The Learning Leader Show With Ryan Hawk - 452: Debbie Millman - Visual Storytelling, Building Your Brand, & Fostering Your Creativity

Episode Date: December 27, 2021

Text LEARNERS to 44222 for more details... Full show notes at www.LearningLeader.com Twitter/IG: @RyanHawk12  https://twitter.com/RyanHawk12 https://twitter.com/RyanHawk12 Debbie Millman has been named "one of the most creative people in business" by Fast Company, and "one of the most influential designers working today" by Graphic Design USA, Debbie Millman is also an author, educator, curator, and host of the podcast Design Matters. Notes: Visual Storytelling is the art of using language and images to convey a narrative account of real or imagined events. How to make an effective presentation? You must know it thoroughly. Practice, rehearse. Get to the point where you can let it flow when you're in it. Don't just read what's on the slide. Use at most one sentence. Use images to help reinforce your message "Life is so difficult when you don't know what you're talking about." Ideas are easy... Strategies are hard. You need to understand that a presentation is a performance. Teaching forces you to learn your topic. If you want to learn about something, sign up to teach others about it. "I once read that the definition of insanity is doing the same thing over and over and expecting different results. I fundamentally disagree with this idea. I think that doing the same thing over and over and expecting different results is the definition of hope." "A brand is simply a set of beliefs. And if you don't create a set of beliefs around your products or services, well, you stand for nothing - you have no values and no vision." "Actually - and ironically - people aren't really interested in a new brand form or flavor as much as they are interested in how a brand can change, impact, or improve their lives. They want brands around them that make them feel special and provide some social cache or confidence." Interviewing is like a game of billiards. Each question should leave you in a position to hit the next shot/ask the next question. Be overprepared so that you can flow in the moment. "You have to listen and really focus on the person." Research everything Courage and confidence - The reps lead to confidence. Confidence leads to courage. Branding --"Branding is a deliberate differentiation." Brands aspire for consistency. "You can't metabolize regret." -- Go for it. At age 50, Debbie came out... And felt so much freedom from it "Don't edit your hopes and dreams before you can ever attempt them."

Every presentation is really a performance. And you're performing this information for people in a way that needs to be compelling, that needs to be persuasive, that needs to be open to other points of view, that needs to be challenged, and that needs to inspire people. And if you can't do that, and if you can't answer how you're going to do that, as you prepare for every presentation, then you haven't really earned the right to present yet. Welcome to the Learning Leaders Show, presented by Insight Global. I am your host, Ryan Hawk.

Thank you so much for being here. Text learners to 44222 to become part of Mindful Monday. You, along with tens of thousands of other learning leaders from all over the world, will receive a carefully curated email for me each Monday morning to help you start your week off. Right. And soon I'm going to announce how you can read my latest book, which comes out in January 2020, early. Text learners to 4422 for more details. Now, on to tonight's feature leader, the great Debbie Millman, named one of the most creative people in business by Fast Company and one of the most influential designers working today.

by Graphic Design USA. Debbie Millman is also an author, educator, curator, and host of one of the longest running podcast ever called Design Matters. During this conversation, we discuss the brand of a company and the brand of you as a leader. And then visual storytelling, how to build PowerPoint presentations that people actually want to look at. and then the skills needed to become a world-class interviewer and how it relates to billiards. Fascinating one. Ladies and gentlemen, you're going to love it.

It's Debbie Millman. Debbie, it's so great to have you here on The Learning Leaders Show. Welcome. Thank you, Ryan. It's really great to be here. So you're different than most guests I have, and that's particularly why I wanted to have you on the show for years. So there's a lot of people that I work with and that are probably watching listening that are, they're in some sort of leadership role within a company.

And part of their activities is they are giving, they're doing like quarterly business reviews. They're doing town halls. And as a part of those, they may build a PowerPoint deck. And they're usually given a deck and like, hey, fill in the numbers. And every once in a while, I find a person who throws that deck in the trash and they create their own of these beautiful images. and use of design to actually tell a better story.

And I love it when I see that. And I try to do it myself. What advice would you give to that person who's given a deck? And they're told to fill in the numbers and everything else as they give their QBR. And maybe there's a better way. And I'm not trying to lead the witness here, but I'm thinking, you know, you might have some thoughts. Yes, you are. What do you think is a better way to go about doing these types of reviews and reports?

