Debbie Millman | How to Design a Life [Best of]

Debbie MillmanHow do you design a life of wonder and love, contribution and meaning, joy and expression? At the end of the day, that’s what we all really want. To know we’ve used our time on this big, blue marble in a way that was worthy, that was wise, that was alive. Which is why I was so excited to sit down with an old friend, Debbie Millman, who just happens to be a legendary thinker and doer in the world of design, branding, innovation and life. Named “one of the most creative people in business” by Fast Company, she’s an author, educator, curator and host of the iconic Design Matters podcast, where she’s interviewed hundreds of the most creative people in the world over the past 17 years. 

Debbie is also the author of seven books, and her new book, Why Design Matters: Conversations with the World’s Most Creative People, is a stunning compilation of her own take on everything from design to branding, business, entrepreneurship and life, mixed in with moments from guests that have, in no small part, collectively designed the world we live in.

Debbie co-founded the world’s first graduate program in branding at the School of Visual Arts in New York City, was the President one of the world’s leading branding consultancies, Sterling Brands, where she worked on the brand identity for everyone from Burger King, Hershey’s, Haagen Dazs, Tropicana, Star Wars, Gillette, to the No More movement.

Her writing and illustrations have appeared in The New York Times, The Washington Post, New York Magazine, Print Magazine, and Fast Company. Her artwork is found in private collections, universities and museums around the world. Debbie has a deeply insightful and experienced lens on how we live our lives, how we show up in work and life, and tell the stories that bring it all alive.

You can find Debbie at: Website | Instagram | Episode Transcript

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Episode Transcript:

Debbie Millman (00:00:00) – One of the interesting things that I learned when you’re on this precipice of making a change, I don’t know if it’s human nature or if it’s just my personality style. The only way I was able to envision the future was with less than what I’d had Less power, less identity, less money, less whatever. I never, ever really fantasized about what I might receive in doing this.

Jonathan Fields (00:00:25) – So how do you design a life of wonder and love, of contribution and meaning, joy and expression? Because at the end of the day, that’s all we really want to know. We’ve used our time on this big blue marble in a way that was worthy, that was wise, that was live. Which is why I was so excited to sit down with an old friend, Debbie Millman, who just happens to be a legendary thinker and doer in the world of design and branding, innovation and life, named one of the most creative people in business by Fast Company. She’s an author, educator, curator and host of the iconic Design Matters podcast, where she’s interviewed hundreds of the most creative people in the planet over the last 17 years.

Jonathan Fields (00:01:07) – Debbie is also the author of seven books and her new book, Why Design Matters Conversations with the World’s Most Creative People. It’s this stunning compilation of her own take on everything from design to branding, business, entrepreneurship and life, mixed with moments and insights from guests that have in no small part, collectively designed the world that we live in. Debbie also co-founded the world’s first graduate program in branding at the School of Visual Arts in New York City. She was the president of one of the world’s leading brand consultancy, Sterling Brands, where she worked on the brand identity of everyone from, like Burger King, Hershey’s, Haagen-Dazs, Tropicana, Star Wars, Gillette to the Know More Movement. And her writing and illustrations have appeared in The New York Times, The Washington Post, New York Magazine, Print Fast Company. Her artwork is found in private collections, universities and museums around the world. Debbie just has this deeply insightful, real, honest and experienced lens on how we live our lives, how we show up in work and life, how we give to what we get from, and how we tell the stories that bring it all alive.

Jonathan Fields (00:02:17) – So excited to share this conversation with you. I’m Jonathan Fields and this is Good Life Project. So you and I have been rolling together for years now as we have this conversation at the beginning of 2022. We’re actually celebrating our ten year anniversary on Good Life Project. I think your design matters, what, 17 years at this very fourth?

Debbie Millman (00:02:45) – It’ll be 17.

Jonathan Fields (00:02:46) – Years. Right. And I think the first conversation that we had on your podcast, I think was actually the ten year anniversary of it was the 10th year of your show. So.

Debbie Millman (00:02:56) – Oh, yeah, that makes sense. Absolutely.

Jonathan Fields (00:02:59) – Yeah. Timing is about right. I’ve been amazed at the evolution of this space really just over the last few years. And you know, it’s funny because I think of myself often as we’ve been in this for a really long time. And then I look at the time that you’ve had in the space and I’m like, Not really.

Debbie Millman (00:03:18) – Well, I mean, ten years is still ten years.

Jonathan Fields (00:03:21) – Yeah. I mean, I want to dive into some of the moments in your podcast, some of the learnings and certainly some of the things that you’ve drawn out of it and this gorgeous book that you are bringing to the world literally as we speak.

Jonathan Fields (00:03:34) – I want to take a little bit of a step back in time also before we get there. You know, I was reflecting on a conversation that we had, I guess it was last year with Alan Cumming, and he was describing his upbringing, which was kind of brutal. And he started to create worlds and roles and tell stories at a very young age, almost as a mechanism for him to create an alternate reality where he was okay. And he certainly defined what would happen. And I was thinking about it in the context of you. I don’t know. I just popped into my mind. I was like, you know, from our conversations, my knowledge, you have been writing and drawing and creating from a very young age and from the outside looking in, you probably look at the typical kid and just say, Oh, this is a beautiful, creative impulse. I was wondering if for you it was something more similar to what Alan was creating through the world of acting.

Debbie Millman (00:04:25) – It certainly possible. You know what didn’t thwart Alan’s creativity is, I think what has allowed him to be this remarkable performer.

