Over the course of 15+ years, Debbie Millman has interviewed more than 450 people on her podcast Design Matters. But in the long line of creative journeys that have been probed on the interview-based show, there was always one notable exception: Millman herself. 

When Design Matters celebrated its 15th anniversary with a special live episode at WNYC’s Greene Space, Millman was slated to interview writer and actress Amber Tamblyn, and the artist Marilyn Minter. The latter ended up not being able to make it—so as musician Erin KcKeown plucked the show’s intro live on guitar, someone else took the stage: the writer Roxane Gay, Millman’s now-spouse and then-fiancee (and former Design Matters guest). Gay had an idea: She would flip the script, and interview Millman. The resulting dialogue shined a light on the show’s unexpected origins, Millman’s interview strategies, why she keeps the show’s “horrendous” early episodes up on iTunes, and all things beyond. 

This week, with the publication of Millman’s new book, Why Design Matters, we’re bringing the conversation to the page for the first time.

It begins in the least likely of places (looking at you, Dominic Toretto), and ultimately, strikes at the heart of the creative glue that holds the podcast—and, well, creatives at large—together.

Photo: Taryn Miller Stevens.

Roxane Gay: I’ve always wanted to interview you. So: Why are the Fast and Furious movies the best movies ever made?

Debbie Millman: That’s a trick question. I’ve never seen any of them, and Roxane almost considered that a deal-breaker when we first started dating because they’re her favorite movies, or among her favorite movies. And I was trying to sit across from her and not have a jaw drop—like, what? 

You’re not perfect, but close.

That’s not what you said last night.

Oh my God.

You set me up for that.

I sure did. Well, okay. Deborah, you’ve been doing Design Matters for 15 years. Which in podcast years is about 100. Why did you decide to do a podcast, and how have you sustained the interest in doing one for so many years?

Well, I didn’t really decide to do one. I was offered an opportunity by VoiceAmerica Business Network, which was a fledgling internet radio network at the time. And I was offered the opportunity to pay them for airtime on their network.

At the time I was doing very well professionally in a commercial realm, and I had surpassed any possible hope or dream that I’d had in my branding career. But because it was all commercial, I actually felt that I was dying and that I had lost all of my creative heart. And I wasn’t writing anymore, I wasn’t drawing anymore, I wasn’t doing anything creative—and I understood why. My professional success was the first time I’d ever been successful at anything in my life. So of course at the time I was like, okay, I’m not going to do anything but this because it feels so good to be successful at something, finally, in my forties.

But then that wore off, that metabolized, and I needed to do something creative. And this felt like a sneaky way to be creative, but still be able to justify it from a business perspective, because I could interview clients or I could interview people in the design business. So that’s really how it started. It was really a Hail Mary to my creativity. And because I have such generous friends, they were willing to come on the show. I mean, they had no reason to come on the show. Steven Heller is my mentor, my fairy godfather. He’s been on the show 13 times. 

I want to do it with him every year so we can create this oral history of design together, and every time he says “okay,” he’ll do it, I’m shocked.

But why it grew, I think is just because of the guests that I have and the generosity and their hearts. For me, I’ll never ever get tired of talking to people about who they are and how they’ve become who they are, and how they make their lives and how they create and make things out of nothing.

I’ll never ever get tired of talking to people about who they are and how they’ve become who they are, and how they make their lives and how they create and make things out of nothing.

One of the things I’ve noticed about Design Matters is that there’s a narrative arc to each episode. You really tell a story, or you ask the kinds of questions that will get your guest to tell a story. So what does a good narrative arc look like for you in a given episode?

It’s like a game of pool. Billiards. I think a great conversation, or a great interview, really, is a game of pool because when you’re playing pool, you’re not only shooting one of the billiard balls into the hole. You also want to leave the rest of the balls on the table so you can continue to shoot more holes, and so forth.

So what I try to do is ask a question that will allow me to be able to continue the conversation no matter where they take their answer. For me, it’s about being prepared to go wherever they go, and know enough about where they may go to be able to anticipate any number of answers they could give. Mostly, I try to listen really hard.

That’s why I stare at people when I interview. And I try not to talk, which is why I nod all the time. So you know, like a little bobblehead sitting here. But it’s mostly because a lot of people, when they’re having conversations, talk, talk, talk, talk, talk, and then stop talking while the other person’s talking, only to then wait til they finish talking to start talking again.

After the interview with my second-ever guest, Cheryl Swanson, I asked her how it went—and was really expecting, “Great.” She said, “Well, maybe you should listen to my answers before you ask the next question.” Thank God that was episode two, as opposed to episode 302. 

I also don’t like to do my interviews remotely because I like to be able to read a person and know if they’re feeling uncomfortable, or when I might be able to push or say, “Really?” Because I know that maybe they’re not giving me everything. 

How far are you willing to push someone to get a good answer, or to get at least an authentic answer?

Well, maybe push isn’t the right word.

