The Tim Ferriss Show - #750: Neil Gaiman and Debbie Millman

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Starting point is 00:04:20 Tim, and code Tim, T-I-M, to get $350 off the Pod 4 Ultra. They currently ship to the United States, Canada, the United over metal endoskeleton. The Tim Ferriss Show. Hello boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of The Tim Ferriss Show, where it is my job to sit down with world-class performers from every field imaginable to tease out the habits, routines, favorite books, and so on that you can apply and test in your own lives. This episode is a two-for-one, and that's because the podcast

Starting point is 00:05:15 recently hit its 10th year anniversary, which is insane to think about, and passed 1 billion downloads. To celebrate, I've curated some of the best of the best, some of my favorites from more than 700 episodes over the last decade. I could not be more excited to give you these super combo episodes. And internally, we've been calling these the super combo episodes because my goal is to encourage you to, yes, enjoy the household names, the super famous folks, but to also introduce you to lesser known people I consider stars. These are people who have transformed my life and I feel like they can do the same for many of you. Perhaps they got lost in a busy news cycle. Perhaps you missed an episode.

Starting point is 00:05:57 Just trust me on this one. We went to great pains to put these pairings together. And for the bios of all guests, you can find that and more at Tim.blog slash combo. And now, without further ado, please enjoy, and thank you for listening. First up, Neil Gaiman, best-selling author and creator of books, graphic novels, short stories, film, and television for all ages, including Neverwhere, Coraline, The Graveyard Book, The Ocean at the End of the Lane, The View from the Cheap Seats, and The Sandman series of graphic novels. You can find Neil on Instagram at Neil himself. Back in about 1997, I read an article by Ian Fleming, who wrote the James Bond books, about how he wrote the James Bond books. And you read this article and you realize something, which is Ian Fleming did not enjoy the process of writing. I was always fascinated by the fact that several of Roald Dahl's

Starting point is 00:07:07 most famous short stories were plotted by Ian Fleming. Ian Fleming would... Really? Yeah, he gave Dahl... I had no idea. The two best short story twists, which are Lamb to the Slaughter, where the woman kills her husband with a leg of lamb and then cooks it and feeds it to the slaughter where the woman kills her husband with a leg of lamb and then cooks it and feeds it to the detective who is going, I cannot figure out what he was hit with, is an Ian Fleming plot.

Starting point is 00:07:33 And so is the one about the evil antique dealer who finds this amazing antique on some farm and decides to cheat the farmers and explains that, well, the thing isn't worth any money, but the legs, the legs are worth some money. So I'll give you, you know, 20 quid for the legs and is about to take away this million pound antique thing. And the farmers helpfully rip off the legs and throw the rest of it away. They make this easier for you. And those plots were both Ian Fleming's.

Starting point is 00:08:05 And you start realizing, ah, you really don't like writing when you read his thing on how he wrote the James Bond books. You write a James Bond book in two weeks. You check into a hotel. You have to check into a hotel somewhere that you don't want to be.

Starting point is 00:08:21 Otherwise, you might go out and walk around and become a tourist. You have to check into a not terribly nice hotel room otherwise you might luxuriate and enjoy it and instead what you want to be is focused on getting out and then you having nothing else to do in this town in this place you settle down and you write like a fiend and you get your James Bond book written in two weeks and you leave this horrible hotel room. And that was how he did it. And I have tried it a couple of times. I did it with the American

Starting point is 00:08:58 draft of Neverwhere. That was the first one I ever tried. And I did the entire set of American draft, which was a big second draft. The book had already been published in the UK, but my American editor wanted stuff done because she pointed out that the book as it existed was written for people who knew that Oxford Street was a big street with lots of shops on it or whatever. It was written for Brits and Londoners. And she wanted something expanded. So I expanded it. And I was in a room with, as far as I remember, no windows in the, I think it was a Marriott in the World Trade Center, which is no longer there. But writing in that hotel room, you just wanted to be out. And it seems to me, and you can't believe everything you read on the internet, so I want

Starting point is 00:09:59 you to certainly fact check me as needed, but that you also have or have had some internal rules. So you can use your external environment to assist. But I read that, and again, feel free to correct, but making rules, the importance of making rules, rules like you can sit here and write, or you can sit here and do nothing, but you can't sit here and do anything else. That was always, and still is, when I go off to write. That's my biggest rule. Could you speak to that? Yeah, because I would go down to my lovely little gazebo,

Starting point is 00:10:32 the bottom of the garden, sit down, and I'm absolutely allowed not to do anything. I'm allowed to sit at my desk. I'm allowed to stare out at the world. I'm allowed to do anything I like, as long as it isn't anything. Not allowed to do a crossword, not allowed to read a book, not allowed to phone a friend, not allowed to make a clay model of something. All I'm allowed to do is absolutely nothing or write. And what I love about that is I'm giving myself permission to

Starting point is 00:11:06 write or not write. But writing is actually more interesting than doing nothing after a while. You know, you sort of sit there and you've been staring out the window now for five minutes, and it kind of loses its charm. You're going, well, actually, might as well write something. And it's hard. As a writer, I'm more easily, you know, I'm distractible. I have a three-year-old son. He is the epitome of cuteness and charm. It's more fun playing with him than it is writing, which means if I'm going to be writing, I need to do it somewhere where I don't have a three-year-old son singing to me, asking

Starting point is 00:11:47 me to read to him, demanding my attention. I think it's a really just a solid rule for writers. It's like, yeah, you don't have to write. You have permission to not write, but you don't have permission to do anything else. It reminds me of another one of my favorite writers, you being the one who's sitting in front of me, John McPhee, nonfiction writer, who has spent much of his life in Princeton, New Jersey, but has written some incredible Pulitzer Prize winning nonfiction. And I was lucky enough to take class with him a thousand years ago.

