Having A Motor with Bob Mankoff

INJ 58 | Cartoons


Bob Mankoff is the Cartoon and Humor Editor for Esquire and former New Yorker Cartoon Editor. A student of humor and creativity, Bob has devoted his life to discovering just what makes us laugh, and seeks every outlet to do so, from developing The New Yorker’s web presence to integrating it with algorithms and A.I. He kicked off his career by quitting a PhD program in experimental psychology at The City University of New York in 1974. Shortly after, he began submitting cartoons to the New Yorker. Three years and over 2,000 cartoons later, he finally made the magazine and has since published over 950 cartoons.

Listen to Episode #58 here

Having A Motor with Bob Mankoff

Our guest is Bob Mankoff. He is the Cartoon and Humor Editor for Esquire and former The New Yorker Cartoon Editor. A student of humor and creativity, Bob has devoted his life to discovering what makes us laugh and seeks every outlet to do so, from developing The New Yorker’s web presence to integrating it with AI. He kicked off his career by quitting a PhD program in Experimental Psychology at the City University. Shortly thereafter, he began submitting cartoons to The New Yorker. A few years and over 2,000 cartoons later, he finally made the magazine and since has published over 950 cartoons. Welcome, Bob.

I’m delighted to be here.

It’s a great pleasure to have you. If you weren’t a cartoonist, editor or a writer, what would you be doing with your life?

I’m an intellectual Mankoff, that’s my vent. That’s why I went into experimental psychology. I’ve always been curious about things and funny. I always wanted to be a cartoonist before I wanted to be a psychologist or anything else. I was drawing cartoons at seven even right after college. I would have been if I wasn’t a cartoonist, the two avenues that opened up to me would be stand-up or do something in comedy. I grew up in Queens and where we would vacation which was in the Catskills, in the Borscht Belt, I saw comics. It was a model. I understood part of Jewish culture is there’s a strong humor element, whether it’s jokes, philosophical humor or worldview.

When you look at who the comics were in the 20th century before there were stand-ups because no one called it stand-up. Stand-up is a relatively recent term. If you go to a Google Ngram and you put in stand-up like when it tracks, it starts to happen in the ‘60s. When I grew up, it was a comic. The comic came on between acts. There were no shows at all in which it was a comedy show. I had that model. I always would have flunked out of the PhD program. Therefore, I had to do something. It would have been something in comedy.

That’s interesting because you said you would’ve flunked out of your PhD program anyways. Yet you have two elements that make for a great academic. You chose well despite your aptitude. You have a deep curiosity. What I notice is the more successful academics are naturally curious people, which is necessary in a world which has lots of failures. The best academics are focused on process, answering puzzling questions, diving down the rabbit hole sometimes to find nothing. Having curiosity is a predictor of success and you have that clear early on and you still do now. The second thing is you have a motor. You work hard. You work a lot. You push yourself, it’s clear. Even the story of getting here to do this show is a testament to your motor. Let’s talk about that first. Are you an athlete?


What athlete are you?

[bctt tweet=”One of the things that are interesting about humor is being on the top means you get the right to interrupt and make jokes and whatever.” via=”no”]

I would say there is no question that all the people in comedy and I don’t care what age they are, I am the best jump shooter. You look up YouTube, even as I go into my final lap, my final quarter century, I hope I make it, I can still make twenty jump shots in a row. I’ve got a video of me making twelve three-pointers in a row. I’m a good athlete. I played high school basketball. In my day, I could dunk a basketball.

How tall are you?

I’m about 5’11.5”

As an aside, this is for the reader. I’m 6’5” and in my day I could dunk a basketball. I think I’d have to train deeply to be able to dunk a basketball again because those days are behind me.

I also ran the second, third and fourth New York City Marathons. I ran the marathon when there were 226 people on it. When you take a motor, I’ve always started things because I wanted to do that. When I ran a marathon in ’71 four times around Central Park and another two miles, there were a lot of people who wanted to do it, but I wanted to do it. I’ve always been driven about what I want to do. Why I flunked out of the PhD program is because it didn’t permit my curiosity. It was the hay day of behaviorism. I was training pigeons. I wanted to do an experiment to tell how do you know if a pigeon is right, wrong, making a mistake or lying? They didn’t want that. They wanted these schedules of reinforcement. I was always looking to do things creatively. At that time behaviorism, it’s not unlike benign violation, a Polemical Theory. It’s a great arguing theory. I’m not disparaging benign violation. What I’m saying is it would be scary and stuff had because so much of what we’re saying was strong. You had all your arguments in place. For a while, I was drinking that Kool-Aid. All of a sudden, what happened has happened to me many times in my career I said, “I don’t believe it.” Then I was in an organization that had to believe it.

You’re in the wrong system.

I’ve always been in the wrong system. Wherever I am, especially in corporate life and everything, I’m always in the wrong system. Because in corporate life wherever you are, no matter what the corporation is, whether it’s the New Yorker or Hirsch’s, there is an organizational group thing. There is the feeling that within the organization the most important thing is whoever on the top is happy. One of the things that are interesting about humor is being on the top means you get the right to interrupt and make jokes and whatever, whether they’re good or bad and people will laugh because that’s the power dynamic.