Debbie Millman (00:04:38) – And it’s quite exceptional that that didn’t really squash him to a point where he couldn’t make use of his talents. A lot of what I was doing was for self-soothing, but a lot of what I experienced also really kept me from feeling like anything I did mattered. And nobody would want my point of view or want my contribution. And that’s taken a long time to to get over. And I would say that I still suffer from that a little bit, but nowhere near the sort of paralyzing impact that it had on on me probably till my late 30.

Jonathan Fields (00:05:21) – Yeah, which is I mean, it’s hard to conceive of that given that you have been in the world and created work that has literally defined the identity of so much of what we experience as we move through the built world. For context, when you were a kid, you sort of bounced around. Your mom ended up getting remarried and and the person who stepped in as that role was not kind is probably a nice word, putting it to you and led to some just really difficult and challenging years for you, which you shared not too long ago, actually, in a conversation with a mutual friend, Tim Ferriss, I guess for the first time publicly and not necessarily knowing that was about to come out.

Debbie Millman (00:06:05) – Yeah, yeah. That was a that was a surprise in that I had this opportunity to answer a question that he asked me about my childhood and why I was so involved with the Joyful Heart Foundation, which is Mariska Hargitay Foundation to Eradicate Sexual Violence in Our Culture. And there’s a little interview with me on the website because I’m on the board, and I said something like, Being part of this organization makes me feel like my life makes sense. And he was like, What’s up with that? You know, not knowing where it was going to go. And there I am sitting across from my dear friend, and I didn’t want to lie, but I also didn’t want to take that path and open that door. But I felt like I had to I owed it to him. I owed it to me. And so, yeah, then it became it became quite public because, you know, there’s nothing like revealing the deepest part of yourself on one of the world’s most famous. Well, listen to podcasts.

Debbie Millman (00:07:03) – If you’re going to do, it’s like go home or go big or go home.

Jonathan Fields (00:07:07) – Right? It’s just like, okay, so now it’s out there on a level where it can’t ever be taken back. It’s just exactly in the world. I’m curious, in the history of our entire show, we’ve had maybe 1 or 2 times where somebody came back to us. You know, later, a couple of weeks later and said, you know, I was just thinking there was something that I said that was honest and it was true and it was real. But I’m not comfortable that I’m not sure I’m comfortable having that in the world. After that conversation with Tim, was there anything in your mind that was going there, or was it or is it almost like the exact opposite?

Debbie Millman (00:07:41) – Well, I was nervous about sharing that part of me, but the nervousness really came from shame at what people would think if they knew this about me, if they knew that I had been abused as a little girl and how they would maybe judge me or think poorly of me, or that I was damaged goods or any any number of things that, you know, the stories we tell ourselves about ourselves.

Debbie Millman (00:08:06) – But I never thought about asking him to take it out. In fact, the only time that anybody’s ever asked me to take anything out. Of an interview was one time somebody asked me to take something up because they thought they might upset someone with something, with an opinion that they had about about something. And I don’t even remember what it was at all or who it was. I just remember one time having to tell Curtis, my producer, Oh, so-and-so would like you to take that out. She’s afraid it’s going to hurt somebody’s feelings. And then another time when there was something that somebody inadvertently said that was confidential and didn’t want to get in trouble. So those are the only two times nobody’s ever come back and said, Oh, I don’t want to reveal that about myself. So I think that’s a nice thing when people feel comfortable enough to share who they are in a way that doesn’t scare them.

Jonathan Fields (00:08:52) – Yeah, no, it’s it’s amazing because it also speaks to the safety that you create in the space when you’re in conversation with somebody, which I think I, I feel like that is such a rare experience these days, that feeling of psychological safety, I mean, it’s thrown around in the corporate world now is like, you know, like this is so critical and so rarely experienced.

Jonathan Fields (00:09:11) – But even day to day conversations and I would venture to say over the last 2 to 3 years have not made the situation better. But the feeling of being safe as you step into a conversation with somebody, I just think it’s so rare that we get the opportunity to feel that way that when you do, it’s sort of like you just want to just completely immerse yourself in it, right?

Debbie Millman (00:09:33) – Absolutely. And I think that’s why I tend to prepare so much for my interviews. I really want somebody to know that they’re not just anybody showing up that I ask the same questions to or that I ask questions that they’ve heard many, many, many, many times before. So it makes it utterly redundant for them. But that I’ve spent some enough time with their work to have a really original conversation. It’s not just having original questions, but also asking them questions that they enjoy asking, answering because they have to think about what they’re going to say and not just press play.

Jonathan Fields (00:10:13) – And definitely shows. I remember actually it was Roxanne, your wife, interviewing you, and I was listening to that conversation.

Jonathan Fields (00:10:20) – I think it was like a guest canceled last minute or something, like so she she tagged in and decided to interview you. And she was describing your interview process to an audience of people. And I was like, yes, two things. One, there’s at least 50 pages or something like that. And it’s probably not the best time to try and have a conversation with Debbie when she’s deep into the research project because you’re just completely immersed in the whole experience.

Debbie Millman (00:10:42) – Absolutely. Absolutely. I get very, very committed to what I’m doing.

Jonathan Fields (00:10:49) – Which is just a sign of the genius that makes it so extraordinary. Oh, I.

Debbie Millman (00:10:53) – Don’t know about that, Jonathan. I would love to think that on my best day, but I actually think it comes from profound insecurity in that I might miss something, forget something, don’t know something that I’m embarrassed about not realizing. I mean, I think it’s the opposite. But either way, I’ll take it. Okay.