Well, usually those types of reviews and reports are more for the orator as opposed to the audience. And so what it becomes for the audience is remedial reading because all you're getting is somebody reciting what is on the slide in front of them. That's what it is. You're wasting your time. People will check out because they can read a lot faster than somebody is actually speaking. And so they'll read it. The person is still speaking, and at that point, maybe there are three quarters of the way through reading. The other person that's in the audience is done reading, and that's when they pick up their phone.

So I think that slides should be used for directional guidance. Just one bullet point with one statement or one image and let that enhance what you're saying, not prescribe what you're saying or reflect what you're saying. So how do you coach people on this stuff? Do you ever work with clients on things like this? I work with my students, but I don't work with clients in that way. So what are some things you tell your students because you're like preparing them for this life that they're going to fall into and they may think, oh, what do I do? Debbie, my teacher told me to do this, but now everyone else does this. What should I do?

Well, a big part of what I try to teach my students is how to make an effective presentation. And you have to really relentlessly prepare. You have to prepare and visualize every scenario. First of all, you have to know something that you're speaking about so thoroughly that somebody could wake you up in the middle of the night and ask you about it and you would be able to answer without notes and without prompts. So you really need to know what you're talking about. A lot of people don't really, really know what they're talking about.

They need the slides just to read, yeah. They need to be reminded. That's one of the really interesting things about teaching is that it forces you to learn your topic. Yeah. And so you have to visualize every scenario. You have to be able to anticipate any question that you might be asked. You have to anticipate for somebody understanding, somebody not understanding, somebody liking what you're saying and agreeing with you and somebody not, and what the various responses are going to be. Because the last thing you want to be in a presentation is defensive about what you're saying. Because the minute you do that, you're going to lose everyone who then suddenly doesn't trust what you're saying and what you stand for. for. You know, ideas are in many ways very easy. Strategy is a lot harder. You know, I can ask anybody to come up with a new idea for just about anything, and they'd probably be able to have five

ideas in 15 minutes, but to really have a strategic point of view about those ideas. So a reason for being to bring those ideas to life, that's a lot harder. And so you really need to be able to understand what it is you want to convey to your audience and then create a narrative. arc to be able to do that. That just takes a lot of work. It will create narrative arcs. They just have, this is the information I want to communicate. And then they have 15 slides with 500 words on each slide.

And by the time people are finished, they want to just, you know, kill themselves. So you really want to be able to understand that every presentation is really a performance. And you're performing this information for people in a way. way that needs to be compelling, that needs to be persuasive, that needs to be open to other points of view, that needs to be challenged, and that needs to inspire people. And if you can't do that, and if you can't answer how you're going to do that as you prepare for every presentation, then you haven't really earned the right to present yet. Yeah, and I sense the reason that that's not the norm is because it's hard. It takes a lot of time. And people,

are busy. And so they think, well, let's fill in the, fill in the gaps. I mean, I've done this. So I'm not like saying. Yeah, no, I have too. I have too. That's why I know. Because we have all these other things, but oh, I got to get that presentation, man. I'm not sure. Oh. And I think that's why we do it. And yet, though, then it's such a painful exercise for everybody. Because we then with a sit through everyone else's who did the same thing. And we're thinking, why do we do this to ourselves? There could be a better way. It takes more time up front. But the end result, like most, things in life is so much more worth it. Right. Well, leaders are people that have achieved something. Yeah. And when they have reached that pinnacle in their lives, they think that they can wing more things.

And so they'll rely on their existing success to propel them into another success. But people always know when you're winging something, just like they always know when they're not telling the truth. But somehow, because leaders are leaders and they think they're a leader because they're smarter than everybody, and they very well may be smarter than most, it still doesn't take away from the fact that people are highly empathic and have senses about when somebody's telling the truth or if they really, really don't know what they're talking about. My goddaughter, years and years ago, like 20 years ago, when she was first, first, first learning about computers, she was in grade school at the time. She was super excited about it because she knew that I spent all of my time

the computer and she was trying to tell me what she learned. And she was having a really difficult time expressing herself. And she was stammering and just, just hemming and highing. And finally, she looked at me and she said, one of the most brilliant things anybody has ever said to me in my life. She looked at me and she said, Debbie, life is so difficult when you don't know what you're talking about. And it's true. There's sometimes the simplicity of a kid, or someone who just says it. It's like, yes, that's the thing. That is the thing.

