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Episode 301: Debbie Millman
205 Plays3 years ago
Debbie Millman (@debbiemillman) is the host of the incredible Design Matters podcast and the author of Why Design Matters: Conversations with the World's Most Creative People (Porchlight Books, 2022).
Social: @CNFPod
Support: patreon.com/cnfpod
Sponsor: West Virginia Wesleyan College's MFA in Creative Writing
Show notes/Newsletter: brendanomeara.com
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Transcript
Introduction and Gratitude to Patrons
00:00:01
Speaker
Hey C&Fers, you know, I can't do this all the time. Doesn't make sense, but I do want to take the time right now, do this right now. I'm going to thank all of the current 16 patrons for their amazing support of the show and their enduring patience with me as I struggle to get every available transcript to them as timely as possible.
00:00:26
Speaker
If I mess up some pronunciations, I'm sorry, but here we go. I just want to thank...
Writing Support and Guest Introduction
00:00:51
Speaker
Oh, I like that. Oh, also, it's that time of year. Is it, though, still maybe on that treadmill? How's that peloton working? You might even be hiring a personal trainer. Who knows? But maybe you're writing. This is the point. Maybe you're writing needs a boost. That little something, something in your corner. And if you're working on a book, an essay, a query, book proposal, and I know something about proposals right now, let me tell you,
00:01:20
Speaker
If you're ready to level up, email me, Brendan at BrendanOmera.com, and we'll start a dialogue. I'd be honored to help you get where you want to go. That's a really great question, Brendan, and no one has ever asked me that. Well, all right. This is the Creative Nonfiction podcast, a show where I speak to badass people about the art and craft of telling true stories. I'm Brendan Omera. How's it going?
00:01:49
Speaker
Can you believe Debbie Millman came back to the show? Amazing. That name should mean something to you and if it doesn't, well, buckle up. Debbie's been the host and producer of Design Matters since before Twitter hatched from its egg. Seriously.
00:02:05
Speaker
She's interviewed people like Elizabeth Gilbert, Milton Glaser, Tim Ferriss, Seth Godin, her wife Roxanne Gaye, Paula Shear, and millions of others, slight hyperbole, but you kinda get the drift. To me, in terms of interviewers, it's Joe Donahue of WAMC Public Radio in Albany, New York, and Twist of Fate, as it were. Debbie Nelman went to SUNY Albany, and she, and she is the other interviewer
00:02:34
Speaker
that are emblazoned the top Mount Podmore. Debbie was on the show a few years ago, episode 131, and I was puke up my breakfast nervous. I was better this time around, I think. And that's a great thing because she has a new book out called, Why Design Matters Conversations with the World's Most Creative People.
Debbie Millman's New Book and Podcast History
00:02:58
Speaker
Maybe for my next book, I'll be able to lobby to get on Design Matters, but hey, we can dream.
00:03:06
Speaker
This book is something special, it's beautiful, and it encompasses the arc of her podcast since its beginning, its inception in 2005 to the current day.
00:03:18
Speaker
conversations with luminaries and design, music, tech, writing, art. It's a beautiful book by a beautiful person who does beautiful, unmistakably Millman-esque work. But before that, let's do some housekeeping CNF-ers. I want to remind you to keep the conversation going on Twitter, at cnfpodair and at Creative Nonfiction Podcasts on Instagram.
00:03:43
Speaker
You can also support the podcast by becoming a paid member at patreon.com slash, cnfbot slash. As I say, the show is free, but it sure as hell ain't cheap. Members get transcripts, chances to ask questions of future guests, special podcasts, and hell, I might even thank you at the top of the show. It's been known to happen. Free ways to support the show, of course, are you may be leaving a kind review on Apple Podcasts or leaving a rating on Spotify.
00:04:09
Speaker
written reviews for our little podcast that could go a long way toward validating this enterprise for the wayward CNF-er. We've stalled out a bit of late, but it would be nice to ramp this up again, like this one from Nelson underscore AJ, titled A Must Listen for Nonfiction Writers.
Engagement and Listener Impact
00:04:28
Speaker
Every week, Brendan conducts a penetrating interview with a skilled and experienced nonfiction writer. Rare is the week I don't learn something I can apply to my own writing. This podcast has changed my life. Well, and I speak without hyperbole that that review changed my life. Show notes and my up to 11 newsletter can be found at brendanomare.com. Once a month, no spam. As far as I can tell, you can't beat it.
00:05:00
Speaker
Well, in support for the Creative Non-Fiction podcast brought to you by West Virginia Wesleyan's Aloe Residency MFA in Creative Writing. Now in its 11th year, this affordable program boasts a low student-to-faculty ratio and a strong sense of community. Recent CNF faculty include Brandon Milling's Noble, Jeremy Jones, and CNF
Promotion and Debbie's Influence
00:05:17
Speaker
pot alum Sarah Einstein. There's also fiction and poetry tracks. Recent faculty including Ashley Bryan Phillips, Jacinda Townsend, as well as Diane Gilliam and Savannah Sipple.
00:05:28
Speaker
So no matter your discipline, man, if you're looking to up your craft or maybe learn a new one, consider West Virginia Wesleyan right in the heart of Appalachia. Visit nfa.wvwc.edu for more information and dates of enrollment. Now, as we start to ramp up this show with Debbie, you can go follow her on Twitter at Debbie Millman, two L's. Her website is DebbieMillman.com. Also on Instagram, DebbieMillman at DebbieMillman.