Jonathan Fields (00:11:10) – But. But can we dive into that, actually, Because it’s real for sure.

Jonathan Fields (00:11:14) – What do you think? There’s a relationship between genius and profound insecurity.

Debbie Millman (00:11:20) – No, actually, I don’t. Really, I don’t. And this goes back to what I was saying about Alan. You know, for somebody to feel. Really? Deep down like the foundation of of this psychological point of view, that their work is worthy of putting out there, that they are talented enough, smart enough. Creative enough to do what they’re doing with their whole hearts and their all their ambition and their single minded focus. I do think that the foundation of that experience needs to be a sense that what you say and think and do and make matters. And drive might come from insecurity for some people or the need for adoration, but I don’t think that’s genius. I don’t think that’s genius. I think real genius requires that you believe enough in your own ideas, your own curiosity, perhaps, that you’re willing to commit to that at all costs.

Jonathan Fields (00:12:32) – Yeah, I mean, that’s an interesting distinction, actually, because it’s almost like a high level of insecurity.

Jonathan Fields (00:12:38) – Even if you’re creating at a high level and innovating a high level. You probably actually would never share it, right? Because you’d be questioning whether it’s worthy of other people’s gaze or engagement or their time or their investment. So it’s almost like, yeah, that’s really interesting. Would you distinguish between insecurity and discontent?

Debbie Millman (00:12:57) – Well, I think insecurity prevents you from doing certain things or experiencing things fully. I think discontent, if it’s about your own work and not just being a drain to your friends or family, then I think it’s about wanting to be the best at what it is you’re doing and give it your all. And if you’re discontent with your output, you’re constantly wanting to make it better. It’s like an athlete wanting a better time and you know, the 400 meter race. So I think you can be discontent with the results of something that you’re doing that has nothing to do with insecurity. It’s the expectation that you could do better or should do better, I think.

Jonathan Fields (00:13:40) – Yeah, no, that actually makes a lot of sense.

Jonathan Fields (00:13:41) – I don’t know if I know anybody who is sort of has a make or mindset or drive or impulse where if I ask them, Are you largely or even partially content with what you put out into the world where they would honestly say, yes, I think that I could probably like not even count on one hand, count on 1 or 2 fingers. The people who I would ask that question to and would say yes, and they’re probably much later in their careers also, and they sort of have a different answer.

Debbie Millman (00:14:11) – I think that makes a difference when you get to a certain level of excellence. However, I can tell you that generally speaking, in the moment that I’ve put something out into the world, I generally feel okay about it. It’s only later, looking back where I then think, Oh my God, how could I possibly introduce that to the world? Like, how is it possible that I didn’t see how bad that was back when I was doing it? At the time I was doing it, I actually thought it was good.

Debbie Millman (00:14:40) – And that’s terrifying because then it makes you wonder what you’re not seeing about what you’re doing today.

Jonathan Fields (00:14:44) – Well, yeah, but but at the same time, terrifying on one hand. But like, how amazing that it’s sort of like the opportunity for growth never ends, you know, it’s sort of like you’re dancing on that edge on the one hand. Yeah. Wow. What am I blind to, like here, here and here? And how cool is it that ten years from now I will have grown, like, an astonishing amount? I mean, it’s kind of cool.

Debbie Millman (00:15:06) – Yeah. Either that or the patina of the newness of it wears off and you’re left with what it actually is.

Jonathan Fields (00:15:11) – Well, that too. There’s that risk as well. Yeah. Hindsight is a beautiful thing, isn’t it? Yeah. So you end up in the early days, really taking the impulse to create in kind of a very meandering way, finding your way into the world of design. You have a love affair with New York City from the very earliest days.

Jonathan Fields (00:15:34) – You returned to New York City after time at Suny Albany, spending a bit of time learning newspaper layout. When you’re up there and in no small part, it sounds like, you know, when you’re thinking to yourself, well, what am I going to step into? Like, what is this like the career I want to start to build? Art and writing were definitely up there, but you also had this really powerful value around self sufficiency and there was a conflict between you saying, okay, so what if I look at the life of an artist or a writer, and given the upbringing that I’ve had, I don’t ever want to have to rely on anyone else to take care of myself. And it sounds like that was a really interesting struggle that sustained for some time. Yeah.

Debbie Millman (00:16:13) – I mean, I think that any artist making something new and original. Has to be, to some degree comfortable with risk and uncertainty because there is no certainty in making anything original. You don’t know how it’s going to turn out.

Debbie Millman (00:16:28) – You don’t know how people are going to respond to it. And at that point in my life, having any more uncertainty about my survival, about my ability to take care of myself was just more than I could bear at the time. And so I needed to be able to find a way to support myself. That would be. Venn diagram between self-sufficient and creative, and that became commercial art. And ultimately. 40 years later. You know, I’m not unhappy with that choice, but for a very long time felt that I had settled and that I had compromised my dreams, not really understanding that I had to take care of my psyche first before I could really even begin to do anything creative. That was even in the moment, something that I would like. And so it really became a matter of doing what I needed to do to care of my own, sort of. And the Maslow needs that very bottom of the pyramid. And then from there move forward to try to reach self-actualization, which I’m still on a journey to find.

Jonathan Fields (00:17:43) – Aren’t we? All right. I don’t know if there’s an endpoint to that journey. The impulse for you, it leads you into the world of design. You’ve written My first ten years after college were experiments in rejection and despair. I knew that I wanted to do something special, but frankly, I didn’t have the guts to do anything special. What was that about?

