Debbie Millman Interview | The Tim Ferriss Show (Podcast) | Transcription

Transcription for the video titled "Debbie Millman Interview | The Tim Ferriss Show (Podcast)".


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Intro (00:00)

This episode is brought to you by FreshBooks. Back in 2003, a busy freelancer named Mike McDermott, who I've actually had dinner with, accidentally saved over an invoice and lost all of his work. To make sure that never happened again, Mike set out to create FreshBooks, which is now the number one cloud accounting software designed exclusively for self-employed professionals around the world that is used by now 10 million plus folks in total who need to send invoices, get paid fast, and track their time. A lot of you fall in that category. In September of this year, Mike and his entire team relaunched an all new version of their platform built from the ground up, doubled down on what made a great in the first place, namely simplicity and speed. So I can't cover all the features in this particular sponsor read, but you can send a branded invoice in under 30 seconds. You can see when a client has looked at their invoice, and you can enable online payments in two clicks. If you need customer support, you will get a real human being on the phone in three rings or less. And there are many other things you can do. You can take pictures of receipts on your phone using their iOS mobile app and make expenses a million times easier, et cetera, et cetera. It is a rad service. A lot of you have recommended it to me. That's how this came to be as a sponsorship. So to claim your 30-day unrestricted free trial, that means no credit card needed. And see how the brand new FreshBooks can change your freelancing game. Go to and enter Tim, T-I-M in the How Did You Hear About a Section? That is This episode is brought to you by Wealthfront. And this is a very unique sponsor. Wealthfront is a massively disruptive, in a good way. Set it and forget it investing service, led by technologists from places like Apple and world famous investors. It has exploded in popularity in the last two years, and they now have more than $2.5 billion under management. In fact, some of my very good friends, investors in Silicon Valley have millions of their own money in Wealthfront. So the question is why? Why is it so popular? Why is it unique? Because you can get services previously reserved for the ultra wealthy, but only pay pennies on the dollar for them. And this is because they use smarter software instead of retail locations, bloated sales teams, et cetera. And I'll come back to that in a second. I suggest you check out Take the risk assessment quiz, which only takes two to five minutes, and they'll show you four free exactly the portfolio they'd put you in. And if you just want to take their advice, run with it, do it yourself, you can do that. Or as I would, you can set it and forget it. And here's why. The value of Wealthfront is in the automation of habits and strategies that investors should be using on a regular basis, but normally aren't. Great investing is a marathon, not a sprint, and little things that you may or may not be familiar with, like automatic tax loss harvesting, rebalancing your portfolio across more than 10 asset classes, and dividend reinvestment add up to very large amounts of money over longer periods of time. Wealthfront, as I mentioned since it's using software instead of retail locations, et cetera, can offer all of this at low costs that were previously completely impossible. Right off the bat, you never pay commissions or account fees. For everything they charge, 0.25% per year on assets above the first 15,000, which is managed for free if you use MyLink, That is less than $5 a month to invest a $30,000 account, for instance. Now, normally, when I have a sponsor on the show, it's because I use them and recommend them. In this case, it's a little different. I don't use Wealthfront yet because I'm not allowed to. Here's the deal. They wanted to sponsor this podcast, but because of SEC regulations, companies that invest your money are not allowed to use client testimonials, so I couldn't be a user and have them on the podcast. But I've been so impressed by Wealthfront that I've invested a significant amount of my own money, at least for me, in the team and the company itself. So I am an investor and hope to soon use it as a client. Now back to the recommendation. As a Tim Ferriss show listener, you'll get $15,000 managed for free if you decide to open an account, but just start with seeing the portfolio that they would suggest for you. Take two minutes, fill out their questionnaire at It's fast, it's free. There's no downside that I can think of. 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 advance, we cover some very, very deep, hard, and also sensitive material in this episode.

Understanding Debbie Millman: Her Life, Passions And Beliefs

Who is Debbie Millman? (04:47)

For some people who listen to this, it will be, I think, the most important podcast episode you ever listen to, and that has nothing to do with me. It has everything to do with the stories and lessons of Debbie Milman. @dibbmillman on Twitter and elsewhere, you can say hello, is, quote, "One of the most influential designers working today," end quote, by graphic design USA. She is also the founder and host of Design Matters, which is the world's first and longest-running podcast about design. She's interviewed nearly 300 design luminaries and cultural commentators, including Masimo 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 T-shirts, and if you've heard of, say, Star Wars, while she worked on the merchandising, Burger King, the redesign, Hershey's, Tropicana. At one point, if you walk into any given grocery store, or say supermarket, anything like that, she had a hand in about 20% 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 has authored, and in 2009, Debbie co-founded with Stephen 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, and 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 Milman. Debbie, welcome to the show. - Thank you, Tim. It's really wonderful to be here. - I have wanted to interview you on numerous occasions now over the last few years, so I'm thrilled that we are finally doing this, point number one. And I thought I would start with a question that someone like yourself who has explored so many different things and so many different formats, when someone asks you, what do you do? Let's say you meet someone at a party, they say, what do you do?

