Good Life Project - Debbie Millman: Imagine Immensities [Best of]

Episode Date: December 19, 2016

Debbie Millman is a creative, design and storytelling force of nature.Millman was drawn into the world of news and print in her early twenties, cultivating an appetite for artful communication, storytelling and news. By her early thirties, though, life had dealt a series of challenges.In quick succession, she found herself without a job or a sense of purpose, bound by her own self-loathing. Unlocking and even mining that negative cycle, though, was the key to her turnaround.She started down a path of discovery that would lead to a series of serendipitous adventures, eventually becoming a leading voice in the world of design, branding and media, and co-founding and chairing the Masters in Branding Program at the School of Visual Arts in New York. She's also hosted the acclaimed Design Matters podcast for 11 years, which was a major inspiration for our show.As Debbie shares in this conversation, you "have to create your own happiness."On this "Best Of" episode of Good Life Project, Debbie Millman gets real about living with uncertainty, creativity and freedom, diving into the world of design, art and media.And, as we reflect on the year behind us, and think about the year to come, she reminds us to imagine immensities, then make them happen.We first aired this conversation in April 2014. I'm so excited to share this "Best Of" episode with you now. Hosted on Acast. See acast.com/privacy for more information.

You have to make your own happiness, wherever you are. Your job isn't going to make you happy. Your spouse isn't going to make you happy. The weather isn't going to make you happy. A restaurant isn't going to make you happy. I think you have to decide what you want, and you have to find that way of doing it, whether or not the outside circumstances are going to participate in your success. Hey there, it's Jonathan, and I'm so excited to be back with you.

As we do pretty much every year, the last two weeks of the year, we bring back really super powerful conversations that have unfolded over the years from our archives. And this episode actually features a friend of mine, Debbie Millman, who is not only a powerhouse in the design and branding world, she's a profound thinker, somebody who takes on the big questions of life. And she's also a stunning artist and somebody who is just beautifully real. She also is one of the inspirations for this podcast. She has for, I believe it's about 11 years now, been hosting the legendary Design Matters radio show and podcast. And I have been a long, long time fan of that long before I met her

and became friends. And her interview style, the way that she brings really fascinating guests into conversations and goes deep with them, was a huge inspiration for me in the early days as I was thinking about how I wanted to create this and inspire a conversation on Good Life Project. This conversation is wide-ranging. It tracks her beautiful career. And it was recorded, actually, originally. It was filmed in this legendary sort of rock recording studio in New York City. And I'm really excited to share this conversation

with you now as a podcast. I'm Jonathan Fields. This is Good Life Project. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest charging Apple Watch, getting you 8 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. Mayday, mayday. We've been compromised. The pilot's a hitman. I knew you were gonna 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.

So cool to be hanging out with you today. Oh, it's so cool to be hanging out with you. Thank you so much. Oh, it's my pleasure. You're like one of those conversations where every time I see it on my little app on my phone, I'm like, oh, must listen now. Thank you. I literally got a cable to plug my phone into my car radio so I could listen to Design Matters. Thank you.

So I have a curiosity about people in the design field, people in the art field, people in the visual arts especially. And I had the good fortune of spending some time with Milton Glaser last year. And great show, by the way. Oh, thank you. Thank you. I didn't want it to end. It was just, you know, such an incredible person, human being. I mean, just the way he looks at the world and gives back to it. And he shared with me that he knew what he was going to do for the rest of his life when he was like five years old. I'm curious, for you, was there a really – because for so many people who are in the visual arts in some level, when I have a similar conversation, they're like really, really young. They just kind of knew. They may not have known they were going to be a designer, but they knew like boom, something just hit them and they felt it and they're like, this is my life.

That happened to me when I was 32. So completely different. Completely different. I have had the complete opposite path. Okay, so take me back then. Let's talk about like the yin and yang here? Well, I did not really know what I wanted to be as I was growing up and experimented all through my childhood with different possibilities. And so for whatever reason, my parents took a lot of photographs as I was growing up. And so there are series of

photographs that I have where I'm experimenting with being a dancer or a fashion designer. And so there are series of photographs that I have where I'm experimenting with being a dancer or a fashion designer. And it's probably good that I didn't become a fashion designer, given those experiments. A cowgirl. And I... You know, there's a lot of demand for cowgirls. There is. There absolutely is. And sometimes I even fantasize what that might have been like as a grown woman. So I really didn't have any sense of what I wanted to be. I loved to do a lot of different things when I was growing up. And it's sort of interesting to see how that mirrors now in my current life in doing lots of different things. But when I was growing up, for example, I had a best friend whose name was also Debbie. And so we both loved magazines. And one summer, we decided that we would make a magazine of our own. And we called it debutante. And love doing that. We drew all the models, and wrote all the copy, not knowing that it was called copy. We wrote the articles and made this magnificent magazine. At least my memory of it is magnificent.