INJ 58 | Cartoons
Moral Mazes: The World of Corporate Managers

If someone in any subordinate position, for better or worse than the way I was insubordinate positions. If you’re funny, that’s power and it upsets that dynamic. I’m a person with lots of ideas. That is unsettling in an organization. They don’t like it. It’s suspicion about even the appearance of brilliance. Now I’m old, I’ve come to terms with all of that. In my travels around academia, what I’ve found is they’re not curious for the most part. When I would go to different places, everyone has their little silo. You’re different than that. You want to break out. They’ve got the hobby horse that they’re writing. I always find I want to challenge not only what other people are thinking what I’m thinking. I don’t think that gets you from far in academia.

First of all, I’m not surprised to hear you are an athlete. Because I think that those having like a physical motor translates into benefits and all these other even intellectual ways, the ability to work for long hours, to be able to focus and the notion you can train yourself.

The focus on things that are ostensibly worthless like shooting baskets. I watched Steph Curry shoot the baskets and I said, “How is he doing that? How is he shooting from that distance?” I realized my jump shot, which was formed in the late ‘50s and ‘60s is that two-stage thing where you put it over your head, slingshot, old school. His is this one motion. I spent all of the last summers transforming at 74. What happened was a nice place out in West Dresser. For my birthday, my wife let me put up a basketball court. I have the NBA three-point line, everything. I’m out there shooting with a GoPro and then I’m analyzing it. Why would anyone spend all these hours at 74 doing that? Going back to the book of the ‘50s, The Lonely Crowd, I’m not other-directed.

In other words, other-directed is you’re doing what other people value. I am not doing what other people value. That’s extreme. I’ll give you a good example. I bought a top for every spin. It’s a cool top. It’s like a gimmick like a fidget spinner. For every spin which make titanium tops, they follow me around the internet forever because I broke their top. They’re stalking me because I bought a top. I want to go wherever they are in Canada. I wasn’t that pleased. I said the top echo and it goes for a minute. What can we do with this top? I got a plastic so it spins forever. I said, “We should make a game where you have to go around a course.” With a magic marker, I made the course. I did that for a day. I got interested. It was like, “What’s the best plastic for this top to spin on? What’s the course I should make?” That’s what I mean but I’m not other-directed. It’s a silly example.

It was a good example. Your argument is you’re too curious for academia.

Not only academia but even for editorial processes, whether it’s The New Yorker or Esquire. In other words, I kept wanting to push these algorithms and see what we could do. The editorial places or business places, what they want to ask is what the point is? You have to give some, “This is a goal and we’re ready.” It was some bottom line or audience or anything. To be curious and intellectual, it’s like pure science and research. I always feel these things will be useful in some way or that one tangent or offspring might. Even if they’re not, they are worthwhile doing in themselves. One of my mantras in life is leave no joke unjoked. Why? Wherever it comes. I didn’t to you, but almost in every email I write, I try to do something and be a little bit funny.

In interacting with people, I try to be funny. It’s a way to be both being curious and being funny is looking at everything, whether it’s the Starbucks thing. Let’s say I’m at the Hearst Cafeteria, which is not the Hearst Cafeteria. It turns out it’s Cafe 57. I had a meeting with someone at the Hearst Cafeteria. I said, “It’s Cafe 57. I should have called the maître d’. On Hearst Cafeteria, it says, “Occupancy by more than 691 people is dangerous,” or whatever. My thinking is by the time you get to 684, you should be worried. It’s like the thing with Viagra. If your erection for four hours, I think at three hours and 50 minutes, you already should be thinking. I’m always trying to reconstruct the world in that way.

I made an argument that curiosity in academia is a linear effect. You’re making an argument that it’s nonlinear, that it’s an inverted U. That there are some ideal amount of curiosity but too much can get you into trouble. In part because system A doesn’t fully value it  and then B, you might dance around a little too much. One of the issues with academia is you go narrow and deep. When you like to play with new ideas and try out different things, spend a day doing these things, it gets you away from keeping your eye on the prize, which is publishing these dry, esoteric papers that take years to do.

That’s true in organizations. I’m reading a wonderful book called Moral Mazes, which was written in the 1980s about the morality and the situational ethics within corporations. It’s like one of these books. It’s a fantastic book. It’s almost in the mode of Erving Goffman, The Presentation of Self in Everyday Life, where it shows you what’s happening sociologically within organizations. It’s one of these red pill books. They’re like, “Once you read it,” you say, “Nothing could’ve happened at Boeing other than what happened.” If anyone would have said at any time, “We’re not going to either sell these planes or we’re going to spend $50 million or $60 million on extra training and things because of a catastrophe that might happen.”

[bctt tweet=”If you’re funny, that’s power.” via=”no”]

This book shows many examples. You will get fired for that. How many people will do that to get fired? For the most part, the catastrophe doesn’t happen. All that happens is you get fired. I also understand within organizations that any organization I’ve been at. You said, “I work hard.” I’m always amazed at how much people work and I hardly work at all. I sit there and we’ll gather and think. This sounds grandiose. When I drove in, I was listening to the radio. I said, “Who needs this radio? Do I have to hear about Trump again and the weather again?” I shut it off. I said, “People talk about meditation which is clear your mind.” I hate that. I don’t want to clear my mind. This is the first time I had this idea of thinking. In other words, remove all stimulation. Most of the time, the way we’re thinking is in reacting to other things.

