Design Matters with AMY SHERALD

Published on 2018-06-26

Hello my dear Drip friends! This is the last official episode of my 13th season of Design Matters! And it is a special one; my guest is Amy Sherald, the extraordinary artist who painted the official luminous portrait of FLOTUS Michelle Obama (image above). This summer I will be posting some additional live episodes here on Drip and they include live interviews I conducted over the year with artists and designers including Laurie Anderson, Matthew Carter, Chase Jarvis and more. I want to thank you for all of your support this year. It's been a thrilling journey and I am so so so grateful for your kindness and generosity. I couldn't do this without you!


When writing about artist Amy Sherald, it’s tempting to start with a story—the story. The one that, narratively, is an ideal way to launch into an article or essay. It provides a hook, a dramatic doorway into a discussion of her life—

But the story, while an incredible one, does not fully define her. And the notion of identity has been at the fore of Sherald’s life and work since the beginning. 

Growing up the daughter of a dentist in a middle-class family in Columbus, GA, Sherald has said that she was always expected to behave in a certain manner, dress a certain way—especially when she was in white company. And she was in white company often: Sherald attended a private school with only a few black classmates, and she has said that she didn’t have black friends until high school. As Dr. Arturo Lindsay wonders in the 2011 catalogue to the show The Magical Real-ism of Amy Sherald, “If she had to ‘act’ appropriately among blacks and ‘perform’ at an even higher level for whites, then who was Amy Sherald—really?”

It’s a question Sherald would go on to explore in her early work. But first she had to discover her talent in an absence of art. As a kid, landscapes from furniture stores hung above her family’s fireplace. Her father told her that the “Civil Rights Movement was not about you being an artist”—no doubt jarring words for the young girl with a predilection for drawing people who caught her eye in magazines, a seedling of her future process as a portrait artist.

Still, her parents paid for art classes. And on a sixth grade field trip, she had a bit of a catharsis when viewing the large-scale contemporary piece “Object Permanence” by Bo Bartlett—and not just because it was the first painting she had ever seen in real life. It depicted a black man standing in front of a house. 

“Seeing that painting of a man that looked like he could be my father stopped me dead in my tracks,” she has written. “This was my first time seeing real paintings that weren’t in a book and also weren’t painted in another century. I didn’t realize that none of them had me in them until I saw that painting of Bo’s. I knew I wanted to be an artist already, but seeing that painting made me realize that I could.”

First there was a minor detour: At Clark-Atlanta University, she pursued a pre-med degree, likely to the approving nods of her family. But after an artist reminded her in her junior year that not using her talent would likely result in her losing it, she switched majors to her passion. A deep dive into her craft followed. She traveled twice to Portobelo, Panama, on an international art program. She moved to Baltimore and pursued her MFA at MICA, where she decided to focus exclusively on people of color. She painted. And her signature style began to take root: She depicts her subjects’ skin in a grey that results from the marriage of black and Naples yellow, which she first tried after a friend suggested it as a step in an easier way to paint flesh. But Sherald liked the way it came out, so she stopped at that stage of the skin tone development and framed her subject against vibrant hues. As gallerist Hauser & Wirth writes, “The skin is rendered in grayscale, which refers to not only black-and-white photography—Sherald paints from photographs—but also the artist’s intention to ‘remove color from race,’ shifting the conversation toward the humanity and individuality of each figure.”

But then her career momentum ground to a halt. And the reason is the hook of many pieces about Sherald, which begin by documenting her health, and that of her family members. Throughout her life, Sherald had always maintained a recurring dream about running a race, and then collapsing at the end. As she was graduating from MICA, she was training for a triathlon. Before the race, she happened to go to a doctor—and discovered that despite not showing any symptoms, her heart was operating at a mere 18 percent, and her dream was likely to come true should she participate in the race. Not long after, she had to go home to Georgia to take care of sick family members—and she didn’t paint for a handful of years, which she describes in this episode of Design Matters. She eventually found her way back to her craft, completing studio and teaching residencies in Beijing and Aruba—but life intervened again in 2012. This time, she was in a drug store, and felt a flurry in her chest. She collapsed and woke in a pool of blood, and was taken to the hospital where, two months later, she received a complete heart transplant. Another year would pass before she could return to the canvas—but she returned. When someone is born to do something, they do it. 

She won grants. She was a semifinalist for the Sondheim Artscape Prize. And then a rather amazing thing happened: In 2016, she won the National Portrait Gallery Outwin Boochever Portrait Competition for her work Miss Everything (Unsuppressed Deliverance)—becoming the first woman to do so, and finally winning her mother’s endorsement of her career in the process. At the time, the Smithsonian noted, “Miss Everything is emblematic of the show as well in its depiction of diversity. Unlike, say, the nearby exhibition of presidential portraits …”

Prescient words. Because the following year, something else happened: The Smithsonian announced that Michelle Obama had selected Sherald to paint her official portrait, alongside Kehinde Wiley’s Barack Obama commission—making them the first black artists to create a set of official presidential portraits. The paintings were released in early 2018, with Sherald capturing Michelle using her signature gray skin tones, and an all-encompassing geometric Milly dress.  

Together, the paintings represent brilliant departures from first family portraits of past—and rightfully so. As Sherald has said, nothing about the Obamas was ordinary. Everything was historic, everything was extraordinary: The first black president and first lady. Their presence exuded optimism. Possibility. A new future. Sherald and Wiley’s portraits were the only way the Obamas could have been rendered in an honest way that reflects their electric moment in time for posterity.  Not long after the unveiling of the portraits, Sherald received the High Museum of Art’s prestigious David C. Driskell Prize. And while some articles lead with the illness hook, others go for the narrative of Sherald as overnight sensation, breakout hit—which again, is to overlook the point (not to mention her decades spent waiting tables, only to be free to paint).

These days she generates around 10 to 12 portraits a year, and currently has a deep waitlist for her work. After years of an identity explored, it seems she has found herself. One wonders if with every fresh painting, every subject she so completely and captivatingly documents—if she discovers herself anew, again and again and again.