And then I also loved acting and I was in the school plays and I loved singing and I was in pop chorus and the magical singers and all sorts of things. I made all my own clothes growing up because my mom was a seamstress and we didn't have a lot of money. And so the way for me to get new clothes would be to make new clothes. So by the time I went to college, I had absolutely no idea what I wanted to be. I had experimented in all these different ways, but had not landed on one thing. And when I was in school, I majored in English literature with a minor in Russian literature in English translation. Lots you can do with those. Specializing in cowgirlism. Exactly, as much as you can do with a cowgirl degree. The one thing that I did in college that really gave me some type of skill set to make some money when I graduated was working on the school newspaper. I had wanted to do that all through my four years in college. to the State University of New York at Albany, only because my best friend at the time, not

Debbie, but another woman named Tammy, she went there. That was my decision-making criteria. I would have a friend there. Which is not all that different than a lot of people's decision-making criteria for college, I'd like to have thought that perhaps my parents would have been ever so slightly more involved in guiding me towards making a better decision. But I think they were in their own little worlds at that time. I'm a product of the SUNY system also. I went to SUNY Binghamton.

I remember visiting it. And we went up there for the family trip. And it was like a great day because it always is in Binghamton. Yeah, I applied to Binghamton also. Did you? Yeah. And we're driving around and take the tour. And at the end of it, I'm like, I am never going here.

And somehow I ended up going there. I think it was because the campus is shaped in a giant brain. I thought that was cool or something like that. Yeah, yeah. No, I applied to four state schools, four SUNY schools. Right, because that's what you could do on an application back then. That's what you could do in one application, four schools. And that was the extent of it.

I picked Albany solely because Tammy went. And then when I got there, I very, very luckily, serendipitously found out that SUNY Albany had, at the time, one of the best student newspapers in the United States. And I was fascinated by it. The people that were running it at the time were hippies, renegades, mavericks, really counterculture. This was 1980. I actually got to college in 1979. And so I was fascinated by it. It came out twice a week on Tuesdays and Fridays.

And I lived for it. I went up to the paper to the newsroom, which was on the third floor of the campus center, bravely one afternoon in my freshman year, and asked if I could write for the paper. And the editor at the time, who's since become a very good friend and has been a lifelong friend, actually rejected me, not intentionally, but he asked me if I had any examples of my writing or clippings. I had no idea what that meant. And I sort of scurried away, embarrassed, humiliated, and wounded for several years. It wasn't until my junior year, my second semester junior year, that I actually ended up going back and ended up getting an article to write that somebody had, at the last minute, been unable to write that had been scheduled to write.

And then from there, ended up just involving every bit of passion, soul, energy into that experience and ended up being the editor of the arts and features section in my senior year. What was it about being involved in the newspaper that lit you up? I mean, can you kind of pinpoint, like, was there a specific thing that you did there that said, like, wow, I want to do more of that? Well, one of the things that I very quickly realized was that I was much more interested in creating the paper and designing the paper than in actually writing. Right, so it wasn't good journalism. So coming up with the ideas for what the section would be every Friday, because the arts and

features section was a standalone, sort of like the arts and leisure section of the New York Times or like a magazine section. It was separate and it had its own sort of gestalt to it, I guess. Probably not quite as grandiose as that, but it felt that way to me. And I realized very, very quickly that I was interested in the creation of it, the ideas, as well as the execution of the design. And I didn't even know that that was something that you could do, that that was something that people did. I didn't even know that design was a career, was a discipline, was a practice, was anything. Did they have a design department at Albany? They had an art department and they had design classes,

but as far as I know, there wasn't a design major. I took one design class in college, mostly because I loved art and thought that there was some connection there. And then when I graduated, that was the only skill I had, creating layouts, layout and paste up, old school, on a drafting table, and I was very, very good at it. And so I was making $6 an hour at my first job doing layout and paste up. And that's when I had to make a decision about what I wanted to do with the rest of my life. It was only then that I made that decision, and it was a moment that I actually remember as if it were frozen in time.

Not because I didn't want to be a designer, but design was only one thing that I wanted to do. It was the only thing that I could do. But all the other things that I wanted to do, I was actually too afraid to do. So what were some of those other things? Writing, painting, creating things that didn't have a commercial value. And over the next 10 years, I essentially eliminated all of those things that I was doing on my own. They all fell to the wayside in an effort to do the most important thing for myself at the time, which probably saved my life.

