3 Clips Re-Air: Design Matters with Debbie Millman

3 Clips Re-Air: Design Matters with Debbie Millman
3 Clips Re-Air: Design Matters with Debbie Millman

Feb 09 2023 | 00:54:01

Episode February 09, 2023 00:54:01

Hosted By

Stuart Barefoot

Show Notes

Since Audience is between seasons, we’re offering up a great episode from our 3 Clips archives. Today’s episode features an episode originally published in 2021 and highlights the first podcast about design. Ever. In this interview, host Jay Acunzo and Debbie discuss how she got started as a host, what’s kept her going, and why her research documents for each and every guest can be as long as 70 pages.

Debbie Millman started her interview show about design as a radio program to fulfill her need to explore her own creativity. That was 16 years ago, and Design Matters has been in production every since: it’s the world’s first podcast about design. Debbie has welcomed over 500 guests to her now wildly popular podcast to explore creative culture and how some of the most influential thinkers, artists, musicians, writers, and designers create their work, career, and life.


3 Clips is a Castos Original Series. Castos provides tools for public and private podcasts and believes podcasters should own their turf to provide the best possible audience experience. Visit http://castos.com.  

If you have any questions about this episode or want to get some of the resources we mentioned, head over to Castos.com/podcast. And as always, if you’re enjoying the show please share it with someone who you think would enjoy it as well. It is your continued support that will help us continue to help others. Thank you so much! Never miss another show by subscribing at castos.com/subscribe.


Debbie Millman and Design Matters can be found here

Follow Debbie Millman on Twitter @debbiemillman

Follow 3 Clips host Jay Acunzo on Twitter @jayacunzo

From Play It Forward: This week’s recommended podcast is The Lisa Congdon Sessions

This episode was produced by Cherie Turner: learn more here

Theme music provided by Cardboard Rocketship

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Castos, private podcast: https://academy.castos.com/privatepodcast/ 

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Clubhouse video: https://www.youtube.com/watch?v=8729ZpWpmIw 

