Debbie Millman is a writer, educator, artist, brand consultant and host of the radio show Design Matters. She joined Design Driven NYC in October of 2017 to share the story of her career, the origins of Design Matters (consistently one of the top design podcasts globally), and what she learned along the way.


Below is an unedited transcript of Debbie’s talk at Design Driven:

Hi, everyone. It’s so wonderful to be here, and I have to hand it to Dan for really being able to curate a thematic evening, because I’m going to be talking about my podcast. This is the caveat warning, because I’m going to take you through a history of the podcast. My show started, going on 13 years ago, so things were pretty raw when it came to what we were seeing on the internet. I’m Debbie Millman, and I have a podcast called Design Matters. Design Matters actually was created entirely by accident, entirely. People are asking me all the time now. The big question I get is, “How did you know podcasting was going to get so big? How were you ahead of the curve?” After you see this presentation, you will know that not only was I not ahead of the curve, I didn’t even know there was a curve. I’m going to take you through how this all happened in this really serendipitous way.

For anybody that does listen to the show, I think you know by now that I have a real fascination with the arc of life. How do people become who they are? What obstacles do they overcome? How do people make the choices to essentially become who they are? Not only do I like to quiz my guests about their histories and their circuitous arc to becoming who they are, but I’m also endlessly fascinated by what people want to become when they’re young, when they’re really young. I’m always asking kids, “What do you want to be when you grow up?” I’ve gotten a little bit concerned over the last year or two, because a frequent answer to this question is, “Famous.” I have a really hard time with that, because I don’t think that you can actually become famous. I think you earn fame, but I was …

I did ask this question recently to a young woman, a teenage young woman, and she had the best answer of anyone I have ever asked ever. It’s restored all of my faith in humanity. When I asked her what she wanted to be when she grew up, she looked at me without beating an eye, without missing a beat, and said, “Everything.” I love that, and I love the optimism and sort of the sense of purpose that you could be anything. I, on the other hand, did not grow up feeling like I could be much of anything. This is a drawing that I recently was given by my mother. She did what a lot of good old Jews do. She moved from Queens to Florida and considerably downsized, and when she did, she gave me back a bunch of things, a big box of things that contained report cards and book reports and all kinds of drawings that I’d made when I was a kid.

I came across this drawing, which I think is rather good, and I realized that when I was looking at it … I was about eight years old when I did this. … that somehow, without realizing it, I had predicted my entire future. Fast forward 40 years, and this is what I would be doing. Now, if you look at the drawing, there’s some interesting things in it. First of all, I’m a native New Yorker. I’m a native New Yorker. I was born in Brooklyn. Then, we moved to Howard Beach, Queens. I lived there until I was in the third grade. Then, from third grade to fifth grade, I lived on Staten Island, where my father had purchased his very own mom and pop pharmacy. I worked in his store on the weekends and in the evenings all through my adolescence and early 20s.

Then, my parents got divorced. My mom took my brother and I, and we moved to Long Island. I had that sort of typical horrific suburban experience on Long Island. My dad, I didn’t see for five years, and when I finally did see him again, he was living in Manhattan. For the first time in my life, as a teenager, I became really acquainted with Manhattan. Prior to that, I only really knew Brooklyn, Queens, and Staten Island. I was an outer borough girl.

This drawing has me in the middle of the streets of New York City, which I assume I was familiar with because of television and movies. There I am walking with my mom. My mom is wearing what I believe is a very popular Barbie outfit at the time, Tangerine Dream. There I am walking with her on the streets, and as a sort of young OCD designer, I labeled things. There’s a bank that says “Bank” and a cleaners that says “Cleaners,” and … Guess the gods have frowned upon us. …and there’s a bus and a taxi, and there’s a delivery truck. I don’t know if you noticed the delivery truck. The delivery truck says “Potato Chips” on it. You have to just sort of have faith in what I’m saying right now. I could be saying anything. You just have to believe me.

Speaker 2:                           We just have to [inaudible 00:05:18] We have to slide it.

Debbie Millman:               I don’t have a password. This is not my computer.