Starting point is 00:12:23 And his role was very similar, although he didn't state it explicitly he would sit in front of his first as a young man typewriter and he could sit in front of the blank page and from 8 a.m to 6 p.m with the exception of a break for lunch and swimming it was the blank page or writing it was disallowed from doing anything else are there any other rules or practices that you also hold sacred or important for your writing process? Some of them are just things for me. For example, most of the time, not always, I will do my first draft in fountain pen, because I actually enjoy the process of writing with a

Starting point is 00:13:09 fountain pen. I like filling a fountain pen. I like uncapping it. I like the weight of it in my hand. I like that thing. So I'll have a notebook, I'll have a fountain pen, and I'll write. If I'm doing anything long, if I'm working on a novel, for example, I will always have two fountain pens on the go, at least with two different colored inks, at least, because that way I can see at a glance how much work I did that day. I can just look down and go, look at that, five pages in brown. I wrote that. Half a page in black. That was not a good day.

Starting point is 00:13:49 Nine pages in blue. That was, what a great day. And you can just sort of get a sense of, okay, are you working? Are you making forward progress? What's actually happening? And I also love that because it emphasizes for me that nobody is ever meant to read your first draft. Your first draft can go way off the rails. Your first draft can absolutely go up in flames. You can change the age, gender, number of a character.

Starting point is 00:14:20 You can bring somebody dead back to life. Nobody ever needs to know. Anything that happens in your first draft is you telling the story to yourself. And then I'll sit down and type. And I'll put it onto a computer. As far as I'm concerned, the second draft is where I try and make it look like I knew what I was doing all along. Do you edit then as you're looking or translating from the first draft on the page to the computer or do you get it all down as is in the computer and then edit no i i definitely that's my editing process i think that's my second draft is typing it into the computer and also i And also, I love, so backing up a bit here. When I was 27, 28, in the days when we were still in typewriters,

Starting point is 00:15:11 and there were just a handful of people with word processors, which were clunky things with disks, which didn't hold very much and stuff. I edited an anthology and enjoyed editing my anthology. Most of the stories that came in were about 3,000 words long. Move forward in time, not much. Five, six, seven years, mid-90s. Everybody is now on computer. And I edited another short story anthology. And the stories that were coming in tended to be somewhere between 6,000 and 9,000 words long. And they didn't really have much more story than the 3,000 words ones. And I realized that what was happening is it's a sort of a computery thing.

Starting point is 00:16:00 Is if you're typing, putting stuff down is work. If you've got a computer, adding stuff is not work. Choosing is work. So it sort of expands a bit like a guess. If you have two things you could say, you say both of them. If you have the stuff you want to add, you add it. And I thought, okay, I have to not do that because otherwise my stuff is going to balloon and it will become

Starting point is 00:16:30 gaseous and thin. So what I love, if I've written something on a computer and I decide to lose a chunk, it feels like I've lost work. If I delete a page and a half, I feel like there's a page and a half that just went away. That's a page and a half's worth of work I've just lost. If I've been writing in a notebook and I'm typing it up and I can look at something and go, I don't need this page and a half, and I leave it out, I've just saved myself work. And it feels kind of like I'm treating myself. So I'm just trying to always have in my head the idea that maybe I'm somehow on some cosmic level paying somebody by the word in order to be allowed to write.

Starting point is 00:17:23 If they're there, they should matter. They should mean something. It to be allowed to write. If they're there, they should matter. They should mean something. It's always important to me. This might seem like a very, very mundane question, but what type of notebooks do you prefer? Are they large, like legal pads? Are they leather-bound? What type of notebooks?

Starting point is 00:17:39 When they came out, I've used a whole bunch of different ones. I bought big drawing ones, which actually turned out to be a bit too big. Well, I kind of liked how much I could see on the page. Those were the ones I wrote Stardust and American Gods in, sort of big size. But they weren't terribly portable. I went over to the Moleskins, and I loved them when they first came out, and then they dropped their paper quality. And dropping paper quality doesn't matter unless you're writing in fountain pen, because all of a sudden, it's bleeding through. And all of a sudden, you're writing on one page,

Starting point is 00:18:20 leaving a page blank, because it's bled through and writing on the next page. And Joe Hill, about six or seven years ago, Joe Hill, the wonderful horror fantasy writer, suggested the Leuchtturm to me. So my usual notebook right now is a Leuchtturm because I really like the way you can paginate stuff in them and the thickness of the paper. And they're just like sort of moleskins, but the Porsche of moleskins. They're just better. And I also have been writing, I wrote the graveyard book, and I'm writing the current novel in these beautiful books that I bought in a stationary shop in Venice, built into a bridge. Somewhere in Venice, there's a little stationary shop on a bridge, and they have these beautiful leather-bound blank books that just look like hardback books, but they're blank pages.

Starting point is 00:19:21 And I wrote the graveyard book in one of those. I bought four of them. And now I'm using the next one on the next novel. And it may well go into another one. I'm not sure. And then at home, I say at home, my house in Wisconsin, which is where my stuff is. We live in Woodstock, but I have an entire life's worth of stuff still sitting in my house in Wisconsin. And it's become archives. It's actually kind of fabulous is a book that I bought for myself about 25 years ago. And before I die, I plan to write a novel in it. And it's an accounts book from the mid-19th century. It's 500 pages long. Every page is numbered. It's lined with accounts lines, but very faint. So it'll be nice to write a book in it. And it is engineered so that every single

Starting point is 00:20:34 page lies flat. And it's huge, and it's heavy. And it just looks like a book that Dickens or somebody would have written a novel in. And I've just been waiting until I have an idea that is huge and weird and Dickensian enough. And whether or not I actually get to write it in dip pen, I'm not sure. But I definitely want to write it in a sort of old Victorian, something slightly copper platey, one of those old flex nib pens that they stopped making when carbon paper came in, just so I can get that kind of spidery Victorian handwriting. I'm just imagining you putting pen to the first page

Starting point is 00:21:19 when you finish the first page and what that will feel like. That's going to be a good day. It will be either a good day or an incredibly bad day. I'll get to the end of the first page and what that will feel like that's going to be a good day it will be either a good day or an incredibly bad day i'll get to the end of the first page oh no i have this pristine but it is it is the thing that i tell young writers and by young writers a young writer can be any age you just have to be starting out which is anything you do can be fixed what you cannot fix is the perfection of a blank page. What you cannot fix is that pristine, unsullied whiteness of a screen or a page with nothing on it, because there's nothing there to fix.

