It will come as no surprise that the cover of Debbie Millman’s new book, Why Design Matters: Conversations With the World’s Most Creative People, is immediately striking—the title emblazoned in wide-set red type, with a thick scribble looping in and around the letters. Millman, a legend of design, as well as a prolific author, educator, curator, and pioneering podcast host, drew the scribble herself: a bold, gestural line that dances across nearly every inch of white space before eventually tying itself up. (She later reveals it was one of a hundred or so.)

The line’s circuitous journey across the cover seems to mirror Millman’s own experience publishing the anthology, which features nearly 60 interviews culled from her long-running podcast, Design Matters. After an intense process finalizing the cover art, in which Millman called in multiple different design heavyweights before getting a cover approved, the book’s original release date was then pushed by three months. While both scenarios seemed frustrating, they ultimately resolved quite fatefully. The final cover was designed by Alex Kalman, the cofounder, director, and curator of Mmuseumm and the son of designer Tibor Kalman and illustrator Maira Kalman (both of whom Millman cites as having had major influences on her work). And the new release date? February 22, 2022—both a pleasing palindrome, and a day that some believe might have astrological significance.

When I meet Millman in her office at the School of Visual Arts (she is chair of the MPS in branding), these recent bumps in the road are still fresh. But she seems to have a healthy sense of humor about all of it: “It’s been one of these things where, it’s like—could any part of this process be easy?” she says with a laugh. “I’ve done six books before. It’s never been like this. So between this sort of marathon to the design, to now the marathon to publication, I just have to let go and let God.” 

The long and winding road to creating Why Design Matters: Conversations With the World’s Most Creative People—which has been called a “salon in book form,” with Millman as our modern-day Gertrude Stein—began all the way back in 2005, when Millman was president of Sterling Brands. At the time, she was one of the few women in the United States running a global branding consultancy, and her work was so prolific and ubiquitous, that were you to walk into any given supermarket or drugstore during that era, she estimates she would have likely worked on at least 25% of products.

But according to Millman, her immense success couldn’t stave off an “echoing vacuum of meaning and purpose in [her] life.” Once the definition of a renaissance woman, she had stopped making art, writing poetry, sewing, journaling, and had tucked her guitar under her bed. It was during this phase of “creative ennui” that Millman received an offer to host a radio program from Voice America, an online radio network. Bear in mind that this was nearly two decades before certain hosts were being wooed with $100 million honeypots from network to network; the portmanteau “podcast” had only been coined the year before. Millman would have to host the show using a landline. She said yes.

Since then, Millman has become renowned as one of the finest interviewers working today, boasting a formidable roster of guests that includes Brené Brown, Marina Abramović, Ai Weiwei, Gabrielle Hamilton, Malcolm Gladwell, Miranda July, Tim Ferris, Seth Godin, Amy Sherald, Cheryl Strayed, Eileen Myles, David Byrne, Paula Scher, Tavi Gevinson, Thomas Kail, Roxane Gay (to whom Millman is married), and many hundreds of others. 

Her power as an interviewer stems not only from her sharp intellect and expert conversational skills, but from her obvious compassion and empathy—she has the ability to make her interviewees feel safe, seen, and supported. Millman herself has shared publicly deeply personal revelations, including details of childhood trauma and her decision to come out in 2012, and it is her radical vulnerability, as well as the creation of real trust between guest and host, that has made Design Matters a powerhouse for 17 years and counting. 

The new anthology features nearly 60 full-bleed portraits of its interviewees, which adds a stunning new visual dimension: A feast for the eyes and the mind. The hefty tome is divided up into “Legends” (like Milton Glaser, Marilyn Minter), “Truth Tellers” (Esther Perel, Chanel Miller, Lynda Barry), “Culture Makers” (Michael Bierut, Mike Mills, Alain De Botton), “Trendsetters” (Aminatou Sow, Christina Tosi), and “Visionaries” (Shepard Fairey, Ira Glass, Thelma Golden). One is torn between approaching the book reverently, reading deeply from cover to cover before eventually emerging, awash in sheer creative genius—or popcorning around, knowing that whatever page or paragraph or sentence you land on par hasard is sure to inspire and invigorate. 

But back to life and its mysterious, circuitous ways. After graduating college (she had been an English major), Millman applied for a job at Vanity Fair, hoping to work for art and design director Charles Churchward. And though it didn’t work out at the time, in a heartfelt visual essay, Millman recalls the many things she learned elsewhere, and how very, very high she still climbed, ending with the line: “There is always something new to dream of and always different dreams to choose. And you don’t have to pick just one.” 

Decades after dropping her portfolio off at Condé Nast, Millman sat down with Vanity Fair to discuss the art of interviewing, podcasting, juggling different creative practices, gardening, literature, and her recent trip to Antarctica with Gay—yet another full circle moment.

 This interview has been edited and condensed for clarity.

Vanity Fair: I was curious how you even began to edit this book, because you’ve spoken to over 500 interviewees, and every interview is about an hour long. What was the first step? 

