Designer, writer, and host of the hit podcast Design Matters Debbie Millman joins Zibby to discuss her new book, Why Design Matters, which features a number of her past interviewees. The two talk about the five-year journey it took to create this book, which life experiences shaped Debbie’s relationship with brands and branding, and why they have the best job in the world. Debbie also shares the most important lessons she has learned from hosting her podcast for seventeen years.


Zibby Owens: Welcome, Debbie. Thank you so much for coming on “Moms Don’t Have Time to Read Books” to discuss your book, Why Design Matters: Conversations with the World’s Most Creative People.

Debbie Millman: Thank you. Thank you. Thank you. I’m so honored to be here. I love your podcast. Thank you.

Zibby: Oh, my gosh, you’re so sweet. It’s so funny because a couple years ago when I was nominated for a Webby Award, you were one of the people I was nominated against. I was like, who is this woman? What’s going on? I did all this research on you, so I’ve been following everything you do since then. Now I’m so delighted to be talking to you.

Debbie: Me too. Same here. It’s great that we can finally meet face to face.

Zibby: It’s also so neat because you are this consummate interviewer. All the introduction to this book — everybody’s talking about your wife, Roxane Gay, and Tim Ferris. Even your description of how you do things and how many episodes you’ve done, over four hundred — everybody’s talking about your amazing interview style. Here I am on this podcast. I’m like, well, gosh. Anyway, I’m kidding. I’m like, how does she do it?

Debbie: Happy to talk about it. It’s just so easy for me to talk about. Please, if you want to talk about that, we can absolutely do that.

Zibby: Okay. Let’s start with this absolutely gorgeous book, Why Design Matters. First of all, as a coffee table book, this is amazing. For people listening, it’s this square book, white with red letters, and this little, squiggly, black line. It looks like something you just want to cuddle up with and read and delve into every picture. Then all the pictures inside are gorgeous of the different guests that have been on Debbie’s first radio show and then podcast. Why this book? Why this way to do this book? There were so many ways you could’ve gone. Tell me about that.

Debbie: Initially, just a couple of years after the podcast started back in, I want to say 2007 or so, so two years after I started the podcast, I was actually talking to Steven Heller who is featured in the book, who’s my mentor, and who’s written about over two hundred books about design and culture and every aspect of the creative practice. I hadn’t published a book at that point. I really wanted to. The thing that felt most credible to me was maybe doing something about the podcast or on the show that I was doing at that time, which he didn’t think was a very good idea. The reason was because he felt that everybody could just listen for free. There was no reason. In hindsight, I’m really, really glad I listened to him because two years after doing the podcast, I was still a pretty crummy podcaster.

Zibby: Oh, please.

Debbie: No. I’ve been doing this now for seventeen years. The first four, I did not know what the heck I was doing. I was terrible. I remember asking my second guest after we were finished — she was a friend. I said, “So how do you think I did?” expecting back-pats and high-fives. She paused and said, “Well…” You know nothing good is coming after that word, and said in quite that way. She said, “Well, it might be better if you listened to my answers before you started crafting your next questions in your head.” She was right. Over those first five years, even, I would say I was constantly learning on the job. To have come out with a book at that point would’ve been a disaster. In fact, I really didn’t think about it again because at that point in 2017 when the book deal first came together, I had already published a number of books. The idea of doing that specific kind of book about the podcast had long fallen by the wayside. My agent, Charlotte Sheedy, was really certain that at that point in time it would make a good artifact, if nothing more, about the history of the show, about the longevity of the show, what it was like in the early podcasting years, which was sort of the goldrush in a lot of ways. I reconsidered and thought about it.

At that point, pre-pandemic, I was excited thinking about approaching this more from an editorial perspective. I want to go on a photoshoot. I was going to take photos of all the guests that were included. It was going to be a very creative, highly hands-on endeavor. Then of course, the pandemic hit. I had to rethink everything I was doing about this book, which I had already gotten an advance for, some of which I’d already spent. It wasn’t like I was giving it back. At that point, I had to rethink. I got a year extension because of all of the things that were happening in the world with the election and with COVID. Now the book is finally coming out almost five years later after the original idea first became a reality. Despite the length of my answer, it’s a little bit hard to say why now only in that I think that Charlotte really believed that there was something to be offered in a collection of some of the best conversations that I had. I agree now that it’s done. I feel really grateful to her for helping me to make this happen.

