Debbie Millman: peak the day before we die

PF: I am Paolo Ferrarini, and this is Parola Progetto. Parola Progetto is a podcast of conversations with people whose lives are made of projects, where we explore design in all its forms, without objects or images, simply through words.

And here we are.

Today we are in Brooklyn, hosted by our friends at Salotto, for the second night of a series of three very special live events of Parola Progetto. And I’m thrilled to have next to me Debbie Millman.

Introducing Debbie is simple, and I’ll start from her Wikipedia page: “American writer, educator, artist, curator, and designer, who is best known as the host of the podcast Design Matters.” At the same time, introducing Debbie is not that simple, because of the many professional lives and projects she has made during the course of her career. Brands, strategies, designs and redesigns, books, editorial and educational projects, and most of all, Design Matters, the benchmark for all podcasts about design and creativity. But I want to introduce Debbie by simply saying that she’s one of the most genuinely curious human beings I’ve ever met. Someone who is incredibly interested in understanding her fellow humans, with a rare talent for listening.

Hello, Debbie. Welcome to Salotto, and welcome to Parola Progetto.

DB: Thank you. It’s really, really nice to be here.

PF: I have a little confession to make.

DB: Tell me.

PF: You already know that, but Parola Progetto listeners might not. I’m a bit of a copycat, or maybe a thief. My podcast actually started as a fan project. I’ve always loved Design Matters so much that from day one, Parola Progetto has been trying to mimic it. Can you forgive me?

DB: Of course! “Love means never having to say you’re sorry”, which I’m not entirely sure that Italians might know that quote, or young people. It’s a quote from an old movie called “Love Story”. And it was an old movie, I think in the ‘70s, but it was one of those landmark movies that sort of changed a lot of things that came after it. And one of the famous quotes is, “Love means never having to say you’re sorry.” And there have been times where I’ve said that, and people are like, “what do you mean? Love means you should always say you’re sorry.” So, in any case, either way.

PF: OK. Thank you. Thank you, Debbie. I feel more relieved now. Let’s pick up where we left off. We met for the first time in March 2020 in Cape Town during Design Indaba. March 2020. We were in this wonderful bubble, the design bubble, but also a bubble of calm while the world was totally changing with the arrival of COVID-19. We parted with the promise of doing a podcast together in New York, and today we’re here to keep that promise. Yes! So very simple question. What’s happened in your life since 2020?

DB: Such a simple question! Well, the first thing is I got married. Yeah, I got married. [APPLAUSE] Thank you.Thank you. [APPLAUSE] We were already engaged at that point. We were supposed to have this very big wedding in October of 2020. And 10/10/2020, as fellow designers will appreciate, the numerical symmetry. And we picked that day very intentionally because of that symmetry. And Chip Kidd designed a monogram for us, a bit of a monogram. It was Roxanne’s name and my name sort of overlapping typographically, very beautiful.One of my big regrets at that time was, well, we didn’t get to use it. Gloria Steinem was going to marry us. It was this whole big thing. And we realized, I think, in April that there was not going to be a big wedding, which was kind of unfortunate because we had already paid a lot of things for a wedding that you have to pay in advance, but whatever. And so, we decided to elope. And we eloped in a strip mall in Encino, California. I think the name of the place is like weddingstogo.com. I’m really not joking. We had a plastic chuppah because I’m Jewish. And so, we stood under that. And remember at the beginning of COVID, we were all still wearing plastic gloves. So, we were wearing plastic gloves and masks. And my cousin drove down from Santa Cruz, Northern California. And I have a very dear friend that lived nearby. So, they both came. Nobody in my family knew we were doing this. I called both my brothers en route to Weddings To Go and told them that I needed them – I texted them and said, I need you to be available at 4:15 Eastern time. Then finally, when everybody got on the phone, it’s like, “hey, we’re at Weddings To Go. We’re going to get married. Wanted you to participate via FaceTime.” And they were like, “what?” So yeah, so that’s the biggest news.

PF: OK.

DB: Oh, we got a puppy.

PF: Tell me more about it.

DB: It’s a pandemic puppy named Maximus Toretto Blueberry Millman Gay. And he’s really – I love that somebody went, aw, because really, he’s that cute.

PF: On Design Matters, you ask a lot of questions. As a listener, I can tell there’s a real curiosity. Have you ever wondered where your curiosity comes from?

DB: Hmm, it’s a good question. I mean, I am endlessly fascinated by people. And I think because real tangible actualization, thinking about Maslow and that top part of the pyramid, didn’t come till much later in my life, I have always wondered how creative people found the courage to be creative. And so, I think my curiosity was fueled by that desire to understand and know in a somewhat narcissistic way to try to help fuel my own. If I could figure out the holy grail of how to manifest the courage to be creative, then maybe I can use that for myself. So, it’s all just really selfish.

PF: Yes, like all forms of creativity, in a way.

DB: I mean, maybe. I don’t know. That’s a provocative statement. That’s a really provocative statement! He said it so nonchalantly, like, that’s all creatives. I don’t know. Do you think so? Do you think that all creativity is selfish?

PF: You’re asking a question…

DB: I know, I can’t help myself.

PF: You can’t help it.

