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If Not Now, When? with Debbie Millman

Hey everybody, how's it going? I'm Chase Jarvis. Welcome to another episode of Chase Jarvis Live, here on Creative Live. This is where I sit down with the world's top creatives, entrepreneurs, and thought leaders and do my very best to unpack actionable, valuable insights with the goal of helping you live your dreams in career, in hobby and in life. My goals is to connect you today to the one and only, Debbie Millman. Welcome. (energetic music) (clapping) They love you. So, so happy you're here. Oh, I'm so thrilled. I'm gonna give some context. So we are here, well we've been friends for some time. You've been on Creative Live before, we met, I don't know, a year and a half or so, ago. At the How conference, remember? Yes. At the How conference in Hotlanta. And we're here this weekend in particular because of something you put together for Print Magazine. You want to give a little bit of background on that? Well, last year, I became the editorial and creative director of Prin...

t Magazine. Amazing. And we, well, it's sort of an interesting, there's a really interesting backstory. So, when I graduated college, my dream was to work at a magazine, but it wasn't just any magazine. I wanted to work at Vanity Fair Magazine. Of course. Now, this was back in the 80s and it was pre Tina Brown. It was a magazine at the time that was really more of a literary magazine with a bit of a focus on art. So, one of the first covers they ever had was of David Hockney in a boat and all you saw were his shoes and his socks in the bottom of his pants. Like a rowboat. It was beautiful. Wow. Probably didn't sell a lot of copies on the news stand. I was gonna say, I'm wondering what sock magazine today would, but conceptually interesting. And at the time, I was the editor of the arts and features section of my college newspaper, which meant that I not only edited the paper, but I also designed it, and that was when I first became a designer. And so, in an effort to get this job at Vanity Fair, I mocked up covers and I did these sort of, very German, expressionist Vanity Fair covers. I sent my portfolio in, as you did back then, I dropped it off and miraculously, I got a call back. Charles Churchward was the creative director at the time and I got a call back. But I didn't get a call back to meet with Charles Churchward. I got a call back to meet with the human resources department. Wow. (mumbles) It was the mid 80s. Okay. Bow blouses were in full fashion (laughs) I'm going right there right now in my mind, I get it. My mother was a seamstress and made me all my career clothes. Wow, literally career clothes? Career clothes. Oh, that's amazing. And I went to my interview in a little blue bolero jacket with a bow blouse with little pin dots and sort of, A-line skirt, flat patent leather shoes, slip ons. And I sat across from a woman who looked like she was one day going to star in a movie titled The Devil Wears Prada. Wow. That's what they looked like, even back then. She had this beautiful shift on, beautiful thin arms, a bob and I was this, like, chubby Jewish girl from Long Island wearing a bolero jacket. I did not get the job. But you stood out, probably. You stood out. (laughing) No, I don't think so. Yeah, I stood out like, "Who is that fat Jewish girl from Long Island?" And I didn't get the job and I ended up getting a job at a cable magazine and then a rock magazine, but I'd always harbored this fantasy to work at Vanity Fair. And I started working at Print about 12 years ago as a columnist first, and now most recently as creative and editorial director and one of the first things I wanted to do when I became, when I got this position, was a riff on Vanity Fair's famous Hollywood issue. Get after 'em. You're like, "I'm gonna go there right away." I wanted to do that. And that was what last year's So, last year we did the Print Hollywood Issue: New York. And we got 55 of some of the world's greatest designers that happened to be in New York There's a lot of 'em To come to the School of Visual Arts where they wee donating the space for us for the weekend to shoot all of these incredible designers. And we got Jessica Walsh and Timothy Goodman and you name it, they were there. And it went really well, we had, I think, a 37 page portfolio in the magazine. Chip Kidd was on the cover. It was a record, epic issue for us. And we decided back then, if it did well, we wanted to do another issue the following year, which is this year in San Francisco. So, the Hollywood Issue: San Francisco. And here we are. And you, graciously, have donated your space. We have 60 designers coming through the next two days. And we are going to be photographing the great designers, illustrators, technology, entrepreneurs, if they're something, they're gonna be here this weekend. The list is super impressive. It's amazing. And it's so well curated, you did such a nice job. I'm thrilled to co-shoot this with John Keatley, he's a good friend of mine from Seattle, amazing photographer. The fact that we get to do all sorts of video, interviews of these folks to make available. A, thank you for including me. B, I hope you continue to do this. It's gonna be a staple for the magazine for sure and we've had so much fun working with the folks at Print. And we're just getting started, like, it ramps up really big starting tomorrow morning at like, what, 8:00 a.m. Or something like that? Something ridiculous. Yeah, thank goodness I'm on New York time. Oh my gosh. Well, I'd like to shift the conversation if we can, to that first time when you realized that you could actually make a living and a life doing what you wanted to do. Uh, last month. You think I jest. (laughs) Well, then tell that story. I want to know. Well, this is an interesting time in my life right now. As I mentioned, I graduated college in the early 80s, mid 80s, and I had a degree in English literature