone in the room again. It’s the aloneness. It’s the dialog 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 did know how to do when it’s different people, but I didn’t know how to do in my own head.

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

MOSS: Yeah. Possibly never met. You know, Gregory Crewdson, who talked about his work as almost a mathematical formula, from like, William Eggleston to Ray Carver’s short stories to David Lynch in Blue Velvet. Some combination of people with sensibility that in his own mind came together. 

DUBNER: Describe what a Crewdson photo looks like. 

MOSS: A Crewdson 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. 

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

MOSS: 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 pretty much as far as it can go. And I also believe that about mentorship, which is in the end, it doesn’t matter. 

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.

MOSS: 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, or 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. 

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. 

MOSS: And it’s a word that I just have come to despise. 

DUBNER: Oh, seriously? 

MOSS: 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. 

DUBNER: 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. 

MOSS: Absolutely, absolutely. 

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. 

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

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

MOSS: 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 tedium, which you need to be an artist, or you don’t. You have drive, or you don’t. 

DUBNER: What about taste? 

MOSS: 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. 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 Glück 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. 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.

DUBNER: Your book nods at failure.

MOSS: I think it’s a lot about failure.

DUBNER: Okay. But, ultimately— 

MOSS: Everybody succeeds.

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. 

MOSS: 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. 

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. But I think that most successes are pretty singular. 

MOSS: I completely agree with you. 

DUBNER: And so I felt that learning from a failure was really the way to go.

MOSS: 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 try 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.

DUBNER: An animus toward what? 

MOSS: 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 had recently taken up painting and felt enormous frustration and almost a 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 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. 

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 in the Freakonomics Radio Network; it’s episode 109, called “David Simon Is On Strike. Here’s Why.”

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

MOSS: 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.

DUBNER: Which is what? 

MOSS: When you say this in this context, it sounds so banal — but here, I’ll say it. 

DUBNER: Uh oh. It’s a hobby?

MOSS: 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. 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****. 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

DUBNER: How so? 

MOSS: 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 “choo,” 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. 

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 who ever worked with you would describe you. When you were happy with the work that I or anyone else did — everyone describes 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, like, it wasn’t a great issue. And more important: there’s next week also. 

MOSS: 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. It’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. 

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?

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

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

MOSS: Yeah, I think so. Maybe to a fault. 

DUBNER: What do you mean by that? 

MOSS: 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, and you don’t want to go through that failure again. You have to believe you can in order to go forward. 

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 a 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.”

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Freakonomics Radio is produced by Stitcher and Renbud Radio. This episode was produced by Morgan Levey and Zack Lapinski. The Freakonomics Radio Network staff also includes Alina Kulman, Augusta Chapman, Dalvin Aboagye, Eleanor Osborne, Ellen Frankman, Elsa Hernandez, Gabriel Roth, Greg Rippin, Jasmin Klinger, Jason Gambrell, Jeremy Johnston, Jon Schnaars, Lyric Bowditch, Neal Carruth, Rebecca Lee Douglas, Sarah Lilley, and Theo Jacobs. Our theme song is “Mr. Fortune,” by the Hitchhikers; our composer is Luis Guerra.

DUBNER: I’m going to shut up. Can you just say that again? 

MOSS: Gigantic.

DUBNER: No. Say it the way you did. 

MOSS: Gigantic!