When someone asks you What do you do? (07:37)

What is your answer to that? - 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, and sometimes people look at me like, huh, like, huh? - I don't, too many hyphens, what does that mean? - Exactly. I found 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. - Executive's a great catch-all, you can use that. - Executive is a great catch-all. For a long time on Twitter, I had Debbie Millman as a girl until enough people said, Debbie really got to change that, and then I did. - Oh, the internet, well, you could put anything there, and I think about 10% of the people who come across will be outraged for one reason or another. - Oh yes, I 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. - 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.

The drawing at age 8 that predicted Debbies path (09:10)

- Oh, Tim, I learned that the hard way. - Well, I wanna talk about so many things, Debbie, but let's start with, and 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 eight years old. And so I know nothing about this, and I just want to start there, since it seems to make sense to begin at the beginning. - Well, I have a somewhat of a pack rat mentality. I keep things, I'm a sentimentalist at heart, and I like to keep things from all different stages of my life. And I have boxes of journals and drawings and all sorts of port cards, and you name it, I have it. Well, 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. - The Great Migration. - Yes. And before she moved, she unloaded several boxes of ephemera of mine that she had kept unbeknownst to me. And 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 eight years old. And after I admired my hand-to-work, 'cause I thought, "Wow, eight years old." I was like rocking the drawings. I realized that this particular drawing had predicted my whole life. And so I will explain this, I will try to explain this drawing as best as I can. And for some backstory, I am a native New Yorker. I was born in Brooklyn when I was about two 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 about, I was in the middle of a third grade and we moved to Staten Island. And I lived on Staten Island until I was in the fifth grade and to fifth grade, my parents got divorced. My mom took my brother and I, 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. And for some reason, I had a, I guess, a sense of what Manhattan looked like and felt like, probably from television. And at eight years old, I drew a picture of the streets of Manhattan. I'm walking, I'm a little girl, 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 quite in quite good detail. There were buildings and buses 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. And I not only labeled the delivery truck, I also drew the sign on the delivery truck. And the sign was Lay's potato chips. I drew the logo at eight years old. And when I saw this trying, 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 buses. And at the time I found this drawing, I was drawing logos for a living. And had I known that it would have been that easy just to follow that drawing, I would have saved decades of experiments in failure and rejection. - So this is fascinating to me for a number of reasons.

My considered young (pre-teen) predictions Id find in a barn (13:42)

I've had a few guests on the podcast. Chris Saka would be another example, was an investor. And he at some point wrote in journal, well, I think it was one of these composition notebooks with the sort of model black and white zebra/camoflush covers. - Oh, I love that. - 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 his, I think his parents' garage later around the age of 42 or something like that. And it also predicted effectively exactly what he would be doing. But it was lost in the slipstream and he took this very meandering, in some ways odd, seemingly fractured path to come right back to where he started in a sense. Did you then, 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 five, I knew I always wanted to be X. But what was your, or should I say, 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? - 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 not ever lived in Manhattan. And that was my big dream. And I came to Manhattan this 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. I, 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 was rather than paying the rent with the rent money that she was getting from us was keeping it and not paying the rent. So at the end of the summer, we all got evicted. - Surprise. - Yeah, I ended up appealing to the landlord to please, please help me find someplace else to live 'cause I really didn't have any place else to go. And 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 or afternoon delight depending on what they were doing and live 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 I knew that 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 Features 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 while 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, compuographic machines, stat cameras, and then when I graduated, was both doing freelance, editorial and freelance layout and paste up for the first couple of years of my career. - When did you start at the student newspaper?

Fragile eagerness, fear of rejection, and (hidden) determination (18:39)

Was that something you started at the very beginning and followed throughout your, I guess, undergrad experience? - 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 and 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, and he looked at me and asked me if I had any clips. And I was like, I didn't say what I was thinking but like hair clips, I didn't know what he was talking about. And 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 and 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 and I came up twice a week, Tuesdays and Fridays and I would, I was just enamored with this newspaper and I fantasized about writing really pithy area 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 then invite me to be a reporter and I sort of walk around like Rosalind Russell with a pencil behind my ear and my heels click clacking in the newsroom and of course that never happened. I never wrote one letter to the editor and for some reason in I guess an aberrant moment of courage I went back up to the newsroom, my second semester junior year and there was a women's uprising and the student wrote in the student health health food store and they were like, could you go cover that? And I was like, yeah, absolutely. And I went and did it and that was how I started writing for the paper, I then wrote a piece about an exhibit and the art center and by the end of my second semester junior year only because I think no one else would take it, I was offered the job of being editor of the arts and feature 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 something, I was part of something bigger than myself, I felt like I was, 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. - I wanna talk about that aberrant moment of courage and dig into that a bit. So you were rejected from or maybe rejected yourself or both initially when you approached the paper, then years later you have this aberrant moment of courage. What precipitated that? Was there a conversation, a realization, you watched a movie, what triggered that, do you remember? - I actually don't, I wish that I did it would make it from a much better story and certainly a better interview. But 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 forts 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, it takes me a while to recover. - Could you give any examples of that?