Zibby: Also, the format choices, I’m interested in. I’ve always thought, what should I do? I have all this content. I have hours of conversations. What do you do with them? You’ve chosen to do this in such a gorgeous way. This is such a unique way to handle that. I know your background is all in design, so of course, that makes sense for you and your brand and everything. Just speak to how you came up with this format and the way to tell your story through your conversations.

Debbie: I do have to say I rode the coattails a little bit of the great designer Michael Bierut. Michael Bierut is a long-time partner at Pentagram and has really helped create the visual language of our world, honestly. He’s that accomplished. I was sitting in my editor’s office as we were talking about my vision for the book. I knew that I wanted to do something square because of the format of the logo and the way that visuals show up on Apple Podcasts and Spotify and so forth, that little square, which used to be a giant twelve-by-twelve album. I was sitting in her office. HarperCollins also published Michael’s book. Michael’s book was ten by ten and gorgeous. The paper was gorgeous. The jacket was gorgeous. The case was gorgeous, everything about it, the photography. I said, “I’d love it to have that sort of plunk value of Michael’s book.” That ended up biting me a little bit in the back only in that when I came to Charlotte with the first round of covers — I’m sorry, not Charlotte. When I came to my editor with the first round of covers, she was like, “Well, they look a little bit too much like Michael Bierut’s.” I’m like, “Michael’s book came out five years ago. They really don’t. It’s a totally different title.” She’s like, “I don’t know if I told you, but Michael’s reissuing, republishing a book in a new edition coming out the same time yours is. Because of the size, we don’t want people to get confused given that you’re both in the design field.” I was like, oh, my god. We ended up having to work around that, and I think, ultimately, in a beautiful way. Michael’s book is black with white type. Mine is white with gray and red. That was a struggle, though, for a little while and kind of a big disappointment. I also didn’t want Michael to think that I was copying him any more than I already was.

Zibby: Then in terms of the inside, in terms of who was featured, some authors have a big picture, which is gorgeous, like Anne Lamott — by the way, we have so many of the same guests. I wanted to make a whole list. It was really exciting to see them. Anne Lamott, who is one, has a full-page, beautiful picture of herself. Then someone like Alyssa Altman, who I also adore, has a quote. You have some quote pages that aren’t — how did you go about figuring that whole thing out? Who’s getting a quote? Who’s getting an excerpt from their interview and the picture and all of that?

Debbie: It was a challenge because I have interviewed over four hundred people. I had a finite number of pages. I was originally supposed to submit seventy thousand words. I submitted a hundred and fifty thousand. Thankfully, we did a lot with the type to make it all work. If I transcribed any of my interviews, especially in the later years, I would say from 2015 to now, those interviews come in at about ten thousand words. There was no way I was going to be able to include ten or fifteen interviews. It just wasn’t going to work. The biggest criteria for inclusion was, can I pull out a part of the conversation that could stand alone without a beginning and an end? The well of the conversation, does it stand up on its own? In some cases, it didn’t. In some cases, that well, that significant aspect of what we were talking about was highly dependent on their backstory, their origin story, and so I couldn’t. I couldn’t take it out. I didn’t want to destroy the integrity of the interview by pulling something out. The quotes became a way of still including people that I felt belonged in the book, simply.

The interviews themselves, not only did I feel like I could pull out something stand-alone, twenty-five to four thousand words, I’d also felt like it needed to really be timely. There were some authors that I had on the book where all we talked about was the 2016 election. I don’t want to do that again in the book. It would feel really stale. Not that the topics aren’t interesting, but the actual specifics of the election would feel really overdone. I had to make some really, really hard choices, the excerpt ability, the timeliness, and it being timeless, and then, as importantly, and I’m glad you mentioned it, the photography. Initially, I wanted to go on a photo tour, which would’ve been a blast and so much fun, but I couldn’t do that. It was COVID times. I also didn’t want to do remote photography where I was directing somebody through the screen. Didn’t feel like that was intimate enough. One of the things that I ended up having to do, surprisingly, quite unexpectedly, was photo-edit my own book. That gave me a real opportunity to do something that I hadn’t done since college when I worked on my student newspaper. That was to really become a photo editor and research and find photos that I felt had the right energy and soul.

