On this episode of Dare to Lead
In this episode, I’m talking with the legendary Debbie Millman—designer, author, educator, curator, brand strategist, and host of the long-running, multi-award-winning podcast Design Matters—about her new book, Why Design Matters: Conversations With the World’s Most Creative People. It’s a conversation about creativity with one of the most creative people in the business, where she answers a lot of direct questions like, What is good design? What are the politics of curation and how is it different from discernment? What gets in the way of a creative life? We also, of course, talk about shame and worthiness, and some of her answers are just incredible. I can’t wait for you to hear this.
Listen to the episode
Why Design Matters: Conversations With the World’s Most Creative People by Debbie Millman is a curated anthology by the Design Matters award-winning podcast host and branding visionary. This salon in book form features text from Millman’s conversations with the world’s most creative minds, thought leaders, and intellectuals, each with an introduction from Millman. It’s a visually stunning, often revealing, and always enlightening work that readers will turn to repeatedly for inspiration.
Design Matters With Debbie Millman is one of the world’s very first podcasts and the first ever about design and an inquiry into the broader world of creative culture. Broadcasting independently for 17 years, the show is about how incredibly creative people design the arc of their lives.
“Love, Life, and the Pursuit of Creative Space” Unlocking Us podcast episode, with Roxane Gay and Debbie Millman
Brené Brown: Hi everyone, I’m Brené Brown, and this is Dare to Lead. Can you hear me grinning? It’s so obnoxious underneath talking. You know, when you can tell someone smiling the whole time they’re talking, that would be me right now. Why? Because I’m talking to my friend Debbie Millman today, we’ve had her on Unlocking Us, I’ve been on her podcast. Dang, she’s incredible. Designer, educator, curator, brand strategist, host of the long-running multi-award-winning podcast Design Matters, author of seven books, including her new book Design Matters: Conversations with the World’s Most Creative People.
BB: Today, we talk about everything from curating this new book. I actually think she almost invented podcasting, when you hear the story about her first kind of podcast that it wasn’t even called a podcast back then, you may agree with me that she maybe invented this art form. We talk about her new book. We talk about the politics of curation, what is curation, how is it different than discernment. We talk about what is good design, talk about what is the soul of a creative life, what gets in the way of a creative life, we of course, talk about shame and worthiness, and some of her answers, just incredible, I can’t wait for you to hear this. I’m glad you’re here. This is one of those things that if you’re at home, you need to grab the big mug of tea, like in the commercials with your hands wrapped gently around it and you’re wearing a wool sweater with extra-long sleeves, this is that kind of podcast.
BB: All right, before we get started and jump into this great conversation with Debbie, let me tell you a little bit about her, she has been named one of the most creative people in the business by Fast Company, and one of the most influential designers working today by Graphic Design USA. She is an author and educator, a curator. Again, the host of the podcast Design Matters. This podcast is incredible, and the people that she’s talked to is kind of mind-boggling, because she’s been doing it for so many years, and the podcast has actually won a Cooper Hewitt National Design Award, six Webby nominations, and an Apple Podcast best overall podcast designation. In 2009, Debbie co-founded with Steven Heller, the world’s first graduate program in branding at the School of Visual Arts in New York City. Her books are incredible.
BB: This new book, I’ve got to tell y’all, this is, if you’ve got a creative, a designer, an art person in your life, I cannot even imagine a better gift than this book. It’s incredible, it’s called Why Design Matters: Conversations with the World’s Most Creative People. It weighs 424 pounds, I’m exaggerating. But it’s a honkin beautiful full color book. Debbie is a frequent speaker on design and branding. Her Ted talk was ranked one of the best Ted talks of 2020, and Debbie lives in New York and Los Angeles with her wife Roxane Gay, another favorite of everyone here. And I just want to add a little content warning that we are going to talk about sexual abuse, surviving it, overcoming it. That will be part of the conversation between me and Debbie.
BB: Debbie Millman.
Debbie Millman: Brené Brown.
BB: I’m so excited to talk to you.
DM: I feel the same way. I have goosebumps all over.
BB: So do I. Okay. I don’t even know where to start, so I’m just going to do a bunch of non sequiturs. The first thing I’m going to say is, I had the funniest pre-call with Laura Mayes who produces the podcast with us, and we were like, “Okay, what are your thoughts about this book?” This is our conversation we have before the podcast. And there were no words, just sounds for probably like 60 seconds like mmm, no, mm-mm, oh, woof, woo, wow, mmm.
DM: As long as they weren’t bleh!
BB: No, there was no bleh! This book…
DM: Thank you. It was a labor of love; labor being the operative word.
BB: This book. It’s incredible. It’s you in a book. How much better does that get?
DM: Oh Brené. It doesn’t get… Well, it depends on how you feel about me, but if you like me then it’s a good thing.
BB: Yeah. We love you around here. It’s a good thing. I have to tell you, some of the designers and artists that we work with externally that we partner with and collaborate with, of all the people I talk to, including President Obama, they’re like, “You’re talking to De… Debbie… De… De… Debbie Mill… ” It’s like you are a legend in this design world. How did this happen?
DM: It’s a big, big mystery to me, frankly, Brené, because I struggled so much when I was younger that the idea that I would have any kind of greatness in anything at this age would have been something that I would have thought, “Gee, not possible for this girl.” I guess a little bit of luck, a lot of hard work, maybe a lot of luck, a lot more work, and I think a dogged perseverance in the hope that I had one notch more optimism than shame.
BB: Say that again.
DM: A lot of people have asked me over the last couple of years, what gave you the strength to continue in the face of the many failures and rejections and humiliations and various other bad things. And I really had to think about it a lot. And I think that in the grand scheme of my life, what I’ll be able to wholeheartedly say, a word that I use now much more because of you, is that I have one notch more hope and optimism than I do shame about what is possible for me. Just one notch, that’s all I need.
BB: God, I just want to pause for a second. We just need one notch more.
DM: Yes, because I don’t know that anybody’s shame or fear, certainly not their fear, because that’s sort of hard-wired into us, and that’s just not something we can ever expect to just eradicate in our lives, but the shame that we all carry is very hard to unload, and I don’t know anybody that’s really ever been able to say “Bye-bye, it’s gone forever.” But if you know that, even with that, you can still have some hope about what’s possible, you can still have a lot of hope about what’s possible, and you can still have a lot of shame. But I do feel at the end of the day, when we have that little balance, that little weight, like the legal scales of just one notch more hope about what’s possible. And that keeps me going.
