Debbie Millman
Episode 51

Debbie Millman

Episode 51

Debbie Millman on the Importance of Playing the Long Game

Interview by Spencer Bailey

For much of her life, artist and designer Debbie Millman has been fascinated by the power of branding. Today, as the host of the Design Matters podcast (which was recently translated into a book, out next month) and the chair of the School of Visual Arts’s Master’s in Branding program, the discipline is constantly on her mind. For Millman, part of branding’s allure stems from the exercise of clearly and confidently expressing a purpose and meaning—a challenge that she has concurrently grappled with on a personal level. The parallels between aims in her work and life are no coincidence: Millman’s professional projects are often her way of searching for answers to life’s deepest questions, and as she nears 60 (her birthday is on October 29), have brought her to a place where she sees that she no longer needs to strive for security or validation. Now, she believes, if she’s a little more patient with what she takes on, life will unfurl in the ways it’s meant to. 

Millman has long thought about and explored design’s ability to reveal people’s innermost desires in various ways. As a young girl, she fanatically collected Goody barrettes, captivated by their capacity to make her feel prettier simply by wearing them. During college, she worked at her father’s pharmacy in New York’s Hudson Valley, observing how and why people bought the sundries it carried. She later applied that knowledge to her work at several prominent New York City agencies, including Sterling Brands, for which she served as chief marketing officer and president of its design division for 20 years, and was part of teams that created identities for brands such as 7Up, Burger King, Tropicana, and Twizzlers. She even moonlighted as the first-ever creative director of the pioneering hip-hop radio station Hot 97. Along the way, in 2004, she received a cold call from the internet radio network Voice America, asking if she wanted to host a talk show on design and branding. Millman jumped at the chance to put her know-how to use by interviewing people in her field that she admired. The show Design Matters was born. A decade later—after Design Matters evolved into the anchoring show on the website Design Observer and expanded to include guests from other artistic industries, such as musician David Byrne, artist Marilyn Minter, and Nobel Prize–winning neuroscientist Eric Kandel—Millman realized what she’s really trying to do with each interview: trace the arc of a person’s creative life, and understand how they became who they are.

Her career has helped her recognize the importance of slowing down, and of trusting that she doesn’t have to approach everything—writing, teaching, special projects, love—as if it’s her last chance to experience it. “It’s only now that I feel one notch more confident about my ability to recreate another opportunity—[but] not so much the success part, which I always feel like I have to earn,” she says. “I’m working on it. [There’s] still time.”

On this episode, Millman describes her quest to feel comfortable in her own skin, talking with Spencer about the benefits of being a good listener, branding and marketing as ways to manufacture meaning, and why she doesn’t want to peak until the very end of her life.


Millman describes her experience of the Covid-19 pandemic and the work she has made during and partly in response to it, including projects with TED, NYCxDesign, and RAND Art + Data.

Millman discusses her podcast, Design Matters, and how it has influenced her confidence, interview skills, and forthcoming book, Why Design Matters (HarperCollins).

Millman recalls her tumultuous upbringing, and describes how music and musical theater provided a means for self-expression and for becoming part of something bigger than herself.

Millman talks about her career in branding and design, and how she came to redesign the logo for New York’s Hot 97 hip-hop radio station.

Millman speaks about reclaiming her creativity after decades of chasing success. She also describes a formative conversation with musician David Lee Roth, and the joyful suprise that has been her relationship with writer and author Roxane Gay.

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SPENCER BAILEY: Hi, Debbie. Welcome to Time Sensitive. Thanks for coming in today.

DEBBIE MILLMAN: My absolute pleasure. Thank you.

SB: To start, I think it’s worth mentioning that we had originally scheduled this interview to take place March 23, 2020.

DM: Wow. That’s incredible. My brother’s birthday. That’s amazing. I didn’t realize that.

SB: And, of course, basically, two weeks into lockdown. How have you been thinking about this particular period of time, this past eighteen months? How has it been for you?

DM: I would say it’s a best of times, worst of times scenario because⁠—well, worst of times, we kind of know. Best of times, for me, I got married. I got married during the pandemic. I was supposed to get married much more formally, with a much bigger audience on 10/10/2020, but we know what that was like. That didn’t happen. So, my wife and I went and eloped, and got married in a little office complex in Encino, California.

SB: I heard it was on [Laughs]

DM: Which is legit, but somewhat unsophisticated. [Laughs]

SB: So you got to quarantine with your partner, Roxane Gay.

DM: Yes, I did. We at that point were engaged, but not living together. She has a house in L.A.; I have a place in New York. We were just going back and forth, but not spending  the majority of our time together. We were able to sneak away for pockets of time, but we weren’t living together officially. 

I guess March 10th, thereabouts, we started thinking about where we should hunker down. And it seemed like it made more sense to hunker down in L.A., because we’d have a car and a bit more sky, a bit more land. And so I flew to L.A. that Saturday, I guess it was March 15, something like that. I’ll never forget her saying, “Pack for two weeks,” as if we thought that’s what it was going to be, and that’s all I did pack for. So, I ended up getting a lot of underwear from Target in the ensuing weeks, and ended up spending six months there. Then came back to New York for a little while, went back to L.A. for most of the rest of the year. And now back in New York, because I’m back to teaching in person [at the School of Visual Arts], which started two days ago. 

But quarantine, we were lucky. We both remained healthy, still are. A lot of people at the beginning were very cautiously inquiring how we were getting along, because this was our first experience living together. And it was twenty-four/seven. And we were like, Oh, it’s great. And it was, and it has been. We got lucky, we really did.

SB: You’re both incredibly synchronous, I guess, in the sense of your creativity and your output. How was that, being in such close quarters?

DM: It’s actually fine. We parallel work. We both seem to like to work with a soundtrack of Law & Order: SVU reruns in the background—

SB: [Laughs] Dun-dun.

DM: Or HGTV. I particularly like the show [Home Town]. I find the couple that does that’s just adorable. We now have a puppy, and so we’ve been spending a lot of time with him. And that was a good way for us to be able to train him effectively, with all that face time together with him. She’s in New York with me now, and we’ll go back to L.A. at some point, but not exactly sure when.

SB: Tell me about some of the projects you worked on during the pandemic. One I wanted to bring up was this “Together Apart” poster and signage that you did for Times Square Arts, Poster House, Print magazine, and For Freedoms.

DM: Yes. That was a really important project to me at the time. There were a couple of projects that I did very early on in Covid that were either New York–centric or Covid-centric, and both felt really important and necessary to do. It was really quite extraordinary seeing photos of the “Together Apart” art that I created on all the billboards in Times Square. I mean, that was surreal, especially because I am a native New Yorker. This time away from New York was the longest I’ve ever been away from New York in my entire life. As I’m about to turn sixty, that’s a long time. 