Giving your best effort and learning from experience. (23:08)

- I would say my entire life. I will give you 43 examples, get comfortable Tim. - I'm definitely settling in with my water, I'm ready to go. - Well, there I was rejected that first year of college 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. And 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 and 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 newspapers, I'm not 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, oh, I'm really enjoying this, but I don't really feel qualified to be doing this. Maybe I should go back to school and get a master's degree in journalism. And I lived in the neighborhood of a very good journalism school, the Columbia School of Journalism, and 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, you know, I want 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 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. And then I applied to the Whitney School, 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, you know, some good reviews, and 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-in sort of knitting my confidence or hoops and dreams together and then trying to do something else or trying again. - So a few questions. The first is what would you have, or 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? - 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 sort of 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 to 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. - And your clips mentioned, where you're like clips, hair clips reminded me of a story I heard when I was a student. So you work with a lot of students and we're gonna come back to that.

Ask for feedback and give yourself a chance. (29:02)

- Oh, Tim, can I add one more thing? - Of course. - I'm sorry, 'cause this is an interesting-- - You can add many things, please. - So one thing that I haven't shared about this particular story is that the man that, the young man that rejected me that first year is somebody that I have, that I then befriended in that experience of working at the paper that junior year. And 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 a very reasonable, 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 ever appropriate, that I was the one that rejected myself in many ways. One of the interesting things that I've found is, 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. - And I'd like to underscore this because it's such an important point.

Dont ascribe to malice what can be explained by incompetence. (31:19)

And I, in some respects, like you have been very sensitive. I still am in some respects, very sensitive. And my particular brand of that or my particular type of response is to feel a some type of sense of injustice. And so I will get rejected. And looking back at what I see as a rejection either, when I did this perhaps 10 years ago, I looked at a number of instances where I felt like I'd 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. - Yeah, absolutely. - So number one, no may just mean no, not right now. And you can even clarify that, right? You can ask that as a clarifying question. Number two 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. And that didn't cover it all for me though, but it really made it provide an impact on me when I was told this. And so I would read email with inserting, 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 10, that wasn't the tone at all. It was just, I was misreading it. And so I started to assume for myself, don't ascribe to malice what can be explained by incompetence or just busyness. The person is busy. If they send you a really short response to your mini novella of an email, it doesn't mean that they think you're worthless or not worth their time. It could just mean that they have 10 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 then they respond with, "Sorry kid, not right now." And you're like, "Really? That's it?" And then, yeah, I'm not gonna name names, but there's someone who, now I'm very close friends with, extremely well respected writer. And I got one of these one-line responses in 2005 or six when I sent an early manuscript for our work week to this person via email. And the response was, "effectively, thanks, but sorry, 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 scratch for years and now we're really good friends and the whole thing is ludicrous in retrospect. - One thing that I find about human nature is that ambiguity is always perceived negatively.

Our reaction to ambiguous comments. (34:13)

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. And so that's been something I've been struggling to overcome over the decades. So 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. So you mentioned clips, you had clips, hair clips. I was told this story by a professor in college about Nantucket Nectors when it was just getting started. And I believe two guys who are really faking it until they made it in a lot of respects. And at one point they're meeting with this distributor because they'd been selling these concoctions via boats in Nantucket from boat to boat to boat. And they wanted to go into retail and they met with this, it was either a retailer or a distributor, it was early on, and 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, they're like, what the hell is POS? Point of sale, which of course, you know, plenty about. But the, I wanted to, before we get to when you sort of first clicked into your niche and how that happened, you mentioned knowing that you wanted to be in Manhattan. And I've been thinking a lot about the components of, and this is a dangerous word sometimes, but happiness, and that oftentimes we think of the, let's say the journalist W's, right, the interrogatives, the why, the what, the where, and so on, of happiness. And I think humans tend to at least put why at the top, then maybe what's somewhere lower, and then where is often an afterthought. But I've started to believe that the where is more, is much more critical than we give it credit for, and that you can actually start there. So I've thought about this a lot for myself, but really the, how important the geography can be, because it determines in large measure who you're surrounded with all the time, and what you're surrounded with all the time. But I guess it's more of an observation than a question.

Components of happiness and wellbeing (37:45)

But how do you, if you've ever, if you think about that, how do you think about the components of happiness or well-being for yourself? - That's a big, big question, Tim. - Oh yeah. - Well, there's sort of two parts to the question, I think. And the first is this notion of New York sort of 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. And 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 Conde 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 high-altitude aspirations was either being an artist or being a writer, so being more of a fine 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-sufficiency. 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 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 in Sixth Avenue, and it suddenly occurred to me that I had to make a decision, and the decision was, what was I going to do? And 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 consider 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 easily become, or 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 and queens. I could have lived with friends and 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 X, Y, and Z, 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 walk-up. 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. I mean, 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 do 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 it was 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.