But it still felt like a compromise, and that was being self-sufficient, being able to survive. Yeah. Because I didn't have parents that were willing to help me, and I didn't have any confidence in what I was able to do or not. And so I feel that at that moment in time, in the summer of 1983, the summer, as I affectionately call the summer of the police's synchronicity and David Bowie's modern love, I chose a path that I felt would provide security and not creativity or freedom. I made every choice that summer based on fear, not power. Which is such, I mean, and I think that, I mean, there's so much sadness in that on an individual level, but just society-wide, I think that is the prevailing choice that almost

everybody makes. You know, it's like, whether it's because we've been told, you know, that the thing that you really want to do is not valid, it won't earn you enough, and sometimes it won't. Yeah, sometimes it won't. Sometimes it's totally legit. Sometimes you won't earn anything for doing something that you really want to do is not valid, it won't earn you enough. And sometimes it won't. Yeah, sometimes it won't. Sometimes it's totally legit. Sometimes you won't earn anything for doing something that you love. Right, exactly. Or whether it's just something you've developed internally.

So many of us just say, you know, like, I'm going to play it safe and let those things that, like, you know, the real marrow drop away. And what I find, because I teach students now that are on the precipice of going into the real world, I teach seniors now that are on the precipice of going into the real world. I teach seniors in college. And my class is about getting a job, but it's about getting the job of your dreams, not just getting a job to pay the rent. You can actually try to do both right at the get-go than rebooting your life at 32 ten years in because you suddenly realize, I'm getting older, and if I don't do what I want, at some point soon, I'm likely going to die not doing what I want ever. And it's a lot harder to reboot at 32 or 42 than it is at 22. And it's so important that you bring that up also, because I've thought about this so much, too.

And we get to a point, I think we tend to, we stop experimenting fairly early on. We stop dreaming. Right, we stop dreaming. We stop trying to go out there and actually see, can I make this happen? Is it even conceivable that I could take these things that turn me on, that light me up, that give me a sense of meaning or purpose, passion, whatever word you want to use, and somehow mush them in a way which will allow me to sustain myself in the world too? Right.

And we just like, we walk away from it so early. And I think a lot of that also has to do with the fact that so many people, like the rate that we accumulate responsibility in the world these days, it's really young. It's very, I mean, especially with what college costs these days. Yes. You know, it's like you walk out and there are a lot of kids who are owing six figures. So the answer is, it has nothing to do with what I want to do. This is like, I got to pay my loans. That's true. I mean, I graduated with a whopping $5,000 in debt.

Right. But in 1983, that felt like a lot more, especially when you're making $6 an hour. And when those student loan payments come due nine months later, you're suddenly facing bills, you know, bills. My first bills, my first big bills were my student loan payments. And they terrified me. And there was actually even a moment in time where I wondered if I could indeed pay the bills for my college education, my student loans, as well as my rent, as well as my Con Edison bill and my phone bill and whatever else, you know, my, my, my, the cost just to go back and forth to work

on on with tokens. Yeah, back when there wasn't an E-ZPass or a MetroPass. So what happens at 32? That just makes everything change. Well, it's really a bit of a series of 10-year leaps. That first 10 years, I call those first 10 years experiments in failure and rejection. Because everything that I wanted to do, I got rejected from.

And then once I got rejected, I decided that that rejection was the final word. It wasn't that I was rejected and then thought, you know what, I'm picking myself up, dusting myself off, and I'm going to show them. I'd get a rejection and I'd be like, okay, well, now I have to think of something else. Now I have to try something else. Right. So I was rejected from the Columbia School of Journalism when I thought maybe I should try to be a journalist. That was the end of that. I was rejected from the Whitney Independent Art Program. That was the end of that. And so I'd always come back to design to sustain me. Actually, I'd never left design, but I just always fall back on what I could do

to make a living. And then what's really interesting about the choices that I made was I became aware in the late 80s of the New York Design School. There was actually never a better time to be a designer in the late 80s, early 90s, because you had Tibor Kelman, because you had Pushpin, you had Milton and Massimo and Seymour and Paula Sher was getting famous. And M & Company was doing the most radical revolutionary work anybody had ever seen in our generation. You had Double Space. You had Manhattan Design. And all of a sudden, I became aware of what designers were doing around me rather than being insulated in my own little poor me world. And then I really aspired to try to do work that was great.

I looked at the work I was doing, the sort of silly little paste up that I was still doing and typography that I was just wretched, and realized that there was greatness that could be achieved in design. And then sort of decided at 30 that I was going to leave my job, ended up getting divorced. And because I was getting divorced, I was moving out of the apartment that my ex had owned before I moved in. So at 30, I was basically homeless. I moved into an apartment that was infested with fleas and had to leave. So I was homeless, instead of like just trying to figure out where to live, jobless,

and relationship-less. And at that point, that was probably as an adult, one of my lowest points, because suddenly I realized, how do you make a life for yourself? How do you find meaning? How do you find purpose? On some level, though, did you find that freeing? No. Okay. It was nothing freeing about it. It was terrifying.

