Debbie Millman

Debbie Millman is one of the most authoritative, globally respected voices on branding. For two decades, she was president of Sterling Brands, a firm that shaped some of the biggest brands on the planet. At one point, she'd had a hand in around 20% of the brands you'd see on a US grocery aisle. She co founded the world's first graduate programme on branding at the School of Visual Arts in New York. And her TED Talk on branding was watched more than 2.5 million times and named one of the 10 most popular TED talks of 2020. She has built her career on an understanding of how and why brands work. And at the centre of that understanding is the concept of deliberate differentiation. That branding is the act of attaching meaning to an object, idea or movement, and when successful, generates meaningful difference between one box of tissues and the next. Now, ever since Tom Peters' 1997 essay The Brand Called You, we've been told to apply that thinking to ourselves. A wave of books, courses, influencers and consultants on personal branding have followed. And yet Debbie Millman, the expert on branding, says that people are not brands and shouldn't try to be. That building a personal brand is in fact a trap. Which leads to the question, if Debbie built her authority without personal branding, how did she differentiate herself from every other competing expert in her field?

Chapter 1 — Brands

Liam Curley: Debbie's father was a pharmacist. And growing up, Debbie often worked in the pharmacy on weekends and in summers. Working in your father's pharmacy, what do you think you learned about what people buy and why they buy? That would be hard to learn from a textbook or in a classroom?

Debbie Millman: I think that I learned how much kids influence what their parents buy firsthand. You know, seeing a kid bother their parent into, in persuading them to get something that they don't want or need, that the parent doesn't want or need. I saw how hard it was for older people to read packaging, to read the copy, and they'd always ask for help. I saw how much shelf talkers inspire people to try things because I used to make a lot of them and I'd see the full effect of a good design inspire somebody to pick something up. I'd see how hard it was for some people to pay for things. That was heartbreaking, you know, when people would come in and pay for something and with coins.

Liam Curley: What's a shelf talker?

Debbie Millman: A shelf talker is something that you put on the shelf to get somebody's attention.

Liam Curley: Okay, so it could be anything. It's just something to draw the eye.

Debbie Millman: Yeah. And so my dad had an old school pharmacy and his store had old school mahogany shelving. It wasn't typical retail shelving. Like, like there weren't any holes to clip things in. Everything was just neatly stacked behind each other. And so in order for people to be able to know what it was, there was nothing hanging from the ceiling like cookies and bakery or sundries or anything like that. I made the little signs that would identify where things were. Deodorants and shampoo.

Liam Curley: Wow. And you were making them?

Debbie Millman: Yeah, yeah, of course, yeah.

Liam Curley: Cool. Okay, nice.

Debbie Millman: I have pictures of them somewhere. He kept them for a really, really long time because you could see the tape that I had used to put on the shelves was like all yellowed and old looking. But we'll get them anyway.

Liam Curley: Debbie describes brands as her first currency. In her book Look Both Ways, she wrote an essay on her favourite childhood cookie, Fudgetown, and a technique of how she'd eat it slowly and methodically. She was also intrigued by the Fudgetown packaging. On it, an elf holds the package of Fudgetown cookies. It's an example of infinite repetition. I asked Debbie how she thinks this fascination with packaging, specifically Fudgetown packaging, came about.

Debbie Millman: That technique is called the Droste effect. The reason it's called the Droste effect is because it was first seen on this package of Droste cocoa. And I'm showing Liam because we're looking at each other, but you can see the box that this lovely young man is holding. And that is the box that also features a person holding the box. So it's called the Droste effect. And so that's why I have this box here. It fascinated me because there was something so magical about it. And, you know, now I would say it's metaphysical or scientific or, you know, the whole notion of infinity is something that still to this day, all these years later, decades later, still really fascinates me. I spent a lot of time thinking about things like that. And so it's. I love that you asked that question because, yeah, the Fudgetown cookie packaging was as good as the cookies and they don't make them anymore. Apparently there is a Fudgetown brand in Canada and I was able to order some and they tasted terrible. So it was really sad. I didn't know if they tasted the, the way that the cookie tasted back when I was eating them 50 something years ago. And I just didn't realise they were terrible or if they were just not delicious anymore like they used to be. But it was a different manufacturer. So I, I think they either just bought the copyright, the trademark or it had fallen out of trademark and. And they were able to use that name.

Liam Curley: Was there something about the fact that it was on packaging that added some sort of intrigue or was that irrelevant?

Debbie Millman: I think that it was on packaging was significant because brands, in a lot of ways were my first currency. It was what I valued. Lollipops, barrettes, handbags, hand cream. These are the things that I, I thought were special and they made me feel special. And so I would also, for whatever reason, spend a lot of time looking at and reading the packaging, which started, I think, quite normally. I think a lot of people during breakfast, look at the breakfast cereal box or the juice container and read. And that's why there's always so much copy on these containers. And then it just extended to snacks and other modes of containing.

Liam Curley: Debbie would draw the packaging and logos of her favourite products. She liked making things in general, all sorts of things. A trait she picked up from her mother, who was a seamstress and painter.

Debbie Millman: I've always, since I was in middle school, really interested in doing a lot of different things. I didn't have just one area of passion, even when I was in the summer between like sixth and seventh grade. You probably know this because you've done such an extraordinary job of, in researching, you know, I. I made a magazine with my. My neighbour, my best friend, who was also was named Debbie. And we named our magazine Debutante and we wrote all the copy and drew all the pictures and it was a labour of love. But we weren't seeing ourselves as designers or as writers, we didn't even know those terms yet. We were just making a magazine and in many ways we were just making it up as we went along and all of those threads are still very potent in my life.