—Zachary Petit, Design Matters Media Editor-in-Chief


Debbie: The subjects of Amy Sherald's portraits are African Americans. They wear clothing with vibrant colors and patterns and they stand out from richly colored textured backgrounds. They look right at us and they seem to be taking our measure. Their portraits are beautiful, luminous, and intense. When Sherald was asked to paint Michele Obama's official portrait, she produced a painting that was a departure from the traditionally stodgy first lady portrait. Wearing a voluminous dress, Obama is seated against a sky blue background and she's looking right at us, taking our measure. Amy Sherald joins me today to talk about the making of that portrait and her life and career as an artist. Amy, welcome to Design Matters.

Amy: Hi, thank you.

Debbie: Amy, I understand you have a real affection for Teletubbies.

Amy: I do. 

Debbie: Why is that?

Amy: It's very comforting for me it's the happy baby sun, the grass is really green, it looks like a world with no mosquitoes, it's just I don't know, it's just really sweet.

Debbie: You grew up in Columbus, Georgia, the daughter of a dentist and a homemaker, surrounded by what you referred to as generic Ethan Allen landscapes hanging above the fireplace. Your family was not an artistic one?

Amy: No. Actually my mom, funny, she spent a year at the Cleveland Art Institute. She was born in 1935, I say that because she's 85 years old now, so even at her age, and I guess that was in her late 20s, it was not something that had a foreseeable future, so when I said, "I wanted to be an artist," she still did not understand what that meant. There was no 'I can see what this means,' she didn't want to hear it. 

Debbie: Your parents raised you Christian and I understand you had bible studies in your house every Friday.

Amy: We did, yeah.

Debbie: How did that influence you or impact you?

Amy: As a child, I didn't really think about it. We, the church was a rather strange one actually because we kept the Sabbath, so it was no TV after the sun went down on Friday until the sun went down on the Saturday. It was a lot of Old Testament and New Testament stuff, but it's just what I knew, it's what I grew up in, so I never really questioned it and then I let it go once I left home to go away to school. Looking back, I really appreciate the kind of boundaries that it gave me, although they were very myth-y now. I look back and I'm like, 'Oh it's like a fire.' But it's strange looking back, it was perfectly normal when I was a child to have bible study on Friday night, to not to watch Saturday morning cartoons, to come home and have more bible study, it was completely normal.

Debbie: Is religion important in your life now?

Amy: Not so much, I've tried it out in all different forms, and I realized that I more so appreciate living vicariously through people as they worship in whatever religion that they choose, and I prefer to be what I just consider myself a humanist. I have friends from different walks of life that are different religions and take a little bit from everything.

Debbie: I understand that when you first started school, you would draw pictures at the end of every sentence you wrote and so whatever was in the sentence, you'd bring it to life, a house, a flower, a tree, a bird. What did you teachers and parents think of this?

Amy: They thought it was cute. That's was just about it, my mom, now she tells the story like, "She was an artist when she was in the second grade." 

Debbie: But she didn't want you to be an artist.

Amy: She's literally driving the bandwagon now. She hopped on the bandwagon last year, and now she respects me. When I talk about that part of my life, I say that art isn't something that I chose to do, it's just something that I had a proclivity, those are my proclivities to draw. So it was easy and I didn't have to think about it and as a little self-conscious, introverted child, which I didn't know what that was, I just knew I preferred to be by myself, that was the one activity that I could do by myself.

Debbie: Did your friends or family begin to notice any strong artistic ability in these tiny little drawings, and does your mom still have any of them?

Amy: She does have some. She was surprised that I wanted to be an artist, but every single activity that I did outside of school was art, so I had the same art teacher from kindergarten to 12th grade because I went to Catholic school, and from K to eight, it was St. Anne's and then from nine to 12, it was [Pacelli 00:04:45] High School, so Mrs. Davis would teach us in school and then she also taught afterschool at private lessons, so that's what I did my whole freakin' life. Then she's like, "You want to be an artist? I don't understand. You said you wanted to be a brain surgeon when you were five." I'm like-

Debbie: They're holding you to that one?

Amy: Yeah.

Debbie: I read that you remember being drawn to art in the second grade, like, "Art" with quotation marks around it. What first caught your attention?

Amy: I think for me it was how people looked. I was really drawn to what I thought was the aesthetic of the artist, so the kind of Cyndi Lauper, Madonna blue hair, I really drawn to people that were different. When I was in my late teens, early 20s, and I finally moved out of Columbus, Georgia, and I ended up at Clark-Atlanta University, it was the first time I wasn't under my mother's thumb. I shaved my head, I got a labret, I went through my grunge phase, and for me, it's my identity as an artist was expressed in that way, which is really interesting cause as you grow older, you realize it has nothing to do with that, but in the beginning it meant everything. 

Debbie: You've written about attending private schools and being one of maybe two or three black children, and as a result you were raised to be conscious of how you acted, spoke, and dressed. I imagine once you left home and were able to shave your head and wear all sorts of clothes of your own decision making, it was a real change for you. How did your parents respond to that change?

Amy: My mother was embarrassed, my dad was pretty silent about it, but I don't think he approved, but I like to consider myself his favorite, so I got away whenever I wanted to. I went to historically black college because I needed to have that experience because from kindergarten to 12th grade, there was eight black people in my high school, three between K and eight, so I really needed to not be 'Black Amy.' But again, I went through that phase and that phase made me not cool on the black college campus, so I was still an outsider, an inside outsider in a way, but yeah, she had to get over it because I was pretty adamant about who I was at the time. 

Debbie: You were teased while you were in high school, in junior high school. I read that you were called, "Zebra, bumblebee bitch, old yellow," I'm sorry to even have to repeat those words, how did you manage?

Amy: It didn't bother me, but I also felt at some point I had to stick up for myself because my brother got teased too. So in sticking up for him, I would stick up for myself, that was the first time I said my first curse word. I think it was fifth grade, there was this girl name Robin, I hope I'll never forget her, and she was brown too, she was Indian or something like that, and she had been saying it to me over and over and over again, and I was trying to ignore her. Then I said, "You shut up, you bitch." She was like, "Ah!" She couldn't believe I said it and she left me alone for the rest of our elementary school career, that was it. 

Debbie: Standing up to bullies.