Initially, I was really homesick. So doing the projects that I did—I did a project for TED, which was also one of the pieces that I did that was about New York. I did something for NYCxDesign that felt really important. The TV shows that I was on first aired—New York by Design [and] America by Design, it’s gotten bigger—but also they aired while we were in quarantine, so it was nice to relive those moments, being back on the streets of New York.

SB: I’m trying to picture a young child Debbie Millman, seeing her artwork on display in Times Square.

DM: Surreal,. Absolutely surreal.

SB: Another project that you’ve been involved with that was announced in June this year is RAND Art + Data

DM: Yes!

SB: I was wondering if you could talk about that. It’s a collaborative artist residency program.

DM: I’m working with RAND, which is a think tank, the RAND Corporation. I was invited to participate in this by my former colleague at Sterling Brands and dear, dear friend Dee Dee Gordon. Dee Dee first came to fame, oh gosh, I want to say twenty years ago, in Malcolm Gladwell’s book The Tipping Point. She was the trend hunter, the coolhunter. Rumor has it that she was the vision that William Gibson had for his protagonist in the really incredible book [Pattern Recognition] that features his character Cayce Pollard. That’s when she first is introduced. 

That’s something that I’m also really excited about, just in thinking about her history and her ability to understand trends and understand data. She invited me to be part of this project with RAND, so I co-curated this with her. It launched three months ago with the first artist, Giorgia Lupi. And we’re now about to launch our second artist, Morcos and Jonathan Key from Morcos Key.

SB: That’s a project really about challenging how we analyze data, in some ways, or present data?

DM: Well, RAND presents and produces and publishes really extraordinary research reports that are very heavy on data, and not so much on the visual.

SB: Creatively presenting the data.

DM: Exactly. It’s very scientific, it’s very official, it’s very statistically significant. They asked us to help begin to visualize this body of data that they have, in a way to introduce the idea of what they do to a whole new generation of people that are much more visually oriented

I became aware of Giorgia’s work many years ago when she [co-authored] a book called Dear Data. Giorgia has really been on the forefront of humanizing data. We were really excited to be able to work with her because of the idea of humanizing the data that RAND publishes, in a way that makes it not only just more interesting for people to read, but also more accessible. They have so much important information to be able to share, and to share it in a way that more people can understand it, is what’s so exciting to me. The idea of being able to really understand income inequity, or to be able to understand the ramifications of mental illness—these things are so important to me. So the idea that people can look at that data, in a way, and almost understand it telegraphically is pretty revolutionary.

SB: What was it like teaching during this period for you?

DM: Oh, my god. Initially…. Well, let me back up one moment and say, change for me has always been historically difficult. I’m not one of those people that is presented with a new way of living, operating, existing, and is immediately excited by the possibilities. There are some people that are like that. They’re like, “Whoa, change! Awesome!” I’m a very fixed personality. I love ritual. I love doing not necessarily the same thing every day, but knowing what my day and what my week and month holds. And so the idea that, within literally forty-eight hours, I was going to have to go from teaching in-person to a—[the Master’s in Branding program I chair] is a high-intensity program, ten and-a-half months, five days a week—to a remote experience with Slack, Canvas, and Zoom. It was projectile tears, really. 

It took me about a month to settle into a new mode of existing, because I was so hands-on with my students, hands-on with my faculty, hands-on with my podcast, very engaged with people on a day-to-day basis—and suddenly was only able to see them in a tiny square on a tiny laptop. It was only two or three months into the pandemic that Roxane suggested I get a bigger screen. And I thought that that maybe was a good idea, but I was still so tied to my existing laptop, my existing shortcuts, my existing keyboard, that I was even reluctant to do that. [Laughs]

SB: This fall you’re publishing a book, Why Design Matters, sixteen years after you started Design Matters, which initially was on the VoiceAmerica [Business] Network, with each episode airing every Friday via telephone modem in your office in the Empire State Building. Amazing.

DM: Yes, you have done your research. Sir, you have done your research.

SB: Sixteen years. Sixteen years! You’ve interviewed more than four hundred people. What does that period of time mean for you? How do you think about it now, the trajectory of this podcast? And how do you hope, in some way, this book is encapsulating the conversations that you’ve had?

DM: That’s such a big question, and something I’ve been pondering for the last two-plus years that I’ve been working on this book. In many ways, it is a monograph of the show, and the work that I’ve done on the show. There are so many different levels and layers to deconstruct here. Because, on the one hand, it’s a journey of evolution at hopefully getting better at something that I was really terrible at at the beginning. I had a lot of passion for it, I had a lot of zeal, but not a lot of talent. That took time to manifest, and develop, and nurture. So there’s that aspect of it. 

Then there’s just the notion of developing an idea. The show has always been called Design Matters, but at the beginning it was very much a show about designers talking about design. So it was very much an inside baseball, niche podcast. Over the years, I would say it wasn’t until about the ten-year mark, that I started to really understand what I was trying to do, and then realize that what I was much more interested in investigating and analyzing was the arc of a person’s creative life. How do they become who they are? It really didn’t matter whether a person was a designer as long as they were a person with creative passion. So it could be even a business person or a scientist, but the way that they approach their life’s work was very much as a creative engagement. I’ve interviewed performers, musicians, playwrights, authors, scientists, biologists, Nobel Prize winners. And really my deep fascination is to understand how people create their lives. How do they make something out of nothing over the course of their life? I find that endlessly fascinating.

SB: One throughline that you’ve talked about in interviews before, but I did want to bring up because I think it’s fascinating and it’s something that happens on your podcast, is this nexus around the notions of confidence and courage. I’m thinking in particular of conversations you had with both late, great designers, Massimo Vignelli and Milton Glaser, but others, too, this notion of confidence. And so I wanted to ask, how has Design Matters influenced or impacted your own personal confidence?

DM: That’s a great question. And I love great questions, because I know it’s hard to construct them. 

I’d really like to be motivational today and say, “It’s incredibly increased!” But it really depends on the day, and depends on my mood. I very much am a person that metabolizes accomplishment, for good and bad. I’m always looking to create more, better, bigger. I think that comes from a real deep lack of confidence, and that still exists. 

I think you can both hold, in your being, a lack of confidence in general, as well as an understanding that you might be good at one thing, or two things. And that’s sort of how I feel about Design Matters. I mean, Design Matters is by no means the biggest, most important, most successful podcast on the internet, not even by a long shot. It’s just something that I know resonates with people because of the responses that I get from listeners. The one thing that I do feel strongly is that I can research. I can do my research. I have good research chops. That’s the only reason I think that I can conduct a good interview, because I’m so committed to trying to understand the psyche of my guests. 

