From Leonardo da Vinci to Steve Jobs: The Benefits of Being a Misfit

Walter Isaacson is a gifted storyteller. A career journalist who has steered both Time magazine and CNN, Isaacson has written biographies of Benjamin Franklin, Henry Kissinger, Steve Jobs and Albert Einstein. His latest biography, published last year, looks at the life of Leonardo da Vinci. Isaacson, now a history professor at Tulane University, recently visited Wharton to be interviewed by his friend and management professor Adam Grant as part of the Authors@Wharton speakers series. Grant has also written several bestsellers, including Give and Take and Option B, which he co-authored with Facebook COO Sheryl Sandberg.

Grant and Isaacson shared a lively discussion on topics ranging from the genius of Jobs and da Vinci, the qualities of a curious mind and what it takes to be a great leader. The following is an edited transcript of the conversation.

Adam Grant: Walter, it’s such a treat to have you back here.

Walter Isaacson: It’s great to be back at Penn and back with you. We’ve had a lot of good times together.

Grant: I want to talk about so many fascinating people you’ve written about, but also a little bit about your own life. You’ve run the Aspen Institute (a nonpartisan educational and policy studies think tank), had leadership roles at CNN, and were the editor at Time. You’ve also been the biographer of some of the greatest innovators in human history. Your new book is Leonardo da Vinci. How do you write a biography of someone who lived half a millennium ago?

Isaacson: The good thing about Leonardo da Vinci is he left 7,200 pages of notebooks. We can look every day at this mind dancing across nature.

We all keep notes digitally these days. When I tried to do Steve Jobs’ period in the 1990s — when he was in the wilderness between his stints at Apple, he worked at NeXT Computer — we went back to try to get all the emails and memos. He couldn’t get them out of his machine. The operating system couldn’t retrieve them anymore. But paper is a really good technology for the storage of information.

I asked Simon & Schuster, the publisher who did Leonardo da Vinci, to “do it all on art paper and not one of these things where you put the things in the center.” I want it throughout to be that heavy quality, coated, color images because I wanted to show that paper is actually sometimes good for transmitting information.

Grant: You’ve picked a lot of original thinkers throughout history. Why da Vinci?

Isaacson: You’ve written a lot about innovation and creative leadership, and you’ve seen the patterns. It takes me a while to see the patterns. I started with Ben Franklin, then Einstein, then Steve Jobs. The pattern after a while wasn’t that they were smart, because if you’re at Penn, you’ve met lots of smart people, and they don’t usually amount to much. They’re a dime a dozen. But what’s interesting is when they’re innovative or creative, as in your books, the pattern is people like that tend to be curious across disciplines.

“The biggest takeaway from this book is just stay curious about everything.”

Penn is a university that pioneered crossing disciplines, as opposed to other Ivy League schools that really do have departments and disciplines that are much more siloed. Ben Franklin did that. He goes up and down the coast, looking at how swirls of air resemble the swirls of the northeastern storms. Then he discovers the Gulf Stream. Same with Leonardo. He sees patterns across nature.

When I was writing about Steve Jobs, he would end his product presentations always with the intersection of the arts and technology. He said, “At that intersection is where creativity happens.” He said to me, “Leonardo is the ultimate of that.” Leonardo had that ability not just to connect art and science but to make no distinction between the beauty of art and science. That’s why he was the final mountain to climb in this series of books.

Grant: I think your point about pattern recognition is really important. To me, studies of creative people are about looking at lots of people’s experiences at once, as opposed to doing one person’s experience in a lot of depth. I think there’s a ton we can learn from da Vinci. I also think it seems like it’s unfair. I want to live in da Vinci’s era because no one knew anything. You be an architect and a scientist and a great painter, and you could get to excellence much quicker in each of those fields than you can today. Is it too late for a Renaissance man or woman today?

Isaacson: You’re right. At age 12, he goes to Florence and suddenly people aren’t in one discipline. It’s not as if he worked for [Italian painter] Andrea del Verrocchio in one of the workshops there and people said, “that was an art studio he worked for.” No, it did everything. Leonardo at age 12 solders a copper ball and does the engineering to put it on top of [designer and architect Filippo] Brunelleschi’s dome. You have Brunelleschi and [architect Leon Battista] Alberti doing perspective, but they’re connecting to art. Leonardo is connecting as a 12-year-old to engineering.