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Episode Transcript

Speaker 0 00:00:00 Hey, it's Stuart. As you know, we're between Seasons on audience, so it seems like as good of a time as any to dive back into our archives and listen in on an old Three Clips episode, which is one of our other shows. If you're not familiar, this episode is first published in July of 2021 and features the Podcast Design Matters, which was the first podcast ever about design. It was hosted by Jay Alonzo and was produced and edited by Cherri Turner. You can go to three clips podcast.com or anywhere you get your podcast for more episodes. Enjoy. Speaker 1 00:00:35 16 years ago, I viewed creativity a whole lot differently, and I kind of wish someone pulled me aside and said, hold on, young sir. Think of it this way. Instead. 16 years ago, I thought you had to be a completed product to justify creating any great thing that moves people. I thought it's the experts who have something to say who have earned the right to make important things. So why 16 years? It's a bit of a random number, right? Well, 16 years ago is when today's guest launched her podcast, a show that's been running consistently ever since and over those 16 years. Thanks. In no small part to this guest today, I've learned a certain truth about creativity that's changed how I see the work. Rather than act like experts, we can act like explorers. 16 years ago, I never thought of it that way, but today's guest, it seems very much did. And whereas most of the world hadn't heard of podcasts 16 years ago, that didn't stop Debbie Millman from Launching Design Matters, and she embarked on a journey to understand how the world's most creative people build their careers and their lives. Today we go on a journey to learn how this show started, grew, and evolved into one of the crown jewels of audio from its humble beginnings 16 years ago. Speaker 2 00:01:51 I, this is three clips. Speaker 1 00:02:09 This is three clips. We're a Casto original series, and as always, I'm your host, Jay Azo. I'm an author, a speaker, and the host of the podcast Unthinkable, along with this fine show and on this fine show, we believe that creativity unfolds in the minutia. It's not about going big, it's not about throwing resources at the problem, it's about resourcefulness and the craft. It's the micro moments, the tiny techniques, and the refreshing wrinkles that all add up to create something that we love, which means we can all go and try to create the shows like the ones we admire most. Given that belief, we invite podcasters we admire to come on this show and deconstruct their best work and demystify the creative process a few little pieces at a time. Today we talk to the great Debbie Millman. She's a longtime teacher having founded the world's first and now longest running grad program about branding, and that's at the School of Visual Art in New York. She's a chair of the board for the Joyful Heart Foundation, a prolific creator and speaker, an author, and a true OG in the world of podcasting. The show has had multiple homes and lots of steps to evolve over the years, and today the show is part of the Ted Audio Collective. Speaker 1 00:03:22 So, we'll, we'll d dive into the clips in a moment, but I, I did kind of want to just let our listeners meet you up top. And I, I think the way, what I'm fascinated about in podcasting among millions of things is the way a host and an interviewer sees the world can provide this really interesting and compelling lens through which an interview is conducted. So maybe it sounds at first glance, like this is another interview show, but because it's your show, Debbie, something pops out the other end that makes it inevitably unique. And I know at one point you applied to Columbia Journalism School and it wasn't meant to be. So, uh, you wound up at a rock magazine as a design assistant, and so away you went into design. You've worked with countless executives and marketers and students around branding. So you have this smattering of experiences in your career, and I'm wondering how you think those experiences show up when you approach an interview and how that informs or changes the interview to be an original. Speaker 3 00:04:21 Well, because I struggled so much early in my career to sort of find my place in the world, I am really endlessly fascinated by other people that have had those experiences. And I think what I've found after 500 or so interviews is that everybody has those experiences. And so I really like to understand how people have overcome their own hardships or how they handle their own insecurities or self-loathing or doubts and do it anyway. And I think that that's an invaluable thing for people to know and something that I'm never tired of asking about it. <laugh>, Speaker 1 00:05:09 You sort of headed me off at the past in a really helpful way, actually. You said you're never tired of asking about it. You also said through 500 some odd interviews, so, uh, the show's been running for 16 odd years. 16 years. Can you take us back to when you were thinking of starting the show? What was different then? What was it like then? Why get into this thing that, uh, most people would've said, wait, what now? Speaker 3 00:05:33 Well, I didn't intend to, this wasn't an intention. This wasn't a life goal. This wasn't on my list of things that I wanted to do in my life prior to starting it. At the time, I, I first started putting the show together. It was 2004, and at that point I had been working at the brand consultancy I was then at for almost a decade, and that was a company called Sterling Brands. I was the president of Sterling Brands, one of the three partners. And I, my experience in branding, which began a few years before Sterling at another company, uh, which became Interbrand, was my first foray into doing anything successfully. You already mentioned my being rejected from the Columbia School of Journalism, and there were countless other things that I was trying to do through my twenties and thirties that were, um, similarly <laugh> responded to <laugh>. Speaker 3 00:06:34 Um, and so without any real understanding of how or why I was very successful on branding, um, I don't know if it was because of my early experiences working in my dad's pharmacy, doing customer service and the cashier and signage and whatever else, but there I was for the first time in my life, in my late thirties, early forties, finally successful at something. And in that time, because it was so intoxicating and so new for me, I essentially abandoned every other side hustle, creative endeavor that I was doing. And I was doing a lot of different things on my own. Um, and so I gave up all the drawing I was doing, all the writing I was doing stopped even journaling. I was doing a lot of textile work at the time. Stopped doing that and, and just put every bit of energy into this job that I was successful at, which just made me more successful at, and it was incredible. Speaker 3 00:07:38 It was the first time I was making any real money. I bought an apartment. Um, it was, it was really quite a special time in that I found a path. But after about 10 years of doing it, I really started to feel that I was losing that creative spirit that I