Good Life Project - Debbie Millman | How to Design a Life

Episode Date: February 21, 2022

How 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 | InstagramIf you LOVED this episode:You’ll also love the conversations we had with Milton Glaser about building a life of meaning and impact. Check out our offerings & partners: My New Book SparkedMy New Podcast SPARKED. To submit your “moment & question” for consideration to be on the show go to sparketype.com/submit. Visit Our Sponsor Page For Great Resources & Discount Codes Hosted on Acast. See acast.com/privacy for more information.

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. 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 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 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. 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 consultancies, Sterling Brands, where she worked on the brand identity of everyone from Burger King, Hershey's, Haagen-Dazs, Tropicana, Star Wars, Gillette to the No 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. So excited to share this conversation with you. I'm Jonathan Fields, and this is Good Life Project. this thing. Mark Wahlberg. You know what the difference between me and you is? You're gonna die. Don't shoot him! We need him! Y'all need a pilot. Flight Risk.

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8 hours of charge in just 15 minutes. The Apple Watch Series 10. Available's the fastest charging Apple Watch, getting you eight hours of charge in just 15 minutes. The Apple Watch Series 10, available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone XS or later required, charge time and actual results will vary. So you and I have been rolling together for years now. As we have this conversation, it's the beginning of 2022. We're actually celebrating our 10-year anniversary on Good Life Project. I think your design matters, what, 17 years at this point? February 4th, it'll be 17 years.

Right. And I think the first conversation that we had on your podcast, I think, was actually the 10-year anniversary of it was the 10 year anniversary of, it was the 10th year of your show. So. Oh yeah. That makes sense. Absolutely. Yeah. The 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 cause I, 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 this space and I'm like, not really. Well, I mean, 10 years is still 10 years. 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 in this gorgeous book that you are bringing to the world literally as we speak. I want to take a little bit of a step back in time also before we get there. 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 sort of like defined what would happen. And I was thinking about it in the context of you. I don't know why it 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. It's certainly possible. You know, what didn't thwart Alan's creativity is, I think, what has allowed him to be this remarkable performer. And it's quite exceptional that that didn't really squash him to a point where he couldn't make use of his talents. 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 get over. And I would say that I still suffer from that a little bit, but nowhere's near the sort of paralyzing impact that it had on me probably till my late 30s. 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 the person who stepped in as that role was not kind, is probably a nice word of 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. Yeah, yeah. 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's 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 quite public because there's nothing like revealing the deepest part of yourself on one of the world's most famous, well-listened-to podcasts. If you're going to do it, it's like, go home or go big or go home. 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 in the world. I'm curious, in the history of our entire show, we've had maybe one or two times where somebody came back to us, you know, later, a couple 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, was it almost like the exact opposite? 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 number of things that, you know, the stories we tell ourselves about ourselves. 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 out because they thought they might upset someone with something, with an opinion that they had 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. Yeah, no, 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 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 as like, you know, like this is so critical and so rarely experienced, but even day-to-day

conversations, and I would venture to say over the last two to three 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. 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. And it definitely shows. I remember actually, it was Roxanne, your wife interviewing you. And I was listening to that conversation. I think it was like a guest canceled last minute or something like so. She tagged in and decided to interview you. And she was describing your interview process to an audience of people. And it 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 she's just completely immersed in the

whole experience. Absolutely. Absolutely. I get very, very committed to what I'm doing. Which is just a sign of the genius that makes it so extraordinary. Oh, I 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, but can we dive into that, actually? Because that's really interesting. Sure, sure. Do you think there's a relationship between genius and profound insecurity? No, I actually 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 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 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 the 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. Yeah. I mean, that's an interesting distinction, actually,

because it's almost like a high level of insecurity. Even if you're creating at a high level and innovating at 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? 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 in the 400-meter race. So I think you can be discontent with the results of something that you're doing, but that has nothing to do with insecurity. It's the expectation that you could do better or should do better, I think. Yeah, no, that actually makes a lot of sense. 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 not even count on one hand, count on one or two 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 lens on it. Yeah, 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 have possibly introduced 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. And that's terrifying because then it makes you wonder what you're not seeing about what you're doing today.

Well, yeah, 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? So 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 10 years from now I will have grown like an astonishing amount?