DB: Well, let’s deconstruct this. I mean, it’s so interesting. Maybe it is, because I mean, people have to feel when they’re creative that somebody would be willing to look at their work. And that is inherently selfish.

PF: Yes, it’s a desire to show maybe what’s your worth. So, you want to show people that you’re doing something good. So, in that sense, I don’t know if I would call that selfish, but..

DB: Well, there is an inherent confidence in that. Like, I’m going to make something, and I’m going to spend all of this time making something. And I’m going to do whatever I can to share that publicly. And that sharing, that public sharing, requires a real sense of either belief in oneself or hope that others will believe in you. If you have both, it’s probably because you were well-parented.

PF: Have you ever found yourself asking your guests tough or tricky questions? Because to me, it seems that you’re always very, very kind, but a sort of kindness that makes people comfortable and makes you able to take very, very important things out.

DB: I’m not a gotcha type of interviewer. I’m not an investigative journalist. If anything, I probably am an ethnographer, really trying to understand humanity through questions. I mean, I sort of see myself telling stories through questions and telling someone’s stories through questions, because the questions that I ask, I’m hoping, will reveal or contain some sort of narrative arc that will express who they are in their own words. In terms of tricky questions, I mean, I think I do start out every episode with maybe not necessarily a tricky question, but an unexpected question to do a couple of things. One, to put people at ease. Two, to make them laugh, which always helps putting people at ease. And then also to give them a sense that I’ve done enough research to find this little nugget that will do both of the above. And that takes more time than anything else, finding that little question that I know when I find it that that’s the question.

PF: Let’s see if this works.

DB: Oh, crafty. Very crafty.

PF: I listen to you!

DB: I see what you did there.

PF: And I tried to—

DB: Nicely done, Paolo.

PF: Is it true that…

DB: And everybody that laughed, thank you for listening. Everybody else is like, “why are they laughing?”

PF: Is it true that you’ve had the same phone number since 1993?

DB: Well done! Wow! Wow! Did you get that from Roxanne?

PF:  I mean—

DM: She’s always like, how is it possible that you have the same phone number? Yeah, yeah, it is true. It is true. And actually, so today, for some reason – this will also be fun for you to know – for some reason today, I was locked out of my Amex account. And I was just trying to pay my bill. And I went on, and I cleaned my cookies, whatever. I didn’t realize that cleaning them all and just eliminating everything would mean I’d have to put in every password again. So, I’m really a technophobe. And I’m like, “what did I do?” So, I called Amex, and I was on speakerphone, and Roxanne was next to me. And at the very end of the conversation, they said, well, “Thank you so much for being a customer now for 40 years.” And Roxanne was like, “what the fuck?” And I’m like, I’m 63. I got my first credit card at 23. I mean, yeah.

PF: So, it’s true.

DM: It’s true. Both of these things are true.

PF: Since 2005, with Design Matters, you’ve been exploring the paths of creativity, trying to understand how creative minds do what they do and how they design their own lives. So, it’s not anymore about just design, but it’s about designing their lives. Have you found any answers? Are there any common traits that everyone shares? Or each time, it’s different? Each person is truly unique?

DM: I would say that there’s both. I found there’s definitely some common denominators. I would say that the only people I’ve interviewed in 20 years – obviously, there’s a theme here of I Iike to do things for a long time. I’ve had the same phone number. I’ve had the same American Express account. And now I’ve been doing Design Matters – in February of 2025 it’ll be 20 years, which blows my mind.

There are a couple of common denominators. And I don’t want to offend anybody when I say this. But really, the only people that are really, truly, deeply confident are old white men. Old white, cis, heterosexual white men. That’s it. That’s it. Everybody else is still, even if they’re of a certain age, hoping that their best work isn’t behind them, hoping that they can still wake up tomorrow and find the muse and be fully engaged in their work.There’s a sense of – I don’t know if it’s necessarily insecurity, but certainly not feeling like it’s a given. Quite a lot of the older white men are like, “I’m good. Everything I do is great. And I’ll just keep making great things for the rest of my life.” And I’m like, “how does that happen?” How does that happen? But what I’ll also say is that the other side of that, for all of the other people that aren’t older white, cis, het men, is that there is a sense of longing for something bigger than they already have. Now, I don’t know if that comes from creativity. I don’t know if that comes from selfishness. I don’t know if that comes from humanity, just being human. But that’s, I think, one of the beautiful things about being creative is not knowing what’s going to happen tomorrow and wanting and hoping for something bigger than we have today. And when I say bigger, I don’t mean more money or more awards. I mean a real sense of doing something that you feel proud of.

PF: Talking about things that we expect and things that are unexpected, let’s talk about artificial intelligence.The guest of episode 55 of Parola Progetto was ChatGPT.

DM: Really?

PF: Yes. I had a conversation with AI for over three hours and managed to get just 15 minutes of podcast material. It was horrible.

DM: I’m going to make a terrible joke, but was that like ChatGPT as a white cis?

PF: I didn’t find the settings, but probably, yes. It was set on that. And believe me, it was exhausting because it didn’t say anything I didn’t expect because everything was so obvious and predictable. I learned a lot about ChatGPT. Like, for example, it starts asking you questions when it gets stuck. But I didn’t learn anything new about design or about the world or about people. So, I’m asking, what’s your relationship with AI?