and a minor in Russian literature. And I often joke now that I have a degree in reading. Dostoevsky and all them? Yeah, oh yeah. All the great Russian writers. Dostoevsky, Gogol, Tolstoy, you name it, Oblomov, I mean, it's amazing that I read. There's a lot of very long books. Yes. And when I graduated, I knew that I wanted to live in Manhattan and though I'm a native New Yorker, I had never lived in Manhattan before. I had lived in all the boroughs except the Bronx and Manhattan, so Manhattan was number one on the list. And I didn't want to be in a situation where I would feel like I was unstable where I lived. I needed to know that I could pay my rent. There was no option to go back home, so to speak. And so I lived in a fourth floor tenement walk up. It was quite a an interesting apartment. It was a railroad flat. I had to walk through, I had two roommates. They were a couple. And I had to walk through their bedroom to get to mine. Which was uncomfortable at times. I got I think there's a word for that. Isn't that a closet? A room off a room? A room off a room. It was a straight line. Then you had to go through one room to get to the next to the next. And if they were, you know, doing what couples do, I'd sometimes get stuck on either end, which made for difficulties. But it was an interesting time. And it was New York in the 80s. And the only way that I felt that I could be both creative and pay my rent was to be a commercial artist as opposed to a fine artist or an illustrator or a writer or a painter, any number of the things that I really, really with all my heart wanted to do. And so I launched this career in design which turned quite by accident out of desperation, really into a career in branding in my early 30s, so, about 10 years after I graduated, I stumbled into a job in branding. Had I known that that would be what I was going to pursue, I probably would have spent a lot more time paying attention to the things that I was doing in my father's pharmacy because as I was growing up, I worked in his pharmacy. Oh, I love that. Which is where I sort of learned by osmosis about branding. Why people would buy the things they did, why they'd choose the things they did. I was endlessly fascinated by that. Not knowing that it was something I could ever pursue as a career. But always the lead gene in my life was self sufficiency. That's a powerful motivator, right? Well, it was a powerful motivator, but if you don't ever feel like you are entitled or deserve self sufficiency, no matter how much you get, you never feel safe. And I learned that through amassing an enormous amount of things that I thought would give me a sense of safety and security which in fact, never did. It's a hedonistic treadmill when you're looking for outside things to provide something that's a very internal state. And I guess one of the, sort of, one of the defining moments in my life was ultimately, coming into branding quite by accident. Ultimately, helping grow a company for over two decades that I was ultimately able to sell. And at that point, everybody in my life was like, "Okay, well, you've been talking about "doing all these other things. "Now you have as much safety and security "as you'll ever need." But if it's not an internally driven sense of purpose, it's nothing outside is gonna give you that. And so it took me a whole slew of years after that to finally, finally say, maybe you have to start thinking about if not now, when? If not now, when? And so, I was at the very tail end of making that decision when I was offered the CEO job of the company that I sold to Omnicom, I was offered the CEO at Sterling, Sterling. Sterling Brands, the company that'll always be close to my heart. I was offered the CEO position and thought, "Well, maybe I should take that. "You know, it's a big job and I'm a woman." and, you know, "take it for the team." Powerful and fancy and. Maybe I should do that, maybe this is what I'm supposed to be doing, maybe this is the thing that I'm supposed to just do. It took me four months to decide. My, the then CEO, Simon Williams, my partner, who is the founding partner of the company, said to me, "Debbie, if anything takes you four months to decide, "you probably don't want to do it." Good advice. Yeah. And so finally, after 22 years, I left and on November 1st was my first day of non-employment at Sterling. And since then, so, what has that been, three month, not even, I'm figuring out a whole new chapter in my life and doing all of these interesting things that I never expected to even be doing. So, you know, one of the things that I've always, I've realized now that I've contended with is, living my life from a point of view of scarcity. So not only am I searching for security, but I'm also thinking that any opportunity that I'm being presented with is my last chance for doing that. Last chance for love, last chance for success, last chance for actualization, whatever it is. And what I never anticipated was, I thought, "Well, if I stop doing this, "this will be all I have left." Never thinking, "Well, if you stop doing this, "other things could happen." You know, you're not living in a cave. And so it's been an interesting period of my life now to start to think about options. Help the folks at home understand how someone with your level of aptitude, of sophistication, success on every external measure, can have the dialog that you just shared with us about needing external validation and about worthiness and, this has been the biggest struggle for me and the biggest path of self discovery in my adult life, and I feel like this is my opportunity to learn from you and probably the folks at home, like. Can you talk to me about some of those key levers that created that so that people can realize that they're in that? Because you have to realize that problem before you can fix it. Oh yeah, I think you have to realize this. And I'm not even gonna say that it's a problem. I was gonna say, if