Let me tell you why I ask. Because there's the classic conversation with J.K. Rowling where she talks about the fact that when she was at the absolute bottom, that being at that place gave her the freedom to create on the level that she has now like we all know that she can create because she there was no longer anything to risk by putting her real voice out into the world like she hit rock bottom and she's like I can't go anywhere else so let me just go out there and do this thing that I'm here to do and see what happens. That, I think, is remarkable in that she had a voice that she recognized as being worthy of putting out there. Which was my other question. Because the language you used was, I saw that there was greatness in design.

What the question was, did you see there was greatness in you at that moment? No, no, no. And that's been a lifelong process in trying to uncover. I desire greatness, and I'm dogged and incredibly persistent and want so badly to be great. But there's never been a moment in my life that I actually have felt that I was great. But I desire it so much and want it so badly that I can't help but try to keep achieving something that might be close to it, if at all possible. And so at that point, no, I didn't feel like there was any freedom. In fact, I felt bound by my own insecurities and my own sense of self-loathing.

So at that point, and it's interesting because I very, very recently found diaries. I kept diaries from 1973 until 1992. And I've been going through them and reading them all. And I realized just how low I felt and how hopeless I felt about life. It's sort of interesting. I think as you grow as a person, as a human being, you sort of somehow think you're still the same person. You're just bringing all of those experiences along. And yes, you've realized more, but you're intrinsically the same person.

And I guess I've been thinking a lot about that because now that I'm in my 50s, I feel like I'm still 14. But then when I went back and read my journals at 14 or my diaries, I am definitely not 14. And I am nothing like that 14-year-old person, nor am I like the 32- or 42-year-old person. But going through that is what gives you that clarity, seeing how far you've actually come, how there isn't quite as much self-loathing, how there isn't quite as much insecurity. It's still there, but it's not the prevailing emotion. share with anybody that feels self-loathing or insecurity in their 20s or 30s or 40s or 50s is don't give up hope that that might not ever go away. Because I think it does. I've done about now 200 interviews. I'm close to my 200th episode of Design Matters. And then there's been all sorts of live events that I've done over the years. And then all the interviews that I've done for brand thinking and how to think like a great

graphic designer. And the one common denominator that I can share that great brand thinkers, great cultural commentators, great designers have shared with me over the years is that they all feel like they have to get up every day and do it again. They all feel like they very well may be discovered as phonies. They very well may never, ever achieve what they'd hoped. The only two people in all the years that I've done this that have been different in that, that have had a different experience in articulating who they are and what they believe, are Milton Glaser and Massimo Vignelli. But I think the common denominator that they share is that they're both in their 80s.

They're both in their 80s. Like, I think by the time we're 80, we'll be like, okay, you know, this is who I am. Right, knock on wood, you would hope. Right, right. Either that or you don't have any idea who you are. You're like, I'm good. Right? So I actually think that I feel a little bit less self-hatred and feeling self-loathing.

It's very meta, but I think it works. It's a normalizing experience. Exactly. Exactly. Exactly. That's so fascinating, though. I mean, is it a necessary precursor? I don't think so. I don't think so either. I don't think so. I think that if you have a real sense of what you're capable of, it makes it a lot easier to achieve it. I don't think that great athletes wake up every day and think, you know, I'm a fraud. I can't run that fast. I

can't swim that fast. I don't think so. I don't think so. And I come more out of the entrepreneurial world where, and so I'm trying to like do the overlay there. And so many times, I know a lot of people where, if anything, I had a great conversation with Jerry Koloda, who's kind of like a legendary venture capitalist now turned Buddhist coach. Super smart guy. And I was asking him why. And he mainly coaches startup tech entrepreneurs, stuff like that. I said, what are you drawn to about that? And he's like, I love to work with people who are delusionally optimistic. In the entrepreneurial world, there is this certain amount of you almost have to be that way because the odds are so stacked against you.

And you have to believe that everything that everybody else says is impossible is possible. Yeah. Even though everyone around you is probably telling you it's not. Yeah. telling you it's not. But what's so interesting to me, when I look at the world of, you know, like, quotes, art, capital A, art, there's such a radically different culture around success and around what, like, around the assumptions that fuel, like, what's the mindset that you have to bring to this endeavor to succeed? And it seems like there is, there's so much, there seems like a lot more self-loathing in the world of the arts than in the world of, like, entrepreneurship or athleticism, which I don't really know all that well. You know, you could be a great artist.