BB: Phew! It’s so powerful because like you, I get asked a lot “Did you think that this would be your career, or did you think you would have this kind of success around this?” It always comes down to something very similar to what you say, I just say, “I’m this much more tenacious than failure. Not a shit ton. Not this much, but I’m just this much.” And I think maybe there’s a myth that success means having it figured all out, it doesn’t mean just having just barely a centimeter more hope about what’s possible.
DM: You can see that now in the Olympics when people win by a 10th of a second.
BB: Oh my God, yes.
DM: And that’s all it takes, it’s just that millimeter, that teeny, tiny nanosecond, and that gives you the gold medal. That’s all you need in your life as well, that one teeny, tiny spoonful of hope.
BB: All right, let’s back up a little bit and I want… Will you tell us your story?
DM: Well, I just turned 60, so it’s a long story, but I’m going to give you some highlights, some excerpts.
DM: I’m a native New Yorker, I’m speaking to a native Texan, so we each have our little corners of the world that we love the most.
DM: Yep, I’ve lived in all the Boroughs except the Bronx, but there’s still time. And I grew up in a very turbulent household, my parents probably never should have gotten married to begin with but divorced by the time I was eight. My mom was never comfortable being on her own, ended up marrying somebody within a year, even though it was my dad that actually had the affair and ultimately precipitated the divorce. My mom married somebody she shouldn’t have. He was a dastardly person, he was very physically, emotionally and sexually abusive. Sexually abusive to me, and physically and emotionally as well, but also physically and emotionally to my brother, fortunately was not sexually abusive to him. So that lasted for quite a long time in my life. Four years. At that point, I was only from eight to 12, in the grand scheme of things, it’s not that long, but at that short time, it was.
BB: It’s a lifetime.
DM: Yeah, and then her next paramour was also abusive to me. But at the time this was all happening, this was in the ’70s, this was not a topic that people talked about. So frankly, when it was happening to me, I thought I was the only person in the world that was happening to. It was such an anathema to me that this could exist. And I was told by him that if I told anyone he would kill my brother and my mother, and that was just not something I wanted to be responsible for. And so I didn’t say anything until they finally did get divorced, and he ended up raping his daughter, his biological daughter, who then came to my mother told her and then called the police. While it was happening to me, because I was so young, and didn’t know that when you first get your period, you sometimes don’t get it again, I thought maybe I was pregnant and told my mother that I had been assaulted at school. She took me to a doctor who didn’t believe me, and because of the scar tissue that he saw and thought that I had a long-term boyfriend that I was just afraid to tell her about.
DM: So those were the times. Those were the times that we were living in. I finally got away, got to college, and then really began my life. I was able to get away from home, I was able to get away from the abuse, and my primary goal at the time was safety and security, safety, and security. Needed to make my own money, take care of myself, have my own agency, to be able to do what I needed to do. The problem being that it’s hard at the time you’re making these decisions to factor in both safety and security and living a creative life, especially if you need to pay the rent. So for me, it was, I really want to be an artist, I really want to be a writer, I really want to do all these creative things, but I also want to live in Manhattan and pay my rent, and so therefore I’m going to go into commercial art. And that’s what I did and did it for a very long time.
DM: Struggled really hard the first 15 years. Just one rejection after another, did try to go to graduate school, got rejected from Columbia School of Journalism, got rejected from the Whitney Independent Study art program; did really, really poorly at a lot of different jobs, and then finally, finally quite by accident found my way into a branding consultancy, where I was hired as a salesperson, which was the lowest rung in the commercial world that you could have even below designing direct mail, doing sales. And this is nothing against salespeople, because I have to tell you, that’s how I ultimately made my career, sales was the way in. Because you’re the rainmaker, you’re the money man, so that’s what I became. And because I guess I was so desperate to please and do well and make a name for myself that I finally, after 15 years of struggling through the commercial world of design, did really well selling design programs as branding projects in corporations.
DM: And so I would say by the 15th or 18th year of my career, I hit that zone, I hit the zone, and then started working at a company called Sterling Brands, and was hired as a salesperson, and then ultimately was promoted to president, and then to partner and then I was very instrumental in helping sell the company to Omnicom in 2008, which you would have thought at the time might have given me the golden keys to finally then begin being an artist and a writer and whatnot, but I was still too scared. I was worried that if I left that I would… You don’t really think when you’re leaving things about all the things you might get because they’re uncertain, you don’t have that crystal ball that says “Well, if you do this, then you will find true love.” It’s more like, “If I do this, I will never have anything again. I will die penniless in the street,” because that’s always been the fear.
DM: And so I stayed another eight years, just when I was about to leave, I was offered the CEO position, and then my brother was like, “She’s never leaving. That’s it, it’s a done deal. She’s going to die there.” No, I actually did, I finally decided that… Actually, my partner, the CEO at the time who was offering me this job, it took me so long to decide, he said, “Debbie, if it takes you four months to decide to do something, you probably don’t want to do it.” And so in 2016, finally, finally, I forged off on my own and was also concurrently running a branding Master’s degree program at the School Of Visual Arts, which I still do, so I don’t want anybody to… I don’t want to pull the wool over anybody’s eyes and say, “You know, I let go off the trapeze and was able to fly.” I actually let go of one rung of one trapeze and held on to another where I was still doing things that were helping me stay alive.
BB: Can I ask you this question about that four-month decision-making period?
BB: Were you aware during that decision-making time, that if you said yes, you were saying no to other things?
DM: There were moments in that four months where that did occur to me, what I was trying to talk myself into at the time was the possibility that I could do it all, that I could pursue all of these things that I wanted to do, that I told myself I would do if I wasn’t doing this corporate job and running a graduate program and doing the podcast and doing all the things that I was doing, most of which I loved. The corporate job was in many ways funding all of those other things and funding my lifestyle and a renovation and all the things that we like to do to make yourself as comfortable and happy as possible.