Where the desire for stability comes from (44:15)

- Oh, definitely. And so you've, by Hooker Crook, you're living in Manhattan. - Yes. - So that is the outcome in part of all of these decisions and the lead gene as you put it. Where does the need for stability, security or the desire for that come from? - Well, I do think that it's certainly in Maslow's hierarchy of needs, a really important one. For me, it takes on, I think, any, an extra level of significance in that I grew up in a really, really challenging environment. So my parents got divorced when I was very young.

Sometimes life can be brutal. (44:56)

I was about eight years old. And I had a very, very complicated relationship with my father. My father died last year unexpectedly. My father, sort of 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. And so 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. And so I had a lot of brutality in my life. And after they got divorced, I was 13. My father came back into my life. My mother then got involved with another man who was 10 years younger than her. So therefore only 10 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 like 18 years of my life, I lived in a state of constant terror and compensated or self-soothed, but with art, with a lot of extracurricular 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 from my life even back then. And 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, sort of Scarlett O'Hara. I'm never gonna go hungry again. Yeah, that doesn't always work out that way, but it was definitely the journey that I've been on. - Well, thank you for sharing that. I had no idea. - 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 I 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 Marischa Harkate and the Joyful Heart Foundation, which is a foundation that Marischa 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 that the very victim she was trying to find justice for 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 eradicate domestic violence, sexual assault and child abuse. And I've been working with Marischa and Miley Zambuto, the CEO of the foundation now for the last five years. And this work, I believe, the 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.

In-Depth Insights From Debbie'S Personal Experiences

The dark side of good food. (50:49)

And now dovetailing that with my own background really, truly makes me feel like my whole life makes sense, Tim. - That's beautiful. And 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. And 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? - 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. - What type of therapy is that? If you don't want me asking, I know very little about. - She, I think, well, she is 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 that 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. And it is enormously helpful to help me 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 is a lot of, 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 experiences that I had, 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, and 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. - Terrible. - And I believed that. I was a little girl. I believed that, and 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 wanna be the reason. I didn't wanna 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. And so for anybody that 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 that are there to help and listen and get you out of the situation that you are in. - Thank you for that.

Ending the Backlog to Change Culture (56:19)

To insert some levity, I'm not sure how to segue from here. But I will-- - Well, let's talk about some of the really, 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 JoyfulHeart 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 in shelves, in police departments, all over the country. And so the JoyfulHeartFoundation, 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 sort of rape culture that we're living in, but also the blaming of victims. So we can change culture by doing this work together. And it's something I'm super proud of. - And to those people 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 JoyfulHeartFoundation and so on at, all spelled out. Debbie would love to ask you to shift gears just a little bit, or perhaps a lot, the speak up story.

The Speak Up Story (57:47)

- That's one of my favorite stories. - All right. I will let you run with it. I would love for you to share. - Okay. So I wanna 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. So the year is 2003, and the time in the world was quite different than it is now. So we were online, but we weren't quite online in the way that we are now. I think YouTube was just, 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. And we were playing games and we were emailing and reading the news. And there were forums where people would congregate, but they tended to be more niche forums and not so much mainstream cultural forums. Prior to that, leading up to that time in my life, I had joined Sterling Brands in 1995. And 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. And 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, I had and my own sort of obsession with things like Lay's potato chips. - That's good saying that's potato chips. - Yeah, 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 that they chose. So I started working at Sterling Brands and had this heretofore unbelievable level of success financially. And 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. And in as much as I loved what I was doing and in as much 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 sort of part of my life that I felt was deeply missing. - At that point, what department were you working in?

Debbie's ups, downs and important learnings (01:01:43)

- I was working in marketing and sales. So 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 sort of story to share at some point. But 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 that 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. And I found the AIGA, the American Institute of Graphic Arts, and they had a special interest group within AIGA 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. And so I went and I volunteered and I became a member of AIGA and 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. And 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. And in that two years, I was very active. I went to all the meetings and we weren't funded by AIGA. We had a self-fund and so I made cupcakes for bake sales and we had a flea market and I was very, very involved in this 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. - Oh, you set me up with a cupcake. - Oh my God, I know. - Oh, they were really good cupcakes and brownies. And I was devastated. I was just devastated. And Rick Riffey, 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. And I think he felt really bad for me. He asked me if I wanted to have lunch and he took me to a very expensive lunch at 11 Madison and over the course of lunch. 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." And 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 curve by the special interest group of the brand experience. And this was like the biggest honor of my career at that point, to be a judge in the country's biggest design competition was I'm fathomable to me.