Grant: I feel like I was a loser 12-year-old now. Thanks a lot.

Isaacson: Do you want to know how good he looked when he was 12? There is a statue of David that Verrocchio did. And if you look at one of the notebooks of somebody else in the shop, there in the middle is Leonardo at age probably 12 or 13, posing for that statue.

He was a misfit. Steve Jobs talked about how he was among the misfits, the rebels, the round pegs in the square holes, those who think differently. Leonardo was illegitimate, which was lucky for him. Being born out of wedlock, he didn’t have to be a notary like his father and grandfather and great-grandfather. He was gay. He was left-handed. He was vegetarian. He was heretical. And he was beloved in the town of Florence. They accepted that and assumed, like Leonardo did, that you could learn everything you wanted about anything you wanted. We could still be a little bit more like that. We silo ourselves too much. We specialize too much. The biggest takeaway from this book is just stay curious about everything.

Leonardo makes a list every day of what he wants to learn. “Why is the sky blue?” It’s the things you and I asked when we were 10, but we outgrow our wonder years. “Why do fish swim faster in water than birds fly in air when water is heavier?” And my favorite: “Describe the tongue of the woodpecker.” Who wakes up one morning and says, “I’ve got to know what the tongue of a woodpecker looks like?” How would you even find out? Get a woodpecker? Yet he’s Leonardo. It’s not because he needs it to do his studies of the flight of birds. It’s not because he needs it to paint a painting. He needs it because he’s Leonardo, and he just wants to know everything you can possibly know about everything that could be known.

“Let your imagination push you a little bit. Don’t be afraid of daydreaming and then trying the impossible.”

When Bill Gates was trying to talk me into this book, he said Leonardo was the last person in history who aspired to know everything there was to know about everything that was knowable. I am not sure that’s totally true. Ben Franklin aspired to do that. You and I can aspire to do that with Wikipedia and the internet and any rabbit hole you want to go down. Just staying curious is the main lesson.

Grant: How did he decide what to be curious about? It seems like he was interested in everything but went deeper on some subjects than others.

Isaacson: Yes and no. Anything that came into his field of vision, he got curious about. He decided, “all right, I want to do flying machines.” Then he does studies of the flights of birds. He starts his anatomical drawings because he wants to paint “Saint Jerome in the Wilderness,” and he can’t quite get the neck muscles right. But after a while, he’s not just dissecting neck muscles, he’s dissecting the heart, the liver; he just drills down.

Grant: He’s accomplishing all of these things that we remember him for so many years later, yet he was frustrated during a lot of this experience. What was it like to be da Vinci?

Isaacson: The good thing about his notebooks is we can see, first of all, that he’s human. He makes math mistakes, leaves things unfinished, comes up with crossbows that could never fire or tanks that could never roll or rivers that weren’t diverted. For a while, I was thinking, “OK, he’s pretty flawed. He doesn’t finish his things.” But then I realized he’s just pretty human. He just holds onto things until he can perfect them. And he despairs. Later in life, he draws his craggy warrior and his boyfriend Salai when he’s doodling. But he also just writes this line over and over in his notebook, “tell me, tell me, did I ever accomplish anything? Tell me, tell me, did I ever get anything done?” You realize he also despaired.

Grant: What else did you find, beyond the importance of being curious, that’s relevant to us today?

Isaacson: I like the fact that imagination and fantasy played such a big role. I’m walking in the Philadelphia airport and some 10-year-old kid is asking his father, “Why is that shirt this way? What’s this?” Finally, the father says what every father says at a certain point, which is “shut up, and quit asking so many stupid questions.” By age 15, this kid shuts up and quits asking questions. Also, it’s, “quit daydreaming.” But Leonardo always daydreamed.

One of the things I learned from his notebook is that one of the main things he did in life was theatrical pageants and plays. When he’s in his 20s, his main job is costumes for the big pageants and plays that the Medici family are putting on. Everybody says, “didn’t he invent the helicopter?” Because everybody knows this drawing. Well, that was originally done in his notebook to bring the angels down from the rafters in a performance of a particular play. But he always allows his imagination to blur into a challenge in reality, so he goes on to try to design flying machines. Let your imagination push you a little bit. Don’t be afraid of daydreaming and then trying the impossible.