I could take any word back right there, it'd be problem. This characteristic or the mindset. It's just the human condition, it's the human condition. And I have become a lot more comfortable with that condition after conducting all the interviews I've conducted with creative people. And the first hint of this came when I was putting my first book together, which is, the world's worst title, it's called How to Think like a Great Graphic Designer. It was the first book opportunity I was offered. I was offered this book by the publisher with the title. And I was so worried that if I said, "I can't write a book about how "great designers are supposed to think. "Everybody thinks differently." And I thought, "Oh, if I say no, "I might never get another book deal." And so I went back to them and I said, "How about if I interview designers "and reveal how they think and everybody "might have a different point of view, "but then you have this wonderful opportunity to, sort of, "get into the heads of different people." And what I very quickly found, was the greatest people that I was interviewing. Milton Glaser, Massimo Vignelli, Stefan Sagmeister, Paula Scher, Michael Bierut, I interviewed, I think 21 designers for this book. Incredible, incredible posse there. All but two, revealed over the course of the interview, that they suffered from, in some cases, debilitating issues of worthiness, to just regular episodes of feeling unworthy. Every single person I spoke to had this condition except for two. Massimo and Milton. When I interviewed both Massimo and Milton, they were in their 80s. I think by the time you're in your 80s, it's like, "Okay, the gig is up. "This is who I am." I gotta figure it out. And just, this is, just take it or leave it basically. Everybody else So insightful. The greatest of the great. And subsequently, since then, I've interviewed close to 300 people on Design Matters and it's not a show about design anymore, about designers. It's about how people design their lives. How does a creative person create the arc of a life. What is their trajectory? How do you make the decisions to do what you do? And everyone struggles with this. Isn't it weird? It's like, if you could just pull back the blanket and say, "Hey, can we just get this stuff out in the open?" You know Brene Brown? Yes. Yeah, Brene, so she's a friend and has done more for me, and I think for, sort of pop culture, and specifically she has a primarily women audience but more men than I know, but in the past year have been sort of effected by her work, which is, if you don't, aren't familiar with her work, it's about vulnerability And shame. And shame. And the concept that we have to hide and protect and pretend all those things because we think it will show strength when in reality that is our biggest gift to the world and that's when you give that, that's what you get those things that are missing in your life. When she came out with that TED Talk, my head exploded. And that was, what, 2009? I think Something like that. Something like that. And one of the top 10 TED Talks of all time. So, it's been seven or eight years since then. I show that podcast on the first day of classes with my undergrads. I've been doing that since it came out. So I have seen it now, like, maybe 16, maybe more because I've watched it on my own as well. I feel like I know it by heart and every time I watch it, she astounds me. Every time I watch it, when I think I know it by heart, she says something that, "Wait, I didn't hear that the last 15 times." So much courage. But the notion that to be able to live wholeheartedly you have to be willing to risk your heart is something that it's taken me my whole life to figure out. And so that's why, you know, when you ask me the question, it's like, I feel like I'm still doing that. I love the answer, it's beautiful. It really is and the fact that there is no finish line to this game, like that, to me that's a great way to think of underscoring what you just said and I know, Tim and I, sorry, Tim Ferriss, we were just spending some time with Tim, he's across the hall, we're at Creative Live, love that guy, you know, we went to dinner last night. And that's what we and I talk about stuff like that. Like, there's no finish line and it's so weird to, especially in Tim's case and in your case, representing aspirations for, you know, millions of people around the world and if they only knew that at dinner, we're talking about how, trying to figure it out. Yeah, well I think part of what we have to contend with now is what I call, living in a 140 character culture. And we are able to communicate with such speed and immediacy that it becomes really difficult to see how a career or an aspiration needs to take time. And I say it all the time now, anything worthwhile takes a long time. And inasmuch as I can look back on my life with hindsight and say, "My 20s were really "a decade of experiments and rejection and failure." I wouldn't change that now because I feel that that helped prepare me for the immense gratitude that I have for what I have been able to do now three decades later. And the longer it takes, I think, the longer it lasts. And I would hate to think that if I had really made it big in my 20s that I'd have had to of sustained it all these years. I don't think I could have. I wouldn't have had the mental tenacity to be able to know what it would take. In the same way that I would've gotten killed at Vanity Fair. The universe has a way of providing for it, doesn't it? Can you imagine? Can you imagine? I think back on my bow blouses and think, "I would've gotten killed. I would've. Thank goodness I didn't get that job. And at the time I was, you know, just. Shattered? Crestfallen. Devastated, inconsolable. The universe has a way of providing. You mentioned so many things that I want to touch on in just that sort of, first introductory (mumbles) there. You mention books, you mention Design Matters, you mention