Debbies experience as an AIGA judge (01:05:14)

It felt like a miracle. And 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. And 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 and 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. - What a dick. - Yeah. - Anyway. - The other juror. - Sorry Guy, I don't know. - Yeah. - 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 packaging in this competition get an award." - Wow. - And I was like, "Oh, okay." And I didn't agree with that. I mean, I understandably had come, I was working at a CPG package design firm and we had recently designed the Burger King logo and the Star Wars episode two attack of the clones packaging and merchandising and the Hershey bar. And 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 gonna actually come to fisticuffs but we were only-- - Was this behind the scenes or is this while you're on the panel? - No, 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 juror of mine, the fellow juror, hated me and I felt at the end of that day that I would never ever be asked to do anything with AIGA ever again. And I remember walking back to my office, which was at the Empire State Building at the time, it was sort of dusk and I felt like, oh, this is never, ever gonna 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 printed 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.

The downside of being labeled a corporate clown (01:08:14)

She sends me an email and she's like, read this in the privacy of your own home preferably with a big drink. - Oh boy, what a setup. - I know, right? And I am not one that 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 blogs and the first design blog. And the letter chastises AIGA for including me, Debbie Milman, 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. - A she devil. - Wow. - And proceeded to take my entire career down and it was a pile on. So 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? - Oh, oh yes. - I'm so glad that hateful comments are a thing at the past. But yes, oh yes, intimately familiar. - This is important to win, right? - And I'm reading this and my jaw is a gape 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 a little bit different. I was in business and my career was over. This career that I had finally found for myself was now officially over. And 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, that I would be missing an opportunity to at least contribute to the conversation with a point of view that might be different than 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. And so a few days after the story broke and the comments piled in, I contributed. And my first comment was, and you're not gonna approve of this.

Debbie'S Professional Journey And Achievements

A different outcome in 2019 (01:11:24)

- Oh, we'll see, we'll see. - 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." You know? 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 and how consumers really seemed to like it and who were they to sort of declare that it wasn't worthy. And I tried to be as opened and as defenseless as possible. And ultimately they continued to pile on some more insults and made fun of the practice that I had and then a couple of people weighed in otherwise and the final comment was from a man named David Weinberg who I've since become friends with as well who at the time worked at Landor and Rodin. - Landor, what is it?

Landor (01:12:49)

- Landor is one of the world's biggest and most respected brand consultancies started by Walter Landor about eight or 90 years ago. And he wrote in, you know, let's see what Felix could 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 because the original writer of this open letter, Felix Awkwell, the illustrator. - Oh, my God, I got it. - And then I thought it was over. I thought it had ended with some sort of a compromise and 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? - So subtle, so subtle. - Very subtle.

Diatribes, Dark Money, and Darth Vader (01:13:50)

At that point, Tim, I was obsessed. I was going to this site 15, 20 times a day, constantly refreshing, seeing what they were writing about me and finally gave up and went to my IT person and said, put parental controls on my computer at work. I don't wanna be able to see this site. And he did. - Sometimes you need a helpful pair of handcuffs, yeah. - I will say. But I'd still go home and look, but whatever. A couple of weeks later, the founder of Speak Up, a young man, about 23 years old, named Armin 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 hit. - I didn't realize turds came in pairs. Shows what I know. - I think I used to. And so he apologized for the bullying and for the unprofessional way in which the conversation ensued as opposed to, 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. And 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 diet tribe about it. And he responded and said, well, would you like to write for the site? And I was like, whoa, didn't expect that one. And so I said, yes. And I started writing for Speak Up. And I said-- - The Darth Vader column. - Well, what was so interesting about the experience, Tim, was that the sort of what the Speak Upers were calling the precious design world, 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. - Masterless samurai, where to? - Exactly, exactly. So what happened after that was, 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. And 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.

Renegades in Vancouver (01:16:32)

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 sort of guerrilla Speak Up writers to the upcoming AIGA annual conference in Vancouver. And we were gonna give out this little brochure that Armin had put together called Stop Being Sheep, which was a riff on the great typographer, Eric Speakerman's book Stop Stealing Sheep, which is about letter spacing. You know, fin slicing here to the very best of our ability. And so we went with this little brochure and wrote to the conference. - And so these people then ended up accepting you. The people who had previously vilified you. You were-- - The people that had previously vilified me not only accepted me, but over the years Armin and his wife, Briany, and I have become such good friends that I am now the godmother to their eldest daughter. - Wow.