had. Everything that I was doing was commercial. So it was all about a return on an investment and shareholder value and shelf presence. And I, I felt that there was a fundamental part of me that was starved. And so I started to dip my toes back into doing some writing on some design blogs and various other smaller entities. And then I got a call, a cold call from an, uh, an internet fledgling internet radio network called Voice America. And they, what I thought they, I thought they were offering me a job as a radio host. Speaker 3 00:08:33 What they were doing was really offering me an opportunity to pay them to produce my own sort of vanity show. And I was so starved for any kind of creative outside the office, any creative inspiration that I, I decided to sign on. I had, I had the money to do it. It was, it was a lot of, of money, but not so much money that it was gonna bankrupt me. It was, I think $5,000 and for 13 episodes. And so I decided to do it. And I also felt that at the time I could actually incorporate some of my business connections in the guests that I chose to speak to mm-hmm. <affirmative> and decided to call it Design Matters, despite the, the pushback from Voice America. They really, it was on the Voice America Business Network, and they really wanted me to do the show entirely on branding, but I didn't wanna do that because of my need to try to, um, have this Hail Mary with my creative spirit. Speaker 3 00:09:32 Yeah. And so I, I insisted and then, and won the argument to call it Design Matters, and started the show February 4th, 2005 with my friend John Fulk, who I asked to be on the show because he's a really charming, charismatic, um, very outspoken person. And I thought, well, if I get so nervous that I choke, kind of take over. And, and all the shows that I did in those early days were primarily with people that I was friends with, that were designers. So it was very much inside baseball designers talking to designers, kinda thing. The big difference between then and now, <laugh>, well, there's so many, but when I started the show, I was doing the show face-to-Face with people sitting in my office, which happened to be in the Empire Skate Building. So I could say, uh, broadcasting live from the Empire Skate Building, which was fun, not Speaker 1 00:10:24 Too bad. Speaker 3 00:10:24 Yeah. Um, I, I had to sit across from someone and we both held telephone handsets as if we were talking to each other on the phone, which we essentially were. And so there was that awful echo that you get when you're in the same room talking to somebody on the same telephone line. Um, so I had to sort of ignore that, but that was then pressed through this modem. And so the sound quality of those early shows is really quite horrendous. Um, so that's one of the big things that's different between then and now. Speaker 1 00:10:58 So obviously a lot has changed technically and, and a lot more, um, 16 years doing this show. What keeps you going? Why are you still going at it? Speaker 3 00:11:06 Well, I love it. I really love it. And that's not, I, I'm a person that once I commit to something, I tend to stick with it for a very long time. I was at Sterling for 20 something years. Mm-hmm. <affirmative>, I'm now at s v A for, uh, fif I've been teaching for 15 years. Uh, some of that overlapped. I'm not 110 <laugh>. Um, so, and I've always liked to do a lot of things at once. It was just this one period of time from 1995 until the early to mid two thousands that I really did narrow that focus. Other than that period of time in my life, I've always done numerous things at once and have continued to do that now. So I just am a person that really likes to, um, stick with things. Speaker 1 00:11:51 When you see so many interview shows cropping up, um, many of whom might be trying to book similar guests to you over the years and the world floods with that, do, do you start to wonder, do I need to change? You know, is this r i p good times? Like, are, are you looking sideways at all at what's happening around you? Or are you just as we will hear from a guest that we will be deconstructing an episode from, are you merely doing the work? Are you putting your head down and just saying, I love this show. I don't care what's going on around me, I will persist. Cause I do think the sort of competitive set a podcaster occupies has a way of throwing off what some hosts that we've talked to try to do. Uh, did that ever plague you at all? Speaker 3 00:12:32 It's such an interesting question. Well, sometimes I get envious of other people that book, you know, people like Michelle Obama or Barack Obama or Hillary Clinton, or people that I really would love to speak with. Um, but I also feel like why would they wanna come and talk on my show? So it's not like I think I deserve that they belong on Design Matters. It's just more like, wow, I'd love to talk to her. Um, so, so yes, and I, it's really a tough question because I've evolved the show as I've evolved and I feel that initially my, my focus was on design because of my interest at design. And then after doing the show for say, I don't know, eight or so years, I started to get inquiries. I, I started to get the, the people calling me to be on the show. And then when they were beyond designers, or when I reached out to somebody that was a creative person, but not necessarily a designer, I would get a yes, I would love to be on the show. Speaker 3 00:13:43 And so it very organically evolved and it's continued to evolve as I evolve and as I have gotten more recognition, I've gotten more opportunities to interview people that I really admire. And so those are the artists and the filmmakers and the performers and the directors. It's still very much a creative show. How do people, how do creative people sort of design the arc of their career and their work and their lives? Um, um, I still feel that the, well, I can't say I still feel, cuz I don't know that I ever specifically didn't feel <laugh>. Um, I feel very confident in my own research skills. I do so much work before a podcast that if somebody is able to do that too, God bless him, <laugh>. Speaker 3 00:14:44 Um, and I listen to, so, uh, I I wanna say beyond, listen, I not only listen to so many shows. I, when I'm interviewing somebody that's been on, you know, Dak Shepherd or Tim Ferris or, uh, this American Life or Fresh Air, I transcribe those shows. I have them transcribed and do it myself, and then I read them because I don't wanna ever ask the same questions that those interviewers ask and may ask great questions. I mean, Tim Ferris and Dak Shepherd are just, you know, Howard Stern. They're great interviewers. And so what I try to do is look at the answers and then ask questions about those. Speaker 1 00:15:23 You know, I, one of the techniques I really appreciated from you, and it helps me get lost in the interviews cuz I think people do have a tendency to gravitate towards names. They know in, in a moment we're gonna dissect three clips from an interview. You've done your third interview with Seth Godden. So there's an example, huh? Speaker 3 00:15:38 Excellent, Speaker 1 00:15:39 Excellent. Yeah. And I know you guys have great rapport. There's a lot there. Uh, but you, there's something