Grant: You’ve mentioned Steve Jobs, and it sounds like he was one of the reasons you wrote this book. I guess when Steve Jobs tells you to write a book, you have to do it. But that was a totally different process than writing about Steve. For the Jobs book, you spent many, many hours with him and people who knew him well. What was that experience like?

Isaacson: Steve Jobs was a deeply spiritual, very intense person who had rough edges and was nasty at times, and mean. But [Jobs] having driven people crazy, they’d also walk through walls for him. He’d drive them to do things that they didn’t know they could do. How do you get that intense personality? I sometimes spent days on end either staying at his home or nearby, subject to watching him have that very mercurial, as he put it, personality. And it was difficult, especially when it was clear he wasn’t going to beat the cancer.

He was angry at times, on painkillers at times, and saying things at times about people I knew were his friends or very close to him. That presented a journalistic dilemma. Because all my life, I was always trying to get people to say things that then would be kind of explosive and exciting. There was a lot I ended up leaving out of the book where I thought, “OK, he’s just said some really mean things.” I had to balance how enlightening that will be for the reader versus how hurtful that will be for the people he’s talking about. Also, I’m not sure he really meant it. There was an anger and a painfulness near the end of his life. That was a hell of a lot more intense than if it had been Ben Franklin or Leonardo.

Grant: We both know a fair number of entrepreneurs who have held Jobs up as their role model and said, “look, he wasn’t the nicest guy in the world. That’s proof that this is sometimes how you have to be.” Did he succeed in spite of his cruelty or because of it?

“Who you are is a narrative that accumulates.”

Isaacson: I’m going to turn this one back on you, too. But I’ll start with my answer. When I started working on Steve Jobs, (Apple co-founder Steve) Wozniak said to me, “the main question you have to answer is, did he have to be so mean?” Then I talked to Andy Hertzfeld, one of the original 20 kids on the Mac team. Andy said, “You’ve just got to ask him, did he have to be this cruel?” Over and over again, I think I quote a lot of people as saying that. At the end of the book, I quoted Woz, who said, “Well, if I had run Apple, I would have been much nicer. [We] would have been more like a family. I would have made sure we all had stock options. I would have not yelled at people as much.” Then Woz paused and said, “And if I’d run Apple, we probably wouldn’t have done the Macintosh.”

Each person gets to answer by the end of the book, “did he have to be so mean?” Most of them would say, “he didn’t have to be this mean, but I ended up wanting to walk through a wall for him.” When I asked Steve at the end of the book, “did you have to be so mean? Did you have to be so cruel to people?” He said to me, “you East Coast polite types always speak as if you have velvet gloves on, and you always sugarcoat your words. When people do something that sucks, I have to tell them it sucks because I’m just a middle-class kid trying to make sure I don’t have b-players on my team. I can’t afford to be as gentle and as nice.”

I guess my answer in retrospect is, no. You don’t have to be that mean. You don’t have to be cruel to people. You have to be tough, and you have to be intellectually honest, which sometimes I have trouble doing. I look at a lot of great bosses you’ve written about and they’re intellectually rigorous, but they’re basically nicer.

What’s your answer, Adam?

Grant: You were asked at some point, “what’s the one piece of advice that you would have given to Jobs?” And you said, “he could have been kinder.” That resonated a lot for me. I never met him, but I’ve talked to a lot of people who worked closely with him, and very consistently they say, “look, a great boss is just like a great parent.” As our own (Penn psychology professor) Angela Duckworth would describe it, “they’re both demanding and supportive.” He left out the supportive a lot, and sometimes he took the demanding way too far. I think what’s kind of interesting about it is it seems like he evolved over the course of his career. You talked about this in the book. I always wonder, if he had been kinder to other people, would he have been kicked out of his own company?

Isaacson: Well, no. The original Mac comes out in 1984 with a wonderful 1984 ad, and then by 1985 he’s out, partly because he’s too much of a perfectionist. He had held up shipping the original Macintosh because he looks at the circuit board inside and tells the engineers it’s ugly. They say, “Steve, it’s in a sealed case. Nobody’s going to see it. Nobody’s going to know.” And he says, “Yes, but you will know. You’ve made it something that sucked, and you’re going to know that.”