Starting point is 00:21:56 Are there any particular fountain pens or criteria that you would use in picking a good pen? You know, the biggest criteria I would use in picking, if you have the choice, is go somewhere like New York's Fountain Pen Hospital. Is that a real place? It's a real place. It's called the Fountain Pen Hospital. They sell lots of new pens. They recondition old pens.

Starting point is 00:22:21 They look after pens for you. And try them out. Because the lovely thing about fountain pens is they are personal. You go, and try them out. Because the lovely thing about fountain pens is they are personal. You go, no, no, no, and then you find the one. I tend to suggest to people who are nervously, I've never used a fountain pen, what should I do? And I will point them at Lamy, L-A-M-Y, who have some fabulous starter pens. And they're not very expensive, and they're good. They do a pen called the Safari, but they have a bunch of good starter pens. And they're just nice to get into the idea of, do I like doing this? So I was doing prep for this conversation,

Starting point is 00:23:01 and came across an interview in which you said that for nonfiction, you can kind of write wherever it happens to fall. If it's a script or something else, but that for novels, very often you tend to write between, say, 1 and 6 p.m., where you'll handle email, maybe writing a blog post and so on in the morning. And I'd love to chat about that, because many of the writers I've spoken to, and I'm sure it differs person to person, but tend to write either very late or very early because they feel like they avoid distraction. When I started out, from the age of about 22, when I was a young journalist, 26, 27, a starting out comics writer, all through there, I was a late, late night writer. Nothing really happened until the kids were in bed, nine o'clock.

Starting point is 00:23:57 I might have faffed her out a little bit during the day, but now it's all done, and now I'm getting down to work. And at two or three o'clock in the morning, and I'm writing in England at this point, I may phone a friend in America just to talk enough to make sure that I'm awake. So that's what I did. And I was a smoker and a coffee drinker, and it was great. I moved to America in 92, gave up smoking 93, stopped drinking coffee, went over to tea, and tried carrying on being a late-night writer and gradually realized that I wasn't really anymore. What tended to happen was somewhere around one in the morning, I'd be writing away. And then I would lift my head from the keyboard at four o'clock in the morning and have 3000,000 pages of the letter M and just go, okay, this doesn't really work anymore for me. And then I started rescheduling, trying different things out.

Starting point is 00:24:56 Part of what I discovered, particularly about being a novelist, is writing a novel works best if you can do the same day over and over again. The closer you can come to just Groundhog Day, you just repeat that day. You set up a day that works for yourself. The last novel that I actually wrote, I was at Tori Amos's wonderful house in Florida. She has this lovely sort of house on the water that she's lent me many times to go and write in. And I went down there, and I would get up in the morning. I would go for a jog, come back, do my yoga,

Starting point is 00:25:43 get dressed, get in the car, drive down to a little cafe where there were just enough people around that I knew that other people existed, but nobody that I would ever be tempted to talk to. And I would order myself a large cup of green tea, sit in a corner, and just start writing. And I would do that day over and over and over and over. And, you know, a couple of months later, I looked up and I had the ocean at the end of the lane, which was only meant to have been a short story anyway, it just kept going. That, I think, works really, really well. I also think that the most important thing for human beings is to be aware of the change. The biggest problem we run into is going, this is who I am, this is what I'm like, this is how I function, while failing to notice that you

Starting point is 00:26:42 don't do that anymore. I'm perfectly aware that I may one day become one of those people who wakes up early in the morning and goes and writes. My friend Gene Wolfe, who is now in his late 80s and is one of the finest writers that America has for years, was an editor of a magazine about factories. I think it was called Plant Engineering. So he'd get up at four o'clock in the morning and write for an hour before anything else, before the day started, before he had to leave for work, and before anybody else was up. And that was how he did it.

Starting point is 00:27:29 I cannot imagine getting up in the morning and just writing. That's not how my head works. I need a while to get here. But I can absolutely imagine that one day I'll have become one of those morning writers. From having been a late night writer in my youth and an afternoon writer in my middle age in my dotage i could absolutely become a morning writer in your dotage i think that's going to take a while what are the types of things that you learned from terry or picked up the biggest thing looking back

Starting point is 00:27:59 on it that i learned from terry pratchett was a willingness to go forward without knowing what happens. You might know what happens next, but you don't know what happens after that. But it's okay, because you're a grown-up, and you will figure it out. There's lots of metaphors for writing a novel and george rr martin for example divides writers into architects and gardeners and i can be an architect if i have to but i'd rather be a gardener i would rather plant the seeds water them and figure out what I'm growing as they grow, and then prune it and trim it and bleach it, whatever I need to do to make something beautiful that appears intentional. But at the end of the day, you have to allow for accidents and randomness and just what happens when things grow. So the joy of good omens really, I mean, the best thing of good omens really i mean the best thing about good omens was having terry pratchett

Starting point is 00:29:09 as an audience because if i could make terry laugh it's like hitting the thing in the circus with the hammer if you bing the bell at the top that's what i did when i could make terry laugh many many of my fans are your fans. And just as Terry shared his gifts with the world, you continue to share yours. And it has an impact. It helped me through some very tough times. I was able to transport me, delight me, shock me, scare me, and take me through a whole range of emotions I didn't at the time, even though I had access to. So I want to thank you for making good art and sharing it with the world. You've done a great job.

Starting point is 00:29:47 You are so ridiculously welcome. Thank you. Just a quick thanks to one of our sponsors and we'll be right back to the show. This episode is brought to you by LinkedIn Jobs. When you're hiring for your small business, you want to find quality professionals that are right for the role as soon as possible. That's why you have to check out LinkedIn Jobs.