We’re reading and thinking. We’re looking at things and thinking. You’re drawing and thinking, but take out all stimulation. I said, “I’m going to meet with Peter McGraw.” That’s why I started thinking about the benign violation. I don’t have to get into that and what makes a joke funny separate from that. All the ideas we’ve discussed. I want to think. I want not to do anything, not to be reactively thinking or even productively thinking towards a goal but to think. That’s my new thing. People often ask you things like, “What have you read lately?” Now my new question is, “What have you thought lately?”

My final question for every person in the show is what are you reading, watching or listening to that’s good? I may be asking you what are you even thinking about what’s good? You’ve touched on a couple of things that I’ve been puzzling over and thinking a lot about. The first one is you and I are a little like in the sense that I like to try new things. I like to go broad. I don’t always fit in. One of the problems I have as a result of doing that is I don’t feel like I finish a lot of things. Things take a long time to do because I’m spread out across many different types of projects.

When I was going up for tenure, I contracted my interest. I stopped playing around with research ideas and I became closer. I got good at publishing papers and placing them in high-level journals. Having accomplished that, I’ve started to play around again. When you play around again, you start podcasts and you do these kinds of things, it makes it hard to finish things. The timelines for almost all of my big projects have been pushed out. They feel like years at times. I’ve been working on this idea and maybe it’s artist’s perspective is the outcome doesn’t matter. It’s the day-to-day process that matters that can I work on things I find to be perplexing, challenging, lead to these engaging flow states that are useful. It seems to me that you do that. Your example of shooting baskets and filming yourself, my guess is the world melts away when you’re doing that. There’s nothing else in the world but that ball.

It’s aesthetic. Like you, I’m doing many because I get the plugs in here, but it makes sense. I’ve started CartoonCollections.com, which is an auxiliary or replacement for the Cartoon Bank, which I also founded. I bought the Cartoon Collections. I had to spend acquiring CartoonStock in England. That’s a whole other business. I started at an AI humor company with Jamie Brew called Botnik, which takes texts like all the texts of Harry Potter. Just as we have predictive texts on our phone, it puts it into here. Now, you’re writing like JK Rowling but to a very humorous effect. I’m working all those things. The way I’m looking at it is this. I co-founded Botnik, which is a business now though it’s not making any money.

You don’t have to make money to be considered a business.

In fact, often it’s important that you don’t. The idea is to use AI in combination with people to produce creative things. Jamie, when I started was 26. He’s 28 now and I’m 75. I view what I’m doing whether it’s Cartoon Collections, which will be this business with licenses that will organize the world’s cartoons. I’m bringing young people into that. Esquire as frankly a legacy, things that will continue after I’m not here that I planted the seeds for so I don’t have to accomplish. The other thing where I’m viewing things is I don’t have to do everything that there are organizations where the networks you create have a collective intelligence that produces it. This idea that you individually have to produce it.

I’m working with Jamie and Jamie looks like he might get a job at Google where people who are also interested in this. It’s the things you set in motion. It’s the lives that you influence along the path you are interested in. This idea that I may never complete any of these things. I know somewhere down the line, maybe when I’m alive, maybe when I’m not there, that CartoonCollections.com is going to be giving lots of money to cartoonists and support this profession which is hurting. I know that this idea that AI in combination with human beings will be able to create things that neither one can, I know that will happen. I know I’m part of those things. I know that Esquire now has cartoons in it and that there is a cartoon and humor editor and it’s me. I won’t be the cartoon and humor editor forever. Maybe now there will be. Those are the way I’m looking at.

INJ 58 | Cartoons
Cartoons: It’s not important whether you believe what you’re saying. What’s important is does it make sense?


You still do have an outcome focus.

Maybe it’s a rationale because we’re in this conversation. Belief is funny. The things we say are funny. Often I find that the linguistics or the rhetoric of my ideas drive my conclusions. I had an interesting argument with someone who says, “You don’t even believe what you’re saying.” I said, “So what?” They couldn’t handle that idea that somehow we had to believe the thing we were saying. It’s not important whether I believe what I’m saying. Who even knows how that would operationally be defined? What is important is does it make some sense and I think it does make some sense.

Some of my favorite psychological researches on what’s called motivated reasoning. Our ability to draw arguments and counter argue based upon what we want our outcome or belief is to be. There was a paper that showed that intelligent people are even better at this. You could imagine two hypotheses. One is smart people recognize that they’re motivated and they’re seeking the truth so they counteract their motivated reasoning. That is not the case. The smarter you are, the better you are at motivated reasoning because you’re better at making an argument.

A counteractive to this is to read philosophy. Go back to the Greeks, go back to the skeptics. Not learn logic, learn skepticism of your own idea. Deep skepticism that not only may you be wrong, but you’re probably wrong because people are wrong all the time. That interrogation where it’s almost in a way in which you start to doubt or use the call popper thing of falsifiability. I’m saying this stuff about global warming or against it. What would it take for me to think I was wrong? When the answer is nothing, nothing could be worse. That’s a situation I don’t want to be in. I want to define the ways. I have to explain it to myself. I have this opinion about X. What would it take for me to say I’m wrong? Most people will say, “Nothing. It’s obvious that is whatever.”