00:05:57
Speaker
She's a designer and a branding guru. I think at one point there was something like 25% of all products on a grocery store had Debbie's fingerprints on them. Not literally man, not literally Donna. This conversation took place back in October.
00:06:15
Speaker
when her book was supposed to come out. But because of supply chain stuff and things that are above my intellect, the book kept getting punted and punted until February 22, like the 22nd of the 2022 calendar year. So here we are.
00:06:34
Speaker
She's a big, big fish swimming in our tiny CNF and pod. And it brings me so much pleasure to deliver the one and the only Debbie Milman to you.
Podcast Evolution and Personal Branding
00:06:57
Speaker
You know, anytime you start a creative endeavor of some kind, he's big on asking, who's it for and what's it for? And I wonder with, you know, maybe even when you started the podcast and as the podcast evolved, how have you answered that question of what design matters is like, who's it for and what's it for?
00:07:20
Speaker
That's a really good question. You know, I started this show 16 and a half years ago and I wasn't intending for this to be as big a part of my life as it turned out to be. I thought it would be a fun little project to get my creative juices sort of spinning again. I had been feeling really creatively depleted and really wanted to
00:07:49
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ignite a new way of considering working at that point. And it was very much at the time a inside baseball kind of podcast. Designers talking about design, very insular. Over the years it's evolved
00:08:09
Speaker
to a show about how the world's most creative people create the arc of their lives. And so I've tried to re-engineer the name a little bit to reflect the notion of how the world's most incredibly creative people design the arc of their lives. So that the name still matters to a degree, you know, as
00:08:35
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in my previous life as a brand consultant and in my current life as a brand educator, I would hesitate to tell anyone to sort of walk away from the amount of equity the name currently has. And so I had to follow my own advice in that regard.
00:08:56
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Yeah, and baked into that in terms of the creativity and the agency that it takes to cultivate a creative life is that degree of agency and that it is something that everyone you have in this show manifests through their effort and through their vision and through their singular devotion to the thing.
00:09:18
Speaker
What degree of agency should people take away from that knowing that it is within most people's grasp if you can just kind of sit down and focus on the thing that means the most to you? I'm endlessly fascinated by the way people
00:09:36
Speaker
become who they are? How do they overcome their obstacles? How did they confront their fears? How did they push through self loathing or lack of confidence or personal setbacks to really
00:09:54
Speaker
become the person that they wanted to be. That for me is just incredibly revealing in terms of helping to define humanity.
00:10:07
Speaker
Have you ever run across this, and maybe you've run across it personally, is that you have a vision in your head of what you think you want or where you think you want to be, and then on the course of that journey, you might realize halfway through like, oh my God, I actually don't want to go this way, and it's time to pivot, and yet there's this anchor of sunk cost on my ankle. Have you ever run across that with your guests or even with yourself?
00:10:36
Speaker
Um, absolutely. I mean, I'm constantly changing my mind about things, which is sort of why I resist the idea of personal branding because we are always recreating ourselves and becoming and evolving in ways we might not anticipate. And so if we were to adhere to the sort of strict sense of branding that
00:11:03
Speaker
about face that pivot is sort of in a lot of ways look down upon because people really like consistency in their branding. They hate change, but people change all the time and they should be changing all the time.
00:11:19
Speaker
in order to grow and develop. So that's a lot of the reason why I have issues with the whole notion of personal branding. People should be developing their character, their reputation, not so much the manufactured brand that doesn't really have a living, breathing soul in the way that humans do.
00:11:44
Speaker
And can you point to a particular moment where you felt the podcast itself, it started to glom on to the culture and kind of take off in a way that maybe you didn't see coming as it was starting out very early on, as you said, is very inside baseball.
00:12:01
Speaker
Well, there were a couple of different moments along the way. I would say the first big moment was when I made the move to Design Observer from Voice America. Voice America is where I started the show. They reached out to me in 2004 about hosting a radio show.
00:12:19
Speaker
And I was, as I said at the time, really feeling like my creative soul was dying and wanted to try anything to recapture it, to revive it. And so I signed on. At the time I thought they were offering me a job. What they were really offering me was an opportunity to pay them to produce this radio show.
00:12:42
Speaker
But again, because I was so desperate and I was making good money in branding, thought, you know, I'm going to try this. So I did 100 episodes on Voice America, and I was approached by Bill Drentel, the late, great founder of Design Observer, one of the original design blogs. And he invited me to bring the show over to Design Observer, no money exchange, but
00:13:09
Speaker
certainly a very critical audience in the design community. But he gave me a caveat. I had to improve the sound quality, which was really dismal for those first hundred episodes. I didn't really know how to do that. I've always been a technophobe. And so he introduced me to Curtis Fox, who was at the time doing the podcast for The New Yorker. And so I have been working with Curtis ever since.
00:13:39
Speaker
and he's the executive producer on the show. So moving to Design Observer was certainly the first big change. In 2011, the show was nominated for the Cooper Hewitt National Design Award. It was nominated
00:13:58
Speaker
by the people. It was for the People's Choice Award. And that competition was really stiff. I was up against the High Line and a couple of other really major entities in New York. And I won. The show won. So in 2011, I was awarded and went to the White House and met the first lady, Michelle Obama. And that was really a spectacular moment.