Debbie Millman (00:18:02) – Well, I think that that’s that’s going back to what I was saying. It wasn’t so much that didn’t mean. Yes, I didn’t have the guts. I didn’t have the guts because I didn’t believe that my talent could sustain me and that I could have some sort of self-sufficiency through the pursuit of a noncommercial career. And because that would have required. Not knowing when and where I was going to get my next paycheck. That was. I couldn’t have handled that emotionally. I didn’t I wasn’t able to handle that emotionally. And so I needed to find a very steady stream of employment that could ensure that I could live on my own, take care of myself and so forth.

Debbie Millman (00:18:45) – And so inasmuch as I can look back on it now and say, Oh yeah, it was compromised, you know, I felt that I was compromising and I felt that I wasn’t doing what I really, really wanted to do. The non-negotiable for me, in looking at all of those things that I wanted to do, really was survival. Taking care of myself in a way that felt like at least I was setting a foundation for a life that would have some meaning by being able to be safe, being able to live in a place that I wanted to live in, which was Manhattan. And that became the non-negotiable. If I had said to myself at the time, my non-negotiable is to be a poet. Or my non-negotiable is to be a painter. It would have had a very different trajectory. I couldn’t have been in Manhattan. I couldn’t have afforded it. I had no choice. But I mean, it was a matter of choice. There was no way I could live with either of my parents.

Debbie Millman (00:19:43) – And so it would have been a matter of, well, where do I want to live to be able to sustain a life that will allow me to be a painter or a poet, you know? I’m not sure that there even is a place. So I didn’t want to be in a position where I was in any way insecure. And so that required some compromise. But it was also at the time a very specific choice that I can only look back on now and say, I was really lying to myself. I wasn’t I wasn’t really compromising. I was doing the thing I needed to do most. And that might have been an unconscious choice, but it was still a very deliberately unconscious choice.

Jonathan Fields (00:20:22) – Yeah. I mean, it’s you know, it’s interesting, right? Because when you put it in the terms of what is my non-negotiable or my non-negotiables, you know, I think in the world of of pop psychology and self-help and personal development, it’s always like, well, your non-negotiables should lie on the aspirational self-actualization side of the spectrum.

Jonathan Fields (00:20:43) – But that often doesn’t take into account the reality of an individual’s history and unique experiences. And for you, it’s like, no, I want to feel like I just want to survive. I want to know I’m going to be able to take care of myself. There’s nothing more important to me and I will figure out the rest. And that really matters, I think, because I think sometimes people feel like they’re being shunned when they put that in front of the sort of self-expression side of things. Well, I.

Debbie Millman (00:21:10) – Think Maslow’s proven that you can’t reach self-actualization until you achieve the four the four rungs up the pyramid that lead to that top of the of the of the peak. So I think that anybody that tries to circumvent. Their physical safety. Their psychological well-being isn’t going to get to the self-actualization, no matter how much they fantasize about how good it’s going to be when they get there. There are some practicalities that have to be addressed, and I don’t know that. For me. I could have had any other choice because I had been unsafe for so long and so insecure about my bodily autonomy that there was only one direction that I could have taken at the time that would allow me to begin to heal.

Debbie Millman (00:22:01) – That’s really all I needed to be able to do. But I didn’t know that. I couldn’t think of it in that way at that time. And of course, I beat myself up over it because here I thought, you know, I’m squandering any hopes of having a happy creative life by making a decision at 21 to go into the commercial arts so that I could have both some level of creativity, but also have a steady paycheck.

Jonathan Fields (00:22:26) – Yeah, it’s like, Oh, it’s the safe. You’re taking the safe option, but. Exactly.

Debbie Millman (00:22:31) – Exactly.

Jonathan Fields (00:22:32) – Literally was right. Right for you. It’s like and that was the smartest that was the most important thing that you could have done because you weren’t safe before that, you know?

Debbie Millman (00:22:40) – But I wasn’t conscious of that at all. And, you know, I did a commencement speech for the University of California in San Jose, and I it went viral. And it was part of a book on, you know, the world’s best commencement speeches. And in that speech, I talk about how I compromised and how I took the safe path and really came to terms with that in this commencement speech.

Debbie Millman (00:23:06) – And now I look back on it. You know, again, going back to what we just said about thinking something’s good at the time and then looking back in horror, you know, I say to myself now and I and I share with people that I was lying to myself. I wasn’t lying intentionally. I wasn’t sharing this with people in a duplicitous manner. I was just clueless at what I was really saying. Yes, I took a safe path, but it was to be safe. And then from there I could sort of rethread my spirit and my soul. And then and only then really try to begin to do something that I could include my whole heart into.

Jonathan Fields (00:23:42) – Yeah. And I mean, for you, this is this is literally a decades long process. You end up deepening into the world of design. You end up at Sterling Brands, focusing a lot on identity creation and storytelling, identity creation.

Debbie Millman (00:23:54) – There you have it. It’s All right. Which is.

Jonathan Fields (00:23:57) – Again, fascinating, right?

Debbie Millman (00:23:58) – Yeah.

Debbie Millman (00:23:58) – Yeah. How do you how do you create an identity? And that’s and that was what I ended up doing for myself and for, you know, hundreds of corporations around the world.

Jonathan Fields (00:24:08) – Yeah. You know, any given point, I remember the stat, you know, like 25% of what you saw on a grocery store shelf was something where you had your hand in the identity. You also basically decide, I’m just all I’m just going to work, work, work, work, work all the time. And at a certain point, massively successful from the outside looking in a stunningly accomplished amazing at what you do and you write after a life of myriad, albeit inconsistent, creative endeavors. I stopped making art. I quit writing poetry and prose and stopped scribbling my journals. I discarded sewing projects and craft work. I even put my guitar in its case and tucked it under the bed. I was so intoxicated by this new feeling of professional triumph that nothing but more of it mattered. I worked nonstop, traveled constantly, worked ridiculous hours, abandoned my personal life.

