In short
Debbie Millman discusses leadership and work through her journey in branding, turning down a CEO role, building a long-running design podcast, and later writing a gardening book; she also addresses AI’s impact on creative education.
Guest backgrounds
Debbie Millman is a branding executive and educator. She worked at Interbrand starting in 1993, became president by 1998, left for Sterling Brands (joined 1995; partner by 1999), and helped sell Sterling to Omnicom in 2008. She teaches at SVA and helped plan SVA’s master’s in branding program. She also hosts the podcast Design Matters (began around 2005; originally on Voice America).
Key claims
Confidence is built through repeated action, not waiting to “feel confident.” AI should be treated responsibly (like an “AI age”); it can help as a research/co-writing tool, but shouldn’t replace creative learning. In job search, candidates must articulate unique value beyond generic strengths.
Notable examples
She turned down an Omnicom CEO offer after vacillating; she cites her internet-radio-to-podcast origin; she describes trauma-driven healing and later professional success; she and wife Roxanne Gay acquired and redesigned The Rumpus (rumpus.net).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOIntroducing Debbie Millman
0:45 to 2:56
Jessica introduces the guest, Debbie Millman, highlighting her achievements and influence.
“I'm Jessica Neal, your host of TruthWorks.”
Debbie's Early Aspirations
2:56 to 3:43
Debbie shares her childhood aspirations of being an artist and her early creative experiences.
“First of all, I was supposed to be an artist.”
Overcoming Childhood Trauma
3:43 to 6:31
Debbie recounts her traumatic experiences during her childhood and their long-term effects.
“When did you know that this was what you were going to focus on, like design and creativity?”
The Impact of Trauma on Life Choices
6:31 to 8:11
Debbie discusses how her trauma influenced her life choices and her journey to healing.
“I mean, I even, I was doing an article for a magazine.”
Finding Professional Success
8:11 to 12:52
Debbie shares her journey to professional success in branding and design, and how it transformed her life.
“I mean, I was always very resilient, which I think is probably genetic more than anything else.”
Turning Down the CEO Role
12:52 to 14:01
Debbie reveals her decision to turn down the CEO position and the context behind it.
“So all the other things that I was doing, the writing, the drawing, the making things, even though I wasn't successful at them, I was still doing them because they were very soul-fulfilling.”
Navigating Rejections and Offers
14:01 to 14:39
Debbie discusses her experiences with rejection and the pivotal moment when she was offered a CEO position.
“Rejection is different than you failing.”
Two Decades at Sterling
14:40 to 18:08
Debbie shares her journey at Sterling, including the company's sale and her decision-making process after 20 years.
“And in 95, when I started, I always knew that the CEO, lovely man named Simon Williams, was interested in eventually selling the company and cashing out, I guess.”
The Trapeze of Career Change
18:09 to 19:39
Debbie reflects on the metaphor of letting go of one's current position to embrace new opportunities.
“One that worked at Celestial Seasonings and another that worked at Gillette.”
The Beginning of the Podcast Journey
19:40 to 22:08
Debbie recounts how she started her podcast journey and the challenges she faced with sound quality.
“And I guess at the time that you started it, it was on radio, right?”
Show all 22 chapters
Transition to the Ted Audio Collective
22:09 to 23:39
Debbie explains her transition to the Ted Audio Collective and the evolution of her podcast over the years.
“And so I've been with the Ted Audio Collective ever since.”
Lessons from Podcast Guests
23:40 to 25:58
Debbie discusses the valuable lessons learned from her podcast guests and the shared insecurities of accomplished individuals.
“So one of the things, and I let you ask this question in a second, Pete, because I keep dominating.”
Advice for Aspiring Professionals
25:59 to 28:00
Debbie provides career advice, focusing on the importance of identifying core benefits and uniqueness in job environments.
“and continue to do it, you will get better.”
Career Advice for Students
28:00 to 30:56
Learn about the importance of understanding personal strengths and unique contributions in career development.
“We have a huge HR community that follows us, but we have designers and product managers that listen as well.”
Acquisition of The Rumpus
30:56 to 33:32
Discover the journey of acquiring a literary magazine and the excitement of a new project.
“And I think that's more of a just getting people to really step back and say, what is it that I do well, right?”
The Joys of Gardening
33:32 to 35:42
Explore the personal joys and challenges of gardening and its impact on well-being.
“And you're getting, you know, I'm guessing a lot of this is digital, but you're getting to do magazine covers.”
Writing and Creativity
35:42 to 38:22
Learn about the interplay between writing and design in the creative process.
“Tomatoes, they're easy and they're plentiful and they're delicious.”
The Impact of AI on Design
38:22 to 42:00
Understand the evolution of design work through technological advancements and the role of AI.
“But maybe it wasn't the gardening one that wasn't in there.”
The Impact of AI on Future Jobs
42:00 to 43:31
Explore concerns about AI's role in the future job market and education.
“But again, hundreds of thousands of other jobs were created and opportunities that we never would have even imagined.”
Imagination vs. Technology
43:31 to 45:26
Discuss the importance of human curiosity and imagination in learning.
“And I know faculty that are assigning creative writing and getting back AI writing.”
If Not Now, When?
45:26 to 45:39
Encouragement to seize opportunities before it's too late.
“Well, we always ask our guests to leave our listeners with a little advice, some inspiration.”