We make life more difficult for ourselves when we try to talk about things that we don't necessarily know about, but we feel compelled to talk about and then get caught up in a whole series of spirals that end up in a downward spiral toward shame. Yeah. You mentioned something earlier where you said, teaching forces you to learn your topic. So I've been really pulling on this thread lately, Debbie, because I think when I work with leaders, I will always push them to teach. And sometimes I say, I don't even care what you teach.

Sign up at your place of work to whether it's teach like a little mini elective or call it whatever you want, teach a class. Maybe it's to help. It helps to start with something like you really care about. You're really passionate about because what happens in that process is all of the, the prep, all of the work, all of the like, I need to get very clear on what I believe before I'm going to share it with someone else because I want to add value. Then you do the teaching and then you get the feedback afterwards. This loop, I think teaching could be the greatest tool in the world for learning. I sense this is what you've gathered through all. Absolutely. Ryan, I have to

tell you, so I decided this semester, one of my faculty is only able to teach 12. of his 15 classes. It's a once a week class for 15 weeks. And I have been dying to teach a class on capitalism, on the history of capitalism. And so I decided I was going to fill in those three weeks with a little introductory course for my new students called Introduction to Capitalism. And as I, now, I've been teaching for 15 years. And I teach business strategy and I teach all sorts of classes on branding. And so I kind of thought I understood capitalism and I understood its origin and so on and so forth. The more I got into the history of capitalism, the more I realized, I can't teach a history of capitalism without teaching history of feudalism. And then I also need to

be able to teach something about Marxism and socialism. And there goes sort of this minefield of incredible topics that I need to be able to make sure I understand. I understand. understand the conditions that led to the conditions that brought about our world of the free market, so to speak. So, yeah, it's a really incredible exercise to be going through and really understanding what it takes to master a topic. Yeah. And yeah, this is just why I would continue to reiterate and push this. I know you're busy. I know people have a lot going on, but but forcing yourself, creating forcing functions for you to teach, to be in the mode of a teacher is when so much learning will happen. Debbie, I've scoured the world to find some of the most

fascinating quotes from you. And I would love to, I love, some of them may be older than others, but sometimes you do this and we have some fun with it because you're like, oh, I've changed a a little bit. Or yes, I believe it in some. So if you're cool with it, I'd love to surface if maybe a couple of them and then we can, we can, we can flesh them out a little bit. is that cool? Absolutely. Absolutely. So this one really caught my eye. You said, by the way, if I found quotes that are not accurate, you can tell me that too, but hopefully they are. So you said, I once read that the definition of insanity is doing the same thing over and over and expecting different results. I fundamentally disagree with this idea. I think that doing the

same thing over and over and expecting different results is the definition of hope. What do you think? What do you think? Well, you know, not to diss Mr. Einstein and any way, I still maintain that there's a part of that that's true. I do think that we can run into some difficulties by continuing to do something over and over again and expecting a different result. I think the key to it being hope is doing it slightly different. So you can still do the same thing, but I wouldn't recommend that you do the same thing in the exact same way. because otherwise, I think you do run the risk of failing in a way that is more painful. You can fail and learn, iterate and grow and evolve.

Then chances are much stronger that you will be able to create some different scenario. But if you do the exact same thing in the exact same way into the exact same circumstances, I don't really know what could possibly be different in an outcome. So I think I do have to nod to Mr. Einstein and say, yes, there is something fundamentally true about that, certainly in an empirical scientific manner, but in a more abstract manner, in a more artistic manner, I think doing the same thing over and over again

and learning from what you're doing and iterating based on that learning creates mastery. Gotcha. Is there like an example that you can think of? when it comes to that where you're doing it over and over with little iterations as you're learning through some minor failures or setbacks to then get to a point that you feel good about. The first example I can think of is Jackson Pollock. There's a really great movie about Jackson Pollock.

Marsha Gayharden is in it and Ed Harris is in it. And Ed Harris, you see a lot of his working through to his ultimate sort of understanding of what his abstract paintings need to be and what they stand for. And there's this moment where he creates the splash painting, the splatter painting. And Marsha Gay-Harden's character, Lee Krasner, says to him, I think you're onto something. I think you've broken through to something. And I think that that is a really wonderful understanding of experimenting over and over with the same sort of variations on a theme and him getting to a place where he has that breakthrough. I don't think those breakthroughs come unless you are constantly iterating your ideas

and challenging your own ideas and growing your own ideas. And that's when I think an original idea happens. Okay, I like that. Let's talk about branding. Okay. So you said a brand is simply a set of beliefs. And if you don't create a set of beliefs around your products or services, well, you stand for nothing. You have no values, no vision.

