The Tim Ferriss Show Transcripts: Debbie Millman (#214)

Please enjoy this transcript of my interview with Debbie Millman, founder and host of Design Matters, the world’s first and longest-running podcast about design. Transcripts may contain a few typos—with some episodes lasting 2+ hours, it’s difficult to catch some minor errors. Enjoy!

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#214: How to Design a Life - Debbie Millman


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Tim Ferriss: Hello, ladies and germs. This is Tim Ferriss and welcome to another episode of the Tim Ferriss Show where it is my job each episode to deconstruct world class performers of all different types, from entertainment to sports, chess, military, and everything in between to tease out the habits, routines, thought processes, decision-making processes that you can use and test yourself.

This episode we have a very, very special treat, and I will say in advantage we cover some very, very deep, hard and also, sensitive material in this episode. For some people who listen to this, it will be I think the most important podcast episode you’ve ever listened to, and that has nothing to do with me; it has everything to do with the stories and lessons of Debbie Millman. @debbiemillman on Twitter and elsewhere – you can say hello – is “one of the most influential designers working today,” by Graphic Design USA.

She is also, the founder and host of Design Matters, which is the world’s first and longest podcast about design. She’s interviewed nearly 300 design luminaries and cultural commentators including Massimo Vignelli, Milton Glaser – with an S – and remember that name; he will come back.

Her artwork has been exhibited around the world. She’s designed everything from wrapping paper to beach towels, greeting cards to playing cards, notebooks to tee shirts. And if you’ve heard of, say, Star Wars, she worked on the merchandising. Burger King; the redesign. Hershey’s, Tropicana. At one point, if you walked into any given grocery store or supermarket, anything like that, she had a hand in about 20 percent of everything you might see or touch. She is the President Emeritus of AIGA, one of five women to hold that position in the organization’s 100-year history.

She has six books that she’s authored. And in 2009, Debbie cofounded with Steven Heller the world’s first master’s program in branding at the School of Visual Arts in New York City, where I’ve spent some time. Now in its eighth year, the program has achieved international acclaim. We cover a lot. We cover facing rejection, overcoming personal and professional crises of faith.

This is one of the most powerful conversations that I’ve ever had on this podcast. So, without further ado, please enjoy and think hard on, reflect on, this conversation with Debbie Millman.

Debbie, welcome to the show.

Debbie Millman: Thank you, Tim. It’s really wonderful to be here.

Tim Ferriss: I have wanted to interview you on numerous occasions now over the last few years so, I am thrilled that we are finally doing this, point number one. And I thought I would start with a question that for someone like yourself who has explored so, many different things in so, many different formats, when someone asks you what do you do; let’s say you meet someone at a party and they say, “What do you do?” What is your answer to that?

Debbie Millman: That’s a tough question. What do I say? Well, now I say that I’m a designer and sometimes if I’m feeling wordy, I’ll say that I’m a designer and a writer and a podcaster.

Sometimes people look at me like huh? Like huh?

Tim Ferriss: Too many hyphens; what does that mean?

Debbie Millman: Exactly. When I was working at Sterling Brands, which I did for over two decades, I had resolved to just saying, when I was filling out what I did on passport applications and things like that, I used to say “executive,” and that made sense.

Tim Ferriss: Executive is a great catch-all, exactly.

Debbie Millman: Executive is a great catch-all. For a long time on Twitter I had “Debbie Millman is a girl” until enough people said, “Debbie, you’ve really got to change that,” and than I did.

Tim Ferriss: Oh, the internet. You can put anything there and I think about 10 percent of the people who come across it will be outraged for one reason or another.

Debbie Millman: Oh, yes. I’ve found that the very things that delight and excite some people are the same, exact things that outrage others. It’s really hard to please everybody all the time.

Tim Ferriss: Yeah, I think that if you try to please all the people all the time, you’ll just end up displeasing yourself all the time. That’s the only guaranteed outcome there.

Debbie Millman: Oh, Tim, I learned that the hard way.

Tim Ferriss: I want to talk about so, many things, Debbie. For those people wondering, I always ask my guests beforehand, are there any particular prompts for stories that we could explore that might be fun to dig into. And one of them was drawing you did when 8 years old. I know nothing about this and I just want to start there, since it seems to make sense to begin at the beginning.

Debbie Millman: Well, I have somewhat of a packrat mentality. I keep things. I’m a sentimentalist at heart and I like to keep things from all different stages of my life.

I have boxes of journals, and drawings, and all sorts of of report cards; you name it I have it. Apparently, I got this trait from my mother, who a couple of years ago, did what a lot of good, old Jews do; she moved from Queens, New York to Florida.

Tim Ferriss: The great migration.

Debbie Millman: Yes. And before she moved, she unloaded several boxes of affirma of mine that she had kept, unbeknownst to me. I went through everything quite gingerly – it was all sort of folded up very neatly and very tidily – and came across an illustration that I did when I was about 8 years old. After I admired my handiwork – because I thought wow, 8 years old, I was rocking the drawings – I realized that this particular drawing had predicted my whole life.

So, I will try to explain this drawing as best as I can. And first, some back story. I am a native New Yorker. I was born in Brooklyn. When I was about 2 years old, my parents took me to Howard Beach, Queens. I moved there before there were any sidewalks. That will give you a little bit of a sense of how old I am. I lived there until I was in the middle of the third grade, and we moved to Staten Island. I lived on Staten Island until I was in the fifth grade. At the end of fifth grade, my parents got divorced.

My mom took my brother and me – he’s two-and-a-half years younger than I am – to Long Island. My childhood was spent in almost all of the boroughs except Manhattan. For some reason, I had I guess a sense of what Manhattan looked like and felt like probably from television.

At 8 years old, I drew a picture of the streets of Manhattan. I’m a little girl and I’m walking along with my mother. My mother, by the way, is wearing a very popular Barbie outfit of the time, an outfit called “Tangerine Dream,” which I really loved. I put her in that outfit. And despite not having a lot of time on the streets, or any time on the streets of Manhattan, I drew it in quite good detail. There were buildings and busses and taxis, and I labeled everything. I labeled the cleaners “Cleaners,” and I labeled the bank “Bank,” and I labeled the taxi “Taxi.”

In the middle of the street there is a delivery truck. I not only labeled the delivery truck; I also, drew the sign on the delivery truck. And the sign was “Lays Potato Chips.”

I drew the logo at 8 years old. When I saw this drawing, I realized that I had predicted my whole life. I’m a native New Yorker now living in Manhattan; I’ve been living in Manhattan for 33 years. I go to the bank, I go to the cleaners, I take lots of taxis, lots of busses. And at the time I found this drawing, I was drawing logos for a living.

Had I known that it would have been that easy just to follow that drawing, I would have saved decades of experiments and failure and rejection.

Tim Ferriss: So, this is fascinating to me for a number of reasons. I’ve had a few guests on the podcast – Chris Sacca would be another example; he is an investor and he at some point wrote in a journal.

I think it was one of these composition notebooks with the model black and white, zebra slash camouflage covers –

Debbie Millman: Oh, I love those!

Tim Ferriss: – what he would be when he was 40 years old. And he must have done this when he was 10 or 12, something like that. He found it in I think his parents’ garage later, around the age of 42 or something like that. It also, predicted effectively exactly what he would be doing. But it was lost in the slipstream, and he took this very meandering and in some ways odd, seemingly fractured path to come back to right where he started, in a sense.

It sounds like you didn’t follow that plan that was so, neatly summarized in this picture. Because there are folks out there who say: you know, when I was 5, I knew I always wanted to be X. But when did you figure out that you wanted to actually do what was in that drawing on some level; that you wanted to be a designer?

Debbie Millman: I actually never set out to be a designer.

I thought that I was going to be a journalist. The only thing that I knew for sure when I was in college was that when I graduated, I wanted to live in Manhattan. At that point I had never lived in Manhattan, and that was my big dream. I came to Manhattan the summer of 1983. I often say that that was the summer of David Bowie’s Modern Love and the Police’s Synchronicity. I saw both concerts that summer.

I moved into a sublet apartment with a friend that had also, recently graduated. She had found a sublet on the corner of Hudson and Perry Streets in the Village. I didn’t know it at the time, but moving into an apartment on the intersection of Hudson and Perry was almost as if I was entering the movie Gidget Goes to Manhattan.

I didn’t know where I was going. It was quite serendipitous. My friend Jay found the apartment for us. Unfortunately, that wonderful summer turned out rather unfortunate because the woman who Jay and I were subletting from, rather than paying the rent with the rent money she was getting from us was keeping it and not paying the rent. So, at the end of the summer, we all got evicted.