They hold up shipping the Mac until they make the circuit board inside beautiful. Now, that is not something you should teach at Wharton. At the end, when they get it right, he tells all 30 engineers on the Mac team to sign a whiteboard, and he adds his signature, steven p. jobs, in lowercase. They engrave it on the inside of the Mac, and he says, “Real artists sign their work.”

“The people who are the most innovative and successful realize that you have to put together a team of people with different styles and different talents.”

Take Leonardo’s painting “[Saint] Jerome in the Wilderness.” He just wouldn’t ship it until it got finished, and 25 years later, he’s doing those anatomy drawings and trying to perfect the neck. When you get to the greatest painting of all time — [the Mona Lisa, who was] the wife of a cloth merchant in Florence — the cloth merchant never gets the picture of his wife because Leonardo keeps it for 16 years, putting 200 or 300 tiny glazed brushstrokes to get the lips right. He carries it with him to France and everywhere else. Sometimes you have to let the perfect be the enemy of the good. When Steve Jobs comes back in the late 1990s, they give him a little sign that says, “Real artists ship,” which means sometimes you get the damned product out the door. He learned to do that by 1999.

Grant: I’m curious about the evolution between the old Jobs and the new Jobs. Did he change?

Isaacson: Yes and no. There are two times when you think he’s going to change. One, when he comes back to Apple after having been fired. Two, when he comes back from having had a liver transplant and knowing the cancer has spread. In both cases, you’re thinking he’s now going to be kinder and gentler. He is a bit, but then he’s still Steve.

I think I have this scene in the book where they all come out to meet him at the private airport when he comes back from his liver transplant, and by the next day, he’s berating everybody for having screwed things up in his absence. He doesn’t fully change, but his spirituality and his feel for other people definitely deepens, and his brutal honesty is at least channeled for a purpose. It’s also balanced by acts of extraordinary kindness and inspiration, where he just really does kind things for people. That kind of surprised them, because he would have berated them the day before. He becomes more complex, but not just more simply kind.

Grant: How do you reconcile the acts of cruelty with the acts of kindness?

Isaacson: That’s why one writes biographies. That’s why my biographies tend to be a bit long, because there are complicated things. I always begin my biographies in a very simple way, which is where the person is born. In the end, the person dies. Every year we grow and things happen. Who you are is a narrative that accumulates. He had a very complicated early life in which he was, like Leonardo, born out of wedlock. Unlike Leonardo, he was put up for adoption and was craving the affection of both [parents]. He eventually finds out who his birth father and mother are. But I don’t try to psychoanalyze him. I just try to show, in growing up, that passion for perfection, that unwillingness to compromise on perfection causes him to feel, almost in a Nietzschean fashion, a bit like the Superman who is not bound by the usual laws of politeness or even of nature.

Grant: I think it’s encouraging to read about these different people and say, “Maybe I’m not like Jobs, but I can see some of my qualities in other great innovators.” What are some of the starkest differences you’ve seen in how they work?

Isaacson: Innovators, creative people, tend to be very different, and the people who are the most innovative and successful realize that you have to put together a team of people with different styles and different talents. Ben Franklin’s greatest contribution as a founder was not being the smartest founder, because you had Jefferson, Madison, all these; not being the most passionate, because you’ve got John Adams and his cousin, Samuel Adams; or even being a man of great gravitas, like George Washington. It’s that he knew how to put together a team.

When I asked Steve Jobs when he was dying, “What was your best product?” I thought he’d say the Mac or the iPhone. He said, “No, making a Mac or an iPhone is hard, but making a team that will always turn out Macs and iPhones, that’s the hard part.” That’s the main thing I think you should learn at a place like Wharton or in life, which is you’re not going to play every position. How do you get a team around you that innovates?

Grant: What’s the worst piece of career advice you’ve ever been given?

Isaacson: “Go to CNN.” I worked for Time Warner, and I was a journalist, and I loved the printed word. I loved deep reporting. After a while, Time Warner also owned CNN.

“The piece of career advice I’d give, which is the opposite of what I got, is know your strengths and go with your passions.”