Nudge?

Urge, nudge, encourage, inspire. I mean, part of the reason that I like to start the show with a question that surprises people is so that they understand that I respect them enough to do the deep research. And that if I give them that sense of taking this interview really seriously, that they’ll in turn take it as seriously as I do. Because all I’m really interested in is talking about them and not judging at all.

I want to be able to offer their story to the world in a way that celebrates who they are, but also allows other people to be inspired by their struggles or how they overcame something to become who they are. Because really, there’s only two interviews I’ve ever done in the nearly 500 where the people that I interview were like, “I’m just cool with who I am. I don’t give any fucks anymore about anything.” And those men were in their eighties. 

I like how they were men.

But they were in their eighties. And so I think at that point they had earned that. There’s not anyone I’ve ever interviewed where I got the sense that they were absolutely comfortable being who they are and owning the world in the way that they should or could. They’re opening their hearts and showing who they are in a way that I think gives people a sense that anything is possible for anyone.

You mentioned the deep research. And one of the things I don’t think people understand about Design Matters is that Debbie does hours and hours of research for every single episode. Hours. And when you talk to her while she’s researching, it’s not a good idea. But it’s really impressive. When you interviewed me, I was really surprised by the level of depth that you were able to achieve and sort of get into deep cuts. And so what does your research process look like for an episode?

Well, it depends on who I’m interviewing. I just interviewed Lucy Wainwright Roche, the musician. I’ve interviewed Erin McKeown, Kaki King, Amanda Palmer. If I’m interviewing a musician, I have to try to listen to their entire body of work, which is wonderful, but also very time-consuming. Fortunately, I can listen while I’m doing other things and sort of get a sense of their music.

If it’s a writer, I have to try to read as much as I can. In preparation for my interview with you, I was so terrified that I’d be caught not having the answer to something or knowing something. I had to read everything twice. And so I did, but that was joyful. Somebody like Alain de Botton, who has 20 books, that was really hard to do. So what I decided to do was read the other books that were sort of in the category of the book, because that was a novel, and he doesn’t write a lot of novels. And I had also read somewhere that it was a sequel to a book that he had written 20 years ago, which was one of his first novels. And there was only one line in the second book that made it clear that it was a sequel, but I found the line. So that made me really happy.

Of course.

But generally speaking, I try to read as much as I can of whatever body of work, or listen. I feel comfortable if I have about 50 pages of research. And that’s generally things that I’ve found online or transcripts of audio. Inasmuch as I also get hard copies of everything, because I want people to sign them, I also get everything on Kindle. Then I can highlight and transcribe really easily. So generally speaking about 50 pages, then I cull that down to about 10–12 pages of questions. And then for an hour-long episode, I have to cull it down again to about five to seven.

The really hard part of doing an interview is knowing when not to ask a question. You know, you want to flow with the conversation. So that’s part of the research, is having enough to be able to pivot any way somebody goes. 

And so I think Curtis Fox, my producer, gets really nervous when I come in with 10 pages and say, “Curtis, I couldn’t cull it down to anything less than 10 pages.” And then I try to, as I’m interviewing, make the decisions about where to go next. So that’s how it works.

“The really hard part of doing an interview is knowing when not to ask a question.”

That’s incredible. And it shows. Have you gleaned any insights about creative people in general over 500 episodes?

No. None.

All right. Next question. No problem.

Yes. I mean, I think that everybody is insecure. Everybody is searching. Everybody’s hoping. Everybody’s had trauma. I think that no matter who I’ve interviewed, whether they’re super-duper famous or just starting out, the people that seem to resonate the most are people that put their whole hearts into everything and show everything. And that never gets boring, ever, which is why I hope that I can do this for the rest of my life.

Do you put your whole heart into everything?

Sometimes tragically, but yes.

What does the next 15 years of Design Matters look like?

Oh, I have so many good plans. I can’t talk about a bunch of them yet, but there’s some really exciting things that have popped up just unexpectedly. Very serendipitously. One of the things that’s interesting about the show is the early horrendous episodes of the first four years. Four years of horrendous episodes. I mean, that that’s resilience, right?

Yes, it is.

And I keep them up on iTunes just so I can say to people, “It takes a while to get good at something. Trust me.” It took me 100 episodes to really begin to understand. 

The sort of brand consultant is still alive in me, too. And I think Design Matters is not really a great name because it’s not really about just designers anymore. It’s about how the world’s most creative people design the arc of their lives, and “Design Matters” … that works, right? Eye roll.

But I just see being able to do that with more and more and more people, and more kinds of people. I love talking to scientists. And then I get all of my questions about how we got here sort of unanswered, but at least asked. And I love to talk to artists. I just love to talk to anybody that is able to create something or make something or think something out of nothing.

If you could rename the show, what would you call it?

“What Matters.”

Oh. Wow.

But I think that’s a little egoistical.

No. Well, I think on that note—Deborah Millman, everyone.