Liam Curley: Though Debbie knew that she liked making things, she didn't know which craft she wanted to pursue as a profession. In 1979, she goes to the State University of New York in Albany to study English literature with a minor in Russian literature. As soon as she received her first issue of the student paper, she knew she wanted to write for that paper. She approached the editor at the time and volunteered her services as a writer. He asked for clips, meaning examples of her writing. She didn't know what clips meant and so intimidated and shamed, she, in her words, scurried away in embarrassment. She didn't return with any examples of writing and though she fantasised about working for the paper, doesn't find the courage to return to the newsroom until early in her third year at college. There's a women's uprising happening at one of the student health food stores and the paper asks Debbie to cover it. She does, then continues writing for them. And by the end of her second semester in that third year, she's offered the job as editor of the arts and features section. Throughout senior year in college, she was responsible for the layout, the design and the actual paste up of the newspaper. Paste up is the method of physically cutting and pasting typeset columns of text and graphics so it could be sent to the printers and photographed for printing. On designing the newspaper, in an interview with Creative Boom, Debbie says, in her words, she found that to be something truly remarkable, like magical. She loved doing it, and loved doing it as much, if not more, than the editing, writing and assigning stories. When she graduated in 1983, Debbie knew that she wanted to be an artist and or a writer. But there was one thing she knew that she wanted above all of that. She wanted to live in Manhattan. On the Tim Ferriss Show, she told Tim she could have more easily become an artist or writer if she'd lived in Queens rather than Manhattan. But she told herself it was more important to be in Manhattan than it was to do any of those things. I asked Debbie where she thought this fascination with Manhattan came from.

Debbie Millman: I'm a native New Yorker and I was born in Brooklyn. And then when I was 2 years old, my family moved to Howard Beach, Queens. And then the middle of third grade we moved to Staten Island and I lived there until the end of fifth grade. And then my parents got divorced and my dad moved to Manhattan. My mom got remarried and took us to Long Island. And so the two, my mother and her second husband and his kids and my brother and I moved to Long Island. I lived on Long Island from 6th grade to 12th grade and then went to college. Never lived on Long Island again. And when my parents got divorced, I didn't see my father for a long time. But when I did reconnect at that point, I was about 13 or 14 and he had a girlfriend whose name was Betty and Betty lived in Manhattan and my dad did too. And I thought that she was like the chicest, she was like the epitome of a New York career girl and that's all I wanted to be. That was it, you know. And she was one of the really, truly kind adults in my life. I now live on the same block that she lived on, just a few doors down.

Liam Curley: Debbie thought she couldn't live in Manhattan and live the life of an, in inverted commas, true creative. She'd need to do something that would financially support a lifestyle in Manhattan, albeit a modest one. But she didn't really know what to do. She applied to work at Vanity Fair as a writer. Got rejected. In her words, the one marketable skill she had were the tasks she learned at the college newspaper. So she got a job in the design department of a cable magazine, earning $6 an hour. But she didn't really feel qualified to do the work and living in the neighbourhood of a very good journalism school at Columbia, decided to apply to study a master's degree in journalism there. Got rejected. Something else to mention, Debbie paints and had been accepted into a show at Long Island University. She received some good reviews, but like the magazine design, didn't feel qualified enough to pursue it as a career. So she applied to study an advanced degree in art at the Whitney Museum of Art. But once again she got rejected. After a year of working at the cable magazine and the succession of failed attempts to further her studies, she started working in marketing for a real estate developer in Westchester. She was offered the position of director of marketing, received a huge pay rise, $25,000 a year and a car. But she realised after her first day she'd made a terrible mistake. She hated the job. Were you doing marketing for that company?

Debbie Millman: Yeah.

Liam Curley: Was that your first marketing job?

Debbie Millman: Yes.

Liam Curley: How did you come to be working in marketing?

Debbie Millman: This was somebody that I knew through somebody that I had met that was all through connections and they were looking for somebody. They really thought that people that knew how to do design could also do marketing and I actually could. So I was luckily smart enough to be able to run marketing programmes. You know, very modest at the time. In the 1980s, the real estate market was very hot. I mean, that's really when the current US president was coming of age and making his first fortune. And so the New York City real estate, or really the tri State area, but primarily New York real estate, was really, really hot. And there was an agency, there was a real estate firm and quite a lot of designers I think in New York know this. Working with real estate developers, you get to make really beautiful real estate brochures and they usually have nice budgets because they're trying to market really beautiful buildings or homes. And so they were looking for somebody to head up their marketing, to manage the design firms that were designing the brochures, to manage all the advertising. They were doing a lot of New York Times advertising and they were doing a lot of events to open up their properties. And so I ran all of that. And I was all of 25 or something, maybe, maybe younger. But I hated it because I hated, I hated it. I hated real estate. And I had a commute to Westchester, which was really hard. And I didn't have it. I wasn't really working with a collaborative team. There was one other young woman that was there who I really liked and still am connected to on Facebook. But it wasn't a creative job and I felt like I was dying.

Liam Curley: Debbie quits that job after a year.

Debbie Millman: I asked if they would fire me so that I could collect unemployment. And I was really poor. And so I thought, well, if I collect unemployment and I can find some freelance work, maybe I can make ends meet. And I had roommates and was living very hand to mouth. So I ended up getting a few jobs. I worked as a nutritionist for a nutritionist, as her secretary or admin person. And. And I worked at a health food store at night in a health food supermarket. And that was also fun cause I'd spent a lot of time talking to the people about what they were buying. And that was also really great, sort of very foundational ethnographic research. And I started freelancing. And when I was freelancing, I started freelancing for the Rock magazine. And that's when a full time job opened up. And I got it and I took it, making $20,000 a year. And I remember talking to the publisher saying, can I have 21,000 likes just. And he was like, no, take it or leave it. I was like, okay, I'll take it. So I did that. And that was with a whole group of people that I had gone to college with. And that's how I even knew about the opportunity. And a lot of the people that worked on the student newspaper over the years were working there.

Liam Curley: Debbie worked there for a couple of years, worked really well with the creative director there, Cliff Sloan, until they both decide to set up their own creative firm which they called Sloane Millman. Was that all types of design or was it particular type of design work you were doing?

Debbie Millman: It was a lot of entertainment oriented design and institutions. So we did work for the Whitney. We were working with a very big rock and roll promoter in New York, his name is Ron Delsener. And we were working doing all of the promotional advertising for all the rock and roll acts that were coming through. So we did ads for the Rolling Stones and Billy Joel and Madonna and any big act in the late 80s, early 90s we were doing design work for.

Liam Curley: Debbie runs that agency with Cliff Sloan for five years. Towards the latter end of that period she goes through turmoil in her life. She got divorced, moved out of her apartment and turns 30, effectively homeless. She runs her own small business but doesn't feel like she's contributing anything creatively meaningful. She fantasised about working with a prestigious creative firm in New York, doing the kind of work that she dreamed of. One in particular was Frankfurt Balkind.