One thing that I didn’t want was a magazine-type book where it looked like different articles from different writers and photographers. I really wanted there to be a thread that knitted all of the photographs together. For me, that became, every photograph had to reveal the author or interviews or — it was authors’ interviews, musicians, so many, designers. It had to reveal their soul. I really, really think I did that, I have to say. It’s one of the things that I’m proudest about in this book, is the journey that people take through the book looking at the artists and editors and writers and performers and so on and so forth. Some of them were really hard. There were a few that I had to exclude because I couldn’t get a photo that really said, this is who I am. Look at me. See me. Then that was what I would include. The people that I wanted to include were really important to me, every single person. It’s like Sophie’s Choice, picking interviews. It’s ridiculous. That was a way for me to include a lot more people. I also was able to do that on the end pages. I did that as well. Then there’s also a little surprise under the jacket on the case of words that I chose that if people explore enough they’ll find.

Zibby: Under the jacket, okay.

Debbie: On the case.

Zibby: Ah.

Debbie: Oh, I’m glad you didn’t see it yet. Yay! Reveal in real time.

Zibby: Wow, look at this. Oh, my goodness, very cool. So neat. I love it. These pictures, oh, my gosh, I feel like I’m with some of these —

Debbie: — Albert, yeah. That picture of Albert is wonderful.

Zibby: I’m sorry, I’m holding up Albert Watson. You have this mix of

Debbie: , yeah.

Zibby: — and these close-up smoldering looks. I remember earlier, I saw Alain de Botton. He was farther away. I’m trying to remember what other ones. This one of Malcom Gladwell.

Debbie: Pensive.

Zibby: Pensive and thinking. Beautiful.

Debbie: Believe it or not, this ended up becoming the part of the book that I had the most joy with.

Zibby: I was the photo editor of my yearbook back in high school.

Debbie: Ah, yes. You know. It brought me back to college. It was phenomenal.

Zibby: Back to the darkroom and all of that.

Debbie: The stack camera.

Zibby: The layout and all of that. I love photography so much. Seeing these pictures, this is a work of art just in that.

Debbie: Thank you.

Zibby: It was really neat. Let’s talk a little bit about your interviewing. I loved how it was described in the book, exactly what your studio looked like. Is that still how you do them with the —

Debbie: — It is when I can do them in person. Because of COVID times, it’s much harder. It was a big adjustment to begin to do the interviews via Zoom like we’re doing now. I also sort of think there’s something slightly more intimate about being a lot closer to a person. When I’m in my studio — it’s a very small studio. It’s very intimate. It’s dark. We’re still three feet apart. On Zoom, you’re really just one foot apart. There’s no barrier. You’re just looking right into someone’s eyes. At least, it feels that way to me. The process of doing the show in the studio, it feels a long time ago. I’ve only done one since with one person. No, I’m sorry, two since 2020. Two in the studio. In 2021, I did a record number. I think I did thirty-seven episodes. That’s a lot of Zoom time. It’s sad me to not have that physical presence. One of the bigger differences and one that I’m sad about is, in the studio I was able, after the interview — I always had a live studio audience, a little bit like Inside the Actors Studio, but it wasn’t televised. When we’d come out of the studio, my grad students would have an opportunity to ask their own questions of my guest for about a half hour. That’s something I really do miss, first, because it gave them some access they would never have otherwise had, which they loved. Secondly, they always ask really good questions. They ask really good questions. I always was learning from them about what they were curious about. That’s an aspect of the show that I’m sad about.

Zibby: You know, I did something sort of like — I might have a solve. I have this virtual book club. I talk to the book club about the book. Then I always have the author come for thirty minutes of Q&A afterwards.