In some ways, that helps fuel my conversational confidence that I will spend weeks working on an episode, just so that I feel that anywhere my guest might go in that conversation, I can follow. I think conducting a good podcast, a good conversation, and a good interview, means that you really, in many ways, need to let the guest lead. But you absolutely have to know how to follow. You’re kind of like Ginger Rogers: You have to do everything that Fred Astaire does, but backwards. [Laughs]

SB: It’s so funny. I’ve always used the drummer analogy, because in my other life I’m actually a drummer, or I play drums, anyway. So this notion of interviewer as drummer I like, because you lay the beat, but you really let the other people kind of…. But if you mess up, everyone else is going to fall off the rails, too.

DM: Yeah, absolutely. I say that a good interview is like playing a good game of billiards. You have to be able to not only get one billiard ball into the pocket; you also really want to leave the rest of the billiard balls on the table in position to continue to get the billiard balls in more pockets. It’s not like tennis, where you’re volleying back and forth. You really want to be able to ask a question, and wherever that guest goes, you can follow. That really does require having enough knowledge about their body of work, and their origin story, and their journey to be able to pick up wherever they might take you. 

That’s also I think what makes it really exciting, because you have to really listen. And that was a lesson I learned—well, let me put it another way, that was a lesson I became aware of on my second episode, way back in 2005. It’s taken me a long time to learn how to do it, but I was aware that I had to on episode two, when Cheryl Swanson, my guest, replied, when I asked her how she thought I did as an interviewer, she said, “Well, you might want to listen to my answers before you cue up the next question.” [Laughs] I was like, “Yeah. I think so.”

SB: I think listening is one of your great skills, and one of the reasons your podcast resonates so widely. I’m wondering, from your perspective, what is the great impact of listening? How important culturally could listening become? Because I think currently, we live in an age where people are doing a lot of talking and not a lot of listening. What do you think could be learned if we spent more time listening, or at least a bit more time listening?

DM: I think you’re able to connect in a more meaningful way. One of the things that I search for, and also try to teach to my students, and it’s really something I aspire to in any conversation—it’s not just in interviews—is mutuality. That sense that you know that I know that you know that I know that we’re connecting—that’s a palpable feeling. I’m feeling it right this minute with you. If you don’t get to that, then you’re missing what it really feels like to be connected to that person. I think you can only do that with listening. 

“I Stress Because I Give a Fuck” (2015). (Courtesy Debbie Millman)

For me, it’s also about looking. I’m very dependent on visual cues, which was also why it was very hard, early on in Covid, to move the show to Zoom, because I love the intimacy of watching someone talk. It’s not just listening, but also watching their body language, their hand gestures, their eyes. All that to me is so rich with information and cues, and just telegraphs so much about a person. 

So that’s also something you have to do concurrently, as well as be aware of where you’re going next with questions. Because I do, like you, have paper in front of me when I’m talking. I’m not just winging it. My wife is a winger. She can talk to anybody about anything with very little preparation. That’s how smart she is. For me, I like to have it all there. Surprise, surprise—I like that control. So I also have to be aware of where I might want to be in that script, loosely. It’s a script that I prepare in advance.

SB: Sounds about right. [Laughter]

DM: Exactly. You know that I know that you know that I know that we get this.

SB: There’s this line by Maria Popova, the creator of the website Brain Pickings, that she writes in the—it’s sort of an afterword in your Why Design Matters book. And I wanted to read it, because I found this line astoundingly beautiful and relevant to the subject of time.

DM: Thank you. She’s a wonderful writer.

SB: “An interview petrifies us in time then lives on forever, the thoughts of bygone selves quoted back to us across the eons of our personal evolution—a strange and decomposing taxidermy diorama of life that is no longer living.”

DM: Yeah.

SB: What a way to think about an interview.

DM: Whew. Goosebumps. [Laughs] I was talking to Roman Mars yesterday, and we were talking about doing a little interview, Q&A kind of thingy, and we were riffing on what it could possibly be. And I said, “Well, why don’t we revisit my Design Matters episode with you, from like ten years ago?” And he was like, “Nooo!” [Laughter

What’s also interesting—I took an archetype test. I’m preparing for an interview with Jonathan Fields, who has a book coming out called Sparked. It’s about these archetypes that he’s created. And so, of course, I took the test, and know what my archetype is from his analysis. One of the things that he included in the analysis of this particular kind of person is the notion that you don’t like to revisit things. You don’t like to, once you’ve made something, revisit the making. I realized that that is absolutely true, that once I’ve done an interview, it’s done, and it is petrified in that way. I don’t even like to listen to my voice.

SB: [Nods in agreement]

DM: You, either? Yeah. I don’t like to have to go through the experience again, because it was this one moment in time that felt perfect as is. There’s no need for a repeat. [Laughs]

SB: Yeah. Well, that was something that I was curious about in the making of the book. Did you listen back to some of those episodes? Did you cringe? Did you laugh? Did you cry?

DM: All of the above. I didn’t listen, though. What I did was I had them all transcribed. I had about, I would say, half of my episodes transcribed. I’ve done about four hundred and fifty or so at this point. I had about two hundred and something transcribed, and then I read them all. There were moments of excruciating agony, like, How is it possible that anybody still listens to this show after reviewing the transcripts? But there were also some surprises and things that I was really happy about finding, and understanding the growth, and just seeing the tangible evidence of one’s improvement, however slight, but it’s there. 

It was interesting having to decide what kinds of interviews I wanted to have in the book, because I want this to be a book that feels timeless. Yes, those interviews are petrified, but I also want them to have some sort of emotional timbre that feels like it could be anyone at any time experiencing any thing, because it’s so universal. And so, because it was so difficult to edit how many interviews were going to be included, given the extraordinary number of guests that I’ve had, and really brilliant guests, the first cut was: Is this timeless? Does this offer something universal that anyone can pick up and read and say, “Wow, that’s what it means to be human”? It’s not so much about a specific book, or a specific play, or a specific piece of music. It’s really very much about an emotional experience that someone has, being who they are, that other people can read and relate to.

SB: I think an interview, at its best, gets at that. And sure, it might be pegged to a book coming out or this or that, but ultimately the meat of the interview is that, it’s the human part. When you’re listening to Terry Gross, when you’re listening to Krista Tippett, their interviews are the best when they get to that essential.

DM: I have a funny story about Krista Tippett. Krista Tippett, before Covid, was the last interview that I did studio-to-studio

SB: Oh.