Sterling, you mention like, what an amazing career, but let's, like if we can tuck into that little bit. First book is How to Think How to Think like a Great Graphic Designer. Pulitzer Prize winning title, not. But it's still my best selling book, so there was something about. There was some wisdom in there. Yeah, yeah. But, five other ones, also? Six total? Six total, but they're really different kinds of books. So, I have two books of interviews that are really very much, based on the kind of work that I do with Design Matters, so they're very in depth, long form, intimate portraits of the way people think. And design their life. And design their lives, yeah. Yeah, I love that. Then I have two books that are sort of textbooks. One is called Brand Bible and that's a book that I did with my first year of graduate students when I started the graduate program at the School of Visual Arts in Branding, I had an opportunity from a wonderful woman named Emily Potts who was then working as the acquisitions editor at Rockport. She offered me this opportunity to do a book with my students and that's called Brand Bible and it's a book about how to create and sustain brands. And then another textbook is called Essential Principles of Graphic Design and it's really funny to see these, sort of, textbooks in different languages and different parts of the world. I get images all the time from people that have the Japanese version or the Russian version. And then I have two books that I've done of illustrated essays and that's really, my personal work. The first is called Look Both Ways: Illustrated Essays on the Intersection of Life and Design and the most recent is called Self Portrait as Your Traitor. And that one is probably the darkest of the six. It's my most recent. My next question was, can we talk about that? Sure. Yeah, so you, yourself called it dark, not my word, yours. It is dark. Why is it dark? What does it represent and why should we care? Well, I don't know that anybody should care, but if they care to care, it's... It's a very intimate look at the construction and deconstruction of intimate relationships. And not just significant other type relationships. It's how do you have relationship with a family member or how do you have a relationship with somebody who's cruel or abusive to you? And so, it's a story that's told through visual essays that are all made by hand. This is a book that I did that other than the folios and the copyright information is completely made by hand. And then it was then photographed by a wonderful photographer named Brent Taylor. Who did the Hollywood Issue: New York for us. So, he and I have done quite a lot of work together. And it's made with materials, it's made with lucite, with adhesive letters, with felt and then a lot of drawing as well. And it's told through vignettes. Some of which were in the first person, some of which aren't but all sort of take you through the arc of the deconstruction of relationships. Is it all autobiographical? Yes. Did you find a lot of power in creating something like that? Did you feel like you shared something that you needed to and do you feel like that's a mechanism to get powerful art out in the world or what was the impetus behind creating it? The impetus to creating the work was really just self expression and the incredible gift that I was given after I published Look Both Ways. So, Look Both Ways was the result of a class that I took with Milton Glaser back in 2005 and in that class, he asked the designers that were in the class to construct a vision for what the perfect day in their life could be five years now, from then. So, would've been for me, 2010. Wow, what a question. Yeah, and This is a design class? This is a design class. And so he had us, and ordinarily, if he were still teaching the class, I wouldn't be allowed to talk about this. There was like this fight club pact that nobody was allowed to talk about what you did in the class, but Milton's sadly, has stopped teaching this class. He did it, for I think, 40 years. He said it was the most important thing he did and now I understand why. Because of the influence that that specific essay has on people's lives. I remember you told me about this essay recently when we had dinner. It was like, something I walked away going, "Wow, like the most important thing?" One of the most important guys in design has ever done is this class? Yeah, the guy that did the I heart New York logo is saying that the most important thing he's done is teach. Wow, beautiful. So, he asked us to take a leap of faith and create this vision for what our lives could be. And I put my whole heart into doing this essay, mostly because it gave me permission to fantasize. What he was really doing, and I didn't realize it at the time, was he was giving permission to everybody that was doing this to declare what they wanted. Declare what you want. Make it concrete. And I spent a lot of time, I wrote it in my journal, it was like eight or nine pages of handwritten, and I had, then I made a list of everything that I put in the essay so that I have it really organized, cause I love organization. And one of them was to do a book of illustrated essays. I hadn't done any illustrated work at all in that point in my life for over 10 years. And in an effort to try to make it happen, I sent a letter to a woman named Megan Patrick, who was then the acquisitions editor at F and W Media. And I created an essay. I wrote, I designed it, photographed it, sent it to Megan. Never heard anything. And then I thought, "You know, she didn't say no." "Maybe I should just Ping her "and get a sort of, final answer." And I wrote her and I said, "Hey Megan, I sent you this thing five, six weeks ago. "Did you get it?" She wrote me back instantly, "No, I never got it. "I don't know what you're talking about." Maybe it was because it was too big, I don't know. Maybe it went to a spam box. I sent it again, she got it. She said, "It's