DM: So not only am I a person that does things for a long time, I’m also a person that’s really afraid of change, which would make sense. I do things for a long time because I’m afraid to change. And so, I tend to approach anything that I don’t know from a place of insecurity and fear. So, if I don’t know something, I’m then going to pull back. And I’m working on this in therapy, but old dog. And so whenever I’m confronted with the new, I’m always a little bit guarded. Am I going to embarrass myself trying this new thing? Am I going to look like a fool?And so forth. And so initially with AI, I was like, everybody else, “Ooh, is civilization doomed?” And then last year, my students, my grad students, asked me if they could use AI to help visualize things. And I said, “Well, if you can use it for research, but I don’t want AI coming up with your answers.” And so, we had been commissioned for that thesis, for one of my thesis groups for the students, to reposition Archie Comics. And I don’t know if people are familiar with Archie Comics. You might be – the younger people might be more familiar with the television show Riverdale with all of the Archie Comics characters. And Archie Comics was started decades and decades ago. It’s about a group of teenagers in a predominantly white neighborhood, suburbia, and all of their various hijinks. One of our alums from way back had become an executive within the company that owns the brand and asked us to reposition and reimagine Archie for a whole new generation of consumers. And so, they went to Midjourney with the idea of trying to visualize an animated character within this sort of Archie visual language that wasn’t necessarily Archie. So, for example, what if Archie were an Indian person? What if Archie were a trans man? What if Archie was a girl? And so, the results that came back blew my mind. A lot of that had to do with the veracity of their prompts, which I learned about. I didn’t understand that you have to tell them to do– or them, tell it to do things. But they were almost instantly, as if they were natives in this capability, they were able to do something that really, really impressed me. And so that immediately put me in a, oh, this could be really, really interesting. And what I realized was that these were the same types of conversations that I was hearing in 1988, 1999, 1990, 1991, 1992 with the introduction of the computer. And everybody was talking about how computer technology was going to take the soul out of graphic design and how everybody was going to lose their jobs and there was going to be no soul in the work that we were doing anymore. That didn’t happen. There were a few jobs that were lost, but hundreds of thousands that were created. And industries that we had no idea were going to be developed, develop. And so, I was a little bit like, does anybody remember what we were talking about? Even as early as 1984 with Apple’s commercial for the Super Bowl. I mean, all of the same conversations. So, I’ve been a bit more excited about it than I think a lot of my elder siblings in our discipline. But I also can say that I’ve worked within it now.So I have two different kinds of experiences with ChatGPT and Midjourney because they do different things.What I can say is that a lot of my undergrad students use ChatGPT and I can almost always tell. And I’ve said this before, so if anybody’s heard me say it, I apologize for being redundant, but I think it still is worth saying.Anybody that is under 30 that uses the words “moreover” or “hence” in an essay is using ChatGPT. Right there, you can tell. And I try to warn them that if they’re using those words, everybody is going to know, but they do it anyway because, of course, they think that they’re different. I find that ChatGPT is really interesting for research, but it’s not good at all for any kind of original thinking at all. I have yet to find ChatGPT capable of original ideas. And I’ve played with it enough.

So, I wrote an essay recently for Commercial [Article] magazine. They have the one topic magazine issues, and the issue was on Brenda Starr, another comic character. And I have a long history with loving Brenda Starr. And they heard, the folks that run the magazine heard me having a conversation on the podcast with Linda Barry, who also loved Brenda. And so, they contacted me and asked me if I’d write an essay. And I did a lot of research. Took me a really long time to do it. And then I thought, you know what? I’m going to put in the prompts in ChatGPT and see what they come up with. And so, they were really obscure, like young girl living on Long Island in the 1970s, having been physically abused – trigger warning – who found a sort of solve in reading about and reading the life of Brenda Starr, a reporter, the comic strip. ChatGPT was like, “we can’t talk about things like abuse.” They just couldn’t go there. And then sort of understanding how you could find solace in a comic character was beyond their comprehension. There was just no way. All I got were facts about Brenda Starr. “Brenda Starr was started in the 1920s by Dale Messick.” I know that. And so, I wasn’t able to get anything with any kind of original qualities. And I did the same thing.

I just recently wrote an intro for Bob Greenberg and R/GA. They’re coming out with a big monograph. And I wrote something for them. And I also – I like to test now to see. Like, I have my finished manuscript. Let’s see what happens. And there’s nothing that would be palpably entertaining. All it is facts, some of which are wrong. You know, you mentioned Wikipedia. Wikipedia thinks I’m younger. I’m like, cool.

PF: OK, great.

DM: Not going to change it. I wouldn’t know how to change it. But I’m glad that they think I’m younger. I’m cool with that. So, you have to be really careful with the information that you’re getting. So that’s ChatGPT.