Jonathan Fields (00:24:57) – I was in perpetual motion for many years. I had achieved a great deal, but there was an echoing vacuum of meaning and purpose in my life. How do you start to step out of that vacuum when you have spent so many years? Creating it.

Debbie Millman (00:25:16) – In. It’s a great question, Jonathan. How do you do that? I. I had to let go of the trapeze. I was listening to a woman talk many years ago in a conference. She had been the general manager of Puma, and she left that job and started a bed and breakfast in Boston. And. Somebody asked her how she did it and she said that she had to let go of the trapeze and. Have that moment where you don’t necessarily feel safe. But for me, I had this visual when she said that, that both my arms were crooked over the trapeze bar and my legs and my hips and that I was attached. And even if I had tried to let go with one limb or two limbs, all of my other limbs and body parts would be hanging on for dear life.

Debbie Millman (00:26:14) – I was so unwilling at the time to be uncertain. And I think that just the the the more emotionally healthy I became, the less. Attached to what the definitions of success were that I described to. Came like I didn’t feel like I needed to have quite the same. Definitions. Surrounding me and it only really. It was only really forced to show my hands, so to speak, When I was offered the CEO position at Sterling. I had been president for decades and I loved that position. I reported to the CEO. We had a wonderful relationship. He trusted me. I trusted him. That allowed us, I think, both to be really successful doing different things in the organization. And he decided 25 years in or thereabouts that he wanted to consider moving into more of a chairman role and therefore somebody would need to take over the CEO role. And I was next in line. So he came and offered me the position. And at that point, I had been beginning to think about alternatives.

Debbie Millman (00:27:25) – I just wasn’t at a point where I was ready to make any official decision about alternatives. Not even thinking about an alternative as a CEO. But, you know, we were part of Omnicom. We had sold our business to Omnicom in 2008. This was coming at 2015. So I was really astonished in the business and loved being part of this global network and loved being a senior woman in the organization, never, ever thinking about taking the CEO job. That just was not something I just thought Simon would be there forever. I’d be there as long as he was and we’d not that we were in any way romantic, but, you know, we’d ride off into the business sunset together. And when he told me that. I felt somewhat obligated to take the position from a cultural point of view, like it’s important to have, you know, a gay woman CEO representing out there and felt that I had maybe earned it in my career and what a wonderful capstone this would be. And then I could start doing my other things.

Debbie Millman (00:28:26) – But at that point, it’s like, if not now when, then I’m going to get on a whole other roller coaster. And that job would require me. I had just gotten to a place with my work at Sterling in my position where I was able to navigate juggling other projects and other more creative, less commercial endeavors. I was doing the podcast. I was writing books. If I had taken the job, I knew that that would all have to come second. It would have to. Here I’d have an entire global company depending on my leadership. Everyone in my life thought I was going to take the job my brother was putting, like taking bets. And it took me four months, but I decided to turn it down. And really it was it was Simon’s nudging that really led me to the conclusion when he said, Debbie, I think you really need to think about why it’s taking you this long to make a decision. If it takes you this long to make a decision, maybe you don’t want to do it.

Debbie Millman (00:29:22) – And he was right. I didn’t want to do it. And so I didn’t. And that really led me into the sort of life that I have now, ultimately leaving the company about a year later. At that point, I did plan my exit strategy and. One of the interesting things that I learned when you’re on this precipice of making a change. I don’t know if it’s human nature or if it’s just my personality style. The only way I was able to envision the future was with less than what I had. Less power, less identity, less money, less whatever. Any number of things. Certainly my paycheck was going to be different. My my ability to lead was going to be different. There would be so many different things. I never, ever really fantasized about what I might. Receive in doing this just in the feelings of doing it in new opportunities that might come up because I didn’t have any ability to foresee the future. I couldn’t imagine things that had never happened before. So it’s and this is for anybody that’s listening, that’s thinking about making a big decision, I think I’m not the only person that imagines a future with change in it being something that is diluted as opposed to strengthened.

Jonathan Fields (00:30:39) – Yeah, I feel like so many of us think about the second or the third act of our lives. And yeah, without realizing it, like when we paint that picture so often there’s less in it. There’s a simplicity that gets inserted into it and we associate that with less. Yes. And less complexity, you know, because I think complexity. It can bring a lot of amazing stuff. But also stress is one of the things that it brings. It’s just sort of like the nature of the beast when you make that decision. I’m fascinated by these inflection points, especially because for you, you come at it at a moment where you’re like incredibly successful in what you’ve been doing and at the same time you have been building, you know, stunning analytical and design methodology, tools, chops. So and you also over this time started to make an interesting shift in this thing you’ve been doing on the side, like the Design Matters podcast, which is growing. It’s bigger and bigger in the early days.

Jonathan Fields (00:31:41) – You’re primarily sitting down with designers and interviewing them about design. Somewhere along the way, something happens and you’re like, I think I may be more interested in sitting down with creative people, massively creative people, and asking them how they they craft their lives. And I’m wondering if that shift was a conscious one because you were just curious or because you were starting to enter a mode where you’re like, I want to learn like I see myself making some really big changes and I would love to learn how these people navigated something similar.