There’s a strong argument that I feel people have been making is we’re certainly wrong about most things because if you look historically at what we’ve believed, we’ve been wrong. Five years, 50 years, 500 years from now, people will look back at the things we thought and did and think, “How could those people be so wrong?”

One of the things they say is, “Why will they be right?” It’s what I call chronocentrism. We assume based on our own lives that here we were at point A in time and here we are now at Point B in time. We know we made this mistake at A in time and now we know at B that was wrong. We assume somehow the same thing. It doesn’t exist for a lot of things. The time we’re in, we always think we know more previous than the time previously. That might not be completely true. We know more about some things. This is my philosophy of extreme doubt. It seems obvious that the later time knows more than the previous time, but maybe it’s a time-centered egotism.

That’s fair although the one thing that you can easily point to are advances scientifically and so on.

It’s small in terms of our philosophy, socialism, Marxism, capitalism and everything. We think the end of history. In 2000, it was all over. It’s done and you see that we turned out a certain way. Now, we know that. We know that wasn’t true, but maybe it turns out to be true later. One of the things I’ve often thought about this weird thing is that in terms of arguments. The arguments are ex cathedra from the chair, from authority. My personality is contrarian and anti-authority and I’m always questioning. It’s not that I doubt climate change. It’s just that I want to know, “What are the surrogates? You asked the question, “You don’t have anything before the 1880s and now you have the proxy rings or the ice samples. How accurate are these?” When you look at the surrogates, how would we know? One of the things broadly you could be on a liberal side because you can’t ask these questions anymore.

[bctt tweet=”To be curious and intellectual is like pure science and research. These things will be useful in some way.” via=”no”]

This came up a little bit. I did a previous show with Jason Zinoman and Luisa Diez, this notion in comedy especially of political correctness. There’s a natural tendency to want to shot down topics. There are things that can’t be talked about and so on. This is obviously happening not just in comedy but in politics and in science and so on.

In terms of Esquire, I’m going to propose that we have a panel cartoon called, “Should You Be Laughing At This?”

Given my background and what I’ve been studying, it’s a very interesting idea.

I liked that because it gives you a little cover. Some of the things for Esquire is I have ideas and some are people. A cartoon that’ll appear in the issue, my idea and the science is toxic, masculinity detox center. The sign in the window is walk-ins welcome. I did a cartoon for Esquire, the doctor is looking at the guy’s chart and says, “So far the masculinity seems to be not benign, but let’s keep an eye on it.” These things, I try to use humor to interrogate the culture and where we are. I have been almost always on the side of free speech and offense and understanding that joke worlds are fantasy worlds like horror films are. It’s always interesting to me how comedy becomes the scapegoat. Here we have a culture of a video game incredible violence, of horror films. Look at a horror film. Do you think people should be enjoying watching other people get killed? Is that a good idea versus a joke in which a woman is saying, “I’ve only been gluten-free for two weeks, but I’m already annoying.” That will get you thousands of letters. When I showed that from the audience, I said, “This is not about people who have celiac disease. This is about people who wish they had celiac disease.”

I want to ask you about the second thing. One is this process outcomes, finding joy and enjoyment. I think of it as engagement. Joy is too strong a word. From the process of getting up, doing the work, challenging yourself and being creative and doing that regularly will lead to these legacy-enhancing outcomes. The other one is something you said earlier that raised an idea that I’ve been fussing around with is this notion of not catering to the masses. The notion of creating an audience of one and you, the creator, being that audience. I like this idea because I find it freeing as someone who’s trying to create. I also though find it unsettling because one of my many jobs is that of a marketing professor. I talk to my students who want to be business owners, business creators as identifying a market and serving their needs. Those two things can be squared.

It’s like a benign violation. There’s a sweet spot there. The sweet spot is it’s not an audience of one. An audience of one is you’re in your art studio and you’re in a hallucinatory world and there are markets for this crap. All of a sudden you decide, “I want to bend automobile fenders into different shapes because I want to do it.” If you can get somebody who looks at that as an asset, but nobody viscerally ever looks at it like they do Michelangelo or anything like that.

Let’s take something a little bit different. Let’s talk about a musician or a writer, who they write something and they make something that they know pleases them.

This is how I put it to people that want to be a cartoonist saying, “If you do this work, everybody doesn’t have to like it and everybody doesn’t have to pay for it.” If nobody likes it and nobody pays for it, you’ve been doing the wrong work. There’s an audience. You could look at it statistically in the bell curve. You could look at it and say the mass audience likes crap. They like the worst possible thing. That’s what the internet is. Can you believe this lion ran around with a turtle? It’s the fly in the ointment of democracy itself. George Carlin has a cool joke. He says, “You’re not stupid as someone is with a 100 IQ. Half the people are dumber than that.”