Speaker 2:                           Sorry. [crosstalk 00:05:24]

Debbie Millman:               Ah, there it is. Okay. There’s this green delivery truck, and it says “Potato Chips,” but what startled me, what sort of just staggered me, was that it says “Lay’s Potato Chips,” and at eight years old, I drew the logo. Now, fast forward close to half a century. I’m living in Manhattan. I take buses and taxis. I go to the cleaners. I go to the bank, and for most of my adult career, I drew logos for a living, and I drew all sorts of logos. I worked for over 20 years at a company called Sterling Brands, which I helped build, and my first 10 years of my career were not building brands or making anything of value. They were really what I would call experiments in rejection, failure, humiliation, and shame. I didn’t have any sense of what I could do, what I would do, how I could go about doing it, and quite by accident, fell into branding.

I was working at a design firm. The person that owned the design firm hated me. Never work for somebody that hates you, because it’s never, ever going to work out. Ever. I got a cold call from a person who was looking for somebody to fill a position in a branding consultancy. I went because I was desperate to get out of this other position, got the job, started working in branding. Probably because of my sort of unconscious, subconscious love affair with brands, as you saw, I suddenly found that I had this talent for branding. That was not until into my 30s, and I started working on some of the biggest brands in the world and designed the Burger King identity. This is the 7UP identity, the 7UP identity everywhere outside of the US. Pepsi owns the brand outside the US, so this is their design. Cadbury … Dr Pepper/Seven Up owns it in the United States, so it’s different and not quite as pretty.

The Hershey bar, Twizzlers. The type at the top, the totally twisted type, is a custom type that I made for them, so that’s one of my proudest moments, seeing that there. Häagen-Dazs, Tropicana, some of the biggest brands in the world, but over the years … Oh. Let me go back, because I don’t want to get ahead of myself. Because of that first 10 years that was so difficult and so despairing, when I found some success at Sterling, I dedicated everything to it. All the things that I had been doing prior, all of the illustration work, all of the dumb poems that I was writing, all of the things that I was doing to fulfill my soul, I essentially gave up.

From 1995, when I started at Sterling, until 2003, I completely abandoned all of my own self-generated work, everything. Not surprisingly, but 2003, I started to feel like I was living in a creative desert. Not that doing any of the work that I was doing wasn’t enjoyable and fun and profitable, but I felt that it was all about commercialism, all about capitalism, and that girl that had drawn that picture at eight years old was gone. The first foray that I tried to make into getting back to some sense of being a creative person again was writing for one of the first design blogs, a blog called Speak Up. One of the pieces that I did in 2004, around the election graphics of that year, went viral. It was the first time that anything that I ever did went viral. It went so viral, and you can see that there’s not an evident byline here. I had friends sending me this saying, “I think you’ll really like this,” and I’m like, “Yeah. I wrote it.”

But because it went viral, I suspect that this is the reason I got the second cold call of my life that changed my life. If there’s nothing else to take away from the presentation, take your cold calls seriously. The people that call you that want to sell you something might actually have something of value. I got a cold call from a fledgling internet radio network called VoiceAmerica. They were located in Arizona, and they called me, because they were interested in knowing if I would be interested in becoming a host of one of their talk shows, their live talk shows. I don’t know if you’ve ever seen cartoons with Bugs Bunny. You know how when Bugs Bunny gets really excited about something, his eyes sort of pop out and spin? That was what it was like for me when I got that call. I thought, “Oh my God. They’re offering me a job.”

Well, they really weren’t offering me a job. They were offering me an opportunity, and the opportunity was this chance to buy airtime from them. Then, they would produce a live radio show that they would air twice a week, once live, once a replay, on VoiceAmerica internet radio. Now, this probably will reveal just how desperate I was at the time, but I was making pretty good money, and I was feeling really, really creatively bereft, and so I decided, “Why not? This could be fun. It’s something different. I don’t know anything about it. I’ve never done anything like this before. If nothing more, I’ll learn something.” I signed on for 13 episodes to do a show that I wanted to do about design. They weren’t so sure about design, because this was part of the VoiceAmerica Business Network.

They wanted me to do what I was sort of semi-known for doing, which was branding, and I didn’t want to do that. That was actually the opposite of what I wanted to do. They were very skeptical that anybody would have any interest in design, but I was able to convince them, because it just so happened that that week, there was an episode of The Apprentice. Remember that? Yeah. We should have known. It was an episode of The Apprentice that featured … The exercise for the contestants was redesigning a package that I had designed, Pepsi Edge, and the design director of Pepsi was featured in the episode. I got VoiceAmerica to agree to letting me do a show about design, because I said, “Well, I can interview the design director at Pepsi, and so it’s sort of this combination of both.” They said, “Okay. Fine.” They sent me a contract. I had to sign the contract, and I started the show.