So let's expand on brand. And I want to take this two ways. One, from like a company perspective, like Nike's got a brand or whoever. Burger King, I know you've worked with them or others. But then there's also the brand of Debbie Millman or the brand of person A over here who has a job as a leader within a company. Can you maybe hit both of those branding when it comes to a company or a product or a service as well as your personal brand, the brand of a brand, the brand of a person. So that's a really, really interesting question, Ryan,

and I'm going to have to sort of deconstruct it in a bunch of different ways. Fundamentally, for me, I consider branding to be manufactured meaning. We imbue a thing with a sensibility. So we have a brand and we give it attributes and we give it identifiers, and we allow people to understand what that thing is through a transfer of communication. That communication could include symbols, it could include language,

it could include behavior. But fundamentally, that brand doesn't exist without human interaction imbuing, embedding a series of characteristics or attributes into that thing. Now, I contend that all of religion is that as well. It's manufactured meaning. Religions don't grow on trees. They don't spring up from the earth. We create a set of beliefs that we then articulate through a whole series of, of behaviors, symbols, and attributes.

Now, as far as considering me or anyone a brand, I find that to be problematic. I find anyone aspiring to be a brand, to be then saying, I am going to manufacture a persona that I am going to project out that I hope you're going to believe. No one is the same every single day. Brands aspire for consistency. Yes, they can evolve and grow,

but when they do, they need a strategy to do that. I think humans need to evolve more organically, and they grow and change. They fall in love, they fall out of love. They gain weight, they lose weight. They color their hair. They cut their hair. there's any number of things.

If you have to start assessing how you change based on how your audience is going to feel about those changes, you cease to be a person with your own organic humanity. And so I think that humans develop their character. They develop their reputation. But to think of a human developing their brand, unless you're selling something specific like a makeup line that has, has your name on it, then that's a branded product that you own and develop. But the minute you can see your heartbeating self, a brand, I think you dilate your humanity.

It's interesting, though, because I think of, like, Debbie Millman's a brand. Like, I've heard it. I've taught friends who brought your name of. I thought I wanted you to be on this for a while because of everything you've created and done and the way you think. So that's more, I think. I would like to hope that's more about my humanity. Absolutely.

You know, I changed a lot over the time that I've been a professional. I came out 10 years ago. I now have my own practice versus heading up a huge branding consultancy. You know, a lot of people would have said when I had the opportunity to be the CEO of the organization that I was president of, that that was more in line with my brand. But that wasn't more in line with how I wanted to live my life. Interesting. And so I think that I'm hoping that, you know,

you're responding more to my reputation than my planning the evolution of my brand. Gotcha. Gotcha. Okay. I understand like the differences here. I think it's like I've seen, I mean, you see them advertise go to this workshop to work on your personal brand. I don't think there's ill intentions there.

I think people. It's about kind of cultivating, I guess, their work or what they're trying to, but I understand from your perspective of where you're seeing that of, if it doesn't feel genuine maybe or not authentic to who you are because humans are I think humans in general are the world's gray it's not black and white and people are messy and I think that's the thing about whenever I'm sure this as a podcast host and as a you're a person of fame every once in a while you meet somebody and they have these expectations that you don't have any false you are perfect and that's sometimes for me as a bummer because

I'm like that is just not true like there's like a misdemeanor. million flaws and there's so much messiness here, even if you've developed this sense of listening to a podcast and you don't feel that or you don't see that for some reason. Right. And but in reality, like, no, it's there. I promise you. I mean, Instagram in a lot of ways is manufactured meaning. You're creating a persona that you want people to see.

Highlight real. Yeah. And I think that you're 100%. I mean, I've said it before myself. So we are completely in agreement. life is messy. Humans are messy. That's not what we want our brands to be. That's when we criticize our brands. Yeah. Okay. Actually and ironically, people are not really interested in a new brand form or flavor as much as they are interested in how a brand can change, impact or improve their lives. They want brands around them that make them feel special and provide some social cass or confidence.

How about that one? Well, I was with you 100% until that word confidence. Okay. My views on confidence have really evolved over the years. I think that people do seek out brands that they think will improve their confidence. And for a brief period of time, they will. But we metabolize that feeling very quickly. We metabolize all our feelings.