I've noticed and appreciated, which is you do go back and cite specifically what shows up in their work or what, what they said publicly elsewhere, what they were asked, what they said, and then you kind of take them to a missing piece, a new angle. It's very, um, generous because you're, you're like letting them expand on stuff that maybe other shows didn't. Because so often we have to touch on the surface of things for runtime purposes. Um, did you borrow that from someone? Do you, you mentioned a bunch of interviewers that you admired. Do you feel like you've, you've grabbed at different things that you admired or did that come out organically af was that hard one and learned over the years? Speaker 3 00:16:21 I think it was hard one and learned, um, mostly because I was also hearing the same questions asked over and over. And so because I listened to so many and transcribe so many, I would, I would see that repetition. And that's also why I don't say, and so you said on this American life or on being on, on being or Fresh Air or whatever, I don't, I don't cite the specific podcast because it might be several that they've spoken about this issue. And I don't want to say, well, you said on all these three podcasts or whatever. And not to say that those podcast hosts are lazy in any way and, and ask the same questions. They all ask it in their own special way. And that's why I, I listen to so many and transcribe so many because they are all sort of coming from a different place. And so then I aggregate all of that, fill in sort of my arc of a person's life and then ask where I see the little bit of, um, white space, Speaker 1 00:17:26 Right? You're looking for those cracks of daylight and it, it shows, it, it shines through. Um, let's get into the clips. So I mentioned we're gonna dissect some clips from your November, 2020 interview with Seth Goden, the third interview you've had on the show with him, which I found fascinating. And at the moment in time that you talked to him, you know, certainly the pandemic was raging and there's a lot else going on in the world in society, in American culture and politics. Um, but also, also he was in the throes of promoting his book, the Practice Shipping Creative Work. Um, so there's, there's a lot of nuance when it comes to talking to somebody who is appearing almost everywhere you can possibly appear in a niche because of a book or because of a name like Seth Goden. So we're gonna get into that. Um, the first clip, however, is a lot simpler. Um, and we're gonna touch on why we picked it, but it comes almost at the very beginning of your interview after a couple short little, hi, how are you? Hello type questions. Um, so let's just roll the clip and see what we can make of it. After Speaker 4 00:18:21 Listeners of my show know that I like to take a long journey into a person's life and a sort of classic Design Matters interview. And we've sort of done that twice now in our previous interviews in 2014 and 2017. This time I get the great good fortune of a deep dive into your brand new book and the book is so good. And I've told you this already, but I'm gonna say it again for my listeners that it's pretty much all I wanna talk about. I highlighted and noted so many topics in this book. I, for the first time ever in my life, surpassed the amount the Kindle lets you export. So it's the first time in the history of the show, in the history of my life, um, that I've had to do that I had to buy two Kindle copies <laugh> from two different accounts so that I could highlight and take notes on everything I needed. Um, I think that I highlighted about 23% of the Speaker 5 00:19:17 Book <laugh>. I'm so moved by this. You're a hoot. Speaker 4 00:19:21 I am a hoot <laugh>. I even talked about this book on another podcast that I did earlier in the week. So as I mentioned in my introduction, your new book is titled The Practice Shipping Creative Work. So before we talk about the title and the topics, let's talk about the number book number 20. Speaker 1 00:19:43 Debbie, what did you first notice about that piece when you heard it played back? Cuz it's, it's been a few months now. Speaker 3 00:19:49 I spent too much time talking about the stats. <laugh> interesting. Should have just gotten right faster into the, into the, I didn't need to tell everybody that much detail about how much research I had done. So yeah, that was a little overkill. Speaker 1 00:20:04 It's funny when I that's, I, I didn't used to, we can share inside details cuz everyone listening as a podcaster, I didn't used to just hand the baton right away to the guest to say, what'd you make of that piece? But since I've started doing that, most people are self-critical. I I felt very endeared to you if I'd never heard the show before. I feel like I can hear your smile coming through in all of your interviews, which is such a great thing. It's just, I'm, it's magnetic and, you know, it's clear that you have an admiration for Seth Godden. But, but I think, you know, in hearing as many interviews as with him as I have on other shows, I think there's a tendency to sort of like, talk up to people and try and or, or try to puff yourself up and sort of be on the level of someone who has some sort of, of level of fame or that you admire. And I just didn't get that at all. And you know, I, I do from my perspective, consider you and Seth contemporaries, but you have interviewed such luminous names. How do you immediately embark on these exploratory journeys from a place of rapport and warmth instead of what could be, you know, fangirling or like I said, trying to like puff yourself up to be on their level? I, I feel like artifice kills a lot of these interviews with big names and I never got that from you. How do you get there? Speaker 3 00:21:18 Thank you. Well, I, somebody has to tell you that you do that and then you stop doing it <laugh>. So, um, in terms of, you know, Seth, I have a tremendous amount of respect for, but I also have a friendship with, right? And so I feel very, I feel very secure and, and in and trusting with Seth. He's been so generous to me and so kind to me and so good to me. And there was also this genuine appreciation of the book, which I also ask my students now to read because it is such a great foundation and what it means to make things and to make things consistently and why do you make things and how do you make things and how do you get your things out there and why you get them out there. And it's, it's such a powerful book about the art of making and sharing that it's, it's hard not to feel like it's a book that you can fawn over Speaker 1 00:22:20 <laugh>. Sure, sure. Understandably. When so many people are asking him questions publicly in, in all channels, all mediums at that moment in time about that same project, where do you look to sort of tuck into the material or tuck into the interview and, and try to find that avenue or I mentioned before that that little crack of daylight. How do you find that when there's just so much being said about him and his book at that moment? Speaker 3 00:22:42 Well, first of all, I read the book, I can't even begin to tell you how many guests I interview. And they say, you read the book, you read the whole book. I'm