DM: But there was a time that I was really trying to convince myself that if I just had better organizational skills and… As you say, put my life into a bento box, then maybe, maybe I could do it all. And then I knew, I had actually… I had asked a woman who was then at the time when I was interviewing her, she was the General Manager of Puma, and she had stopped doing that and had started a retail bookstore in Boston. And I said, “Well, how did you do it? How did you just make this decision?” And she said “I had to let go of the trapeze.” And then I had this vision of myself, not just holding on, but with like an arm in a… Both arms crooked through both legs, even my hair, so holding on to dear life.
BB: A foot tossed over.
DM: And so, just dropping off would be that much more difficult, but I did have to start to sort of unfurl. And as I said, it was terrifying because I did have a lot of power, I was making a lot of money, I loved what I was doing on a lot of levels, but I also knew that for the past 35 years, I had been living primarily with a lead gene of safety and security, and it was really time to decide if I could rely on myself without all that. And that was scary.
BB: What was the thing that you just couldn’t say no to, by saying yes to that job? Was there one creative endeavor, one project, one vision of your life that you just said, “I can’t say no to this. I’m going to have to let go of the trapeze?”
DM: It was potential.
BB: Say more.
DM: Well, it’s the first time that anybody’s asked me that, so I have to sort of get my thoughts in order about this, but one thing that I was asking myself, and I still do, as time marches on is “If not now, when?” And one thing that I had come to realize, and now I do try to imbue this in my students is, you never… Or at least I, let’s say I; I’ve never felt ready. I’ve always felt that I needed to be prettier, smarter, skinnier, healthier, more connected, wealthier, whatever it is, because I just didn’t feel enough enough, which is why I’ve always loved your first TED talk. I mean, that’s something I teach, that every single one of my students see that in the first semester I teach them. What is it to feel like you’re enough?
DM: And because all of these other things were filling me up and making me feel for a time enough. But we know it’s just a hedonic treadmill and it’s a leaky bucket, and those things metabolize really quickly, and I just kept metabolizing, metabolizing, metabolizing to a point where I was a junkie, I was a success junkie, and had to realize that if I didn’t begin to start thinking about the things that I’d always told myself I wanted to do if, if, if; that if I didn’t do it, I was never, ever going to do it. And it was really my brother, I think, finally saying, “You’re never leaving.” That made me say, “You know what, I am going to show you little brother.” And I did it.
BB: Thinking about the book Why Design Matters, which again, I only have guttural sounds to describe how I feel about it, which are like, ugh, uh. What do you think…? You said it just now, but I want to push you for something more, what do you think is the relationship between our beliefs about readiness and our worth?
DM: There’s the holy grail question.
BB: Especially when it comes to creativity. It can apply to everything. But like, what is that relationship?
DM: Well, this really goes back to something that I learned from Danny Shapiro. When I interviewed her on the podcast, afterward, she came into my office at SVA, the School of Visual Arts and saw a stack of confidence books on my desk, like The Confidence Code and…
BB: Yeah, oh yeah, I got the stack.
DM: Yeah, exactly. And she said that… She looked at the books and she kind of scoffed. And at the time, I was like, confidence is the holy grail, that’s what I’m looking for. As soon as I have that I am set. And she said, “I think that confidence is really overrated.” I was like… Looked at her like she was an alien. “What do you mean confidence is overrated?” And she said, “I think courage is more important than confidence because once you take the step into that unknown, that’s what propels you forward. And that’s more important.” And I nodded, and it really profoundly impacted me, and I’ve been talking about and repeating that ever since, but one of the things that it got me thinking about was, well, what is confidence then? What is confidence?
DM: And I think that ultimately what I’ve decided is that confidence is the successful repetition of any endeavor, that when you can look at the possible future doing this thing and the odds are in your favor that you’ll be able to successfully pull it off, you have confidence to try it, or to do it again. And we all… For those of us that can drive, we have car confidence, we don’t get into a car now and think, “Oh, I hope I don’t crash it on the way to wherever I’m going,” whereas when we started driving, we were really worried, who wasn’t nervous in…
BB: Every time.
DM: The driving test, right? Not anymore. And so, waiting for the confidence is like Waiting for Godot, you have to actually step in to the act of doing it, and then over time, doing it over and over again, knowing that like babies trying anything for the first time, you’re going to fall or dribble or poo, whatever it is, you’re going to do these things until you know how to do them well on your own, and then you develop confidence over time. But even in the development of confidence… And so, you know, I know I’ve done this successfully before. I’ve run a graduate program, I’ve successfully graduated students in the past; there’s still always that nervousness like, “Will I be able to do it again? Will I be able to do it again?” But I can rely on the fact that I have successfully done it before and try to get myself into that mindset to then do it again but hopefully do it better. It actually is reminding me of a story that I think you’re going to love.
BB: Oh God, I’m ready. I’m excited.
DM: So, I’m a huge Barbra Streisand fan, huge. I worship the woman. Ever since I was a little girl standing in front of my grandmother’s full-length mirror with a hairbrush in my hand, singing along to “Stoney End” which is my favorite of all of her songs, which Laura Nyro wrote by the way. That’s just an important thing to know. In any case, Barbra Streisand wasn’t touring for most of her career, she performed very young at Central Park live, she forgot some lyrics to some songs and then didn’t want to perform again. She was too nervous. There was a great article in The New Yorker a couple of years ago about the fact that she has stage fright, and her manager was saying that her greatest talent actually isn’t her acting or singing or any of the amazing things she’s done and won every award for, it’s that she can do all of these things with debilitating stage fright.
DM: So, when she started touring again, when she came around New York the first time, I went with a friend and saw, and then he came back to my house, and like good little gay people we watched a full night of Barbra movies. And then when she came around again, a couple of years ago, she actually performed at the Barclays Center, the tickets were very expensive, no one wanted to go with me. Even when I offered to buy tickets, people just didn’t want to go for whatever reason, their loss. I went by myself. I wore my Barbra Streisand T-shirt, went to the Barclays Center by myself…
BB: I can see you.
DM: Sat in the audience singing along. And when you’re by yourself you tend to observe more.
BB: Oh yeah, yeah.
DM: And so there I am in the amphitheater, and for whatever reason I look up and nestled high amongst all the lights and the wires, Brené, is a teleprompter with all the words to all her songs. Now, I could have gotten up on that stage and sing “Stoney End,” and “The Way We Were,” and “People” without a teleprompter. But the fact that she had that there, just my heart burst. If Barbra Streisand needs the teleprompter to remember the words to all her songs because she’s still afraid on some level that she’s going to forget the lyrics, then there’s hope for every single one of us.