00:14:26
Speaker
and then I would guess the next significant
00:14:29
Speaker
moment for the show was in 2015 when iTunes went to Apple Podcasts and named the show one of the best shows on Apple Podcasts. So that was major, because that was with like Marc Maron and Radiolab and a lot of the big, big, big podcasts. So that was another major moment in 2015.
00:14:56
Speaker
And then I would say in the last two years, I've moved over to the TED Audio Collective. Again, no money exchange, but they are helping me grow the show. And they are actually, there is some money exchange in that they helped me with advertising. And so they've helped me grow the show both in audience and in revenue. And then very, very recently, like I think two months ago, Apple Podcast,
00:15:24
Speaker
designated the show one of their all time favorites. So that's pretty amazing too. So those are some sort of key moments in the development of the show.
00:15:35
Speaker
Yeah, and I think as any great athlete would tell you, and I love when you talk in sport metaphor, it pops through every now and again. I love it, because that really speaks to the way my brain works in terms of rejection and failure and pushing through all that stuff. It's so tethered to sport. You can get to the top. You got that on the Apple podcast thing as a thing, and it's amazing and gets you that visibility.
00:16:03
Speaker
And you might have been able to, let's say, anyone who might have that visibility at that moment might be able to stay there for, I don't know, a week or two. But it's a matter of sustaining that greatness. So in
Social Media Challenges and Creative Failures
00:16:15
Speaker
what ways have you been able to really sustain what it is you do so you stay at that level that we've come to know when Design Matters hits our feet on Mondays?
00:16:30
Speaker
Um, I don't know that it's something that I'm specifically conscious of. I mean, I know that there are certain things that I do well, and I know that there are certain things that I don't do well and really need to do better. When it comes to research, I think that that's when I'm really on my game. That's also something I love doing. So I do it a lot. I love spending time researching my guests and
00:16:53
Speaker
reading everything that they've written, if possible, and watching their videos and listening to their talks. I mean, that part for me is the real joy. That's when time disappears. You know, I can just go into a wormhole and come out four or five hours later not realizing that that much time has passed as I learn about who I'm interviewing.
00:17:15
Speaker
not really great at self-promotion. I've had to hire somebody to help me on Twitter because otherwise I would never tweet about the show and just feel kind of icky about doing it even though I know it's so important. There were weeks that go by where I don't put up the show on Instagram and I'm like,
00:17:33
Speaker
Oh, I have to get this up there. But I'm trying really hard to get better at that. Do you find that that matters? I'm trying to consider like trying to determine if that stuff matters. I don't know if it does. Yeah, I really do. I really do. I think if you do it well, I think if you do it well, yes, it does. Oh, yeah. Well, yeah. Certainly. You know, you said you were getting better on trying to get better at promoting on Instagram. I just.
00:18:00
Speaker
Yeah, keep going with that. I'm just curious. I struggle with social media so much like you with the promotion of the thing, and I almost think like, oh, if the show's good enough, it'll spread among the people who want to talk about it. But that's not necessarily the case, because who knows? Someone might be stumbling across the right hashtag at the right time, and it hits them at that moment, and there you go. And it matters to that one person. So yeah, I struggle with that too, Debbie.
00:18:25
Speaker
It's so hard to say. In addition to having all the issues that I do with the whole notion of personal branding, the whole notion of influencer marketing and the projection that people put up on Facebook or Instagram
00:18:45
Speaker
to appear a certain way to their audience is something I also really struggle with. Years and years ago, I was telling someone, it was about five or six years ago, six years ago, after my dad passed away. He passed away suddenly, unexpectedly.
00:19:01
Speaker
I was also dumped that year and I was moving and my role at work was changing. I was feeling really wobbly. And then I went into a depression after my dad died and was dumped. And I remember seeing somebody in the street and I'm like, so how are you? And I'm like, oh, not really that well. And she's like, oh, you seem fine on Facebook. I'm like, everybody seems fine on Facebook.
00:19:28
Speaker
And I really, really try to avoid that prescriptive, self-helpy, influence-y sounding kind of posts at all times because I find it nauseating.
00:19:46
Speaker
Oh yeah, 100%. That's so well put. In the book, and of course, hearing conversation with you, you frequently bring up Milton Glaser, and I recently re-listened to your interview with Seth Godin. Again, the re-release this past week, and it's an interview. I think I've listened to it three times. It's just so good. You two going back and forth. It's wonderful.
00:20:13
Speaker
Oh, he's the best. He's the best. And, you know, you got to talking about piggyback on the Milton Glaser thing is just that you see the home runs, but you don't see the foul balls. And, you know, he just, he had the endurance and perseverance to foul off a lot of balls that maybe a lot of people don't. And I think a lot of people, and using the baseball metaphor, when they put up a batting average on the scoreboard, you know, we see hitting 300, but what we're actually seeing is a 70% failure rate. And that's an all-star.