Starting point is 00:30:10 LinkedIn Jobs has the tools to help find the right professionals for your team faster and for free. LinkedIn isn't just a job board. LinkedIn helps you hire professionals you can't find anywhere else, even those who aren't actively searching for a new job, but who might be open to the perfect role. In any given month, more than 70% of LinkedIn users don't visit other job sites. So if you're not looking on LinkedIn, if you're not using LinkedIn, you are in the wrong place. More than 2.5 million small businesses use LinkedIn for hiring, with 86% getting a qualified candidate within 24 hours. LinkedIn knows that small business owners, leaders, execs are wearing so many hats, they're stretched then. They might not have the time or resources to hire in any drawn out way. So LinkedIn is constantly finding

Starting point is 00:30:54 ways to make the process easier. In fact, they just launched a feature that helps you write job descriptions, making the entire thing A to Z faster and much simpler. So hire professionals like a professional on LinkedIn. And now you can post your job for free at linkedin.com slash Tim. That's linkedin.com slash Tim to post your job for free. Terms and conditions apply. And now, Debbie Millman, host of the Design Matters podcast, chair of the SVA Masters in Branding program, editorial director for Print Magazine, and one of Graphic Design USA's most influential designers working today. You can find Debbie on Twitter and Instagram at Debbie Millman. Debbie, welcome to the show.

Starting point is 00:31:47 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 in 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? 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

Starting point is 00:32:27 I'm a designer and a writer and a podcaster. And sometimes people look at me like, huh? Like, huh? 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. Executive is a great catch-all. For a long time on Twitter, I had Debbie Milliman is a girl until enough people said, Debbie, you've really got to change that. And then I did.

Starting point is 00:33:13 Oh, the internet. Well, you could put anything there. And I think about 10% of the people who come across it 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. 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. Oh, Tim, I learned's start with, and for those people wondering, I always ask my guests beforehand, are there any particular say prompts for stories that we could explore that,

Starting point is 00:33:54 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 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 report 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

Starting point is 00:34:49 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 handiwork, because 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 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

Starting point is 00:35:38 a sense of how old I am. I lived there until I was about, I was in the middle of the third grade and we moved to Staten Island. And I lived on Staten Island until I was in the fifth grade, end of fifth grade. My parents got divorced. My mom took my brother and I, who 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 drew it 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,

Starting point is 00:36:53 bank, and I labeled the taxi, taxi. In the middle of the street, there 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 drawing, I realized that I had predicted my whole life. I'm a native New Yorker now living in Manhattan. I've been living in Manhattan for 33 years. I go to the bank, I go to the cleaners, I take lots of taxis, lots of buses. And at the time I found this drawing, I was drawing logos for a living. And, you know, 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.

Starting point is 00:37:54 This is fascinating to me for a number of reasons. I've had a few guests on the podcast. Chris Saka would be another example, was an investor. And he, at some point point wrote in a journal, well, I think it was one of these composition notebooks with the sort of model black and white zebra slash camouflage covers. Oh, I love that. What he would be when he was 40 years old. And he must've done this when he was 10 or 12, something like that. And 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

Starting point is 00:38:26 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 say, you know, when I was five, I knew I always wanted to be X. But what was your, 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 the summer of 1983. I often say that that was the summer of

Starting point is 00:39:36 David Bowie's Modern Love and the Police's Synchronicity. I saw both concerts that summer. I moved into a sublet apartment with a friend that had also recently graduated. She had found a sublet on the corner of Hudson and Perry streets in the village. I didn't know it at the time, but moving into an apartment on the intersection of Hudson and Perry was almost as if I was entering the movie Gidget Goes to Manhattan. I didn't know where I was going. It was quite serendipitous. My friend Jay found the apartment for us.

Starting point is 00:40:19 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, because 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 walk up, 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,

Starting point is 00:41:06 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 lived there for about five years before I ended up moving back into the village for a short period of time. So that was the one thing 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,

Starting point is 00:41:36 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, compute graphic 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? Was that something you started at the very beginning and followed throughout your, I guess, undergrad experience?

Starting point is 00:42:48 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, you know, I didn't say what I was thinking, but like hair clips? I mean, 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.

Starting point is 00:43:38 I was so intimidated by the talent and the work that was coming out of that newsroom. And it was at the time, and very well may still be one of the best student newspapers in the country. It came up twice a week, Tuesdays and Fridays. And I was just enamored with this newspaper. And I fantasized about writing really pithy, erudite letters to the editor-in-chief that would then get published in, you know, 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'd 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.

Starting point is 00:44:26 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 at the student 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 in 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 features section and began that summer. That senior year in college was one of the most exciting and best years of my life in that for the first time ever, I felt like I had purpose. Suddenly working on this paper, I felt like I was part of something bigger than

Starting point is 00:45:25 myself. I felt like I had some reason for being. And I loved learning about design. I loved being able to work with writers. And I felt for the first time in my life really excited about something. I want to 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 for a much better story and certainly a

Starting point is 00:46:10 better interview. What I can tell you is that all these years later, I have noticed a pattern in my life of being very easily hurt by an initial reaction or an initial rejection, so much so that it thwarts any other attempt at making something like that path for quite a long time. It takes me a while to recover. Could you give any examples of that? I would say my entire life. I will give you, I can give you 43 examples. Get comfortable, Tim. Yeah, 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

Starting point is 00:47:11 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 rejected, I used that first rejection almost as a permission slip to avoid having to try again. So when I graduated, I started working at a couple of different magazines.

Starting point is 00:48:15 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

Starting point is 00:49:17 some good response from it, but I don't feel qualified or educated enough. Maybe I should get an advanced degree in art. And 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-knitting my confidence or hopes and dreams together, and then trying to do something else or trying again.

Starting point is 00:50:13 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. 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. 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

Starting point is 00:51:36 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. 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. Your clips mention, 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 going to come back to that. Oh, Tim, can I add one more thing? Of course. I'm sorry. This isn't interesting. You can add many things, please. So one thing that I haven't shared about this particular story is that the young man that rejected me that first year is somebody that I then befriended in that experience of working at the paper that junior year. And I graduated in 1983.

Starting point is 00:52:47 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

Starting point is 00:53:22 from high school, which I didn't feel were appropriate, that I was the one that rejected myself in many ways. One of the interesting things that I'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've become, 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've 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. And I, in some respects like you, have been very sensitive.

Starting point is 00:54:35 I still am in some respects very sensitive. And my particular brand of that or my particular type of response is to feel 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. 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.

Starting point is 00:55:34 And that didn't cover it all for me though, but it really made a profound impact on me when I was told this. Because 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. 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.

Starting point is 00:56:13 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, you know, I'm not going to 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 of the four hour workweek to this person via email. And the response was, effectively, thanks, but sorry, don't have time to read this right now.