Debbie Millman: So my cousin at the time was a very high powered executive producer and he had a big job in making movies and his lawyer was a big time lawyer at a big time agency and it was also his good friend and his name was Michael Frankfurt. And so when I was telling Marty, my cousin, that I had this fantasy of going to work at this firm, he's like, Frankfurt, I wonder if Michael's related to the owner. And it turns out that they were brothers. And so Marty asked Michael to ask Steve if he would meet with me and he did.

Liam Curley: Why did you have the fantasy to work with them?

Debbie Millman: Oh, well, because they were among, if not the best design firm working in the late 80s, early 90s. I mean, I would say it was Frankfurt Balkind, M&Co homed by Tibor Kalman, Drenttel Doyle, that's Bill Drenttel and Stephen Doyle, Manhattan Design. There was a handful, just a hand, Coppel and Scher, Paula Scher and her partner, her then business partner, Terry Coppel, Milton Glaser, Seymour Chwast. But Frankfurt Balkind was a bigger agency and they were doing work that was really on the forefront of the technical abilities of the time. And they were using a lot of computers, starting to use a lot of computer work to create their design work. And they had come out with an annual report in 1989 for Time Warner. And at the time annual reports were rather humdrum. They were primarily made for people on Wall Street and the shareholders of stocks and they told a financial story and there wasn't that much to them and they were designed and there was a big design business, there was a big business in for designers that made and designed annual reports. But they weren't really risky or revolutionary because there were financial documents. And that year Time and Warner merged and the annual report that came out was a fluorescent sort of chartreuse coloured cover with a giant, the giant word giant Y, W, H, Y on it. And then right at the very top it said 1989 Time Warner, our annual report. And the world shook, at least the world in New York shook. The New York design world really took notice. And when I saw that, I felt so feeble in comparison. I wasn't trained as a designer. I was working as a designer primarily because I learned how to design my student newspaper when I was at college and took those skills. Those were really the only marketable skills that I had as a designer to get a job. And when I saw that annual report, I thought, I have to figure out how to make things like that. I have to learn how to make things like that. And so there were a handful of firms that I would have given my right arm. I'm a lefty. And M&Co would have been another one. But M&Co was so, both culturally and attitudinally, in my mind, so far out of my league that I wouldn't have even considered being able to get a job there. Whereas Frankfurt Balkind though I felt the work was in many ways more experimental, the work M&Co was doing was more provocative. The work that Frankfurt Balkind was doing was more experimental. And I felt like I needed to learn. I had to learn those skills. And so I was talking to Marty about it. Marty recognised the last name. He talked to his brother, his best friend Steve and his lawyer. And then Steve talked to his brother. And then I got the interview.

Liam Curley: Debbie gets the interview, but it's not with Steve Frankfurt. It's with his business partner, Aubrey Balkind. So he looks at your portfolio, from what I understand, said the design's not good enough, but he offers you a job in marketing.

Debbie Millman: Sales. More sales than marketing.

Liam Curley: Okay, right, great. Because as far as I understand, you hadn't done sales up to that point.

Debbie Millman: Well, when you have your own business, when Cliff and I were running that business, we were doing sales and we were doing everything we had to do everything. I did everything from sales and marketing to dropping things off at FedEx, to licking envelopes, to setting type to. I mean, any. Any and everything. Because when we started, it was just, I think, the two of us and one other additional art director and an admin.

Liam Curley: Why does he offer you the sales role when you came in for design?

Debbie Millman: Because he didn't think I was a good enough designer. But he knew that Steve wanted to hire me, you know, more as a favour to his brother.

Liam Curley: Right.

Debbie Millman: He really likes you. So I'll hire you, but I'm not going to hire you as a designer.

Liam Curley: Debbie works at Frankfurt Balkind for a year until she receives a call from a headhunter. The headhunter is working on behalf of a small design and branding consultancy firm called Sterling Brands that had around 15 employees. She hands in her notice to Aubrey Balkind. So later on, you hand in your notice a year later, Aubrey told you you'd be very good in packaging design. What do you think he saw in you and or your work that led to the conclusion that. That you'd be great in packaging design?

Debbie Millman: Well, at the time, branding was still considered a bit of devil's work. I think he thought that I was so mainstream, so mediocre mainstream, that that would be a kind of good place for me somehow. I mean, he might have meant it more as a compliment, but I don't know. He wasn't. He was only nice to me. I saw him a couple of years later at a Cooper Hewitt National Design Gala, and I was there. And at that point I had already started to make a little bit of a reputation for myself within AIGA. And so I think he knew that I had done maybe a little bit more than he expected. And he was quietly respectful. And so I think I surprised him.

Liam Curley: Debbie moves into her role at Sterling Brands in 1995. Was it a sales role at Sterling that you went straight to?

Debbie Millman: I started in sales, yeah. And it was really primarily a sales role because I was the chief rainmaker for the entire time I was there. But in the first couple of years that I was there, so I got there in 95, and by 97 or so, I had really won a lot of business for them. And the design team was primarily European and were having a really hard time understanding the American vernacular. And so while I was winning a lot of projects, we were also getting fired from a lot of projects. And that was really difficult because I was winning really big good jobs. The redesign of Yoplait and Pancake brand and Tylenol and a smoking cessation brand. Like really big projects with really big budgets, and then we would have trouble delivering. And so then the senior partner, the founder of the firm, promoted me to president and then a year later to partner. And so at that point, I was also able to oversee the work that was being done and delivered to the client.

Liam Curley: Debbie was the rainmaker, pulling in more and more work that required more and more staff. She was phenomenal at selling brand projects. Sterling would become one of the world's largest brand consultancies, employing more than 150 people across five offices. They had double digit growth every year for more than 20 years. In which time Debbie becomes partner and they get purchased in 2008 by Omnicom, one of the largest holding companies in the world. As she puts it when interviewed by Tina Essmaker on The Great Discontent, for the first time in her life, she found her niche. In part, she found that niche by ignoring terrible advice. Speaking with Tim Ferriss, Debbie tells a story of applying for one of those jobs I mentioned earlier at Condé Nast, the publishing firm behind Vogue, the New Yorker and Vanity Fair. When she was a baby designer, she also wanted to write and paint and do all sorts of other things. The HR person at Condé Nast told her, pick one thing and stick with it. Debbie says that's the worst advice anyone ever gave her. Why is that the worst advice?