Tim Ferriss: Surprise!

Debbie Millman: I ended up appealing to the landlord to please, please help me find someplace else to live because I really didn’t have anyplace else to go. He ended up being able to rent me another one of the apartments he had in another building he owned on 16th Street, which was a fourth-floor tenement walkup; a railroad flat that I couldn’t afford on my own and ended up living with a couple; my roommates were a couple.

Because it was a railroad flat, I had to walk through the apartment, which meant through their bedroom to get to mine. Which often meant I was stuck on one side or the other, depending on their nocturnal habits.

Tim Ferriss: What was going on…

Debbie Millman: Or afternoon delight, depending on what they were doing. I lived there for about five years before I ended up moving back into the Village for a short period of time. So, that was the one thing that I knew I wanted; to live in Manhattan. I did not know that I could be a designer, that I would be a designer, or that design was even a discipline until my senior year of college. I had worked my way up to be the editor of the Arts and Feature section of the student newspaper at SUNY Albany, where I went to school and realized very quickly that as much as I loved assigning articles and coming up with themes for this section of the newspaper, I was endlessly fascinated by putting the paper together, by designing the paper.

And thus, a baby designer was born. I took all of one class in design when I was in college and really learned almost everything I knew at that time working in the newsroom, putting the paper together. Everything was done old school: layout, paste up, compugraphic machine, stat cameras. Then when I graduated, was both doing editorial and freelance layout and paste up for the first couple years of my career.

Tim Ferriss: When did you start at the school newspaper, or was that something you started at the very beginning and followed throughout your undergrad experience?

Debbie Millman: Interesting and perceptive question, Tim. I wanted to write for the student newspaper I think the very first issue I saw when I got to SUNY Albany, freshman year.

I went up to the student newspaper, which was on the third floor of the campus center, and approached the editor at the time and asked if I could be a writer, or offered my services; volunteered my services. He looked at me and asked me if I had any clips. I didn’t say what I was thinking, but I was like hair clips? I mean, I didn’t know what he was talking about. I didn’t have anything, and I didn’t know what to do and I was embarrassed and humiliated and ashamed, and sort of scurried away.

I didn’t go back until my junior year. I was so, intimidated by the talent and the work that was coming out of that newsroom. And it was at the time, and very well may still be one of the best student newspapers in the country.

It came out twice a week, Tuesdays and Fridays and I was just enamored with this newspaper. I fantasized about writing really piffy erudite letters to the editor in chief that would then get published in the Letters to the Editor section, and they would realize what a great writer I was and they would invite me to be a reporter, and I’d sort of walk around like Rosalyn Russell with a pencil behind my ear and my heels click clacking in the newsroom. Of course, that never happened.

I never wrote one letter to the editor. And for some reason and I guess an abhorrent moment of courage, I went back up to the newsroom my second semester junior year. There was a women’s uprising in front of the student health food store. They’re like, “Could you go cover that?” I was like yeah, absolutely.

I went and did it, and that was how I started writing for the paper. I then wrote a piece about an exhibit in the Art Center. By the end of my second semester junior year, only because no one else would take it, I was offered the job of being editor of the Arts and Features section and began that summer. That senior year in college was one of the most exciting and best years of my life in that for the first time ever, I felt like I had purpose. Suddenly, working on this paper I felt like I was part of something bigger than myself. I felt like I had some reason for being, and I loved learning about design. I loved being able to work with writers and I felt for the first time in my life really excited about something.

Tim Ferriss: I want to talk about that abhorrent moment of courage and dig into that a little bit. So, you were rejected from, or maybe your rejected yourself or both, initially, when you approached the paper. Then, years later, you have this abhorrent moment of courage. What precipitated that? Was there a conversation, a realization, you watched a movie? What triggered that? Do you remember?

Debbie Millman: I actually don’t. I wish that I did; it would make for a much better story and certainly a better interview. What I can tell you is that all these years later, I have noticed a pattern in my life of being very easily hurt by an initial reaction or an initial rejection. So, much so, that it thwarts any other attempt at making something like that happen for a very long time.

I am extremely sensitive, and any rejection sort of takes me off of that path for quite a long time, and it takes me awhile to recover.

Tim Ferriss: Could you give any examples of that?

Debbie Millman: I would say my entire life. I can give you 43 examples; get comfortable, Tim.

Tim Ferriss: I’m definitely settling in with my water; I’m ready to go.

Debbie Millman: Well, there I was, rejected that first year of college. It took me then three years to go back again. I might have been feeling confident about something else that had gone well in my life and thought what the heck, why not go back and try and then took those steps up to the Campus Center, and went back up to the third floor and asked again.

I am somebody that has a very hard time taking no for an answer but it takes me a long time to recalibrate and get my courage back to continue to keep trying.

When I graduated, because I had such a hard time finding a job initially that I really loved, and because I was having so, much trouble figuring out what I wanted to do with my life, I kept bouncing around from opportunity to opportunity. Every time I would try something new and would ultimately get rejected, I used that first rejection almost as a permission slip to avoid having to try again.

So, when I graduated, I started working at a couple of different magazines. I worked for a cable magazine and I worked for a rock magazine doing layout and paste up and some editing. And at the time thought I’m really enjoying this but I don’t really feel qualified doing this; maybe I should go back to school and get a master’s degree in journalism.

I lived in the neighborhood of a very good journalism school, the Columbia School of Journalism. My dad had gone to Columbia and studied pharmacy, and I thought why not apply to the Columbia School of Journalism? But that was the only school I applied to. I thought I wanted to consider getting a master’s degree in journalism. There are a lot of good journalism schools in New York City but for some reason, I had my heart set on this one school. I didn’t get in; I got rejected and abandoned my hopes or dream of going to get a master’s degree in journalism.

Shortly thereafter, because I also, am a painter, I had been accepted into a show at Long Island University the Brooklyn campus, and got some good reviews. And I thought hmm, maybe I should become an artist. I love doing this; I’m getting some good response from it but I don’t feel qualified or educated enough. Maybe I should get an advanced degree in art.

The Whitney Museum of Art had an independent study program that would allow me to continue working during the day. I applied for that. I had really good references, wonderful clips at that point, some good reviews and I got rejected to that and then abandoned that dream. And so, it’s been a long history of making an attempt, getting that early rejection, retreating, and then finally sort of licking my wounds, re-knitting my confidence or hopes and dreams together, and then trying to do something else or trying again.

Tim Ferriss: So, a few questions. The first is what would you say to your college self after that first rejection at the newspaper? Or what advice would you give someone who had the near identical experience and was hardwired the same way?

Debbie Millman: Well, it’s an interesting question, Tim, because I have the benefit of hindsight. And looking back on those years, yes, I certainly could have tried again sooner and maybe had more of a runway to experiment and grow and learn in that newsroom and in that environment. But I also, think that those years in between learning and growing in other ways contributed to my ability to then, when appointed the editor of the Arts and Features section, I somehow had a lot more to pull from.

And maybe this is my own synthesizing happiness or calibrating to my own set point, or looking back and thinking well, it all sort of worked out so, why give somebody advice that I wouldn’t have necessarily taken at that point?

What I would say is don’t accept the first rejection, ever. Give yourself options. The timeliness of those options, or the timeliness of those retries do at your own pace. You’re not in competition with anybody but yourself. So, if you are rejected from something that you want, then think about what it is that caused that rejection and work to better understand how you can present your best possible self when you try again.

Tim Ferriss: Your clips mention, where you’re like “Clips? Hair clips?” reminded me of a story I heard when I was a student.

You work with a lot of students, and we’re going to come back to that.

Debbie Millman: Oh, Tim, can I add one more thing? I’m sorry.

Tim Ferriss: Of course.

Debbie Millman: This is an interesting –

Tim Ferriss: You can add many things; please.

Debbie Millman: So, one thing that I haven’t shared about this particular story is that the young man that rejected me that first year is somebody that I then befriended in that experience of working at the paper that junior year. I graduated in 1983. It is now 2017 and I have been friends with that man – his name is Robert Edelstein. I have been friends with him ever since. So, just because somebody rejects you doesn’t mean that they don’t like you. First of all, he didn’t even reject me; he asked me for something very reasonable.

He asked me for some examples of my writing. I was so, intimidated and was so, embarrassed by not knowing exactly what he meant and the fact that I didn’t have anything other than some things from high school which I didn’t feel were appropriate, that I was the one that rejected myself in many ways.

One of the interesting things that I have found, and Rob is not the only person that I can point to as being somebody that initially provided some sort of obstacle or roadblock that was a reasonable one and then ultimately, I befriended and we are now lifelong friends. He didn’t even remember rejecting me that freshman year and is mortified now by the notion that he might have done anything to hurt my feelings.