BB: Oh my God.
DM: I knew, I knew you would love that story. I knew you would love that story. There’s hope for everyone, we just have to figure out a way to hack around the fear.
BB: There’s no shame in the teleprompter.
DM: None, none. And so in terms of answering your question, when you have enough to feel worthy, when you fucking decide… I don’t know if I’m allowed to curse, when you freaking decide, that’s all it is. You just have to decide it’s important enough to do it, and know that whenever there’s any uncertainty, any uncertainty, your reptilian brain will make your heart flutter and your blood burn a little bit and you just have to decide that it’s more important to do it than to not because… And this is something I loved your episode with Dan Pink. One of the few emotions we can’t metabolize is regret.
BB: Oh yeah.
DM: We can metabolize our grief, we can metabolize sadness, we metabolize success, we don’t metabolize regret because there’s no closure, there’s always that, “I wonder if, what if, could have, would have, should have,” and we can’t metabolize it, so that wheel just keeps spinning over and over and over again with our various scenarios that we play out for all time. And so do we want to live with that regret, or do we want to live with the idea that even if we do fail, we’ll likely metabolize the failure and move on.
BB: God, that’s so beautiful. It’s another… You’re so good. You have such an elegant way of addressing mythology, I don’t know if you know that, and I don’t know if it’s an intention or not, but just the first myth that you’re shame free. No, both of us would say “We have this much more hope than we do shame.” The mythology that I think people may make up that you or me or other people they see are just always ready, I’m never ready. I’m never ready, I’m never ready. I just go. I prepare. But in terms of emotional readiness, I’m never. I’m always fearful, and I always have my version of the teleprompter. I’ll tell you one of my funny versions is that when I do big speaking events, I’m really comfortable on stage. I’m a teacher at heart, I love it, but I always keep my purse very close to the stage in case I need to grab it and go.
BB: Yeah, that’s like a Texas upbringing. Always have your purse in an exit ramp. I always have my purse really close by in case I’m like, “Fuck it, I’m out of here.”
DM: You know Aretha Franklin did that too? She brought her purse on stage with her?
DM: Yeah, she…
BB: You’re kidding.
DM: I’m not. So first of all, Aretha, God bless her. Rest in power. She used to demand that her fee was paid in cash, and she would take that cash and she would put it in her purse, and she’d bring it with her on stage, and it was on stage with her the whole time, and then she’d take it and walk off.
BB: I’m going to start asking for cash if you’re listening, you’re upset about that, you’ll know where it started. Okay, walk me through the birth of your podcast, because you were podcasting before I even ever heard the word, tell me about the birth of the podcast and the story that leads to this incredible book.
DM: Well, the year is 2004, and I had at that point, eight or nine years of corporate success, and as I said, I had become really addicted to it and gave everything else up, I stopped writing, I stopped… Well, I stopped writing bad poetry, that was probably a good thing, but I stopped writing in my journal, I stopped… I was doing a lot of craft work, I was doing a lot of needle work, I was drawing a lot, painting for years and years and years. I gave it all up. I gave everything up, I put my guitar into the bed, and it was literally work 24/7. I got so much, that feedback loop of finally doing something well. I was in my 40s, it had been a long time coming, and I just wanted it to keep on keeping on, and so I gave everything else up. And I started to feel about eight or nine years in, that I was losing my creative spirit and that maybe my creative soul was gone. And I had been writing… I had started writing for a blog, which was a very new thing back in 2003 when I started, and an article that I wrote got a lot of traction.
DM: It was an article that I wrote, actually the article that got a lot of traction was in 2004, and it was about the use of purple that we were beginning to see in the election maps when George Bush was first elected President. And I wrote about it and it got a lot of traction, and I got a cold call from a fledgling internet radio network called Voice America, not Voice of America, which is different, it was Voice America. And they wanted me to do a show on their business network about branding. I thought they were offering me a job and I was like, “Wow, this is like a whole new pinnacle,” and they weren’t. They were offering me an opportunity to pay them to produce a radio show for me, so it was the ultimate vanity project. But I thought this is something really new and different and exciting, and when I was in college, I worked in the student newspaper, but I always thought the people working on the radio station were the coolest people on campus.
BB: They were the coolest people for sure.
DM: Was envisioning myself this sort of cool Samantha Ronson DJ type. And so I said…
BB: I can see it.
DM: Right, right? And so I agreed, I had to pay them to produce 13 episodes, and the one pushback I gave them was that I didn’t want it to be on branding, I really wanted it to be on design and Design Matters was born February 4th, 2005. It was an internet radio show. One of the founders of Speak Up, Bryony Gomez-Palacio was frustrated that because the show was a live internet radio show with call-ins, with commercials that you could only listen to it when it was live or the one time it was being replayed in the wee hours of the morning, and suggested that I take the digital file and upload it to iTunes, like I was an indie musician. And this way it would be more convenient for her to listen to it, and so I did.
DM: And so I did that and I think I started in February. So I think by April I had started to upload the files and inadvertently became one of the first podcasts because very shortly thereafter there was a podcast section, I remember the first chart, and I think I was number 85 out of 100, but there were only like 105 podcasts, so being 85 wasn’t really any great shakes, but I still have the screenshot of that chart by the way, and just kept doing it. Just kept doing it. It was terrible. The sound was horrendous. I was doing it on a landline, my guests were sitting across from me on a landline, and so all the feedback that you hear when everybody’s piling on to talk to grandma from the same house with different extensions, that was my podcast.
DM: And I did it for 100 episodes that way, and then the late great builder until another founder of another wonderful blog that started shortly after Speak Up called Design Observer. He came to me and asked me if I would bring the show to Design Observer with the proviso that I improve the sound quality. And I’m like, “Bill, this is not my purview.” And he found me a producer, Curtis Fox, who’s been my long-term producer ever since 2009, he came on and started working with me, we’ve been partners ever since. And then two years ago, I took the show to the TED Audio Collective. So I still own all the IP, it’s still a very independent show, but now they are helping me with trying to bring it to more people around the world. So, the book. The book.