00:20:42
Speaker
Oh, yeah. I mean, Michael Jordan, I think, had 35% shots, man. 65% of the time, they didn't go in. I mean, between Babe Ruth, Michael Jordan, these guys have, you know, incredible, incredible histories as legends, the greatest of all time. And the fact of the matter is they failed more than they succeeded on a per
00:21:08
Speaker
hit base basis yeah and that's the thing we because we see those percentages and we've accepted them as normal and we know what is good and what is great among that it's like okay we can measure ourselves against something that is objectively good or great but with creative stuff
00:21:25
Speaker
Oftentimes all we are seeing are those home runs and we don't see the foul balls the strikeouts the missed free throws and so it's it's so So what you were saying just underscored so well that it would help so much if we could see everyone's batting average So it wouldn't we wouldn't feel so lousy when we see the great thing on Instagram
00:21:45
Speaker
Right, absolutely. That's part of the reason I keep my old episodes up because anybody can listen to them and say, oh, yeah, she's grown. She's evolved, thankfully.
00:22:00
Speaker
And when you were putting together this book and you've had hundreds and hundreds of interviews, so how did you go about curating the guests that were going to appear in the book and then further curating and editing those interviews in such a way where you distilled it to only a few pages per guest in the book?
00:22:23
Speaker
That was hard, Brendan. That was hard. That was really hard. I can't imagine, yeah. I interviewed over 450 people at this point, probably closer to 500. And the book was a finite size. It couldn't just be however long I wanted it to be. Each interview
00:22:45
Speaker
especially the interviews in the last five years run close to an hour, which is between 7,000 and 10,000 words. That meant that if I was going to deliver a book with 70,000 words, that's seven interviews if I don't edit and condense.
00:23:04
Speaker
So I knew I needed to do that. The book actually, as it turns out, is 150,000 words. Even still, if I had kept all of the original intact interviews as is, that would be 15. Plus there are lots of essays in the book as well. So I knew that I had to do a lot of condensing. I transcribed
00:23:24
Speaker
probably 200 plus interviews, interviews that I knew I liked with people that I felt were able to convey more than just a promotion of their most recent project and things that what I consider to be evergreen. So they weren't specific around something that was happening at that moment in time, certainly politically. So I had about
00:23:52
Speaker
of those 200, I would say probably 125 or so made that first edit, that cut of, okay, these are really universal themes, evergreen time period, and really interesting conversation. That was also certainly a big, big part of it.
00:24:15
Speaker
And then I knew that I needed to be able to have interviews that could be condensed. And so if they weren't able to be condensed for whatever reason, then I knew that they couldn't be included either.
00:24:30
Speaker
And so I did another round of editing and probably that didn't really eliminate too many. I would say that probably got me to about a hundred. And then it was just now a level of entertainment and education. How inspiring could this be for people listening? Would they be interested in what the person said? Would they be provocative? Those kinds of questions.
00:24:56
Speaker
And then there was another layer, and that was, would they agree to be in the book? And if so, would they be willing to give me permission to use photography that they had been in? So I also had to go directly to the photographers to get not only permission, but also to pay them for the use of the photograph.
00:25:22
Speaker
So those were additional levels that I had to go through because not everybody said yes to being in the book. A couple of people said that they were working on their own books and didn't want this to dilute any efforts that they were going to have with some of the content. And that made sense. And then there were others that
00:25:41
Speaker
I couldn't get a photograph that I felt was really indicative of who they were in their soul because initially pre-COVID I was going to do a photo shoot and go around the country and photograph the people that I invited to be in the book.
00:25:59
Speaker
Instead, I had to rely on what had already been photographed and out there, but not so out there that it would feel dull and musky. And I also felt that there needed to be a common denominator in all the photography where you could see the essence of the person in their eyes.
00:26:19
Speaker
And so though there are so many different photographers, I felt that the candid sort of portraiture needed to have a commonality. And I really, really am proud of that aspect of the book because I did all of that myself. I did all the photo editing.
00:26:39
Speaker
and reached out. I worked with an incredible, incredible permissions person who helped me secure all the permissions for the book. Rifka Jenison, really just phenomenal person, then was able to make the book happen.
Interview Process and Photography
00:26:55
Speaker
Yeah, the photography I found striking, and especially, I love those portraits where, just to bring up, say, a Milton Glaser again, where it's right up in his face, you can just see the cracks in his face, and you just, you see, in a sense, in one portrait, you see a life well lived.
00:27:14
Speaker
Yeah, Albert Watson as well. I think both of their photographs have that, you know, super close up. But even the ones in Arendt, you know, Tim Ferriss is a little bit further back and Brené Brown, Seth Godin. I think that they're not quite as in the face, so to speak. But I also feel that, you know, you see their soul in that photograph.
00:27:38
Speaker
Yeah, oh, it's wonderful, yeah. And it does elevate, it elevates the book. And that was something I wanted to ask you too is just, what was the challenge for you in elevating the book so it didn't feel like just a glorified transcript? And you're getting at it with the photography, but I think there's the packaging of it. How important was the design to elevate this book to make it not just podcast transcripts? Right, right.
00:28:07
Speaker
That was also part of the edit to make it feel a little bit more spontaneous, but yet not old.
00:28:17
Speaker
Yeah, with the photography and everything, it is vibrant. I had the digital PDF, so I didn't have it in hand, but I imagine I can picture the weight of the page is going to feel really nice in the hand, because I imagine you spared no expense in making sure that when you hold that page, it feels almost like a photograph unto itself.
00:28:47
Speaker
Yeah, I mean, the book is really hefty. I just got my first bookies and it's 10 by 10 and it's really thick. It's almost 400 pages. So, yeah, it really feels like a tome.