Debbie Millman: Because I don't think that we're living in a world now where anybody has to do one thing. If anything, the world has changed so much that designers really are kind of required to be polymaths now. The better your array of talents, the better practitioner you are. Designers need to be able to have an understanding of behavioural psychology and cultural anthropology and finance and then all the technical ability that you need. And I think that only makes you a better designer and a better practitioner of anything.

Liam Curley: In the context of building a business around her authority, I think what Debbie has done, and what you're going to discover later in this episode, is she developed a T shaped approach to her learning, certainly before and during this time at Sterling Brands. The concept of T shaped expertise has been around for decades, popularised by Tim Brown of IDEO in the 2000s. IDEO are the design firm that designed the original Apple mouse and also the firm who popularised the concept of design thinking. In an interview on Hello Monday, Brown spoke about the fact that he was this weird kid in the English school system who was interested in engineering and physics and art and history, and the crossing of those boundaries has served him as a designer because he can connect ideas from one field with those in another. David C. Baker talks about this too. You develop expertise in one field and broader knowledge across a range of fields from which, in the context of authority, you can draw inspiration and connect ideas which have not yet been connected. I think Debbie Millman did this and I'll explain more on that later. I see this with many authorities I study. They have deep expertise in one area which addresses a frustration or a task that's really important to a particular group of people. But the interesting angles they find on the subject, the unique lens through which they present a new perspective, often comes as a result of drawing supporting solutions, analogies or principles from other areas that they're highly interested in. It's translating ideas from one field into another. Nancy Duarte did it with presentation design when she introduced storytelling. Rory Sutherland did it by interpreting everyday buying and selling decisions through behavioural science. And Blair Enns did it by introducing pricing theory as it's applied to creative service firms. Obsessively solve a problem worth solving in your field. Introduce new ideas that enlighten your observations from outside it.

Chapter 2 — Speak Up

Liam Curley: If we reverse back to 2003, Debbie is eight years into her time at Sterling Brands. She's president, pulling in work from major clients and in her words, she's almost effortlessly successful. The time as a child obsessed with brands and working in her father's pharmacy had formed her taste and intuition for branding. But she wasn't creatively fulfilled. Remember through childhood and into early adulthood she spent her life making things and wanted a career as a creative. Most of her time at Sterling was managing the business.

Debbie Millman: Not that I helped win the business. I helped determine who would be working on the business, the teams of the business. I would manage the financial well being of the business and would weigh in on what the design should be. But I wasn't doing hands on design. I didn't design the Burger King logo, I didn't design the packaging for Star Wars.

Liam Curley: She was doing some freelance work to keep that creativity going, but it was minimal. Around this time of 2003, Debbie discovers AIGA, the American Institute of Graphic Arts. AIGA is the oldest and largest professional body for designers in the US. Inside the AIGA was a special interest group, the Brand Experience Centre. On the Tim Ferriss Show, Debbie talks about how excited she was by this discovery, that it was the Venn diagram of her life. In her words, she could do branding and they have designers and all these famous designers are on the board and she could meet them and be part of this great community. So she became a member of AIGA, volunteers for the Brand Experience Centre and after a period of working with them, loving the work, she gets appointed to the board. She felt part of something. There's a two year term to sit on the board and Debbie is heavily involved in the day to day. During that time, come the end of the term, each member on the board had to reapply to rejoin the board. Everyone on the board reapplied. Everyone was appointed except Debbie. She was rejected and it felt like all those rejections she'd experienced earlier in her career. She was devastated. Now Ric Grefé, who was AIGA's executive director at the time, he had seen how much Debbie wanted to be part of AIGA and how much she was putting into her role on the board, he felt for her. So as a gesture, he took her to lunch at Eleven Madison, one of the most prestigious restaurants in New York. Over lunch, he asked her not to give up. In his words, as quoted by Debbie, we need people like you. We'll find a place for you, I promise. As something of a consolation prize, he invited Debbie to be a judge on an upcoming annual competition at AIGA called 360. Debbie would serve on the judging panel on the packaging design category. At this point, Debbie had worked on a lot of big brands. She just recently worked on the Burger King logo redesign and the Star Wars Attack of the Clones merchandising. The winning brands would feature in an article to be published in the annual AIGA journal. Ric asked for Debbie's credentials to be presented in the journal, so she sent examples from her recent work at Sterling. Following the publication of the article, Debbie receives an email from a friend with a link suggesting she read the article in the privacy of her own home with a big drink. She clicks the link and lands on an open letter to AIGA written by a designer called Felix Sockwell on a website called Speak Up. It's one of the first blogs on design. The letter is titled AIGA Sellout. It absolutely tears down AIGA for including Debbie on the panel as a judge on their annual competition, accusing her of being a corporate clown and labelling her a she devil. The comments that follow from other designers are just as harsh and continue coming in for days. Debbie was ashamed and terrified that people at Sterling would see the article and the subsequent reputation of the firm would suffer, that this high point in her career would disappear. More articles criticising Debbie followed. The next was titled Is the Dark Side Prevailing? Debbie couldn't stop herself from refreshing the site multiple times daily to check the latest article or comment that had been written about her. But then there was the most unexpected turn of events. A few weeks later, a 23 year old named Armin Vit reached out to her. He's the founder of Speak Up. After the tear downs on Speak Up, the founder apologises for the nature of the criticism, although it sounded like not the criticism itself.

Debbie Millman: For the style that the criticism was communicated, but not the communication, not the criticism itself.

Liam Curley: Right, yeah. And then somewhere in there he asks you to write for the site. Do you have a sense of what, how that comes about, like why he does that?