- 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 Armin and Briany are also family, at this point, family. - Amazing. - So I interrupted that you're on route with this group of heretics and a pile of brochures or pamphlets. - Right, 'cause brochures change the world, you know that. And I'm sitting next to people that are also, there was at that time one direct flight from New York to Vancouver. The flight is filled with design luminaries, Michael Beirut and Paula Cher, and I'm sitting next to a woman who is beautiful and elegant, and I'm wearing sweatpants and carrying a bag of McDonald's breakfast, you know, and the only people that like the way McDonald's breakfast smell of the people eating it, not the people smelling it. So, - Truth back to that story. - You know, I don't know why I didn't think that I would see people that I knew on this flight. But I was, well, in any case. So I start talking to this woman next to me and 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. She gives me, I tell her that we're having this get together, this party over the course of the conference. She's, I'd like to invite her. She gives me a card without looking at it. I put it into my bag. We talk through a couple of hours and then we go off into our own thing with, you know, 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 choice writer, K. I invite her to the party. She comes and we start a correspondence. I had this, I harbored this hope that maybe I could write for Print Magazine one day. And 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. And it's, at the time reality TV had just sort of burgined into culture. And there was a very popular TV show called Iron Chef about cooking in real time in the audience voting. And 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. And just to clarify for people, Print Magazine is actually called Print Magazine. It is called Print Magazine. It is called Print Magazine. It's the oldest graphic design magazine in the country. It's 75 years old. It has one, I think five national design awards, general excellence awards for the, not national design awards, I'm sorry, the magazine awards, which is the highest honor, an FE, I believe it's called, that a magazine can win. And it's a remarkable magazine. And I had this dream of someday writing something for it. - So Ironic Chef. - Yes, Ironic Chef. - Did he know that it's personal version of hell? - Yeah. And I'm afraid to say no. I feel like if I say no, I'm never gonna 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. I'm exaggerating. And so I go through with this. I am on stage with the MC Steve Heller, who I'd 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 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 that 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 aberrant moment of courage, I ask Steve, because he was nice to me that day, if you'd want 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 that I'd prepared of topics in which I could discuss with Steve, wrote it on a paper nap, can 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 that I'd get a book, just to be patient. Four months later, a publisher calls at the recommendation of Stephen 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 gonna be asked for anything again, and I take on this book, but I ask them if I could do it in a different way, because I didn't believe that there was just one way for a great graphic designer to think, there were myriad 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, writer Kay, the editor of "Print Magazine" reaches out and asks me if I'd like to write a review about Wally Olens' 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. - Wow. - 13 years later, two years ago, I was appointed the editorial and creative director of "Print Magazine."

Taking the opportunity to create and work on Design Matters (01:24:00)

- Well, it seems like those brochures did play a role. - And that's just the start of it, Tim. If it weren't for a speak up in 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 kinda went viral, and 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 pitch this idea to them about design matters, radio network show. They said yes, just when I was beginning to think, ooh, I might get rich from this. They told me that I needed to pay them for the airtime. - Surprise, another surprise. - But I was really excited about this, and 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 sort of our souls, 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 this show for four years on "Voice America," paid them for four years to do it, and then brought the show to design observer, Bill Drentell, the late, great Bill Drentell, 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.

Design Matters And Envisioning Future Aspirations

Debbie"s podcast debut and Design Matters (01:25:44)

You ever have 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? - Oh yeah. - 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. And now 12 years later, three weeks, I'm gonna have my 12th anniversary of Design Matters. We won a Cooper-Hueyewe National Design Award in 2009, the end of 2015 iTunes, and you know this 'cause you're always on the list, but after 11 years, iTunes designated it one of the best podcasts on iTunes. And 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. And even from this conversation, you can probably tell how interested I am in how people make their lives, the choices that they make and how they live and what they dream about and what they become. And so that's the direction that the show has taken. And I'm about to approach my 300th episode. - 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 it's very well reflected in the episodes themselves. And we've spent some time in your studio. - Yes. - And 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 know. 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.

The unlikely connections that led to a priceless friendship (01:27:56)

And as you'd mentioned, you'd done, I guess brand makeovers or branding for Burger King, Star Wars, I think you, Hershey's Tropicenna, I think it was-- - Yes, Tropicenna. - And tell me if I'm getting this wrong. But at one point, if you walked in any grocery store, supermarket, et cetera, you had a hand in, say, 20% of everything that you saw, something like that. - Isn't that crazy? - Yes. - It's nuts. - Yes, it is. - It's mind blowing when you consider the number of different products, right, the SKUs, and for people who are wondering what CPG is consumer packaged goods. And so at some point, your hand was involved in, just an incredible array and a multitude of different products. How did Milton Glaser enter the scene? And could you describe for people who he is? - Milton Glaser is the elder statesman of the design world and is the world's, certainly one of, if not the greatest living graphic designer. 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. The list goes on and on. He's 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, and I was somewhat, somewhat, 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 still a somewhat gun-shyed to send people to listen to that one 'cause it's so early in my journey as a podcaster. And that class, you know, it's interesting about how we started the show talking about my eight-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 that 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. And I wrote an essay in July of 2005. It was supposed to be a five-year plan. And 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. And 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 feel that my relationship with him is certainly one of the luckiest things that's ever happened to me.