Debbie Millman's Work and Influence
45:39 to 46:42
Debbie shares where to find her work and her contributions to design.
“And so if you have something that you've been hoping to start or hoping to finish or just make a bigger part of your life, I think that's a really important question.”
Transcript
Automatic transcript. May contain errors.0:00Debbie Millman:I'll do it when I feel more confident. Well, then you'll wait forever. If you try to do it and continue to do it, you will get better. And that's when confidence is built.
0:12What would happen if we just told the truth? Welcome to TruthWorks, where we dig into the nitty gritty of leadership and work. And what needs to change. I'm Jessica Neal. And I'm Patti McCord. Our journey together started in HR, but trust us, it's evolved into something wild, honest, and well, a bit rebellious. So throw out the handbook. We're here to redefine rules to work for us, not against us. Let's dive into another episode.
0:50Hi, everyone. I'm Jessica Neal, your host of TruthWorks. And I have my friend back with me, Peter Clark. He is here. Hi, Pete. Hey, everyone. How's it going?
1:01Peter Clarke:Going great. Yeah, second pod. Yeah, thanks for having me. Yeah, second pod as a co-host. All right. I love it. Yeah. I haven't gotten kicked off yet. I know, hopefully. I'll get fired next week. Yeah. If he's not back next week, you guys will know what happened. Okay. Debbie, this is my trial. So, you know, I got to look good. You do got to look good and you do. So you're doing it well. But outside of Pete and how great he is, I have a very special guest here today. I'm so excited actually about this because there's just so, when I was doing research about the guest, there's just so much that I didn't know about this woman that I think everybody needs to know.
1:41And I'm really, really excited to have everybody learn from her. But I'm going to just get into it because let's tell you who she is. I think when you think about creativity and design and identity, she is someone who has just chartered a whole new way for us to think about things. And she is one of the most influential voices, I think, in the design community. She also started a program at my college that I went to, the School of Visual Arts, which she's going to tell you about. I didn't get to meet Debbie because I'm too old. But the opposite. I'm so much older than you. Well, you started the program way after I graduated.
2:26She has written many books. And one of the things that I think our guests are going to be surprised about is she also created one of the first ever podcast. I don't know if it was the first ever, but it was one of them. And I think you started the podcast in 2005, if I'm getting that right. Exactly.
2:44Debbie Millman:Yeah. 2005. Yeah. But welcome. And all these things I'm talking about is this woman, incredible woman named Debbie Millman. So welcome to the show, Debbie. We're so excited to have you. Thank you, Jessica. Thank you, Pete. It's really nice to be here. Okay. So I want to go back in time. First of all, I was supposed to be an artist. That's why I went to the School of Visual Arts. I was going to paint. My dad said I would make no money as a artist. He was kind of right. I tried, but I got very discouraged very early. I was like, this is so hard, especially to be a painter in New York, like really quite hard.
3:25So I love creative people and I don't know, there's just a part of me that gets so much joy and fuel from being creative and using it as outlet. But I want to go back in time to when you realized that you were this person and tell us how everything happened. Which part? Yeah. When did you know that this was what you were going to focus on, like design and creativity?
3:52Debbie Millman:How old were you? Well, since my first memories are of being creative, although I wouldn't have pegged it as creative or termed it that way, it was just making things. I was always making things as a kid. I love to make perfume from rose petals and baby oil, and I like to decorate our windows in the house and have all kinds of construction paper installations on the windows looking out. And I forced my siblings to be in plays that I was writing and songs that I was creating and made elaborate book report covers. I spent more time on the covers than the book reports themselves. I had this really funny one that I still have, which was about John F.
4:36Debbie Millman:Kennedy. And the whole cover is like so elaborate. And it's like a three-page book report. See that cover. I bet it's brilliant. All kinds of lettering that I was doing. What grade did you get?
4:48Peter Clarke:That's the important part. Yeah. Did you get an A on it?
4:50Debbie Millman:I think I got an A with like good work on it. I have to look. I was just looking for an old photograph and came across it. I was like, oh my God, this is so elaborate. And then inside it was so feeble. But it was inside of you since you were very little. Yeah, yeah. I grew up always reading and writing and drawing and making things. I made a magazine with a friend of mine between, I think it was either sixth and seventh grade or seventh and eighth. My neighbor was also named Debbie, and we spent an entire summer making a magazine that we hand wrote and drew. And I think still one of the best magazine titles.
5:30Debbie Millman:I can't imagine why nobody's taken it. Debutante. Well, our names are Debbie. For the two Debbies. That is perfect. Right? Yeah, that is perfect. Yeah, I love that. So then you're growing up, you're creative. And then what happened? I think everything got derailed. having my mother's second marriage, my stepfather was really abusive to the whole family. But particularly to me, the whole family was terrorized by his anger and his volatility and his violence and his mind games. But I was also terrorized by his sexual abuse, which obviously was something I kept to myself because he told me that he would kill my mother and my brother if I told anybody.
6:16Debbie Millman:In 1970, when this was all happening, I didn't even know that anything like that existed in the world and thought I was the only girl in the world that was happening to. So I believed it. Yeah, it wasn't something anybody talked about then. Right. Yeah. I mean, I even, I was doing an article for a magazine. I was writing an article for a magazine called Commercial Article about Brenda Starr. They did an entire issue about Brenda Starr, the comic, and she was somebody that I really loved when I was a kid and read every day. And I read the newspaper every day. We got it delivered to the house, Long Island Newsday, which is where I spent sixth grade to twelfth grade, and was looking through the archives of New York News or Long Island Newsday.