Debbie Millman: Oh, well, when he apologised, I was so thrilled to hear from him and get that apology. I mean, I was still smarting from all of that tear down. And it really wasn't just the one piece that they were that the one sort of famous piece wherein I was called the she Devil and a Corporate Clown. There were other articles after that. There was another one. The title was, Is the Dark Side Prevailing? You know, as if I was Darth Vader. And so I was really humiliated by all of that. But then, as I said one day, out of the blue, Armin wrote me and apologised. And I guess I was feeling rather magnanimous over the fact that he was actually apologising. And so I said, you know, this is a really interesting forum you have. It was. I mean, here was this group of designers, both young and well established, both unknown and well known, all communicating in real time around a design idea. And I thought it was amazing. And I said that to him and he then said, well, would you like to write for the site? And I was like, hell, yeah.

Liam Curley: As Debbie started writing for Speak Up, she realised she'd found what she'd been looking for all along. A group of misfits. To quote Debbie, trying to change the world through graphic design criticism and online conversations. Autumn 2003, a matter of months after the first teardown, Debbie flies to an AIGA annual conference in Vancouver with Speak Up. They're handing out a booklet, a self published collection of the best writing from the blog's first year, titled Stop Being Sheep. On that flight, Debbie starts speaking with the woman sitting next to her. Her name is Joyce. Joyce tells Debbie she's a writer at Print magazine. Founded in 1940, Print is one of the oldest and most respected design magazines in the world. Winner of multiple magazine awards. Debbie tells her about her work at Speak Up, which Joyce is really interested about. They talk for a couple of hours on the plane. Joyce gives Debbie her business card, which Debbie puts straight in her bag. And it's only when she gets to a hotel room in Vancouver that she looks at the card and discovers that Joyce is editor in chief at Print. Debbie invites Joyce to come to the get together Speak Up are having. And Joyce comes. Debbie harboured dreams of writing for Print. One day, Joyce is organising a live competition for the How Design Conference in San Diego and she wants Debbie to take part. It's a riff on a popular reality TV show at the time called Iron Chef. Three designers make work live on stage and the audience votes for a winner. Debbie hated the idea, but feared saying no would close the door on Joyce for good. So she says yes, has to dress up on stage in a chef's outfit, but she comes second out of three. So not so bad. Incidentally, the judge that day was Steven Heller, one of the most respected design critics in the US, art director of the New York Times Book Review for nearly 30 years and author of well over 100 books. I'm not going to go too deep on that relationship in this episode. But Debbie would ultimately co found the masters in branding with Steven. Not long after meeting, he would also introduce Debbie to her first book opportunity. It's an opportunity he turns down and recommends Debbie. The publisher offers the book and title How to Think Like a Great Graphic Designer. Debbie felt intimidated by the task, that she wasn't qualified on how to write about how great designers think. But fearing she might never get another book deal, she suggests to the publisher that she interview great designers and reveal how they all think. The publisher agrees and that's the book she writes. Simultaneously to writing that book, and a few months after the Iron Chef event, Joyce Rutter Kaye, the editor of Print magazine, reaches out to Debbie to ask if she would write a review about Wally Olins' upcoming book on branding. Debbie does. She writes her first piece for Print and then continued to write in every issue since. One thing to highlight here. I've spoken in previous episodes about getting lucky and fat tailed events. Every authority becomes an authority in part through a lucky break or several lucky breaks, what Nassim Taleb calls fat tailed events. The game is to increase your surface area of luck. Much of that is done by honing a craft which takes years or decades. It's the craft of solving a meaningful frustration or task as experienced by a particular group of people, as I mentioned earlier. And it's subsequently the art of developing and sharing insights around that craft. But there's another piece too. It's the act of placing yourself in as many often uncomfortable situations as possible so that you might chance upon that lucky break. Debbie's career is peppered with examples of putting herself out there. And I'm only sharing the moments that led to the moments of luck. We've got the rejection of the college newspaper, which she'd later reapply to, the rejection of AIGA, which she'd later judge for, writing for Speak Up after all those personal teardowns, flying to an event with Speak Up where she meets Joyce at Print, inviting Joyce to a Speak Up get together, going on stage as a chef, asking Steven Heller for lunch, taking on the book deal, though she didn't feel qualified. She got lucky breaks. And we'll get more that I'll discuss in Chapter three, because she was constantly putting herself in positions to get lucky. In November 2004, days after the US election, Debbie and a fellow Speak Up writer, Mark Kingsley, pulled together a piece on all the election graphics flooding everyone's inboxes. This article went viral. It was picked up across the design blogs and the comments section ran for days. And it caught the attention of a small Internet radio network.

Chapter 3 — Design Matters

Liam Curley: Shortly after that viral piece came out, a small Internet radio network called Voice America approached Debbie asking if she'd be interested in doing a show about branding on their business network. Debbie was excited, said yes, and then realised they were actually offering the opportunity for her to pay them to produce a radio show on their network. Before writing for Speak Up, Debbie had, in her words, all but stopped doing her personal creative work. She'd stopped journaling, stopped writing poetry, stopped playing guitar, and stopped all the craft projects she'd done when she was younger. She told Brené Brown on Brené's podcast, in her words, that at that point she had eight or nine years of corporate success, and as she said, she had become really addicted to it and gave everything else up. And she started to feel about eight or nine years in that she was losing her creative spirit and maybe her creative soul was gone. Now she was writing for Speak Up and Print magazine, rediscovering sparks of that creativity. But she wanted more, and this radio show provided an opportunity to do more. So she paid Voice America to produce 13 episodes. I asked Debbie, if you were looking to rediscover a creative outlet, why radio show? Why not pick up the guitar you put under the bed or get back to journaling?

Debbie Millman: Because nobody came knocking asking me to do it. This was the ultimate vanity project. I had no idea what I was doing. I had no skill in doing what I was doing. I just had this sort of Hail Mary hope that this would give me some sense of. It would reignite some creative spark in me and make me feel like I was doing something that wasn't so commercial, so.

Liam Curley: Cause obviously, you know, you could have started writing poetry journals without someone asking. Was there something about someone asking you that unlocked something or gave you permission?

Debbie Millman: Yes, it was somebody asking me to make something. And so that felt a little bit more legitimate than reopening up a journal and writing terrible poetry.

Liam Curley: Debbie did push back on one thing that the radio network requested. She didn't want to make something on branding. Here she is speaking on Creative Live with Chase Jarvis.

Debbie Millman: 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.