Debbie Millman (00:32:15) – Very little of what I’ve done in my career was premeditated. Yes, The decision to leave. My corporate position was something I thought about for a long time, but it wasn’t part of a big end game that I had been plotting for five years or anything like that. And with the podcast, that was something that was utterly serendipitous in terms of timing. Something I’d written went, went viral online, and I had this Internet fledgling Internet radio network call me asking me if I’d be interested in hosting a show.

Debbie Millman (00:32:51) – I thought they were offering me a job. They were offering me an opportunity to pay them to produce what really was a vanity project. But I love doing it. And it was for me, it was very creative and I enjoyed talking at the time to designers about design, which is why the show was called Design Matters. And I would say that 6 or 7 years in, I really started to transition to. Broader spectrum of makers. Artists. Performers. Writers. Musicians. The occasional scientist. Certainly still some business gurus. But it was really. Very random and mostly kismet and mostly people that I’d meet asking if they could come on the show and I’d be thrilled and delighted. I’ve always been really scared of asking people to do anything for me. It’s I’m trying much, much, much more to do it now, you know, asking for favors or asking for help. So it was very hard for me to put myself in a position where I had to be vulnerable to somebody saying no. And so therefore I didn’t ask.

Debbie Millman (00:34:01) – But then people started coming to me and when they did, it was so exciting to me that of course they said yes. And that became the first phase of evolution about about the show. The shows change. Yeah. And now it’s very much about the, the sort of I do, I want to put this. It’s almost like interviewing by storytelling. You know, I’m asking people to share their origin story. And so it becomes. A conversation that. Allows people to share their ideas about who they are and and how they make what they make. And that includes decisions. So I think that. It happened organically, more than intentionally. Now that it’s happened, it’s certainly more intentional.

Jonathan Fields (00:34:53) – Yeah, I mean, it’s been interesting to sort of watch the evolution and also interesting to see that at least from the outside looking in, you’re comfortable. Holding the original format lightly enough to allow it to evolve, to become something that kept being genuinely interesting to you 17 years later. Because if you think if you ask the average person like, are you going to do the same thing for 17 straight years or 20 straight years, a lot of people would be like, I can’t imagine being that same person doing that exact same thing.

Jonathan Fields (00:35:20) – But at the same time, when you’re building an audience or a business or a level of status or an income around this thing that you become known for. It’s not necessarily easiest thing to say. This is no longer giving me what I want, even if it’s giving other people what they want for me to stay in it. It needs to evolve with me to suit me to this. I mean, it’s a gradual evolution. At least it was in your case, but it’s also really bold and it’s it can be uncomfortable. Well, thank.

Debbie Millman (00:35:50) – You for saying that. I mean, I did get a every now and then. I was at the beginning, I got some pushback. I think somebody wrote a comment on the iTunes page for design matters. One of the one of the comments was, if design matters and why don’t you interview designers, you know, something like that. And then that’s fair. That’s absolutely fair. I still always interview designers. There’s not a season that has gone by where there’s not at least a handful of really good designers that I’m talking to.

Debbie Millman (00:36:19) – But again, it’s it’s really a deep seated curiosity for me in understanding how the creative mind and spirit works and so that it means that I’m sort of creative agnostic at this point with with who I want to speak to. But again, I could also as passionately talk to somebody who’s making a business as somebody who’s making a meal or somebody who’s making a book or a musical and so forth. But there have been certain trajectories that allowed. There to be at least some sense of validity for having a certain kind of person on the show. You know, when Tim Ferriss was on the show, that grew the show considerably and it allowed me to get other people of his caliber on the show. When Tommy Kail, the director of Hamilton, was on the show, that took me to another level. And so there have been like moments that I can pinpoint and say, Oh, that person helped me. Had gained entry into a whole other genres of of people. Amanda Palmer when she was on the show, that allowed me to get more engaged with musicians so I can pinpoint a few over the years and say if it weren’t for them, I don’t know that I’d have as much success.

Debbie Millman (00:37:33) – And those are all people that I would I would say also Maria Popova, you know, my my ex and my dear, dear, dear friend, you know, she was constantly giving me advice about trusting my instinct and. Really trying to believe in in my ability and that confidence from her. Meant a lot and still means a lot. And she’s always somebody I go to to bounce ideas off of because she’s so brilliant. Yes.

Jonathan Fields (00:38:05) – You know, it’s interesting, the people that you just mentioned in the conversations, all of them I’ve listened to, they’re all conversations that are fundamentally, really focused on the question of how do I design a life worth living.

Debbie Millman (00:38:16) – Yeah.

Jonathan Fields (00:38:17) – Which has really become the sort of the broad, sort of like scope of what you’ve been focused and what both of us have been focusing on, no small extent. And one of the guests that you you had both had on your podcast and interviewed and I know you were a friend, I the great pleasure of just having a single conversation with him years back, back when we were filming video.

Jonathan Fields (00:38:38) – Milton Glazer You know, it’s interesting because he’s somebody who’s known in the world of design for just his stunning, stunning work, but also for the impact that he’s had on so many other people. And your introduction or your one of the earliest interactions with him was a summer intensive that he used to do every year for, what, decades, I guess, where he went decades.

Debbie Millman (00:38:59) – I think he did it for 40 years.

Jonathan Fields (00:39:01) – Right. And and there was one exercise. I remember you telling me that he would introduce at the class and have everyone do. And it wasn’t like here’s like, you know, like this. It wasn’t all about like, this is the design thing or this is a tool or this is a process. It was about life, right? Tell me a little bit about that, because I know that you have since also folded it into your teaching.