DM: The book was something that my agent really concocted. I had worked on a book with three of my friends about a great, great art director, one of the great art directors of the 20th century, a woman named Cipe Pineles, who has never really gotten the attention she deserved for doing the breakthrough work she did. She worked at Seventeen, she worked at Charm magazine, she was just a real maverick in the world of art direction and magazine design. And Wendy MacNaughton and Sarah Rich found a journal that she had written and drawn at a vintage bookseller, and they bought it.
BB: No way.
DM: And it was full of recipes that she had created, and they were all beautifully hand drawn and handwritten. And Wendy’s agent is Charlotte Sheedy, the legendary Charlotte Sheedy. Charlotte saw this book, Wendy approached me and Maria Popova, and we all chipped in to buy the journal. And then Charlotte got us this book deal and we wrote this book… We all put this book together. Sarah Rich really did the lion share of the work, but we all contributed to a book called Leave Me Alone With the Recipes, and it’s the life and recipes of Cipe Pineles.
DM: Charlotte then approached me and said, “You know, you’ve been doing this podcast for a long time, you’ve won a bunch of awards now, you’ve gone to the White House, Michelle Obama likes it. Harrison Ford seems to like the show. Why not make a book out of it?” And I thought, well, it’s already out there. It’s no new news. Everybody can listen to the podcast. She’s like, “Well, you can do some more, you can have essays, you can edit it, you can make it really special.” And I was like, “Well, okay, if you think it would be a good book,” and she did, and she got me this wonderful book deal with HarperCollins. And then I had a year deadline, and then Brené I fell in love. You know this part.
BB: I know this part. For everyone listening this will be my favorite part of the story. Do you want to say that you fell in love?
DM: I fell in love with Roxane Gay, and suddenly it was like, book deal, schnook deal.
DM: I don’t want to write a book, I just want to be in love. And so I put off the book, and I put off the book and I put it off and then it was like my deadline was approaching, and I told my editor I needed more time, and she was like, “What? You couldn’t have told me this a few months ago? That’s three days before your deadline.” And I’m not joking.
BB: I know. I unfortunately have made that call. It’s a tough call.
DM: Yeah, and you know, all the while Roxane is saying “Oh they’ll be okay with it, they’ll be okay with it.” And I’m like, “You know why she said that, because she’s Roxane Gay. And they would be okay with it until that moment, I’ve never done this kind of a book before. Yes, I’ve done little books, but not a big book like this. And they weren’t okay, but they did give me another year. And so that is how it happened. What then occurred was COVID, and so rather than do a photo shoot around the country with the various people that I wanted to do include in the book, I ended up having to photo edit the book as well, but that turned into my favorite part.
BB: Oh, God. It’s so beautiful.
DM: I had never photo edited before, and suddenly I was reaching out to some of the world’s greatest photographers to get some of the world’s most beautiful pictures of these guests that I had interviewed over the years. And so that was fun, and it was hard work. I had to look at 400 transcripts, picked out the 100 or so that I felt could be included. The problem with doing a book like this was that the interviews all needed to be shortened, it needed to be significantly edited, and a lot of the conversations… And I think, you know this, when you have really beautiful, deep soulful conversations, it’s hard to say, “Let’s just cut those three paragraphs out, they don’t matter,” they do.
BB: It’s painful.
DM: So I had to go through and really extract standalone pieces that could all live in a book without necessarily having an entire interview. There’s not one interview in this book that’s an entire interview from start to finish that I did with anybody, because then I would have only been able to include seven interviews, so they’re 60, and I think the best possible excerpts from the best possible interviews that I’ve done.
BB: So, I’m curious, I have so many questions. Can I just launch in?
DM: Yes, please.
BB: Okay, just because this is my favorite part. The dedication.
DM: I did dedicate it to Roxane. And I held that back, she didn’t know until she actually saw the book in her hands.
BB: Oh my God, I love that. Yeah, I just love that. I knew before I saw it. Okay, so you divide it into legends, truth tellers, culture makers, trendsetters, visionaries. I’m so curious as a qualitative researcher, did you go in with those categories or did you sit back and look at the finished product and say, “Oh, here’s some organic buckets?”
DM: The latter. For sure. Frankly, almost anyone that’s included in this book could be in any of them.
BB: Yeah, I actually loved these categories.
DM: Oh good, I’m really glad. It was hard for me because I did feel like I needed to… After all the interviews were chosen, after all the quotes were chosen, after all the photographs were chosen, I felt like I needed to lead people through the book, I needed to sort of help them navigate through. I wanted them to be able to pick it up at any place they wanted and have something fun to look at and read, but I also wanted to give them a path, and so I did feel that 60 interviews, one after another after another after another would be just kind of cumbersome. And so, organizing it in this way made me happy, it gave me a way to thread some common denominators. I do think that there’s a common denominator in the photography, despite having 50 photographers’ work in this book. The one common denominator, I think that’s evident in all the photos is soul.
BB: Oh God, they’re so soulful. You look right into the eyes. Yeah.
DM: You really see the soul. Yeah, that’s what I wanted, and most of the photos are very tight crops of a person’s face, so you see all their beauty and all their longing and life and everything. And then I wanted to be able to give people a way to think about the way in which people are producing their work in a way that allows them to see the commonalities in the way that it’s organized. But it was really difficult. That part was hard. There were lot of hard things about this, but to quote the great Glennon, “We can do hard things.”
BB: We can do hard things. Yeah, I have to have two. So we bought several because I have to have one by bed, the interviews are so great to read before I go to sleep.
DM: Oh, good.
BB: I feel so inspired. And then I have to have one on my coffee table because it’s so beautiful, but one thing that I’ve noticed is that people have a tendency to pick it up and go, “This person’s head is as big as my actual head.” It’s a big book. The photos are like, “That’s Seth staring right back at me. That’s Isaac Mizrahi as big as my head.” I love that.
DM: Yep. I wanted the book to have what I’ve titled Plunk Value, it’s an expensive book, I wanted it to feel heavy and needy and delicious.
BB: Yeah, it feels like, “Listen, y’all.” It’s like, you know, when you’re in a nice car and it closes a certain way, the door.