The show started February 4th, 2005. This was the … I warned you about the internet, about the internet typography from 2005. The show started in 2005. The show started with me … I had an office in the Empire State Building, so I was actually able to say, “Broadcasting live from the Empire State Building.” I was sitting at my desk in the Empire State Building with a landline. My guest was sitting across from me with another landline, and Arizona was connected through a modem. That’s how we taped the shows. Have you ever gotten on a line, a landline in your house, and then maybe your mom picks up the phone, and you hear that echo? Well, all … The first 100 episodes of Design Matters were taped with me hearing myself and the guests speaking with all of that slight delay over and over and over again.

My first guest was a man who ran design at Simon & Schuster. I invited him specifically because he’s a nonstop talker, and I figured if I was going to choke, he could take over, and I would be fine. That’s how the show started. That was the first show with John Fulbrook. Over the next 13 episodes, I invited more designers that I knew, friends, and then friends of friends. It seemed to be going well. I was getting good feedback, so I decided to sign on for another 13 episodes, and then another 13 episodes, and then another 13 episodes, and I kept doing the show.

got an email on July 2nd, 2005. Not an email. I’m sorry. This was a comment on Speak Up from a man named Michael Holdren. Michael Holdren, who I’ve never met and don’t know, changed my life. He wrote this. “Will there ever be an archive of your show? With the new podcasting … ” and I don’t know if you can see it here, but he spells it P-O-D, capital C, A-S-T-I-N-G. “With the new podcasting feature on iTunes, this would be a great opportunity for those of us who can’t catch the show every Friday to take it with us and listen to it when we have the time to do so.” I thought, “Why not? If somebody really wants to listen to the show that badly.”

I figured out how to upload my raw audio up to iTunes, and the show was born. It launched in October of 2005, and I started just randomly putting my show up on iTunes. There was no podcast section. There were maybe, maybe 100 different podcasts at the time on iTunes. Then, when the iPhone came out, here you could see how it looked on the iPhone. Two years in, this is how people started to begin to listen to the show when they weren’t in front of their computer.

Now, doing the show was not unlike working … Well, it felt like I was working with Wayne and Garth on Wayne’s World. The sound quality … There were times when we would take commercial breaks, because I was forced to take commercial breaks, where I could swear they were doing bong hits in Arizona. They would have lags coming back. I’d be sitting there waiting for them to come back. We’d have dead air. Anything that can will happen on live radio, and it did. As I started to put more and more shows up on iTunes, I started to see a fairly repetitive pattern in the reviews that people were leaving. This is a good example of one. “Great content, lousy audio. I love the content and the look inside the minds of so many brilliant people, but what’s with the audio? It’s terrible.” This would break my heart, because I knew the content was good, and I knew my conversations were interesting, but I didn’t know how I could do anything to make the audio any better.

Then, I got invited to bring the show to Design Observer. Design Observer was the second design blog after Speak Up that came into the market, and they invited … The late, great Bill Drenttel invited me to bring the show to Design Observer with the proviso that I improve the sound quality. I didn’t know how I would do that. I didn’t know anybody in radio, so he introduced me to a man named Curtis Fox, who was a producer for The New Yorker Podcast and for The Poetry Foundation. We agreed we’d start working together. We’ve been working together ever since, and he became my producer. This dovetailed at a time when I was about to launch the first ever branding program at the School of Visual Arts, a master’s program in branding.

Because I knew that there was some other little scattered podcast studios through the school, I asked the president of SVA if I could build a little studio in my program. He mercifully said yes, and after four years and 100 episodes on Voice of America, I moved into my own little studio, which is about the size of a shoebox, but it’s very intimate. That’s why I think I can get the quality of conversation that I have with my guests, and Design Matters went into Design Matters 2.0. Here, you can see we launched in 2009 on Design Observer.

I didn’t have a logo, so here I am working on Burger King and working on Star Wars and working on all of the biggest brands in the world, and because of that, I was vehemently opposed to doing anything commercial with my show. I didn’t want a logo. I just wanted to do this show that was full of passion and full of love and had no commercial value whatsoever. All Design Observer had was this really old, extremely young picture of me that they put up, and then they made that little square, because it would fit on iTunes in a way that sort of felt like it belonged.