Amy: Yeah.

Debbie: I know that in sixth grade you took a field trip to a museum and it was the first time you saw Bo Bartlett's painting, Object Permanence, in which the white artist, Bo Bartlett painted himself as a black man and I know that was a really profound moment for you. Can you talk about that a little bit?

Amy: In hindsight, I was in the sixth grade, so I don't think I really, really understood what was happening, I just realized that I had never seen anything like that before, it was a shock to my system, but I also remember in that moment that I had this moment of self-determination where I'm like, 'This is what I want to do.' I knew in that moment in seeing that painting that, that's what I wanted to do, I wanted to make paintings like that. I wanted them to have people in them and beautiful skies, and the kind of simplicity of every day American life that he portrays in his work. 

Debbie: Did you know that he was a white painter painting himself as a black man in that painting?

Amy: I didn't find out until three years ago, I never knew. When I saw it, and I don't know whether this is just because I was raised in the South and that's just my mindset was formed by all these different external directives, but he had utility belt on and stuff like that, and there were two white children, and a white woman. They were standing in the front yard, so I just assumed he was the maintenance guy or whatever, so finding that out it really ... I was shocked, I was really shocked, yeah.

Debbie: You said this about the experience of seeing it, "I've forgotten a lot of things, I've forgotten how to play the piano and had to speak Arabic, though I studied it for two years, but I'll never forget how much it meant to me to see myself in that museum." Arabic and the piano?

Amy: Yeah.

Debbie: You've forgotten both?

Amy: I did. 

Debbie: Oh no.

Amy: I can say it makes me angry about the brain because I would be a genius right now because I'd be fluent in German, in Arabic, in Spanish, I would play chess, but you get busy with life and all of sudden it was just gone.

Debbie: In addition to being a dentist, your father also started a barber shop and you've stated that all the women in your life had master's degrees and were teachers, and as a result, your dad told you that the civil rights movement was not about you being an artist-

Amy: Yeah, that's what my mom said.

Debbie: Your mom said that?

Amy: Yeah.

Debbie: What gave you the sense that you were going to do it anyway?

Amy: I didn't feel like I had a choice. 

Debbie:  You went pre-med.

Amy: Yeah because my father was one of the first black dentists in Columbus, Georgia and then other people started moving in and they were ... These doctors came together and they really were pushing for young black students to take on those professions, so much so that they were willing to help us pay for school. So I felt pressured into doing it, but I really didn't want to do it, but it's like those are my choices. It's my great-grandfather that started the barber shop, so it was started in 1898, so it's the oldest black owned business in Columbus, so it was that, which obviously I wasn't going to be a barber even though I enjoyed it. My great-uncle had a mortuary that was next to my dad's dental office, which was always fun as a kid to go in and poke at people. 

Debbie: Sounds like Fun Home.

Amy: It never crossed my mind to become or own a mortuary. I just kept always listened to my inner voice. My intuition is really strong, and I tried to do what my parents wanted me to do, but my life didn't really start to come together until I started to make my own decisions about what I wanted to do. That's what I tell a lot of young people, it's almost magical what happens once you commit to what you were brought here on this earth to do, once you commit to that it's like your life is charmed and things just fall into place the way you need them to, it's really crazy.

Debbie: I read an anecdote about a man that talked to you about talent, and it's now connecting to the idea of forgetting Arabic or forgetting how to play the piano, and he said ... You were talking to a person who was in front of the library at your school-

Amy: Yeah and he said sell his art.

Debbie: Sell his art and he asked to see some of your work, and you showed him, and he warned you that if you didn't use your talent, you'd lose your talent. If you didn't use your Arabic, you lost your Arabic.

Amy: Yeah, I lost it. Yeah, that did shock me, and I immediately decided that I needed to change my major.

Debbie: That was your junior year?

Amy: Yeah, going into my junior year. 

Debbie: You started to take art classes with the Panama born artist, Arturo Lindsay, whose work focuses on the African influence on the cultures of the Americas. You've said he opened your eyes to what it was like to be a living artist.

Amy: Yeah, he was really the first living artist that I knew, so I go into the museum when I was in the sixth grade, but there's nothing beyond that honestly. Then he sent us to an exhibition he was having in Atlanta, and that was the second time. I was just like, 'this is amazing,' then I begged him to get into his class because the painting class was full, he let me in, and then eventually I begged him to let me work with him. I brought these paintings over that I was doing, it was your typical face of Miles Davis that everybody does, that close up shot, and then some images that I had torn out a National Geographic Magazine that I tried to render. He was really nice about it because I'm sure they were really, really bad, but he let me work for him, and I worked for him for free for five years, but I got so much out of it that it's been worth it now, I call him my godfather. 

Debbie: You also worked with Nerdrum Odd. What was that experience like? His work is unbelievable. 

Amy: It is, yeah. I discovered his work in graduate school, and just had the impenitence to contact him, it didn't work out, I couldn't figure out a way to get in touch with him, and it just so happened that the next year, one of the teachers in the painting department decided to bring him down to MICA. He had a show up here at Foreign Gallery, so he came down to do a talk. As soon as I found out he was coming down, I'm like, "Okay, this is what I'm going to do. I'm going to get there early, I'm going to let him know I want to study with him," and all that honestly took all the courage I could muster up because I was so intimidated and just still self-conscious to the point where I couldn't even speak in public without crying, and I was 28 years old. I was a little weirdo. So, I did that, I got there early, and I saw him walking down the stairs of one of the buildings, and he just happened to be walking down with Barry, who brought him, and Barry said, "This is Amy Sherald." He pointed to one of my paintings, and he was like, "Nice to meet you, what are you going to do when you graduate?" I said, "Well, I want to come study with you." He's like, "Oh okay well talk to my wife then because she takes care of all that."  I did that and then funny story, so there was a reception afterwards and the person who was supposed to take him back to the train station, their car broke down, so somebody walked up to me and said, "Odd needs a ride back to the train station, can you take him back to the train station?" I'm like, "Yeah, sure." Then I was like, 'Yeah, okay, now I got to go find a car because I don't have a car. I would need to be driving.' So I ran around frantically asking people, and my friend Dana, she was like, "Yeah, sure." So we did it, and I was able to put that in the letter to remind him because he had students all over the world writing to come study with him. I'm like, 'I think that's the little things like that that just work out because you're ready.'