DM: Yeah, yeah. Yep. And there’s lots of little Easter eggs. As a designer, I really wanted there to be fun things for people to find, the various scribbles. I ended up doing this, a little tiny scribble… Obviously, there’s a big scribble on the cover, but there’s little scribbles all throughout. All of those are different. At the end of every interview, there’s a scribble, and every single one of those is different, it was really funny. I worked with an incredible designer who helped me put the book together, Alex Kalman, and he has such a wit and such a beautiful, optimistic way of looking at the world. He was up for anything. He was just like, “Yeah, let’s do 150 scribbles and pick the best ones. Let’s do this, let’s do that.” And he actually did the… Under the jacket is the case, the case of the book, and if you look under the jacket, you’ll see he took the scribble and then put words into both the front and the back side of the book, and he felt that those were the themes that were in the book. But when I looked at them, I decided those are the themes of life; shame, jealousy, hope, loneliness, longing. I can’t remember them all by heart, but…
BB: Resilience, loneliness, fear.
DM: Joy. I know Joy is there. And that’s all part of it.
BB: Okay, I’ve hard questions for you. Are you ready?
DM: I’m ready. I’m ready.
BB: Impossible question number one. If you had to distill what you’ve learned, not all your podcasts, but the ones featured in this book, what is the soul of designing a creative life?
DM: Embracing messiness.
BB: Okay, this is a hard question, but you know what, I don’t even want to know the answer to this question from anyone in the world but you.
DM: Oh God. Pressure is on.
BB: It’s a two-part question. I’m going to put both out so you can untangle and ask. Tell me about the politics of curation, and is curation art or design?
DM: This is a great question, especially given the times we’re living in. Is curation art or design? I mean, it’s going to sound a bit of a cop-out, but it is really both, it’s not just art or a design, it’s also a science and a practice, because if there’s high level curation, there’s museum curation, where you’re choosing what people get to look at and admire and aspire to and fawn over and try to understand and deconstruct. There’s that whole other level of curation, and then there’s curation of living every single day with intention, with deciding what you want to wear and what you want to eat, and who you want to be with, and who you want to love and how you want to love? All of those things are decisions. Now, curators would scoff at that, the real professional curators would scoff at that and say, “Please don’t associate the quotidian daily behaviors with this high art of deciding what belongs in a museum.” And I don’t want to say that they’re the same. They’re very different.
DM: But the act of intention, the act of choice, is the same, we are deciding every day who we want to be and who we are, and so in that case, everything is design and everything is curation, in the same way the curators are upset with saying that, “so we’re designers, so does mean everybody’s a designer?” People ask me about how do you define design? And I say design is about intention. Deliberate intention. Well, then the next question from skeptics is “Well, is everybody a designer then?” Everybody has the ability to do this, the level of professionality one brings to it might be different depending on your mode of living and also your practitioner, the type of practitioner you want to be, but we are designing our lives every moment that we’re living them, if we are making choices about how we want to live. And I think that that’s terrifying and hopeful at the same time.
BB: Yeah, it is both really, I don’t like the responsibility, but I really like the ability.
DM: But when we get to something that’s been happening of late is, well, what is censorship then in regards to curation? Well, when we’re deciding what we do or don’t want to listen to or to participate in, or to have in our lives, that’s not censorship, that’s curation; we’re deciding we don’t want to do this, and we’re not telling anybody that they don’t have the right to do it, we’re just saying, “We don’t want that in our lives.” And I think that’s a very, very important distinction.
DM: You don’t have to love everything that’s being made because that’s free speech, you can respect the fact that people are allowed to say it, but you don’t have to invite it into your life.
BB: Are the words curation and discernment synonymous?
DM: No, I don’t think so.
BB: Tell me what you think the difference is. I’m curious. I’ve got so many hard questions for you.
DM: Yeah. No, this is a good one. Well, first of all, how would you define discernment?
BB: I guess for me in my life, it’s something I have to work on a lot, so I would say discernment for me is about intention, thoughtfulness, big picture. It’s more about the practice of intention. For example, I guess what I’m saying is like, what do I say yes to and what do I say no to? And I have a tendency to say yes to everything out of fear of things going away, opportunities going away.
BB: And so one of the things I work on is discernment, how do I discern. Even when I say the serenity prayer is part of my sobriety, I say, “Grant me the strength to accept the things I can’t change, the courage to change the things I can, and the wisdom to discern the difference.”
BB: So I think it’s about mindful thoughtfulness or something, I don’t know.
DM: And this is by no means an academic response, this is just my take on the difference. I see discernment being something I do externally, I decide this versus this, this versus this, from external input, things that are coming towards me, and I see curation as a way in which I try to move through the world.
BB: Oh my God, that’s so helpful. Can you say it again? Can you make the distinction?
DM: I see discernment as the decision-making from the external inputs that are coming my way, and I see curation, my form of curation, as the way in which I move through the world, the decisions that I make as I move through the world, and those certainly do intersect, obviously, the discernment and the curation do thread together, but I do think that they come from very different neural pathways in my brain.
BB: Yeah. Oh my God, that was so helpful. Okay, I’m going to say something that I believe in my bones, but I don’t know if it’s true or not, because I love design, I care a lot about design, and I care a lot about excellence in design and thoughtfulness in design. I firmly believe that design is a function of empathy. Do you think that’s true?
DM: Yes, I do.
DM: So, there’s a number of different ways that we can think about design, one being a sort of mindfulness practice in the way one lives. And then there’s the professional aspects of design, and the difference between design and art is that with design, you are generally working for a client, that has very specific criteria for success. You are solving a problem or causing a problem for a client with very specific goals in mind and you’re working toward the fulfillment of those goals. Chances are, it is about a return on an investment or a communication of a specific message that creates consensus in the minds and hearts of the people that are listening to it or hearing it. Or it’s about creating a specific kind of shelf presence or a style that people will enjoy and participate in. The common denominator in all of that is reaching people with that message, with that product, with that thing, with that belief, creating that consensus. The only way to do that is to be able to reach people in their hearts, and that requires empathy, that requires a level of understanding of human behavior, of behavioral psychology, that necessitates a way into understanding what is fundamentally important to someone.
BB: God, this is so… When I pick up something, an appliance or I look at something, an ad, or I interact with design, a chair, I can feel sometimes like, of course whoever did it doesn’t know me from anybody, but like, that person cares about me. That person sees me, knows me, that person… Like good design feels to me like… I don’t know, there is such a human connection in good design, and I can’t articulate it, it makes me sound like I’m nuts, but I felt it in this book.