a really interesting idea. "It's not really in our wheelhouse of books, "but I'm going to present it to the editorial board "and you never know." She did, she got back to me, they accepted it. I remember I wrote her back and said, "It's a miracle." And she wrote back, "Yes, Debbie, it really is." And so that was my first book, now, of illustrated essays. What happened was because I had been so rusty doing that kind of work, over the course of producing the work for the book, I got better just like you would as an athlete. You know, you start doing pushups by the time. You know, you do one and then you could do a hundred, but it takes time. And I started getting better and more comfortable and looser with the work. To a point where, F and W ended up having to cut me off cause I kept redoing the essays, like I, I just wanted to do one over. Just one, just one more. One more, and they're no. That's it, done And no need to be perfect. Just one more. And I wanted to keep my chops, and so I asked them if I could do an online visual essay every month on Prints' website, because I was already doing my magazine column and they said, "Sure, if you want to." And so that's what I did. And then, Gary Lynch, the publisher, after I'd done about three year's worth, so over 30, wrote me and said, "Maybe we should make this into another book." And that's how the other book came about. It was hard putting it all together and realizing that I was revealing a lot about myself but not everybody knew that it was, people could assume if they wanted, and the most intimate essay was really hard to read. (laughs) I can imagine. So, what I did was, you'll love this cause it's a photography story. I did, I think, 10 or 11 panels of adhesive mailbox type Okay. And I wrote the story on these lucite panels. And we photographed the panels one on top of the other on top of the other. So the whole thing builds and then you see the first one, you can read the first one perfectly, the second one, you sort of see the blurring of the type coming through the way Brent lit it was that it sort of lit from behind. And then by the time you got to the end, all 11 panels were behind the first panel. So, it was a real challenge. You had to really want to read it if you wanted to read it. And I've only had a couple of people say, "Is that autobiographical?" Cause I didn't use my name. And I'm like, "Yeah, yeah, yeah." Wow, so there are so many things embedded in what you just said. Not hearing no, assuming that it meant no, and then catching yourself? Wait a minute, I didn't hear a no. I didn't hear a no. Even when I hear, you know the one thing, I'm super sensitive and have taken rejections really hard to a point where if I get rejected, I won't try that specific thing again. But what I find is that it takes me awhile, and I sort of regroup. I mean, it might take a decade and I'll regroup, but I tend to then, sort of, come around from a different direction to try to, sort of, make it happen, but I also, when I'm told no outright, I tend to push a little bit. "Would you reconsider, maybe? "How about this, what about this way?" But just you sharing that, is so powerful that one of the world's top thinkers and doers in design has that mentality, both the one that fears and feels rejection. And then the one that, wait a minute, there's this sort of a real (mumbles) wait, either I didn't hear no or I heard sort of no, or I'm going to push, like there's a dialog. Regardless, even the content is like, it's almost as important, but that you, Debbie Millman have that dialog, that's like, I want the world to know that because that will help you at home push through that thing. Thank you very much for sharing that. Oh, my pleasure, anytime. So, books. Now let's go to the podcast. Design Matters. Incredible, like one of the top podcasts of Yes. Millions of downloads. That was amazing. The most incredible guests. And you, I think you told me that you get to do this from your office At SVA At the School of Visual Arts? Well, I started doing it at my office at Sterling because I started doing the podcast in 2005. I'm about to have my 12th anniversary of the show. Nice. Stamina people, stamina. Yeah, I have both it's both a good quality and a bad quality. I can sometimes stay in things for too long, just because I'm so dogged about trying to make it right. But mostly that's been, mostly that's been a really positive thing. But I was cold called one day about doing a radio, an internet radio show on a network called Voice America and I had been writing for Speak Up and a piece that I had written with Mark Kingsley, sort of, went a little bit viral the first time that ever had happened to me. And I was cold called by this radio network and they wanted me to do a show about branding. Which made sense, you know, I was president of a brand consultancy. But I didn't want to do that because my whole life, was at that point, about branding. And I wanted to do something that had no commercial value. Zero commercial value. I wanted to do something pure and full of soul. And so I said to them, "Well, I'll do some branding, "but can I also really focus it on design?" And they were like, "Okay." And I thought they were going to be paying me to do the show, but I had to pay them for the airtime. And the airtime was sort of like having a show produced by the producers of Wayne's World. Wayne and Garth were the producers of my show. And it sounds like that. But I moved over to I moved the show over to Design Observer. I was invited by the late great Bill Drenttel. Asked me if I wanted to bring it to Design Observer, with the proviso that I had to improve the sound quality. Quality, yeah, you gotta, that's one thing. It doesn't have to be perfect, but you have to be able to hear what the person is saying. Wayne and Garth probably didn't have that mastered. So, you brought that inside of Design Observer, which is incredible (mumbles) Well, Design Observer started to distribute