Starting point is 00:56:51 No, dear Tim, no signature, just one line. And I felt so slighted by this that I held this subconscious grudge for years. And now we're really good friends and the whole thing is ludicrous in retrospect. One thing that I find about human nature is that ambiguity is always perceived negatively. So there might be nothing in that one line email that would be in any way disparaging or insulting or anything. But because we as humans perceive ambiguity negatively, we tend to read into things that aren't there in a way that makes us feel bad. But I also think that a lot of that for me comes from having a very sort of fragile center and not necessarily thinking that they are specifically upset with me because of something that I've done, but just because everything that I do is sort of bad. They're just cognizant of that. So it's not

Starting point is 00:57:55 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, you mentioned clips, clips, hair clips. I was told this story by a professor in college about Nantucket Nectars when it was just getting started. And there were, I believe, two guys who were really faking it until they made it in a lot of respects. And at one point, they were meeting

Starting point is 00:58:42 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 it met with this it was either a retailer or distributor but 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? 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 I wanted to, to, before we get to when you sort of first clicked into your your niche and how that happened you mentioned knowing that you wanted to be in manhattan and i've been thinking a lot about

Starting point is 00:59:34 the components of and this is a dangerous word sometimes but happiness and that oftentimes we think of the journalist w's right the interact The interactives, 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 somewhere lower, and then where is often an afterthought. But I've started to believe that the where is much more critical than we give it credit for, and that you can actually start there. So I 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. But if you think about that, how do you think about the

Starting point is 01:00:18 components of happiness or well-being for yourself? 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 inns 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.

Starting point is 01:01:19 In thinking about what I wanted with my life, I knew that I wanted to do something creative. One of my big hopes and dreams at that time was to work at Condé Nast, and I did apply, and I did get a call back, and I got rejected and then never tried again, another example of that. But one of the more 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. 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

Starting point is 01:02:27 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 Bleecker Street and 6th Avenue, and it suddenly occurred to me that I had to make a decision.

Starting point is 01:03:26 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 considered to be my financial future, and therefore made this little pact with myself in my head that I would become a designer so that I could make enough money to be able to be secure. And I've been telling myself that for decades. What I realized in the last couple of years was that I was, unbeknownst to my psyche, my consciousness, I was lying to myself. I was absolutely positively lying to myself because more than the self-sufficiency was the desire to be in Manhattan. I could have 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 in Queens. I could have lived with friends in Albany. I could have had seven roommates in a

Starting point is 01:04:46 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

Starting point is 01:05:36 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 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. Oh, definitely. By hook or crook, you're living in Manhattan. And that is the outcome in part of all of these decisions and the lead gene, as you put it.

Starting point is 01:06:42 Where does the need for stability, security, or the desire for that come from? I do think that it's certainly in Maslow's hierarchy of needs, a really important one. For me, it takes on 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. 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

Starting point is 01:07:48 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 his, to one of his two biological daughters, and severely, severely beat us for four years. During that time was one of the times, 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

Starting point is 01:08:56 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 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 for 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.

Starting point is 01:09:54 Of course, it's not. That takes decades to also figure out. But at that time, I wanted very badly to be able to live in my own home, to be able to take care of myself, and to be in a position where I would never be vulnerable again, you know, sort of Scarlett O'Hara. I'm never going to go hungry again. Yeah, it 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 victim of these types of situations.

Starting point is 01:10:53 I've spent a lot of time working on better integrating those experiences into my life in a way to not only understand what happened, why it happened, what the aftermath then caused, but also how I can use that empathy and that understanding to try to help the world. And that's a lot of the reason that I've started to do the work that I do with Mariska Harkite and the Joyful Heart Foundation, which is a foundation that Mariska started after she started working on Law & Order SVU. 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

Starting point is 01:12:07 working with Mariska 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. 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

Starting point is 01:13:06 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 mind me asking? I

Starting point is 01:14:05 know very little about it. 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 are a lot of resources. One of the things that I experienced when I was in the midst

Starting point is 01:15:06 of these experiences was a sense of profound aloneness. The worst experiences I had were in the 70s. And at the time, the topic wasn't one that was as understood. I didn't know what was happening to me. I thought I was the only person in the world that this was happening to because it seemed so surreal and unnatural and punishing. It didn't occur to me that this was pervasive, that this was a cultural epidemic. 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. It's horrible. to hurt my brother and my mother, that he would kill them. Horrible. And I believed that. I was a little girl.

Starting point is 01:16:07 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 want to be the reason. I didn't want to be blamed. And I also didn't think anybody would believe me. And I didn't want my mother and my brother to be harmed. It wasn't until I was much older that

Starting point is 01:16:37 I realized that this was pervasive. So for anybody that is listening, if you feel alone, know that you're not. You can go to the Joyful Heart Foundation, the joyfulheartfoundation.org, and there are resources and phone numbers. You can also go to nomore.org, 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. To insert some levity, I'm not sure how to segue from here. But 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.

Starting point is 01:17:26 One of the other things that Joyful Heart is doing that I am so proud of is ending the backlog. There are hundreds of thousands of rape kits that are not being investigated that are sitting in shelves in police departments all over the country. And so the Joyful Heart Foundation, along with Vice President Joe Biden, has been very involved in getting funding to help analyze those rape kits to be able to analyze the DNA and get serial rapists off the streets and get justice for the victims of those crimes. So that's a really, really important thing that

Starting point is 01:18:05 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. 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.

Starting point is 01:18:30 So you can certainly find links to nomore.org, the Joyful Heart Foundation, and so on at 4hourworkweek.com forward slash podcast, all spelled out. Debbie, I'd love to ask you to shift gears just a little bit,

Starting point is 01:18:44 or perhaps a lot, the speak-up story. That's one of my favorite stories. I will let you run with it. I would love for you to share. Okay. So I want to start this story by letting people know that this was something that while it was happening, I thought was the worst professional experience of my life. And it's turned out to be the most important and life-affirming of my life. So let me tell you a little bit about the Speak Up story. 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.