Debbie Millman (00:39:22) – I have, sadly. Milton passed away last year. Yeah. At 91. He he passed away on his birthday, which of course is ultimate design symmetry to everything that Milton ever did.

Debbie Millman (00:39:36) – He was a mentor to me. He was very kind to me and I took a class with him in 2005 at the School of Visual Arts. This was before I was teaching there, so I had no connection to the school at all other than through this one experience at that time. And in the class, the final exercise of the intensive was to write out a five year plan for your life and not so much a plan, but a five year prediction, almost like you’re writing it in real time five years into the future. So it is let’s say today is January 20th, 22. It is January 2032. And I am doing this. I wake up and and you’re to write an essay. The directions were to put your whole heart and soul into writing this essay, envisioning what you were doing as if anything, that you wanted to do, you could do without feeling. And he he really did encourage us to put as much energy into it as we could muster because he found that it was a magical little exercise and that students were always coming back to him years later saying, Wow, I did this exercise in your class.

Debbie Millman (00:40:48) – And lo and behold, everything manifested. And so being, you know, pretty desperate for self-actualization, I really did put a lot of energy into doing this. I even made a list of the things that I was doing in addition to writing the essay, and I wrote it in one of my journals and kind of forgot about it. And then I would say eight, nine, ten months later, I was going through the journal, found the essay again, and started to realize in reading it that a couple of the things that I had written in All but forgotten about had started to happen and within. 3 or 4 years, I’d say about 30% of the things. And they were big things like writing a book and running and teaching at the School of Visual Arts, because that’s where I was doing this exercise. And then all of a sudden I’m getting these opportunities and they weren’t things that I was actively pursuing. They came to me. And so when Milton retired and stopped teaching the class, I asked him if I could begin to add that exercise into my own teaching at the School of Visual Arts.

Debbie Millman (00:41:53) – And he said yes. Now, Milton’s class was for mid-level professionals to sort of reboot their creative spirit. I mostly teach young people, and so I extended the runway of of the time from five years to ten years also, because I think it took. 15 years for me to manifest everything on my list. And so I didn’t want people to feel like they had to rush. They could take that slow walk up the mountain.

Jonathan Fields (00:42:21) – Yeah, I love that. I also love it because I think when design is sort of like looked at as a very process oriented, you know, their whole methodologies are in design thinking, human centered design. There’s like there are a lot of Step-By-Step methodologies and ideas and paths and processes. What I love about this is here you have one of the most iconic designers who’s lived basically saying, I don’t want you to write about process right now. I don’t want you to think about process. I just want you to envision in the most detailed possible way with the end state that you dream of being is going to be and just like write it like you’re there and like give it sensory and flavor and smell and taste and color.

Jonathan Fields (00:43:00) – And then you take the same exercise and give it a little bit more time for younger folks. And if there’s it’s like it’s almost like it sets a GPS in your brain and the way that you get there, you know, it just kind of unfolds without so much you’re intentional about the outcome, but you hold it’s almost like your brain is working subconsciously on it for years without you realizing it’s doing the design work and you have no idea it’s happening in the background.

Debbie Millman (00:43:29) – Absolutely. I think that there’s some barriers for people when they’re doing this, and I find that the most consistent barrier is when people start to say, Well, I don’t know how this is going to happen. Like, I don’t know how this is going to come to be or I don’t know how I’ll get to be able to live there. And I’m like, Don’t think about the process. Don’t think about how you’re going to achieve it. Write this as if it’s already happened. You’ve already achieved it. So let’s just put that whole process and way in which aside and just be living as if.

Jonathan Fields (00:44:06) – Yeah, it’s so powerful. One of the things Milton, of course, is, is somebody who you write about in your gorgeous new book, Why Design Matters, along with so many of the other guests had been in your show. And one of the things that you share is something that he also believed in, which is this idea of building an astonishing career, doing really great work, and at the same time a deep commitment to doing no harm. And it seems like he treated design with an almost spiritual reverence that I feel also I see in your work, and I’m wondering whether that’s something that that resonates with you.

Debbie Millman (00:44:46) – Well, that’s the highest compliment you could pay me. So thank you. Um. I think I’ve gotten to a place a little bit more recently where I do see the practice of of branding. You know more. For lack of a better word, because you don’t often hear these words together. Spiritual manner. Milton was the board, the head of the board of directors at SVA.

Debbie Millman (00:45:15) – And so in order for my program to get approved by graduate program in branding at SVA, he had to sign off on it. And I had to promise him that I wasn’t going to create a program that encouraged manipulation and greed, that it was going to be much more about behavioral psychology and cultural anthropology and how we can. Brand movements and use branding to make the most positive changes in the world. And I’ve tried really, really hard to keep it in that realm and. I’m really proud, 12 years in that the work that we’ve done is doing just that and the kinds of clients we work with, the kind of work we’re making is really giving our students the ability to create a world full of this capitalist tool that is. Allowing people to take back the power that they’ve always had, but just didn’t always know that they. Could control and using it more for demanding behavioural change of the corporations that were working with more economic freedom, more rights, equality and doing things in a way that doesn’t put profit first.

Debbie Millman (00:46:39) – And so really taking the corporation in many ways out of the equation because corporations have a fiduciary responsibility to the shareholder while people have responsibilities to each other. So how do we use the tenets of branding to begin to insist on the kind of world that we want to live in through branding? And that’s the work we’re doing?