An exercise to envision & claim your aspirations. (01:31:58)

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

Teaching the next generation to dream big (01:32:04)

Well, I teach undergrad and graduate classes at the School of Visual Arts. I run a masters 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 happen. So yet another thing, every single thing that I'm doing now in my life, Tim, stems from that experience. So just to underscore another theme, he had in some sense you could interpret it as rejected two of your book ideas, even though he's nice to you and went out to lunch with you. But now later on down the line, you kept that relationship and lands you at SVA. Absolutely. I mean, Steve is one of the most generous and engaging people. I have had the privilege of knowing. And 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. And he has done that over and 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're quite a bit younger than I was when I was doing this five-year essay, or a five-year plan, I asked them to do a 10-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 10-year plan for what I call a remarkable life. And 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. And so I've borrowed that exercise from Milton and now use that both in my graduate program and the undergraduate classes that I teach. This is going to seem nerdy, but I'm a nerd, so I'll run with it. And that is, do you have any parameters for people at home who might want to try this? Are recommendations ways to start? Is it bullets or is it pros and full paths? No, it's all paragraphs. How does it end? Any recommendations for people who would like to give this a stab? So let's say it is winter, 2027. What does your life look like? What are you doing? Who are you living with? Do you have pets? What kind of house are you in? Is it an apartment? Do 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? Do you have talk about your career? What do you want? What do 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 till 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. See what happens. I love this. I love this. I love this. 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. 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? I am so thrilled that these things can make a difference. And 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 in Sixth 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 or 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 tenure plan for a remarkable life. How long was your essay? And is there any consistency to length or their guidelines or as long as it takes? And summer, two pages, summer, 20 pages. Summer, two pages, summer, 20 pages. I think the longer it is, the more likely it is to be affirmed for some reason. I find them more carry put into it. The more Karen detail you put in. Oh, doggy. That's doggy. Yeah. That's my Molly star. She's excited about this exercise, please give me that. Yeah, clearly. I think that the more care you put into it, the more success you'll have coming at it. Mine was, I wrote it in a journal that I was keeping at the time, so it was about five by seven and 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. Well, I 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.

Sharing a major, life-altering decision that she recently made (01:39:24)

I have so many questions I'd still like to ask, but I think that is a given people have a primacy and recency bias. I want them to remember this exercise as one of the actionable recommendations that 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. Learn more about your work. And 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? Well, let's see. I recently went through a pretty major transition in my life. And 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 sort of machinations and making the decision because I thought that 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 was working. I've had a full-time job since I graduated college. And for the last 22 years, I was working at a branding consultancy, as I mentioned, called Sterling Brands, and had been very lucky 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 that originally hired me, Simon Williams, and then Austin McGee, who was the third partner to come in after me, we sold our company to Amni Kha. And 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. And most people thought that I would go through my earnout at Sterling and then leave and transition to working at SVA and doing all of the personal projects that I had been talking for so long about doing. And so the five years happened and we had a really wonderful successful earnout, so there was no excuse for me to continue on this same path and it was time to make that change. And 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 fill all 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 El Pacino and Godfather III, I was offered an opportunity to take over as CEO of the company. And Minnoleums, 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 is 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 am going to live the way in which I have been saying I wanted to with more freedom and more opportunity to do personal projects and pro bono projects and give back. And I had a decide. And 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 was 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 on to 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. And 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 were 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 what I thought, I have way more because I have all these new things that I am doing that I never would have thought possible. Second, that hard decisions are only hard when you are in the process of making them. Once you make them, they are not hard anymore. That it is just life and freedom. And it is an extraordinary experience that I really would like to share with your listeners, with our listeners. It is such an important discussion on many levels. And I think it is 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, if you make in many cases, not all, but in many cases, if you make a decision and you decide that it is not the right decision for you, you can quit. You can do something else. It is not a permanent sentence necessarily. And also, this is something that I have had to learn and relearn many times in my life, which is if it is 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 are agonizing over with pro and conless trying to justify in some fashion. And in both of those points, I think you are so, so important. I also think that if you are waiting for something to feel right before you do it, if you are 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 are going to then up the ante and you are never, ever going to be satisfied with whatever it is you think you need before you do something if it is 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 are going to realize, "Oh, I actually think I need this much more and it is just going to be this carrot in front of you that you are agonizing over trying to reach." And then the other thing is I am going to quote Danny Shapiro here, the great writer Danny Shapiro, if you are waiting for confidence and she, I asked her once about confidence and she said that confidence is highly, highly overrated and that most confident people or overly confident people tend to be kind of annoying.

On confidence vs. courage" (01:47:53)

And 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 is much more important than confidence. Anybody that is waiting for the confidence to show up, take the first step in a moment of courage, even if it is aberrant courage to come full circle in this conversation. Such good advice and it reminds me of something that the brother Kamal Ravakant of another friend of mine, Naval Ravakant, 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."