So, one of the other things that I would suggest that people consider if they believe they are being rejected is consider what the perception from the other person doing the rejection – or the supposed rejection – might be. And that sense of empathy might be really helpful in understanding where you’re coming from and what you’re bringing to that specific example or that specific experience.

Tim Ferriss: I’d like to underscore this because it’s such an important point. And I, in some respects like you, have been very sensitive; I still am, in some respects, very sensitive. My particular brand of that, or my particular type of response is to feel some type of sense of injustice. So, I will get rejected, and looking back at what I see as a rejection…

When I did this perhaps ten years ago; I looked at a number of instances where I felt like I had been rejected via email and so, on that A) it wasn’t a rejection for all time; it was a “not now.” It was a very temporary impossibility due to logistics and I took that as a “no, not ever” and felt very hurt by that and didn’t try a second time in many cases.

Debbie Millman: Absolutely.

Tim Ferriss: So, No. 1, “no” may just mean “no, not right now.” You can even clarify that; you can ask that as a clarifying question. No. 2 is that at some point someone said to me, and this doesn’t apply to your particular instance, but “Don’t ascribe to malice what can be explained by incompetence.” That didn’t cover it all for me but it really made a profound impact on me when I was told this. Because I would read email, inserting as if I were doing an audio book of the other person’s voice, some type of really angry or upset person.

And nine times out of ten, that wasn’t the tone at all. It was just I was misreading it. So, I started to assume for myself, don’t ascribe to malice what can be explained by incompetence, or just business; the person is busy. If they send you a really short response to your mini novella of an email, it doesn’t mean they think you’re worthless or not worth their time. It could just mean that they have ten times more to do than you do. And it’s sometimes hard to have that perspective when particularly you’re starting out, and you’re a bit fragile and you’re on wobbly legs.

And you send this huge outpouring of your emotion to someone you respect and they respond with: “Sorry, kid, not right now.” And you’re like: really, that’s it? And then you die. I’m not going to name names but there’s someone who now I’m very close friends with’; an extremely well respected writer. And I got one of these one line responses in 2005 or 2006 when I sent an early manuscript of the The Four Hour Workweek to this person via email. The response was effectively “Thanks but sorry; I don’t have time to read this right now.”

No “Dear Tim,” no signature; just one line. And I felt so, slighted by this that I held this subconscious grudge for years and now we’re really good friends, and the whole thing is ludicrous in retrospect.

Debbie Millman: One thing that I find about human nature is that ambiguity is always perceived negatively. So, there might be nothing in that one-line email that would be in any way disparaging or insulting or anything. But because we as humans perceive ambiguity negatively, we tend to read into things that aren’t there in a way that makes us feel bad. But I also, think that a lot of that, for me, comes from having a very sort of fragile center and not necessarily thinking that they are specifically upset with me because of something that I’ve done but just because everything that I do is sort of bad.

They’re just cognizant of that. So, it’s not something specific; it’s just something all encompassing. So, that’s been something I’ve been struggling to overcome over the decades.

Tim Ferriss: I have a few questions about how you came to find your niche, or the first time you clicked into place, so, to speak, doing something that resembles what you ended up doing up to this point. But before I get to that, just to put a button in the anecdote related to clips. You mentioned clips; you were like “Clips? Hair clips?” I was told this story by a professor in college about Nantucket Nectors when it was just getting started. And there are I believe two guys who were really faking it until they made it, in a lot of respects.

And at one point they were meeting with this distributor because they had been selling these concoctions via boats in Nantucket, from boat to boat tot boat. They wanted to go into retail and had met with either a retailer or a distributor, but it was early on. They were really nervous and the muckety-muck they were meeting with, at least in their eyes, said, “Do you have a lot of POS materials?” And they looked at each other like “oh, shit.” And they said “Oh, POS, we’re all about POS.” And he’s like, “Good, good, good.” And then they walked out and they were like, “What the hell is POS?”

Point of sale, which of course you know plenty about. But before we get to when you first clicked into your niche and how that happened, you mentioned knowing that you wanted to be in Manhattan.

I’ve been thinking a lot about the components of – and this is a dangerous word sometimes – happiness and that oftentimes we think of let’s say the journalist Ws, the interrogatives: the why, the what, the where, and so, on of happiness. I think humans tend to at least put “why” at the top, and then maybe “what” somewhere lower, and “where” is often an afterthought. But I’ve started to believe that the “where” is much more critical than we give it credit for, and you can actually start there.

So, I’ve thought about this a lot for myself, really how important the geography can be because it determines in large measure who your surrounded with all the time, and what you’re surrounded with all the time. But I guess that’s more of an observation than a question. But if you think about that, how do you think about the components of happiness or well being for yourself?

Debbie Millman: That’s a big, big question, Tim.

Tim Ferriss: Oh, yeah.

Debbie Millman: Well, there are sort of two parts to the question, I think. And the first is this notion of New York being the place that I wanted to be. And what I told myself at that time, and then ultimately how that leads to happiness or fulfillment. One of the things that I struggled with when I first moved to Manhattan, or when I first graduated, really, was what was I going to be? What was I going to do? I didn’t have a lot of money. I didn’t have any network. And I certainly didn’t have any type of connection to any ins for apartments or jobs or anything like that. And I wanted very badly to be in Manhattan; that was something that I knew for sure.

In thinking about what I wanted with my life, I knew that I wanted to do something creative. One of my big hopes and dreams at that time was to work at Condé Nast, and I did apply and I did get a call back. And I got rejected and then never tried again; another example of that. But one of the more higher altitude aspirations was either being an artist or being a writer; so, being more of a fie artist and not a commercial artist.

But at the time, I did not think that my chances of success at that would either be possible and certainly, if it were possible, not fast. And because I wanted to live in New York City, because I wanted to live in Manhattan, I felt that I needed to be able to get a job that would pay my rent.

And because I didn’t want to be a waitress, and because I didn’t want to be a bartender, I needed to make some type of reasonable income in order to pay that rent. And so, I have been telling myself for decades now that I decided that I needed to work as a designer because I needed to have some sort of income that would give me some sense of self efficiency.

Self sufficiency has been enormously important to me, and I’ve said that for years and years and years. And that being safe and secure and being able to manage the course of my own life, having financial stability that was something that was a bit of a lead gene for me in making the decisions that I did.

And back in that summer of David Bowie and the Police, I remember coming home from a club one night and I was on the corner of Bleaker Street and 6th Avenue, and it suddenly occurred to me that I had to make a decision. And the decision was what was I going to do? I realized that if I wanted to be an artist or a writer, that I would likely have to take some type of job that would not necessarily be able to safeguard what I considered to be my financial future.

And therefore, made this little pact with myself in my head that I would become a designer so, that I could make enough money to be able to be secure. And I’ve been telling myself that for decades. What I realized in the last couple of years, was that I was, unbeknownst to my psyche, my consciousness; I was lying to myself. I was absolutely, positively lying to myself.

Because more than the self sufficiency was the desire to be in Manhattan. I could have more easily become an artist, or a fine artist, or a writer if I didn’t want to live in the most expensive city in the world. I could have gone and lived with my mother in Queens. I could have lived with friends in Albany. I could have had seven roommates in a little commune in Bed-Stuy. There would have been any number of things that I could have done if my lead gene had been artistic purity.

But no, I told myself that it was because of XYZ but really what it was was the most important thing to me at that point in my life was being in Manhattan. And I lived in a fourth-floor tenement walkup.

I had to walk through somebody else’s bedroom to get to mine. I was living on a floor with people that were constantly – the other tenants in the building were locking each other out. It was an elderly couple and they were always fighting. There were a whole family of pigeons living on the fire escape outside of my window in my bedroom, which was so, decrepit I couldn’t even open the window in the summertime. And there was no air conditioning in this apartment. The conditions that I lived in were deplorable. But yet, that was the most important thing to me.

So, when I talk to people now about what they want to do when they first graduate, I ask them to think about what is the one most important thing to you? What is the one most important thing to you? Because if it is truly the one most important thing to you, you will likely do whatever it takes to get it.

And the most important thing to me was not being a writer, and not being an artist. It was living in Manhattan, and I did whatever it took, and lived in whatever conditions that I needed to in order to make that happen. I think that’s a really important realization.

Tim Ferriss: Oh, definitely. So, by hook or crook you’re living in Manhattan.

Debbie Millman: Yes.

Tim Ferriss: So, that is the outcome, in part, of all these decisions and the lead gene as you put it. Where does the need for stability, security or the desire for that come from?