Debbie: You said that you learned more in the experience of working with him for four months than you did in your entire school experience, why is that?

Amy: There were students there that were coming from the Florence Academy, [Spellman 00:15:57] had a great art program, but it was not comparable to that kind of art program. So they were just really well versed and I got to see how they started their paintings and watching him how he started his work, and it really helped me clear up some things because when I change my major when I was a junior, I really didn't have a lot of time to take these classes and catch up, so they let me do directed studies, so I really in a way, I really do, not even in a way, consider myself self-taught because I had to figure a lot out on my own. Just the more that I painted, the better I got and then being there with him made it all click. When I came back I didn't paint for almost four years, but my first day back in the studio after four years of not painting, but thinking about it every day was one of the most beautiful moments because I was finally at ease with it and I wasn't struggling with some of the basic things that I probably would've learned had I been able to take more extensive classes.

Debbie: You just referenced not painting for four years, so after you got your master's degree in fine arts from MICA, you left Baltimore to return to Georgia to take care of your ailing family, several members of your ailing family and you didn't paint then for four years. You said that care taking satiates something inside you that you didn't miss painting when you were taking care of your family because it comes from the same place. 

Amy: It was really interesting that I didn't because really for a short time I was like, 'Do I even want to paint anymore? But then what else would I do?' It's a salient part of who I am is I like taking care of people. Some people are just born with empathy and they're just born to do that, so I really enjoy the challenge of caring for my great-aunt, who was 94 years old, and making sure that she was comfortable. So if I put her in a position, then I would go lay in that position to see how it felt and then adjust it based on what I thought was comfortable and uncomfortable. Just really being intuitive about what she needed, and I just really enjoyed it.  My father wanted me to be a doctor, and although I didn't want to, I felt I would've been a good one because he had me work with one of his friends, who was an internal medicine doctor for a year, and I was able to follow him around. I was like, 'I could really do this,' but my father had a master's degree in biology and he tutored me and I just passed my tests. It's not because I didn't know it because he's like, "I know you know it," but I was just a poor test taker and then in 1992, nobody knew what a visual learner was, so I was just like ... It's like Arabic when I look at it, I was like, "I can't even understand what I studied last night when I looked at it."

Debbie: While you were in painting, while you were taking care of your family, did you question whether art was your true path, whether you would go back to it? Do you have a sense that art was your true path, whether you would go back to it? Did you have a sense that ...

Amy: I did. Yeah, I questioned it. I tried to make some things work out while I was there, like tried to get a studio, but it just didn't work out. I always thought back to that one part, and I was just saying recently I needed to re-read this book, but I just thought back to "The Alchemist," and that part the guy's in the crystal glass shop and he's working and he feels like he's not moving towards his goals, but you come to realize that things are happening whether you realize it or not, so you feel like you're running in place but the world is still moving. If I had done all the things that I wanted to do at the times that I wanted to do them, then maybe I wouldn't have been at the right place at the right time for some of the greater things that happened, like including being able to paint Michelle Obama. 

Debbie: Let's talk a little bit about that recurring dream that you had as you were growing up.

Amy: I always regret telling that because it sounds so crazy.

Debbie: No it doesn't. It doesn't at all. It's so interesting. I've had a number of conversations this week with the theme that keeps recurring. People keep talking to me about the fact that they feel they're not living their life's purpose and now here I am having an interview with you where it's very clear what your life purpose was once you found it and then everything, as you say, clicked into place. But there were lots of struggles along the way, one of which being your heart. Talk about this recurring dream, if you can, and then what happened.

Amy: I want to say I was like 13 or 14 and I saw my first Iron Man, and it was the most profound thing I had ever seen. I feel like it was the one where the father had pushed his son through the whole race, like swam with him, put him in the boat. He was paraplegic or something like that, like he couldn't move but they wanted to do the race together. I was like, "I want to do that too." It's always been a dream of mine, but also my whole life I had a recurring dream that I would run a race, cross the finish line and I would have a heart attack. I didn't really think much of it until I was in graduate school and that's where I met one of my closest friends whose now husband had completed an Iron Man and he was like, "Yeah, sure, I'll train you." I started swimming and biking, running and all that stuff and I just decided to go to the doctor. I didn't have insurance at the time because I was in grad school, but we had like a little clinic that we could go to, so I went to the clinic and they were like, "You look pretty good. You're healthy. You have an irregular heart beat." I said, "Well I've always had that." They said, "Well, we're just going to check it out just in case," so I wore a Holter monitor for a while and that was a little schizy. They were like, "Okay, we're going to do a sonogram." I just remember the doctor saying, "Wow." I was like, "What? It looks great?" He's like, "No. You have the heart of an 80-year-old woman." I'm like, "How is that even possible? I just ran an eight minute mile yesterday." He's like, "You did what?" I'm like, "Yeah." It was like no symptoms at all, outside of the fact that I couldn't push past an eight minute mile. I was like, "It makes sense now." I thought it was my asthma or something like that. That moment my life changed because my identity as an athlete had to come to a complete stop and that was something I really didn't realize how much that was a part of who I thought I was until that moment. 

Debbie: Well in 2012 on a trip to Rite Aid for some supplies, you felt a flutter in your chest and you passed out and woke up on the ground covered in blood. You were then taken to the hospital in an ambulance and ultimately had to receive a total heart transplant. I understand you then took another year away from painting. What was that experience like and how are you feeling today?

Amy: It was kind of scary. I always like to consider myself a preparer.

Debbie: How do you prepare for that?

Amy: I don't know. I told this story when I was 16, I was driving to school and I left the same time as my neighbor who was an old gentleman would come out, he would come out the same time every morning at 8:15 and start his car. I left that morning, I saw him go out and start his car, I came back and I noticed his car was still running because I could see the white smoke coming from the back of it and I was like, "Huh." So I walk next door and I look through the screen door and there he is, his head is back and he had had a massive heart attack. For me, that was really my first confrontation with death, and for some reason in that moment I was like, "I think I need to prepare. I need to prepare for my mom to die, I need to prepare for my dad to die," because this is so real and you never know when it's going to happen. I had come across this documentary, I can't remember her name, but she was like a death coach. Do you know who I'm talking about?