We metabolize feelings of hunger. We metabolize feelings of being full. And we think after Thanksgiving, we never want to eat again. And four hours later, we're picking through the refrigerator for leftovers. So we metabolize everything. We live on a planet that is constantly metabolizing. And so what ends up happening is we think we need this thing to be more confident or to be equal to others. When in fact, they're just placeholders.

and they're giving us this feeling for a little while. You know, Dan Pink would say, if your idea of happiness is a certain inch flat screen TV, you're playing a fool's game, because once we have that thing, we're going to metabolize the feelings of delight and thrill until it'll become sort of ordinary and part of our everyday experience.

I mean, I can ask anybody that's listening, as soon as you got your last promotion, what were you thinking you wanted for your next? When did you start thinking about your next performance? motion or your next raise. You know, we think we need these things to be happy and then once we get them, we tend to then want more because that view of happiness is actually really, really flimsy. We rely on it for sort of day-to-day buoying up of our confidence, so to speak. But confidence really comes from within and it comes from successful repetition of any endeavor.

And so it really doesn't come from outside stimuli unless you are engaged in that stimuli on a regular basis and feel predictively that you can assess that the next time you do something, you will be able to do it well. You know, we all have car confidence after driving for a year or so. We have walking confidence if we're able to walk. We don't think about these things. They're more sort of operational to us now. But when we start doing something is when we start doing something is when we're able to walk. we're looking for confidence. And sometimes we wait to feel more confident before we're willing to do it when in fact what we need in that moment is actually courage to take the first step

into the confidence. And then when we do it enough times, we can then build the confidence, which really is just the predictive ability to view the future with our doing something and doing it well. I really identify with that of you set like a there's like the guide post here and then you and you hit it like I remember getting a book deal and thinking leading up like there's no way I could ever do that right and then you do it and you do it again like friends give you champagne and other things and I still think of like the champagne sitting in my cabinet hasn't even been open because there was a new thing further out instantly and so and I read this quote recently and so and I read this quote recently I forget, I mean, it's probably been said by a lot of other people, but the quote is, it's not about what you acquire. It's about who you become in the process of acquiring it. And that's the thing. Like, that's really what the thing is, I feel like. Yeah, that's beautiful. That is absolutely beautiful. That is exactly right. One question that I'm really endlessly fascinated with these days

is how long does the feeling of accomplishment last for someone? how about for you? Like you've had some massive accomplishments. You've been named all these things, books, everything, right? I mean, you got you got it all. I mean, I, like, what did it feel like when you're being named like the most creative person in the world by all of these name brands? I mean, you're all over the place. Like, what are these, do they just hit you and then you move on or like, how does that go? Isn't that tragic? Yeah. Is that really? How? I'll go like yeah but I don't know anybody that does it experience that ephemeralness of that's a word of of success yeah um so many especially because I interview so many people you know they're always searching

to grow and develop and I think that's part of that metabolize when metabolize our successes in the same way that you know people say when you're grieving well it takes time to get over the grief. Well, it's interesting because it doesn't take a lot of time to get over the success. Where constantly looking for more, new, better. And I find that anybody I ask that question to now is within minutes, within a day, you know, I don't think anybody's even said more than a week. Yeah. It's interesting how that works. Before we go, I did want to ask you a question about interviewing because when I am lucky enough to talk to someone as brilliantly as you who also has spent a great deal of time interviewing people you have one of the original podcast has been in

existence from the beginning it seems like um what's like what's your desire slash motivation overall feeling around interviewing interviewing other people i love it again endlessly fascinated with how people become who they are i'm so so captivated by how humans overcome obstacles, how they manage their own grief and pain, desires, ambition, how people become who they are, especially when they are considered masters at something, is I think the greatest journey of our species. You know, how do we imagine our lives into creation? and then how do we make them what we want them to be.

It's a gift. It's a gift. So what made you start it so long ago? Like you were way, way before most or almost all. I did a Hail Mary with my career at that point. I had been working and branding at that point for 10 years. And I was for the first time in my life successful at something. I was already in my 40s at that point.