like, yeah, <laugh>, not only did I read that book, but I probably read your other book too. Um, and in ca in the case of Seth, I have read every one of his books. Yeah. So just actually doing the work helps doing the actual work. And I did mean what I said. I did have to have Roxanne, my wife get the book as well so that I can, so I didn't have to dilute what I was or, or contain what I was, um, highlighting so that I could export and then ask questions about. I didn't want to do that until the actual edit of my questions. So when I'm, when I'm getting ready for an interview, I will generally have about anywheres between 50 and 70 pages of research. Speaker 3 00:23:35 And that comes from the transcriptions of the other podcasts that I've listened to. And that's a fairly new thing. I didn't always do that. I would mostly gather research from interviews that had been conducted online or transcripts that were readily available. Yeah. And then I found like Tim has his transcripts readily available. Right. I, I, Dak Shepherd does not, uh, fresh Air does. Um, so that, so some do and some don't, but I also like to listen to some indie ones because those are also where you find the gems. And so I'll transcribe generally about five additional podcasts in, in addition to the written interviews or the transcribed interviews already online. Sure. And so I'll have between 50 and 70 pages of research, then I sort of put them in order of a person's life, you know, how much did they go over in terms of the history, how much have I found? And then I create an arc. So that almost as if you were doing this sort of Marvel cinematic universe and watching the movies in real time, you know, in the way that they should have been introduced, not should have been, but just over the course of history Right. And Speaker 1 00:24:44 Time. Right. Right. Speaker 3 00:24:46 And then I call the questions that I wanna ask from that then I usually end up with, after between 50 and 70 pages, say down to 30 I and the editing is the hardest part. What don't I wanna ask is harder than what to what I do wanna ask. Sure. And then end up with anywheres from, I would say seven to 10 pages of questions for an hour to an hour and 15 long interview. Speaker 1 00:25:16 I'm amazed, but also overwhelmed. Thinking about that number of pages and or number of questions or ideas that you could pursue, are you looking for a couple of openers and then pursuing curiosity? Do you have like sections of your interview that broadly speaking you wanna touch on? Like, okay, in general we start here and then we move to this section. How do you go from what, what is whittled down, but still a lot to that final interview? Speaker 3 00:25:41 Yes. I always wanna start with something that will surprise my guest. And that is a kind of bit of formula for me. I wanna do that because I want them to feel comfortable. I want them to laugh. I want them to, in that moment understand how much work I've done to understand who they are and to, to show my respect for who they are in that process of doing that. And so, you know, in over the course of my interview, if somebody doesn't say, where did you find that? I kind of feel like I haven't done a good enough job. Um, I've been, I've been asked if I've spoken to somebody's mother or somebody's spouse or somebody's sister. And that to me is an indication of a good, um, interview. I do not speak to anybody <laugh>, just do all my own research. Um, but I love it when they think that I have, cuz then they, they know how hard I've worked. And I mean, I don't care about them knowing how hard I've worked necessarily, but I do want them to feel respected about the work that they've done in their lives. And that's sort of the way I think I show it. Speaker 1 00:26:49 I I wanna move to the next clip, um, and sort of build on where we, we just landed. So this comes around 15 minutes into your interview with Seth. And uh, we're coming into the middle in this clip of Seth just answering a question that he'd asked you, uh, asked him previously about the title of his new book, the Practice. And then we're gonna hear your reflection about what he just said, followed by your next question. Let's take a listen. Speaker 5 00:27:13 So the practice is simple. The practice says we merely do this work. We make the choice to do the work, and then we do it without commentary, without drama, without reassurance, without needing to be assured of an outcome, we merely do the work. And I know a lot of creative people, not as many as you, but a lot who have become famous, who have won awards, who are successful in every field. And this is what they have in common. It's not a talent, it's not something that the muse touched them and not somebody else. They simply do the work. And there are times that they'll do a hack just to succeed. But most of the time when they're proud of their work, it's because they have a practice. And the practice is its own reward. And its output is a thing that might lead to the thing you're hoping for. But that's not why you do it. You do it because it's your practice. Speaker 4 00:28:15 Well, we're actually gonna take a deep dive into many of the words you just used, hack, trust, uh, reassurance, especially reassurance, um, and so forth. Um, in the book you write that the practice is agnostic about the outcome and the practice remains regardless of the outcome. Can you elaborate a little bit on what you mean by agnostic? Speaker 5 00:28:40 So let me just use an example that might not sound like it's a creative work, which is being a doctor. Speaker 1 00:28:51 Reactions to hearing that piece played back. Speaker 3 00:28:53 That was pretty good, Speaker 1 00:28:55 <laugh>. Why? Speaker 3 00:28:56 Um, because I didn't pontificate <laugh> like I did in the beginning. This was more, um, generous. I just asked a question and let him answer it. Speaker 1 00:29:09 I thought it was generous for the audience as well where you said there's a plan you hinted at, there's a plan, something is coming stick around, right? Yeah. So you're kind of anchoring us to what's upfront, which, you know, it serves your show too because you're saying there's something worth your time. It's a little tease, please don't drop off. But it also serves the listener as it helps them shape the experience that they can expect. So many people who appear publicly, uh, and I think Seth is properly at the pinnacle of this pyramid. Um, they stick the landing on their rants and their answers. They come to a definitive conclusion when they respond to something. They don't really leave the door open for like a follow up question necessarily, or like, what do you think, Debbie? It's very much, it has a, it has an arc and it comes to a final destination. And then it's like, where do I go as an interviewer? And if you like, listen to my early bad interviews, um, I used to say Got it. After literally every answer. Speaker 3 00:30:01 Oh, Speaker 1 00:30:02 <laugh>, oh my goodness. Even if I didn't got it, I was like, got it. Cause I didn't know where else to go. Um, yeah, this, can Speaker 3 00:30:09 I interrupt for a second and tell you please and tell you what I used to do? Oh yeah. And I, and I got, I got caught on this one, um, by Hillman, the late great Hillman