Now I’m going to go to Midjourney. So, I recently finished working on a book. And the book is not anything I ever thought I would write. It’s called “Love Letter to a Garden.” It’s going to be out in April. And really, the whole opportunity came about because of a whole slew of visual essays that I started writing in 2018, 2019, 2020. I wrote a piece, actually, I designed a visual story that also had narration for the TED conference in 2021, when it was fully online. And it was a series of love letters. One was a love letter to storytelling. One was a love letter to travel, because we couldn’t travel anymore. And one was a love letter to gardening. And then I wrote another piece, another visual story, after going to Antarctica to try to see the total eclipse of the sun, which I wasn’t able to do because of cloud cover. But I wrote this piece about that. A gardening editor at Hachette saw those pieces, contacted me, and asked me if I’d be interested in writing a book, a visual essay book about gardening. And I’m like, “I spent most of my gardening career trying to get roses to bloom in shade!” For anybody that is a gardener, you know that roses don’t grow in shade. And so clearly, any gardener that would be looking at anything that I would do would be like, how did this happen, like rolling their eyes. So, I’m like, no, I can’t really write a book about being a gardener. I can only write a book about my quest to be a gardener, because it’s really been a 40-year quest to try to have a garden. And I also had a lot of memories from my youth, very young, to try to bring to life in my quest. So, what was my history that led me to wanting even to have a garden? And I’m an illustrator if I can have something to reference. I’m not somebody that can just draw this beautiful man sitting in front of me just by looking at, I need a photograph. I need to study it. I need to figure out how to use that to help craft an illustration. And so here I was trying to come up with these memories to draw these memories, and I couldn’t do it. So, I decided to go to Midjourney and put in all the prompts. Alleyway in Borough Park, Brooklyn in the 1960s with a vanishing point that leads to a waterfall.Doesn’t exist, didn’t even happen, but I sort of remembered being in my grandparents’ backyard in an alleyway at five or six years old, playing and walking and finding a waterfall. I was so convinced that there had to be a waterfall there from this memory that in 2008, when Google allowed you to see the satellite views of streets, I went, put my grandparents’ address in, and was like, there’s got to be a waterfall here. Like, there’s a waterfall in Brooklyn. No, there is not. There’s no waterfall. And so, with those prompts, I was actually able to get enough reference from about three or four different results to put it all together to use it to make a watercolor.So, I had that reference. That to me was miraculous. It was miraculous. So long answer to a question about AI: some of it is terrible, and some of it is miraculous.

PF: Because you use it as the tool it should be.

DM: I don’t know. I mean, it’s hard to say. So many people have been asking me to do interviews with people at conferences about AI. So, I’ve had to learn a lot more. So, for example, I didn’t know that doctors now are able to gather enough data with AI to be able to fairly accurately predict whether or not somebody might have a chance of getting Alzheimer’s from an eye exam. And so again, that feels miraculous. Seeing a resume or a cover letter written by an undergrad graphic design student using ChatGPT, really terrible. So, I think we’re very early into this sort of new technology, both of which is terrible and miraculous. And like almost everything else humans do; we have to choose wisely.

PF: You mentioned memories. I’m wondering, do you have a design madeleine? I mean, is there an object, a piece of graphic design, or a logo, something from the design world that takes you back to your roots or your earliest memories?

DM: It’s a wonderful question, Paolo. Brenda Starr, so in writing this essay, I was in the 1970s. I was in seventh grade and there’s no computer. I knew that the creator, illustrator, and writer of Brenda Starr was Dale Messick. But I didn’t know if Dale Messick was a man or a woman. And Newsday, the local Long Island daily newspaper, had a helpline. You can write in questions and they would publish them. And it happened to be on the same page as “Dear Ann Landers,” which was the advice column, which was literally right next to the comic section. And so, I wrote this question in. And they published it. And when I was writing the essay, I thought, oh my god, what if it’s still somewhere in the archives of Newsday that I can find that page? And I found it. And so, seeing Newsday and seeing all of the – and then I read 10 years’ worth of Brenda Starr strips.But what happened was, when I found it, they didn’t publish people’s full names. They published only the initials. And at that particular time in my life, my mother had gotten remarried. My parents got divorced when I was in fifth grade. And so by seventh grade, my mother had gotten remarried. And I hadn’t seen my biological father in years. And my mother wanted me to change my name, my last name, to her second husband’s so that we would all have the same name. And so, I did. Now, he ended up being like a monster and is still the reason I’m in therapy all these years later. But so, I changed my name to his last name, which started with an A. When I found the column, it said “D.A. East Northport.” And that was like whoosh. And suddenly, I was in seventh grade with a ponytail waiting on my stoop for Newsday to come every day. So, I could read Brenda Starr and go into this world of the other. I could read – I know I read the newspaper, and I read the Helpline and Landers. And suddenly, my curiosity, my sort of acquaintanceship with my curiosity became familiar.

PF: And how did you realize that your curiosity could be fed through design? Because you’ve had several professions, brand designer, graphic designer, and podcaster.

DM: It really is just because I’ve been trying to make it all these years. Since like, I’ll try that. I’ll try that. I’ll try that. I’ll try that. Then you get old enough, and you start to get a reputation for trying everything.

PF: But design is always there. Why so? Why didn’t you choose just art?

DM: Oh, because I didn’t have the courage. I didn’t think I was good enough. I didn’t think I was good enough.And I still battle that till today. I didn’t think I was good enough to, I didn’t have the courage or the confidence or the selfishness to do what I wanted because I just didn’t think I was good enough. And I had these skills that I had learned in working on my student newspaper that was basically out and paced up when everybody was doing things on a drafting table, pre-computers. And that was the only thing I knew how to do. And I graduated wanting to do these other things, but then also wanting to be in New York and Manhattan and wanting to be able to make enough money to pay rent without being a bartender or a waitress. And so, I became a graphic designer.