This is what you’re dealing with. The fact is which is absolutely cruel to say, “If you have an average IQ of 100, you can’t go to college. There are many cognitive tasks you cannot do. You’re not going to appreciate all great art or complicated writing.” The other way I feel out of it is this, imagine this pyramid. This is marketing and money. Here it is the world’s smartest guy or woman. They’re smart that only two other people could even understand what they’re saying. It’s not a big market. I should go down that intelligence creating pyramid. There’s a sweet spot. The 140s are talking to the 120s. The 120s are good because of the 120s, don’t get me on IQ and stuff like that. I’m saying whatever you want to talk about smarts, whatever you’re talking about expertise or whenever, they’ve risen in society.

It’s like Coltrane as he became a master jazz musician, he started doing jazz. Half the audience were blown away. They’ve never seen anything like it. The other half of the audience left the arena as he moved up.

I think eventually genius moves away from all audiences because they are inward-directed rather than other-directed. That’s a train that starts and ends not in a good place because of ego, because of wealth and everything. They want to keep pushing it. People have grandiose ideas of what they accomplish, which is that, “I want to make a breakthrough. I want to do something no one has ever done before. For me, for example and for most people there’s a sweet spot in jazz where there’s lots of inventiveness, but there’s still some connection.

You’re using IQ as a model by which to talk about segmentation. I think that’s fair. If you want to pay the bills and if you want to have some effect on the world, you need a group of people who care.

You can be both. In other words, you can understand as an editor in a magazine, I’ve got an audience. I’m going out there to do a particular thing for that audience. Not the little bit of a sweet spot, please me and please the cartoonist too but saying, “It still got to resonate with the audience.” If there was a different audience, let’s say on Cartoon Collections we created our own magazine, which is for cartoon aficionados, then it might be a whole different cognizant you would be appealing to. It’s still an audience. It’s like everything. You’ve got to know the room.

I want to get your reaction to this idea because this idea of an audience of one is an interesting idea because what it can do is set in motion a creative endeavor that is highly risky and highly rewarding. That is that most audience of one effort will yield a product that only one person loves, the person who created it. However, when it does yield something that a broader audience enjoys, it has the chance to be especially enjoyable because it’s more likely to be different. That is the act of creating something for an audience now pushes you in a less creative process, one in which other people are likely to do so. Going to the musician idea is like if I’m a band and I want to create a song that my audience is going to enjoy, am I creating something the same old type of thing versus when you see a band goes into the studio and tries to do something new. Sometimes that is met with derision, but sometimes it’s a breakthrough in the sense of that. I’ve enjoyed this idea is that it’s fine to pursue that, but you have to know. You might create a song that only your band likes.

The interesting thing is whether from a personality viewpoint, from a temperamental viewpoint, that can be inculcated in someone for whom it’s not congenial. What I’m saying is I know a number of cartoonists and some of them, particularly a guy like Ed Steed, he is inner-directed and he does connect, but basically he’s doing what he likes. He’s set up that way. We can’t take what you’re saying out of the whole personality matrix of a person. The interesting thing always is, “You’re this person who is a crowd pleaser, who cares about people, but if you want to succeed, you should try to be this other person.” The counter-argument I would make is people don’t change. Maybe it’s still useful in all fields and the fields may not even be creative fields. I can’t be anybody but I am. I can pretend to be somebody else for a short period of time when a package didn’t get delivered. I never get angry. I usually get depressed, morose and unhappy. Whereas a person I know well, I’ve been married for 26 years, really gets pissed. All of a sudden, I channel my wife, Cory, saying, “Where is that FedEx package?” For that moment, I think sometimes these cognitive behavioral techniques could be helpful in all things.

Imagine you’re an audience of one and I think you’re making a good point, the question is it seems like some people are set up. When you look at Roz Chast’s early work or her work in general, clearly it’s her inner world which is powerful for her. Whereas if you look at many cartoonists or even great cartoonists, one of the things I’ve said is, “If you saw Roz Chast cartoons, you know a lot about Roz Chast.” If you saw somebody else’s cartoons, you could say, “They’re even a great cartoonist,” but you know nothing about it. You don’t get any insight. Who are you to start with? You’re making an interesting point about it. Those people who are on the far end of not connecting then are the people often who become the geniuses or do connect in a wide and interesting way not only for their time, but they have longer careers even after their careers are over as their work is appreciated.

[bctt tweet=”Leave no joke unjoked wherever it comes.” via=”no”]

I’m not making a strong argument. It’s an alternative path. It’s one I’ve been thinking more about. I have the luxury of being a tenured professor and a steady paycheck, which allows me to ramp up risk. Which is interesting because academics typically are not risk-seeking people. They are government workers. They chose the safety of academia and I did too. I chose academia because I didn’t want to be homeless and poor and I was seeking safety and security. Then I got it and I realized that I’m no longer living in a scarce world. I’m living in an abundant world. What might I be able to do as a result of that?

You’re acting like you’re an immigrant off the boat here scrambling on Hester Street. You would have done fine no matter what you did.

That’s not my identity.

It’s good that they have that identity.

I’ve had to work to recognize my privilege. I’ve recognized it and I appreciate it. I try to leverage it in a way that’s not too obnoxious. I’ll give you an example. This is for the audience. I’m working on a new secret project.

It is so secret that he’s going to tell you about it.