7:03Debbie Millman:It turned into New York Newsday, but it was Long Island Newsday. To find some specific strips that I was looking for and across from Brenda Starr in the newspaper was Dear Ann Landers, the advice column, and came across a piece that I had read actually blaming, blaming the girl who was being a coquette for doing something that might attract a bad uncle or a stepfather. And so that also furthered my shame. I'm so sorry that happened. Yeah. And it's fueled a lot of my work as an adult. That's been something I feel has been very healing. Yeah, right. So then you kind of get derailed and there's all this trauma that's happening.
7:47But then you kind of find your way.
7:51Debbie Millman:I mean, I don't know that I would say that I found my way. It took about, let's see, almost 30 years to really begin to live a life that felt unbound from responding to the trauma in really sort of self-destructive and heartbreaking ways. I mean, I was always very resilient, which I think is probably genetic more than anything else. And I thought very early on to get therapy, which was not something that was done in my family to a great degree. So I am really happy that somehow I felt like that would be helpful to me and did find a therapist that saved my life, which, you know, yay. Thank you.
8:39Debbie Millman:Yeah, thank you. Yeah. And as I said, when something like that happens and it goes on for so long and is so terrifying, I think it does change your brain in quite a significant way. Especially if there's a lot of shame and secrecy and harm, physical harm, in addition to everything else. So I think it just takes a long time to reemerge. And when do you feel like you really started to reemerge? Probably in my 40s, my early 40s. Early to mid 40s. When the podcast kind of started and like... Yeah, but I wouldn't say that it was because of that. I would say that it was getting, really achieving some corporate success.
9:30Debbie Millman:Being able to take care of myself in a way that I was proud of. I was no longer living in a place that was, you know, a tenement. I was making some money and could take better care of myself. And it was the first time that I had ever really achieved any kind of significant professional success. And that helped me realize that more was possible for myself. And that gave me a little bit more courage to try and experiment and do more things. So it was really, I would say, in my early 30s, or not my early, my mid-30s that that began. But I don't think I really started to feel more secure about it all until I was in my early 40s.
10:13Yeah. And so tell us about the success. Tell us about what you were doing and what you were working on. And in the research, you got to do some fantastic things with some fantastic brands. So tell us a little bit about it. Yeah.
10:26Debbie Millman:Well, I guess I could say that my first real success was working in branding. Although I did a couple of design projects earlier on that were memorable for me, but my first real big success came in branding. I started working at Interbrand in 1993, and that was really something that I did as more of a last resort because I hadn't really made it as a designer. Well, I hadn't made it as a writer. I hadn't made it as an artist. I hadn't made it as a designer. I hadn't made it as a project manager in design. And so at that point, I had gotten an opportunity to work in new business development and in a branded consultancy.
11:14Debbie Millman:I hadn't worked in a branded consultancy prior to that. And I think because of my experience working in my dad's pharmacy as a young girl and then in college again, I think that gave me a way to see people shopping sort of in real time, almost ethnographically, and got to speak to people about what they were buying. I also worked at Integral Yoga Health Food Store in my early 20s when I first got to New York. I was a cashier. And so I was watching people buy things, watching people choose things. And it gave me a real sense of the psychological underpinnings about why people choose the things to have in their lives.
12:05Debbie Millman:And so I think that's what gave me a real leg up in pursuing projects that I could procure for the agency that I was representing, Interbrand. I had no idea that I had this talent, but suddenly I had this talent. And anybody that ever works in an agency knows that the person that brings the rain, the rainmaker, is the person that gets showered, no pun intended, or maybe pun intended, with a lot of respect. And not everybody can do it. And I seem to have this sort of nascent ability that revealed itself. And I then pursued that very intensely because it was the first time I'd ever felt success.
12:51Debbie Millman:and it was intoxicating and I just wanted more and more and more of it. So all the other things that I was doing, the writing, the drawing, the making things, even though I wasn't successful at them, I was still doing them because they were very soul-fulfilling. But then I stopped doing all of that because I was so enamored with my own abilities that I just wanted to get better and better and better and do more and more and more. And by 98, I had been named president of the agency. And then by 99, I was a partner and well, not at Interbrand. I left Interbrand after two years and went to Sterling Brands.
13:24Debbie Millman:And that's where everything kind of opened up for me. And doing that for about eight, nine years in the way that I was doing it, I had this foundation of success. And that's when I started to think, oh, maybe I should still pursue some of my other interests because I feel like my creative spirit is disappearing. And that's when I began writing again. And that's when I started the podcast. Uh-huh. And so, I mean, I bet that was intoxicating, you know, kind of, you know, having, you know, all of these, not failures to an extent, but, you know, to your point. There were failures. There were failures.
14:03Rejections. Rejection is different than you failing. You know what I mean? That's true. But from rejection to then being accepted and then growing to leading the firm. That's pretty crazy.