Debbie: That’s wonderful. I’m thinking about doing something on Clubhouse where I invite the guest back. Then a big audience could come. Because everything is audio, I don’t know that anybody would feel like they were missing anything by being able to join. That would also require — I don’t know how you’ve been able to ask people for more. I always feel so apprehensive about asking, would you like to do this too? I think I’m going to try it with people that are willing.

Zibby: I don’t do it at the same time as the podcast.

Debbie: I won’t. That’s a good idea.

Zibby: It’s more like, hey, would you — I don’t think it’s such a big ask for thirty minutes of someone’s time for Q&A. It’s pretty easy. They don’t have to prepare anything. They get exposed to some new people. I haven’t found that to be too hard. I feel worse — well, I don’t know. Anyway.

Debbie: That’s a whole separate conversation about what we feel entitled to do and not to do.

Zibby: I know, exactly. I’m like, maybe I should just stop right there.

Debbie: We can talk about that when I have you on my podcast.

Zibby: Oh, my gosh, too funny. Your conversations, though, they’re in-depth and long, right, an hour and a half?

Debbie: Sometimes. They’re usually an hour and a half. I have a very intense editor. Every now and then when we were in the studio, I’d see him looking at his clock. I’d be thinking, that’s where he’s cutting it, looking at his clock .

Zibby: When my editor falls asleep, I know that —

Debbie: — If my editor is bored, I know I have to speed things up a little bit. I love to talk. I love to hear what people have to say. I love to listen. I love to just probe. Ultimately, though, unless they’re musicians where they’re playing something for us, generally now, they go about an hour, a little bit over occasionally, but mostly about an hour. Although, yes, I’ll keep talking to people until I sort of sense that they don’t want to talk anymore.

Zibby: I feel like that’s a bigger ask, to be honest, because that’s a big chunk of time. Somebody could go watch a movie or something. Not that they would have. It makes your format so powerful, the intensity and how deep you are able to go. That’s really such a gift.

Debbie: Thank you. I do love it. I feel like I have one of the best jobs in the world, being able to listen to people. Now I’m getting into a place where there are people that I’m interviewing that I have been fans of for most of my life, and certainly all of my adult life. I interviewed Jones a couple of months ago. I’ve been kind of obsessed with her music since 1979 when she first came out. To be sitting face to face with her — at one point, she started to sing. Michael Stipe from R.E.M., same timing. Thinking back to my younger self and imagining, fantasizing at that point about being able to talk to them, it would’ve felt like, no, you’re talking about somebody else’s life. It feels so extraordinary to be able to do something like this when these people mean so much to me. It’s a gift.

Zibby: Debbie, I feel the same way. This is what I’m always saying about this. Books that I read as a kid or in my twenties or thirties or whatever or during a really hard time of my life and that was the book that helped me through and then all of a sudden, the author is sitting next to me here or on Zoom and I get to talk to them like any other conversation I would have all day, it’s like magic. It’s just amazing, and even just to be able to thank someone for the profound effect they’ve had in your life. I know they probably get it all the time.

Debbie: Goosebumps. I have goosebumps because I feel exactly the same way.

Zibby: I feel like we also have so many — I started my whole career in branding, and so I was really familiar with all the — you, of course, went to the top of your field and ran your own company and everything else. I’ve always been really interested in understanding consumer behavior and consumer relationships, people’s relationships with the brands that they love. I couldn’t articulate exactly why. From a young age, I was like, I want to write a letter to Colgate. I did this with authors too. My mom would read me the back of the shampoo while I took a bath. I’m like, read it to me again. I was pathetic. It’s pathetic.

Debbie: Oh, my god, I love that so much. What I would not give to see those letters.

Zibby: Right? They would send me form letters back. Thank you for writing us about how much you like Kleenex. I was like, wow, I got a letter from a company. Then I worked in advertising and brand planning for a little bit. I got to be a part of that whole thing. I would sit in as a college intern on the Maxwell House campaign things or the Pepperidge Farm this or that, and Kodiak.

Debbie: Oh, my god, both of the brands, I worked on. All of those brands, I worked on. Oh, my god, we could’ve been in same meetings. I think that you should write a story called “Letters to Colgate” just about your feelings about that time. I think so many people would relate.