Liam Curley: Debbie had just worked on a redesign for Pepsi that was about to be featured on The Apprentice. So Debbie, for the purpose of convincing the producers, hooked design to branding. She'd interview people like the design director at Pepsi. The network loved the idea. The show would be called Design Matters. Here she is speaking with Jessi Hempel on Hello Monday.

Debbie Millman: It felt like it was something I could sneak under the radar. It could be something creative that I was doing, but also maybe if I was interviewing clients, it could be considered something that was supporting the business. And in fact, it did.

Liam Curley: She'd used the radio show as an opportunity to interview designers she idolised, people like Milton Glaser and Paula Scher. And then she'd interview friends and friends of friends, all of whom worked in the design industry. She'd spend 10 hours researching the subject of the interview for each episode and come with about five pages of questions about their lives. And word about the podcast was spreading among designers because nobody was doing anything like this in the community. But the sound quality was terrible. She and the interviewee would sit across from each other at a desk, speaking and recording on a landline. She compared the production quality to something like Wayne's World.

Wayne's World: Wayne's World. Wayne's World. Party time. Excellent.

Liam Curley: The show went out live. One of the founders at Speak Up, Bryony Gomez-Palacio, contacted Debbie to tell her she was frustrated with the live format. With live radio, a listener had to listen live or tune in in the early hours when a replay was aired. She suggested to Debbie that she take the digital file and upload it to iTunes like an indie musician would. Then Bryony could listen whenever she wanted. So Debbie did. She started uploading Design Matters to the new podcasting feature on iTunes. And in spring of 2005, Design Matters became a podcast, one of the first on Apple. She paid to produce another 13 episodes and continued to air the first 100 on Voice America. Growth up to this point was mostly through word of mouth, until in 2009, she gets an opportunity to expand the reach of the podcast. Bill Drenttel, founder of a popular design blog, Design Observer, asked Debbie if she'd be interested in bringing Design Matters over to Design Observer. Debbie has said Bill Drenttel was the first person to take the show seriously. What does it mean to take the show seriously in that context?

Debbie Millman: He saw I had potential. The late, great Bill Drenttel. Now, just in terms of the wonderful symmetry of this conversation. Bill Drenttel was one of the people that I referenced very early on when I was talking about the hot design time of the late 80s, early 90s in New York City. Bill was one half of Drenttel Doyle. He was Bill Drenttel to Stephen Doyle. Bill was very nice to me even before Design Matters, when I was thinking about trying to make my way into what was considered the New York City design scene, even though I was working in New York City, I was certainly not part of that. In thinking about Frankfurt Balkind and thinking about Tibor Kalman or one of the other agencies that I also thought about was Drenttel Doyle. And so I cold called them one day and Bill answered the phone. Cause people used to answer their own phones back in the day. I once called Massimo Vignelli and he answered the phone and Bill gave me great advice. He gave me great advice. He didn't know that I was the same person all those years later, 20 years later, that had started this rinky dink radio show. But he knew of the show because once I started doing it several years, it did gain some notoriety as this thing that somebody was doing that nobody in the design world had done before. And then podcasts started and it sort of took on a little bit of a life of its own. But at the time I was doing it in like a Wayne's World production. It was so terrible. And Bill was like, look, this is, you know, you have something interesting happening here. Why don't you bring it to Design Observer? But the proviso is you do have to take the sound more seriously and get yourself a producer. Like, how am I going to find a producer? I've never done audio before. This isn't my thing. And he introduced me to Curtis Fox, who was in 2009, who's still my producer to this day.

Liam Curley: What did Design Observer do to promote the show?

Debbie Millman: Well, just having it on the blog really promoted it. At the time there were two main design blogs, Speak Up, which is now Brand New, and Design Observer. That was it. And Armin wasn't posting podcasts. So Bill was really the first person that said, hey, let's put a podcast up on this design blog. And that was my podcast.

Liam Curley: And I've not written this down here, but am I right in thinking that you moved the podcast to Design Observer?

Debbie Millman: Right, yeah, yeah, yeah. No, he invited me to bring it. So I left Voice America and then I went to Design Observer and was on Design Observer exclusively for probably another 10 years or so. And then Design Observer had some changes and then TED came and asked if I would be part of the TED Audio Collective. And so I'm now part of the audio collective. But I still own the brand. I still own Design Matters. They market and advertised, so they, they help me monetize the show so I don't have to do any of that, which is kind of amazing.

Liam Curley: A couple of years later, the show begins to evolve. It's no longer a show about designers talking about design. It's about how creative people design their life. Debbie has had high profile authors on the show like Malcolm Gladwell and Anne Lamott, actors like Claire Danes and Ethan Hawke, and musicians like Jack White and Amanda Palmer. As the show got more popular, Debbie started receiving requests from high profile creatives to feature on the show. For example, the PR firm for the director of Hamilton, Tommy Kail, messaged Debbie on Facebook asking if he could feature on the show. So his publicist reaches out asking to be on the show.

Debbie Millman: But he reached out on Facebook in my Design Matters page.

Liam Curley: So you didn't see it for months, right?

Debbie Millman: Months. I didn't even know that you could be communicating that way. I was looking at the site and I was like, oh, what's that number? And I click in and there's like all these messages from people and then one of them is like, Hamilton, Director. This was 2016, I think the year that Hamilton came out. It was like, oh my God, I started to cry.

Liam Curley: Was that the first time someone like you really respected and had no connection with reached out and asked to be on the show?

Debbie Millman: Probably, yeah.

Liam Curley: Broader fame of the podcast led to a bigger market for the podcast. But important to point out, she would never have got to that broader market if she hadn't first started narrow in her area of authority. The reason she got the early traction that led to bigger platforms was because the podcast was made about design for designers, and designers hang out together. That's why word of mouth kicked in and it wouldn't have if she'd gone broad from day one. So Design Observer gave Debbie a bigger platform than she'd previously had. And subsequently, in 2011, the show gets nominated for a huge award.

Debbie Millman: The show had been nominated in 2011 for the Cooper Hewitt National Design Award, and it was the award where the people vote, the people's choice, which is pretty amazing. I was up against the High Line.