14:22Debbie Millman:I was the president of a division. I didn't run the agency. There was a CEO and I reported to the CEO. I mean, ultimately, I did get the offer to become CEO, but I turned it down. You turned it down? I did. I turned it down. Why? I turned it down. because, well, I had already been working at Sterling at that point for 20 years. I got there in 95. I left in 2016. And in 95, when I started, I always knew that the CEO, lovely man named Simon Williams, was interested in eventually selling the company and cashing out, I guess. And I negotiated when I started to be given an opportunity to participate in the partnership if I achieved certain goals.
15:13Debbie Millman:And then over the years, I did and became a partner. And then in 2008, so 13 years later, we were able to successfully sell the company to Omnicom, which meant that I was sort of back in the interbrand world, which was really interesting and very funny. At that point, we had a five-year earnout. I had already started teaching at SVA. I'd started teaching at SVA in 2006, started planning the master's in branding program in 2007 with the knowledge that that was going to be a nice place for me to segue to once I did leave Sterling, which I anticipated would be shortly after the earn out. Why kill yourself to work so hard if you've made a good amount of money?
15:51Debbie Millman:2008, if you remember the big crash, we sold a business in June, June of 2008. Then the world collapsed. So we weren't even sure there'd be, we got an initial payment, but we had an earn out. We didn't know if we would be able to make any more money. And so at that point, leaving wasn't even remotely on my radar. I did start the grad program and was very able to navigate both a full-time day job and a full-time night job because my program was an evening program. By 2010, the branding world had recovered and we got very lucky because those last years of our earn out were spectacular for us. And then by 2012, I really was thinking about leaving, but then was scared and insecure and didn't know what else I would.
16:36Debbie Millman:I mean, I had this other full-time job, but it didn't feel of the same sort of level of financial compensation and leadership. It was different. And so I stayed and I was also renovating a house. So I was like, go, but you know, it's good to have this big income while I'm renovating a house. And we were to do really well. And then I started to feel like the girl that cried wolf. You know, I kept saying I was going to go, I was going to go, I was going to go. And then I never did. And even my brother was like, you're never leaving. Why are you telling yourself these lies? I was like, no, I am. I just have to get my courage up.
17:18Debbie Millman:I just have to get my courage up. And I was doing a panel discussion with the wonderful, really brilliant woman who at the time was the general manager of Puma, and she had left and started her own business, a retail business. And in the year I asked her how she did it, and she said that she had been really holding on to that trapeze with, you know, a real tight grip and then eventually just had to let it go. And I had this vision of myself with my, like, elbows and knees and feet, like all carved around a trapeze bar and thought that I really needed to consider that leaving wouldn't be anything that was decreasing the opportunities of my life.
18:02Debbie Millman:I just didn't know what those would be, what the new things might be. And I had to have some faith in the possibility that I would manifest things that I wanted. And right when I decided to go, my CEO said, do you want to you want my job I want to I want to segue out and become the chairman and start a different style of living and I was like what and so am I well he knew we we both were we had been there already eight years past this the acquisition and yeah I think and he was also about 10 years older than I was or am and offered me the job and I was really conflicted because it would give me the opportunity to really helm this company that I'd helped grow and loved.
18:47Debbie Millman:It would also mean a lot to me somehow as one of the few female CEOs within Omnicom, as one of like a handful of female CEOs in the branding industry, which when I first started in 92 was like, there were two like corporate design directors in the world that were female. One that worked at Celestial Seasonings and another that worked at Gillette. That was it. And maybe one more at Procter & Gamble. That was it. Yeah, not many. Right. And so I just felt like I owed it to my sisters. And then eventually just said, actually Simon Williams, my partner, after four months of vacillating, he finally said to me, you know, Debbie, if it takes you four months to decide something, maybe you don't want it.
19:35Debbie Millman:And he gave me permission to sort of turn it down. Yeah. Well, tell us a little bit about the podcast. And I guess at the time that you started it, it was on radio, right? It was on internet radio. Yeah. So how did that come about? Tell us the story. I was sitting at my desk. I got past a cold call from a fledgling internet radio network called Voice America, not Voice of America, Voice America. And they were looking for hosts for talk shows. And I got really excited. I thought they were offering me a job. They weren't. They were offering me an opportunity to pay them to produce a show. So it was the ultimate vanity project.
20:20Debbie Millman:But also this was 2004. This was around that time where I was, I want to do more creative things. I don't want my whole life to be about market share and return on investments and profit and loss statements. And this seemed like an interesting thing. It was a lot of money, but not so much money that it felt debilitating. And so I signed on for 13 episodes and then really enjoyed it. I was terrible at it. Those episodes are still out there. Really terrible. Heinous. Don't listen. I'm sure not. But I really, I know they were, they were. But I really enjoyed it. I really enjoyed it. And people seem to enjoy the people that I was talking to.
20:59Debbie Millman:People go, oh, that was such a fun interview. And so I continued to do it. I did it for four years with Voice America. And then the late, great Bill Drentel from Design Observer approached me and asked me if I wanted to bring it to his blog, which was one of the first design blogs. And I said yes, but he gave me a proviso. He said I had to improve the sound quality because it was really dreadful. I had no technological ability, and I'm not an engineer. So it was bad. So he helped me. He hooked me up with a wonderful producer who's still my producer today. So that means we've been working together now for 17 years, Curtis Fox.