Starting point is 01:19:36 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

Starting point is 01:20:13 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 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. I was going to say Lay's potato chips. I was going to say Lay's potato chips. 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,

Starting point is 01:21:42 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? I was working in marketing and sales. And 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

Starting point is 01:22:27 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 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.

Starting point is 01:23:23 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.

Starting point is 01:23:43 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 the sort of day-to-day runnings of this little special interest group. At the end of the two years, we all had to reapply

Starting point is 01:24:09 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 the cupcakes. I know. They were really good cupcakes and brownies. And I was devastated. I was just devastated. And Rick Raffae, 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,

Starting point is 01:24:50 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 curb by the special interest group of the Brand Experience Center. This was like the biggest honor of my career at that point. To be a judge in the country's biggest design competition was unfathomable to me. It felt like a miracle. 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

Starting point is 01:25:45 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.

Starting point is 01:26:19 Yeah. Anyway. Sorry, guy. I don't know. 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. And I was like, okay. And I didn't agree with that. I was working at a CPG package design firm, and we had recently designed the Burger King logo and the Star Wars Episode II attack of the clones packaging and merchandising and the Hershey bar.

Starting point is 01:26:51 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 going to actually come to fisticuffs. Was this behind the scenes or is this while you were 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.

Starting point is 01:27:13 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.

Starting point is 01:27:48 It was sort of dusk, and I felt like, oh, this is never, ever going to work out. And resigned myself to that. Rick asked for some work of mine to be included in the journal as evidence of my credentials for being a juror. And the two biggest projects that I had done at the time were the Burger King identity and the Star Wars identity. And so I sent those in as my credentials. They were 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. 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. 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,

Starting point is 01:28:50 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 weblogs and the first design blog. And the letter chastises AIGA for including me, Debbie Millman, as a juror in their annual competition, what is supposed to be the most prestigious competition in the country, and accused me of not only being a corporate clown, but also because of the work I do, they called me a she-devil.

Starting point is 01:29:32 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, yes.

Starting point is 01:29:51 I'm so glad that hateful comments are a thing of the past. But yes. Oh, yes. Intimately, intimately familiar. Right. And I'm reading this and my jaw is agape and I am just in a state of catatonia. I couldn't move. I was ashamed, embarrassed, terrified that people in my office would see it, that the reputation of the firm was being sullied by me. And I didn't know what to do. I was despondent. I remember walking home from work that day crying, thinking that I had to quit.

Starting point is 01:30:34 I had to leave the design business. And my career was over. This career that I had finally found for myself was now officially over. 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

Starting point is 01:31:09 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, you're not going to approve of this. 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.

Starting point is 01:31:44 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 Landor is one of the world's biggest and most respected brand consultancies,

Starting point is 01:32:52 started by Walter Landor about 80 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 it was the original writer of this open letter, Felix Aquil, the illustrator and designer. And then I thought it was over. I thought it had ended with some sort of a compromise in viewpoints. But to my chagrin, the writers at Speak Up kept writing about me. And the next article was called, Is the Dark Side Prevailing?

Starting point is 01:33:37 So subtle. So subtle. Very subtle. 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 want to be able to see this site. And he did. Sometimes you need a helpful pair of handcuffs. Well said. But I'd still, you know, I'd go home and look, but whatever. A couple weeks later, the founder of Speak Up, a young man about 23

Starting point is 01:34:12 years old, named Armin Witt, reached out to me. He wrote me an email, and he apologized. He didn't apologize for calling my work a pair of turds, which is what he did. I didn't realize turds came in pairs. It shows what I know. So he apologized for the bullying and for the unprofessional way in which the conversation

Starting point is 01:34:36 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 diatribe 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. So I said, yes. And I started writing for Speak Up. The Darth Vader column.

Starting point is 01:35:18 Well, what was so interesting about the experience, Tim, was that what the speak-uppers 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. started writing for Speak Up, and all of a sudden I started to have that sense of what I had been originally searching for in my efforts with Speak Up. I felt like I was part of something bigger than myself. I felt like I was part of this sort of renegade group of misfits that were trying to change the world through graphic design criticism and online conversations. We all decided that year in the fall of 2003 that we were going to go as a group of sort of guerrilla speak-up writers to the upcoming AIGA annual conference in Vancouver.

Starting point is 01:36:34 And we were going to give out this little brochure that Armin had put together called Stop Being Sheep, which was a riff on the great typographer Eric Spiekerman's book Stop Stealing Sheep, which is about letter spacing. You know, thin slicing here to the very best of our ability. And so we went with this little brochure en route to the conference. So these people then ended up accepting you, the people who had previously vilified you? The people that had previously vilified me not only accepted me, but over the years, Armin and his wife, Bryony, 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

Starting point is 01:37:26 rejected me or what I thought was a rejection of me then ultimately became one of my lifelong friendships. And now Armin and Bryony are also family at this point. Family. Amazing. So I interrupted that. So you're en route with this group of heretics and a pile of brochures or pamphlets. Right, because brochures change the world.

Starting point is 01:37:47 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 Sher. 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 are the people eating it, not the people smelling it. True fact.

Starting point is 01:38:20 You know, I don't know why I didn't think that I would see people that I knew on this flight. 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.

Starting point is 01:38:44 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 hours, and then we go off and do our own thing with whatever else we were doing on the flight. When I get to my room in Vancouver, I take her card out of my bag, and I see that she's the editor-in-chief, Joyce Redder Kay. I invite her to the party. She comes and we start a correspondence. I harbored this hope that maybe I could write for Print Magazine one day.

Starting point is 01:39:16 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 at the time, reality TV had just sort of burgeoned into culture. And there was a very popular TV show called Iron Chef about cooking in real time and the audience voting. 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's the oldest graphic design magazine in the country. It's 75 years old. It has won, I think, five magazine awards, which is the highest honor, an Effie, 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.