I said, “well, I’m not good at TV. It’s not something I know very well.” The bosses I had said, “oh, yeah, but you can learn it. You can get the team, you can master it, and it’s a big enterprise. You know how to manage.” But I did not know myself well enough.

One of the things that made me OK as a leader at Time is I knew how to put together that magazine as well as anybody there. If somebody said, “we can’t put that picture in because it would crop badly,” I’d say, “no, just crop it from the left side, put it through the gutter, and bleed it on the right.” Or I had reported on a Henry Kissinger or a Madeleine Albright, so I knew reporting. When I got to CNN, I didn’t know how to make TV. I’d say, “well, why don’t we have [international correspondent] Christiane [Amanpour] in Baghdad doing something like this?” And they’d say, “Oh, no, we need a donut around a satellite that has to be done with the film.” And I had no idea what they were talking about.

I guess the piece of career advice I’d give, which was the opposite of what I got, is know your strengths and go with your passions to do things. And if you feel like you’re going to be pushed to do something that you don’t particularly like or know or understand, just say no.

I discovered I wasn’t very good at understanding the intricacies of television. Secondly, I didn’t like to deal with big egos in television. I’m on the other extreme on the kindness spectrum. There are all these big egos who just love having that red light go on, and they want to anchor the President’s press conference. They’re all being big ego-like, I was trying to please everybody, and I was a bad manager. I decided, “OK, I don’t manage big enterprises of high-ego people well. I don’t know television well. I will do things like be in print, and be in a think tank like the Aspen Institute, and not go try to do things that I’m not suited for.”

Grant: One of the most interesting things you’ve been doing at the Aspen Institute has been trying to re-imagine the future of innovation and education. You’ve just reinforced through the da Vinci book that we need to put the “A” in STEM, that the arts are often missing from technical education. How can universities do a better job of integrating disciplines?

Isaacson: I hear people being told they’ve got to learn coding. No, our machines are going to be able to code for us. If there’s anything artificial intelligence will do, it will have more object-oriented coding so that you don’t have to do it. You need to know how coding works. You need to know what an algorithm is. You need to know what a logical sequence is, and what the language of coding is. But just being a coder is not going to help.

It helped you in the 1970s when the engineers were leading the revolution. But now the revolution is about connecting life sciences and medicine to technology. It’s about connecting energy, music, creativity and art. It’s being like Steve Jobs, who never could code very well. Bill Gates could certainly code extremely well, but when they both do a music player, Bill produces the Zune and Steve produces the iPod. It’s because Steve had a feel for the humanities, what people are going to be desiring for the arts, for beauty. He knew that beauty mattered. I think that if you just go barreling down the path of needing to know coding better than anybody, you’re not going to have the creative connections that will make you an innovator.

Grant: Now I have some submitted questions for you. Here’s the first: If da Vinci were a college student today, what would he study?

Isaacson: Obviously, he would be cross-disciplinary. When people ask me, having studied Leonardo da Vinci, “what should I major in?” I always say do a dual major, and make it like music and physics, Spanish literature and applied math. Try to show that you can cross disciplines.

Grant: What would da Vinci think of the biography that you wrote?

Isaacson: I don’t know. It’s hard because he was not somebody deeply personal. In his notebooks, we have sketches of his boyfriend. We have other things, but not a whole lot of personal stuff. I think he would have been puzzled by the contemporary desire to know the personal, as opposed to just the work. Biographies didn’t quite exist back then, but Giorgio Vasari, who was a contemporary, did some lives of painters-type essays. They’re very non-personal. I think it’s something that’s only in modernity that we feel the personal connects to the profession in the art.

“I don’t think you have to master every subject, but I think you have to appreciate the beauty of it.”

Grant: What about the challenge of encouraging people to become polymaths? How we can build that in companies and universities?

Isaacson: I don’t think you have to master every subject, but I think you have to appreciate the beauty of it. When Einstein is doing General Relativity and having trouble with tensor calculus, he takes out his violin and plays Mozart. He actually loves music and plays pretty well. He says, “that connects me to the harmonies of the spheres.” It helps inspire him to understand the beauty of waves and motion and things like that.

I come from the humanities background. I love engineering. I love math. My dad was an engineer, so that’s why I wrote about it some. But the reason I started writing about it is that I realized that we of humanities backgrounds always are doing the lecture, like, “oh, we need to put the A in STEM. You’ve got to learn the arts and the humanities.” You get big applause at places when you talk about the importance of that.