Curtis. So Hillman Curtis, uh, was a filmmaker and, and he, um, sadly died when he was 50 about, I would say about 10 years ago. And, and I miss him so much, he and I did seven collaborations together. We, he, uh, filmed and then created these wonderful pieces, uh, that, that we did together of interviews. And at one point I was interviewing, this was in my first or second year of, of doing Design Matters. I was interviewing the legendary conceptual artist, Lawrence Wiener. And we were doing it live in person. And at one point Hillman pulled me over to the side and he said, Debbie, what? You don't have to say mm-hmm <affirmative> after everything Lauren Speaker 1 00:31:03 Says <laugh>. Oh geez, Speaker 3 00:31:05 <laugh>. And then somebody, oh, Curtis, my current producer's like, stop saying the word. So before every question, so Jay <laugh>, Speaker 1 00:31:18 So, so Debbie, I gotta say it's one of the most bizarre transitions between like a chat over coffee with a friend and talking with microphones in your faces where you're so hardwired, at least I am to say something to acknowledge that you just spoke. Whereas like you just moved on, there was such a nice end to that Seth answer and it, it was a continuation. You didn't say, okay, random next question, new line of thinking. It was still building on what he said, but you simply moved on. Or I guess if I was gonna use this Seth word merely moved on you, you went ahead with your plan. And I think to me that's where these pages and pages of notes also show up. It's not just in the little threads you pull that you found in the research, it's also the fact that you have that confidence in where you're gonna head next. Speaker 3 00:32:03 Thank you. Sure. Speaker 1 00:32:06 The missing piece in a lot of interview shows is what they're driving towards. And so I mentioned before they get superficial, they sort of touch on all the popular beats. Um, Seth is someone who comes with a lot of popular beats, he can be very quippy. And how do you get someone to not just stick to those quips, but to try and, you know, with, uh, an, an eye to respecting them and making them feel comfortable. You're not attacking them, but how do you sort of knock them off the predictable quips and get them to improvise and say something original Speaker 3 00:32:39 To remind them that they said the quip and ask about details about the quip. And that's, and that's classic design matters right there. Speaker 1 00:32:48 So you've actually said, I've heard that before, or can you go deeper? Things like Speaker 3 00:32:52 That. I, I would say, um, you've said that, or I understand that you have done this or that. That's a, that's a very typical way of me, um, opening up a question. I can even, I mean I have another computer here, I can open that up and share with you, um, some of the ways that I will start at a question. So let's go sign matters. Let's do, I can actually go to this Seth one if you want and see how I ask of Speaker 1 00:33:25 Those questions. Sounds great. And what specifically are you looking at Speaker 3 00:33:27 My, I am looking for and will be looking at my script. I create a script for every show and it is my script. Um, here we go. And it is a script of my questions and that doesn't mean that I'm asking every single question on my script. And, uh, one thing that I do want to be able to share for your listeners is that I consider every great interview a conversation that is sort of like playing a game of billiards. The goal when you're playing pool is to not only get one billiard ball in one pocket, but to leave the rest of the balls on the table to be able to continue to get additional billiard balls in additional pockets. Huh. And so it's very strategic. You wanna make sure that the balls are in position to continue to be able to shoot and not lose your turn. And so what I try to do is ask questions that allow for any answer to take me in any direction. And because of my research I can pull up a question in relation to the answer. Speaker 1 00:34:35 So you never maybe back against a wall and not sure where, where else to go. In other words, is that, is that fair to say? Speaker 3 00:34:41 Yes, that's exactly right. Ok. That's exactly, exactly right. Got it. Um, so let's see here. So one of the things I say in a recent interview with Tim Ferris <laugh>, you stated that probably for the last five books you felt like you didn't know when the next book after it would be coming. And this is one of those books you go on to state that if this had to be your last book, you'd be proud to make this your last book. So that was like a quick, right, that was something he had said. Then I say, I have two questions about this. First, what gave you the sense after the last five books they could be your last and why if the practice is indeed your last book, would that be okay? And so I'm already taking something that he stated and my guess is that he may have said that beyond just to Tim, cuz that's a pretty profound thing to say. Right? Um, and then, and then elaborate on what it was that he said. Speaker 1 00:35:38 How might your approach change or, or does it, if you interview someone who's not as publicly, uh, prolific as a Seth Goden and their, so their body of work isn't as easily accessible, uh, or are you at the point with the show where the guests you're interested in or, or happen to book, do you have that public persona? In most cases? Speaker 3 00:35:58 I would say that I have the public persona in most places. There are a few people, like I just interviewed Ping Zoo, she's very young. Uh, she is an illustrator really making a big splash in the world. In that case, I was actually worried with her because I, I didn't have as much research to pull from. But then you end up getting the whole angle of, well, how do you, how do you start, how do you make an aim for yourself? How do you begin to create a body of work that has a recognizable style? How do you pace yourself if you are really successful out of the gate? And so that what, what I was worried about never really came to fruition because I was able to talk about the process of starting a career in a way that I might not have been able to with somebody like Seth. Speaker 1 00:36:50 What would you say to podcasters, and I've heard this pushback when I talk about the power of research who say, well, I don't wanna be overly rehearsed. I don't want to like stick to a list. I don't, I don't want to have this kind of like, stiff conversation. I'd like my curiosity to just lead the way. So I'm not gonna do research. Speaker 3 00:37:10 Well, I don't wanna be mean, but then I would say that's very lazy, lazy, lazy, lazy <laugh>. First of all, anybody that says that to me. And I, I do try to go on as many podcasts as people invite me on because I was, people were so generous with me at the beginning that I try to be generous as well. I mean, not like overly crazy to a point where it overtakes my life, but if somebody has a genuine offer that's starting a podcast that I feel is really interesting, I try to pay it forward because so many people did that with me. And for those that do say I don't like to rehearse or I don't like to have scripted questions, chances are they could have found any answer to