Starting point is 01:40:21 So ironic chef. Yes, ironic chef. Debbie Millman's personal version of hell. Yeah. And I'm afraid to say no. I feel like if I say no, I'm never going to be offered an opportunity to do anything with Joyce again. So I say yes, and I'm further humiliated when I get to San Diego, when I realized that I have to wear a chef's outfit on stage. There are pictures of this, by the way. I'm not lying or exaggerating. So I go through with this. I am on stage with the emcee Steve Heller, who I'd never met. Steve Heller is

Starting point is 01:40:54 one of the world's foremost design critics. He was the art director of the New York Times Book Review for 30 years. He started numerous programs at the School of Visual Arts, graduate programs, and he's written about 170 books about design and graphic designers. He is the judge. I am terribly intimidated because he is Steve Heller, one of the greatest people 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 asked Steve, because he was nice to me that day, if he'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. I wrote it on a paper napkin,

Starting point is 01:41:46 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 going to be asked for anything again. And I take on this book. But I asked 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

Starting point is 01:42:42 became my first book. In the meantime, Joyce, writer K, the editor of Print Magazine, reaches out and asks me if I'd like to write a review about Wally Olin's 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. Thirteen years later, two years ago, I was appointed the editorial and creative director of Print Magazine. Well, it seems like those brochures did play a role. Yep. And that's just the start of it, Tim. contacted by a fledgling internet radio network called Voice America in 2004,

Starting point is 01:43:31 shortly after a piece that Mark Kingsley and I wrote about election graphics that kind of 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, a radio network show. They said yes. Just when I was beginning to think, oh, I might get rich from this, they told me that I needed to pay them for the airtime. Surprise. Another surprise. But I was really excited about this. And at that time, you know, everything I was doing was very commercially driven and felt that this would

Starting point is 01:44:13 be a way for me to talk about graphic design and engage with people in a way that had no commercial value whatsoever. It 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 the show for four years on Voice America, paid them for four years to do it, and then brought the show to Design Observer. Bill Drantel, the late, great Bill Drantel, the founder of Design Observer. Bill Drentel, the late great Bill Drentel, 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. You ever have a conversation

Starting point is 01:45:00 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. 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 going to have my 12th anniversary of Design Matters. We won a Cooper Hewitt National Design Award in 2009. At the end of 2015, iTunes, and you know this because you're always on the list, but after 11 years, iTunes designated it one of the best podcasts on iTunes. And I've transitioned the show from a show about why design matters to

Starting point is 01:45:43 a show about how creative people design their lives and the trajectory that people take. Even from this conversation, you can probably tell how interested I am in how people make their lives, the choices 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

Starting point is 01:46:16 and with the intensity that you are interested, I think is very well reflected in the episodes themselves. And we've spent some time in your studio. Yes. 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,

Starting point is 01:46:53 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. And as you'd mentioned, you'd done, I guess, brand makeovers or branding for Burger King, Star Wars, I think you, Hershey's, Tropicana, I think. Yes, yes. 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?

Starting point is 01:47:25 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 at some point your hand was involved in just an incredible array and plenitude of different products. How did Milton Glaser enter the scene, And could you describe for people who he is? living graphic designer. He's in his 80s. He is responsible for the I Heart 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.

Starting point is 01:48:31 My relationship with Milton really began when I took a class of his at the School of Visual Arts, a summer intensive, in the summer of 2005. I had already interviewed him for Design Matters, but it was over the phone. And while I cherish that interview, it was one of my very, very early interviews. So I'm somewhat gun-shy to send people to listen to that one because it's so early in my journey as a podcaster. But in any case, I took this class with him. And that class, 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. important things that he did. He's not teaching it anymore. He had us do an exercise in that class where we had to envision the life that we could have if we pursued everything that we wanted with the certainty that whatever it is that we wanted, we would succeed. I wrote an essay in July of 2005. It was supposed to be a five-year plan. 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

Starting point is 01:49:58 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.

Starting point is 01:50:39 Can you describe the exercise as you do it with your students now? Well, I teach undergrad and graduate classes at the School of Visual Arts. I run a master's in branding program at the School of Visual Arts, which I was given this opportunity via Steve Heller, who I, again, would not have met had that whole speak up experience not happened. So yet another thing, every single thing that I'm doing now in my life, Tim, stems from that experience. Well, also just to underscore another theme, he had in some sense, you could interpret it as rejected two of your book ideas, even though he's nice to you and went out to lunch with you. But now later on down the line, you kept that relationship

Starting point is 01:51:25 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

Starting point is 01:52:20 when I was doing this five-year essay or 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.

Starting point is 01:53:16 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 there recommendations, ways to start? Is it bullets or is it prose in full paragraphs? No, so it's full paragraphs. 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?

Starting point is 01:53:43 What are you doing? Where are you living? Who are you living with? Do you have pets? What kind of house are you in? Is it an apartment? Are you in the city? Are you in the country? What does your furniture look like? What is your bed like? What are your sheets like? What kind of clothes do you wear? What kind of hair do you have? Tell me about your pets. Tell me about your significant other. Do you have children? Do you have a car? Do you have a boat? Do you have, talk about your career. What do you want? What are you reading? What are you making? What excites you? What is your health like? And write this day, this one day, 10 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.

Starting point is 01:54:49 Put your whole heart into it. And write like there's no tomorrow. Write like your life depends on it because it does. And then read it once a year and see what happens. It's magic. It's magic, Tim. It is a magical exercise. 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 10 years ago that are like,

Starting point is 01:55:26 Debbie, it all came true. How did this happen? And 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 Bleecker Street and 6th 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 10-year plan for a remarkable life. How long was your essay?

Starting point is 01:56:24 Is there any consistency to length? Are there guidelines or is it as long as it takes? And some are two pages, some are 20 pages. Some are two pages, some are 20 pages. I think the longer it is, the more likely it is to be affirmed for some reason. I find the more care you put into it, the more care and detail you put

Starting point is 01:56:45 in. Oh, doggy. That's, that's, that's doggy. Yeah. That's, that's my Molly. Sorry. She's excited about this exercise. Please get me. Yeah, clearly. I think that the more care you put into it, the likely, the more success you'll have coming out of 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 10 handwritten, big handwriting. I had big handwriting, 10 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.

Starting point is 01:57:22 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. I have so many questions I'd still like to ask, but I think that is 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. But before that, is there any parting piece of advice or recommendation, question, anything that you'd like listeners to carry with them when they stop listening to this? I recently went through a pretty major transition in my life.