21:39Debbie Millman:And he helped me improve the quality and overall everything about the podcast. And I had it exclusively on Design Observer as well as, you know, Apple Podcasts and when Spotify started and all of that. Moved it to those places as well, but that was where it was living. And then Ted asked me to join the Ted Audio Collective. And so I did that, I want to say about, it was before COVID. So, is that seven years ago or so? Yeah, yeah. And so I've been with the Ted Audio Collective ever since. It's my show. It's an independent show, but they help me market it and distribute it and find ads. A lot of episodes.
22:22Yeah, so many episodes. A lot of episodes. One of the longest-running podcasts ever. Yeah. Yeah. And I'm sure, obviously, you didn't know that at the time that you were creating it.
22:33Debbie Millman:No, I had no idea. There wasn't even a podcast section on iTunes at that point. I just was uploading the show as an indie musician so my father could listen to it and not have to listen to it live when he was working. He worked as a retail pharmacist, so he couldn't have—and I don't think he even knew what a laptop was. And he could certainly have an iPod. And so it was just a matter of going on his big honking computer and being able to listen to it when he got home. Because it was only—it was live every week, but then replayed and he was able to. But then I had digital files. And that's how a friend of mine, my friend, Brian G.
23:09Debbie Millman:Gomez-Palacio was like, why don't you just upload them to iTunes as an indie musician? I was like, what a great idea. And then a couple of months later, the iTunes chart started and the iPod section started. And I know I actually think I'm sure the chart started earlier, but they started in a podcast section. And at the time, I think there may be like 100 podcasts, but they still had a chart. And I was in the top 100, which was just, you know, amazing. But there were maybe 100 podcasts. So, you know, being 85 wasn't all that great shape. Hey, listen, I think it's great. So one of the things, and I let you ask this question in a second, Pete, because I keep dominating.
Read the full transcript
23:49But one of the things that I love about podcasting is learning from all the guests. And you've had so many. So can you tell us a little bit about, not favorites, but the ones that you've really learned from that have kind of changed the way you thought about things? There's so many.
24:06Debbie Millman:Well, one thing that I can say is that no matter how accomplished anybody is, they still are concerned about what they're making next and their longevity and their legacy and their purpose. And that is encouraging in that I think people that listen feel less alone about their own worries because, you know, if an Academy Award director, Academy Award winning director or an Emmy winning writer or producer or Pulitzer Prize winner or McCarthy genius, if they feel insecure, then like I'm just in the world with them. And that feels kind of amazing. um i've i've learned that i've learned how important it is to learn as much as i can about whoever i'm talking with so that they feel respected and not as if i'm just asking the same questions that everybody else does and that's really important to me i i always know that i've done enough when a guest will say, where did you find that?
25:19Debbie Millman:And, you know, I had my ways. Yeah. Yeah. But it's really just research. There's no, there's nothing nefarious there. Yeah. And, and I've learned how important it is to do things despite feeling uncomfortable or insecure. And I've learned that confidence doesn't show up. It's just something that you build over time after the successful repetition of any endeavor. That's how you build confidence. It doesn't, you can't wait for it to show up. I'll do it when I feel more confident. Well, then you'll wait forever. But if you do it, if you try to do it and continue to do it, you will get better. And that's when confidence is built.
26:06Debbie Millman:Pete, what do you got?
26:08Peter Clarke:well, nothing now based on the criteria of having a question that, you know, it's such a deep cut that you're like, where did you find that? But I was actually going to, there's probably a podcast where you talk about this, but going back to just the sort of switch to Interbrand, the discovery of sort of the nascent talent that, you know, what I'm always fascinated by people's sort of decision process. And as they walk the path of their career, but what was it that, how'd you end up going to Interbrand, I guess, what was the connection to sort of say, Oh, let me go.
26:37Debbie Millman:Another cold call. Literally another cold call. I was sitting at a job that I was miserable in and got a call from a headhunter. It was like, oh, I have this job. And when I told him my backbite, he's like, oh, I don't know if you'd be the right fit, but let's see. Let me pass your resume to them, but don't get your hopes up. And then he called back and he's like, oh, they'd like to meet you. And then they met me and then they liked me and hired me. And I remember skipping down the street after the interview. I'm going to be a vice president. I'm going to be a
27:06Peter Clarke:vice president career was born oh man fantastic did you ever did you ever ask him to that point if your resume wasn't right or whatever and then you know did you ever ask what it was they saw
27:17Debbie Millman:initially to want to have a conversation no i think i think that they probably saw how eager i was to to leave the job i was in no i don't i would never have done that i wouldn't have wanted to burn any bridges, but I think that they probably saw an exuberance about the topic because I was really excited about, I mean, these were brands that they had, that they were working on that I sold in my dad's store. And so I think that my genuine passion for branding, which I didn't even know existed, was revealed in that moment to all of us. And I think that's my guess would be that's what they saw. Yeah.
28:02Yeah. So we have a bunch of leaders, founder. We have a huge HR community that follows us, but we have designers and product managers that listen as well. What is your advice to folks? Is it to find that something that you're eager and passionate about? When you give career advice to the students at SBA and the master's program, what are you talking to them about that is going to help set them off on a different charter than perhaps before?
28:32Debbie Millman:Well, we do a lot of work to identify what their core benefits are. So, you know, people looking for jobs often forget how important it is to be able to provide something that is unique to the environment that they're going into in exchange for the money they're going to get. You know, it's not just about work-life balance at a paycheck. It's about, well, what are you giving to the environment that you're going into? How can you express that beyond I'm a people person or I'm good with type? You know, show me a grid anytime and I'm down. It's way more than that. And so we do extensive work to really understand what are their key attributes?