PF: You have always been extremely consistent in one thing. The title of your 2017 talk at 99U is simple and insightful. And it goes, “Anything worthwhile takes time.”

DB: Takes a long time.

PF: I’d like to quote also something you said to me. “The longer something takes, the longer it will last.” So how do you find this balance between spending a lot of time doing things, but also the speed that is needed in our lives and also in your job?

DB: Well, to some degree, you don’t have a choice. If things take time, you can’t really speed it up. The more you try to speed something up, my guess is that the less authentic it’s going to be. And the more rushed it’s going to feel. And people will sense that. I mean, if I was able to kind of come out of the gate, like a Jessica Walsh or a Jessica Hishe or a Timothy Goodman or a Paola Antonelli, I would have had a very different career.But that just wasn’t in the cards for me. I spent my 20s, so all of the 80s – you probably have read this because you’ve done such good research – doing what I felt were having experiments in rejection and failure. And then my 30s was really sort of navigating a more corporate career. I didn’t become president of Sterling Brands until I was 38. And I didn’t start Design Matters until I was 43. And so, I think, for me, it’s just been head down, sort of ride through the headwinds, and hope that where you’re going will be meaningful. But it’s also taken a really long time for me to even try to be an artist or an illustrator or a writer. I had to go through all of those decades working as a brand consultant, doing brand strategy, working in corporate communications. Almost all of my career was working for clients, bringing their visions to life in the form of logos and packaging and shelf presence and market share. And all of those things have brought a lot of success and financial rewards to my life. But it was because I felt like I was losing my creative spirit when I was 43 that I turned to making Design Matters as a Hail Mary for my creativity, never ever, ever realizing that I’d still be doing it 20 years later. But then again, I have a credit card that’s 40 years old.

PF: And the beginning of Design Matters is wonderful. I mean, you’ve told this story, I think, at least 2,000 times. But I want to hear it from your voice again.

DB: Which one?

PF: I mean, it was not 100% your idea. It was something that was proposed to you to start a radio show, right?

DB: Oh, yes.

PF:  And then you embraced change.

DB: Yeah. So, I got a cold call from a fledgling radio network, online radio network, called Voice America, which is different from Voice of America, the very right-leaning Republican rag. Not that I have political opinions that I should be sharing, but whatever.

PF: We’ll talk about that later.

DB: Oh, good. And so, yeah, I got this call out of the blue. I thought he was offering me a job as a radio host, which was really exciting because I knew a lot of people at my radio station in college but was never a DJ. And it sounded really glamorous. And there was an old show called Northern Exposure from years and years ago.And John Corbett was this DJ. And he’d always tell these fun, This-American-Life-type stories. And so, when I got this call, I thought, “Oh, I can be just like John Corbett in Northern Exposure and tell these stories.” And then I realized I could do whatever pretty much I wanted, as long as I paid them for the airtime. So, it was this ultimate vanity project. And that will tell you just how desperate I was to do something creative because they were giving me a little bit of creative freedom, although they really wanted me to do a show about branding.And I didn’t want to do a show about branding. I had done enough, or I was doing enough with branding, but was actually able to sort of sneak it in through the lens of design. So, I started paying them. I was making good money in branding and thought, you know what? I’m going to invest a little bit in myself. And I did 13 episodes.And people really seemed to like them. And suddenly, Stefan Sagmeister said yes. He’d be on the show. And Paula Scher said yes. And Milton Glaser said yes. And I was like, oh, this is really, I can meet all of my heroes.And I can just be asking them the questions, so I don’t have to reveal how little I’ve done or how little I’m proud of or whatever. I can just be really curious and ask them lots of questions about how they became who they became. And that’s really how it started. And I just kept doing it because I do things for a long time. And then about four years in, 100 episodes, Bill Drenttel, the late, great Bill Drenttel, one of the founders of Design Observer, asked me if I wanted to bring the show to him, to Design Observer, with the proviso that I improve the sound quality. Because when I started the show in 2005, I would sit across from my guest in my office in the Empire State Building, which gave me legitimately the ability to say, “broadcasting live from the Empire State Building”, because most of the radio stations that say that just have their antenna on the top of the Empire State Building. They’re not housed in the Empire State Building. I was actually housed in the Empire State Building. Ask Paula Scher. She was there. Giorgia [Lupi] can ask her because Georgia works with her and is her partner at Pentagram.