DM: Every other interview I’ve done since Krista, and the majority of my interviews, were face-to-face. But after Krista, I made a decision that I was no longer doing any interviews studio-to-studio—unlike Terry Gross, who doesn’t like to look at people when she does her interviews— 

SB: Yeah. Fascinating. 

DM: I have to. I had decided at that point—I’ve really passed up some incredible opportunities. I still kind of kick myself that I let some of those go, given how moving to Zoom has been okay and didn’t kill me. But after Krista, I decided that I was no longer doing studio-to-studio. And it is because, when Krista and I were talking…. 

We were ostensibly there to talk about her book Becoming Wise, but of course we talked about her whole life. One thing I was particularly interested in at that time was her experience with depression. I had recently gone through a period of depression, she had gone through a period of depression, and so we talked about that. It was a very heartfelt, very honest conversation. At the end of the interview, I got my show notes from my producer, and he said, “I really wish you would have asked her how she came out of her depression.” And I’m like, “What?! I didn’t ask her how she—oh, my god!” And I knew, if I had been looking at her face-to-face, that I would have been able to pull that out. 

Fast forward several years; I am now going through my transcripts. And I have now changed, fundamentally, my rules about how I’m conducting interviews. Only face-to-face. I’m looking at my transcript with Krista, and what do I find? “Krista, how did you come out of your depression?” And I was like [whispers], “How did Curtis miss that?” He was just not paying attention in that moment in time. But that one thing that he said to me really propelled me to consider only doing the interviews face-to-face. And because I had just started doing them via Zoom, it did give me the “confidence,” in quotes, to try it again and just be that much more careful about listening.

SB: Well, from the start, one of the things Andrew and I talked about was how important it is that every guest sits in the same chair, in the same room, and gets to experience the space, and the sound, and the feeling of being in this room.

DM: Which is a beautiful room, by the way.

SB: And hopefully comes through in the audio.

DM: It’s interesting because Tim Ferriss wrote the introduction, and he talks about what it’s like to be in my studio. Because I’ve interviewed Tim now, I don’t know, three or four or five times. And two of those times, he’s been in my studio. He talks about it in the introduction, what it’s like being in this little dark room with Debbie, this sort of intimacy that is experienced, because it was also pre-Covid. I sat very close to my guest, we’re in a very tight and enclosed room. And I do think in the same way that the airy beautiful light, the sense of cleanliness and style and beauty that exists in your studio very much reflects you. The cramped, dark, intimate studio indicates my approach to getting into somebody’s head somehow. [Laughs]

SB: With Tim, it’s clear that you guys have formed, together, a profound connection, and been equally vulnerable on each of your podcasts.

DM: Tim is my brother from another mother.

SB: [Laughs] So, this fall you’re turning 60. What does this particular milestone mean to you? I know you’ve talked about how you’re much more aware of time now.

DM: Yeah, I am. I didn’t really start thinking about age and mortality at all until I was 49. And when I turned 50, it was…. I think “crisis” is probably too strong a word, but definitely a comeuppance. What am I doing with my life? Why am I doing these things this way? And by 55, I had radically changed my life. Radically. I came out, I sold my business. Everything about my life was different: where I lived, where I worked, how I loved, everything. 

Now, it’s another decade. The “If not now, when?” mantra is constant. And having gone through, or in the midst of, this pandemic, seeing really how fragile life is—we recently had a death in our family, somebody very important to us, not Covid-related but tragic. And that constant clarion call of, What do we make of our lives? What do we make of ourselves? What do we leave behind? Those, to me, are the biggest and most pressing questions of my life right now.

SB: I want to go back to the beginning, but before we do, I did want to bring up this Ezra Pound quote that you finish your book Look Both Ways with: “We do not know the past in chronological sequence. It may be convenient to lay it out [anesthetized] on the table with dates pasted on here and there, but what we know we know by ripples and spirals eddying out from us and from our own time.” It’s a great quote on time, one I hadn’t come across before. And it reminds me, sort of thinking about Robert Smithson’s “Spiral Jetty,” and just thinking about time as a coil, not as a straight line.

DM: Have you seen the movie Arrival?

SB: I haven’t.

DM: [Gasps] Oh, I am so about to change your life.

SB: [Laughs]

DM: That is a magnificent movie, and it’s about the circularity of time, or the possibility that time is circular. And it’s really a beautiful, beautiful movie. I can watch that movie over and over, and still find new things in it. It’s a remarkable movie, and I think you’ll love it. If you love thinking about time, and analyzing the nature of the way time moves, you will love this movie.

SB: I guess I know what I’m doing this weekend.

DM: [Laughs] You have to tell me what you think.

SB: Okay. Well, I wanted to bring that quote up just because I think, even the way this conversation is going to go, it’s not a linear, straight line. And your life certainly hasn’t been. Although, there are all these interesting parallels from your youth to your adulthood, and the way your life has connected. 

Let’s go back to your youth. You’re a native New Yorker, born in Brooklyn. You grew up in Howard Beach, Queens, lived on Staten Island. Then, when your parents divorced, you moved with your mom to Long Island. Your father was a pharmacist; your mother was a seamstress and a painter. Now that I’ve laid all that out, tell me about your relationship with your parents and just growing up, your childhood? I know you’ve described it [in Look Both Ways] as a “D.I.Y. upbringing.”

DM: And the older I get, the more amazed [I am] that I came out of it even remotely intact. It was … turbulent. My parents, between them, have been married seven or eight times, I think. My father died six years ago. They were both really complicated people, and were way too young to have children. My mother was 18, my father was 21. They were babies, and babies shouldn’t have babies. They were so busy trying to figure out who they were, they didn’t know how to take care of kids. 

So my brother and I—my brother’s two and a half years younger than I am, we’re very close. We’ve only become close in the last ten or so years. There were years where we were estranged, just because everybody in my family was estranged. Everyone. There is no one in my family, no one, that speaks to my mother. My mother has been married four times, has adopted children from other marriages, so altogether, six. No one speaks to her. I’m the only one that has even the remote kind of contact with her. It’s very infrequent because she became a Trumper, she’s a born-again Jew for Jesus. She thought Trump was the prophecy, doesn’t want to wear a mask, because she thinks that if we were meant to wear masks, we’d be born with them. When I told that to my shrink, she very aptly replied without blinking, “What about clothes?” So that’s hard for me. Super hard for me. She also doesn’t believe in, or doesn’t think that, being gay is “normal,” I guess, is the word she would use. So that’s all really hard for me. And I really tried to see what she sees. When it got to the Trump part, I couldn’t anymore. So that was really, really hard. Hearing her say, “Trump is the prophecy,” I was like, “No, he’s not, Mom. No, he’s not.”