Debbie: There's been so much now written about understanding death better.

Amy: She was a doctor and she didn't like the way that doctors were speaking to their patients, because they weren't really being honest with them about what was happening and with their treatment, then when it came time for her to die, she was really not ready for it. I was like, "Wow, that's really interesting, because you spend your whole life and passion to do this work."  When I had gone to the Rite Aid, I had gone there to buy some saran wrap to wrap some paintings that a collector was coming to get because it was my first acquisition and the work was going to the National Museum of Women in the Arts, and when I had that flutter and I woke up and I was like, "Oh shit, what happened?" They put me in the ambulance and it was like the worst place to black out because it was a neighborhood that had a methadone clinic and it was like heavy traffic and stuff and so I ran into a woman who saw me, who just happened to be there, and I ran into her a year later, and she said, "Yes, people were just stepping over you, because you had thought that you had just blacked out." Luckily the manager came. But when I was in the ambulance on the way to the hospital, I felt the fear because I really felt, my heart felt weak. I was already to the point where I shouldn't have been walking. I walked from my house to that drug store. I was getting out of breath walking to the bathroom, but I was like, I'm like Superwoman to myself. I'm still a triathlete, so I was pushing myself. I thought about that documentary, I thought about that moment and I was like, "I can't die scared. I need to make peace with this." There's really no way to know how you're going to feel in that moment, because even in that moment you're still not really confronting death in a real, real way, because there's still a chance you're going to live. I just talked myself out of being afraid and a little bit of levity. Not like Sallie Mae can kiss my butt, I don't have to pay taxes anymore, so many things that I'm going to be able to escape. I was in the ambulance by myself so I had nobody else to comfort me but myself. That's when you really got to stand up for yourself and just walk the walk. 

Debbie: Did that change the way you wanted to live? 

Amy: Not really, because I've always been the same person when it comes to how I live my life and the kind of decisions that I make and just really being authentic. No, it didn't but I live harder now, which I lived hard before, but now I feel like I'm the living legacy of a woman and my life is to be lived in her honor. I think about that a lot, but I've always been a giver. I'm always the person that's pulling out the dollar bill to the homeless guy or whatever. That's always been a part of me, so I didn't really change from it, outside of the fact that I feel like I'm less afraid of not being here anymore.

Debbie: I know you have a relationship with your heart donor's family and you've stated that everyone should be an organ donor, and I agree, and for anyone that's listening that would like to eventually donate their organs, where can they sign up? Where is the easiest way for people to be able to donate their organs?

Amy: When you go get your driver's license renewed, I think that's the quickest way. It's funny, I went to go get mine renewed and I was sitting there and it was like a year and a half after my transplant and I watched like 20 people go up and they asked them the question and they all said, "No." And I wanted to be that weird chick that stood up and was like, "Hey, look guys. You could end up with a person that has your organs like me," but I just kind of sat there but I realized there's a lot of work to be done because people are really afraid of it, and it's nothing that you would ever really confront. You don't really think about it until it's your family member and then you're like, "Wow, this would really have had made a difference." It's one of the most important things you can do and it's a legacy that you can leave behind, the gift of life. It's just such a beautiful thing. 

Debbie: Everybody that's listening, sign the back of your license. Was it hard to come back to painting for a second time?

Amy: It was, because there were so many things that were affecting who I was. They don't explain to you the effects of the anti-rejection drugs and because I was in childbearing years I had to take more and they're neurotoxic so you feel kind of crazy all the time and you're a little bit anxious and a little bit depressed and a little bit angry, not really sure what's happening. I remember I called some friends of mine and I was like, "I don't think I want to paint anymore. This is stupid. I don't want to do this anymore. I need to do something more meaningful and I just don't like it." I was looking at Master's degrees in urban planning, anything else for some reason.

Then I went to see a transplant psychiatrist and I got my brain back together. Whatever chemical imbalance happened from the surgery. Then I was like, "Oh, well I actually do want to paint now." But it took me a year and a half to get that together.

Debbie: At that time, were you still waiting tables?

Amy: No. By that time ... I quit waiting tables ... I got the transplant when I was 39 so around 37 I knew I had to make that jump and be full-time and it just so happened that I had the choice to set my life up where I was house sitting for a doctor who had decided to go practice in Florida. I took care of his house and watched his house, so when I did quit I only had to worry about paying for my studio. If I was living off of $150 a month it didn't matter, because at least I had a roof over my head. That was the case for probably the first year, just eating frozen food and trying to make it happen with what little I had. 

Debbie: I read that you said about waiting tables that you did a job that you didn't want to do so you could do a job that you wanted to do, and I love that.

Amy: Yeah. You never want to become complacent and for me there was a desperation to not have to do that anymore and there's some aspects about it that I enjoyed, because I worked for an amazing chef who was just awarded the James Beard Award and I learned a lot about food and wine and I'm really passionate about that and inspired by a lot of chefs, because they're inspired by art. Part of how we manifest our lives I think is from that kind of desperate energy that you push out and pull in and it draws whatever it is supposed to be into your world, but I think if you have an option, if you're okay, if you don't need to pay your rent, if you don't need to eat, then things, I truly believe they play out a little differently.

Debbie: You've stated that you don't think your success would have come to you as easily had you not committed to making the work in such a way that made you uncomfortable. I love that you think that your successes come to you easily given what we've just talked about, but how does your work make you uncomfortable?

Amy: I think I was talking about the other work, not my work necessarily, but the work that I had to do to support the work. That was uncomfortable, because as a 36-year-old, 35-year-old, 37-year-old, it's like there's a little bit of shame that comes along with that because you're older, your friends are having babies, they're buying Mercedes Benz and shopping for patio furniture and you're at work every weekend doing something that they don't understand and they kind of think of you as wasting your life away, because they don't share the vision that you have and you know exactly who you're going to be so I really thoroughly enjoyed all of the success that I've had, because I'm able to poke my tongue out at all those people and be like, "Yeah, you know, you didn't believe in me and if you had, you would have bought a painting when it was $1000 and now you might be rich." It's those kinds of things that make me giggle. 