Debbie Millman: It was hard because I had to reread so many of them and decide which ones were better than others, and that was brutally difficult because, you know, they’re like all my little babies out there in the world. I just didn’t know how I could possibly pick. But there was no question that I would have to also edit the interviews. And so one of the criteria was: Can I extract a piece of the conversation that stands alone without what was ordinarily like, the intro and outro? Can I get to that sort of soul of the conversation in a way that keeps the integrity of the conversation intact so that you’re not feeling like you’re missing something by not having the whole thing there? And it also feels that it’s natural and not an edited sort of piece of copy.

But I also wanted to ensure that it was timeless. Was it timeless, but also timely in a way that it wasn’t about a specific moment in time or a specific project, necessarily, but also able to address sort of human experiences that we’re still experiencing? And then another aspect was diversity. Because it's so much a part of how I choose my guests. I wanted that to be reflected in the book as well. 

And then finally, and as importantly, I needed to be able to secure a beautiful, soulful photograph because initially, pre-COVID, I was planning on doing a photo shoot and going around the country and taking photos of the guests that I had chosen to be in the book. And so that would be a connective tissue, visually, of all of the guests. But then that became impossible. There was one specific thing that I was looking for in all the photographs that I thought could connect them organically, and that was: Did I see their soul in their eyes?

That was something I was going to ask, because even when you’re just flipping through, the photos jump out at you. They’re so alive with each person’s essence. And I felt like that was probably intentional.

That was so intentional. And you know, I’m not a photo editor, but I really did enjoy that process more than I would have expected. Looking at photos and really trying to create the visual narrative of the book was as exciting to me as any other part. 

You’ve written six books prior to this. How was this process different than your past experiences?

The other books that I’ve done, I also worked with designers on all of them…. But this was much more challenging, because there really needed to be a way to help people get through the book intentionally, or rifle through it and just pick something out that they wanted to read at that moment. Because if it is on a coffee table, people generally open it up just to wherever they happen to crack open the book. And so I wanted there to be something on every page that would engage you, that would pull you in.

Going back to what you said about cutting it down to the soul of the interview—were you ever surprised, or rather, was the soul you discovered this time perhaps different from what you had remembered from that interview?

Oh, absolutely, absolutely. [Laughs] I realized just how bad of an interviewer I was at the beginning and thankfully, I do see evidence of growth, whereas I was never really empirically sure. Now I can say I’ve grown. And so there is something to be able to witness 16 years of an effort. You know, when you’re an athlete, you can tell by how many more pounds you’re bench-pressing or how much faster you’re running a mile. But as an interviewer, it’s a little bit hard to gauge, right? And I’m not even talking about necessarily the quality or the success level of the guest and how talkative they might be or how accomplished they might be—but really my ability to understand how to listen and ask a question. And I think that’s fundamentally changed since the beginning.

At what point did you notice yourself becoming more comfortable?

I would say probably around 2013, 2014, 2015. It was not only a big shift in what I consider to be my skill level, but also the audience grew considerably in that time, and I think that there might be a correlation of my getting better. And then in 2017, there was another big jump in audience, but that’s really because of Tim Ferriss, and me being on his show. But fortunately, the audience stayed with me. It wasn’t just a spike, they stayed.

But I think a lot of the improvement came from my beginning to do my own research. At the time, around 2013 or thereabouts, I was still president at Sterling Brands, the consultancy that I ran for two decades. I had somebody on staff that was helping me with my research. And so she would aggregate a big pile of research for me to read. And then she left Sterling, and so I thought, You know what? Let me try doing this, see what it’s like. 

I think that because my curiosity took me to what I wanted to talk about, it changed the level of intimacy in the conversations because it wasn’t limited to what I was given. It was then limited to what was what I could find and then what I found most compelling. That’s when my research became much more in depth, and I think much more covering the entire arc of a person’s life as opposed to what specific thing they were doing at that moment or how they felt about society or culture or whatever it is I talked to people about before that.

I feel another reason people open up so much is because you are so vulnerable and generous in the interviews. And I wonder if opening up was also a process for you?

That’s a really great question. I think that’s definitely true. I do, because I didn’t really come out until 2012. And then when I also was more public about my childhood trauma, I think those were two things I was really keeping secret. And so the fact that I wasn’t holding back so much anymore, and I think that’s absolutely, absolutely a strong possibility. 

What was the turning point for you in feeling like you could share those things?

Not having shame about it anymore. You know, once you disclose something like that, once you come out to the world and find out that they’re not going to judge you poorly, you stop being afraid of it. And then the same for a lot of the disclosure that I was sharing through working with the Joyful Heart Foundation and Mariska Hargitay [the organization’s founder], it suddenly became less terrifying. And once it became less terrifying, I feel like it no longer shackled me.

This book seems really special because it brings together three parts of your identity: a podcast host, a writer, and a designer. How do you navigate all the many things that you do? Do you have to compartmentalize? I’m curious how you hold space for all your different creative endeavors.