Debbie Millman: Well, I do think that it’s certainly in Maslow’s hierarchy of needs a really important one.

Tim Ferriss: For sure, yeah.

Debbie Millman: For me, it takes on an extra level of significance in that I grew up in a really, really challenging environment.

My parents got divorced when I was very young; I was about 8 years old. I had a very, very complicated relationship with my father. My father died last year unexpectedly. My father, in my daughter eyes, was brilliant, charismatic. He was an incredibly well spoken man. He was also, extremely turbulent. He had a lot of anger issues and over the course of our lives together, I had five different experiences with him where he rejected me and decided that he didn’t want me in his life. One of those periods was about nine years. So, we had a very, very turbulent relationship.

When my parents got divorced, I told myself at the time that I was really happy about that because I was so, scared of his anger and so, scared of the anger that they had for each other. About a year after my parents got divorced, my mother married again and she married a man who was physically and sexually abusive to me, physically abusive to my brother, and also, sexually abusive to one of his two biological daughters and severely, severely beat us for four years. During that time was one of the times – the first time, actually, that I was estranged from my biological father.

So, I had a lot of brutality in my life. After they got divorced, I was 13. My father came back into my life. My mother then got involved with another man who was ten years younger than her, so, therefore only ten years older than me and was also, – I guess I’ll put it sexually provocative with me, and also, emotionally abusive. So, for the first 18 years of my life I lived in a state of constant terror and compensated, or self soothed, with art and a lot of extra curricular activities in school.

I was always an overachiever, probably in an effort to prove to myself and to my family that I wasn’t worthy of the abuse that was being inflicted on me. I wanted so, much more for my life, even back then.

And I grew up thinking that if I had the resources to take care of myself, that I would never allow anything bad to happen to me. Not quite a realistic expectation but was something that I felt was possible to do. Of course, it’s not; that takes decades to also, figure out. But at that time, I wanted very badly to be able to live in my own home, to be able to take care of myself, and to be in a position where I would never be vulnerable again. You know, sort of Scarlet O’Hara: “I’m never going hungry again!” Yeah, it doesn’t always work out that way but it was definitely the journey that I’ve been on.

Tim Ferriss: Thank you for sharing that; I had no idea.

Debbie Millman: It’s not something I talk about a lot, mostly because I’ve had an enormous amount of shame about it and that’s a very normal thing, and still do.

And it’s still very, very hard for me to share these types of things. But I do think it’s important that people do see that there is hope for a better life, even when you are the victim of these types of situations. I’ve spent a lot of time working on better integrating those experiences into my life in a way to not only understand what happened, why it happened, what the aftermath then caused but also, how I can use that empathy and that understanding to try to help the world.

And that’s a lot of the reason that I’ve started to do the work that I do with Mariska Hargitay and the Joyful Heart Foundation which is a foundation that Mariska started after she started working on Law and Order SVU. Shortly after she started working on that television program, she started to receive a lot of letters from people, the very victims she was trying to find justice on the television show and realized that this is way more than a television show; this is a huge opportunity to make a difference in our culture.

And shortly thereafter started the Joyful Heart Foundation, which is an organization to help irradiate domestic violence, sexual assault, and child abuse. I’ve been working with Mariska and Maile M. Zambuto, the CEO of the foundation, for the last five years.

I believe this branding work that I’ve been able to do with them, taking into all the expertise I’ve had in repositioning and branding some of the biggest CPG companies in the world and now dovetailing that with my own background, really, truly makes me feel like my whole life makes sense, Tim.

Tim Ferriss: That’s beautiful. I’m really glad you’re talking about this because I can imagine a very different experience but I’ve had my own battles with darkness of different types. And it’s very easy to believe that you are alone or isolated or that things will never change. I’m sure there are people listening who have had similar experiences to yours who have never talked about them, or have never found a way to perhaps integrate or reconcile them. And this might be an incredible catalyst for them.

I would love to ask, if you’re open to talking about it for yourself, have you found any particular avenues or types of work to be particularly helpful to you?

Of course the work that you’re doing with the Joyful Heart Foundation but apart from that, are there any particular types of exercises or work, or anything really that has helped you to be more at peace with your experience?

Debbie Millman: I think that the work that I’ve done in therapy has saved my life. I have always been really dedicated to my therapy and have been in therapy with the same analyst now for over two decades.

Tim Ferriss: What type of therapy is that, if you don’t mind me asking? I know very little about it.

Debbie Millman: The person who I work with is a PhD. She was very involved in the psychoanalytic community in New York City. She’s now living in Santa Fe. I think it’s a combination of a number of different philosophies and theories, probably at its foundation psychoanalysis but certainly with quite a lot of variations. It’s talk therapy. I started back in the early ‘90s five days a week, and then moved down to three days and now I’m usually two to three days. It is enormously helpful for me to try to make sense of these experiences that I’ve had.

For anybody that is either in the midst of experiencing them or experiencing the aftermath, there are a lot of resources. One of the things that I experienced when I was in the midst of these experiences was a sense of profound aloneness. The worst experiences I had were in the ‘70s. And at the time, the topic wasn’t one that was as understood. I didn’t know what was happening to me. I thought I was the only person in the world that this was happening to because it seemed so, surreal and unnatural and punishing. It didn’t occur to me that this was pervasive, that this was a cultural epidemic.

I was told at the time by the perpetrator that if I told anybody, that he had the resources to hurt my brother and my mother; that he would kill them.

Tim Ferriss: That’s horrible.

Debbie Millman: And I believed that. I was a little girl. I believed that. I was protecting them and I didn’t know that I had any other resources; none. And didn’t even tell my mother until after they got divorced. Because Tim, I didn’t want to be the reason; I didn’t want to be blamed. And I also, didn’t think anybody would believe me, and I didn’t want my mother and my brother to be harmed. It wasn’t until I was much older that I realized that this was pervasive. So, for anybody who is listening, if you feel alone, know that you’re not.

You can go to the Joyful Heart Foundation, the, and there are resources and phone numbers. You can also, go to, which is another organization that I’ve helped and there are resources and people who are there to help and listen and get you out of the situation that you are in.

Tim Ferriss: Thank you for that. To insert some levity, I’m not sure how to segue from here.

Debbie Millman: Let’s talk about some of the really important things that people are doing now to not only eradicate this type of violence, but also, to change the world. One of the other things that Joyful Heart is doing that I am so, proud of is ending the backlog. There are hundreds of thousands of rape kits that are not being investigated, that are sitting on shelves in police departments all over the country.

So, the Joyful Heart Foundation, along with Vice President Joe Biden, has been very involved in getting funding to help analyze those rape kits to be able to analyze the DNA and get serial rapists off the streets and get justice for the victims of those crimes. So, that’s a really, really important thing that they’re doing and something that I feel can ultimately change not only the rape culture that we’re living in, but also, the blaming of victims. So, we can change culture by doing this work together. It’s something I’m super proud of.

Tim Ferriss: To those people who are listening, all of these resources that are being mentioned throughout this episode will be in the show notes, so, you can certainly find links to, the Joyful Heart Foundation and so, on at, all spelled out.

Debbie, I’d love to ask you to shift gears just a little bit, or perhaps a lot. The “Speak Up” story.

Debbie Millman: That’s one of my favorite stories.

Tim Ferriss: I will let you run with it. I would love for you to share.

Debbie Millman: Okay. So, I want to start this story by letting people know that this was something that while it was happening, I thought was the worst professional experience of my life. And it’s turned out to be the most important and life affirming of my life. So, let me tell you a little bit about the Speak Up story. The year is 2003, and the time in the world was quite different than it is now. We were online, but we weren’t quite online in the way that we are now. I think YouTube was just, just beginning.

It was a video sharing site more than anything. We were online but we were playing games, and we were ordering from the J Crew catalog. I don’t know if people remember when the J Crew catalog went online, people’s heads exploded. You could buy things online and they could be shipped to you and you don’t have to leave the house; oh, my God, that’s so, amazing! We were playing games and we were emailing and reading the news.

There were forums where people would congregate but they tended to be more niche forums, and not so, much mainstream cultural forums. Leading up to that time in my life, I had joined Sterling Brands in 1995.

This was one of the first moments of that click that you had mentioned earlier where suddenly, without even realizing it, I had joined a firm where I was hired to help grow the business via the acquisition of new clients in branding. The job was one of the first times in my life where I was almost effortlessly successful. I think because of my early childhood in my father’s pharmacy, being surrounded by brands and my own obsession with things like Lay’s potato chips…

Tim Ferriss: I was going to say Lay’s potato chips.