I started interviewing more people, and the show grew. The show has continued to organically grow over the last nearly 13 years, but this is one of my proudest moments. I got a customer review. This is the first review you’ll see on the show’s feed on iTunes, because apparently, it’s the most helpful. It says, “I really appreciate the improved audio quality … ” This is from 2009. ” … in this new season of Design Matters. Debbie Millman ” blah blah blah. So that, I was like, “Okay. They hear. They know. It’s different.” Then, I started to get listener feedback. This has been the big surprise of the show, the letters, the art, the emails. It’s unbelievable. Not a week goes by that I don’t get something in the mail from someone that’s been impacted from the show, from listening to the show in some way.

I just want to show you some things. People do show notes, and they send them to me, really elaborate, wonderful show notes. I do a lot of live shows now, and this was an illustration that was done at the HOW Conference. It was posted on Instagram, and then I later found out that it was by Aaron Draplin. Everybody knows Aaron Draplin? Aaron Draplin did this illustration of me doing a live episode of Design Matters at the HOW Conference. This figures prominently in my decision to ultimately create a logo for the show, but in 2007, the show was nominated for a Cooper Hewitt National Design Award, which was somewhat surreal. We didn’t win. I didn’t expect to, but it was incredible that we were even invited to participate in this.

But then, in 2011, we did. We actually … We were up against the High Line, so I was like, “There’s no chance this is going to happen,” but then, somehow, it did. Then, I got to go meet this lady, who smells really, really nice. She’s beautiful. She’s really tall. We’re both … I’m wearing heels. She’s wearing flats, but she’s just absolutely divine, everything that you’d think she’d be. Then, this is the evolution of our logo, which I’m not really proud of, but it is what it is. This was 2009 to 2011. I was too busy to do 2010. 2012, 2013, 2014. Seeing a pattern here?

Then, I had Aaron Draplin on the show, and Aaron Draplin was so upset about the fact that I didn’t have a logo that he brought logos with him and showed them to me in the show, put me on the spot, showed them to me. He made these. He made these. He made these. He even made this. While I adore Aaron and thought that it was such a noble effort, I just felt like it wasn’t quite me, but I recognized the time had come. It had been nearly a decade of doing the show. I really needed to have something, and I remembered that about a decade before, I had won an auction for a fundraiser for the New York chapter of AIGA.

The auction that I won was an illustration by Christoph Niemann, and Christoph made me this. I thought, “You know what? Let’s do that,” and that became the logo. Armin Vit, who was the proprietor of Speak Up, who gave me my first creative opportunity when I was dying, he made me a website. I actually have a website, and now, two weeks ago, I launched a newsletter. I launched a newsletter. For the first time in doing the show all these years, I decided it’s about time, and so you can sign up. I don’t know when it’s going to come out. These kinds of things horrify me, but I’m going to try. I’m going to try.

What’s happened now over the years … It’s been, as I said, nearly 13 years, and the show had evolved. The show started as designers talking about design. It was really inside baseball, and the show has evolved to, again, as I’ve been doing this … I grew up as a podcaster in public. You can go back and listen to the early shows and be horrified, but over the years, in talking, I’ve done over 300 episodes now. The thing that I’m really fascinated with is, how does a person become who they are? How do we become alive? The show has evolved to a show not about designers necessarily talking about design, although I still do that, but it’s more about how creative people design their lives. How do they make the choices that they do and become who they are?

I still do quite a lot of live shows. This is at the National Building Museum in Washington. I do them everywhere and anywhere. People invite me … I go, done shows in Dubai. I’ve done shows in Pakistan. I’ve done shows at the Strand, at the Rizzoli. Basically, I’ll talk to anybody that has a really good story. I do a lot of videotaped episodes, as well. Milton Glaser, Malcolm Gladwell, Massimo Vignelli. After 12 years and over 300 episodes, Mattel made me a Design Matters Barbie, and LEGO made me a Design Matters LEGO, which, that was amazing.

Finally, 10 years after I started the show, iTunes recognized it as one of the best podcasts in Apple Podcasts, and that was really exciting. Every now and then, I pop up over Roman Mars, which is a rarity, so of course, I screen grabbed it, and now I show it to everyone. Then, you can still see that silly little archive of my first hundred shows, which, as I said, are really embarrassing, but I think it’s important, because one of … I was asked to sort of share some of my learnings, and my learnings, one of my most important learnings is that I think anything worthwhile takes a long time, and it took me a long time. It took me a decade, really, to understand what I was trying to do and the kinds of stories that I was trying to tell.