00:29:01
Speaker
I love, and you write in the book, too, that you say, in my best interviews, I'm asking my guests questions only they can answer. I'm not at all interested in asking open-ended cookie-cutter questions about creative process or what they are inspired by or their favorite books. There's nothing wrong with these questions, but I want to give my listeners a unique experience. In that, how would you characterize the listener experience when they're plugging into Design Matters and Debbie Millman?
00:29:31
Speaker
they're not gonna get a lazy interview. I think I was being nice when I wrote that because I don't think they're good questions. I think they're terrible questions and I should have said that. I think they're lazy. I think they're lazy questions because you can find those answers online already to all of those questions if the person has done three interviews in their life. Because it's a question that people seem to come back to more for their own
00:30:00
Speaker
edification or their own inspiration than that of the listener or the reader who as I said could easily find those questions. The other part of this is that
00:30:13
Speaker
I think process is really overrated. I don't understand how learning about somebody else's process is going to make you a better person or a better designer, a better photographer, a better musician. It's just going to teach you about how that person does what they do. And yes, that certainly can be interesting.
00:30:33
Speaker
But I have no interest in asking about it because I feel that it's so prescriptive to be almost useless. I'm much more interested if I am going to ask a question that's been asked before.
00:30:49
Speaker
The question is really more about something that they've already said as opposed to asking them to repeat something that they've already said. So if they've already declared themselves to be XYZ type of person, then I'll say, I understand that you're an XYZ type of person. Can you tell me why?
00:31:11
Speaker
or how did you evolve to that place? So for example, if somebody were reading this transcript of this interview, I've now said on the record, I think this question is lazy, I would expect a good interviewer to say, I understand that you think prescriptive questions in an interview are lazy, why? Or challenge me if they don't agree. Then that becomes an interesting conversation.
00:31:38
Speaker
I go back and forth on that, but mainly I have come to the place where I agree with you that it is lazy, though I have benefited from hearing interviews of things where I was like, oh, I could kind of pluck that and apply it to my own work. But by and large,
00:31:56
Speaker
I've really, I've locked into what Henry Rollins said. I have this great quote from him that kind of echoes the sentiment. He said, it's important if you're a creative person or aspire to be that you don't spend too much time aspiring or asking advice. Just get going and address what's roaring inside you.
00:32:15
Speaker
Oh, I love that. It's stunning. How great is that? And I just feel like when we try to listen to another prescriptive thing and try to get the key to unlock a certain door, we're robbing ourselves of a certain discovery and journey. And I think the best way to do it is to just flop your way through it. And you'll find it'll be a more rewarding journey. And eventually you'll get there with enough rigor and perseverance. But searching for another answer or the magic pill is not going to get you there.
00:32:44
Speaker
I agree. Absolutely. Yeah. And so with your interviews, you're taking us on a much more, I don't know, it's sort of an inspiration philosophical journey. And was that something you walked into pretty early on that that was going to be a definitive experience that you were going to take a listener on with a listener in mind? Not really. Initially, the first 100 or so episodes, no, I would say even more than that. I would say the first
00:33:14
Speaker
200 episodes. I had people providing me with research to help the process. People at Sterling helped me when I was working there. And
00:33:28
Speaker
in some ways that made it easier for me, but it also in some ways limited what was possible in questioning because I was relying on the helper's view of the world in what they had assembled for me to review. And then when I ended up doing it myself, I ended up realizing
00:33:53
Speaker
how much I hadn't been privy to by the sheer virtue of not starting that broad edit on my own.
00:34:03
Speaker
And once I started doing that, I think that the interviews became more intimate.
Interviewing Techniques and Career Insights
00:34:08
Speaker
And that's when I started to really work to develop a narrative arc that really began from a person's early origin story to and through the struggles to become who they are now and the steps along the way to make that happen.
00:34:32
Speaker
Yeah, in tracking the arc of a career, as your show does so wonderfully, there are those moments where there can be some back and forth, and sometimes where you do push back or challenge. And as someone, you know, I do this, just interviewing. I'm very bad at pushing back.
00:34:54
Speaker
I wonder how you maybe got comfortable, if you got comfortable at all, at maybe challenging your guests, maybe when they're not as forthcoming, or if you feel like they're being more restrained, or if they're just being restrained, and you can see there's something there. Well, generally speaking, when I feel that, I'll say something like, really? That's my deep challenge question.
00:35:23
Speaker
And then they generally laugh, and sometimes they'll say yes, and sometimes they'll say no. The most cantankerous interview that I've ever had was with Richard Saul Werman, where I did ultimately have to push back.
00:35:39
Speaker
But sort of did so by throwing up my hands and saying, okay, I guess this is done. And then when he asked for a do-over, I pushed back and said, okay, well, now we're going to do it the way I conducted interview. He got really upset with me for asking questions about his past.
00:35:57
Speaker
when he was much more interested in talking about his future. But I do have a narrative arc that I like to follow, not because it's a cookie cutter approach, but because I'm just really interested in unfurling a person's existence in a specific way so that my own curiosity is engaged. I'm not just interested in talking about
00:36:24
Speaker
success and I'm not just interested in talking about accomplishment and I'm not interested in talking about As you as we've been saying, you know what book they've read or want to read so he got really angry with me for talking about some of the times in his life he struggled because he didn't think it was valuable to my audience to hear this and
00:36:49
Speaker
And I did have to push back and say, well, that is the style. That's the way I conduct interviews. I'm interested in the full picture, not just the highlights.