29:17Debbie Millman:What is the unique benefit that they can provide? And what is the mission that they can share when somebody asks, well, why should I hire you? And we do a lot of work in that regard. Yeah, that's not something that comes naturally to people. I was just watching Reese Witherspoon on like a TikTok the other day. Some woman had called her for career advice and she had asked the woman, well, what are your superpowers? What are your strengths? And the woman couldn't list them. Exactly. Why is that? So I always, because people don't spend the time really thinking about what it is that they can provide.
29:54Debbie Millman:And oftentimes they're thinking about what can I get? And I think in job search, that is a really important thing to consider, obviously. But there is an exchange. There needs to be a return on an investment. And I express that to students, especially creative students. They need to understand the language of finance, branding students especially. They need to understand what is the value proposition here? What can I provide that nobody else can in order to be competitive? You don't get a job, really. You don't go to a supermarket and pick up a job next to the oatmeal. You actually win a job in competition with everybody else.
30:30Debbie Millman:And so what are you doing that is going to best your competition? And thinking that way changes things for them. Yeah, absolutely. Yeah. I mean, Pete and I talk to people about their careers all the day. And I don't know, Pete, I'm sure you see the same thing. yeah but i think yeah it's a lot of the like we just don't take the time to necessarily inventory
30:49Peter Clarke:or also often feel they are unique in that or it's a skill set that is different than someone else right i think we have a tendency i mean there's definitely a percentage of people that have no problem you know confidently expressing their superpowers and then there's 95 of the rest of the world who's like i don't is it a strength right like can i really call it a strength i think we sell ourselves short frequently, right? And I think that's more of a just getting people to really step back and say, what is it that I do well, right? And, you know, can confidently talk about it. I mean, that's a great question that gets asked in interviews too.
31:26Peter Clarke:Like, you know, what would your peers say about you? I don't know. I've never actually stopped to figure out what they might say, you know. I hope they say that.
31:35Debbie Millman:I do a lot of mock interviews with my students in my undergrads to really give them a little bit more of an understanding about what it feels like to be asked those questions and what are the potential best answers that they can provide. Yeah, that's helpful. I don't know, our conversation is so lovely and I don't want, you know, we're running out of time, but I wanted you to talk about the thing that you were mentioning to Pete and I earlier that you're very excited about that you and Roxanne are working on together. And we haven't talked about Roxanne, but you can tell people who she is and tell us what you two are excited about right now.
32:15Debbie Millman:Absolutely. Well, Roxanne Gay is my wife. We've been married for almost six years. And last year we acquired The Rumpus, which is an online literary magazine. And that's where one of the places she got her start as a writer, as did Sherald Strayed. That's where Dear Sugar began. Isaac Fitzgerald, some really wonderful, wonderful writers got their starts there. And she was approached by the then owner last year about the potential of her acquiring it. And it was a dream of mine to do something like this. And she was originally not interested, but I was like, oh, I am, I am, I am. And so we acquired it and we spent the last, I don't know, eight months or so redesigning it.
33:01Debbie Millman:So the redesign is now live. One of my former students who graduated quite a long time ago, Santiago Kereski, I think he graduated like 12 years ago or something. I commissioned him to work on the redesign with us. We work with WordPress and it is truly beautiful. It's right now still a literary magazine, but we're going to be expanding it and I'm going to head up the expansion into arts and culture. So watch this space, the rumpus.net. The rumpus.net. That is so exciting. And you're getting, you know, I'm guessing a lot of this is digital, but you're getting to do magazine covers. Just like your book reports with JFK.
33:41Debbie Millman:I know. I know. I know. It's so interesting. Life is very, right now, my life feels very symmetrical in that regard. Yeah. And I bet it is beautiful. That's how fulfilling. But, okay, so that you're excited about. I think you two also love, when this is your latest book, but you both love gardening. I love gardening. Roxanne loves to taste the things that I make. Okay, so she cooks. She does it. So in my research, I thought you both were like in the garden, but I did read that she cooks, but she doesn't help you in the garden. No, not really. She just enjoys it.
34:18Peter Clarke:Good. Vertically integrated, you know.
34:19Debbie Millman:Yeah, absolutely. And I guess, you know, she's in it in that, you know, she enjoys it and we sit out in the garden a lot together. but I started gardening during COVID. I mean, I've always been a wannabe gardener. It's just hard to be a wannabe gardener in New York City because it's New York City. But I've often had spaces since the early 90s. I always had a little outdoor space. That was always something that I sought, even compromised on location and size of space to accommodate having a little bit of an outdoor space and always tried to have like balcony gardens or container gardens. And they were always really rough and not particularly successful.
35:04Debbie Millman:But that was in New York. During COVID, Roxanne and I now go back and forth between New York and LA because though I'm a native New Yorker, she had a place in Los Angeles that she didn't want to give up. And so we now commute back and forth to both. And during COVID, I was there and had a lot of time on my hands and the weather was beautiful and I wanted to be outdoors as much as possible. And so I started more successful gardening, although it took a while. It took a while. I've become better at it. I am by no means an expert or even in the same stratosphere, in the same universe as somebody like Martha Stewart or anybody like that.