This is a fun story, because I, my newsletter not withstanding, I’m a bit of a Luddite. I didn’t realize on Facebook that you could get emails from people you don’t know. There was a number. I didn’t know what it was. One day, I saw it. It looked like it was like a hundred and thirty-something. I thought, “Let me see what this is.” I go in, and on May 12th, 2016, I got this unsolicited email on Facebook from the director of Hamilton. Now, if you remember back in May of last year, it was like Hamilton craze. I get this, and I, like, lose my breath. I can’t even think. It’s not possible that this is happening, but I saw it on September 16th, because I didn’t know that I was getting these dumb emails. I did write back on September 16th.

At the time, he was very sweet. He wrote back to me, and he said, “Well, Tommy’s now in Chicago launching Hamilton in Chicago, so call back in a few months.” Called back in a few months. “Oh, Tommy’s now in LA opening LA,” and then, “Oh, Tommy’s in London opening London,” and then, finally, “Tommy’s back, and he’d love to do the show.” Last week, I launched my 13th season with Thomas Kail, the director of Hamilton. This week, I had my second show of the season with Brené Brown. Here, you can see some of the people that I’m interviewing this coming season, including Marina Abramović. I’m very excited. I’m really tempted to just sit there and do nothing for the entire hour. Conceptually, I think that would be really interesting, but I don’t know that anybody would really listen.

Here. I have learned a lot. Over these 12, 13 years, I’ve learned a lot. The first is that we … This is all art created by people that have listened to the show, that have heard me talk about these things, and have created artwork on Instagram or Twitter or Facebook and sent it to me. We’re living in what I call a 140 character culture. We expect everything to be immediate, and I think because of the extraordinary designers working in our business, people like Jessica Hische, Jessica Walsh, who make so big before they’re 30, that there’s this pressure that if you aren’t on this path to success before you’re 30, that there’s something wrong with you. I’m here to tell you that I didn’t even start the first part of my career success until I was 33. I got my job at Sterling when I was 33. I started Design Matters when I was 45, so everything worthwhile takes time. Anything worthwhile takes time.

I also think that if you’re not doing the kind of work that you want to be doing in your own practice, if you’re working for a design firm or a consultancy or a corporation where you’re not being given the kind of work that you want to be doing, as … I liked the work that I was doing at Sterling. I just didn’t feel like it was fulfilling something bigger that I wanted to somehow accomplish with my life, and I still don’t know that I’m doing that, but at least I feel like I’m a little bit further along. Self-generate your own work. Do something where you don’t have to ask anybody’s permission to do anything. If you think you’re too busy to do it, then I contend that busy is a decision. We make the time to do the things that we want. We don’t find time. We make time, and if you want to do something more than what you’re doing, you have to decide that you want it enough to be doing it.

A lot of people tell me that they have no confidence, and they don’t think that they can do something, because they don’t know how to do it. Dani Shapiro, on one of my shows, the great writer, Dani Shapiro, said that confidence is overrated. I was super interested in that, and I was immediately intrigued. What does that mean, confidence is overrated? What she felt was more important than confidence … She felt that most overly confident people are kind of obnoxious and unlikeable, and I kind of agree. Maybe it’s just jealousy, but I agree.

But what she felt was more important than confidence was actual courage, was courage to actually take that first step in doing something that you don’t know how to do. I started thinking about that. Well, if you are able to muster the courage, and you take that first step, sort of like Indiana Jones in Temple of Doom, you know, you just take it and hope that there’s something underneath your foot, then what happens? How do you build confidence? I’ve been thinking about this nonstop, and I think I’ve come up with, I think, a fairly accurate definition of what confidence is. Confidence is the successful repetition of any endeavor.

How many people here know how to drive a car? Okay. How many people here, the first day they drove the car, got into the car when they were learning and had somebody in the passenger seat teaching them, turned on the ignition and were like, “Woo hoo. Car trip. Road trip.” No one. Okay. Now, you get into the car. Does anybody ever think, like, “I’m going to get into my car now, and I hope I don’t kill someone”? No. You all have car confidence. We all have car confidence. We’ve done it enough times so that when we turn on the ignition, we have this sense of, we’ve successfully … We have the successful repetition of driving our car, and therefore, we have confidence. That comes over time. You can’t expect that anything that you do is going to be good the first time you do it. When we learn to walk, we can’t even do it without falling, so why would we be able to do anything else? That’s a part of the big reason I keep all those old horrible shows up there, so I can tell people, “You can grow up in public, too.”