Zibby: I love it. This is what I usually do, is tell people what they should write about. This is great. I feel like there’s some overlap in this. There’s something about the power of brands and brand relationships because it’s really intimate, honestly, the feelings you have. It’s another relationship that you have in your life. It’s somebody you trust. It’s somebody you can feel betrayed by. You can feel a loss, like when something’s discontinued. The corn muffins at Barefoot Contessa, the shop, when that shop closed, I felt like I grieved for that because that was a brand for — then of course, she went and made all the cookbooks and is very omnipresent at this point. There’s something about that. You’re the brand guru of all time. You were so funny in the book saying that you thought maybe you would go in the grocery and almost everything on the shelves you felt you had done their branding for. Tell me a little bit about relationships between people and brands and then how that gets translated into this deep curiosity into people in general.

Debbie: It’s a great question. Early on, I had a really, really — as we’ve all had, but I had a very difficult upbringing. When I felt bad about myself, I started to fantasize that if I had certain things, that it would make me feel better about myself. My dad was a pharmacist. He had his own pharmacy. When I went to visit him after school, first, just to hang out and play in the back of the store, but then in later years to actually work in the store and work the cashier and do a lot of his shelf setups and windows and so forth, I began to sort of fantasize about what these things could do for me. My very first obsession were with Goody barrettes. He had what I felt was a magical, sparkly, shining wheel that spun. On the hooks were all of these barrettes and ponytail holders and headbands. I thought, oh, my god. Every time I went to visit him, I was allowed to take one thing. I would spend half an hour deciding, should I take the yellow ponytail holders or the red headband? I remember so desperately wanting, one of my best friends who lived next door, one of her ponytail holders that was a particular kind of pearlescent yellow that I couldn’t find anywhere. I stole it from her. I wrote a whole story about it. I stole her barrette. I wish that I could find her and apologize and send her five hundred yellow ponytail holders. That’s how desperately I wanted to feel better about myself.

What I realized from a very early age was that whatever cache these things were giving me — I couldn’t have put it into words at that point at all, probably not well in my thirties. They were just replacing or really trying to fill up a very hollow center that had a lot of leaks in it. It was a real leaky bucket. Goody barrettes turned into Levi jeans, turned into Lacoste shirts, turned into Nike sneakers, turned into a Prada jacket. That doesn’t ever last. We metabolize our purchases very quickly. We metabolize everything. We metabolize our promotions. We metabolize our hunger. Everything is metabolized. That’s part of the nature and the chemistry and biology of our bodies and our brains. That, over the years, has become harder and harder to balance with the need to responsibly manage the way in which we manufacture products on the planets, but also how corporations have a fiduciary responsibility to the shareholder. It’s very hard to say that you’re going to put the needs of the planet or the needs of the people first when Wall Street is managing your finances and looking very closely at your finances. The way that our capital system has been set up is problematic in that way.

Zibby: Wow.

Debbie: Long answer.

Zibby: No. Can you tell me more about your childhood and why it was rough? You don’t have to.

Debbie: Trigger alert for people listening. My parents got divorced when I was eight years old. My mom went on to marry somebody that was physically, mentally, emotionally, sexually abusive to me and to some of his other children. That marriage lasted four years. During that time, I was not allowed to see my biological dad. Then I was. He had some significant anger issues, ended up marrying somebody that also just was very hard for me to be around for lots and lots of reasons. My dad was a super complicated person. I loved him very much. I wanted very much to make him proud of me. I was a great student, an overachiever, your classic people-pleaser. Yet it was almost impossible to please him. Over the course of our lives together — he passed away in 2015 — there were five significant estrangements that we had where for a decade or so we wouldn’t speak to each other. That was the longest one. He chose not to speak to me. That was really, really hard. My mom’s been married four times. She’s now a Trumper, believes that Trump is the prophecy, thinks that if we should be wearing masks, we should be born with them. My therapist said, when she heard that, “What about clothes?” My mother’s also a seamstress, so the whole thing is just batshit. That gives you just some top-line points.

Zibby: Oh, my gosh. I’m sure you’ve done the work with your therapy and everything else, as we all aspire to do all the time, but the consistency of a brand is a huge balm. It’s always there. It always delivers.