the show on their site. At the time I was building this new program at the School of Visual Arts with Steven Heller, the great design critic and educator and the former art director of the New York Times for 30 years. He had offered me this opportunity to create a Masters in Branding program at the School of Visual Arts. And I'd known through Alice Twemlow, who had a program that she had started in design criticism that they had a little podcast booth in their studio. So I went to the president of SVA, David Rhodes, incredible man named David Rhodes and I said, "Any chance I could have a podcast studio, too?" "I could end up doing my podcast in front of the students." And I didn't get a little closet, I got a studio. He really made me a beautiful studio. There's a great picture of you with your feet up on the desk. In the studio. I love that shot of you. Yes, John Madier, he did a great job I love that shot of you. With that photograph and that's when I started doing the show at the School of Visual Arts. So, the way that the studio is situated is I have a soundproof booth, but there's a big window and the sound is broadcast outside of the booth, and so all of my students, both grad and undergrad, get to watch me do the interview. Sort of like Inside the Actors Studio. Yes, that's exactly what it's like. And the students, you know, some of the students have gotten jobs from people that have come through to do an episode of Design Matters. But this show was an accidental thing. You know, I got a cold call and at the time I was sort of feeling like my soul was being overrun with fast moving consumer goods and everything that you could get in a supermarket or a drugstore and just felt like I needed to be able to keep that part of myself alive. And it's turned into the greatest gift of my life. And a gift for so many people. It's a very, very powerful to have you in your ears and saying so many of these things and I want to reflect on the fact that some of your biggest mentors' goals and successes were teaching and here you are teaching. So, there's this, you know the circle of life. You teach about branding, but you also teach about the brand of you. Well, that was my class here. Yes, you did, Which I love doing at Creative Live. Incredible class. I can say with zero hesitation that it is the class that I have watched, that I watched most in and I think you delivered in the third quarter. August 31st. There you go. Really, really? Yes, it is one that I've watched the most and it is the one that I see the most on screens that I walk around here. I think Jill, our VP of marketing said that she watched the entire, I don't know if I'm supposed to say this, but Jill, I'm outing you, she said she watched the entire thing last weekend, I think. Really, oh wow. And it's just I think, the, you know, I don't know what it is. It's this beautiful alchemy that you have of your delivery, so many examples, just great cultural reference and so, just I want to Thank you pat you on the back Thank you and say it's, just yeah. Well, thank you for giving me the opportunity to do it. I really love doing it. It was a really, really transformative experience for me to be with those people and like sort of, working with them and being able to sort of, see in their eyes that they were learning. Well, there's some eight or 10,000 people that have taken the class, so. I like to think that it's working. So when you think about career contributing as a writer, as making Design Matters. Do you see either of those things stopping, changing, waning? What about your career as a mentor, as a teacher? You want to do more of that? Like what's? Well, I still teach undergrads. I was teaching undergrads way before I started the graduate program. I was teaching for Richard Wilde at the School of Visual Arts in his advertising and design program. And then when I got the Masters program, he just assumed I was gonna stop teaching the undergrads. But I felt like, isn't that sort of like, when somebody cuter asks you out, you can't, like it's not right morally? So, I just felt like, "I have to still teach the undergrads." And I also enjoy teaching undergrads because they teach me about what's important to them and so I have loved being able to watch my undergrads then, go out and make a difference in the world. I mean, some of my students, Joe Hollier who created the Light Phone. I mean, he's unbelievable. He's my first student that I had as an undergrad that's been on Design Matters. That's what he's become. Santiago Carrisquilla, he's, I mean these men are amazing. The students, Anna Leatham. I mean, they're, it just, my heart bursts when I think about what I get to be able to witness and observe as my students. The humility with which you approach that. You talking about learning so much from the people that you clearly are giving these amazing, or a huge gift. Well, I'm just helping them find. I mean, this is, what I try to do with these students in my class, and I do this in my graduate class as well. What I find that people in their 20s experience is very similar to what I was experiencing in the early, mid 80s. I came out school thinking, "I'm not smart enough, "I'm not pretty enough, I'm not connected enough, "I have no money, I have nothing enough." Including the safety thing. I was telling myself all of those things. Nobody was saying, "You can't do that, Debbie. "You can't do that, Debbie. "You can't do that, Debbie." I was doing that. I was editing what was possible in my life before I was even considering that it was possible. And I see all of my students, I ask them on the first day of class. What are you afraid of? Mediocrity, not being able to fulfill my potential, regret, they're all, and they're in their 20s. And this is what they're worried about now in their lives. So, I'll spend a semester helping to try to reroute the neural pathways in their brains that make them feel like they have to start curtailing what is possible for them. Just by giving them the tools that they could use to go out and get the job of their dreams. And now, I do the same exercise that Milton did with us. I give them 10 years, though, since they're much younger. I put that kind of pressure on them, right? 