Then, in order to strive for a remarkable life, I think you have to really decide that you want one and make that choice to make one and not to be afraid to want a lot. We’re all capable of doing that. Then, my big question now that I’m in my mid-50s is, as I watch the time and realize that I probably have more years behind me than I do in front of me, that if there is something that I want to do, I need to start thinking about doing it, because if not now, then when? I’ll leave you with my sign off. I end all my shows this way. We can talk about making a difference, we can make a difference, or we can do both. But I also think that we can talk about making a difference with our lives, we can make a difference with our lives, or we can do both. Thank you so much.

Oh, questions. Any questions?

Speaker 3:                           [inaudible 00:31:12] Any questions? I’ve got a mic.

Debbie Millman:               Yes. This lovely, fearless gentleman is asking the first question. Want to come speak into my neck? I guess not.

Speaker 4:                           Those people at Voice … I’m sure you were working at just a design office doing logos and [inaudible 00:31:41] How did they know that you could speak with such lovely voice, vocal power?

Debbie Millman:               They didn’t. I think they just wanted people to pay them. Seriously. This was not something that was that hard to get. I think their standards were extremely low, but also remember, this was 2004 when they first reached out to me, and internet radio was just sort of a glint in someone’s eye. There wasn’t a lot happening. I mean, if you think about it, between 2001, when the iPod was first released, and 2005, when Myspace took over, … Anybody remember Myspace? … that we were living in that time in what cultural anthropologists were calling an isolation nation, where psychologists were saying that the iPod was essentially depopulating social space for us. We were living with social animi.

What was happening in that time was really … We were doing basically four things online. We were emailing, we were playing games, we were shopping, …You know, when the J.Crew Catalog came out, our heads exploded, because we could buy things online. … and pornography. That was pretty much it, so when the internet radio thing started, I think there was really very little criteria for success. I think it was like, “Who’s willing to pony up?” and I got lucky.

Speaker 4:                           Well, this is going to sound … Why you among the 10,000 different designers who were doing similar things?

Debbie Millman:               I have absolutely no idea.

Speaker 4:                           Mm-hmm (affirmative).

Debbie Millman:               There was absolutely no reason for me to do that. It wasn’t like I had a LinkedIn profile that featured the DJing I had done in college, because I didn’t.

Speaker 4:                           So you got lucky?

Debbie Millman:               Yeah. It was completely, complete serendipity. It’s a cold call, a cold call.

Speaker 5:                           Hi.

Debbie Millman:               Hi.

Speaker 5:                           What’s your process on inviting guests, like on inviting them to your show?

Debbie Millman:               I invite guests that I really want to have a conversation with, and over the years, I’ve gotten really good at figuring out emails. Most of the time, I’m soliciting them. Occasionally … Tommy Kail wanted to come on the show. It was like, “Roll out the red carpet for Tommy.” That happens more now. I mean, I get a lot of emails now, a lot of emails about people that want to be on the show, but part of, for me, the beauty of being able to do this show is talking to people that I am really intrigued by and really admire and want to understand who they are. I’ve even stopped doing the show remotely. I very rarely … I used to do shows from studio to studio, so somebody’s remote.

When I did the show with Krista Tippett, she was in her studio in Minnesota. I was in a studio in New York City. I think it was a good show. She talked very deeply about a depression that she had gone through, and we were really talking very vulnerably about both of us going through a depression. Because I wasn’t seeing her, I think I missed a really important question that haunts me to this day. I didn’t ask her how she was able to overcome her depression. We just sort of moved to another part of the conversation, and then that was over. Afterward, I was like, “I missed it.” Because, I think, I wasn’t there sort of in … When I do the show, I’m sitting here, and my guest is sitting here, and we’re facing each other. There’s nothing between us, and I never leave their face. It’s very intense, and so I think that that is where I can get at the sort of heart of a person, literally and figuratively.

It just comes from asking, and I ask, and I get a lot of noes, and I get … Actually, I don’t get a lot of noes. I get a lot of crickets. I’ll send an email, and then I’ll hear nothing. Occasionally, I’ll get a no. Junot Díaz keeps saying no. I keep emailing him. Roxane Gay said yes. Then, we couldn’t work out the schedule. Then, she said no, but I’ll keep doing it. Marina Abramović canceled a few times, but I think she’s coming November 9th. It’s just a matter of …

I rarely will take no for an answer, but I don’t want to be obnoxious, so I just keep gingerly, every couple of months, writing again. Junot has now heard from me about three times. I think he knows by the fourth time, he better say yes. It’s really just a matter of that, but my guest list has broadened, so I reach out to scientists. I reach out to artists. I reach out to writers, musicians, people in the theater. I’m really interested in anybody that’s doing something creative and trying to make something sort of with their hands, literally and figuratively, both. Yes, and then … We’ll do one and then two? Is that okay? Okay.