Debbie: Let's talk a little bit about your style and your process. I'd like to talk a little bit about your use of color. Early on you had a friend who suggested it would be easier to paint flesh if you did so in gray scale first and he suggested black and Naples yellow over black and white which comes out very silver, and you tried it and liked the result of the gray skin and decided to keep it. Can you tell us a little bit about why you chose to move forward with that specific look philosophically?

Amy: I was going through the process of trying to figure that out. It's just those two colors but they're not over the black and white. It prefer it to the black and white because it does, it's an icier kind of gray. I think, because the work that I was doing in graduate school, it wasn't what I needed it to be and when I tried to go back to it, I knew inside of my heart that it wasn't sophisticated enough to get me where I wanted to be, and after the journey of spending a year trying to figure out what I was going to make and not being productive in the studio, going there and sitting and leaving there feeling like, "Is this ever going to work out?". Because I couldn't figure out what it was and having that epiphany where I saw the movie "Big Fish" and it clicked for me what I thought was necessary that I felt like was missing from the conversation in the contemporary art world. So I really knew that I wanted to make these images and these paintings of black people that were just that, just paintings of black people and so for me, I think I was subconsciously a little afraid that the conversation would be pushed into a corner and I didn't want the work to be marginalized in that way, because I needed it to live and to be bigger and to exist in a different space, and so that's I think why I settled on that and I say all of my decisions of course at first are aesthetic, so things look cool first and then you're working on them and then the work ... you sit back as you're streaming through your subconscious and so it's hard to be aware of those two things at the same time. When you're done, you sit back and you look and you have conversations with people, like, "Yeah, I think that's what happened." 

Debbie: I have two questions about that. The first is about your decision to exclusively paint people of color. How did you arrive at that decision?

Amy: It was a natural decision for me. I don't think it was a choice, because I don't think white people sit around and think "I'm only going to paint white people." They paint their ideal selves and I'm painting my ideal self. People ask me at artist talks, "Are you ever going to paint anybody white? We think you should." I'm like, "Well, I think you should reconsider what you're asking me, because you need to take a little walk around the museum and you should probably open up a history book or two and then get back at me because I think it's really interesting how they can see the absence of themselves but they can't translate that and see how I may feel that there's an absence of myself within our history and just in general, so it's just really funny to me when that happens, but I have no reason to paint white people because like Kerry James Marshall said, he's like, "Whiteness has been perpetuated for centuries." It's like what do I have to do with that? I have nothing to do with that. I'm wholly committed to putting more images of people that look like me in museum institutions and changing the expectations of what people think they should see when they go to a museum and creating spaces for black people to walk into places like that and be confronted by an image of themselves where they will feel loved and affirmed. I also think that other people who are non-black can look at the work and possibly because you subtract the way that we identify with each other through skin color to possibly be able to internalize blackness and see themselves in a way in these images. I always say I totally identify with Reese Witherspoon in Legally Blonde. I watch that movie and I'm like I've internalized white women to the point where I can look at her and see myself. I think for me, I think that's really an important part of the conversation about race in the States. There's still like a separation. 

Debbie: What created that cathartic moment while watching "Big Fish?"

Amy: It was a feeling of jealousy, of wanting to have access to those kinds of narratives and feeling like you're written into history in one way and wanting to expand my identity in that way and a lot of that had to do with feeling like I only had nine years to live after being diagnosed when I was 30 and really wanting to figure out who Amy was outside of all the external directives, outside of the ... I was raised to be a Christian, you talk this way, you walk this way. You're completely codified from birth and who am I outside of all of that? What parts of me are really me? I think moving back home really was the impetus for me to really ask those questions about who I was because I realized that I shifted back and forth into a performance, especially in my hometown because of the ways that I grew up and the interactions that I had and the kind of whiteness that made you feel like you had to prove your own humanity, that you were smart. I don't feel that way everywhere. I am only as black as you are white and there's certain people that really live in their whiteness. In Columbus, I felt that that was very present. I never associated the flag with myself. I associated it with those kinds of people. That performative aspect of my identity and race as theater were really things that really sparked that conversation and then wanting to step outside of that and see what else was inside of me. 

Debbie: Your paintings are extremely emotive. You can't help but feel something when you're looking at the people that you paint. Has it always been that way? I haven't been able to find much of your early work. It almost feels as if your work came out fully formed. 

Amy: You will never, ever see the old work. 

Debbie: But there is a certain presence to every single portrait you've painted. It feels as if it just happened that way. How did you get to that particular moment in your work? How did you get to that particular moment in your work and know that that was what you wanted to continue to pursue?

Amy: I honestly can't say that I knew that I was doing it when I did it. You know, I think the first moment that that thought even crossed my mind ... because I've always been, obviously I have a healthy amount of self-doubt. I just don't think I'm that great, you know. I tell people, I'm like "I'm not here because I'm the best painter. I'm here just because I worked hard and I didn't give up." And sooner or later everybody else gives up and you don't, so you end up at the top. But I ...

Debbie: Do you really believe that?

Amy: I mean, kind of. Kind of, yeah.

Debbie: I mean, you're extremely ... your paintings are just unbelievably amazing. It just feels like it's more than just working hard or luck.

Amy: Yeah, it's not empirical. There's two million people trying to be artists at the same time as you, and who gets to be chosen, and then who's chosen and who's still going to be there in 25 years? It's like there's strategy to that. It's definitely, in a lot of ways it's not random, because there's ways to do it. You just have to be aware and look at the system and see how it works. But yeah, I don't ... I didn't know I was doing it until I had a show, and I had like three people start crying while they were looking at the work. And I was like "What is wrong with y'all?" So it's just really ... it was just really a moment for me. I was like, something about what I did is moving these people, and I don't quite understand how to explain it. I mean, the way that I explain it is that I'm so particular about the people that paint and what kind of energy they hold within themselves that maybe somehow that is what's translated into the work. But I don't know.