Debbie: Oh, yeah. That’s why people get so upset when things are changed. It’s quite astonishing to see that we’re living in a day and age when a brand changes their identity, that petitions are created to mandate that they go back when what they went back to was a hundred and fifty years old. Nobody likes change. Change sets up all sorts of alarm bells in the reptilian brain which wants to be safe and secure and certain and know what’s coming next and be on secure footing. Any kind of significant change creates a sense of vulnerability and uncertainty in a person. They don’t know if it’s the same product or the same ingredients, the same cost, the same content. That creates a sense of nervousness and trepidation, which people then respond to, as you can see online, with lots of anger and sometimes real vitriol.

Zibby: In terms of translating the visual, that’s one piece I feel like you have down pat. I feel like I have the relationship piece, but I don’t have — I can’t create, necessarily. I know what I like. I’m trying to teach myself Canva.

Debbie: Good for you.

Zibby: I just want to be able to do the things that I know I like because it’s so hard for me to explain it. I feel like you’re more on the — you totally get it. You’ve started this whole School of Visual of Arts program. How comfortable are you with the execution of all of it versus the instruction?

Debbie: I’m a wonderful art director. I am a wonderful strategist. I can say that with great confidence. I have a great eye. Those are things I know I do well. It’s always good to know what you do well. It’s also really important to know what you don’t do well. I’m not great on all of the Adobe programs. Though I respect them and use them, I’m not, by any means, an expert. I know I need help there. The bigger issues for me are the things that I don’t know that I don’t know. Obviously, I do know Canva. You could’ve said anything, and I would’ve been like, oh, what’s that? Whenever anything new comes in, oh, what’s TikTok? Oh, what’s Vine? Then I learn them, but I’m not an early adopter by any means. My wife often jokes that I have such a complicated relationship with technology that it’s hard for me sometimes to figure out how to turn on the TV.

Zibby: It is hard. I’m so annoyed at the TV. I am so annoyed at all the things, but that’s another — I want a boombox back where I press one button and I could have music. WPLJ and Z100, that was it. There were two choices. Anyway, I know you’ve written more than this, of course, but unless I missed it, I didn’t see that you’d written a whole memoir. Have you written a memoir?

Debbie: No, I haven’t written a memoir. I’ve done a lot of visual essays that are memoir-ish in nature but short. I’m very tentatively taking steps to thinking that that might be what I do next.

Zibby: I started this publishing company called Zibby Books. We’re doing twelve books a year, fiction and memoir. We just announced this book we’re doing with Claire Bidwell Smith, who wrote The Rules of Inheritance, called The Rules of Forgiveness. We’re really trying to do books just like what I would imagine your memoir would be. I’m just putting it out there. If you have any interest in working together on it, I think it would be amazing.

Debbie: Oh, my god, thank you. That would be amazing. It would be very visual. I do a lot of drawing, and so probably more in the vein of the book of illustrated essays that I did called Self-Portrait as Your Traitor, but that was not a memoir. It was just reflections.

Zibby: If you want to talk after, I think that would be so cool. Your story and how you’ve come out of this, I just want to hear more and more and more. I’m totally over the time. Usually, I never lose track of time. This might be the only time I’ve lost of track of time.

Debbie: Oh, wow. Thank you, Zibby. Thank you.

Zibby: Last question. Do you have any advice for aspiring authors?

Debbie: Aspiring authors, draw your words. It opens up different parts of your brain. At least to get started, especially if you have some writer’s block, draw the words.

Zibby: I love that. I cannot draw to save my life, but that’s okay.

Debbie: That’s also why. You don’t have as much expectation for excellence. Just the exercise of drawing the words sort of opens up different neural pathways.

Zibby: I’m sorry I took extra bits of your time here today. I’m so sorry.

Debbie: My absolute pleasure. Don’t be sorry. This was so much fun, so much fun.

Zibby: It was great to get to know you.

Debbie: Great to get to know you too. I’m in New York too, so let’s definitely have a coffee when I’m back in town.

Zibby: Yeah, that would be great. I would love it. Take care.

Debbie: Thank you. Bye.

Zibby: Bye.


WHY DESIGN MATTERS by Debbie Millman

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