Speaker 6:                           Okay. I’m kind of interested in how you have overcome imposter syndrome, so you [crosstalk 00:36:43]

Debbie Millman:               That’s assuming I have.

Speaker 6:                           But I know you’ve moved into fields that … You know, maybe when you moved into radio or [inaudible 00:36:50], how did you just start that and feel … How did you gain the confidence that you needed to switch modes? [inaudible 00:36:59]

Debbie Millman:               That’s a really good question. With branding, branding is the only thing I’ve ever come to and felt like I had a natural talent, like somebody who can run fast. You just start running, and you went, “Wow. I run faster than everybody else.” That never happened to me. I never even ran. I was too … You know, I was the last girl chosen for the dodge ball team, always. Because I think of my history, working at my dad’s pharmacy, I had this talent. I had this insight into why people buy the things that they buy. That first bit of success was something that I was so grateful for that I dedicated everything to it, everything. As I said, I gave up everything else, because wow, I could do something well, and I’m just going to do it all the time and try to feel good about myself that way.

As far as almost everything else, I don’t think … With the way that the show has grown, when I see the downloads, and I see that millions of people are listening to the show, I feel like it’s a mistake. I feel like this is a dream and that I can’t believe that this is possible. I think, basically, I’m saying I haven’t gotten over mine imposter syndrome, but what I can tell you is because it did take a really long time, I never take it for granted. I feel just incredibly grateful in addition to feeling incredibly lucky. That’s why I always take cold calls from people.

Speaker 3:                           [crosstalk 00:38:32]

Debbie Millman:               No. There was a woman here.

Speaker 3:                           [crosstalk 00:38:33]

Debbie Millman:               Yeah. There’s a woman right here, and then right there, but she was … She had her hand up first. Is that okay? Because she was waiting from the previous person.

Speaker 3:                           [inaudible 00:38:41]

Speaker 7:                           [inaudible 00:38:44] something else over a couple things. How have your conversational skills evolved over the years? I’m sure you also get really nervous at times.

Debbie Millman:               Oh. Yeah.

Speaker 7:                           [crosstalk 00:38:53] Do you get a lot of that? I know a lot of people do have anxiety over stuff like that, …

Debbie Millman:               Yeah.

Speaker 7:                           … the initial conversation with someone they admire.

Debbie Millman:               That’s a great question. It’s a great question. I think a great conversation is like a game of pool. This is what I’ve learned. You not only want to get the ball in the hole. You want to have all the other balls on the table to be able to get those in the holes, too. You need to be prepared. The first hundred episodes that I did, I had somebody helping me do my research, because I had this big full-time job, and I wanted help. I had somebody that was helping me with research. It wasn’t until I started to do my own research, and it takes hours … I spent, this past weekend, I think 18 hours of research on the guest that I interviewed yesterday.

Because I do it myself, I feel like I can have a conversation, and they can pivot, and I could go with them, because I’ve done enough research to know where they’re going to go. But when I first started the show, I would talk. I would wait for the other person to stop talking, and then I would start talking again. I wasn’t even really listening to their answers. I was so desperate to make sure I asked the questions that it wasn’t a conversation. It was just like tennis, like question, answer, question, answer. Sometimes, they had nothing to do with each other. It was sort of like a presidential debate. You’re just sort of saying what you want to say despite the question or the answer.

I’ve learned to really listen, which is why it’s also important for me to be with the person, because when you’re not face to face, I find that other things can easily distract you and sort of take you’re mind elsewhere, but if they’re there with me in the room, I am completely focused and just fully, fully listening. But I also think it comes from having a bit of confidence at knowing that I’ve done enough research so that no matter what they say, I have something that I could add value to and continue the conversation. The only times that I really get nervous …

get nervous when I’m super, super, super sort of in love with the person, and then I get … Like, Maira Kalman. No matter how many times I interview her, I will always be nervous. I can’t get over it. I just find her to be so remarkable, it’s hard for me to even think straight. But with most interviews, I feel like, and because I have all the research and all the knowledge, I feel that once I’m there with the person, it just becomes me in the conversation with the person. It becomes this collaboration. It stops being a conversation and starts to be this sort of thing that we’re creating together.