And I had an opportunity to host this little radio show on a fledgling internet radio network that was just starting back in 2004. And they approached me at the end of 2004 after an article I had written on Speak Up with my friend Mark Kingsley sort of went viral on election graphics and the branding of election graphics and they called me and they wanted me to host a radio show on branding. But because I was doing so much work day to day in branding and I had for the first time in my life felt successful at it, I had all but given up all of my side projects and anything create, purely creative, not commercially creative. And I thought, oh, here's an opportunity. Maybe I can do something

really creative and do something just with design and convince them to let me do a show that was on design as long as I included some branding, which, you know, of course you have to with design on some level. And so that's when Design Matters was born. The first show aired February 4th, 2005. And my friend Brian E Gomez-Pulasio, who was one of the co-founders of Speak Up, was lamenting to me the limited amount of time that was available for people to listen to the show. I broadcast it live on a Friday afternoon and then you had an opportunity to re-listen to it one or other time in Voice America's schedule in the wee hours of the morning. And she said, why don't you upload it to iTunes?

And I was like, what a good idea. And, you know, I did that like two or three months later. I think in June of 2005 and the podcast was born. I don't even know if the word podcast was in use at the time where it was just barely in use. It was definitely no podcast section on iTunes. It was almost like I was an indie musician uploading. Oh, I was going to say, like, what were even the other podcast that existed?

I'm not even sure. Wikipedia has a list now of the podcast that were founded in 2004 and 2005. And I think every year since, but the list, I think, begins in 2004. Are like how many are even still in existence? There can't be too many. They're about, I think, from that time, about five that are still brought. Wow. What does that feel like for you?

I mean, that's different because this is not a landmark. This is a mark of consistency and effort and work. stacking days. Like, what does that feel like? I feel like that's different. I'm proud of it. I'm proud of it. I have a book coming out in October, which is sort of a best of. It's sort of a monograph of the show. And I had to pick, I couldn't include every interview because of space. So I have about 60 condensed interviews and then another 60 sort of full page quotes. And it was an opportunity to go through every show and read all the transcripts and really relive the last 16 years in a way that surprised me.

It also mortified me a bit to understand just how terrible I was at the beginning. How long? Like, was there a mark here where you felt like, okay, I'm kind of getting getting hanging here? There's two marks. Okay. I would say the first hundred episodes of design matters are unlistenable. really, truly, unlistenable. The sound quality was terrible, and I was terrible.

And so in 2009, I started working with my producer, who I still, I work with Curtis Fox. He started producing the show. And so that's one big marker where the first 100 shows. He's been 101 forward. The first 100 shows, don't even bother. And then I would say between 2009 and 2015, I was really finding my feet as an interviewer. And so I think you can see sort of the growth. And then I would say from 2015 to now, I think I've been able to sort of bring my full self as an interviewer to every interview that I do or to most.

What, this could take an hour. So I understand that. But what is like, what are the core qualities slash behaviors of an excellent interviewer? There are a couple. The first is you really have to listen. Most people when they're in a conversation don't really listen. They talk, then they stop talking. They wait for the other person to stop talking so they can start talking again.

That's just human nature. So really being able to focus on who I'm interviewing is critical. And I do that by trying to research everything I possibly can on my guess, so that whatever they say, I can have something to be able to continue the conversation about it being about them. You know, usually conversations tend to be back forth, back forth, back forth. I like to see my conversations in my interviews as narrative arcs where I'm continually allowing. my guests to speak about their life. So it's not they're saying something and then I'm opinionating on what they're saying. They're saying something and because of what I know about what they're saying,

it allows me to then ask more questions about what they're saying because I have the information and the research to help propel us forward. So I sort of see a great interview like a game of pool, billiards. You know, when you're playing the game of pool, the object is, to get as many of the billiard balls into the pockets. So you do that by wanting to not only get the ball into the pocket, but also leave the other billiard balls in a position on the table to be able to continue the game. And that's sort of how I feel a great conversation or interview,

which is different from a conversation. The great interview is where you're able to follow wherever your guest goes because you know that much about who they are. The over preparation frees you up to be agile in the moment I sense. Absolutely, absolutely, absolutely. So I'll spend, you know, at least 10, 15 hours preparing for any interview. You know, I just interviewed Ricky Lee Jones, one of my idols. and she has a new memoir out.

I happened to already own her entire catalog of music, but I read the memoir. I really enveloped myself into her world for the last two weeks so that I interviewed her yesterday. When I was face to face with her, I would be able to have a conversation that really honored her work and gave her the sense that everything she said mattered to the interview.

