In this episode of Daring Creativity podcast Debbie Millman shares her transformative journey from a pivotal class with Milton Glaser to becoming one of the most influential voices in creative conversations. 

Through her 20-year podcasting career with Design Matters, ownership of Print Magazine, and leadership of the world's first Masters in Branding program at SVA, Millman reveals the power of writing your future, choosing courage over confidence, and redefining failure as simply giving up on yourself.

The conversation explores her famous 10-year plan exercise that has changed countless lives, the evolution of deep listening skills, and her meticulous research process that unearths hidden gems from guests' histories. Millman discusses navigating different life decades, the involuntary nature of fear, and why AI cannot replace the soul of original creativity. 

She demonstrates how creating your own opportunities—rather than waiting to be chosen—can lead to extraordinary influence and meaningful work that spans decades.

Key Takeaways

• The 10-year plan works: Writing a detailed essay about your future life from waking to sleeping can manifest remarkable changes, but requires genuine commitment and time
• Courage trumps confidence: Confidence only comes from successful repetition of past experiences; courage is what you need to step into the unknown first
• Redefine failure: The only real failure is giving up on yourself—everything else is just losing, which is part of the natural process of growth
• Fear is involuntary: Our reptilian brain creates fear to protect us from uncertainty; we can't eliminate it but can control how we respond to it
• Deep listening is a skill: True listening means following your conversation partner rather than waiting for your turn to talk; preparation enables this flow
• Research creates magic: Spending hours in "wormholes" of research allows you to meet guests wherever they want to go in conversation
• Life stages bring different challenges: Each decade has its focus—twenties for experimentation, thirties for establishment, forties for plateau-breaking, sixties for "if not now, when?"
• Create your own opportunities: Rather than waiting to be invited into the "best band," build your own stage and invite others to join you
• AI can't replace soul: While AI excels at combinatorial creativity and research assistance, original creative work still starts in human brains and hearts
• Longevity builds influence: Staying committed to work for decades allows you to evolve, improve, and eventually lead in ways that short-term thinking cannot achieve

Daring Forever. Podcast with Radim Malinic

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Debbie Millman: [00:00:00] I think that failure, the only real failure is when you give up on yourself, everything else is losing and losing or rejection and that's fine. we can't win every race. We can't. We can't win anything all the time. It's just not the way the world works, unfortunately.

Wouldn't it be great if it did? I think that the only failure is giving up on yourself, and there's a difference even between understanding that you might need to do something different. But if you just give up in defeat, maybe you just needed a little bit more time.

I think there was a great football coach, I can't remember his name, but I can remember the quote. He said, I never lost a game. I just ran out of time. I loved [00:01:00] that.

Because that's a mindset,That's a mindset of if I had more time, I'd have done it.I would've prevailed. And I think that's really beautiful. 

Welcome to the Daring Creativity Podcast, a show about daring to forever explore creativity that isn't about chasing shiny perfection. It's about showing up with all your doubts and imperfections and making them count. It's about becoming more of who you already are. My name is Radim Malinic I'm a designer, author, and eternally curious human being.

 I am talking to a broad range of guests who share their stories of small actions that sparked lifetime discoveries, taking one step towards the thing that made them feel most alive. 

 Let me begin this episode with a question. Are you ready to discover what happens when you dare to create? [00:02:00] 

Today I'm talking with Debbie Millman, a writer, designer, educator, artist, brand consultant, and a host of the original creative podcast Design Matters that has been on air for the last 20 years. in our conversation we covered a broad range of topics from 

Exploring have famous 10 year plan exercise that has changed countless lives to mastering deep listening and meticulous research process that unearths hidden gems from guest stories. Debbie also discusses navigating different live decades, the involuntary nature of fear and how creating your own opportunities rather than waiting to be chosen, can lead to extraordinary influence and meaningful work.

It's my pleasure to share with you my conversation with Debbie Millman.

Radim Malinic: Debbie, it's my pleasure to have you here today. How are you Doing

Debbie Millman: I'm good. How are you?

Radim Malinic: well, I'm very excited to have you here [00:03:00] because just before we started recording, I had to tell you that if it wasn't for not everything that you've been doing, especially podcasting for the last 20 odd years, I wouldn't be doing what I'm doing. Potentially many hundreds of others, in this creative sphere wouldn't be doing the same thing, 

Debbie Millman: Thank you. You're making me blush and you're far too generous, but I appreciate it nevertheless.

Radim Malinic: I normally say for those who never heard of my guest, can you please introduce yourself? But I'm thinking. Do we need to do interaction?

Debbie Millman: I'm happy to do whatever you want. I'm in your very capable hands.