SB: As a kid, in real time, how did you deal with this difficult, traumatic thing in front of you?

DM: I don’t think you understand when you’re a little person that your parents are clinically, mentally ill. Which they both were. You worship your parents. You want them to love you. My father was extremely, extremely turbulent, very volatile. I didn’t know when he was going to be in a good mood or a bad mood. And so I was always on eggshells, and always afraid. And that’s hard, to live like that. Then, as I got older, when I was 10, after my parents got divorced, my mother remarried. This part, people that might’ve listened to my interview with Tim [Ferriss] know. She married a man who sexually, physically, and emotionally abused me for years. And had to figure out how to put the pieces back together as an adult. And now feel that that understanding of what I went through has helped me in my work with the Joyful Heart Foundation, and trying to eradicate domestic violence, sexual assault, and child abuse in our culture, on our planet. That’s something I’m very committed to doing. 

Even in the work we’re doing now in eradicating the rape kit backlog is making a huge difference in people understanding [that] how culture responds to sexual violence is indicative of how culture responds to women. That work is really important to me, and I’m proud of that work. It’s really, in many ways, made my life make sense, and that’s something I first disclosed to Tim.

SB: You mentioned this period, when you were around ten or eleven years old, and I understand you also had a sort of speech dysfunction.

DM: I don’t know if I would go quite as far as that. In thinking about it more recently, I think it might’ve been more of a reaction to what I was experiencing. It only lasted about a year. And it wasn’t so much an impediment; it was more of a psychological disorder. I suddenly did not understand the validity of reality, if that makes sense. So whenever anybody would ask me, for example, an innocuous question like, “How are you?” I wouldn’t know what to say. So I would say, and maybe it was an accurate thing, but it sounded crazy—I would say, “Well, maybe I’m okay, but maybe I’m not.” Because at any moment anything could change. If somebody would say, “Are you hungry?” I would say, “Well, maybe I am, and maybe I’m not.” So everything was maybe yes, maybe no. I couldn’t commit to anything being that moment’s accuracy. Somebody might say, “Oh, what’s the weather like in New York?” My grandmother lived in Florida. “What’s the weather like?” “Well, maybe it’s nice out, but maybe it’s not.” “Well, is the sun out, or not?” Everybody was super concerned that there was something really wrong with me.

SB: But it was just a kid who was traumatized. Recoiling, really.

DM: Yeah, it was. What’s interesting is that I’ll never forget the day that it stopped. My stepfather, the mean man who abused me—he had two children from his previous marriage—put my brother and I, and his two children through this nightly torture, which he called “inspection.” Every night, he would inspect our rooms to make sure that they were spick-and-span. Everything had to be in order. 

One day he did an inspection on my room, and somehow, unbeknownst to me, a skirt had fallen off a hanger in my closet, and was laying on the floor of my closet in a little heap. He opened the door to my closet and saw the skirt there. And he was furious with me: “Why is the skirt on the floor?” And I said, “I don’t know, I didn’t do it. It must have fallen by itself.” And my mother and my stepfather were furious with me. I remember, as if it were yesterday, them saying, “How can you be so sure? You can’t even be sure if it’s raining out. You’re telling us that for sure this was on the hanger when you closed her closet?” And I was like, “Yes.”


SB: Gravity.

DM: Right?

SB: When I was reading about your childhood, and also listening to you describe it on a couple of different podcasts, I was fascinated to learn about how you created these markers of time during those years—visual markers of time. Like when your mom told you and your brother that she was divorcing your father, she took you to go see Hello, Dolly!. And so you have this image from Hello, Dolly! and the beets in the film.

DM: I’ve just begun to start enjoying beets, by the way. 

SB: Amazing.

DM: When I saw Bette Midler on Broadway, and that line came up in the play, I was sitting, I think, in the second row. I was weeping, just weeping, hearing it again, and having it become a new marker.

SB: Music seems to be a big part of your life, not just your childhood, but your life, in terms of marking time. Could you talk about this aural fixation, and how sound and music relate to how you relate to particular moments in time in your life?

DM: I think I use music as a marker. I get so involved in whatever new music comes out that I’m immersed in, that it becomes almost synchronous to the time. Music moves me so deeply that that first listen, or that first experience, will become embedded in my neural pathways, I think. And because I’m a person that, when I love something new, I’ll listen to it over and over and over again until it becomes part of my DNA, that when I then move on to something else, but then hear it again, or play it again, it brings me back to that moment very viscerally. And I kind of love that. I mean, that really is a very circular way of thinking about time, because it literally does bring me back to that moment.  

I can associate it with so many things. It’s not just the air, or the time, or the place. It’s what I was wearing, or what I was eating. There are so many different connections to it.

SB: I know in high school you were interested in musical theater. Were you actually playing any instruments or just singing?

DM: Those were the dark years. There really wasn’t any opportunity to take piano lessons or guitar lessons. I tried to teach myself, very rudimentarily. So I can play Neil Young chords on a guitar, and that’s about it. And I can play “Chopsticks,” and “Doe, a Deer,” and “Heart and Soul” on the piano. But I did very much want to work in musical theater, and was in all of the school plays, and sang, and danced, and did everything that one does when you’re in high school, in Godspell. I look back at those days, at those moments, thinking, That saved my life. That ability to express myself, to feel part of something bigger than I was, to be able to get out of the house, to be able to stay out of the house every day for play rehearsal. All of those things were so important to who I am today, whether or not I’m an actual musical theater person. I still go to musical theater a lot.

SB: What sort of impact did having your brother around have on you?

DM: My brother only lived with us until he was 13. When he was 13, he gave my mother an ultimatum: either her boyfriend, who she was with at the time—she didn’t ever marry him, but he was in our lives for a very long time—either he goes, or my brother was going to go live with my father. My mother said she couldn’t make that decision, so my brother went to live with my father. His relationship with my mother never recovered from that. There were a few attempts, but [it] never recovered. 

My dad unfortunately—I still don’t fully understand why, but he was only able to have compartmentalized relationships with his kids, one at a time, or two at a time. He got remarried and had two more boys, so I have three brothers. There was never a time in our lives, ever, ever, where he was talking to all of us. When he died, he wasn’t talking to three of us, by his decision. So in the time that my brother was an adolescent, and then a teenager growing up, and I was in my twenties, as we grew up, we took turns being in touch with our dad. He couldn’t ever have a relationship with both of us at the same time, which made it very difficult for us to have relationships at the same time, because he didn’t want us to be in relationship with the other that he wasn’t in relationship with. Does that make sense? 