00:37:00
Speaker
And ultimately, I think I just pissed him off more and more. For you as someone who's done so many interviews, and then you go up, wrong terminology, but let's just say you go up against someone else who is also an incredibly great interviewer. I'm thinking like Ira Glass and people of that ilk. They know the game, they kind of know what you're getting at, and so they kind of
00:37:27
Speaker
They can see the matrix of an interview. So what is the challenge for you when you step onto a stage, a physical stage in that instance where you're interviewing someone like Ira who knows the game? What becomes the challenge for you interviewing skilled interviewers?
00:37:44
Speaker
I was brutally nervous. I was scared that he'd think I was not very good. But it also made me work really hard to find information about him that would surprise him. And I do think that finding out about the skill he had in blowing up balloon animals did that.
00:38:11
Speaker
especially since the balloons I brought to have him make a balloon animal on stage with the wrong balloons, and he had the right balloons with him. I thought that was amazing. I'm like, he actually has these with him. Like, this is amazing. He had them with him, and I just got really, that was, it was, you know, luck and opportunity converge. You know, I had done my homework.
00:38:38
Speaker
I thought I, you know, I didn't know enough about balloon animal balloon blowing to know that you need a certain kind of balloon. Just went and got balloons. And when I brought them out, he was like, those aren't the right balloons and then brought out the right balloon, which made it even more engaging than if it was the right balloon. But I had no way of knowing that, you know, it could have bombed if he was like, those aren't the right balloons and didn't have a balloon.
00:39:08
Speaker
the fact that I asked him about it, asked him to make a balloon animal with the wrong kind of balloon and then pulled out the right kind of balloon.
00:39:16
Speaker
I mean, I couldn't have paid for that to have happened any better. Yeah. I always like digging into someone, you know, I produce this and do this thing myself, and I'm not a huge heavy hand in the edit, but I always clean things up and whatever, and occasionally move things around. And there was one, in listening to your show, there was one editorial choice that I've been wanting to ask you for a long time, and it was when you had Liz Gilbert on.
00:39:46
Speaker
And you had agreed for 45 minutes, and then on Mike, she cut it to 30. She thought it was 30, and she opted for 30. And then you pivot, and it was just like, okay. Sometimes you put in a teaser quote from the show, but in this case, you put in that little exchange that was mildly tense, where she cuts it from 45 to 30 minutes. And I was curious as to the editorial choice of doing that for that particular episode.
00:40:15
Speaker
That's a really great question, Brendan, and no one has ever asked me that. First of all, I had only corresponded with her people. There was no correspondence with her directly prior to the episode. And I had been told by the PR people that I had 40 minutes.
00:40:38
Speaker
And I shouldn't have asked. I should have just done my interview in the way that I had planned to do the interview because it's extremely hard to do the arc of a person's life and do justice to the book that I've just read that they're promoting.
00:40:59
Speaker
in 40 minutes. And so I really, really worked hard to create a satisfying narrative in that timeframe. And then it was dumb of me to ask. I would not have had the idea to put that bit upfront. My producer did because he felt that if I didn't do that,
00:41:23
Speaker
that people would come away from the interview thinking, what's up with Debbie's interview with Elizabeth Gilbert? It's so thin. And so that was the decision.
00:41:33
Speaker
you bring up and you feature Paula Cher a lot. And there was this wonderful notion that she brings up that you cite in the book of a career with deep treads. And I loved that notion. When you hear something like that, when you hear it and then when you read it again, what does it mean to have a career with deep treads? Paula, she is my hero. She is my role model. I think it's about
00:42:02
Speaker
having an understanding of pacing in your career and a stick-to-it-iveness, a grounding. And I think the best way to describe that would be to actually use an anecdote from a different show
00:42:24
Speaker
because I think it illustrates Paula's point in a way that I really try to mimic in some ways. And that was when the interview David Lee Roth, that interview did not make it into the book, not because it wasn't a good interview, but just because there was not a particularly good narrative arc. He was all over the place.
00:42:44
Speaker
It was so hard to keep up with him. His mind worked so fast. And so there were gems, absolute gems, but not a linear arc that made sense.
00:42:58
Speaker
But I have read a lot of feedback that people have had about that particular show on Van Halen boards and whatnot. And people do think it was a good interview. And that made me really happy because he was so far out my wheelhouse. I didn't even know if I could keep up with him. But he did say something that is probably the most brilliant thing. In many ways, it's probably in the top five
00:43:25
Speaker
most brilliant remarks I've heard in any show I've conducted. And that was the notion of the arc of a career. And I had to ask him, you know, what did it feel like in 1984? When 1984 came out, Van Halen was the most popular band on the planet. They were pretty much running full time on MTV. They were tearing up the airwaves.
00:43:48
Speaker
They had it all, sex, drugs, rock and roll, money, everything. And I asked him what that felt like. What did it feel like to be the most popular dude on the planet in 1984? And he said, you have to be really careful when you get to the very top of the highest mountain. He said, you have to be careful because you're usually alone. It's always cold.