Closing Remarks And Contact Information

How Debbie feels about being a know it all (01:48:42)

I just had a novel come out, but Naval said to his brother, "If I always did what I was qualified to do, I would be pushing a broom somewhere." And I thought that was very, very encouraging. T-J. 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? Or do you like people to say hello and social if that? I'll put all of this in the show notes for everybody. 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 and so forth. For people who are not, 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? I would suggest that they start with Chris Ware. He is an extraordinary graphic novelist. It's one of the most favorite episodes that I've ever conducted. How do you spell his last name? 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 Alain de Bautin, my episode with Krista Tippett, Nico Mouli, the great composer. Those are all episodes in the last year that I'm most proud of. Wonderful.

Parting thoughts (01:50:47)

Debbie, you're a rock star. Thank you so much for the time. Thank you. Thank you. I really appreciate it and to everybody listening.

Where to find Debbie online (01:50:57)

As always, you can find show notes, links to resources, all sorts of things that we talked about and maybe more at Until next time, thank you for listening.

Tim's new email newsletter"Ç (01:51:09)

Hey guys, this is Tim again, just a few more things before you take off. Number one, this is "Fibollet Friday." Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And "Fibollet Friday" is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out. Just go to That's You'll get the email spelled out and just drop in your email and you'll get the very next one. And if you sign up, I hope you enjoy it.

This episode is brought to you byŒWealthfront, (01:52:11)

This episode is brought to you by Wealthfront. And this is a very unique sponsor. Wealthfront is a massively disruptive, in a good way, set it and forget it investing service led by technologists from places like Apple and world famous investors. It has exploded in popularity in the last two years and they now have more than $2.5 billion under management. In fact, some of my very good friends, investors in Silicon Valley have millions of their own money in Wealthfront. So the question is why? Why is it so popular? Why is it unique? Because you can get services previously reserved for the ultra wealthy but only pay pennies on the dollar for them. And this is because they use smarter software instead of retail locations, bloated sales teams, etc. And I'll come back to that in a second. I suggest you check out Take the risk assessment quiz which only takes two to five minutes and they'll show you four free exactly the portfolio they put you in. And if you just want to take their advice, run with it, do it yourself, you can do that. Or as I would, you can set it and forget it. And here's why. The value of Wealthfront is in the automation of habits and strategies that investors should be using on a regular basis but normally aren't. Great investing is a marathon, not a sprint and little things that you may or may not be familiar with like automatic tax loss harvesting, rebalancing your portfolio across more than ten asset classes and dividend reinvestment add up to very large amounts of money over longer periods of time. Wealthfront, as I mentioned since it's using software instead of retail locations, etc., can offer all of this at low costs that were previously completely impossible. Right off the bat, you never pay commissions or account fees. For everything they charge, 0.25% per year on assets above the first 15,000 which is managed for free if you use MyLink, That is less than $5 a month to invest a $30,000 account, for instance. Now normally when I have a sponsor on the show, it's because I use them and recommend them. In this case, it's a little different. I don't use Wealthfront yet because I'm not allowed to. Here's the deal. They wanted to sponsor this podcast but because of SEC regulations, companies that invest your money are not allowed to use client testimonials so I couldn't be a user and have them on the podcast. But, I've been so impressed by Wealthfront that I've invested a significant amount of my own money, at least for me, in the team and the company itself. So I am an investor and hope to soon use it as a client. Now back to the recommendation. As a Tim Ferriss show listener, you'll get $15,000 managed for free if you decide to open an account. But just start with seeing the portfolio that they would suggest for you. Take two minutes, fill out their questionnaire at It's fast, it's free.

Sponsors And Credits

This episode is brought to you by FreshBooks. (01:54:47)

There's no downside that I can think of. This episode is brought to you by FreshBooks. Back in 2003, a busy freelancer named Mike McDermott, who I've actually had dinner with, accidentally saved over an invoice and lost all of his work. To make sure that never happened again, Mike set out to create FreshBooks, which is now the number one cloud accounting software designed exclusively for self-employed professionals around the world that is used by now 10 million plus folks in total who need to send invoices, who paid fast and track their time. A lot of you fall in that category. In September of this year, Mike and his entire team relaunched an all new version of their platform built from the ground up, doubled down on what made a great and first place, namely simplicity and speed. So I can't cover all the features in this particular sponsor read, but you can set a branded invoice in under 30 seconds. You can see when a client has looked at their invoice and you can enable online payments in two clicks. If you need customer support, you will get a real human being on the phone in three rings or less. And there are many other things you can do. Take pictures of receipts on your phone using their iOS mobile app and make expenses and many types easier, etc, etc. It is a rad service. A lot of you have recommended to me. That's how this came to be as a sponsorship. So to claim your 30-day unrestricted free trial, that means no credit card needed and see how the brand new FreshBooks can change your freelancing game, go to and enter "tim", T-I-M in the "How Did You Hear About?" section. That is

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