SB: Yeah.

DM: So it was really, really turbulent. It really wasn’t until my brother decided he couldn’t live like this anymore, and pulled himself out of the relationship with my dad—and I decided I wasn’t going to sacrifice my relationship with my brother, and my father would just have to manage his own emotions, knowing that we were in contact despite the fact that they weren’t—that we were able to solidify, finally, a really deep and strong relationship. Now that he has children, that’s been a tremendous constant in all of our lives, [and] my being a constant in their lives, which is really important to us all.

SB: I wanted to transition a little bit, not fast-forwarding too much, to your career in branding and design. I found it fascinating, when researching, that you engaged in branding and graphics quite early on. Your dad had a pharmacy. And in your book Brand Thinking, you note that your life has been shaped by brands. When did the notion of a brand enter your psychology? And then when did you decide, Oh, this is actually a career?

DM: I would say that brands first entered my psychology when I became obsessed with Goody barrettes when I was a little girl. My father had a spinning stand in his pharmacy filled with the barrettes, headbands, ponytail holders. And I just thought that was the most magical thing in the world. I loved collecting them. I actually once stole one from a friend, which I write about in Look Both Ways, which to my dying day will be a shame spiral. But I suddenly became aware of things outside of me that could enhance me by the virtue of their proximity. Barrettes could make me feel prettier. 

When I got to high school, all the cool kids were wearing Levi’s jeans and Lacoste polo shirts. I thought, Well, if I have that same uniform, maybe I’ll be accepted, and a cool kid, too. Suddenly, these external elements could camouflage a very insecure spirit. Taking those objects on, or in, was a way for me to in that moment—because I know now what’s really happening; it was a fairly fleeting experience—but in the moment, I would feel better about myself. That’s when I began to—nascently, not consciously—realize the power that brands have over people, because they had so much power over my psyche and my own sense of self. But I didn’t know that that was a career, nor did I have any understanding of the psychology behind anything I’m saying now. I just knew I felt better. [Laughs] I felt a little bit cooler when I was wearing Levi’s. 

My first decade in my professional career was as a designer. I ended up in branding quite by accident, having failed out of every role that one could have in design agencies between my twenties and early thirties. I ended up a salesperson at a branding consultancy as a Hail Mary to be able to pay my rent. At that point, because I was doing business development and didn’t know how much I knew about the psychology of branding, I suddenly was, “Oh, my God. I have this magic toolbox of things that I know and feel and could experience and share.” And then I found my calling professionally.

SB: That time in the pharmacy must have been so formative.

DM: Oh yeah. I mean, I worked at my dad’s pharmacy…. When I was in college, I would hitchhike—I know, don’t even. I would hitchhike…. There you have it, my father and my relationship in a nutshell: He wanted me to go work for him on the weekends, and I’d hitchhiked to his store, on the highway, in the eighties. [Laughter] I would hitchhike and get to his store, and work on the weekends to help him, and also make a few bucks. 

That experience was probably better than college in terms of understanding branding, and understanding why people choose the things they do, and how they do, and how they spend money on commodities. And how they choose things that might embarrass them, or they might need to feel better, or the relationship people have with pharmaceuticals, and at the time, cigarettes—everything that he sold in his store. Suddenly I was touching everything, and serving, and making change, and doing everything that one does to serve someone buying something. That’s an education.

SB: Yeah, distilling the paradox of choice

DM: Absolutely.

SB: When it comes to time, particularly related to branding, I did want to talk quickly about this long-sweep evolution of branding, this notion of, as you describe it in a TED Talk, like, “Lascaux to Facebook.” I don’t think most people realize how nascent, in many ways, the notion of how we perceive a modern-day brand is so young. I mean, as you’ve pointed out, January 1, 1876, was the advent of the Trademarks Registration Act. It’s not even two hundred years. How do you think about brand in relationship to time and speed and contemporary society, and the notion of how we perceive and understand a brand, or branding, today?

DM: Brands are symbols that signify whatever we imbue in them, whatever we project in them. And one of the examples that I cite in the TED Talk is something that we all perceive horrifically now, which is the swastika. Hitler appropriated the swastika. The word swastika comes from the Sanskrit word svastika, which stands for good luck and fortune. And Hitler appropriated that mark. Prior to his doing that, that mark was on material that the Boy Scouts created. It was road signs. It was on good luck poker chips. It was on playing cards. It was on cookies. Coca-Cola used to make a bottle opener

We project characteristics into symbols, and then, through consensus, agree on what those symbols mean. So we now all agree that that mark, the swastika, is a mark of cruelty and evil. But a hundred years ago, it was considered a mark of good luck, only because of what we projected and associated with it. If you look at the Nike swoosh, the Nike swoosh upside down is the Newport cigarettes logo. It’s also very close in appearance to the Capital One logo. It’s not the mark so much; it’s the marketing. And the marketing is the way in which we manufacture meaning. We’ve done that since the beginning of time. 

Some of our oldest symbols, as a species, are religious symbols. And those religious symbols are really no different. You can’t necessarily go into a supermarket and buy that symbol, but you can certainly go into a place of worship, and experience that symbol in the same way you might go into an Apple store and experience the Apple logo. The tenets are very, very similar. This is a way for us to organize reality, and organize information. It allows us to be able to telegraphically communicate. It allows us to telegraphically understand “safe” or “unsafe.” And it allows us to communicate very effectively without having to speak the same language, or understand the same conditions.

SB: I was fascinated to learn, also, that the word brand is derived from the old Norse word brandr, which means to burn by fire.

DM: To mark or destroy by fire, yeah. Cattle ranchers began to use that word to signify the mark by fire, which is originally how cattle were branded. It was only later in time, or more recently, that—well, first pine tar was used, then fire, to mark the cattle. And now you’ll often see the plastic hooks that are attached to cattle ears, so that if they run away from the pack [they] can be more easily found.

SB: I mean, the notion of burning, and relationship to branding, is fascinating on so many levels.

DM: So many levels.

SB: When you were twelve, you created a magazine called Debutante. [Laughs]

DM: With my friend Debbie Karp. I still maintain that that is a great name for a magazine, and I believe it’s still available for anyone that wants it.

SB: And you were later editor of the arts and feature section of the SUNY Albany newspaper, where you were an English major. Did you have literary aspirations, journalistic aspirations? And when did graphic design and branding come into the picture for you? Was it an outgrowth of the work you were doing at the newspaper?