35:39Debbie Millman:And so... Well, none of us are. I just do it for joy. I just do it for joy. Yeah. And then... But your favorite thing to grow.
35:46Peter Clarke:Yeah. Oh, sorry. Go.
35:48Debbie Millman:Tomatoes. Tomatoes, they're easy and they're plentiful and they're delicious. They are delicious. And there's so many varieties. Yeah. Yeah. There's like, I don't even know how many varieties of tomatoes, but there's a lot. What's your favorite tomato? Heirloom. Any kind of heirloom tomato. Love. Yeah. Cherry tomatoes also serve basic, but very poppable. And my cousin actually dehydrates them. And then, so then they're dried tomatoes and oh my God, it's like candy. Yeah. Sun-dried tomatoes are so good. I've learned almost everything about gardening from my cousin Eileen. Okay, good job. And I write about her in the book.
36:22Yeah. Well, tell us about the book because what was the inspiration behind it? And what is it about gardening that's good for the soul?
36:30Debbie Millman:Well, in as much as you might try, you can't control Mother Nature. So any garden that you begin and cultivate and grow is very much out of your control. And so you have to give that up. You have to give up any notion of control. and really collaborate and cooperate with Mother Nature. And that is really incredible to do. Watching things grow is amazing. Taking care of plants and trees and shrubs, fruits, it's just an extraordinary privilege. I think that being able to grow your own sustenance is also just an utter joy and again, another privilege. Everything is much slower. I love getting dirty.
37:21Debbie Millman:I love being outside. I love the feeling of the sun on my back. I love when my dog is nearby and playing in the dirt, in the soil. It's a real gift. The book came quite by accident. I have written, all my books have been about design and branding for the most part. And I got I got an email out of the blue from a publisher at Timber Press, which is part of Hachet. They had seen my documentation of my efforts on Instagram. And I had done some interest for TED when it was online that year about my love letter to gardening. And they were interested in knowing if I'd want to write a book. And I was like, I'm not an expert, so no.
38:04Debbie Millman:But if you want me to do something about my quest, then that would be something I'd love to do. And that's how it happened. And beautiful. And it's a beautiful book. And I think you have seven books, if I'm remembering correctly. I think it's eight. Eight. Eight. Okay. Sorry. I thought it was seven. That's okay. But maybe it wasn't the gardening one that wasn't in there. Do you like writing better or design better? Or do you love them both? I love them in conversation with each other. I love doing both. it's very much an art form that they engage in at the same time that was part of the issue in creating love letter for a garden to a garden my book because my editor incredible woman named mckenna goodman she wanted the manuscript first and i was like no i don't know how to do that like this is this is something that i i write and draw at the same time and then play until i feel like the story has taken its next step.
39:05Debbie Millman:And so for a while I was really stuck because I was sitting in front of, you know, my computer with like three sentences, which were the same three sentences that started the TED interstitial. So they weren't even new. And I didn't know where to go because I couldn't draw and write at the same time. And so then finally McKenna was like, well, why don't you give me a chapter? Give me the first chapter. And so I did. And then she approve that and that's how we built the book. Yeah. Yeah. I would imagine that they go together and they fuel each other. For me, they do. Yeah. Yeah. I draw words. So that's also how it works.
39:43Yeah. I bet your handwriting's beautiful. I'd like to think so. My handwriting's terrible. It's a superpower. Yeah. It's a superpower. It's my superpower. And it keeps getting worse because I don't do it very often, right? Because it's all, you know, on your phone or laptop or whatever. Pete, I'm going to give you the last question. So you better make it good.
40:04Peter Clarke:Well, all right. Oh, pressure. No pressure. Well, I was going to shift to sort of, you know, as we sort of live in the world of technology, Jessica and I, of course, most everything turns to the topic of AI these days. And just thinking back to school, as you're talking to students, I mean, what do you think or how are you talking about the impact of AI, AI tools around just the design industry itself? And sort of, we seem to have this narrative that says AI will do everything better than humans, but I'm just curious, you've got a bunch of students thinking about what am I going to go do and how will this impact me in the future?
40:43Peter Clarke:What are those conversations like?
40:44Debbie Millman:Well, I have an advantage in that I've lived through two technological leaps in my lifetime. The first in the 80s with the introduction of the personal computer and the migration of design work being done from a drafting table to a computer. And at that time, everybody was talking about how we were going to lose all our jobs and computers were going to do all the work of a designer. There were some jobs that were lost, but there were hundreds of thousands of jobs that were created. And so there was a transition, but I don't know that anything was really lost. I think craft is something that is always required within any tool that you're using.
41:39Debbie Millman:And for those that prefer to work with their hands, you still can. Then in the late 1990s, we had the big move to the internet and everybody's business was going to go out of business because it was all going to... Now, Amazon is challenging that. Of course, they do and have put a big dent into the retail business. But again, hundreds of thousands of other jobs were created and opportunities that we never would have even imagined. So this is the third time now I'm hearing about the chance that the entire workforce, as we know it, will be obliterated. Similar to what I was saying before about being afraid to leave my job because I didn't know what was going to come because I could only think of what I was losing as opposed to what I might gain since I haven't gained it yet.