DM: No, no, not at all. That’s designers doing their job, frankly. The thing is, we’re living in a world that’s so oversaturated with products and things that humans are less interested now in products with a different form or a different flavor, or a different shape or a different color, they’re much more interested and impacted by brands that are making a difference in their lives that are helping them feel better about who they are, or in this experience. And these things are also fleeting, getting back to Dan Pink, who is just so brilliant at all of this, he’s saying, “Your idea of happiness, if it’s a larger flat screen TV, you’re playing a fool’s game because humans metabolize their purchases very quickly, and the problem with these things is that if we do use them to fill up an otherwise very mushy center, then you’re going to need to keep filling it up.”
DM: But the most important tenant of design now is really understanding human behavior and the understanding of behavioral psychology as it relates to how we feel about ourselves, how we feel about others, how we share or don’t share, what we covet, what we don’t, everything we buy, everything we purchase, everything we engage with telegraph something about ourselves, even if we don’t want it to. Years and years and years ago, I remember my dad saying, “I’ve decided I am no longer wearing T-shirts with logos on them, no more Polo, no more Lacoste.” Okay, rather than throw them all away, he decided he was going to put a flag pin over the logos, and I was like, “Dad, that’s a logo. You’re still signifying your affiliations with the flag pin, might be different than the Lacoste or the Polo logos, but it’s still signifying the tribe you belong to.” And that’s what brands do now, they telegraph our affiliations, they signal our beliefs, they allow us to be seen and understood by others, and marketers look to create as much consensus as possible around the brands that they make to have the biggest possible audience all believe the same thing.
BB: Yeah, there’s such an unexpected intersection between your work and my work, and at the core it’s about people.
DM: But the really exciting thing, can I just say one really exciting thing about branding?
DM: That really gives me so much hope. For most of our existence on this planet, let’s say as modern humans, we have been mark making. The caves of Lascaux show that we were making marks thousands and thousands and thousands of years ago. Ten thousand years ago we started to create symbols to signify our beliefs in a higher power. We did this all over the planet, which is really interesting, all at the same time suddenly we started mark making symbols to signify a relationship that we had with a God, despite that God being different. And we used family crests, we use flags, all of these human designs to signify where we belonged, who we belong to and with.
BB: Yes, belonging.
DM: It’s only in the last 200 or so years that the corporation appropriated this behavior to create the ultimate set of signifiers, which is a label, this label became the way in which we started to communicate various attributes of the product, and that again, created consensus, and that’s sort of the way it’s been for about 250 or so years. But in the last 10 years, we the people have started to pull that back and have started to use the very tenants of branding to create the Nike Swoosh and the Apple logo and so forth, to create movements. So, the very tenants that we’ve used first to create religious symbols and then to create flags and crests and then products, we’re now using those same behaviors to signify beliefs in the way we should be living.
DM: That’s what’s so exciting about things like Black Lives Matter and Me Too. Tarana Burke has been doing this for a long time, and whether or not she realized it, she is a brand master. It’s a brand, it’s much more than a brand, it’s a movement, but it’s been able to create a ground swell, which then results in a change in behavior, which then results in a change in the way we live in the world, and that’s the most exciting thing. I think, really on its very best day branding can and should be a profound manifestation of the human spirit, because people like Alicia Garza, people like Tarana Burke are showing what’s possible when you create consensus in this really important, significant way. I’ll get off my soapbox now.
BB: That my friends is a master class right here. Wow, that was so good. Wow, that was amazing.
DM: I’ve been doing this work for a really long time, and I’ve been criticized over the years for being a she devil because of my involvement in branding, thankfully that’s passed, but I do believe that these behaviors are just part of our human DNA.
BB: DNA. Yeah.
DM: And it’s not going away, and so let’s use them for the purposes of making the world better and not just buying more stuff.
BB: Yeah. If you really step back, branding is a function of being a social species.
DM: Yes. Yes.
DM: My work here is done.
BB: Okay, I have two more book questions and then rapid fire, because you know I love you on the rapid fire.
BB: Okay, so you said if you look at the folks that are featured in the book, and you had to distill the heart of designing a creative life, you said embracing the mess, right?
DM: Life is messy. Leadership is messy. Everything is messy.
BB: Oh my God, you’re singing to the converted. What, doing the same kind of qualitative analysis of the folks featured in the book, what would you say in a very singular way, which is probably unfair, is the greatest barrier to designing a creative life?
DM: I would say that the biggest barrier is oneself because…
BB: What about oneself specifically?
DM: The notion that you have to be enough of something to deserve a place in the world to say it or to express it. The one common denominator that I think everybody in the book shares is the belief that their voice is worth hearing, it doesn’t mean that they don’t have self-loathing or insecurity or a fear that their best work is behind them, or that they’re not going to wake up tomorrow and wonder if they can do it again. They all have those things, but for whatever reason, whether it be good parenting or bad parenting or perseverance or any number of things, they all feel that their voice is worth sharing, and that’s such an incredible place of both generosity and creativity, that makes me feel like the luckiest person alive to be able to talk to people about those specific things. Yes, design matters, and that’s where the show began, but ultimately, I’m so endlessly fascinated by how people design who they become, as I’ve struggled to do that and still I’m trying to make it happen. I am just in awe of the ability that creative people have to create.
BB: Yeah. Okay, last question about the book, then we’re going to go rapid fire. What surprised you the most?
DM: Oh, this is something I’m really excited about. I think I’m a good photo editor. I really, really feel like I knocked that one out of the park. I never photo edited before, and I ended up having to what became the sort of de facto photo editor after I couldn’t do a photo shoot because of COVID and I loved it. I loved it. So that’s the thing that surprised me most, and that’s the thing I enjoy the most.
BB: It’s just beautiful, the photos, it’s just… You get excited to see what the next one’s going to look like because they are… Like you said, so soulful. So, congratulations.