You could have a truly original voice, a truly original way of working. You could break new ground and never make a penny. It's very, I think, rare to imagine a great businessman. I mean, yes, there have been great businessmen that have lost it all, but then they've usually gotten it back. Otherwise, they're not considered great anymore. sleepy. And it's the fastest charging Apple Watch, getting you 8 hours of charge in just 15 minutes. The Apple Watch Series X. 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. Mayday, mayday. We've been compromised. The pilot's a hitman. I knew you were gonna 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 gonna die. Don't shoot if we I think that successful businesses make money.

Successful art, kind of a crapshoot. It depends on timing. It depends on how well you can promote the work. It depends on the conditions that lead to the conditions to you being successful. It's, I think, a very different set of criteria for evaluating success in the art world. I could be wrong about that, though. I absolutely could be wrong about that. I think on the business side, you're right. Obviously, if you just flame out nonstop and then go away, nobody's going to look at you and say, wow, that was a phenomenal founder,

entrepreneur. Do you think it's changing in the art world, though? Do you think your ability to go out there and use all sorts of digital tools and platforms to build, like, to basically cut out the middle person and go direct to the people who might go out there to set up, you know, like, all sorts of things where people can see your work around the world. I think it makes it a little bit easier to get the work out there. But I don't think that anything's changed in the ability to create original work. I think that one of the unfortunate aspects of the technological world that we live in is the a 140 character culture. Because we expect things to not only happen instantly, but also to be expressible in this sort of very, very sort of short, telegraphic manner. I was doing a lecture for a group of students several months ago. And I was talking about how long things can take. I mean, I feel that I didn't really achieve in the sort of classic achievement model, anything that would be

considered successful, really, until I was in my 40s. And a young woman raised her hand at the end of the lecture in the Q&A part and asked for some advice, because she had started a blog. And she was hoping to get some pointers on how to get people to come to the blog to read the blog, because she was feeling very discouraged. She'd been doing it for a while, and people weren't reading it, she wasn't getting any traction. And so of course, my first question was, how long have you been doing it? And very sincerely, very earnestly, she said six weeks. And because of what I do, I get that nonstop also. Six weeks.

Years, years, years. Like I can't even come up with an idea in six weeks, let alone a viral blog. So I think that there's this, and this is, I think, a really unfortunate ramification from this 140-character culture, is that people in their 20s, when they graduate from college, expect that they have to be successful. And that if they're not successful in their 20s, or if they're not successful sort of right out of the gate, that there's something wrong with them. And then that builds to this real sense of hopelessness, because they haven't achieved

something quickly. First of all, I don't know that I would even want to achieve something in my 20s looking back, anything significant, because then you have to maintain it. Then you have to keep doing it over and over and over. You have to keep hitting the home runs. I'd much rather build to something that could conceivably be sustained just because of the length of time it's taken for you to get there. But in your 20s, look at you. Yeah, exactly.

I mean, that's what you want. I also, a couple of years ago, I did a favor for a friend. Her kids were in school, and she was responsible that year for hosting the Halloween party. And so she enlisted a lot of her friends to be like different characters at the Halloween party. And I became the fortune teller. And so I had this sort of parade of little kids, probably anywhere from six to 12 coming by. And I talked to them and look into the future, you know, what do you want to be? And you know what they were saying over and over again? Not baseball player, not fireman, not nurse, not actress, not singer.

They said famous. That doesn't surprise me at all, which is bizarre. I mean, famous just because you want to be famous. Because that's what our culture now says. Like, that's what it's all about. But, and this is where I think we run into trouble in terms of being fulfilled. If you think about it, our grandparents didn't come home at night and talk to their spouses or their siblings or whoever about whether or not they were happy at work. It was about how they were going to survive.

Right. I'm putting food on the table. Exactly. I'm going to move over the head. Supporting their families, supporting themselves. You have to make your own happiness wherever you are. Your job isn't going to make you happy. Your spouse isn't going to make you happy.

The weather isn't going to make you happy. A restaurant isn't going to make you happy. I think you have to decide what you want, and you have to find that way of doing it, whether or not the outside circumstances are going to participate in your success. And for people that want to create something meaningful, if you're not getting it at work, then do it at home. If you're not getting it every day in the workplace, self generate your own work, make what you need to do to be happy. Even if it's even if other people think it's crap, even if other people think it's crap, even if other

people think it's terrible. You have to be able to create your own happiness, period. And if you can't, then you need to find a good shrink to help you figure out what it's going to take. 22 years and counting here, and she saved my life. I would not have been able to get out of that bubble of self-loathing had I not worked really, really hard to figure out why it was there to begin with. Yeah, and I think so many people look externally for that. They're like, if I do X, if I achieve X, if I get X, then I will be happy, fulfilled, meaning whatever it is.