So, in any case, I would sit literally like this at my desk in my office with a handheld telephone set. And so would my guest. Now, I don’t know if anybody has ever used a handheld telephone set here in this room. But when you both talk on the phone at the same time, there’s an echo. And so that’s what I contended with in those early years. The sound was unbearable, truly unbearable. I don’t even know why people were listening.But I think it was only because of the quality of the guests that I had. I mean, it was so unbearable that when I did eventually put it up on iTunes, which is where Apple Podcasts used to be, people would say, “Great content. What the fuck is wrong with the audio?” And I’d be like, “I don’t know how to make it any better. I’m a brand consultant, not a DJ.” And it felt like the people I was working with at Voice America at the time were, it was like doing an episode of Wayne’s World with Wayne and Garth in a basement in Arizona, like doing bong hits while I was talking to Milton Glaser. And so, Bill was like, “I’ll bring the show to Design Observer, but you have to do something about the sound quality.” And I’m like, “Bill, I don’t know how.” And he’s like, “Let me introduce you to a producer.” I was like, “OK.” And so, he introduced me to Curtis Fox, who was at the time doing a podcast for The New Yorker and the Poetry Foundation. And he became my producer. And we, of course, have been working together ever since.

PF: In all the things that you have discovered about designers and creative minds, is there any habit that you just can’t stand, something you’d love to make disappear with a magic wand in their attitude?

DM: No. I can’t think of anything. I mean, I’m sort of sad that – maybe sad isn’t the word. I’m a little bit worried about the whole notion of personal branding as somebody that’s spent almost my entire career in branding. I have a real issue with someone wanting to build their personal brand, which people ask me about a lot. And I think that building a personal brand is an oxymoron. Brands aren’t personal. People can own brands, and they can manage brands. They can grow brands. They can create brands. But to be a brand, to me, feels like you’re taking all of the soul out of being human, all of the qualities that we try to build into brands, consistency and authenticity. As soon as you use the word authenticity, you know it’s a lie.

PF: Of course.

DB: And I mean that, sincerely.

PF: We care about your privacy, right?

DB: Right, please. Come on, as if. And so publicly traded companies that own brands have a fiduciary responsibility to the shareholder. Once you have a financial responsibility to anyone, and that’s your priority, where does authenticity fit into that?

PF: Yes.

DB: Where do politics fit into that? And where does science fit into that? And so the very things that I think make designers designers – abstract thinking, messiness, risk, experimenting. When was the last time you heard a brand really talking about experimenting? And so, I have concerns about where that can lead us. And so, I think people should be maybe more concerned about their character and their reputation than their brand.

PF: Do you have a definition of success?

DB: Contentment. Being content with what you have.

PF: A common question on podcasts is, what would you say to the 10-years-old you? But I’m not going to ask this question.

DB: Well, it’s different, because most of the questions I hear in that realm are, what would you tell to your 30-year-old self? But that’s different from a 10-year-old self. The 10-year-old self, that’s actually the first time I’ve heard that.

PF: Should I ask this question, too?

DB: No.

PF: OK. I’m going to ask you quite the opposite. Today, we are recording, and it’s October 22, 2024. This episode will air in three weeks, on November 15, 2024. On November 6, Americans will be in the United States. Americans will choose their next president. What would you like to say to the Debbie of November 15, 2024?

DB: Depends on the direction. If it goes blue, thank God. If it goes red, arrivederci! I don’t know what I’m going to do. It’s terrifying. And I hope that everyone here, everyone listening, is like-minded and worrying about the outcome enough to make their choice known and counted. What scares me even more than the outcome is that it’s this precarious, that it’s not a no-brainer, that we’re not just all expecting a landslide of epic proportions, that we’re worrying two weeks before with a result that might end the whole democratic process that we’ve had for 250 years. This great experiment for a dictator, a narcissist, a rapist, a criminal, a felon? How is this possible?

AUDIENCE: He’s a white guy!

DB: Yeah, right? Thank you. Symmetry in this conversation. He’s an old, white, cis, het dude. But there are some that are OK, some of my brothers.

PF: Debbie, after all these years in conversations, have you figured out the meaning of life, or at least the meaning of design?

DB: Paolo, these are intense questions! First of all, why would anybody care what I think the meaning of life is?

PF: The meaning of design.

DB: Meaning of design?

PF: The role of design today.

DB: The role of design today is to help us open the doors to as much truth as we could possibly find that science hasn’t given us. Off the top of my head.

PF: Debbie, in preparation for the Parola Progetto events in New York, I reached out to previous guests and asked them if they had questions for you, Paola Antonelli and Massimiliano Gioni. I received many, many responses, and I had to select. It was very, very hard. The following questions, they come from those who preceded you. The first question is from Andrea Incontri, fashion designer. Let’s talk about diversity. The term comes from Latin, and it means turn “elsewhere”, or “different direction”. How much of this different direction is a space to explore, or is there a risk that diversity could lead to a kind of new conformity?

DB: Wow. This is like way above my pay grade! I mean, I fundamentally disagree with the idea that diversity will bring a new kind of conformity. We’re nowhere near that. Nowhere. We’re generations away from that even potentially happening. So maybe far down in the future, 50, 60 years from now, maybe. But right now, I mean, come on. We can’t even get a woman elected president. That’s not even – I mean, hopefully we will, but haven’t yet. And there’s been 46 of them. I think that diversity is the key to all creativity. It forces you. It inspires you. It influences you to think broadly, more broadly than you’re capable of. And without it, we’re just amoebas.

PF: Next question is from Francesco Pavia, entrepreneur. Have there been any epic surprises that shaped your professional path?

DB: My success was an epic surprise.

PF: Wow.