any question they asked me on Wikipedia. Right. Speaker 3 00:37:53 And, and then I feel like, you know, I don't, I don't wanna criticize anybody specifically, but I just feel like, and I don't do it even in, in the moment, you know, there, there was such an opportunity to have a much richer conversation. Yeah. Um, that, that it feels to me that they're missing an opportunity to go further. Even somebody like Tim Ferris who's interviewed everybody who's, who's the most, one of the most, if not the most famous interviewer on the planet, and certainly one of the most generous open-hearted people alive, he did research on little old me <laugh> and found a question in something that he found that no one had ever asked me before that ultimately changed the way that I talk about my history in such a profound way. He didn't have to do that, he didn't have to do that at all. He's Tim Ferris, and yet he did. And that's probably why he's Tim Ferris. Speaker 1 00:38:47 As someone who's a guest on a lot of shows, uh, how do you feel when you are surprised by a question? I, I, I got a, a very strange interaction, Debbie, that led me to asking you this, which is one such individual who said, I don't wanna do the research. And, and actually by now it's been multiple individuals, but a small number of people have said, well, but these people are really busy. They're promoting a book or they're an executive, or yada yada. And so like, I don't wanna ask them questions that they're not prepared for. I feel like that's doing them a disservice. As someone who just said, Tim asked you something you didn't expect and went deeper, how does that make you feel as a guest in, in reality? Speaker 3 00:39:22 It makes me feel honored. First of all, if you're asking somebody about something that happened in their lives, how could they not be prepared? You're not making something up. You're not asking about trigonometry unless you're talking to a mathematician. You know, let's face it, I'm not gonna ask somebody about the, um, the big, the big bang. Um, if they're not an astrophysicist, you know, <laugh>. And that's the only time I have asked about the Big Bang is with an astrophysicist. Um, so I think that it gives you an opportunity to challenge them in a way that they wanna be challenged and not feel like they just press play and answer the same old questions that everybody asks. I have to say that most of my guests end up thanking me for not asking the same old same old questions because they're bored answering. They're bored with those same questions. Speaker 1 00:40:22 This is, uh, the third and final clip, and it's toward the very end of the episode of your interview with Seth Godin. Um, you'd previously said that you, you told Seth this, and so the listener heard you say this. You have a few last questions and then a request. Uh, and so we're gonna come into this clip after you and Seth had been chatting about, um, you terminating a book deal. Let's take a listen. Speaker 4 00:40:45 Bye-bye. Book deal <laugh>. In any case, I have one last question for you, and then the request, um, although the question is sort of two-parter, you ask in the book of people to consider, when was the last time you did something for the first time? And I'm wondering if you might share that with us. Like, when was the last time you did something for the first time and how did it go? Speaker 5 00:41:15 Often when I ask people this question, they tear up and they tear up because if they're honest with themselves, it's been too long. That feeling of doing something for the first time is so precious and we have built a, a luxurious world where so many of us are not living hand to mouth, uh, with no other options. And yet we waste it because we watched the seventh episode of Emily in Paris instead of figuring out how to explore a frontier. So the, you know, dramatic visual one is I built a canoe in my backyard over the last five months and from scratch using hundreds of sticks. Speaker 4 00:42:00 Wow. Speaker 5 00:42:01 But every day I do something small, engaging with a human in a way that doesn't feel like rote to me. Um, and that for me is the practice of that first time thing of saying, I might not know this person very well, or I might not have been in this situation before. How can I engage with them in a way where they are actually seen? And I had a conversation with a woman this morning that I think helped both of us a lot because I saw the journey that she was on as a creator and I was on thin ice in how I was talking about it. But I was helpful and that was thrilling, I think, for both of us. Cause I don't want to get into the business of doing rote. So when I think of that, and then I think of paddling my canoe on sugar pond, the, the, I'm, I'm trying, I'm trying to do things for the first time, Speaker 4 00:43:00 Seth, I was wondering, this is my request. Speaker 1 00:43:05 What stood out to you about that clip, Debbie? Speaker 3 00:43:09 Well, I didn't like the wow. I didn't need to have said the Wow. Wow. It's like Uhhuh <laugh>. Speaker 1 00:43:17 So Speaker 3 00:43:18 Exactly. <laugh> got it. But that's just from my perspective, from his perspective, he was perfect. Speaker 1 00:43:25 He puts down a lot of surface area. There's like lots of little threads rearing their heads that you could pull on and be like, oh, I can follow up there. Or I could ask some more details there I could. And you just sort of let him go. Um, is that just got instinct? Are you, have you, uh, again, a lot of things you've said today, it's hard. One, it's learned through criticism, through self-reflection. I feel like many podcasters may have tried to follow up and create a moment. You asked a very simple question. You said this in your book, have at it and let him go. How is that in the arc? Is that in the notes? Is that like, this is the final question. Here's the dismount for the episode. It's an amazing thing. I'm just gonna ask it. And back off. How planned was that moment versus felt? Speaker 3 00:44:08 That's a great question. How planned versus felt? Well, it was hoped for <laugh>. One thing I did learn very early on as well, when I asked someone that I had interviewed in that first year who was a friend, as I mentioned, most of those early interviews were with friends. I said, how'd I do? You know, expecting to hear great <laugh>? And she said, well, Debbie, you know, maybe you wanna listen to the answer before you ask the next question. And she's right. A lot of a lot of people talk, talk, talk, talk, talk and wait for somebody else to stop talking when they're not talking, and then start talking again without really listening. So you do really have to listen. And in that moment, and maybe this is where instinct does come in, after doing it for as long as I have, sometimes you just wanna give that a little bit of space, doesn't really need a follow up. If you give it a little bit of space, then you can move on. Doesn't need a oh really, or what? No <laugh>. Um, and then, and then you are able to create that drama in that moment. Speaker 1 00:45:17 You, you said the word drama, which is interesting. A lot of folks might think, oh, a narrative podcast has drama. A true crime crime podcast, documentary series on Netflix has drama. The