Debbie Millman: Exactly. I had this almost magical ability to understand why and how people chose the objects that they did to be part of their lives; mostly the brands they chose.

So, I started working at Sterling Brands and had this heretofore unbelievable level of success financially. I really enjoyed it. I am also, endlessly fascinated by the choices people make for the objects in their lives, what they choose to surround themselves with, the kinds of things they buy and share and eat and wear and so, forth.

Inasmuch as I loved what I was doing, and inasmuch as I was relishing the level of success that in my early 30s I was finally, finally getting; I also, was still sort of longing for that artistic, creative part of my life that I felt was deeply missing.

Tim Ferriss: At that point what department were you working in?

Debbie Millman: I was working in marketing and sales. I wasn’t at that time doing very much design work.

I was doing some work freelance. I had been appointed the off-air creative director at Hot 97, which is a whole other story to share at some point. I was working to develop the identity and the graphics for the first-ever hip hop radio station, which happened to be in New York and was called Hot 97. That was the only thing I was doing on the side. I started working at Sterling Brands and was longing for a design community, and was longing for a feeling of being part of something bigger than I was on my own but something that was much more creative and had no commercial implications.

I found the AIGA, the American Institute of Graphic Arts. They had a special interest group within AIGIA called the Brand Experience Center. And I was so, excited. I thought oh, my God, this is the Venn diagram of my life!

I can do branding, and they have designers, and all these famous designers are on the board, and I could meet them and I could be part of this great community. So, I went and I volunteered, and I became a member of AIGA. I was working with this brand experience group and I loved it, and I was appointed to the board, and I felt really, really part of something. The board term was I think two years, and at the end of the term if we wanted to be on the board again, we all had to reapply.

In that two years, I was very active. I went to all the meetings. We weren’t funded by AIGA; we had to self fund. So, I made cupcakes for bake sales, and we had a flea market, and I was very, very involved in the sort of day-to-day runnings of this little special interest group. At the end of the two years, we all had to reapply if we wanted to be on the board again, and every single person reapplied. And every single person was appointed on the board again except me.

I was rejected.

Tim Ferriss: Oh, you set me up with the cupcakes. Oh, my God.

Debbie Millman: I know, and they were really good cupcakes, and brownies! And I was devastated. I was just devastated. And Rick Grefé, who was then the executive director, he had been aware of how much I wanted to be in AIGA, and how much I wanted to do, and my aspirations. I think he felt really bad for me. He asked me if I wanted to have lunch, and he took me to a very experience lunch at 11 Madison.

Tim Ferriss: Oh, that’s…

Debbie Millman: Yeah, it was super wonderful and generous of him. Over the course of lunch, he said, “Please, please don’t give up on AIGA. We need people like you and don’t give up. We’ll find a place for you; I promise.” I guess as a bit of a consolation prize, he asked me if I would be a judge in the upcoming annual competition that AIGA had called 365.

And he asked me if I wanted to be a judge in the package design category. This, to me, was almost worth being kicked to the curb by this special interest group of the brand experience end. This was like the biggest honor of my career at that point. To be a judge in the country’s biggest design competition was unfathomable to me. It felt like a miracle.

So, I went to the judging and there were two other judges with me. We had 700 entries that we needed to look at in one day. When I got to the judging at AIGA headquarters, I met with the other two jurors. One was a very well known designer who had a bit of a boutique agency, very posh. She was very stylish. I did not feel nearly as stylish. Another guy was there from Apple.

This was shortly after the iPod had been released and he was on his iPod the whole time and really didn’t spend a lot of time paying attention to the judging. In any case, this other juror –

Tim Ferriss: What a dick. Anyway; sorry, a guy I don’t know.

Debbie Millman: The other juror looks at me when I get there and she’s like, “Just so, you know, I don’t intend to have any mass market package in this competition get an award.” And I was like, okay. And I didn’t agree with that. I was working at a CPG package design firm and we had recently designed the Burger King logo, and the Star Wars Episode 2, Attack of the Clones merchandising and package, and the Hershey bar. So, you know, I was coming from a completely different point of view.

We ended up disagreeing so, vehemently that at one point I thought we were going to actually come to fist-a-cuffs.

Tim Ferriss: Was this behind the scenes or was this while you were on the panel?

Debbie Millman: This is while we’re on the panel and there’s somebody that’s trailing us, writing notes for an article that’s going to appear in the Annual. It was mortifying. In any case, we were only able to agree I think on seven things that would go into the competition journal. Which is not a way to encourage future applicants to apply for the competition. So, AIGA was not particularly happy with us. This fellow juror of mine hated me. And I felt, at the end of that day, that I would never, ever be asked to do anything with AIGIA ever again.

I remember walking back to my office, which was at the Empire State Building at the time, it was dusk and I feel like oh, this is never, ever going to work out and resigned myself to that. Rick asked for some work of mine to be included in the journal as evidence of my credentials for being a juror, and the two biggest projects that I had done at the time were the Burger King identity and the Star Wars identity.

And so, I sent those in as my credentials. They were presented in the journal and that was the end of that, or so, I thought. May 2nd, 2003, I get a link from a friend of mine. She sends me an email and she’s like: read this in the privacy of your own home, preferably with a big drink.

Tim Ferriss: Oh, boy. What a setup.

Debbie Millman: I know, right? And I am not one who likes surprises or anticipation. I need instant gratification. So, I don’t wait to go home. I don’t wait to get a drink. I click into the link at my desk in my office and come to a letter, an open letter to AIGA written by a designer named Felix Sockwell on this thing called “Speak Up.” And Speak Up was one of the first web logs, and the first design blog.

And the letter chastises AIGA for including me, Debbie Millman, as a juror in their annual competition, what is supposed to be the most prestigious competition in the country and accused me of not only being a corporate clown, but also, because of the work I do, they called me a she-devil.

Tim Ferriss: A she-devil! Wow.

Debbie Millman: And proceeded to take my entire career down. And it was a pile-on. Not only was the open letter quite harsh, but then there was the pile-on of comments that happened in the early days of blogging. Remember that?

Tim Ferriss: Oh, yes. I’m so, glad that hateful comments are a thing of the past. But yes, oh yes; intimately familiar.

Debbie Millman: This was before Twitter, right? And I’m reading this and my jaw is agape, and I am just in a state of catatonia. I couldn’t move. I was ashamed, embarrassed, terrified that people in my office would see it; that the reputation of the firm was being sullied by me. And I didn’t know what to do. I was despondent. I remember walking home from work that day, crying, thinking that I had to quit, I had to leave the design business and my career was over. This career that I had finally found for myself was now officially over.

I honestly did not know what to do, Tim. I felt like if I wrote in, that it would seem defensive; that it would bring more attention to this story. I felt that if I didn’t write in, I would be missing an opportunity to at least contribute to the conversation with a point of view that might be different from theirs.

I didn’t know what to do. And looking back on it now, I’m actually really ashamed of what I did because it was disingenuous. But at the time, it was the only thing that I felt I could do. So, a few days after the story broke and the comments piled in, I contributed and my first comment was – you’re not going to approve of this.

Tim Ferriss: We’ll see, we’ll see.

Debbie Millman: I wrote, “What a cool discussion. I love it.” I’m sorry. I’m so, sorry. You know, the book Cool Girl had not come out at that time but had it been out, I would have said, “That’s what I was trying to be; I was trying to be the cool girl. Nothing matters. I can eat five chili dogs and I don’t gain weight.” I’m quoting the book. So, yeah, I came in and that’s what I said.

But I ended up having the best possible back and forth I could muster. I tried to talk about how we had constructed the Burger King logo and the amount of testing we had done around the world, that how consumers really seemed to like it and who were they to declare that it wasn’t worthy? I tried to be as open and as defenseless as possible. Ultimately, they continued to pile on some more insults, and made fun of the practice that I had.

Then, a couple of people weighed in otherwise and the final comment was from a man named David Weinburg, who I’ve since become friends with as well who at the time worked at Landor.

Tim Ferriss: What is Landor?

Debbie Millman: Landor is one of the world’s biggest and most respected brand consultancies, started by Walter Landor about 80 or 90 years ago. He wrote in: “Let’s see what Felix can do with that Burger King logo, and great work over there at Sterling.” And that was sort of the end of that conversation. Nobody else came in with another comment. And what I thought was over really wasn’t.

Tim Ferriss: Felix is…?

Debbie Millman: He was the original writer of this open letter, Felix Sockwell, the illustrator and designer.

Tim Ferriss: Got it.