I mean, it's kind of cool. Yeah. Either that or the patina of the newness of it wears off and you're left with what it actually is. Well, that too. There's that risk as well. Yeah. Hindsight is a beautiful thing. Isn't it? Yeah. Whether you're in your running era, Pilates era, or yoga era, dive into Peloton workouts that work with you. From meditating at your kid's game to

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Compared to previous generations, iPhone XS or later required. Charge time and actual results will vary. Mayday, mayday. We've been compromised. The pilot's a hitman. I knew you were going to be fun. On January 24th. Tell me how to fly this thing. Mark Wahlberg.

You know what the difference between me and you is? You're going to die. Don't shoot him. We need him. Y'all need a pilot. 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. 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 when you're thinking to yourself,

what am I going to step into? What is this 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. 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 and 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 a 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 take care of my own sort of 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. Aren't we all, right? I don't know if there's an end point to that journey. The impulse for you, it leads you into the world of design. You've written, my first 10 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?

Well, I think that that's going back to what I was saying. It wasn't so much that I didn't, I 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 non-commercial 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. And so in as much as I can look back on it now and

say, oh, yeah, I was compromised. 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, I 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. 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, 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 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. Yeah. I mean, it's interesting, right? Because when you put it in the terms of what is my non-negotiable or my non-negotiables, I think in the world 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. 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 be 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 think Maslow's proven that you can't reach self-actualization until you achieve the four rungs up the pyramid that lead to that top 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. 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. Yeah. It's like, oh, it's the quote safe. You're taking the safe option. Exactly. Exactly. But literally I was. Right.

Right. For you, it's like, and that was the smartest, that on 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. And now I look back on it, again, going back to what we just said about thinking something's good at the time and then looking back in horror. I say to myself now, 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 re-thread 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. Yeah. And I mean, for you, 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. There you have it. It's all that same path. Which is, again, fascinating, right? Yeah. Yeah. How do you create an identity? And that was what I ended up doing for myself and for hundreds of corporations around the world. Yeah. At any given point, I remember the stat, 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, 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 craftwork. I even put my old 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.

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? That's a great question, Jonathan. How do you do that? 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. I was so unwilling at the time to be uncertain. And I think that just the more emotionally healthy I became, the less attached to what the definitions of success were that I described to became. Like I didn't feel like I needed to have quite the same definitions surrounding me. And it only really, I was only really forced to show my hand, 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. 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 we were part of Omnicom. We had sold our business to Omnicom in 2008. This was coming at 2015. So I was really ensconced 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 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. It's important 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. 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 CEO 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 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's taking you this long to make a decision, maybe you don't want to do it. 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'd had. Less power, less identity, less money, less whatever, any number of things. Certainly my paycheck was going to be different.

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. 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 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. I'm fascinated by these inflection points, especially because for you, you come at it at a moment where you're incredibly successful in what you've been doing on the side, like the Design Matters podcast, which is growing. It's bigger and bigger. In the early days, 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 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. 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 viral online. And I had this internet, fledgling internet radio network call me asking me if I'd be interested in hosting a show. 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 loved doing it. And 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 six or seven years in, I really started to transition to a 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. 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. But then people started coming to me and when they did, it was so exciting to me that of course I said yes. And that became the first phase of evolution about the show's change. Yeah. And now it's very much about the sort of, how 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 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. Yeah. I mean, it's been interesting to sort of like watch the evolution and also interesting to see that at least from the outside looking in, you were 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 and doing that exact same thing. 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 quote 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 too. I mean, it's a gradual evolution, at least it was in your case, but it's also really bold and it can be uncomforting. Well, thank you for saying that. I mean, I did get a little, 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 comments was, if design matters, then why don't you interview designers? You know, something like that. And 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. But again, 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 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 moments that I can pinpoint and say, oh, that person helped me gain entry into a whole other genre 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. And those are all people that I would say. Also, Maria Popova, my ex and my dear, dear, dear friend. She was constantly giving me advice about trusting my instinct and really trying to

believe 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. Yeah. If you're at a point in life when you're ready to lead with purpose, we can get you there.