Starting point is 01:58:20 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 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

Starting point is 01:59:23 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 Omnicom. 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 earn out at Sterling and then leave and transition to working at SVA and doing all of the personal projects that I had been talking for so long about doing. So the five years happened and we had a really wonderful, successful earn out. So there was no excuse to him for me to continue on the same path. And it was time to make that change. And the last thing I wanted was to end up like the characters

Starting point is 02:00:26 in Revolutionary Road, that remarkable book where people talk about making these changes their whole lives and then never ever do. But I became terrified. I became terrified that if I made this change that I would not have financial stability anymore, that I would not be able to fulfill all of the dreams that I had and would have to confront that. And so five years turned into six years and six years turned into seven years. And just at a point where I was starting to think about really doing it, sort of like Al Pacino in Godfather 3, I was offered an opportunity to take over as CEO of the company. Simon Williams, the then CEO, was looking to become chairman and needed to appoint a new CEO, and he came to me and asked me if I wanted the job. And here it was. This is the big decision

Starting point is 02:01:16 of a life. Do I become the CEO and have this amazing continuation of money and career and security and everything else that is conventionally approved of? Or do I say, no, actually, I am not going to double down. I'm going to live the way in which I have been saying I wanted to with more freedom and more opportunity to do personal projects and pro bono projects and give back. And I had to 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,

Starting point is 02:02:05 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'm 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 will ever have. And if we give something up, we will just have less. What ends up happening is that we don't think about all the possibilities of things that could come up if we give ourselves openings to receive them. And so now, as opposed to having less than what I thought, I have way more because I have

Starting point is 02:03:10 all these new things that I'm doing that I never would have thought possible. Second, that hard decisions are only hard when you're in the process of making them. Once you make them, they're not hard anymore. Then it's just life and freedom. And it's an extraordinary experience that I really would 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's not the right decision for you, you can quit. You can do something else. It's not a permanent sentence necessarily. And also this is something that I've had to learn and relearn many times in my life, which is if it's taken you that long to make a decision, you probably don't and shouldn't don't want to and shouldn't do whatever it is that you're agonizing over with pro and con lists trying to justify in some fashion. It's in both of those points, I think are so, so important. 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

Starting point is 02:04:52 is you think you need, you're going to then up the ante and you're never ever going to be satisfied with whatever it is you think you need before you do something if it's not something that is real. If you think, oh, I need this much money before I do this, when you get that much money, then you're going to realize, oh, I actually think I need this much more. And it's just going to be this carrot in front of you that you're agonizing over trying to reach. And then the other thing is I'm going to quote Danny Shapiro here, the great writer Danny Shapiro, if you're 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. And she said what she felt was more important than confidence was courage.

Starting point is 02:05:40 And I fully, fully agree. Taking that first step, Confidence really only comes from repeated attempts at doing something successfully. But in order to take that first step, you need courage. And that's much more important than confidence. So for anybody that's waiting for the confidence to show up, take the first step in a moment of courage, even if it's aberrant courage to come full circle in this conversation. Such good advice. It reminds me of something that the brother, Kamal Ravikant, of another friend of mine, Naval Ravikant, told me. So Naval is a very, very successful entrepreneur and investor, among other things. Very, very good writer as well, as is his brother, Kamal,

Starting point is 02:06:21 who just had a novel come out. But Naval said to his brother, if I always did what I was qualified to do, I'd be pushing a broom somewhere. Well said. And I thought that was very, very encouraging. Touche. Debbie, I have so much fun every time we get to spend time together. Where can people find out more about you? Where can they learn more about your work? Where would you like people to say hello on social, if that? And I'll put all of this in the show notes for everybody. Sure, absolutely. I'm Debbie Millman on Twitter and Instagram.

Starting point is 02:06:54 You can see more about my program at the School of Visual Arts at sva.edu and debbiemillman.com, 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 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. the last year, aside from my episode with you, which I cherish, my episodes with Amanda Palmer, my episode with Alain de Botton, my episode with Krista Tippett, Nico Mouly, the great composer. Those are all episodes in the last year that I'm most proud of. Debbie, you're a rock star. Thank you so much for the time.

Starting point is 02:07:59 Thank you. Thank you. I really appreciate it. And to everybody listening, as always, you can find show notes, links to resources, all sorts of things that we talked about, and maybe more at 4hourworkweek.com forward slash podcast. And until next time, thank you for listening. Hey, guys, this is Tim again. Just one more thing before you take off. And that is Five Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the weekend? Between one and a half and two million

Starting point is 02:08:30 people subscribe to my free newsletter, my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is basically a half page that I send out every Friday to share the coolest things I've found or discovered or have started exploring over that week. It's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums perhaps, gadgets, gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast guests. And these strange esoteric things end up in my field and then I test them and then I share them with you. So if that sounds fun, again, it's very short, a little tiny bite of goodness before

Starting point is 02:09:13 you head off for the weekend, something to think about. If you'd like to try it out, just go to Tim.blog slash Friday, type that into your browser, Tim.blog slash Friday, drop in your email and you'll get the very next one. Thanks for listening. This episode is brought to you by Eight Sleep. I have been using Eight Sleep pod cover for years now. Why? Well, by simply adding it to your existing mattress on top like a fitted sheet, you can automatically cool down or warm up each side of your bed. Eight Sleep recently launched their newest generation of the pod and I'm excited to test it out, Pod 4 Ultra. It cools, it heats, and now it elevates automatically. More on that in a second. First, Pod 4 Ultra can cool down each side of the bed as much as 20 degrees

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Starting point is 02:12:31 prebiotics for gut health, an antioxidant immune support formula, digestive enzymes, and adaptogens to help manage stress. Now, I do my best always to eat nutrient-dense meals. That is the basic, basic, basic, basic requirement, right? That is why things are called supplements. Of course, that's what I focus on, but it is not always possible. It is not always easy. So part of my routine is using AG1 daily. If I'm on the road, on the run, it just makes it easy to get a lot of nutrients at once and to sleep easy, knowing that I am checking a lot of important boxes. So each morning, AG1. That's just like brushing my teeth, part of the routine. It's also NSF certified for sports, so professional athletes trust it to be safe.

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The Tim Ferriss Show - #750: Neil Gaiman and Debbie Millman

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