Debbie Millman: I thought it was over. I thought it had ended with some sort of a compromise in viewpoints. But to my chagrin, the writers at Speak Up kept writing about me. And the next article was called “Is the Dark Side Prevailing?”

Tim Ferriss: So, subtle.

Debbie Millman: Very subtle. At that point, Tim, I was obsessed. I was going to the site 15, 20 times a day.

Tim Ferriss: Oh, no.

Debbie Millman: Constantly refreshing, seeing what they were writing about me. And finally, I gave up and went to my IT person and said put parental controls on my computer at work; I don’t want to be able to see this site. And he did.

Tim Ferriss: Sometimes you need a helpful pair of handcuffs.

Debbie Millman: Well said. But I’d still go home and I’d look, but whatever. A couple of weeks later, the founder of Speak Up, a young man about 23 years old named Armand Vitt reached out to me. He wrote me an email and he apologized. He didn’t apologize for calling my work a pair of turds, which is what he did.

Tim Ferriss: I didn’t realize turds came in pairs. Shows what I know.

Debbie Millman: Ah, youth. So, he apologized for the bullying and for the unprofessional way in which the conversation ensued.

He made it very clear that he still thought my work was a pair of turds. But he didn’t feel that it was right the way that I had been spoken to.

I took a lot of care in responding to him. I accepted his apology. But at the time, I was really fascinated by this whole blogging thing. It was really interesting to me, this sort of real-time communication, holding people accountable. And I wrote him this sort of diatribe about it. He responded and said, “Would you like to write for the site?” And I was like: whoa, didn’t expect that one. So, I said yes, and I started writing for Speak Up.

Tim Ferriss: The Darth Vader column.

Debbie Millman: Well, what was so, interesting about the experience, Tim, was what the Speak Uppers were calling the “precious design word,” the AIGA world, they had already rejected me. And now the renegades, the anti-AIGA contingent, they were rejecting me.

So, at that moment, I actually felt like the most hated woman in graphic design.

Tim Ferriss: Masterless samurai, where to?

Debbie Millman: Exactly. So, what happened after that, it was really surreal. And this is why I say that what felt like at the time in May of 2003 to be the lowest point of my professional career actually became the catalyst upon which everything else has been built. So, I started writing for Speak Up, and all of a sudden I started to have that sense of what I had been originally searching for. In my efforts with Speak Up, I felt like I was part of something bigger than myself.

I felt like I was part of this sort of renegade group of misfits that were trying to change the world through graphic design criticism and online conversations. We all decided that year, in the fall of 2003, that we were going to go as a group of gorilla Speak Up writers to the upcoming AIGA annual conference in Vancouver.

And we were going to give out this little brochure that Armand had put together called “Stop Being Sheep,” which was a riff on the great typographer Eric Spiekermann’s book Stop Stealing Sheep, which is about letter spacing. You know, thin slicing here to the very best of our ability. So, we went with this little brochure to the conference.

Tim Ferriss: So, these people then ended up accepting you, the people who had previously vilified you?

Debbie Millman: The people who had previously vilified me not only accepted me but over the years, Armand and his wife Brianny and I have become such good friends that I am now the godmother to their eldest daughter.

Tim Ferriss: Wow.

Debbie Millman: So, sort of similar to that Robert Edelstein story back when I was in college where he rejected me, or what I thought was a rejection of me, then ultimately became one of my lifelong friendships.

And now Armand and Brianny are also, family at this point, family.

Tim Ferriss: Amazing. I interrupted, though. So, you’re en route with this group of heretics and a pile of brochures or pamphlets.

Debbie Millman: Right, because brochures changed the world; you know that. And I’m sitting next to people who were also… There was at that time one direct flight from New York to Vancouver. The flight is filled with design luminaries, Michael Berube and Paula Share. I’m sitting next to a woman who is beautiful and elegant, and I’m wearing sweat pants and carrying a bag of McDonald’s breakfast. And the only people that like the way McDonald’s breakfasts smell are the people eating it, not the people smelling it.

Tim Ferriss: True fact.

Debbie Millman: I don’t know why I didn’t think I would see people that I knew on this flight. Well, in any case.

So, I start talking to this woman next to me, and it turns out she’s going to the conference, as well. I ask her what she does, she says she’s a writer at Print magazine. I tell her about Speak Up. She’s all interested in what we’re doing. I tell her that we’re having this get-together, this party over the course of the conference; I’d like to invite her. She gives me her card. Without looking at it, I put it into my bag. We talked through a couple of hours and then we went off into our own thing; whatever else we were doing on the flight.

When I get to my room in Vancouver, I take her card out of my bag and I see that she’s the Editor in Chief, Joyce Redder Kay. I invite her to the party; she comes. We start a correspondence. I harbored this hope that maybe I could write for Print magazine one day. A couple of months later, she writes me and asks me if I want to participate in something she’s putting together for the upcoming HOW conference the next year in San Diego.

At the time, reality TV had just sort of burgeoned into culture, and there was a very popular TV show called Iron Chef about cooking in real time, and the audience voting. She wanted to do a riff on that called Ironic Chef, where three designers would create work on stage in real time and the audience would vote. This to me sounded like the definition of hell.

Tim Ferriss: And just to clarify for people, Print magazine is actually called Print magazine.

Debbie Millman: It is called Print magazine. It’s the oldest graphic design magazine in the country; it’s 75 years old. It has won I think five national design awards, general excellence awards. Not national design awards; I’m sorry. Magazine awards, which is the highest honor; an Effie, I believe it’s called, that a magazine can win.

It’s a remarkable magazine and I had this dream of someday writing something for it.

Tim Ferriss: So, Ironic Chef.

Debbie Millman: Yes, Ironic Chef.

Tim Ferriss: Debbie Millman’s personal version of hell.

Debbie Millman: Yes. And I’m afraid to say no. I feel like if I say no, I’m never going to be offered an opportunity to do anything with Joyce again. So, I say yes, and I’m further humiliated when I get to San Diego when I realize that I have to wear a chef’s outfit on stage. There are pictures of this by the way; I’m not lying or exaggerating. So, I go through with this. I’m on stage with the emcee, Steve Heller, who I had never met.

Steve Heller is one of the world’s foremost design critics. He was the art director of the New York Times book review for 30 years. He started numerous programs at the School of Visual Arts, graduate programs and he’s written about 170 books about design and graphic designers.

He is the judge. I am terribly intimidated because he is Steve Heller, one of the greatest people who has ever lived. And there are three of us. I come in second, which is not terrible. I don’t win but I don’t lose. And in another abhorrent moment of courage, I ask Steve, because he was nice to me that day, if he would like to have lunch in New York City when we were back. He lived in New York City as well. He agrees. We go to lunch.

I was so, intimidated, I had a cheat sheet I had prepared on topics in which I could discuss with Steve. I wrote it on a paper napkin, put it in my lap and I could refer to it if I choked and knew not what to say next. In any case, I had some book ideas. Steve told me they were both bad. I went away a little bit discouraged but still happy that I had met him, and he told me I’d get a book; just be patient.

Four months later, a publisher calls at the recommendation of Steven Heller with a book that he had turned down. They had wanted him to write with the horrific title, How to Think Like a Great Graphic Designer. Once again, I think if I don’t say yes to this, I’m never going to be asked for anything again and I take on this book. But I ask them if I can do it in a different way because I didn’t believe there was just one way for a great graphic designer to think.

There are a myriad of ways, and could I interview great graphic designers and reveal how they think? They agreed, and that became my first book. In the meantime, Joyce Redder Kay, the editor of Print magazine, reaches out and asks me if I would like to write a review about Wally Owens’ then upcoming book on branding. I agree. I write my first piece for Print magazine that year, and I’ve written for every single issue since.

Tim Ferriss: Wow.

Debbie Millman: 13 years later, two years ago, I was appointed the Editorial and Creative Director of Print magazine.

Tim Ferriss: Well, it seems like those brochures did play a role.

Debbie Millman: And that’s just the start of it, Tim. If it weren’t for Speak Up and that story, I was then contacted by a fledgling internet radio network called Voice America in 2004, shortly after a piece that Mark Kingsley and I wrote about election graphics that kind of went viral. They wanted me to host a show about branding. I was worried that if I said no, I’d never get another opportunity again and asked if I could sort of do it about branding, but maybe do it more about design and pitched this idea to them about Design Matters, a radio network show.

They said yes. Just when I was beginning to think oh, I might get rich from this, they told me that I needed to pay them for the air time.

Tim Ferriss: Surprise. Another surprise.