And there's really fascinating research now going in the field of positive psychology that shows, no, it's completely reversed. You know, like, if I make myself happy, if I make myself content, then I will flourish and I will be better at my job. I'll be better in my relationships. I'll be better in all of these other things. That the work comes from the inside first. And then all the other stuff comes. I'm sorry to interrupt.

No, go ahead. One of the essays that I wrote in Self-Portrait is about an experience that I had in my first job and how I thought, well, if I save up $1,000, I'll feel impervious to any outside insecurities. I will feel safe. And this was 1983, 84, so $1,000 was a bit more than it is today. But as soon as I got that $1,000, I thought, okay, that's not going to be enough. I need $2,000. And it's never enough if that's what you're using to gauge. It's just a little bit more.

Yeah, yeah. And then there's other things that you want. Oh, look at that cute little handbag. And then suddenly you need these outside things to buoy up an otherwise feeble soul. Yeah. I mean, it's a facade, basically. Yeah. So you mentioned this book, which is fabulous, by the way.

Thank you. I'll hold it up. Woo-hoo. It's not a book. I mean, it's in the form of a book, but it's just a stunning blend of memoir, storytelling, writing, art. When does this part of you start to emerge?

Is 32 when you start to reconnect with this? So 32 is when I reconnected with this, but it was because of how unhappy I was elsewhere. Right. So I started, every time I would get a big rejection, I'd retreat into my personal work. Sort of interesting. Like, what's the common denominator there? And let's figure that out.

But I would always retreat into my personal work. was prior to being even in an environment where I could witness or learn from great, great designers that were doing work that I did admire. And ultimately, I was able to get a job where I could learn. And that was the interesting thing about learning was part of what stopped me from even trying to be a journalist. I got rejected from Columbia School of Journalism because I didn't feel like I could be a journalist with the skill set that I had. The only skill set that I had was paste up and layout. And so that's why I chose to pursue the world of design. I mean, then when I got rejected from the Whitney program, I then felt that I was no longer sort of allowed to be a professional, whatever it is that I wanted to be. And so back when I was no longer sort of allowed to be a professional, whatever it is that I wanted to be.

And so back when I was designing and sort of going back to the world of design every time I got a rejection, and because then suddenly I realized, oh my God, the world of design is so much bigger than I thought. And there's so much more that could happen. And oh my God, it is artistic, and it is creative, and it is inventive. because I suddenly became so unhappy with the work that I was doing, I then retreated once again into art and started doing paintings that were based on stories that I had written. And for lack of a better word, I was drawing words, drawing and painting words, whether they be single words or paragraphs. And then once I got the job that ultimately helped me understand what the possibilities were for me in the world of design, which was a job at Frankfurt Gibbs Balkind in 1993, then I stopped doing any artwork at all.

And I stopped doing any artwork at all to dedicate myself to the world of design and then ultimately the world of design and branding. And became incredibly single-minded to have a career, to really have a successful career. Were you happy? It's a loaded question. It's a loaded question because I was trying really hard to be happy. I was working really hard to understand what happiness meant for me. And then for quite some time, I felt really happy that I was being able to create a life for myself. I was able to buy an apartment.

I was able to take care of myself in a way that I'd never imagined. I had never imagined being able to own my own home. I had never imagined being able to have nice things. And so that was a really good distraction for about 10 years. It really wasn't until the middle of, I would say, the early part of 2000. It was about 10 years into doing that. So that 10 years that I suddenly realized, and because I had learned so much about branding by then, that believing in the brand or thinking that these outside

things could provide any sense of long-lasting happiness was a fool's game. As Dan Pink says, if our idea of happiness is a widescreen TV, then we are living in a fool's game. It's just this treadmill, this hedonistic treadmill. And it's like the $1,000 to the $2,000, like the 52-inch screen to the 64-inch screen. It's like the Volkswagen to the Porsche, whatever. You always want, want, want, want, want, because it's not really ever going to fulfill you. It can contribute to a sense of who you are, but it isn't going to define who you are.

And that was a very hard realization. And at that point, I took Milton Glaser's summer program, summer intensive, in the summer of 2005. And I had just already been dabbling with design matters and had no idea at that time. First of all, there were no podcasts in 2004 when I started the podcast. There were none. Actually, I started the idea of Design Matters at the end of 2004 but did my first broadcast in February 2005. So was it like internet radio or something like that?

It was, and two handsets. So instead of this, you and I would both be on a handheld landline. That's how I did it. And never, ever had any idea that it would be something that people would be listening to eight or nine years later. What made you, I mean, what was it that made you want to say? I got a cold call from Voice America Radio. Actually, I didn't even get the cold call. Somebody in my office got the cold call and thought it might be something that would interest me.