Debbie: So you use models for your work, and you essentially pick people that you see on the street, and you photograph them outside before painting them. How do you first choose, and then approach the people that you're interested in?

Amy: I kind of live my life and I find people, I see them. I met the last two models that I painted for my show at Camp St. Louis, came to me because when the movie Black Panther was out, I contacted a friend of mine and I'm like "I want to raise some money to send a whole school to see the movie." And they put me in contact with this young woman, and she was an alumni of the school, and she was like "I would love if you would help me do this." And so when I went to meet here, she was there with a friend of hers, and as soon as I walked in ... and I brought my assistant with me, and she was elbowing me, like "You got to paint them." I'm like "I know, they're perfect." So it just kind of happens like that.

Debbie: And then you also find what you want that person to wear. They're not just wearing what they ...

Amy: Yeah, sometimes they are, that walking archetype. And then sometimes I figure out what I want them to wear.

Debbie: Let's talk about one of your paintings that has captivated our culture, your portrait of Michelle Obama, which was unveiled alongside Kehinde Wiley's portrait of Barack Obama earlier this year and marked the first time official portraits had been created by black artists. Tell us the story of how the commission came about.

Amy: Well, the National Portrait Gallery worked with the White House curator and they gave them a portfolio of, I heard, like 21 artists. And they made a short list of five, and then I got the phone call, it's like "You know, they want to meet you." And I'm like "Oh, my goodness." And went to the White House July 2016 and had a conversation with them in the Oval Office. Obviously I don't remember much of that conversation because I was so nervous, but it was really mostly about what I did outside of painting. You know, so I was able to talk about some of the work I did with Youth Works and working in Baltimore City Detention Center, and reentry programs that I want to start in the future and that kind of thing. And we got to the art at the end of it, and I was like "You know, I really would like to paint you." And I said "But I didn't want to do it unless I could do it the way that I paint." because for me it was kind of pointless. And she was like "Absolutely." So I still, at that point, didn't know that I had it. But I found out two months later.

Debbie: Now, I believe that this meeting happened after you won the National Portrait Gallery's portrait competition for your work, "Miss Everything." That whole experience, getting the support of even your mom, finally, after you won the competition, she then sort of felt like you were an artist, you were a real artist. She understood what you did. That was the moment that really changed how you were viewed in culture. Is that true?

Amy: Yeah.

Debbie: It was before the portrait of Michelle Obama.

Amy: Yeah. There were two moments. One, in the beginning, was when I was ... I guess it was like 2009, I had applied and reapplied to New American Painting, it's like a juried exhibition that ends up in a catalog. And that year I got chose as jurors' pick. So that was a bump, because it put me on the national scene a little bit, and I started to get these phone calls from not major galleries, but smaller galleries. And everybody has to start somewhere. And then worked my way up from there and was really at a point where I needed gallery representation and I was trying to figure out how to get it. And for me, collectors have really been the advocates that I needed, because they're the ones that can make the introductions, because you can't just walk into a gallery and say "I really want to show with you." It just doesn't work that way. So yeah, my work was selling, but the funny thing is, I was still broke. It's like in the beginning your work is not selling for much, and so I think they were like $7,000, which meant I was getting half of that, which meant if I only paint 12 paintings a year I was making $36,000 a year, so there was always like a few months of the year I couldn't pay my rent. And I remember having to borrow money just to get down to DC to get to the reception. I had no money and I was six months behind in my rent, and I was like going through different scenarios of like if I won first place, second place, third place. If it was third place I'd only get this much money and I'll only be able to pay back this, you know. And so I really honestly, 100% did not think I was going to win first place. And so that was a real shock.

Debbie: That was $25,000, correct?

Amy: Yeah, but again, that's when the magic happened, because I was at a breaking point. You're at the edge of the cliff and you're like waiting for the next step to appear. And there it was.

Debbie: I understand that when you were in the room with President Obama and Michelle Obama, you actually said to Michelle that you really, really wanted to work with her. And at that time you were being considered for the artist for either of the portraits.  Did President Obama seem slighted by your wanting to do the portrait of Michelle more than him?

Amy: No. You know, they were both asking me questions, and then he was like "Well, how would you paint me?" And I was like "I don't know, I haven't even considered it." You know what I mean, and then Michelle was like "This is not about you." But it would have been fun to paint either one of them, but I really think that I was the right choice for her.

Debbie: What was it like when she came in and sat for you to photograph?

Amy: It was ... you know, she's very relaxed, and so you kind of feel silly for being nervous. But I was really nervous, and tried to be as present as I could, but it's almost impossible, because you're like ... you're just nervous. But it was easy, I had an hour and 15 minutes, and I just did what I had to do. Like set up the camera and like figured out where I was going to photograph her, and I had to move her around to different areas because I was trying to get the light that I wanted. Yeah, and it was fun. We put on rap music and just kind of made it happen.

Debbie: And was she wearing the dress that she was ultimately wearing in the portrait that you painted?

Amy: Yeah, that's the dress she showed up in. I worked with her stylist, Meredith Koop, and kind of vocalized what I wanted, what I was looking for. And we started with 11 dresses and then narrowed it down to four. And then I had chosen two, and the one that she wore was one that I was really into in the beginning because of the ... I don't know, like I needed the dress to be a painting in itself too, for some reason. I was really into that, and ...

Debbie: It's very geometric, very Mondrian.

Amy: Yeah, you know, and I mean, the quilts were the first thing that I thought about, and that was, for me, a connection to Gee's Bend and black history in a way. But still connected to the history of painting and art in that way. And it just worked.

Debbie: You have said that it's your job to paint people, and you were approaching the project of painting Michelle Obama as if you were painting just another person.

Amy: Yeah.

Debbie: Did you feel the extra weight of her significance?

Amy: I felt the judgment before I even finished it.

Debbie: Were you concerned about what people were going to think?

Amy: Yeah, I feel like I was, because I'm normal. You know, it's like of course you're like making one of the most important paintings in the world. You know you can't please everybody, so those thoughts had passed through my mind, and I just tried to push them away and just like ... I had to just make a painting. I just need to finish this painting of her and not think about anything else but what I'm painting.

Debbie: You've said that as a portrait painter you have the capacity to capture something that is not captured in photography. What do you feel you were able to capture about Michelle Obama?