Debbie Millman: But I was really excited about this. At that time, everything I was doing was very commercially driven and felt that this would be a way for me to talk about graphic design and engage with people in a way that had no commercial value whatsoever and was just all about how to satisfy our creative souls. And that’s how Design Matters was born. My podcast was born on this sort of Wayne’s World-esque internet radio network called Voice America.

I did the show for four years on Voice America; paid them for four years to do it and then brought the show to Design Observer. Bill Drenttel, the late, great Bill Drenttel, the founder of Design Observer, invited me to bring the show over to Design Observer in 2009 with the proviso, that I improve my sound quality. I was doing my show with two handsets.

Have you ever had a conversation with two people on the same phone line in your house, and you’re on different handsets in different parts of the house, and the echo and all of that?

Tim Ferriss: Oh, yeah.

Debbie Millman: Those were my early shows. But I had no idea what I was doing. There was no podcast when I started. I started to upload my show to iTunes just for the kick of it; just to be able to share it. Now, 12 years later, in three weeks I’m going to have my 12th anniversary of Design Matters.

Tim Ferriss: Amazing.

Debbie Millman: We won a Cooper Hewitt National Design Award in 2009. At the end of 2015, iTunes – and you know this because you’re always on the list but after 11 years, iTunes designated it one of the best podcasts on iTunes. I’ve transitioned the show from a show about why design matters to a show about how creative people design their lives and the trajectory that people take. Even from this conversation, you can probably tell how interested I am in how people make their lives; the choices they make and how they live, and what they dream about and what they become.

That’s the direction that the show has taken. And I’m about to approach my 300th episode.

Tim Ferriss: Congratulations. That’s a huge milestone. And you being interested in the way that you are, and with the intensity that you are interested, I think is very well reflected in the episodes themselves. We’ve spent some time in your studio. It is one of the most lovely and engaging conversations I’ve ever had in interview format. It was such a relaxed and fun experience for me, which is not the norm as you now. So, I certainly recommend everyone check out Design Matters.

But I want to talk about some of your decisions, and specifically we could talk for 20 hours but I want to talk about a name that I had not heard in my life until very recently; Milton Glaser.

Debbie Millman: Yes.

Tim Ferriss: As you mentioned, you had done brand makeovers or branding for Burger King, Star Wars, Hershey’s, Tropicana, I think was there?

Debbie Millman: Yes, Tropicana.

Tim Ferriss: And tell me if I’m getting this wrong but at one point, if you walked into any grocery store or supermarket, etc., you a hand in 20 percent of everything that you saw; something like that.

Debbie Millman: Isn’t that crazy?

Tim Ferriss: It’s nuts.

Debbie Millman: Yes, it is.

Tim Ferriss: That’s mind blowing when you consider the number of different products, the SKUs. And for people who are wondering what CPG is, it’s Consumer Packaged Goods. So, at some point your hand was involved in just an incredible array and plentitude of different products.

How did Milton Glaser enter the scene? And could you describe for people who he is?

Debbie Millman: Milton Glaser is the elder statesman of the design world, and is certainly one of – if not the – greatest living graphic designers. He’s in his 80s. He is responsible for the iHeart New York logo. He did that iconic Bob Dylan poster of Bob Dylan in profile with the streams of colorful hair. He is one of the founders of New York magazine. He has had more impact and created some of the most memorable, well known, and iconic brands and identities in the world.

My relationship with Milton really began when I took a class of his at the School of Visual Arts, a summer-intensive in the summer of 2005.

I had already interviewed him for Design Matters, but it was over the phone and while I cherish that interview, it was one of my very, very early interviews so, I’m somewhat gun shy to send people to listen to that one because it’s so, early in my journey as a podcaster.

But in any case, I took this class with him. And that class, it’s interesting how we started the show talking about my 8-year-old drawing, and you talking about your friend who had written this essay that then predicted his life. Milton taught this summer-intensive I think for about 40 or 50 years, and he used to say it was one of the most important things that he did. He’s not teaching it anymore. He had us do an exercise in that class where we had to envision the life that we could have if we pursued everything that we wanted with the certainty that whatever it is that we wanted, we would succeed.

I wrote an essay in July of 2005. It was supposed to be a five-year plan. He asked us to dream big, and not to edit and said that it had a bit of a magical quality that he experienced with his students over and over so, to be careful what we wished for. I created this essay with these long ranging, far fetched goals that I can tell you now, 12 years later, have almost all come true. It is spooky, spooky. And so, that’s an exercise I do now with my students. Milton has had one of the most profound impacts on my life, aside from the profound impact he’s had on the world. I feel really, really lucky that I have been a student of his and have gotten to interview him now numerous times.

And I feel that my relationship with him is certainly one of the luckiest things that has ever happened to me.

Tim Ferriss: Can you describe the exercise as you do it with your students now?

Debbie Millman: I teach undergrad and graduate classes at the School of Visual Arts. I run a master’s in branding program at the School of Visual Arts, which I was given this opportunity via Steve Heller, who I again would not have met had that whole Speak Up experience not happened. So, yet another thing. Every single thing that I’m doing now in my life, Tim, stems from that experience.

Tim Ferriss: Also, just to underscore another theme, he had in some sense, you could interpret it as rejected two of your book ideas, even though he was nice to you and went out to lunch with you. But now, later on down the line, you kept that relationship and it lands you at SVA.

Debbie Millman: Absolutely. Steve is one of the most generous and engaging people I have had the privilege of knowing. I often tease Steve and say that he’s my fairy godfather. Because he’s the only person in my life, or maybe one of two people in my life now, that I could say has just been – he has this sort of generosity that is all about: “Here, take this, do that; make this happen. This is for you,” with no strings, no ties, no obligations. It’s just pure generosity. He has done that over and over and over again for me since meeting him back in 2004. So, the exercise that I do now with my students, because they are quite a bit younger than I was when I was doing this five-year plan, I ask them to do a ten-year plan.

And so, this gives them a chance to really mature into who they are in their 20s and into their early ‘30s. And it’s this ten-year plan for what I call a remarkable life. It’s about imagining what your life could be if you could do anything you wanted without any fear of failure. And they are the most life affirming essays. They are so, full of hope and optimism and well being and goodness, that it gives me a sense that humanity can be saved. So, I borrowed that exercise from Milton and now use that both in my graduate program and the undergraduate classes that I teach.

Tim Ferriss: This is going to seem nerdy, but I’m a nerd and I’ll run with it. Do you have any parameters for people at home who might want to try this, or recommendations, ways to start? Is it bullets or is it in prose in full paragraphs? How does it end? Any recommendations for people who would like to give this a stab?

Debbie Millman: So, let’s say it is winter, 2027. What does your life look like? What are you doing? Where are you living? Who are you living with? Do you have pets? What kind of house are you in? is it an apartment? Are you in the city? Are you in the country? What does your furniture look like? What is your bed like? What are your sheets like? What kind of clothes do you wear? What kind of hair do you have? Tell me about your pets. Tell me about your significant other.

Do you have children? Do you have a car? Do you have a boat? Talk about your career. What do you want? What are you reading? What are you making?

What excites you? What is your health like? And write this day, this one day ten years from now. So, one day in the winter of 2027; what does your whole day look like? Start from the minute you wake up, brush your teeth, have your coffee or tea, all the way through until when you tuck yourself in at night. What is that day like for you? Dream big. Dream without any fear. Write it all down. You don’t have to share it with anyone other than yourself. Put your whole heart into it and write like there’s no tomorrow. Write like your life depends on it because it does. And then, read it once a year and see what happens. It’s magic. It’s magic, Tim.

Tim Ferriss: I love this. I need to do this. I’m not asking for some hypothetical listener. Listeners, I love you guys but this is also, for me.

Debbie Millman: It is astounding, and I do this now with all of my students. And I can’t begin to tell you how many letters I get from students from ten years ago, that are like, “Debbie, it all came true! How did this happen?” And I am so, thrilled that these things can make a difference. This goes back to the earlier part of our conversation about my own fears about what I could or would or should become. And the idea that at that same time in my life, that intersection on Bleaker Street and 65thy Avenue, peering deep into my future and not knowing that anything was possible for me.

To give somebody at that same stage in their life, or any stage, really but particularly at that vulnerable stage when you are so, worried about what you can and can’t become. To give somebody that sliver of a dream, of a hope that this could happen, and have them declare what they want I think is a remarkable exercise.

That ‘s why I call it “Your Ten-Year Plan for a Remarkable Life.”

Tim Ferriss: How long was your essay, and is there any consistency to length? Are there guidelines or is it as long as it takes? And some are two pages, some are 20 pages?

Debbie Millman: Some are two pages, some are 20 pages. I think the longer it is, the more likely it is to be affirmed, for some reason.