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charge time and actual results will vary. Mayday, mayday. We've been compromised. The pilot's a hitman. I knew you were going to be fun. On January 24th. Tell me how to fly this thing. Mark Wahlberg.

You know what the difference between me and you is? You're going to die. Don't shoot him. We need him. Y'all need a pilot? Flight Risk. You know, it's interesting. The people that you just mentioned and 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? Yeah. Which has really become sort of like the broad sort of like scope of what you've been focusing and what both of us have been focusing on, no small extent. And one of the guests that you have both had in your podcast and interviewed, and I know you were a friend. I had the great pleasure of just having a single conversation with him years back when we were filming video on Milton Glaser. had on so many other people. And your introduction or your early, 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 would invite people into it. I think he did it for 40 years. Right. And, and, and there was one exercise. I remember you telling me that he would introduce

to 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 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. I have. Sadly, Milton passed away last year at 91. He passed away on his birthday, which, of course, is ultimate design symmetry to everything that Milton ever did. 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 2022. 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 failing. And 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 and lo and behold, everything manifested. And so being 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, 10 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 and things like writing a book and teaching at the School of Visual Arts because that's where I was doing this exercise. And lo and behold, 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, 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 the time from five years to 10 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. 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, what 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. And then you take the same exercise and give it a little bit more time for

younger folks. And it's almost like it sets a GPS in your brain. And the way that you get there, 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. 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 and you've already achieved it. So let's just put that whole process and way in which aside and just be living as if. Yeah, it's so powerful. One of the things Milton, of course, is somebody who you write about in your gorgeous new book, Why Design Matters, along with so many of the other guests that have 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 resonates with you. Well, that's the highest compliment you could pay me, so thank you. I think I've gotten to a place a little bit more recently where I do see the practice of branding in a more, for lack of a better word, because you don't often hear these words together, spiritual manner. Milton was the head of the board of directors at SVA. And so in order for my program to get approved, my 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. 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 behavioral change of the corporations that we're working with, more economic freedom, more rights, equality, and doing things in a way that doesn't put profit first. And so really taking the corporation in many ways out of the equation, because corporations have a fiduciary responsibility to the shareholder. Well, 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 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. 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's going to tell the story in a way which will sell the quote 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 having this conversation at the beginning of 2022. It is at the time of profound disruption, profound groundlessness, 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. And at the same time, there's 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 how do we navigate this moment? How do we tell the story? And how do we do it in a way that lets us get somewhere better? 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 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. 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've 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 Lescaut 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 seems to be an innate human behavior that's hardwired into who we are and how we express ourselves. And we have to make very deliberate intentional choices every day

about how we want to use those ways of expressing to do no harm. Yeah, it's so powerful. As you're sharing that, I was thinking about some of the ideas of Gene Sharp, who passed a couple of years ago, but he was one of the leading theorists around nonviolent revolutions and wrote this book, which was almost like a giant pamphlet called From Dictator to Democracy that ended up being sort of 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're 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 really, we're getting clearer and clearer and clearer of like what must end. But the other part of the story is like, and, and this is what I believe is important in 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 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. And I think sometimes we have, like, this is such a beautiful example of why we need people who are inspired to incite 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. Absolutely, Jonathan. Thank you for saying that.

Yeah. I want to start to come full circle with you as well in this conversation. So I'm curious, you know, you had this stunning career. You're doing work that is really just so rich and deep and humanistic. And you've got this gorgeous book, by the way. If anyone wants to just curl up with a book and go back to it and revisit it and read stories, it is absolutely beautiful and wise. And 17 years of wisdom in 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 at this given moment in time to live a good life, what comes up? Love freely. To love freely, to love unselfishly with an open heart. 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 Glaser 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, go ahead and follow Good Life Project in your favorite listening app. And if you appreciate the work that we've been doing here on Good Life Project, go check out my new book, Sparked.

It'll reveal some incredibly eye-opening things about maybe one of your favorite subjects, you, and then show you how to tap these insights to reimagine and reinvent work as a source of meaning, purpose, and joy. You'll find a link in the show notes, or you can also find it at your favorite bookseller now. Until next time, I'm Jonathan Fields, signing off for Good Life Project. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever,

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Charge time and actual results will vary. Mayday, mayday. We've been. Charge time and actual results will vary.