DB: And it still is every day. I feel so grateful. So grateful. I can’t even begin to tell you how grateful I feel that this quest to try to find some value in myself and what I could offer has been accepted. And I mean that sincerely. It’s not a humble brag. It’s genuine, a sense of real gratitude.

PF: Next question from Simona Flacco and Riccardo Crenna, founders of Simple Flair. Can design still be a tool for telling stories today? Is it a storytelling tool still?

DB: I hate the word storytelling…

PF: What other kind of word should I use?

DB: Design. And then once we start design and strategy, design and storytelling, I mean, I’ve lived through decades now. There’s always like a buzzword. Yes, of course, design tells stories. Humans tell stories. Our symbols are stories. These are things that we’ve had for 10,000 years. The walls of Lascaux, the caves are stories. So of course, everything we do is embedded in some type of story we’re telling ourselves and sharing with others.

PF: Debbie, it’s time for La Raffica!

DB: La Raffica!

PF: Raffica means burst.

DB: You have the best voice.

PF: Really? Oh my god! Debbie Millman told me I have the best voice, guys! Can I put this sentence on my resume?

DB: Yeah. I love the way you roll your R’s. It’s so beautiful.

PF: Thank you. Thank you. I need a second to [process] this.

DB: His husband’s here. Don’t worry.

PF: La Raffica is a classic segment of Parola Progetto. Raffica means burst, and this round features a rapid fire set of 10 either/or questions. We’re looking for sharp answers, but there are two bonuses. You get one chance to pass and one opportunity to elaborate.

First question, a walk in Central Park or along the Malibu coastline?

DB: Central Park.

PF: Romantic night out, cinema or theater?

DB: Theater.

PF: Before going to bed, novel or nonfiction?

DB: Nonfiction.

PF: Last minute vacation, Europe or South America?

DB: Europe.

PF: Good.

DB: Paris or Tuscany? Tuscany.

PF: One impossible guest for Design Matters, Pablo Picasso or Marcel Duchamp?

DB: Pablo Picasso.

PF: Handmade or machine made?

DB: Handmade.

PF: An artwork for your home, a big one, Da Vinci or Monet?

BD: Da Vinci.

PF: Dinner with five or dinner with 50 people?

DB: Five.

PF: Minimalism or maximalism?

DB: Minimalism.

PF: Serif or San Serif?

DB: Pass.

PF: OK, this was the last one for La Raffica. You didn’t have the necessity to elaborate.

DB: I think everybody’s probably tired of me talking at this point.

PF: I’m not. I’m the host. So… Do you have questions from the audience, by the way, since you’re here, guys?

AUDIENCE: Thanks a lot for that talk. You said that design aims to highlight some form of truth or to find it.And I would like you to develop that, because it triggered a lot of questions in me.

DB: I think the best designers have the ability to give us a sort of view of what’s possible. Humans are the only species that can scenario plan, can think about options, can think about this or that. And design is very much a decision-making discipline. We’re deciding Serif or San Serif. And I think that we can help people or lead people to understanding things that they don’t already understand. And it’s a very unique discipline in that we can do that. And I think that we have a responsibility to help people know more than they already know, to open people’s minds up to possibilities. And that’s sort of what I mean by even beyond or alongside what science can do. Science is very empirical. Design is very subjective. The very things that excite and delight some people are the very things that outrage others. But if we can help people navigate through that to understand more than they do without it, it gives us, I think, an opportunity to grow our humanity. Does that help?

AUDIENCE: Do you have a concrete example to make things a bit less abstract?

DB: Michael Beirut, 25 years ago, did an amazing postcard. It was the butterfly election form that determined whether Bush or Gore were going to be president. And because the design was flawed, a lot of people voted in a way that they didn’t intend. And he created a postcard that just had a photograph of the election form with the headline, “Design Counts.” Everything we do is sort of cinematic in that it creates this domino effect of this happens, and then this happens, and this happens, and this happens. And designers craft those dominoes because we’re crafting information. We’re crafting communication. Everything we make has some type of ramification and result in culture. It’s different than fine art. We’re actually doing things that motivate people to buy something or not buy something or believe in something or not believe in something. And I think that is probably the single most important aspect to our discipline, is that we’re leading people to think. We’re giving them the opportunity to make choices, to choose. And that, to me, feels super, super important and leads us to where we’re going to go in the same way that science leads us to where we’re going to go. I think they’re two of the most important disciplines, practices that we have. Thanks for making me think about it.

Hi Giorgia. Giorgia [Lupi] has been on Design Matters five times. I was thinking about when I saw you, I’m like, how many times?

GL: And by the way, she does her research. I think my first one you started by, “Is it true that you were playing heavy metal in a band in high school?” which is nowhere to be found on the internet, by the way. Anyway, thanks for the amazing conversations. I think one of the things that I remember the most that you said, and you were probably quoting somebody else, and I might even be butchering the quote, but it’s about courage. And it was something along the lines of “courage is confidence over time.” And you touched upon, in all your guests, having a subset of people that feel particularly, I mean, not necessarily maybe courageous, but confident about where they are, how they put themselves out there. And to me, this is very fascinating. A lot of us designers and artists face it every day. And anything else that you have learned in 20 years of interviewing people, but also in your amazing career in terms of courage and confidence, and what does it mean to share things that you do every day and being confident that they’re good enough? So, anything you can say about that.