DM: Thank you, thank you. It was funny because there were a couple of people that almost didn’t make it into the book because of the photos. I had a photo from Elizabeth Alexander, who I was insistent be in the book, and her photo was a beautiful photo, but it was her professional photo from The Mellon Foundation, and I wanted something that just showed her poetry, her poetic spirit and not the professional, and I couldn’t… I was dealing with her people, and so this is what they were giving me, and I didn’t want to push because I also didn’t want to be in a position where they were like, “Forget it, we don’t want to be part of the book.” And then I texted Maria Popova, my dear, dear friend, and they’re friends, she and Elizabeth; and I’m like, “I found this photo, I really want to use it. Please can you text Elizabeth to see if she’ll check her email and give me permission to use it?” And so that sort of the machinations that made that happen at the last second. And then with Oliver Jeffers, he gave me photos that were just too small, the book is 10×10, I needed huge photos. And I said, “Oliver, I can’t use these, they’re too small.” He ended up doing a photo shoot the day that my files were due, and this was the third past deadline.
BB: And it was a great picture.
DM: Yeah, his slippers make the shot, I think his slippers.
DM: That was the most surprising and fun part for me.
BB: I love it. Your joy in it comes across.
DM: Yeah, I would love to do another visual book in 400 years, but yes.
BB: I’m ready for it. Okay, rapid fire. Fill in the blank for me. Creativity is?
BB: Fill in the blank for me. Vulnerability is?
BB: What is one piece of leadership advice that you’ve received that’s so shitty, you need to warn us, or so great, you need to tell us?
DM: Pick one.
BB: Say more.
DM: I was told to pick one. When I was first, first, first, first, first a baby designer, and I wanted to be… I also wanted to write, and I also wanted to paint, and I also wanted to do all these other things. I had an HR person at Condé Nast say “Pick one thing and stick with it.” I didn’t get the job, clearly, and I think it’s the worst advice that anybody’s ever given me. Now, I do believe very, very strongly that mastery takes time. And do feel like Malcolm’s probably right about the… At least 10,000 hours, 10,000 hours if you’re like a genius.
DM: But I do feel that you can have different pockets of time dedicated to different things, it might take you longer to master them because you are diluting your time in these different ways, but it’s also much more meaningful time because you’re fulfilled by doing these various miscellaneous things that you love, that all do tend to blur into each other, so rather than 10,000 consecutive hours, it might take a little bit longer, but that’s the worst advice I ever got, that you have to pick one thing. I do not believe that.
BB: God, I’d give that 100% because all of my different things that don’t seem connected ended up being so inextricably connected and informing the other things. I agree. It’s so good. Okay, hard question. You ready?
BB: What’s the one kind of leadership lesson that the universe just keeps putting in front of you in different ways because you have to keep learning it and unlearning it and relearning it?
DM: Well, I kind of said it already, but I’m going to say it again because it’s always constant, and that is leadership is messy, and I want everything to be neat and well organized and beautifully designed, and I hate mess, I hate things that… My idea of a good time is reorganizing my sock drawer. And I’m being serious, and Roxane will attest to this. I get enormous pleasure just organizing my linen cabinet. In any case, the fact of the matter is people are messy, leadership is messy, and everyone has needs and wants, and sometimes the very things that one person wants and needs and loves, the very things that other people are outraged by. And so the one thing that I have to learn over and over and over again is not only is leadership messy, but I’m never, ever, ever going to be able to make everybody happy at the same time. Ever.
BB: Amen, sister. Okay, tell us one thing you’re really excited about right now?
DM: Besides talking to you right now?
DM: Oh my God, this has been the most… I mean I’ve been so excited and so nervous, I’m excited about the summer, and going on a boat trip with my wife to Greece. I had lost a very, very, very, very important person to me two years ago before COVID, and she was born in Greece, and her desire was for her ashes to be scattered in Greece, and I promised her I’d do that. And so I’m actually going to be able to do that in August, and I am counting down the minutes, although I don’t want to count too fast because it’s good to just live them one at a time, but I am looking forward to that.
BB: Yeah, and the anticipation is so fun too. I can’t wait. You’ve got to give us a picture of you and Roxane in Greece, I’ll be watching your Instagram post.
BB: Okay, we asked for five songs. Here’s what you gave, five songs you can’t live without: Landslide” by Stevie Nicks, “Weird Fishes.” Is it just “Weird Fishes” by Radiohead?
BB: “Two Grey Rooms” by Joni Mitchell. Oh God, you’re so good. “LOVE” by Kendrick Lamar. “Holiday,” by Madonna. One sentence. What does this mix tape say about you?
DM: I’ve got some good names there.
BB: You got some range.
DM: I forgot that I had given you those songs, but yes. Oh my God, I love those songs so much. Tavi Gevinson just did an incredible interview with Stevie Nicks in The New Yorker, and God was I jealous, it’s so good. I love Stevie.
BB: This has been such a pleasure. When we get to talk, I look forward to it for like just… I think about it all the time all day, “What am I going to ask? What do I need to know? What do I want to know? How can I ask her about design, but really the answer is going to help me in my therapy?”
DM: Oh my God, thank you. Brené, this is an honor and a pleasure, and I feel so grateful even just to be in your orbit. Thank you, thank you. Thank you.
BB: Feel the same way. Thank You.
BB: How easy is it to fall in love with Debbie Millman? I mean, come on, it’s just… That whole piece about branding as a social species and what we can do around organizing and activism, and how we use markings from the beginning of time all over the world, but to convey the same thing, which was our first relationship with, I don’t know, the human spirit or God. She’s magic. She’s a magic person to me. You can find Debbie’s new book Design Matters: Conversations with the World’s Most Creative People, wherever you buy books. We’ll post a link to it on the Dare to Lead episode page. Debbie is online at debbiemillman.com. She’s also on Twitter and Instagram @DebbieMillman. We’ll put all these links on the episode page on brenebrown.com.
BB: I’m glad you’re here. I loved this conversation. I believe to be human is to be creative. I don’t believe in the idea that there are creative people and not creative people, I think we’re all creative, and I think unused creativity is not benign, it metastasizes and turns into grief and hurt and anger, and I think Debbie is just a beacon about what it means to embrace the messy and go before you’re ready and have just a little bit more belief and hope than you do your own shame. That’s just gold. All right, y’all stay awkward, brave and kind, I’ll see you next week.
BB: The Dare to Lead podcast is a Spotify original from Parcast. It’s hosted by me, Brené Brown, produced by Max Cutler, Kristen Acevedo, Carleigh Madden, and Tristan McNeil, and by Weird Lucy Productions. Sound design by Tristan McNeil and Andy Waits, and the music is by The Suffers.
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