42:26Debbie Millman:I think it's a little bit hard for us to see that far into the future. However, it's a big however, like bold, underlined, however, uppercase. I think that we have to expect that there needs to be a certain level of responsibility in how we engage with AI. I was thinking there should be like there is a drinking age. There should be an AI age. I'm not joking because I think you need to be able to really understand what you're doing. It's a technological lubricant in the same way that alcohol is a social lubricant, but it's not the answer to every question. It can help with providing some stimulus.
43:11Debbie Millman:But for people that are educated, for people that have a certain foundation of an understanding of the world, it could be enormously helpful as a research tool, as a co-writer, etc. But for students who are learning through curiosity, that is what I'm petrified by because I'm already seeing the demise of the student brain. And I know faculty that are assigning creative writing and getting back AI writing. Of course. That's not creative writing. That's not creative writing. Why bother taking a creative writing class if you're just going to get a machine to write something for you? That's not original thinking.
43:53Debbie Millman:And so in as much as I think a lot of you are worried about jobs, I'm worried about brains and the younger brains that aren't formed yet. We wouldn't allow a 10-year-old to drink. We shouldn't let them use AI to learn. Yeah, it's so interesting. I have a six-year-old. And so I was reading an article yesterday. Vinod Khosla was kind of saying like, you know, AI and by I think 2035, he said, will wipe out 80 percent of jobs. And like a five-year-old now won't even have to look for a job when they're older. And, you know. I'm really surprised you said that. I really liked the nude. I'm surprised.
44:32Yeah. I mean, it's scary. It is scary. I don't want that to be true. No, I don't either. He's a big thinker. It doesn't mean he's right. But it is having a child and going through a learning expedition journey in his life. Like, I don't want him to learn through AI. No.
44:52Debbie Millman:I think imagination and curiosity are what make us human. We're the only species that can scenario plan, that can think about the future in the way that we do and can create things the way that we create. And why give that up? Why compromise that? Why dilute that? So I think we're at the very beginnings. And maybe we won't have to worry so much. I don't know. We certainly don't have to worry the way we did about design and technology and the internet and technology, but we'll see. Yeah. Well, we always ask our guests to leave our listeners with a little advice, some inspiration. So no pressure to put on you, but what do you want to leave our listeners with today?
45:38Debbie Millman:Well, something that I've been thinking about a lot as I am now in my 60s and thinking about what I want to do with the rest of my life is a question I seem to be asking myself every day, which is, if not now, when? And so if you have something that you've been hoping to start or hoping to finish or just make a bigger part of your life, I think that's a really important question. If not now, when? When? When? Yeah. When, guys? Listen. Debbie knows. Before the robots. Yeah. Do it before the robots can do it. Yeah. Debbie, if our folks want to find out about you, where should they go to find out about you?
46:23I know you have your website, but is that where they should go?
46:26Debbie Millman:Yeah, debbiemellman.com is my website. That can connect you to the entire archive of Design Matters. If you just want to go there first, it's designmattersmedia.com. and Debbie Millman on Instagram and all the socials. And then you can buy her books where all books are sold and you should get them because they're wonderful. Debbie, thank you so much for being on the show. And thank you for all that you've done in the world and for women too. Thank you. Thank you. Thanks, Jessica. Thanks, Pete. Thanks for listening to TruthWorks.
From the publisher
She built one of the first podcasts in the world.
She turned down the CEO job after twenty years.
And she wants you to ask yourself one question: if not now, when?
In this episode of Truth Works, Jessica Neal and co-host Peter Clarke sit down with Debbie Millman, the founder and host of Design Matters, the longest-running design podcast in the world, now in its twentieth year.
Over two decades, Debbie has interviewed more than 700 of the world's most creative people, written eight books, and shaped some of the biggest consumer brands on the planet, including Burger King, Häagen-Dazs, Star Wars, Tropicana and the No More campaign.
She co-founded the world's first Masters in Branding program at the School of Visual Arts, is President Emeritus of AIGA, and in 2024 was named an Executive Fellow at Harvard Business School.
This conversation goes way deeper than the résumé. Debbie talks about failing as an artist, writer, and designer before stumbling into branding by accident.
She explains why she turned down the CEO offer at Sterling Brands. She shares what hundreds of interviews have taught her about confidence, insecurity, and reinvention. And she gets refreshingly clear-eyed about AI, and what it is quietly doing to the next generation's brains.
TOPICS COVERED
- Failing as an artist, writer and designer before finding branding
- Becoming the rainmaker at Interbrand and Sterling Brands
- Why she turned down the CEO offer after four months of deliberation
- How Design Matters began in 2005 as a paid internet radio show
- What hundreds of interviews taught her about insecurity and legacy
- Career advice for creatives and knowing your value proposition
- Marrying Roxane Gay and acquiring The Rumpus together
- Writing Love Letter to a Garden
- Why AI should have a drinking age
- The one question she now asks herself every day: if not now, when?
What makes this episode hit differently is not the résumé. I
t is the reminder that even the most accomplished people on the planet built their lives the same way the rest of us have to, one brave decision at a time, often with no clue what was coming next.
Debbie's story is proof that reinvention is always available, that confidence is built and never gifted, and that the best chapters of a life can absolutely come after sixty. If you take one thing from this conversation, let it be her question.
Whatever you have been waiting to start, finish, or finally claim as yours, ask yourself honestly: if not now, when?