00:44:17
Speaker
And there's only one direction to go. And that gave me chills because I've always been in a race to achieve, in a race to make something, in a race to be successful. And I realized that all of my struggles
00:44:35
Speaker
over my 20s, my 30s, those decades of what I call experiments in failure and rejection. I can look back on now with a certain amount of gratitude because ultimately it means that it's taken me longer to peak and somebody like Paula
00:44:53
Speaker
has yet to peak. She is still doing some of the greatest work of her life and just gets better and better and better. And so between my conversation with Paula, my conversation with David, I can say that I really hope that I don't peak until the day before I die. I hate to think that my best work was behind me. And so I think having deep treads means going further up the mountain,
00:45:21
Speaker
where the air might be thinner, and you might need to hold on more closely to ensure that gravity doesn't get you, and you keep chugging along. In the conversation you have with Erin McEwen, who at Sidebar, in 2004, she was playing at the Iron Horse in Northampton, Massachusetts, and I was in my last year at UMass Amherst, and I was a photography intern for the Daily Hamp Gazette.
00:45:50
Speaker
and the paper was writing a feature on her, and I was the photographer, so I shot her, you know, just everywhere for her show and her rehearsals and everything, so it was just really wonderful to see, to track her career since then, and when she popped on your show, I was just like so tickled that she was on the show, and then on top of that, to be featured in the book, she's just such a brilliant mind, and what a voice. Oh my God, she's...
00:46:19
Speaker
one of the most versatile storytellers, musicians, performers I've ever met. Yeah. Yeah. And she wrote and you cited that songs are not precious. And if you come at songwriting from that perspective, you're going to be fine that they're not precious. You've written songs before, you'll write songs in the future, and you'll write many of them. And I love that sentiment, right? It's just keep plugging, keep doing it. And what Seth might say, show me the bad work and the good work will have no choice but to get out.
00:46:49
Speaker
Right. Yeah. Absolutely. When you hear something like that and you hear it frequently because you're able to tease out such wonderful insights from these people, what kind of juice and fuel does that put in your tank?
Learning from Guests and Personal Growth
00:47:04
Speaker
Oh, it just gives me goosebumps. I mean, I just become completely engaged in the process of learning, which is such a gift.
00:47:15
Speaker
You know, of course, we talk about the the interviews you do as an arc of a career. And would you say that the that this book coming out is illustrating the arc of the podcast? Yes, yes, yes, without a doubt.
00:47:32
Speaker
without a doubt. I had such limited space in so many ways that I couldn't really include what I originally had hoped to be able to include, which I actually put together. I should probably put it up on the website, which are some of the more difficult moments in design matters history. What would you identify as some of those difficult moments?
00:47:57
Speaker
Oh, well, certainly the the rigid soul worm in takes the for, you know, the hardest interview of my life. I had an interesting experience with Krista Tippett, which I also would have loved to have included. Because that was the decision I made after that interview, it was a decision I made to no longer do
00:48:20
Speaker
interviews that weren't face to face and in person. And again, I came to the Christa Tippett interview very nervous. She's an icon, a legend, and a great interviewer. And so I wanted to be on my game. And I had interviewed her right after Becoming Wise came out. And in the book, it refers to a period she had in her life of depression. And as I mentioned, I had had that as well. And it was many years ago, so it was
00:48:49
Speaker
Probably it was definitely after my depression.
00:48:53
Speaker
And so I was talking to her about her depression and I thought we had a really poignant, very heartfelt conversation about it. And my producer was in the sound booth after I finished the interview, I asked him how we thought it went. And Curtis, my producer is a man of a very few words, but they're all honest. He never, ever just compliments for the sake of a compliment or to blow smoke up his skirt or anything like that.
00:49:22
Speaker
And so he said, well, I thought it was good, but I wish you had asked her how she came out of her depression. Like, what did she do? And I was crushed. I was crushed. I'm like, how could I not have asked that? What was I thinking? Where did I go in that moment? Was I distracted? What happened?
00:49:46
Speaker
Now, Brendan, I generally do not listen to my podcasts once they air, because I've already experienced the interview. Curtis, I trust Curtis implicitly. He edits as he sees fit. And so after the interview, I didn't listen to
00:50:06
Speaker
I didn't listen to it again. But when I was transcribing everything for the book, of course I transcribed Krista's and read the interview, read the transcript, and found out that I did ask her. Curtis just didn't hear it. And he never mentioned it again. He never said, oh, by the way, in that interview with Krista, you did ask her.
00:50:31
Speaker
And so I was really happy. It also gave me the courage to start doing the show via Zoom and various other platforms when COVID hit because I can no longer do the show face to face. And then it also gave me the opportunity of interviewing people that weren't geographically close to me. And so that has changed over the last year and a half as well.
Project Completion and Episode Conclusion
00:51:01
Speaker
I've read that, you know, you, you consider yourself a finisher and I think a lot of people have a hard time finishing things and going through seeing projects through the end or enduring the messy middles of things. So, you know, where has being a fin, like, how did you develop that muscle to finish things? Honestly, Brendan, I think it might be a little OCD. Yeah.
00:51:26
Speaker
And I'm not saying that I'm not exaggerating and I'm not in any way disparaging anybody with OCD because I do have some aspects of OCD when it comes to neatness and organization and
00:51:48
Speaker
commitment and I really do find it to be painful to not finish something. And so that just is a way that I think I cope with reality. And speaking of finishing, do you see a conclusion to the podcast, a way to where the arc closes in on itself or is it more of an indefinite thing?