So cool. That's the best when you get to kind of meet your heroes. and they live up to it. It's the best. The best. The new book, Why Design Matters. I was looking online about this. So you said, though, there are some condensed interviews within some, I just want to see it. I want to hold it. I'm excited for that moment. Can you share the actual makeups of the book and why we should be so excited about it? I mean, I am, but I want to hear more about it from you. Well, there are five essays in the book also, which I'm really happy about. I wrote an essay about sort of the history of the show and how it happened and high moments, low moments and so

forth. Tim Ferriss wrote a great, great introduction for me. God bless him. He is just a fairy godfather. My wife wrote one, Roxanne Gay. Maria Popova wrote one, my dear, dear friend from brain picking. She wrote a remarkable essay on what it means to live a life and sort of reflect on a life. at the same time. Zach Pettettit, who is, who was the former editor-in-chief of print magazine, wrote a remarkable essay for me, and Steve Heller, the great design historian. So there's those, which is just worth reading because they're so wonderful. And then, as I said, 60 interviews.

I wrote this book during COVID, and I had a deadline. And I was intending initially to do a vast photo shoot with the guests that I chose to include. But obviously I couldn't do that. So I ended up photo editing the book myself and worked with really amazing photographers to go deep into their catalogs to find really remarkable photos. Every single photo had to have a common denominator, even though they were different photographers. And that common denominator is soul. So when you look at the photo, you feel like you're looking into the mind of the person. And it was really hard to do. And it was really hard to do. that, but I think I did. What are some of the pictures that you chose? Well, the guests include

Is it of the guests? Okay, so you actually did have the photographers. I thought you meant like they were just taking like in nature or because I thought it was a COVID. Okay. Yeah, no, I couldn't. I couldn't do a photo shoot. So I had to work individually with photographers to go into their catalogs to get photos. Wow. So I contacted. So I worked with 50, 60 photographers. Wow, that sounds like a lot of But it was, but I'm so thrilled that I did it. Yeah. Gorgeous, gorgeous photographs. And so that is what I feel.

It's a, it's a coffee table book. It's 10 by 10. It's almost 400 pages. Alex Kalman designed it. So another, another really interesting story. One of my heroes, as I was a young baby designer growing up, was Teapwork Kelman, the late great genius, you know, one of the most important designers of the 20th century. And I'm also a huge,

fan of Myra Kalman, who was his wife, who is still a remarkable illustrator. Well, they had a son named Alex Kalman, who's now, I think in his 30s. And my agent recommended that I work with Alex. And so Alex Kalman, the son of two of my heroes, two of the people that have influenced my thinking about design and illustration, more than anyone really, designed my book. Wow. So cool. I'm a pump for that thing to read it. All right, Debbie. One last question. You know, this is for someone maybe who's a little bit earlier in their career. Maybe they graduated college in the last few years. They want to leave a, they wouldn't leave a dent in the world in a positive way. They want to impact people in a positive way. They want to leave them better than they found them, right? Those types of people, the ones that we want to hang out with typically. What are some general people? of life slash career advice you would give to them?

Well, I've learned the hard way. Don't edit your hopes and dreams before you even attempt them. You know, going back to this whole idea of courage and confidence, so many people, and I know this because I teach undergraduate college, so many of the seniors, that I talk to are already saying, I really can't do that because I'm not good enough. I'm not smart enough. I'm not pretty enough.

I'm not thin enough. I'm not this enough. I'm not bad enough. And I totally get it because I did the same thing. Like I remember the moment in 1983 standing on the corner of Bleaker Street in 6th Avenue in Manhattan thinking, I just don't think I can do that. I think I'm going to do this instead because I think it's easier. Well, nothing is easy.

Everything takes hard work. Every job has its hard days and give yourself the opportunity to try it before you refuse to even consider it. What was there a turning point for you? After 1983, you're on Bleaker Street. You're like, I don't know about this. At the time, I really wanted to be an artist and a writer. And I just couldn't envision how I could ever make that happen. And so I chose commercial art because I knew that I could pay my rent or at least I could try.

But I've loved what I've done in this career. But the idea of being a writer and an artist never went away. You know, one, we could even metabolize grief, but you know what we can't metabolize? You know what we can't metabolize, Ryan? What? Regret. There's no closure to regret. So we can't metabolize.