It’s the launch of a podcast. I’d been sharing the copy, the description of the podcast and so on with a number of confidants, people who I trust their judgment and their discretion. You get mixed feedback. A part of me is like, “I should write the copy that is going to be best and let the chips fall where they may.” It’s difficult for me to do something for myself fully. I’m constantly looking for advice and getting feedback. It’s the experimentalist in me. It’s the tester in me. I can’t say that I have landed firmly on this idea. It’s one I’ve enjoyed thinking about and talking about. It’s been a topic on this podcast a number of times. Another topic that’s been on this podcast is about how people structure their day and they structure their creative time. I’m curious about that with you. You submitted over 2,000 cartoons before you made the magazine. You’ve published 950. There are probably twenty times that number that you’ve drawn and haven’t published. I’m curious, you get a lot done. Part of it is because it’s motor. Tell me about your day, tell me about your creative process. How do you go about drawing cartoons and so on?

I don’t draw as many cartoons anymore because I have all these other things. I come up with ideas. I draw a few cartoons for Esquire, but I’m no longer a cartoonist. I have this whole entrepreneurial thing. I’ve got to make Cartoon Collection and cartoon work.

INJ 58 | Cartoons
Cartoons: We do little of thinking now because we’re in this world of incredible entertainment and distractions.


Let’s say in your prime Mankoff?

In my prime period, I would get up and I would go to the drawing board. I used to spend hours and hours reading the papers, thinking, getting ideas and looking at ideas that I had done before. Taking a nap, drinking coffee, getting up and drinking coffee. I would have two days.

Do you mean two days in a day?

Two days in a day you would get ideas. There would be a period early in the morning where you would get ideas and work through them. My life at that time, my mind was always on for ideas constantly in the world. It was in a way an unpleasant and narrow experience. You have to work and enormously hard to get the ten or twenty ideas every week. The structure was that my conscious and unconscious mind was always in the back processing material. I’m sure standups are doing that also. I’m delighted I’m no longer doing that.

Were you single at the time?

I was single, married, single and married. I’ve been married three times. I’m sure this is true for stand-ups and other people where there’s so much of your mind is eaten up by this natural talent or propensity that you have that gets blown out of all proportion.

You don’t seem terribly wistful about doing this.

No, I’m not. First of all, I did what I think is good work. It’s a young person’s game. The idea that creative comic art goes on forever. It doesn’t. I always had other interests from the start. I was never singly looking at that. Fairly early, I got into The New Yorker in ’77. By 1984, I had burned out. I went through other periods and that’s why I started the Cartoon Bank.

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You did several hard years of cartooning.

I said, “The rest of my life, I don’t want to be the guy who is putting in a piece of paper asking someone else if it’s funny and then pay the rent.” In a practical way, this isn’t a safe occupation. Tastes can change. Editors can change.

You only have a limited number of outlets. That’s something that I always talk to my students about this idea. I was like, “You have one big customer. You should be terrified.”

The one big customer was The New Yorker. That was a great magazine, but it was a paternalism where you were dependent on them. Your self-evaluation was dependent on another person saying, “I like this cartoon.” Something in me very early started to strongly rebel against all of that because my anti-authoritarian and contrarian street came out very strong and said, “I’m not going to live my life this way.” That’s why I started the Cartoon Bank, which was all the cartoons The New Yorker rejected. They bought that back to me, which was a good gig for a while. Eventually, if a big company buys your small company, it’s going to go through the shit and the only question is how long.

I’m more interested in my creative day, which is involved in all of these things, which is all I do is think, work, sleep and interact with my daughter, my wife and stuff. I’ve given into who I am, which is if I don’t stop and the motor doesn’t stop. Other people can talk about relaxation and going on vacations. I was asked by somebody of a magazine or something what my travel tips were and my travel tip was don’t go. Coming down here and talking with someone, engaging in ideas, going up then to Esquire and talking to Jake Field, who’s the editor now about Should You Be Laughing At This? Doing a video conference with CartoonStock, the company we bought in England and Beth and talking to them.

What I have as I approach my 75th year is I have my marbles. I’m still intelligent but I do feel you start to have wisdom about people and how the world is. You quickly assess things in organizations. I have to have this organization in the United States work with this where we’re one company and so much of my mental time is devoted. How do you make different people in different organizations? How do you make it into one company? I get the Harvard Business Review. I tried to read everything I can. I was always amazed when I was in these companies which kept hiring people who had never looked at any research at all.

I find what you’re saying and who you are, inspiring and useful. The notion of work is modeled off of a farm or factory model, which is you work yourself until you’re close to broken down and you retire and you live the easy life. I’ve never chosen the easy path. I’m 25 years younger. I can’t imagine retirement. People use the term workaholic. This idea that you can find purpose, meaning and enjoyment in work. Largely, a lot of people don’t see how that could be the case and for me, it’s nice to see someone who is and does.

INJ 58 | Cartoons
Mind & Cosmos: Why the Materialist Neo-Darwinian Conception of Nature Is Almost Certainly False

It all depends on what you mean by work. If I was packing boxes, that’s one thing. The work requires thought and problems. One of the things I’ve done now because I want to focus so much on the things I’m interested in, I don’t do any of the things I used to like crossword puzzles or anything like that. That is a desire people have for a kind of work. I used to do them. I said, “I’m not that great at it, but I don’t want to spend the time.” Coming in now I said, “I have enthusiasms too and that’s probably annoying to people, but this whole idea of time without outward stimulation where you’re trying to think is probably uncomfortable. I want to try to go into a room and shut off everything. Instead of meditating, getting into a Zen state, the opposite. Start to take one topic with no outside stimulation at all, no pad, no notes, nothing like that and start to think about it and see where it goes.