DM: Yes. I majored in English. I minored in Russian literature. I always joke now that I have a college degree in reading. Very, very useful. When I was a senior, I was the arts and features editor of the student newspaper, and as part of the duties of the editor, you also had to put the paper together, which, in the terms of today, we’d say you have to design it. And at the time it was really basic layout and paste up, but I fell madly in love with doing it, and really enjoyed doing that more than anything else. 

So when I graduated, I really had two different skill sets. I had an editorial skill set that I had developed while being editor of the paper, but I also had a very limited graphic design skill set, where I could do basic layout and paste up on drafting tables. My very first job out of college was doing that. I was sort of a traffic girl between the editorial department and the art department at a cable magazine [Cable View], which was all the rage back then. This was 1983. So I would work spec’ing type, and I would be editing, and fitting little copy descriptions into boxes with little pictures of Dustin Hoffman and Jessica Lange in Tootsie, which was a big movie at that time, and things like that.

SB: One of your early jobs I wanted to bring up was as the off-air creative director of Hot 97, which you haven’t talked a lot about. I just wanted to hear, how did this job come about? What was that experience like, working on the identity and graphics for what was the first-ever hip-hop station?

DM: It was an amazing, amazing experience. My last job at a graphic design studio, before I went into branding, was at a company called Frankfurt Balkind. Actually, when I was there, it was called Frankfurt Gips Balkind. This was a job that really pushed me out of graphic design. That was what led to my Hail Mary into branding, and really more as a sales person than a creative person. When I was at Frankfurt Gips Balkind, one of my prior clients at an agency that I’d been at before Frankfurt Gips Balkind called me, and told me that his wife, Helene Gold, worked at a radio station, and they were looking to do a redesign and rebrand. And could they come into Frankfurt Gips Balkind, who was very well known for doing entertainment design, to see if perhaps Frankfurt Gips Balkind can do the redesign? The entire marketing team at Hot 97 came in, led by a phenomenal woman named Judy Ellis, and her right-hand person, who is named Rocco Macri—neither one works there now. They came in, and the head of accounts, Harriet Balkind, who was the wife of Aubrey Balkind, one of the partners—Aubrey’s wife Harriet and Judy didn’t get along. Like, you could see that it was one of those hate-at-first-sight moments. So I was crestfallen, because I would’ve loved to have worked with Hot 97, and thought it was such a cool project. They didn’t really think so at Frankfurt Gips Balkind, and nothing happened. 

Shortly thereafter, I left Frankfurt Gips Balkind, and Steve Gold, my friend, whose wife worked at Hot 97, called me again, and said, “I see you’ve left. Do you want to do this on your own?” I was like, “Hell, yeah.” And I did, for twelve years. For twelve years, I was the off-staff creative director at Hot 97, worked with Rocco Macri, and Johan Vipper, and Judy, of course, Judy Ellis, to launch the world’s first hip-hop radio station. And it was an extraordinary experience.

SB: And such a definitive touchstone of New York.

DM: Absolutely. And Angie Martinez, who became a very, very popular D.J. on Hot 97, at the time was Judy Ellis’s secretary. We had no money to do anything, and we were looking for models to help launch the radio station. So we did an open call on the radio. Steve Gold had a lot of connections in the club world. I think we did an open call at the Palladium, or maybe it was Area…. Tunnel…. I don’t remember one of the big clubs at the time. We did an open call, we got listeners involved. And we did a photo shoot with the listeners, the actual listeners of Hot 97, that really portrayed the demographic that we were going after. That’s how the whole thing happened. Angie, Judy’s secretary, was in that first set of ads, and then slowly but surely, she started doing some D.J. work on the radio, and then ended up basically being their most popular D.J. for years and years and years. 

When that ad campaign first launched it, there was no such thing as going viral at the time, but it went viral. It ended up on the cover of New York Newsday, saying, “Sexy Buses, Sexy Subways,” because they were all bus and subway ads. They were all these really sexy hip-hop people, and no one knew what to make of it. The whole city was in an uproar. It was phenomenal.

SB: Were you involved in the identity?

DM: I worked with Cey Adams. There was an identity that existed when we all started. Cey Adams, the remarkable designer and graffiti artist, did that first redesign. And then many years later, I worked on the second redesign at Sterling Brands, because then, full circle, when I went to Sterling, I brought Hot 97 with me, and did the work there, with some remarkable designers at Sterling.

SB: So you have twenty years at Sterling, you have this really incredible run there. You worked on teams that created identities for 7Up, Tropicana, Burger King, Twizzlers. You did branding and packaging for all kinds of snacks and pharmaceuticals, again, full circle. And you’ve described yourself during this period [on the podcast Hello Monday with Jessi Hempel] as a “success-aholic.”

DM: Did I?

SB: Yeah.

DM: That is a good word.

SB: Sort of this idea, I guess, that you started to feel like, as much work as you were doing, there was still a creative soul within you that was dying. You’re making all this work, and then what? How did you find your way back to fulfilling your creative urges?

DM: After Frankfort Balkind, I went to a company called the Schecter Group, which, while I was there, was subsumed by Interbrand. And I worked at Interbrand for a very short time. When I was at the Schecter Group, and we were folded into Interbrand by Omnicom, most of the staff left en masse. At one point I was one of maybe three or four or five people, from the original staff of the Schecter Group, working at Interbrand. It was a really strange political time in the agency given this merging of two cultures, two staffs, just very difficult. And I was used to difficult, but this was on a whole other level because of the public nature of the company—it was a publicly traded company. It was on a completely different level. 

I ended up calling a headhunter, Roz Goldfarb, who connected me to Sterling. I remember my boss at the time telling me that I was going on a suicide mission with my career, going to Sterling, because Sterling was just coming out of bankruptcy. But I was so desperate—I needed to make money, I needed to take care of myself—that I needed to find a secure position. I got hired at Sterling doing business development. I was very good at it at Interbrand, and at Schecter, continued becoming even better at it. And very quickly, in a matter of eighteen months, was appointed president of the agency because of how successful I was at bringing in business. 

Here I am, thirty-three, thirty-four years old. For the first time in my life, I am professionally successful and making money. I could not believe my good fortune. Because it was so life-affirming at the time, for me to have this success, that’s all I wanted to do, I just wanted to do something I was successful at twenty-four/seven. I was so used to failing, so used to rejection, so used to strife, and here I was, bringing in the biggest accounts I’d ever worked on. I was like Michael Jordan in a zone; I just could not miss a basket. That’s all I wanted to do. It was like, Let’s just give up everything else, because this feels so good all the time. And that’s what I did, for about eight years. Within thirteen years, we were able to sell the company. So clearly I did well, and I’m so grateful for that experience. 