Marvel cinematic universe creates drama. But an interview, what do you mean by drama in an interview, Speaker 3 00:45:35 Deep feeling that moment to allow the words to resonate, to allow for the possibility of goosebumps. I'm doing it right Speaker 1 00:45:53 Now. I was gonna say thank you for doing that. Our show is better for you, <laugh>, you're welcome back Anytime, Speaker 3 00:45:59 <laugh>, Speaker 1 00:46:02 I'm reminded of your interview with Richard Kesh Hiway, the host of Song Exploder, uh, both the podcast and now the Netflix show, where he said something I I thought very profound, sort of summarizing what many of us might feel kind of lacking the words for where he said that so much art lives between intention and instinct. It's something consciously considered and something felt. And I feel like your show is defined by sort of the, the interplay between those two things. There's so much research and process, so much practice to speak to Seth's book, ideas, so many reps that you've put in. And yet despite all that, you, you clearly are okay and even excited to not over-engineer every little moment. Speaker 3 00:46:47 I agree. I agree. I think that's a really nice way of putting it. And nothing, not a way that I would've thought of putting it. I do think you've deconstructed this in a way that helps me make sense of what I'm doing. Um, I don't really think about the engineering or the deconstruction of these moments quite in this way, but even listening to the clips gives me ideas about how I could improve some of my engagement. I still feel like there are times when I add color that isn't really necessary. Speaker 1 00:47:29 That is a perfect segue to our final segment, which does not have a clip, but it's looking ahead. I mean, you're, we're looking back on a, a large body of work here with the show, 16 years, 500 plus episodes and counting incredible guests and moments. And yet when I say, what'd you think about that one? You're like, oh, didn't love that part. You know, you're like, oh, I need some criticism that it's clear you're still driven to do this show. So when you look ahead, are there things you've thought about, uh, where you'd like to try and experiment with something or reinvent something or improve on something to keep the show fresh moving forward? Speaker 3 00:48:05 It's an interesting time for me in the show, in this sort of arc of my own journey. I have a book coming out in October called Why Design Matters, conversations with the World's Most Creative People. And it's really given me an opportunity to analyze what I've done over the past 16 years. In many ways though, it's a book containing interviews and excerpts with, I don't know, over a hundred people that I've spoken to. It's in many ways a monograph, um, because it's the, the, the common denominator is my asking the questions. And so I've, I've been able to analyze my growth, my flaws, my nephews. Um, I think that I would like to keep growing as an interviewer. I'd like to keep growing as a person with curiosity and continue to ask questions that help to define and express who people really are. And in a way that not only gives the people that are doing the talking and opportunity to share with generosity and insight and clarity, but also to give people that are listening the opportunity to consider what their possibilities are. So much of what underlines I think every episode of Design Matters is how to overcome those obstacles. How to create a place of awareness to make things better for themselves, for the world, whatever I'm really talking about making things with their hands or with their mind. And if, if I can help people do that, then I feel like the work is worth it. Speaker 1 00:50:06 Debbie Millman, uh, the, the show is Design Matters. The upcoming book is Why Design Matters. Thank you so much for coming on our show and teaching and inspiring some podcasters. Send swag to their guests as a way of saying thank you. Some people send little handwritten notes. We think we should cut down on the emissions and if we're being honest, the eventual trash. And so as a way of saying thank you, we're gonna place a small donation to the Joyful Heart Foundation, which I know you're a part of and and involved with as a way of saying thank you so much, not only for coming on our show, but for all the great creative work that you're doing to inspire even more creative work in the world. So Debbie Millman, thank you so much. Speaker 3 00:50:41 Thank you, Jay. Thank you so, so much. Speaker 1 00:50:49 Thanks for listening. This episode was produced by Cherie Turner with original theme music from Cardboard Rocket Ship. You can learn more about Debbie millman@debbiemillman.com and more about me and my projects for podcasters and creative people. At j icono.com three clips is a Casto original series. I love making this show with Casto. They're a software provider for podcasters. We believe the same things about creativity and podcasting. And specifically, they're now investing in the idea that podcasting is all about going deeper with the ideas you explore and with the relationships you build with your audience. As a result, they're offering tools for podcasters to help makers and marketers specifically reach their communities and their teammates through private podcasts. So whether you wanna offer something extra special, like bonus content, something internal only to your organization, or something that drives revenue for your creator business, perhaps consider a private podcast and do what this medium does best. Connect more deeply. Learn more@casto.com, cas t os.com. And now our bonus segment where every episode we ask our guests for a podcast they'd recommend that is not at the top of the charts. It's not a show we've all heard of for years and years. It's a show they'd like to show some love to. We call this segment, play It Forward. Speaker 3 00:52:14 The show is called the Lisa Conden Sessions, and Lisa is an extraordinary artist living in the Pacific Northwest. She has a practice, uh, as an illustrator and artist, and is always making things. One of the really remarkable things about Lisa, and this is Lisa's life beyond the podcast, but also in the podcast, is she's very clear about why she makes things, how she makes things, and why you could do it too, <laugh>. And so a lot of her work is they're, there's sort of two different parts of her work, two different bodies. One is the making things and the other is explaining how she makes things and how you can make them too. And this podcast is the perfect Venn diagram of, of those practices. Uh, so it's the Lisa Conden Sessions by Lisa Conden. And, um, it's brand new. I think she's maybe done one season or not even finished with her first season, but it's, it's hit the airwaves like gangbusters and, and I really admire what she's doing and how she's doing it. Speaker 1 00:53:31 All right, that's it for this episode. As always, I'm your host, Jay Hanzo, and as always, I believe great podcasting, great creative work is not about who arrives, it's about who stays. So thank you so much for staying with me, and I'll talk to you every Monday with a brand new episode of Three Clips. See ya.

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