DB: I know exactly who you’re talking about. It was Dani Shapiro. And it was probably at least 10 years ago.And it actually happened after the podcast. And she came into my office. And at the time, I had a stack of books on my desk that were all about confidence, a whole slew of books had come out that year about confidence, self-help books, and I had gotten them. And they were sitting on my desk. And she looked at them and she said, “Oh, confidence is so overrated.” It was like the Holy Grail to me. And she’s telling me it’s overrated. And I said, “Why do you think that?” And she said, “Well, I think that what’s so much more important than confidence is courage to take the first step into the unknown.” And I was blown away by that statement and really felt that that was true, that courage was so much more important than confidence because of the faith that’s required in taking that first step. And so, then I spent like the next year thinking about this and realized that we are born not knowing how to do pretty much anything. You know, we can’t walk, we can’t talk, we can’t clean ourselves up after pooping. You know, there’s like so many things we’re incapable of doing and we try them anyway. You know, we try to walk, we try to eat, we try to, you know, we have to learn, you know, potty training and all of that. And so, we take it for granted that if we are able-bodied, we have walking confidence. If we can speak, we have talking confidence. And so, the idea that when we want to try something new, that unless we’re really good at it at first, we sort of give up or we feel like ashamed or embarrassed or whatever it is, you know, we have to think about what it means to try something and then get better at it over time. And so in that year of really thinking about, well, what does it mean? What does confidence really mean?How do you get confident? And what I came up with was that confidence is really just the successful repetition of any endeavor. So, we have walking confidence or talking confidence. We have car confidence if we know how to drive. Once, you know, we learn how to drive, we are nervous when we’re learning. No one expects to get into a car and be able to parallel park on the first try. It’s just, you develop that confidence over time.What’s interesting is that you tend to lose that confidence for a bit if you have an accident or you get a ticket.And then you have to build up that confidence again over some time when you, you know, after getting a speeding ticket, you don’t speed for a little while and then you get confident and then you’ll speed a little bit.So, I think that the pressure that we put on ourselves to be good at something right out of the gate is very harmful to growth. And so, I think that, you know, that comment from Dani has stayed with me and not to say that I still don’t want, you know, I don’t like to do things I’m not good at. And I hate that I cannot be good at things Actually, Roxanne says that because we play Scrabble together a lot and she says I’m a sore loser and a sore winner. I’m a sore loser when I don’t like losing and then when I win, I feel guilty. I know, I’m, you know, therapy

So that I think is really important. But then the other thing, and this is something I learned in the podcast and it was said to me in the studio and I’ve said this before, but it’s so, I think, worthwhile saying again. And it was when I interviewed David Lee Roth. David Lee Roth, the former lead singer of the band Van Halen and he has a reputation of being a real jester and a real showman and very flamboyant. And when I had him in the studio, he was really playing to the, I had my students sitting outside the sound studio, they were listening through the speakers, and he was playing to the audience. He was very much a jester. And he was there ostensibly to talk about his tattoo company that he has Tattoo Ink. But of course, I had to ask him about what it was like to be, you know, the lead singer of Van Halen, especially since I lived through their fame. And in 1984, when 1984 came out, their album, you know, along with David Bowie and Modern Love and Thriller and Bad, you know, those were the biggest albums of that time. He was one of the kings of the universe. The biggest tour, the biggest album, the biggest video. And so, I asked him what that felt like. What did it feel like to be like the coolest dude on the planet? And he stopped being a jester. And he said that you have to be really careful when you get to the tallest mountain in all the world. Because when you get to that top, it’s always cold. You’re almost always alone. And there’s only one direction. I realized in that moment that I had been trying to race up this mountain my whole life in the headwinds. And that maybe it was okay to sort of take your time, one step at a time. You know, there are a couple of people out there that are still doing the best work of their lives in their sort of elder statesman kind of position in the world. In the design world, certainly Paula Scher is still doing some of the greatest work of her life. I’d like to think that at some point, I could be really excited about where I could be going without knowing where I’m going, then have to sort of plot every moment of the path. So, I think that’s a good thing to think about. Slow steps up the mountain. You don’t wanna peak before you have with that much more time in front of you. I’d like to think I’ll peak the day before I die.

PF: Oh, wow.

DB: Right, wouldn’t that be fun?

PF: That would be great, yes.

DB: Go out on a high like that, yeah.

PF: Should we go with the final question?

DB: I thought that was a nice place to end, right?

PF: Yes, definitely.

DB: Peak the day before we die.

PF: That could be the title of the episode. The classic final question of Parola Progetto. Could you recommend a book, only one, that has been important to you, one that we should also read, all of us, if we had to go to the bookstore tomorrow morning? Which book should we buy and read it immediately?

DB: I don’t know that I wanna be nepotistic, but of course, “Hunger” by my wife, Roxane Gay. One book… Oh my God, there’s so many. “Love in the Time of Cholera” by Gabriel Garcia Marquez.

PF: Thank you, Debbie. Thank you very much.

DB: Thank you, Paolo.

Episode recorded in Brooklyn at Salotto NYC on October 23, 2024, and published on November 15, 2024.

The transcription was generated using artificial intelligence tools and subsequently edited by the author.

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