It’s probably disturbing in a way. I’m thinking, “Have I invented something? Is that cool?” Maybe it’s the opposite of what we think of as meditation, which is clearing your mind. It’s not a monkey mind jumping from one thing. It’s trying to say which is what you’re naturally will do, “Let me take the nub of something and just think.” I was listening to the course on philosophy and about Descartes. How Descartes wouldn’t get up in the morning. He would just lie in bed and think. Maybe that was the seed that planted. It was disturbing for the house cleaners or whatever. What’s happening? He’s thinking. He wasn’t thinking like writing things down. He was thinking. That we do little of now because we’re in this world of incredible entertainment, distraction and disturbance.

There’s always something that you could be doing. With regard to your notion of thinking, the closest thing I’ve done to it is I’ve started journaling, which is using writing to think in a more free way rather than working on a paper.

That might seem extreme. It sounds like, “Where would it go?” If I say, “It’s fifteen minutes,” and I shut off all the lights and everything and I see it. In a way, we’re always doing this. That’s happening naturally, in an unconscious way thoughts are popping up. I want to think about maybe journaling what you’ve said also. One of the things is I have written a book and stuff, but because I’m a good talker, people always ask me, “You should write this. You should do that,” and I don’t. I write some stuff.

That’s part of the reason I launched a podcast because I’ve always felt like I’m a better talker than a writer.

What is journaling? Is it a special journaling program?

To me the thing about writing is it slows your thoughts down because I do it by hand. I’m not editing. I’m writing down ideas. They’re not meant for anything except to have them written down.

I sort of did the same thing with notes. In terms of the companies that I’m running now, I started to feel that email was tedious how people wrote it. I said, “Could you put down the ideas quickly without worrying about sentences?” That is slowing you down. We want to look at the database. We want to do this, we want to do that. Don’t say, “Hi Bob. I hope you’re doing well.” That’s a funny thing. That’s the classic thing, “I hope you’re doing well.” It always makes me feel like, “I might be ill.” If that many people as you get on in years keep writing, “I hope you’re doing well.” Here’s a funny paradox that’s happening. On Google now, they start the sentence completely, it starts doing it. Here’s the paradox. It’s slowing me down. Why? Even if I was originally going to write what they say, I don’t want to write it so now everything is slower than it used to be.

This issue of workaholism, I do think when you’re an outsider and you don’t enjoy or engaged by your work, it’s hard to understand why anyone would. I do think that there are particular professions and skills that lead to it more than others. One is a desire for achievement. You want to make lots of money. You want to build a company. You want to win awards or whatever. That’s one path. The other path is this creative path, this engagement path. What has to be the case is that there has to be a lot of problem solving that goes on. What is neat about that is that is both white collar and blue collar. You can live this engaging work life as you do or I do or entrepreneurs do or artists do. You can find this in a world that can be blue collar. Being a plumber, for example or an electrician or some contractor can also lead to this life and it’s unfortunate that people don’t sometimes pursue that.

[bctt tweet=”AI, in combination with human beings, will be able to create things that neither one know that will happen.” via=”no”]

They don’t value it. There are all different skills. Speaking of an electrician, I had a wonderful electrician come over because I have a Tesla. I wanted the charger wherever moved from one thing to the other. He’s having a problem. He was great because he came with his kid and he had been in the family. He’s the guy who’s probably in his 40s, early 50s. He was saying, “It’s not magic. I’ll figure it out.” He was confident. He had to see where the wires, where they are coming in. It was stuff to figure out. You could see he enjoyed what he did. He enjoyed the craft of it. I do think there is a real disparagement of that. Howard Gardner wrote Five Minds for the Future. This whole world of mechanical expertise of getting things done with physical things, which I am terrible at. The idea of IQ, that’s a narrow kind of ability. It’s the way we test. There are all kinds of intelligences, creative intelligence and athletic intelligence. I have this tremendous admiration for the knowledge to say, “How does this thing work?” People can take things apart and put them together.

The other opportunity is then you can build a business, which is further now a creative endeavor that is interesting. I say this in part because there was a time in my life where I could have headed that way. There’s a weird counterfactual in a sense that would I be some total weirdo contractor? I’m terrible mechanically too, but maybe that’s something that I could have learned.

It’s interesting. We are talking of counterfactual lives and we’re in Chinatown. Chinatown is one of the few neighborhoods that have remained like, “This is an ethnic flavor.” I see the people who are here in Chinatown, their lives are rather restricted in a way. Clearly, these people are smart, have intelligence, creativity. They’re running a fruit stand. When they emigrated from China and took a test somewhere, they’re at Google. You see the counterfactual lives that the Chinese community is living because who’s ever here, it’s the same people from China who are ending up at Google or something like that. One of the things when you get lucky in a way as I did, I always had this motor. That motor might have been not worked out for me the way it has worked out financially or in terms of whatever acclaim I achieved. There was nothing destined. Certain things fell into place at a certain time. The motor helps. The motor gives you a chance. I often meet people who have a lot of talent, who either didn’t have that motor or did want something safe or maybe even had another set of abilities.