And they were looking for people to be hosts of radio shows on their radio network. I had to pay them for the airtime. But it seemed so, I was so curious about designers and how they got to where they got. What was the arc of their journey? What was the arc of their lives? It's like the show gives you a platform to gain access and to justify, okay, let me go on this journey. It gave me a legitimate reason to be nosy, to ask all the questions that would be kind of a little bit stalkery or creepy if I were having dinner with them or if I saw them at a cocktail party. So suddenly, and I started with my friends first, and then I did get some criticism about the sound quality.

But at that point, I was like, you know, I don't even know what I'm doing, let alone the sound quality. And then over the years, I was able to first get better sound within Voice America and then Design Observer and the late, great Bill Durantel, who we just lost a couple of months ago. I really credit him with giving me a platform to be able to do the show. And he really, he threw the gauntlet down. He was the one that said, Debbie, you have a great show.

You do a really good job interviewing people, but you have to take it more seriously. You have to do this. The sound has to be better. You need a producer. You need to be edited. And he put me in touch with Curtis Fox, who has been my producer ever since. And we're approaching our 100 episodes together.

And I don't know that I would have had the courage to take it more seriously had Bill not said, I want you to bring it to Design Observer, but I'm not going to take it unless you do this the right way. And that's really why that happened and how that happened. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether

you're running, swimming, or sleeping. And it's the fastest charging Apple Watch, getting you 8 hours of charge in just 15 minutes. The Apple Watch Series X, 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. 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 if we need him. Y'all need a pilot?

Flight risk. So, what about getting back to your art, though? So, um... Not that I'm minimizing... Not at all. Like I said, addict of the show. Somebody who's, like, building my own sort of, like, radio podcast.

I'm fascinated by what you have to do. Well, in 2005, I took this class with Milton Glaser. I took it at a time where I was like, what next? What next? At that time, from the outside looking in, would the world have said, oh my God, Debbie is so successful? No, no. They would have thought,

she does some cool podcast, but the sound is really bad. Okay. And again, I don't even know that they'd use the word podcast at that point. But I mean,

in terms of the rest of your career, like what you were doing. They would have thought that I was commercially successful. They would have thought that I do well in the sort of big, mainstream world of design. It wasn't well in the sort of big mainstream world

of design. It wasn't artistic in the way that M & Company was artistic, or Winterhouse was artistic, or Pentagram was artistic, and also commercial. It was very much, you could go into a supermarket or a drugstore, and probably 20% of what you saw in the supermarket or the drugstore, I had a hand in somehow designing or art directing. Some better than others. You know, I worked on the design of Burger King, the identity for Burger King. And that was, you know, by 2005, it was the global design, the Hershey bar, Gillette all over the world. So, yeah, Tropicana, the good one with the straw and the orange. You would have known my work.

But it wasn't something that I felt was successful artistically. It was successful economically. It was successful culturally in some ways because people really liked the brands, loved the brands, were zealots of the brands. But in terms of my purpose on this planet, not so much. And that's why I took Milton's class. It was touted as a really good class for people mid-career that wanted to shift the focus of what they were doing and sort of find their inner courage. And it changed my life. It absolutely changed my life, where suddenly, Milton was very, very clear about defending your life, about owning your choices, about making the choices that you hold yourself to, as if you had no issue with succeeding. What would you do if you weren't afraid?

What would you do if you didn't have to worry about being successful? And he has you envision your whole life, your entire life, five years from that moment in time, if you could do anything in the world that you wanted, what would it be? And you have to own it. You have to defend it. You have to declare it. And he talked about the magic in that

exercise, and how over the 50 years, he's been teaching that this particular class was the most important class that he taught, and how it transforms lives. He talked about how he'd always heard from people that that exercise, that class was the defining moment, the before and the after, and that was what it was for me. And suddenly I had this scenario, this vision, and that is what I think has helped propel me to lead a more purposeful life, to feel that what I'm doing is coming from my heart and not my head so much. And it's still, Jonathan, it's still a struggle. I still wake up and think, why am I still doing that? Or why am

I still doing that? And I think I'm afraid of making the change. I'm afraid of, I'm always afraid that this is my last chance, my last chance for happiness, my last chance for love, my last chance for success. But reading through through the journals I felt that way at 19 amazing to see that I'm sure and then it's like whoa yeah you're like apparently it's not right but how do you get like how do you stop if you see this cycle going on in your life for you know like decades how do you break that cycle I guess it's one of the big questions that I have because Because I don't know anybody that doesn't revisit that place at some point. You know, and I think it's...