But at that eight-year mark, I started to realize that I was dying inside a little bit. Everything was commercial. Everything was about a return on investment. Everything was about shelf presence. Everything was about market-share position. And I was a girl that used to love to do needlepoint, and draw, and write dumb poetry, and crummy drawings of whatever. I had come a long way from that, and wanted a little bit of it back. And that’s when I started writing again, and that’s when that fateful day, when I got that cold call from Voice America: “Do I want to do a radio show?” I was like, Why not? This could be creative, and I can maybe also merge it with business, and I can kill two birds with one stone. And that’s really what I did.

SB: I want to finish on the subject of love. 

DM: Okay. 

SB: You’ve had two divorces—one in your twenties, one in your thirties—and then at 50, came out, and in 2018, at last, met Roxane Gay. If ever there were a long view on love, I think it would have to be yours. 

Tell me a bit about this journey, which—I listened to the podcast episode that Brené Brown did with Roxane and you, and she described it as a “proper rom-com.” And I have to agree. I really think that there could be a whole episode beyond what she discussed with you guys. So I just wanted to get into this. How are you thinking about your life, these different periods of time, and your long-view path to love?

DM: You could only really appreciate a long view when you’ve been alive for a long time. Given how much research you’ve done to prepare for this interview today, I’m sure you’ve heard my repeating David Lee Roth’s comment about what it means to peak. So for your listeners, I’ll share it, because it’s really one of the most profound things that I have been gifted on Design Matters. 

When I interviewed David Lee Roth, I asked him what it felt like in 1984 to be the most popular dude on the planet. 1984, I was one year living in Manhattan. I was there for the birth of MTV. I watched “Jump,” their video, four thousand three hundred sixty-eight times that first year, and knew the power that Van Halen had back in the day. That moment in the “Jump” video, when David Lee Roth and Eddie Van Halen are riffing together, and you see David’s little dimples, and they’re smiling together…. I mean, that was a moment that really solidified a generation. They were so popular. I know you’re a lot younger than me, so I know you couldn’t possibly remember what that moment was like. But Van Halen, they were the “it” band of the moment all over the world. 

I asked him what that felt like. What does it feel like? What can that possibly feel like? How could you explain what that feels like to me? And his answer really surprised me. He said, “You have to be really careful when you get to the top, the tippy top of the tallest mountain. Because when you get to that top, you’re almost always alone. It’s always cold, and there’s only one direction.” So he cautioned those in a rush to peak. In that moment, I felt seen. I was like, Okay, I don’t want to peak until the day before I die. 

So that long view—again, once you’ve lived a fairly long life, [it] suddenly feels doable. And it feels aspirable, if that’s a word, because the last thing I would like to think is, I did my best work in my twenties, or my thirties, or my forties, or even my fifties. I love making things so much, and I love being in a place where I can intellectually, physically, emotionally, make something. That’s when I’m happiest. And the idea that somehow that would dissipate over time is terrifying to me. So having the long game in mind, and not rushing to accomplish everything anymore, but taking those small steps, is a lot more gratifying now than it was in my twenties, when I thought it would never happen and I was doomed. 

As far as love is concerned, honestly, I have to say I just got lucky. There’s no philosophical tidbit that I could provide, other than: The year before I met Roxane, I was suffering from heartbreak. I very intentionally took myself off the market. I did not want to be involved; I didn’t want to be in a relationship. I had always been a serial monogamist and jumped from one relationship to another—oftentimes there was some slight overlap—and didn’t want to live that way anymore. For the nearly two years that I was single before Roxane, I was in a self-imposed singleness. I would not allow myself to do that, because I felt that I needed to break the pattern of depending on somebody else for my happiness, or my self-worth, or my pleasure, or anything. When Roxane finally acquiesced to going out with me, because it was quite a long campaign to get her to pay attention to me—

SB: Originally, it was asking her to come on your podcast.

DM: Yes. But when I did that, I do have to say, quite honestly, it wasn’t for seductive purposes. I was so moved by reading [Gay’s memoir] Hunger that I felt like I was reading my own diaries, and needed to connect with her about it, and kept writing her about Hunger and kept quoting the book back to her, and telling her—

SB: It was intellectual love.

DM: Yeah, it was. It absolutely was. But then, once we did start dating, I also didn’t push, because that’s how sure I was we were supposed to be together. I wanted her to find out in her own time. I never asked her for her phone number. She only wanted to communicate via email. Fine. We’ll communicate via email. If she doesn’t want to text with me, we don’t have to text. Until she wants to give me her phone number, I will be emailing her. 

And I never did that before. I was always like, How can we move it to the next level? How can we get to the next place? How can we, how can we, how can we, how can we? I was really impatient, and always pushed to solidify the relationship as fast as possible so that I would feel secure, which is not really good for a relationship. And so here, I just tried to let it unfurl in the way that I knew in my heart it would. And it did.

SB: And it sounds like—I might be wrong—but it sounds like in your career, you’ve also come to a similar place, where it’s okay to say no, it’s okay to be a little more patient with what you take on, what you decide to do.

DM: You’re smiling because I’m smiling, and that’s a work in progress. It’s still really hard for me. I remember when I got my first book deal⁠—you have How to Think Like a Great Graphic Designer in front of you. I still maintain that that’s the worst book title of any book in the history of all books. Nevertheless, the reason that that’s the title it is, even though that’s not really what the book is even about, is because I was so afraid to push back. I was so afraid to say no, because I thought if I said no I’d never ever get another book deal again. This was it, this was my only chance in life to write a book. And I was able to persuade the publisher to let me have content that was different from the title, and the title would be seen more as tongue-in-cheek, “as if there is ever a way to think like a great graphic designer” kind of thing. But people still on Amazon will be like, “This book isn’t what it says it is in the title.” I’m like, it’s supposed to be ironic. 


In any case, I’ve mostly approached everything like that. Like, This is my last chance for love, my last chance for a book, my last chance for success, my last chance…. And it’s only now that I do feel one notch more confident about my ability to re-create another opportunity, [but] not so much the success part, that I always feel like I have to earn. Working on it. Still time.

SB: Debbie, it was so great to have you in. Thank you.

DM: This has been a remarkable conversation, and I just want to thank you from the bottom of my heart, which is such a weird thing to say. But it is really how I feel. I just feel very open-hearted in telling you how much I appreciate this conversation.

SB: Eighteen months overdue. [Laughter]

DM: Thank you.

SB: Thanks, Debbie.


This interview was recorded in The Slowdown’s New York City studio on September 9, 2021. The transcript has been slightly condensed and edited for clarity by our executive editor, Tiffany Jow. The episode was produced by our assistant editor, Emily Jiang; managing director, Mike Lala; and sound engineer, Pat McCusker.