Speaker 8:                           Hi, Debbie.

Debbie Millman:               Hi.

Speaker 8:                           As somebody who’s starting to get a little bit of gray in his hair, thank you for acknowledging that there’s still some time left for me. That’s heartening, but being here with some people who are just starting, maybe, the first 10 years of their journey.

Debbie Millman:               I’m sorry. Yeah.

Speaker 8:                           How do you make the most out of that part of …

Debbie Millman:               I think that what I can tell you is just what I wish that I knew. Know that in your 20s, you can make a lot of mistakes. People kind of expect that you’re going to make mistakes. And experiment. If you’re not making enough mistakes, you’re probably not taking enough risks. I think that risk is such a hard thing to do. Thinking about design and branding, the only people that really like … You know, when Peter was talking about the WNYC design, the only people that really like those changes are the ones making the changes. Nobody else thinks, “Tropicana’s redesigning? Yoo hoo. Let’s go buy it. Let’s try it for the first time ever.” No one does that, because … The reason we have these takedowns of logos, because we hate change. We feel threatened when we’re experiencing anything that’s uncertain. That’s sort of what Seth Godin calls the lizard part of the brain, gets ignited, and we get scared, and we worry that we don’t have control, as if we really did to begin with, but …

If you are doing things that you’re not sure you could do, you’re probably on the right track. If you’re looking to do something or take something because you’re afraid you’re not going to get anything better, you’re probably settling, and I settled. In my 20s, I settled. I was so worried about being self-sufficient, and I was so worried about being able to pay my rent. I just did whatever I could, because I thought I was unemployable, and I thought I was unemployable through my 30s and into my early 40s, that if this didn’t work out, I would be a bag lady on the street. Then, I think over the years, you begin to realize that you can actually rely on yourself. What I would tell anybody in their 20s, to dream as big as possible. If you feel like you can’t do it, do it anyway.

I’m going to share a great anecdote about Barbra Streisand. Trust me. It’s a good one. I was reading an article in The New Yorker a couple of years ago about Barbra Streisand, and it was an article that was also about performers and stagefright. Barbra Streisand’s manager was, or some one of, what, her handlers was interviewed, and they were interested in understanding her appeal and her longevity. They got to talking about her talent and how she’s an actress and a director and a singer and, you know, just so many things, and she’s been doing it for six decades. Well, this manager said that that really wasn’t her biggest talent. Her biggest talent was doing all of those things for all these years with debilitating stagefright, and that she was doing it anyway, because she had to. She had to. She had no other choice. This was her non-negotiable. This is what she was doing.

Last summer, I went to see Barbra Streisand at the Barclays Center, and no one wanted to go with me, so I went by myself. Because I was by myself, I had a lot of time to witness and observe, and I’m looking around and watching people. For whatever reason, I suddenly look all the way up, and the ceiling is like three or four times as high as this. Deeply embedded in the lights is a teleprompter with all the words to all of her songs and all of her talking points. Everything was there. Now, I could have gotten up on the stage and sang all of her songs without the teleprompter. She needed her teleprompter. She was doing it, even then, in her 70s, with stagefright, and there it was, up there. I saw it, and I was like, “Wow. That’s amazing. That’s just an amazing thing, that she’s doing this anyway.”

You have to decide what is more important, fearing something and fearing that rejection and fearing the failure or having regret at not having done it. Which would you rather die of? You’re not going to die of the fear. I’ll tell you that right now, and that, I can tell you this from branding. We metabolize everything really quickly. We metabolize all our purchases really quickly. As Dan Pink would say, if a flat screen TV is your idea of happiness, it’s a fool’s game, because you’re always going to want a flatter, bigger one. We all know that when we buy our devices, it’s just a matter of time before we want the next device.

We are able to metabolize our feelings of rejection, our feelings of sadness. It might take a while, but we are able to metabolize them, and then we can resynthesize what we think we want. For those of you that are in your 20s, please avoid that decade that I had. Make mistakes. Fail. Fall on your face. Cry. Do whatever it takes, but make sure you try to do what you really want to do, because it’s the easiest time to be able to do it, when you’re still young and beautiful.

Audience:                           Woo. Woo.