Tim Ferriss: In detail?

Debbie Millman: I find the more care you put into it, the more care and detail you put in. Oh, a doggy!

Tim Ferriss: Yeah, that’s a doggie. That’s my Molly. Sorry; she’s excited about this exercise. Please continue.

Debbie Millman: Clearly. I think the more care you put into it, likely the more success you’ll have coming out of it. Mine, I wrote in a journal that I was keeping at the time so, it was about 5 by 7.

It was probably about ten handwritten – big handwriting; I had big handwriting; ten big handwriting pages and it was the whole day. And then, because I was really excited about it and because I love lists, I made a list of everything that I wanted to come true.

Tim Ferriss: Well, I’ll tell you, I think that might be a good place to wrap up this part one, which I think we may have more conversations in us. I have so, many questions I’d still like to ask but I think that is giving people who have a primacy and recency bias; I want them to remember this exercise as one of the actionable recommendations they can certainly explore from this interview, and there’s so, much. But let me ask before I let you go, and I’ll ask where people can find you and so, on to learn more about your work.

But before that, is there any parting piece of advice or recommendation, question, anything that you’d like listeners to carry with them when they stop listening to this?

Debbie Millman: Well, let’s see. I recently went through a pretty major transition in my life. It was something that I had to make a pretty big decision about, and it was a somewhat prolonged, agonizing decision so, much so, that my friends and loved ones were no longer listening to my machinations in making the decision because they thought I never was going to actually make the decision.

And so, I can share that, because I do think on the other side of that decision now is an important realization that I think can help people. I’ve had a full-time job since I graduated college. And the last 22 years, I was working at a branding consultancy, as I mentioned, called Sterling Brands. And I had been very luck to be able to sell the company that I was a part of and ultimately a partner in after about 13 years of working there.

So, in 2008, the two partners that I had, the man who originally hired me, Simon Williams, and then Austin McGee who is the third partner to come in after me, we sold our company to OmniComm.

At the time, I had been offered this opportunity with Steve Heller to start the Master’s in Branding program at the School of Visual Arts and organized my time so, that my day job at Sterling Brands wouldn’t be impacted by what I was going to be doing at SVA, which was made possible by starting my branding program as an evening program. So, I had two full-time jobs; a day job at Sterling and my night job at SVA.

Most people thought I would go through my earn-out at Sterling, and then leave and transition to working at SVA and doing all of the personal projects that I had been talking about for so, long about doing. So, the five years happened, and we had a really wonderful, successful earn-out so, there was no excuse for me, Tim, to continue on this same path and it was time to make that change. The last thing I wanted was to end up like the characters in Revolutionary Road, that remarkable book where people talk about making these changes their whole lives and then never, ever do. But I became terrified.

I became terrified that if I made this change, that I would not have financial stability anymore, that I would not be able to fulfill all of the dreams that I had and would have to confront that. And so, five years turned into six years, and six years turned into seven years. And just at a point where I was starting to think about really doing it, sort of like Al Pacino in Godfather 3, I was offered an opportunity to take over as CEO of the company. Simon Williams, the then CEO was looking to become chairman and needed to appoint a new CEO and he came to me and asked me if I wanted the job.

And here it was. This was the big decision of a life. Do I become the CEO and have this amazing continuation of money and career and security and everything else that is conventionally approved of, or do I say no, actually, I am not going to double down; I’m going to live the way in which I have been saying I wanted to with more freedom and more opportunity to do more personal projects, and pro bono projects, and give back.

And I had to decide. It took me four months to decide. Simon Williams finally said to me, “Debbie, anything that takes you four months to decide probably means you don’t want to do it.” And it was the hardest decision of my life but I turned it down. I turned the CEO job down. And then, two things happened.

First of all, one of the things that I realized is that I was in this trapeze. And rather than just let go of the trapeze and do something else, I had every single crook of my body holding onto some other trapeze. And that there was this sense of if I am not doing enough, I am not worthy.

If I am not making enough, I am not worthy. If I am not producing enough, I am not worthy. And suddenly, I had to not just let go of the trapeze but let go of the entire apparatus. I have realized now two things. One, most people live in a world of scarcity. We think that all we have now is all we will ever have, and if we give something up, we will just have less.

What ends up happening is that we don’t think about all the possibilities of things that could come up if we give ourselves openings to receive them. And so, now, as opposed to having less than I thought, I have way more because I have all these new things that I’m doing that I never would have thought possible.

Second, that hard decisions are only hard when you’re in the process of making them. Once you make them, they’re not hard anymore. Then it’s just life and freedom. And it’s an extraordinary experience that I really would like to share with your listeners, with our listeners.

Tim Ferriss: It’s such an important discussion on many levels. I think it’s worth repeating a few things, and certainly this echoes in my experience, as well. One, that agonizing over the decision is often harder than whatever the outcome of the decision will be. And for that matter, in many cases, not all but in many cases if you make a decision and you decide that it’s not the right decision for you, you can quit. You can do something else. It’s not a permanent sentence, necessarily.

And also, this is something that I’ve had to learn and relearn many times in my life, which is if it’s taking you that long to make a decision, you probably don’t and shouldn’t – don’t want to and shouldn’t do whatever it is that you’re agonizing over with pro and con lists, trying to justify in some fashion.

And both of those points I think are so, so, important.

Debbie Millman: I also, think that if you’re waiting for something to feel right before you do it, if you’re waiting for a sense of security or confidence, that those things are sort of like being on a hedonistic treadmill. If you think you need enough of this before you do that, when you achieve whatever that is you think you need, you’re going to then up the ante and you’re never, ever going to be satisfied with whatever it is you think you need before you do something, if it’s not something that is real.

So, if you think oh, I need this much money before I do this, when you get that much money then you’re going to realize oh, I actually think I need this much more. And it’s just going to be this carrot in front of you that you’re agonizing over trying to reach.

And then the other thing is, and I’m going to quote Dani Shapiro here, the great writer Dani Shapiro.

I asked her once about confidence and she said that “confidence is highly, highly overrated and that most confident people, or overconfident people, tend to be kind of annoying.” She said what she felt was more important than confidence was courage, and I fully, fully agree; taking that first step. Confidence really only comes from repeated attempts at doing something successfully.

But in order to take that first step you need courage, and that’s much more important than confidence. So, for anybody who’s waiting for the confidence to show up, take the first step in a moment of courage, even if it’s aberrant courage, to come full circle in this conversation.

Tim Ferriss: Such good advice. It reminds me of something that the brother, Kamal Ravikant, of another friend of mine, Naval Ravikant, told me. Naval is a very, very successful entrepreneur and investor, among other things; very, very good writer, as well, as is his brother Kamal who just had a novel come out.

Naval said to his brother, “If I always did what I was qualified to do, I would be pushing a broom somewhere.”

Debbie Millman: Well said.

Tim Ferriss: I thought that was very, very encouraging.

Debbie Millman: Touche!

Tim Ferriss: Debbie, I have so, much fun every time we get to spend time together. Where can people find out more about you? Where can they learn more about your work? Where would you like people to say hello on social, if that and I’ll put all of this in the show notes for everybody listening, of course.

Debbie Millman: Sure, absolutely. I’m Debbie Millman on Twitter and Instagram. You can see more about my program at the School of Visual Arts at, and where you can listen to all my podcasts, and see my visual essays, and my books and so, on.

Tim Ferriss: For people who would be novices or new entrants into the world of, say, graphic design, recognizing that your podcast is about a lot more than that, which episode or episodes would you suggest they start with?

Debbie Millman: I would suggest that they start with Chris Ware. He is an extraordinary graphic novelist. It’s one of my most favorite episodes that I’ve ever conducted.

Tim Ferriss: How do you spell his last name?

Debbie Millman: W-A-R-E. From there, some of my favorite episodes over the last year, aside from my episode with you which I cherish, my episodes with Amanda Palmer, my episode with Allain de Botton, my episode with Krista Tippett, Nico Muhly, the great composer. Those are all episodes in the last year that I’m most proud of.

Tim Ferriss: Wonderful. Debbie, you’re a rock star. Thank you so, much for the time.

Debbie Millman: Oh, Tim. Thank you, thank you.

Tim Ferriss: I really appreciate it. And to everybody listening, as always you can find show notes, links to resources, all sorts of of things that we talked about and maybe more at And until next time, thank you for listening.

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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2 Replies to “The Tim Ferriss Show Transcripts: Debbie Millman (#214)”

  1. Listened the first time, and listened to the repost. This is one of the best interviews ever. This should be on my rotation to listen to quarterly if not more often. So valuable. Thank you.