10 years, 10 years. Your 10 year remarkable life plan. I was talking with Tim about that on his podcast as well. And I get e-mails now that I've been teaching. I'll be teaching undergrad for about 13 years. So, I get letters From people from people that are like, "Debbie, the essay, everything happened." And I'm like, "Yeah, Milton, like "he knew what he was doing with that thing." It's magic. It's the declaration of what you want. It's once you are able to stand for it. This is what I am declaring, this is what I am standing for, this is what I want. Do you know Elle Luna? Of course, Elle. Oh that's right, she's gonna be a part of the thing tomorrow. Elle Luna. You get what you must have, not what you should have. Absolutely, absolutely. And it's declaring. And then this, deserve thing and it's the confidence thing. Confidence is overrated. I learned this from Dani Shapiro, the great writer. We were talking about confidence. And she was like, "Confidence is really overrated." And I'm like, "What, what?" She's like, "Yeah most confident people, "like overly confident people, kind of obnoxious." I'm like, "Yeah, that's true. "Usually they're compensating." She said, "What's more important "than confidence is courage." And I was like, "Oh my God." Confidence is created from repetitive success at doing something. You know you're gonna get the ball in the basket. You have confidence shooting. I know how to create branded products. When I meet with a client, and talk about how we're going to reposition their brand, I've got confidence. I have all that stuff that I've been doing over and over and over again that's been successful that I can pull out of the suitcase and say, "That's why I believe that I'm right." If you haven't done something before, how could you ever expect to have confidence doing it? Confidence comes after you've done it enough times successfully. So what's more important, especially in your 20s, is courage. Courage to take the first step before you have the success. Secret of life by Dani Shapiro. That is gold. Gold. We also have a mutual friend in Tina Roth Eisenberg. Swiss Miss. Yeah, she's incredible. And we had a conversation once about confidence and she said, "Confidence is about yourself, "but enthusiasm is about other things and other people. "And how much more joyful that is to be enthusiastic." How much weight do you put on, sort of, energy and positivity? You already mentioned, sort of, you know, growth mindset as something that is a thing that you're developing in this phase of your life. It sounds powerful. Talk to me about, like, positivity and growth mindset and how you think about those things and how you might give some advice to some young folks, or younger folks, or old folks? Old folks. Well, when hiring, one of the things that was really wonderful about having had Sterling acquired by Omnicom was Omnicom University. So, Omnicom University was started by a man within Omnicom called Tom Watson, it's now being run by a woman named Janet Riccio. She's a genius. They take the senior execs and they bring them to Babson College, which is the number one entrepreneurial college, probably in the world. Certainly in the country. And a lot of Harvard Business School professors are there as well, teaching. One of the most important things that I learned while taking, I took numerous classes, numerous programs. Was that you hire for attitude and you train the skill. With young people, you know, with people that are entry level or there abouts. Because the notion of being somebody that is curious. Somebody that is open, somebody that is willing to learn is untrainable, it really is. So, Simon Williams, my partner told me something very early on in our tenure together that I've never forgotten and I'll share this because I think this is something really true about the way to consider your attitude. He always asked, he said, "There are two kinds of people in the world. "Generators and drains." Generators are people that come into a room with energy and enthusiasm and passion and curiosity and tend to make the mood more vibrant. The drains are the people that come into the room and there's something always wrong. Temperature's not right, something's missing, something isn't perfect and they bring the energy down. What kind of person are you? If you think you're a drain, you probably are. What's the advice to those people? Like, right now, there are people who just had an "Aha, oh shit," moment. Why are you so afraid to show your enthusiasm? I don't think that people are born miserable. Sometimes it's bad parenting, sometimes it's bad circumstances, but don't let that sabotage your life. You can live with whatever self loathing you might have and not have to inflict it on others. Most people, when they're complaining, are just relieving the tension that they feel about a certain circumstance without realizing that what they're doing is creating an atmosphere of toxin, of toxic. And all you're doing when you complain is relieving your own pain and then you're dumping it onto others. Nobody wants to really be around people like that. That's what that drain is. So ask yourself, why do you need to expend that energy in that way? Why do you need to inflict the pain that you're experiencing and the relief that you get by dumping it out on others? And I think if you look at it from that perspective, it changes your need to do it. You still might feel it, but you don't have to necessarily inflict it. I feel like this is an amazing therapy session. For, I mean, for me sitting here, but in. I feel like that's one of my favorite things about Creative Live is helping other people realize their dreams and career and hobby and life. And