I've done it by probably taking on too much because I'm afraid to give up stuff. I'll take on new things and still do the old stuff. That's become a little bit untenable because now it's gotten to a place where there's and you know i'm a big proponent of busy as a decision you you decide what you want to do and the things that are important to you and you don't find the time to do things you make the time to do things and if you aren't doing them because you are too busy it's likely it's not as much of a priority it as

is what it is you're actually doing. And that could be watching reruns of Law & Order SVU. You know, I do that all the time. But you have to own that. You have to really say, okay, I know that this isn't as important to me as watching Olivia Benson get the bad guys. But that's then I think knowing it helps. What I've done, because I'm so afraid of giving something secure up for the unknown, is I've kept the secure and then taken on the unknown.

I think you have to, you know, there's that scene in the third installment of Indiana Jones where Harrison Ford just takes a step. I think you have to do that. I don't think you can achieve anything meaningful without taking it.

I completely agree. There will always be a moment. And it's like, and I see this in art, I see this in entrepreneurship and business, any creative endeavor, actually, where the vast majority,

I think when you're a kid, a lot of times, you're much more comfortable just saying, yeah, let me just take the risk. Yeah. But the further you get into life, the more you want,

like, you don't want to go back to that place. Right. You know, so the route to success that I've seen for a lot of people that have gone from that secure mainstream gig that was kind of heartless to something that was more, you know, like heart-centered or wholehearted and also took care of them in the world, it's really rare that I've seen somebody actually cold break and jump. It's almost always build on the side, build on the side, build on the side. And then just like you said, at some point,

it always happens. You reach a point where this thing is here, this thing is still going, and you know, you can feel in your bones that that next thing, it's got a trajectory, but it's not guaranteed, but you can see where it's going. But the only way that it's got a trajectory but it's not guaranteed but you can see where it's going but the only way that it's going to get there is if you finally give up that main thing so at some point you still have to make that and it's not going to be guaranteed and I don't think that that ever changes

I think in order to take that next step you literally have to take the step and hope the ground is beneath you but to answer the original question about the art, in that class with Milton, I made a list. I love lists. I made a list of all the things that I still dreamt that I could do or achieve or experience. And it wasn't a bucket list. It was like 12 things.

And I put the list away. I finished Milton's class. And then I started to try ever so sort of elegantly or inelegantly to take the steps to try to get a few of those things. And once a year now I reread the essay that I wrote and then I look at the list and it's mind-boggling. Because there are things on the list that I actually forgot were on the list and it's scary how so many of them have become something that has manifested.

Milton says it's magic. Maybe it is. The further I get into life, the more open I am to it. I'm a very science-minded person. But the further I get into my career, my life, everything, the more I become like me and the woo-woo scale.

I'm getting more and more comfy with it. Absolutely. Because if stuff happens, there's no rational explanation for why the world rallies up and supports you when you actually go out there and and you know like do what you're really here to do and even though it terrifies you it's it is yeah it's interesting how stuff like that happens but um yeah and Milton Glaser also somebody you know in our conversation and and he's written about this plenty of times also where you know his his fierce resistance to being

defined as like having a style. Where people would come to him and say, well, you're known for this, so they want to hire him so he can do the stuff that's consistent with his. And he wants to do the stuff that he's never done before. Right. So it's because he wants to push. Yeah. And he wants to grow.

And he has endless ideas. Right. And what was so fascinating to me is, like I said, he's 85 now. I get that now. But from everything I can gather, he was like that in his 20s. Yeah. Which is so remarkable. I think it's the result of good parenting.

So remarkable. I'm thinking as I'm raising my daughter, okay, lots of notes, lots of notes. Yeah, yeah. So the name of this project is Good Life Project. Yes. It's an exploration of what does it mean on an individual level to live a good life. So when I offer that out to you, what does it mean to you to live a good life? Imagine immensities.

Try to pick yourself up from rejection and plow ahead. Don't compromise. Start now. Start now, every single day. I love that. Thank you so much for sharing the conversation. It's been wonderful. Thank you, Jonathan. Thank you so much. Pleasure. Hey, thanks so much for listening. We love sharing real unscripted conversations and ideas that matter. And if you enjoy that too, and if you enjoy what we're up to, I'd be so grateful if you would take just a few seconds and rate and review the podcast.

It really helps us get the word out. You can actually do that now right from the podcast app on your phone. If you have an iPhone, you just click on the reviews tab and take a few seconds and jam over there. And if you haven't yet subscribed while you're there, then make sure you hit the subscribe button while you're at it. And then you'll be sure to never miss out on any of our incredible guests or conversations or risks. And for those of you are awesome community who are on other platforms, any love that you might be able to offer sharing our message,

which is be so appreciated until next time. This is Jonathan Fields signing off for good life project. We'll see you next time. Don't shoot if we need them! Y'all need a pilot? Flight risk. The Apple Watch Series X is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest-charging Apple Watch, getting you eight hours of charge in just 15 minutes.

The Apple Watch Series X. 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.