It’s been a little bit more challenging of late since the actual true book launch is being pushed to February, and now I’ll be doing a whole slew of new things then. I decided I’m not going to do any podcasts during that time because in the last few weeks I’ve interviewed Ai Weiwei, Michael Stipe, Maira Kalman, Keenan Scott, Ashley Ford, and these are all huge people that deserve a significant amount of research and prep time. And so I’ve gotten very little sleep and definitely don’t want to repeat that again in February. [Laughs] So I’m going to try to bank as many episodes as I can prior to that, and then have just a couple of weeks where I don’t have to worry about not doing a good enough job at something, which is a constant, constant fear.

You mentioned in the introduction of your book that you went through a phase in your career where you weren’t being as creative as you would have liked, and you dropped most of your hobbies. I was curious if any of those things have come back into your life? I know you specifically mentioned putting away your guitar at that time.  

During COVID I bought a new guitar and a new bicycle, so doing those sort of fun things definitely has come back into my life. But I also discovered gardening, because Roxane and I are now sort of splitting our time between L.A. and New York. I always try to have a garden in New York because I’ve always had like a tiny, little postage-stamp size garden or piece of land, not necessarily a garden, like a little deck or something that can put containers on. But I've always had what I described as a black thumb. No matter what I planted, it died. I could barely keep houseplants alive. I got to L.A. and I always keep trying and continue to try, and suddenly things were growing and things were happening. So that’s been a huge new part of my life that I’m loving having as both something to relax doing as well as to create and make something.

But you know, back to your question about doing all these different things at once. Mostly what I try to do—the things kind of blur. You know, I see a lot of what I make as a Venn diagram, and there’s always sort of an overlap. Prior to COVID, I was doing my interviews live in front of my students, so they got to experience that…. And my books were things that I always used as teaching tools. And so there was lots of overlap.

We’ll see how things evolve as time goes on in the world, if it does come back to normal. But there was a time where I felt like everything was really intrinsically connected. It’s a little bit harder now.

That makes sense. I had an adviser in college, and because I was always trying to do a lot of different things, she would say, “You can’t be all versions of yourself at once.” But I feel like your career is so intertwined, it’s a high-level example of someone actually pulling that off.

Well, I do think I might disagree with your teacher, but only in that it’ll take you longer to achieve mastery at them. If you’re doing a lot of different things at the same time, there’s only so much time to practice getting better. However, you know, by the time you’re 50 or 60, you’ll have put that 10,000 hours into all of those different things, and you can then enjoy having that kind of variety and diversity in what you’re doing. You just have to be patient with yourself. And I suspect that you’re probably not, as I wasn’t. But I do feel there’s something really special about that combinatorial creativity that makes everything that you’re doing richer. Eventually.

Since this interview is for Vanity Fair and you generously shared your essay about interviewing at Condé Nast with me (“Pick One”), I was curious to know: When you were applying to work at V.F., what was it about the magazine that made you want to work there?

Well, there is some symmetry here actually, I’m thinking about it. You know, when Vanity Fair relaunched back in 1982, it was a literary arts magazine, and it featured David Hockney on the cover and Philip Roth. And those are the kinds of people I would want on my show now. You know, people that are changing culture with their work.

So, for example, the [June 1983] David Hockney cover was and still is, I think, one of the most beautiful covers in magazine history. You know, with his feet, with the socks and the boat. And you know, that just wasn’t happening at the time. That kind of creative, experimental, sort of very risky kind of covers, you weren’t seeing them, you understand.

And so I thought that the magazine was reflecting culture in a way that I felt the world needed to see it. And it was so exciting to me. I thought the design was stunning. Charles Churchward was the art director at the time. I thought he did just such a beautiful, beautiful job with the magazine and the stories and the coverage was just spectacular. 

And how did you decide to take this trip to Antarctica?

So in 2017, I went through a breakup and I went into a self-imposed “I’m going to be single for like a year or two.” I’m like, not dating even, just single. And at the end of 2016, I also stopped working at Sterling.

And after I left Sterling, I started to feel like, Oh, now there’s an opportunity to really see the world in a way that I hadn’t had an opportunity to do. So in 2017, after this breakup, I decided I wanted to do something really adventurous by myself. And so I signed up for a National Geographic expedition, which was life changing and unbelievable.

And at that same time, there was in the summer of 2017 a total eclipse of the sun over North America. But in New York, we only got to see a partial. And I watched it, you know, through the little glasses, but I thought, “You know what? I would really love to see a total solar eclipse of the sun in my lifetime.” So I went to the web and was like, “Where are the total solar eclipse of the sun over the next bunch of years?” And I saw that there was going to be one in Antarctica in 2021. And I was like, “I’m doing that.”

And on my first date with Roxane, it was the end of 2018, and I told her I was going on an expedition and she was like, “Great, have fun!” And I also had this idea about going to Antarctica [in 2021]. And she was like, “Have fun!” And now we’re going together. So we’re actually doing it.

That’s such a beautiful culmination of so many things.

So many things.

Yeah, and a much better breakup reaction than like, getting bangs or something.

It’s true. Very true, very true. Actually, I’ve done that! I have done that. [Laughs]

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