Kehinde Wiley on Self-Doubt and How He Made It as a Painter

The artist behind Barack Obama’s presidential portrait talks about developing his skills at a junk store.

Evan Agostini / Invision / AP / Katie Martin / The Atlantic

By age 12, Kehinde Wiley had a reputation in his Los Angeles neighborhood for being a talented artist. Teachers at his school recommended him for a program during which he spent the summer of 1989 in Russia with 50 Soviet kids and 50 other Americans, creating murals, learning the Russian language and culture, hiking, swimming, and picking mushrooms. “It was a strange, magical time,” he recalls.

Wiley went on to study art at the San Francisco Art Institute and Yale. He now has a studio in Brooklyn, and Barack Obama chose him to paint a lively portrait of the former president that now hangs in the National Portrait Gallery.

I recently spoke with Wiley about traveling to Nigeria to meet his father for the first time after having painted portraits of him for years, dealing with criticism, and the importance of slowing down. This interview has been lightly edited and condensed for length and clarity.

Lola Fadulu: What was your mom’s work schedule like?

Kehinde Wiley: My mother, while raising six kids, had a number of small-business activities. The most prominent one in my memory was sort of like a junk store.

She would be away, in the earliest years, much of the day. Then she would be around more in the late afternoons, evenings. When we weren’t in school, we would be around the shop, and I remember learning Spanish dealing with a lot of the customers there.

Fadulu: Aside from learning Spanish, was there anything else you learned from those times you helped out in the store?

Wiley: I think I learned a sense of making something out of nothing, trying to dust off old items and seeing some level of value in them, recognizing that no one is going to help you.

Fadulu: Did your mom have any particular field or industry that she wanted you or your siblings to go into?

Wiley: Well, I remember as kids, we all had different passions, and she encouraged all of them. My twin brother and I would be going to art school as kids because there was a free program that allowed us to get off of the streets of South Central Los Angeles and spend our weekends studying art.

I remember my mother wanting me to go into preaching. She was taken by the fact that I was quite successful at some oratory competitions. She was going through a particularly religious fervor at that point in her life, and she encouraged me in that direction.

Fadulu: At that point, were you thinking about turning art into a career, or was it more of a hobby?

Wiley: In the beginning, it was much more of a hobby, and much more about just having an outlet for creative energy. Only later did it start to have real personal consequence.

Fadulu: When did that start to change?

Wiley: I was 12 years old. Russia was one of those programs that was a free program. It was an opportunity for me and 50 other American kids to go off into what was then the Soviet Union, and to study art in the forest outside of what was then called Leningrad, and is currently called Saint Petersburg.

We created a series of murals, and we had language classes and cultural exchange. And we would hike off into the forest, pick mushrooms, and swim. It was a strange, magical time. It allowed my sense of what was possible to blossom, at that very important age.

Fadulu: Did you know that you were a good artist when you were 12?

Wiley: Of course. That was my one bit of power in the world. That was the thing that got me positive attention, as opposed to so much negative attention that was coming at so many of my classmates at the time.

Fadulu: Would you consider helping your mom out in the store your first job?

Wiley: It was definitely my first job. I remember thinking about all of those bags and bags of clothes, and trying to figure out how to sort out different colors, and different types of fabrics, and how to organize things in terms of style and age. I remember looking at things that to me seemed like junk, but with a little bit of TLC, a coat of paint or something, is repositioned as something that people are willing to spend good money on.

That was my first job as a kid, but it wasn’t really positioned as a job, because it was just what you do. You lend a hand.

Fadulu: So, what was the first job you had that was positioned as a job?

Wiley: I think my first real job was actually going to work for the art school that I used to go to as a kid. While I was once an 11-year-old student at the Los Angeles County High School for the Arts’ Summer Arts Conservatory, which was housed on the campus of Cal State Los Angeles, I was later as a high-school student recruited, at first, as a teacher’s assistant, and then later as a teacher to teach drawing and painting to youngsters. I was 17 and 18, teaching 9- and 10-year-olds how to paint.

Fadulu: Is that when you were beginning to think about a career in art?

Wiley: My first thought was that no one makes it as a painter. I was just looking around at the landscape of contemporary art, which was pretty dry in Southern California during the ’90s. There was no modeling for success when it came to a job in the arts.

So I thought that my best option would probably be in arts education. So when I went to do my bachelor’s degree in fine arts at the San Francisco Art Institute immediately after high school, I assumed that I would probably study art and become an art teacher. While I enjoyed it very much as a high-school student, I didn’t really have a burning desire to be a teacher. I just knew that that would enable me to support my art habit.

Saul Loeb / Getty

Four years of arts education in San Francisco, then going off to graduate school on the East Coast at Yale, opened up a whole new set of possibilities. And perhaps for the first time I started to glimpse what it might mean to launch a successful career as a painter.

Fadulu: And where did you catch those glimpses of those other possibilities? I know you said you were at Yale, but what exactly were you seeing?

Wiley: What happens there is that while I’m painting in the graduate art studios, I’m also taking trips into the city with my classes, and having conversations with artists in their studios. I remember having classroom trips to art galleries and seeing actual exhibitions I was excited about. Being in the class with professors who are working artists, the light slowly started to turn on, and that sense of imagining myself as one of those people.