00:52:17
Speaker
I think for now it's an indefinite thing. I really love doing it. It is very nourishing for my soul to do it. It's a lot of work, a lot of work for not a lot of money, but I love it. And so I'm going to keep doing it until I can't do it. I'm
00:52:38
Speaker
Yeah, and you've said you think success is a practice, sort of like love or happiness, and it changes day to day, but you know it when you feel it. As you've crusted into this chapter of your life in the podcast, how has your notion of success changed, or how do you define it now? Well, I'm never satisfied. I think that I'm striving for feeling
00:53:08
Speaker
worthwhile, valuable as a person. And part of the way that manifests for me is being productive. And so I'm really working on trying to separate the productivity from the self worth, but I'm still working on that.
00:53:29
Speaker
Very nice. And as I want to be mindful of your time, Debbie, and as the landing gear comes out and kind of bring this airliner down for a landing, I've been getting into the habit of asking guests for just kind of a recommendation for listeners of any kind, whether that be a brand of coffee, a pair of socks, or an afternoon walk. So I might just pose that to you, Debbie. What might you just recommend for people out there?
00:53:52
Speaker
Well, I'm a big walker. I love walking, but I love doing a lot of different things. You know, from a television show standpoint, I would say I May Destroy You, Michaela Cole's series, it's just breathtakingly good. Ricky Lee Jones memoir, Last Chance, Texaco.
00:54:12
Speaker
Chronicles of an American Troubadour is one of the best books that I've read this year. A really remarkable memoir about her life growing up pre-fame and then what it was like to suddenly become so famous so fast.
00:54:29
Speaker
I love this book. So those are two things right off the bat. My wife has an incredible podcast that I love. It's called Here to Slay, and it is on Luminary and on Apple Podcasts, and I would highly, highly recommend that. So that's three things. Oh, that's wonderful. And for the few people who don't know who your wife is, it's the great and incomparable Roxane Gay.
00:54:56
Speaker
Oh, yes, I'm sorry. I should have said my wife, Roxanne Gay, has a great podcast called Here to Slay on Luminary Napa podcast. Fantastic. Well, Debbie, Why Design Matters? It's an incredible culmination of the podcast to date. It's such a wonderful book. And the podcast, of course, is an inspiration to me and millions of others, I imagine. So thank you so much for all the work you do and for coming back on this podcast. I deeply, deeply appreciate it.
00:55:25
Speaker
I really, really appreciate it. You're a wonderful interviewer and conversationalist, and it's been a lot of fun talking to you. Man, how special was that?
00:55:44
Speaker
Debbie did not have to say that I was good at this morass. She could have just said thanks for having me on the show like everyone else does and but she said what she said and now I'm flying man. I'm speechless Jerry. I am without speech.
00:56:00
Speaker
The book is Why Design Matters, conversations with the world's most creative people. It is published by Porchlate Books. It's available for pre-order and will be available everywhere February 22nd. Don't forget to subscribe to this podcast and maybe consider leaving a rating or review.
00:56:18
Speaker
They mean the world and help validate this whole enterprise. Of course, feel free to share and link up to the show on social media. Be sure to tag the show at cnfpod.com so I can give you digital fist bumps in my patented James Hetfield gifts. They're not patented by me, but hell, I'm the only one that I know who reacts to everyone out there in the Twitterverse with James Hetfield gifts circa 1992.
00:56:47
Speaker
had several incredible phone calls of late. Remember those actual phone calls? With a few trusted advisors the past couple weeks. Brain trust, if you will. All previous guests of the show. And I picked their brains about this book proposal project I'm working on. Busting my ass on, let me tell you, friend. And their generosity filled me up like nobody's business.
00:57:13
Speaker
And I was so energized by all three of these calls and I was so grateful that they spent an hour with me to hash out my biz and put my mind at ease and give me some structure to what I'm struggling to structure. And it got me thinking how important these kinds of conversations are. Not on email, not on Twitter, not over text, nothing performative, but honest to goodness phone calls. This may be self-evident to people with writing groups or reading groups, very active ones,
00:57:44
Speaker
But I suspect a great many of you are alone, toiling alone, and it sucks. Because writing is so often celebrated and lauded as this solitary act and the thing you have to wrestle with and pinning a crocodile's mouth shut. And sure, the act of writing
00:58:03
Speaker
is often solitary and it has to be at some point. But, and this is the big but, so long as you're not a vampire draining the life out of everyone around you, maybe pick up the phone and talk to a pal, talk to a writer and hash that shit out.
00:58:23
Speaker
Good friend Bronwyn Dickey, she sent me a tweet from Dinty W. Moore the other day. The tweet quoted Galway Canal or Galway Canal. I'm not sure how to pronounce it. They said, we're all in this together. It's not one of us against the other. It's all of us against the clock.
00:58:44
Speaker
I spent the first 40 years of my life largely thinking I was in competition and that I had to crush and hustle and win awards and shred.
00:58:55
Speaker
He got the picture. I figure I've got about 40 years left on this earth, with maybe 30 of that being quality, however you define quality. My only competition these days, seeing efforts, is that undefeated motherfucker, Father Time. Ball's on our courts, man. It's high time we take that shot. Stay wild, seeing efforts. And as always, if you can't do, interview, see ya.
00:59:41
Speaker
you