They didn’t enjoy the creative work that much. They like other things. There are multiple paths to living a good life. For some people, the work helps pay the mortgage. You’re not going to achieve very much if that’s what you do.

When I look back in my own upbringing, I was an only child. I was spoiled. My parents were a good deal older than me, more than normal. Therefore, I never cared what they thought partly because they weren’t immigrants, but they were the first generation. I didn’t say, “What do my mother and father would think of my jokes? I don’t care.” I did find in my career at The New Yorker with people who would submit cartoons that often people for whom they had always been rewarded in this small town or a place, people had always told them they were great. From the time I was a child, as an only child, I was off in my own world doing this stuff.

When you look at all the environmental things that shape you in terms of your independence, one of the things that I overwhelmingly saw at The New Yorker and even now is that in creative fields, you’ve got to be able to take rejections and not personalize it. Rejection is unpleasant. It’s so much more common than not. The people who would argue with me about the cartoon, I said, “I don’t like this. Do another one.” They weren’t arguing. I can see right away that’s going to be a bad situation. It’s not like I had anything against them. What I’ve often said is that the person on the other side of the desk might not know what they’re doing, but at least give them the benefit that they’re on the other side of the desk and you’re not. They also very well may be wrong about what you’re submitting but that’s life. You’ve got to go on with that too. That is hard for people. They will personalize it. They have grievances and stuff. You can’t be in a creative field and keep creating and get ahead unless you have your own compass.

Folks like you are rare in part because in the same way that people have diverse interests in art, music and food, they have diverse interests in the way they want to live their lives. This life is not for everyone. When it is for you and you can do it well, it can be quite fulfilling. To me, there’s not a wrong or right path, the only thing is finding the path.

In a way fulfilling is wrong. It’s compelling because we have hedonic set points. We have weight set points. My hedonic set point is unhappy and I’m cool with that. I’m happy with that. Most of the time, it’s a psychic disturbance and stuff that is part of my motor. I don’t think contentment is enormously helpful in accomplishing anything. Fortunately, we’re not happiness machines. We’re unhappiness machines. We’re discontentment machines. That’s why we do different things. That’s why we’re dissatisfied like the Louis C.K. bit. I know about people being on airplanes and not being able to get the phone and you are unhappy about that. You can’t believe they charge me for this fake Wi-Fi.

Discontentment can lead to striving in a way that contentment doesn’t. We know that.

My late friend Jack Ziegler who is one of the great cartoonists of all time is a pretty content guy. He would turn out the most fantastic drawings. He was happy to do what he did. Part of my dissatisfaction is it may be like yours. I started that and I didn’t complete it. Even though I now have rationales for this, the legacy and everything, I’ve always felt like, “Whatever happened with that or I can get unhappy with the fact that I said I was going to juggle five balls. I work on it and now I gave it up and now here’s YouTube and here’s a squirrel juggling five balls showing how easy it is.” I find ways to be discontent.

What are you reading, watching or listening to that’s good? What have you been thinking about that’s good?

The book I like is called Mind & Cosmos by Thomas Nagel, a philosopher. It challenges the whole idea of materialism and consciousness. The consciousness is being like if we can’t explain consciousness in a material way, maybe there are many other things. He’s deeply skeptical. He’s a wonderful philosopher. He wrote a seminal paper called, “What is it Like to be a Bat?” We can never know what it’s like to be a bat, but this we do know. It’s like something. I downloaded A Decent Life. When I look at books like this and it says here’s this one idea of this highest morality and on the other hand, they have the idea of complete corruption and immorality? We have to live somewhere in between.

The other thing I liked is The Great Courses, which I download. I’m downloading Great Ideas of Philosophy by Daniel Robinson, who has also done stuff in psychology. Interestingly, this guy is a fantastic lecturer and brilliant, who also supported Donald Trump. It’s fantastic to hear this guy who understands all philosophy, psychology, taught at Oxford and everything and all of a sudden to find out online that he supported Donald Trump. I liked it in a way, not because I like Donald Trump, but this idea. One of the things is I’m not an intellectual snob at all in that. The Great Courses are good courses. He has 35 lectures. Do you want to know about Herodotus? You want to know about Pythagoras and the whole history, there were bigger books on it, but if you could remember what’s in this 25-minute lecture, you would know more than most people in philosophy departments. I do a lot of that stuff.

Bob, I knew this would be spirited. Thanks so much.

Thank you.

Resources mentioned:

About Bob Mankoff

INJ 58 | CartoonsBob Mankoff is the Cartoon and Humor Editor for Esquire and former New Yorker Cartoon Editor. A student of humor and creativity, Bob has devoted his life to discovering just what makes us laugh, and seeks every outlet to do so, from developing The New Yorker’s web presence to integrating it with algorithms and A.I. He kicked off his career by quitting a Ph.D program in experimental psychology at The City University of New York in 1974. Shortly after, he began submitting cartoons to the New Yorker. Three years and over 2,000 cartoons later, he finally made the magazine and has since published over 950 cartoons.


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