But still, there’s a lot of self-doubt, and there was also a really tough regime of criticism that arts education put me through, which enabled me to develop a really thick skin, but also caused me to doubt whether or not I had the chops to make it as a professional artist.

Fadulu: How did you deal with the self-doubt?

Wiley: I think a lot of it was being able to recognize the relative nature of a lot of the arguments that were being made in large classrooms. One art object could give rise to five different arguments, and depending on who was the most convincing, the success or failure of that art object would announce itself. It became increasingly obvious that it had very little to do with the art, and more to do with the environment in which the art was being consumed.

I had a strong sense that this school was an immense place to learn new ideas and histories, but also a potentially toxic place in which you can get caught up within the incredibly specific politics that each school gives rise to, and lose track of the broader target.

Fadulu: And didn’t you go to Nigeria to reconnect with your dad?

Wiley: Well, I connected, period. My father and mother broke up before I was born. He returns to Nigeria, and I’m never to see him until I’m 19. So, 1997,  I just decide on a whim that I’m going to go find him. A lot of it was a lot of buildup, emotional buildup. This constant desire to see who your father is, and just to know that connection. I think on another level it was about pushing myself, and knowing what I’m made of, whether or not I’m capable of pulling something like this off. There was a lot of teenage bravado going on there.

There was this incredible curiosity as a portrait painter, just—what does he look like? I began going to different universities asking if they knew who this guy was. I knew that he studied architecture in America.

So I would go to universities and go to their architecture departments and ask if anyone knew my father, and that didn’t work. Someone finally said that I should go, based on his last name, to southwestern Nigeria, where I then went to the University of Calabar. And his name was on the door of the department. He was the head of the architecture department. And nothing’s been the same since. There was a series of paintings that I did shortly after meeting him for the first time, where I was just obsessed with painting him, getting that out.

Fadulu: Was that trip what you thought it would be?

Wiley: No, not at all. I had this illusion that there would be arms wide open, and music would be playing, and that I would quickly and quite easily recognize this lost side of my African ancestry. And in fact, it was an incredibly difficult and exhausting process to find him. And by the time we did find each other, there was that strange moment of trying to figure out what each other and who each other was. What were my intentions as I showed up? What were my feelings toward him? It was incredibly complicated.

I think I was a bit naïve to think that all of those emotions would just simply be resolved by seeing him. In fact, it became much more difficult to come to terms with the feelings of resentment and abandonment than I had anticipated.

Fadulu: You said you became obsessed with painting portraits of him.

Wiley: There were a number of those that, to this day, I can’t find, because I sold off so much work as an undergrad. One of these days, I have to track this stuff down.

Fadulu: What was going through your mind when you heard from Obama about his portrait?

Wiley: Well, there was never really any point where I had the job. I heard they were considering a number of artists for this, and I was welcomed to be interviewed as they were down to a smaller group. But there was never any point where I just knew, until I knew. Back in 2016 even, I was in the Oval Office, incredibly nervous. And I was interviewing with the president about this potential job, still not knowing what it was going to be, but just feeling incredibly grateful for having been invited to have the conversation.

So every step along the way, it just became more and more real, and more and more possible.

Fadulu: So what was the interview like?

Wiley: Of course the president wanted to know what it is that I would bring to the picture. I spoke really honestly about what excited me about him and me being involved in this historical moment: the sense in which we both share that story of having African fathers and American mothers. That sort of journey to find the father, that yearning to try and create some sort of internationalist presence in our work.

I spoke about the possibilities, allegorically, of telling his story in a painting. And so what you end up with in that painting are some amazing botanicals that are visually captivating, but they also nod toward certain flowers that are prominent in Indonesia, certain leaves that are prominent in Hawaii, the state flower of Illinois, the flowers that are most commonly seen in the grasslands of Kenya.

All of those strange, forest-like spaces are behind him and pushing up and forward. Those were the things that I was discussing as a possibility, and I think that it must’ve set something right.

Fadulu: You said it became more real as you went through the process. Were you working at all on it before it was official?

Wiley: Oh, God, yeah. I had gone to photograph him, and that wasn’t quite right, so I went back and I photographed him again. There were months of just trying to figure out how to artificially create this type of image on the computer and approximate what it would look like, and then start doing studies and see what it looks like in the actual paint. It was a long time coming. But in the end, it was all worth it.

Fadulu: Those months of trying to figure out how to create it—were there any big lessons from that?

Wiley: Just slow down. The more important the portrait, the more nuance the likeness has to have, the slower you have to get. So I had to get smaller brushes, really concentrate on just doing small passages per day, rather than trying to do broad strokes. And so it was a very different type of painting. You can feel it, almost, when you look at that painting, it's a much more contemplative piece. But I got very familiar with his face.

Fadulu: How did you feel about its reception?

Wiley: Well, he told me, “This is what I do, I’m used to the national spotlight, the global spotlight, but you’re new to this, so get ready. It’s gonna be a big deal.” And boy, was it ever.

I’ve never seen a work of art go viral that way and become a global sensation. And, of course, you’re dealing with the culture wars, and powers and principalities, and the Republicans and the Democrats. It did come as a shock to see that people would get so excited as to start sending death notices and threatening letters and all of this.

It’s surprising, but when seen in the proper context, when seen as a type of cultural signpost, when that painting is seen as what it is, which is a moment of celebration for him and his high-water mark within our culture, then you recognize it’s bigger than you are.