It lives with us forever. And so wouldn't you rather try something and experience the attempt than having to regret not trying for the rest of your life? Do you have regrets? Not anymore. But for a long time, I did. Yeah. What were they? Well, not pursuing doing more art, not pursuing writing, not pursuing sort of my own practice.

Yeah. So when was the moment where you said, I'm not going to have these. regrets anymore. I'm going to do something about these regrets. 50. 50. Was it the number or was it something that happened? It was the number. Really? Like, if not now, when? So what happened on your 50th birthday? I came out. Wow. Wow. And then what? And then I felt a lot freer. I felt a lot less judged. I realized that the secrets were killing me and no one else. And, you know, I talk about this on Tim Ferriss's show a little bit as well. Shortly thereafter, I started working with Mariska Harcatei at the Joyful Heart Foundation and helped create the No More movement and started to disclose some of my own early experiences that I had always felt ashamed of.

And that also opened me up to the possibility of evolving and growing in ways that I hadn't experienced and giving up that shame as well. really showed me that I was that holding myself back was was probably the most damaging way to live. And so over this last 10 years, things have really changed, I think, quite dramatically in my psyche and how I approach my. I really, I really appreciate you sharing that. Do you think that could have been done at 30? Not for me.

It certainly is for other people. the time, like you have the sort of psychological resources to be able to do that. Yeah. Every, every journey towards, I guess, it sounds kind of corny, but, you know, self-actualization is different, you know, and some people get it, you know, their masters at something in their teens. I mean, I just watched the Olympics and was astounded by the mastery that the teenagers had in the skateboarding and swimming and diving.

And I was like, oh, my God, this is just incredible. How does that feel to be so amazing at such a young age? Yeah, I love it. Debbie, thank you so much for sharing. I really appreciate how much like you're willing to just open up and go there. I never know what to expect when you meet somebody that you've really looked up to for a long time. You're certainly one of those people for me. So to joy, when you responded to my first email, I'm not going to lie.

I was like, this is sweet. So thank you for that. I appreciate it. I am pumped to read Why Design Matters, Conversations with the world's most creative people coming out in October 26, I believe, correct? Yes. And look at it too, because I know it's going to be beautiful as well. Where else would you send viewers, listeners to learn about you online? Oh, just Debbie Milman.com.

That's my website. It's a little bit outdated, but, you know, cobbler shoes kind of thing. I think it's kind of cool. I was going to ask you who designed it. Oh, Armin did. Oh, he did. Okay. So it's really well done.

Well, Debbie, thank you so much again, and I would love to continue our dialogue as we both progress here. You have one of the greatest radio voices I've heard in a long time. We've talked to you for hours. Thank you. I appreciate that and excited to do this again. Thank you. All right. Debbie is one of those leaders that the more you talk with her, the more you like her, and the more you want to continue talking with her.

That's not the case for everybody, but it certainly is for her. I just, you can probably sense it in the tone of my voice as we went. I just love the story she told and the manner in which she told them and her courage and the changes she's made in her life. And it feels like she's fully living authentically. And you can tell in the way that she responded with so much care and curiosity and thoughtfulness. I hope you enjoyed it. A few takeaways from my notes. Interviewing is like a game of billiards.

each question should leave you in a position to ask the next one, or in a billiards case, to hit the next shot. The best players are the ones who not only knocked the ball in, but leave the white ball, the one that you use, the cue ball, in the position to hit the next one in. And I think part of that is being over-prepared so that in the moment you just let it go. You just flow.

And I thought she really illustrated that well when it comes to interviewing. And then teaching forces you to learn your, topic. If you want to learn about something, sign up to teach others about it, that process of preparing and then delivering what you've learned. So much learning for you will happen because you're going to be trying to add value to the lives of others. And that process can be a forcing function for learning. And then don't edit your hopes and dreams before you can ever attempt them. Now, normally when somebody says something like this, you kind of roll your eyes a little bit, but not when Debbie did for some reason.

I really enjoyed it. I thought it was a cool part. I thought it was inspiring. And I hope it was for you as well. Once again, I just want to say thank you so much for continuing to spread the message and tell a friend or two. Hey, you should listen to this episode of The Learning Leader Show with Debbie Millman. She'll help you become a more effective leader.

And because you do that and because you continue to write reviews on Apple Podcast and rate the show, hopefully five stars, you are continuing to give me the opportunity to do what I love. on a daily basis. And for that, I will forever be grateful. Thank you so, so much. Talk to you soon. Can't wait.