But we in the humanities, or in business or in finance and everything else, also have to meet halfway and learn the beauty of math. People tell me, “oh, I can’t believe somebody doesn’t know the difference between Mozart and Haydn, or [King] Lear and Macbeth.” And I say, “Yes, but do you the difference between a resistor and a transistor? Do you know the difference between an integral and a differential equation?” They go, “oh, no. I don’t do math. I don’t do science.” You know what? An integral equation is just as beautiful as a brushstroke on the “Mona Lisa.” You’ve got to learn that they’re all beautiful.

Grant: Which biography has changed you the most?

Isaacson: Leonardo. Every day I think of things that are so mundane but that Leonardo was curious about. Why do the ripples move differently than the wind on the face of the water? Ben Franklin asked that as well. As a kid, we probably asked that. But I now pause to look at the ripples and how the light hits the ripples and how they create luster.

Grant: There are multiple questions on how you get to know the details of people’s lives. Do you have favorite ways of starting an inquiry to really understand someone?

Isaacson: One thing I feel as a biographer is that for a guy, if you’re writing — from Steve Jobs, Ben Franklin, Einstein, Leonardo — it’s often all about dad. If you look at memoirs from Bill Clinton to Barack Obama to Richard Nixon, they talk about their fathers. Steve Jobs keeps talking about the influence of his adoptive father. Einstein’s father goes bankrupt trying to do the electricity for certain cities. Leonardo is living up to his father because Leonardo is illegitimate, and his father never makes him an heir. I could give a hundred examples, but it begins with the relationship to parents.

Grant: When you think about the different innovators that you’ve profiled, how did they define success?

Isaacson: They were not after money. Steve Jobs could have made a lot more money at Apple. He was always trying to make the product better. Remember the new Mac that came out in 2000? It’s sort of that beautiful, curved thing, and it’s in a few colors. It’s slightly translucent, and there’s a handle on it. They said, “well, this is a desktop machine. We don’t need the handle. People aren’t really supposed to move it around. A handle will cost another $60.” Jobs said, “No, the handle is there because it makes the machine approachable. My mom is afraid of her computer. But if there’s a little thing she can put her hand in, she can touch it and knows it won’t break. It makes her connect emotionally to the computer better.” That was right, but it cost money, so the Mac didn’t make as much.

Likewise, Leonardo doesn’t deliver the “Mona Lisa” to the cloth merchant, doesn’t deliver “Adoration of the Magi” to the church. He’s doing it and keeping it. Whether you’re on the board of directors of an airline or starting a company, sometimes you have to say, “we can’t have our lodestar be return on investments, profits and relative margins. Those are our only lodestars.” A lodestar has to be, are we making a product people will always love? [Amazon founder] Jeff Bezos does that. Steve Jobs did it. Leonardo did it.

Grant: What’s next for you?

Isaacson: I don’t think I’m going to try to do another big biography. I’ll probably do a book about the 1890s in New Orleans, a woman named Lulu White, who was Creole. She opened Mahogany Hall, which was the best music and sporting house in Storyville, the red light district. She hires Jelly Roll Morton to be a pianist, and then young Louis Armstrong comes and plays.

But what happens is crossing the color line is very important back then in New Orleans with the Creole society. One of her friends, Homer Plessy, goes down to Frenchmen Street and boards the train. They ask him to sit in the colored car. He refuses, and that becomes Plessy v. Ferguson, and they have to start drawing the color line after that. America did not need to draw a color line, especially in places like New Orleans, where it was very variable. I want to do something about race, class, sex and all that jazz.

Grant: In closing, for an audience of students aspiring to be more creative, more innovative, are there any other tips that you would offer or myths to bust?

Isaacson: I’ll just tell you something small. The tongue of the woodpecker is three times longer than the beak. And when the woodpecker hits the bark at 10 times the force that would kill a human, the tongue wraps around the brain and cushions it, so the woodpecker can do woodpecking.

There’s absolutely no reason you need to know that. It is totally useless information, just as it was totally useless to Leonardo. But just like Leonardo, every now and then, it’s good to just know something for pure curiosity’s sake.