Jonathan Fields (00:46:58) – Yeah, which is not the association the average person has when you tell them the word branding. Exactly. It’s usually just more like what is the corporate identity that is going to tell the story in a way which will sell the most product. But so it’s really interesting to zoom the lens out and say, how do we use these same ideas to tell the story of the world we want to live in and then inhabit that space and then make it real, which I think also really speaks to the moment that we’re in right now. You know, so we’re we’re having this conversation at the beginning of 2022. It is at a time of profound disruption, profound ground, profound upheaval. There’s a lot of pain and a lot of suffering that has been a part of that process on a lot of different levels.

Jonathan Fields (00:47:42) – And at the same time, like there is no such thing as uncertainty with possibility, right? Two sides of the same coin. So when you look at this moment that we’re in right now and you look at the opportunity that we have to tell a different story to step into this moment differently, what types of things are you thinking about on a regular basis that are really just like on your mind when you think about where how do we navigate this moment? How do we tell the story and and how do we do it in a way that lets us get somewhere better?

Debbie Millman (00:48:13) – Well, I think that some of the most exciting developments, for lack of a better word in branding, include things like Black Lives Matter and Me too, where we’re using the exact same tenets of branding to create a a cult of personality around a pair of sneakers to demand societal change. And so there’s a logo and there’s a website and there’s an Instagram account and followers and believers and so forth. But the energy and inspiration used to create those movements is being done in a way that is improving the way we all can live and be in the world together.

Debbie Millman (00:48:56) – So that’s the kind of work that I’m much more interested in. And also understanding why we have the relationship that we do to certain brands or certain things. For example, I don’t think that we’re really addicted to our devices. I think we’re addicted to the feelings that we get through our devices. And so that’s the kind of thing I’m much more interested in understanding than looking at algorithms and ways of engagement that are perpetuating bad habits more than good. And so, you know, it’s not about whether branding is a good thing or a bad thing, which is what a lot of people like to argue about. It’s really about why we have been using the tenets of branding as far back as 40,000 years ago when we were beginning to record our reality on the cave walls of Lascaux and more recently, 10,000 years ago, when we started to create symbols to signify our affiliations and our beliefs through religion. These are all the same behaviors just sort of presented in slightly different ways and in some cases not presented differently. So this is this seems to be an innate human behavior that’s hardwired into who we are and how we express ourselves.

Debbie Millman (00:50:09) – And we have to make very deliberate, intentional choices every day about how we want to use those ways of expressing to to do no harm.

Jonathan Fields (00:50:20) – Yeah, it’s so powerful as you’re sharing that. I was thinking about some of the ideas of Jean Sharp, who they passed a couple of years ago, but he was one of the leading theorists around Nonviolent Revolution and wrote this book, which was almost like a giant pamphlet called From Dictator to Democracy that ended up being sort of the the guidebook for many nonviolent revolutions around the world. And, you know, one of the things that the reason I was thinking about it when you were sharing that is that, you know, he said it’s really important when you’re sort of like telling the story to not just focus on what you don’t want, but you’ve got to be able to tell the story of what you what you do want and what, what, what are you going to create in its place. And I feel like we’re in this moment right now where we’re really we’re we’re getting clearer and clearer and clearer of like, what must end.

Jonathan Fields (00:51:05) – But the other part of the story is like and this is what I believe is important in what what we want to create moving forward. Yes, that’s a harder story to tell because it doesn’t yet exist in a lot of ways. So it’s harder to. Point to specifics because we know the qualities that we want in place, but it’s easier to almost tell the story of what we want to tear down or end because we can point to it correct. Whereas we’ve got to envision what we want, the story of what we want to step into. Yeah. And I think sometimes we have like this is such a beautiful example of why we need people who are inspired to insight and tell and step into this process of telling that story because it’s not easy and people don’t go there as easily as the sort of like the tearing down side.

Debbie Millman (00:51:53) – Absolutely. Jonathan, thank you for saying that. Yeah.

Jonathan Fields (00:51:58) – I want to start to come full circle with you as well in this conversation. So I’m curious, you know, you you had this stunning career.

Jonathan Fields (00:52:07) – You’re doing work that is really just so rich and deep and humanistic. And you’ve got this gorgeous book, by the way. It is if anyone, like, wants to just curl up with a book and go back to it and visit it and read stories and it’s just it is absolutely beautiful and wise and 17 years of wisdom and conversations from other people and an entire life of your own insights and wisdom when you think about this world that we’re living in right now. And I’ve asked you this question in the past, but you know, different times, and it’s the question that I tend to wrap with everyone if I offer up the phrase that this given a moment in time to live a good life, what comes up?

Debbie Millman (00:52:50) – Love freely. To love freely. To love unselfishly with an open heart.

Jonathan Fields (00:52:56) – Thank you. Hey, before you leave, if you love this episode safe bet you will also love the conversation that we had with iconic designer and thinker Milton Glazer about building a life of meaning and impact. You’ll find a link to Milton’s episode in the show notes, and of course, if you haven’t already done so, please go ahead and follow Good Life project in your favorite listening app.

Jonathan Fields (00:53:19) – And if you found this conversation interesting or inspiring or valuable and chances are you did. Since you’re still listening here, would you do me a personal favor, a seven second favor, and share it maybe on social or by text or by email? Even just with one person. Just copy the link from the app you’re using and tell those you know those you love, those you want to help navigate this thing called life a little better so we can all do it better together with more ease and more joy. Tell them to listen, then even invite them to talk about what you’ve both discovered. Because when podcasts become conversations and conversations become action. That’s how we all come alive together. Until next time, I’m Jonathan Fields, signing off for Good Life Project.

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