Amy: Well, when I first started to do research for the painting, the first thing I did was go online and look at the thousands of pictures that are on the Internet. And all of them are her public self. And I really wanted to ... because what I was sharing with her in that moment was very intimate, I wanted it to be a part of her that we don't get to see. I think I captured that in that moment. I mean, I kind of had that feeling in my stomach when she got to that pose, and I knew that that's what the painting was going to be of.

Debbie: The way she's sitting, it feels very ... almost mountainesque. And I remember years and years ago seeing a behind-the-scenes shoot of Kate Moss posing for the cover of Harper's Bazaar, and it was revealed that underneath the gown she was wearing she was actually standing on a stool, and it made her appear much, much longer on the cover. And I was wondering, did you extend the dress down further? It seemed ... I was really trying to analyze it, like where could her knees be? And if her knees are there, where are her feet? And she just seems so much larger than life. And this is a woman who is larger than life. And so I was just wondering if you could give us any perspective on how she was sitting.

Amy: So when she came out, we started with standing poses, but the dress wasn't being brought alive in a way that really activated. And so we brought a stool out, and I had her sit facing forward, but then the dress just kind of fell on either side of her legs, like they were ... you know, she sat with her legs together and it fell on either side. And it was nice, it kind of laid out in the same way, but I lost a lot of what I was looking for. And so that's why that pose is so perfect, but she's sitting on a stool with her legs crossed. And so that kind of lifts it up. Then also, the material of the dress is a nice kind of stiff poplin, and that has body. That's how it worked.

Debbie: I know that protocol dictates that the First Lady must approve the painting before it's released, as does the Portrait Gallery's advisory board. When you sent it to them, what was the waiting process like? Was it, were you nervous?

Amy: No. I knew I had done the best that Amy Sherald could do at that time. So I really wasn't nervous about it.

Debbie: As with anything in the public sphere, there were a few naysayers about the work, mostly from people who I think didn't understand the work and what you were doing, and also your body of work and what it means philosophically. Did that upset you at all?

Amy: It didn't upset me. I mean, people can be mean, and it upset me when it started coming into my inbox from my website, you know. That people think they can just say anything to you and the hostility that came along with it. And one of them, one of the emails said "You just gave Trump supporters something else to laugh at." And then the next day I got two emails from self-professed Trump supporters who were white men from the Midwest, who were like "I saw you on the CBS Sunday morning show, and I just want you to know I'm a fan of this painting and I'm a fan of you." So I'm like, you know, it just ... so it gets at you a little bit, because again, I have that healthy dose of self-doubt. So it's like "Are they right?" But then you just let it go, because it wouldn't have made it that far if she didn't love it and if the advisory board didn't love it either. So their reactions were affirmative enough that I didn't have to think about the trolls.

Debbie: I want to talk with you a bit about success. You stated recently that success is wonderful, but it's definitely something to be reckoned with. In what way?

Amy: It means more work. I think a lot of people don't understand that. It's like "Oh, I'm here now, this is great," but it also means that there's a demand for the work, so it also means that ... you know, if I was in the studio 50 hours a week, and I pretty much worked seven days a week for the past three years to get me to this point, the hours don't get less, they get more. And you really have to learn how to say no, you have to learn how to take time for yourself. I've been the kind of person that has worked out every day of my whole life. Like even after my doctor told me "You can't work out any more," I still found a way to work out in those 10 years waiting for my body to get to the place where I could get the transplant. And last year was the first time I skipped four months at the gym, and at 44 it's like not what you want to do. Because when you start, that gets like "Oh, my God, what happened to my body?" But it's like those are the lessons that I'm learning. Because I got sick after I finished that portrait.

Debbie: You did?

Amy: Yeah, I had exhaustion. It was just like the adrenaline left my body, and I was down for like three or four days. And so you have to learn self-care. And I think that's part of it, it's like everything comes with a sacrifice. Because working all the time means that other parts of you are dying. The parts of me that love to read, but it takes me a year to read a book because I read at night and I fall asleep in 15 minutes. You know what I mean? So I feel like I'm not taking in as much information as I used to, when I had time, but it's time, no money, or money and no time. And that's usually the way that it plays itself out.

Debbie: And you've just recently signed with Hauser & Wirth. Do you feel more pressure to paint quicker? I know that you paint slowly, you do about 12 portraits a year. Do you feel that that is going to be impacted at all?

Amy: No, I mean, I made it clear what my production was going to be. So no, I don't think so. I mean, it gets easier because you start making a lot more money. To have to make that many paintings to eat is one thing. I can relax a little bit and produce what I produce. But yeah, I definitely know I have to make a specific amount of paintings a year, if not more. And depending on what my pace is, then that'll be what happens.

Debbie: My last question, Amy, is about self-portraiture. I understand at one time you intended to paint a portrait of yourself as the tin man from the Wizard of Oz. what influenced that decision, and do you think we'll ever see that painting come to life?

Amy: Probably not. I was in the hospital, my brother had just died, and I was really thinking about stuff. And just thought about him and his courage because he had a non-smoking lung cancer, and he was so afraid to feel like he was going to be suffocating. And luckily, he didn't have to go through that. But just thinking about both of us together going through that at the same time in two different states. And I had left him, come back to Baltimore, thinking that I was going to return, and all of a sudden, I'm admitted into the hospital, so I had to call him and say "Hey, look, this is what's happening. You're in the hospital, I'm in the hospital. We have to figure out a way to tell Mom so that she doesn't freak out." And so we did it, we got on Skype and talked about it. But I think that's where the thought really came from. And maybe I will, but I don't think I will. I did a little drawing that day in the hospital of that, and yeah, I think I let it die.

Debbie: Amy, thank you so much for being on Design Matters today, and thank you for creating such magnificent and important work.

Amy: Thank you, thanks for having me.

Debbie: You can find out more about Amy Sherald and see some of her portraits on her website, This is the fourteenth year I've been doing Design Matters, and I'd like to thank you for listening. And remember, we can talk about making a difference, we can make a difference, or we can do both. I'm Debbie Millman and I look forward to talking with you again soon.