Liam Curley: The High Line was and is an elevated public park built on a disused freight railway above the streets of Manhattan. It was a critically acclaimed landmark of urban design.

Debbie Millman: A podcast against the High Line which is this massive tourist architecture masterpiece. But Bill was like, if you want to win, well, let's do this, let's do this, and, like, let's work hard to win this. And that was certainly the first biggest, because that meant I got invited to the White House. I also went to the award ceremony. I was telling somebody this at the award ceremony two nights ago. I got the award from Pharrell, but in 2011, I had no idea who he was. And I'm like, who's Pharrell?

Liam Curley: How did you get the nomination?

Debbie Millman: I don't know. You can nominate anything.

Liam Curley: As the show expands in popularity and notoriety, Debbie attracts brand partnership deals from companies like Adobe who back her to take the show on the road and interview guests like Seth Godin and Milton Glaser in front of live audiences. And I want to pause here on this detail. This happened with Chris Do and Rory Sutherland from previous episodes. Debbie, Chris and Rory all built their authority as practising authorities, meaning they developed and shared insights on their subject matter expertise and in time became recognised within their field as authorities on branding, design and advertising, respectively. But then their approach evolved. Rory Sutherland captures it beautifully here.

Rory Sutherland: A very clever colleague of mine called Nicole Yershon needed to fund a laboratory in which we experimented with new tech and new ideas. It was kind of the R and D function for Ogilvy, and she couldn't get funding for it. And she said, well, what if instead of giving speeches and talks for free, what if you charge for them and use the money to fund the lab? Which is how it all got started. As a consequence of this, I only realised this about a month ago. This is why intuition is so important, because often you don't know what you're really doing while you're doing it. Now, as a consequence of that, I get invited to speak at things which weren't marketing or advertising conferences. I thought, well, since they're paying to fund this lab, I might as well turn up. As a consequence of that, I didn't do what most advertising people did, which was show a lot of ads. I showed some ads, but I also talked in general because I realised that most of the people at a compliance conference will never be in a position where they have to make an advertisement. So the advertisement isn't that interesting to them, except to the extent that it illustrates a different approach to problem solving, which is psychological rather than, let's say, technological or deterministic in some way. Anyway, as a consequence of that, and I only realised this a month or two ago, what made this different was I wasn't selling what we did, I was selling how we thought. And when you do that, you accidentally discover that the, what you might call the potential market for your wares is 100 times larger than I think the conventional advertising agency has realised.

Liam Curley: A practising authority shares their thinking within the boundaries of how it relates to their market. They give away unapplied thinking for free and it acts as a sample of the thinking that is sold for a higher fee when applied to a client's unique situation. Same concept with the book that they write. That's a practising authority, which Debbie was prior to the success of Design Matters. But as with Chris and Rory, she increased her total addressable market when she started speaking about how she thought, as it applies to a wider market. Debbie does this when she talks about how to live a creative life. She's no longer confining her thinking to the boundaries of branding, she broadens it as it applies to design and then as it applies to designing a creative life. Now her material has mainstream appeal. She's a crossover authority and as such, the nature of the opportunities and business model change. As a crossover authority, brands, sponsors and event organisers pay high sums to work with Debbie because she has such market reach and recognition. But remember, the thinking that led to the crossover popularity is born from the decades of expertise developed and the underlying authority established in her subject matter acted as a platform to crossover notoriety. Let's get back to Design Matters. And in 2015 another moment occurs which triggers further growth.

Debbie Millman: I would say that the first big change came in 2015 when unbeknownst to me, iTunes named it one of the best shows of the year. And I didn't know, somebody saw it and tweeted it to me like I didn't even know. And I remember I was at a restaurant and somebody was like, congratulate, like somebody texted me this, this connection to a tweet, a link to a tweet, and I was like, oh my God, like literally, I felt like my heart stopped. I could not believe it.

Liam Curley: Throughout the trajectory of the history of the show, there are these fat tailed events that trigger spikes in growth and opportunities that follow those spikes. Here's Debbie speaking with Jonathan Fields on Good Life Project.

Debbie Millman: When Tim Ferriss was on the show, that grew the show considerably and it allowed me to get other people of his calibre on the show. When Tommy Kail, the director of Hamilton, was on the show, that took me to another level. And so Amanda Palmer, when she was on the show, that allowed me to get more engaged with musicians so I can pinpoint a few over the years and say if it weren't for them, I don't know that I'd have as much success.

Liam Curley: According to the latest figures I have, Design Matters currently gets in the region of 500,000 downloads per month. And during the past 22 years that the podcast has been running, Debbie's fame and following has continued to expand exponentially and incredible opportunities have followed. She's published eight books. She became editorial director and co owner of Print magazine. She's co created with Steven Heller the world's first graduate programme in branding at SVA. She became president emeritus of AIGA, one of only five women to hold the role in its 100 year history. She's spoken at TED and Design Matters is now part of the TED Audio Collective. She hosts and records Design Matters events across the US. She talks on stages around the world. She met Michelle Obama at the White House in 2024. Harvard Business School made her an Executive Fellow after writing a case study on her two years earlier. She even met her wife, acclaimed author Roxane Gay, indirectly through the podcast. All of this success, including earlier success with Sterling Brands and Speak Up, came because of her ability to handle rejection. Debbie quotes Dani Shapiro when she says that confidence is overrated. What's more important is courage. That to succeed at anything you have to step into the act of doing it over and over and over. At first that'll be uncomfortable and you'll fail a lot. But if you continue in time you begin to successfully pull the thing off. And when you achieve that success repeatedly, you become confident. Debbie has courage.

Debbie Millman: I actually talked to Roxanne, my wife, about this a couple of days ago. It's New York Design Week and I've been going to a lot of different events and I've been working now in the design world, in the design business in New York for 43 years. The first 10 were what I consider to be experiments in rejection and despair. The second was sort of a learning how to walk kind of situation. So the 20s were really quite humiliating. The 30s got a little bit better. By the end of my 30s I started to find my footing and that really was when I got to Sterling and that I got to Sterling. I was already in my mid-30s and didn't really begin to make a name of of Sterling until I was in my late 30s and then didn't start Design Matters until my mid-40s. And so all those first two decades of sort of clawing my way through the design world. I think that I. That a lot of people have been somewhat baffled by my resilience and longevity in the business now, because, really, for those first 20 years, people just treated me terribly. They made fun of me. They called me names, they kept me out of things. They kicked me out of things. I mean, it's. I can laugh now. I can only laugh now because I think I've. I've reached a place where I don't think people would do that anymore. What I was saying to Roxanne is, it's so amazing to go to events like I'm going now, and people are really nice to me. Like, at first, you'd be like, why is she here? And looking almost like somebody farted or something. Like, why is she here? What is she doing? When Sandra Bullock got her Academy Award, she said something that. I'm gonna paraphrase it terribly.