there's, you know, we have something like 10 million students and when you get, sort of, that many inputs, you start to see a pattern and the part that you said which resonated so deep with me is people cut themselves off at the knees before they've even started. I know. And that's why I need to teach these classes because I did that. I did that. I spent more than half my life doing that. And if I can help somebody else, avoid that journey in that way and be able to live wholehearted and to be able to consider the possibilities that they could do whatever they want if they want it badly enough and if they're willing to really work hard, then, what else is there? You know, that's why probably Milton said, "This is the most important thing." Because that becomes something that does enrich the world. I'm trying to be sensitive to your time. I could I'm cool, I'm cool. I secretly handcuffed myself to you. So, you're not leaving. We're gonna talk for the next 10 hours. No, I thought that we might spend just a couple minutes before we let you go on the way to your party. Are there some things, just what would you consider a couple of life lessons that we haven't covered? In a one liner fashion, like what's a life lesson that you feel like you told students before, or that you've realized it yourself. Can be something that you say everyday, or I know there's a handful of them. I can feel it inside of you, so. I have so many. Well, for students, or for young people that are looking to sort of, make their way into the world, I will tell them, there's no such thing as being a people person in the great scheme of characteristics. Nobody cares if you're a people person. And when I ask students, "Well, why is the reason someone should hire you?" "Well I'm a real people person, I'm a real hard worker." No, those are table stakes. Those are things that you have to be in order to exist in the world with others. With other people. Right? So, what is the benefit for somebody to hire you? What, people are giving you money to do this thing that you want to do, or that you're trained to do, or that you love. What are you giving them in return? What is the benefit that somebody will receive in hiring you? They're not hiring you for any altruistic purpose. They want a return on that investment. So what is the benefit that you can provide? If you can define what it is that you will bring that no one else can bring quite in the same way, then chances are you will have a competitive edge in an interview. So, that's the first thing. And then for anybody that's feeling stuck and wants to create something on their own, or to create something more than what they're doing at their day job, I say, create something that you self generate. Make something on your own and put it out there. Stefan Zagmeister always says, "Don't create a portfolio for a job. "Create the portfolio you want for the job you want." So you have to make your own work in a lot of cases. And people will be, "Oh, I'm too busy." Well, my other big moment that I will, my other big quote that I say all the time is, "Busy is a decision." If you want to do something really badly, then you don't find the time, you make the time. And this is something I learned from Maria Popova. You have to make the time to do the things that you really want to do. If you say you're too busy, then look at what it is that's keeping you too busy. Are you spending too much time watching Game of Thrones? Are you spending too much time puttering around your house and not really concentrating on what is important to you? Chances are if you're not doing it, it's not a priority. You don't want it badly enough. So be honest with yourself then. You don't want to be telling yourself that you want to be doing something as a way to feel less embarrassment about the fact that you're not doing it. I saw something recently and I'm kicking myself right now. It is so in line with that. I know the thing, I'm just trying to attribute it properly. And I'm, because I can't, I'm just gonna go there. It's basically, the exactly the same you said, "Busy isn't busy. "Busy is a lack of priority." So try substituting the words. When you say I don't have time, just try inserting the words, it's just not a priority. Exactly. So, when your daughter asks you to help with her homework, like, "Oh, sorry honey, I was too busy." "Sorry, honey, it's a lack of priority for me." "It's not a priority." And see how that feels. Exactly. And that's the real shit right there. Cause that's literally what you're saying. Absolutely. I mean, Shondra Rhimes said that in her TED Talk, too about playing with her daughters and how she would be like, "I'm too busy." And then she'd sit down and play with them and she realized that all they wanted was like, five minutes. Just get started, just start it. Oh, the other one that I'll leave you with is a fortune cookie. Hmmm, this is good. A fortune cookie. This is so good, I've kept it taped to my laptop. Avoid compulsively making things worse. Wow. Wow. Right? Wow. And how often do we do that? Things are bad and we just do a pile on of everything that's bad. Let's globalize everything that's bad so we can feel even worse. Sometimes you just feel bad. Let yourself feel bad, and it'll pass. Just like hunger passes or just like anything passes. We're regulation machines. So, avoid compulsively making things worse. I was classic at that. Making things worse. Things are bad, let's just make them worse. Thank you so much. I am so excited for those folks at home who this show is over for you. Right now I am about to spend the next 48 hours with this human. I couldn't be happier. Thank you so much for being on the show. Oh, thank you. My pleasure. We're gonna clip as much of this stuff out as we can and share it. You're welcome to share any of it in your channels and the Print channels Thank you, thank you. and here on Creative Live and my stuff, so. Thank you so much. See you soon. (relaxed music)