Liam Curley: Debbie is talking about Sandra Bullock's speech at the 2010 Oscars when she won Best Actress for The Blind Side. Rather than paraphrase, here is Sandra Bullock at the Oscars.

Sandra Bullock: Did I really earn this or did I just wear y'all down?

Debbie Millman: She had been in sort of so many mainstream rom coms, and then finally she had started showing her chops as an actress, and then she got the Academy Award, and she's like, okay, I get it. I know I've just worn you down. And there are times where I feel like that, too. Like, she's here again. All right, let's just let her in. It's just easier than holding the door shut.

Liam Curley: I don't know whether or not Debbie wore down the market, but she certainly earned her place in it as a creative and an authority on branding. And the irony of the way in which this authority on branding built her authority is that she did it in a way that conflicts with the modern phenomenon of personal branding.

Debbie Millman: I find the concept of a personal brand problematic in that I know enough about brands to know that any brand is manufactured, meaning you birth a baby, not a brand. You grow an orange, not a Tropicana. We as humans have the ability, the only species on the planet that have the ability to imbue meaning into an inanimate object. That object has no say in it. I can say that this is tissues. This tissue isn't deciding whether it wants to be a Kleenex or a Puffs. There's no decision making between this inanimate object. We imbue meaning on this. This actually was originally created to take makeup off, not to use to blow your nose again. We constructed it, it was more popular as a brand. People found that they were using them as disposable handkerchiefs and a brand was born. That brand didn't wake up one day and say, hey, excuse me, Mr. Kimberly Clark. We think we'd be better used as tissues for the nose than tissues for eye makeup. So when you aspire to be a brand, you're aspiring to be fixed in one place. You can go to any design blog, any culture blog, probably almost any magazine blog. Whenever there's a discussion about a brand changing, there's usually quite a kerfuffle over whether it's a good idea or not. Reputations have been made and broken by the design or redesign of a brand. Brands are constructs made by people to communicate, telegraph, assign, affiliate meaning. But they don't breathe on their own, they don't live on their own, they don't have decisions, they're inanimate. So when somebody says they want to be a personal brand, what they're saying is that they want this association of attributes to be put on them and to be known for those attributes. What if you want to evolve? What if you want to change your hair? There's so many things that go into being a fixed entity that I don't think people fully understand. So what I suggest people do instead is work on building your reputation, work on building your character.

Debbie Millman: If you can build your character, then if it's embedded in that character that you're on a search for meaning and that you're always trying to grow and learn, you can continue to grow and learn and change. Like that makes sense. People tell me all the time like, wow, you've really changed over the years. I'm like, yeah, that's what I want. I don't want to be the same person I was when I was 40, God forbid. And so you can own a brand, you can manage a brand, you can own lots of brands, you can sell a brand. But the idea of trying to be a brand seems to me like you're taking out the fundamental fun and delight and joy of being a human. I want to be a human. I don't want to be a brand.

Liam Curley: Yeah, you take out the opportunity to grow and, yeah, pursue and make whatever.

Debbie Millman: Change you want to make without an opinion poll.

Liam Curley: Debbie's success with Sterling Brands came from the unique lens through which she recognised what a successful brand looked like in consumer packaged goods. Through childhood, she was interested in making things, in painting, in drawing and in writing. But she was also fascinated in how and why people made buying decisions and how packaging worked to influence those decisions. By running her own firm, Sloane Millman, she also developed the craft of presenting and selling creative services to clients, a craft she further honed at Frankfurt Balkind and which would be critical in the growth of Sterling Brands. She had a skill set through which she could make branding decisions informed by her intuition on every different aspect of brand presentation. Then when she was torn down by peers at AIGA and then Speak Up, through her own courage, she overcame the very public negativity surrounding her worth as a creative and would go on to write for the very people that doubted her. That courage triggered the chain of events that would lead to Design Matters, a creative pursuit which then took Debbie to another stratosphere in regards notoriety and opportunities. Design Matters wasn't an overnight success, though she did get early signals of resonance from friends and friends of friends. She'd created 100 episodes before being recognised by Design Observer and the first major recognition for the podcast came seven years after launch. Further examples of her habit of doing a thing over and over until she had confidence. The activity of building a personal brand is one that looks inwards, not outwards, selecting the attributes you want to be associated with, constructing a public facing persona to match, then communicating those attributes over and over until they become a reality in the minds of the consumer. That was never Debbie's focus, nor is it the focus of any authority I study. Her focus was on her craft, how to solve meaningful brand packaging challenges, how to think about those challenges and how to articulate thinking around the solution. And she explored other areas of interest and art and brought that to her work on brand. Those layers are fundamental in developing the thinking that uniquely looks and sounds like Debbie Millman. Then it became a focus on interviewing great designers and publishing fascinating, insightful conversations on designing a creative life. And by broadening the application of her thinking, she became a crossover authority. For an individual, meaningful differentiation and brand is not an activity, it's an outcome. Debbie Millman has achieved incredible feats because she didn't try to build a personal brand. She pursued curiosity, applied her broad skill set to a craft in one narrow field, then when she had a platform, broadened the application. That is how Debbie Millman became the undisputed authority.

Liam Curley: Thank you for listening. This podcast was produced by Jamie Slevin, edited by Magnus Kramers, and researched, written and narrated by me, Liam Curley. I help experts develop the positioning frameworks and insights that differentiate them from everyone else in their field and I've created a free email series called the Ten Patterns of Disruptive Wisdom. In my research of undisputed authorities, these are the consistent behavioural patterns I noticed among those who rise to the top. To get the email series, head to liamcurley.co.uk. Link is in the description.

‍