Radim Malinic: Excellent. So who's Debbie Millman? What do you do?

Debbie Millman: I am, as you mentioned, I'm a designer and a writer, and I'm one of the owners of print magazine.com and I've been writing for print. Oh gosh, for about 20, a little over 20 years, although I only became one of the owners about five years ago. And I run a graduate program, which is where I am right now at the School of Visual Arts in New York City, and I [00:04:00] co-founded the world's first ever master's in branding in 2010 with Steven Heller, my very dear friend and mentor, and somebody I consider my fairy godfather, and I am.

The host of a podcast called Design Matters, which has now been on the air for 20 years. I tend to do things for long periods of time, as you can see.

Radim Malinic: absolutely. And I think I always like when you talk about something that you've been doing, then you become ahead of it. So be it's, the print magazine being the school of Visual Arts, like you stay and long enough so you can actually be in charge. 

Debbie Millman: I love that.

Radim Malinic: I mean, that's my observation.

Debbie Millman: just slow and steady.

Radim Malinic: Basically stay there until everyone disappears and go well, I will be in charge for a while. Debbie, I wanna take it actually 20 years back when you did a class with Milton Glaser, which was one of the pivotal classes and one of the most important sort of. Things in your life and [00:05:00] it little did you know how much of an effect and impact would it have on potentially hundreds of others? because in your class with Mountain Glazer, he asked you to write an essay to yourself, and it's such a fascinating story. I would love to know there'd be more about it.

Debbie Millman: Absolutely. this was 2005, so exactly 20 years ago. And, because I was a writer for Print Magazine and at that time the magazine was a paper magazine, and because I was a writer, I would get the writer copies that came right off the press as opposed to waiting for it to be mailed through a subscription.

The way that, anybody that had a subscription would get it in the mail. And when I got it, I remember it was January of 2005, I was looking through it and I saw an ad in the magazine for a summer intensive. With Milton Glazer at the School of Visual Arts. Now, I didn't teach at the [00:06:00] School of Visual Arts.

I barely knew anything about the School of Visual Arts other than a few of my friends that were fine artists has had gotten their MFAs from the School of Visual Arts. And that's pretty much all I knew about it. But because I got the magazine early, I was able to apply early to this class, which was first come, first served.

 And I got in because I had this early edition of the magazine. And so before it went out to the general public, I got it and I was told when I called to apply that I was the first person to apply. So they were like, oh, the adss running already. And I was like, oh yeah, I got an early edition of the magazine.

 So that August, I took the summer intensive with Milton and. Ostensibly it was for people that were, mid-level professionals, which I certainly was, that were looking to [00:07:00] reboot their careers that they might have felt that they were, At a standstill or had reached a plateau, had to sort of take your next step in, in your career and in the world.

And it was life changing. the final exercise in the intensive was to write an essay, thinking about what your life would look like five years into the future. So a five year plan. And he asked us to write it from the moment we woke up and opened our eyes until the moment we closed them and went to sleep. And he said that it was a very powerful exercise. He didn't quite understand why that he'd been teaching for many decades and that. Teaching was the most important thing he felt that he did with his life, and that for whatever reason, he'd always hear back from students telling him that the exercise profoundly changed their lives, and so much of what they'd written about had come true or all of it had come true.

And so he didn't quite understand the woo magic of it, but he'd seen [00:08:00] enough evidence that it was something that seemed to be rather successful for people. And so I. I put my heart and soul into it. I wanted so much of my life back then. It was in my mid forties and I was longing for a different life, and I was.

Completely open with what I was hoping for in my life at that time. And so not only did I write a really long essay, I also made a list. I made a list of all the things that I'd be doing in 2010, and I took it very seriously. And then I put it away. I was writing it in a journal. That I was using at that time, finish the journal, put it in a stack of with, put it in a pile of other journals that stacked up in one of my drawers, and the next year I remembered I was looking for an address.

I knew I'd written down the address of my grandfa, my grandparents. Home [00:09:00] in Borough Park and I, when I was growing up, said they no long, they were no longer even alive. they had moved to Florida and all of that, but I wa I was thinking about it and I wanted to look it up on Google Maps and remember it.

And I remember that I'd asked my mother for the address and I'd put it in that book and forgot about that as well. Remembered that the address was there. Went to the journal, opened it up, came across the essay, and I was like, wow. Even within a year of writing the essay, things had started happening and I was now.

Being offered an opportunity to teach at the School of Visual Arts, I was asked to be, to join the National Board of A IGA. And these were very big audacious goals that I had at the time that I didn't even think were remotely possible. And the only reason I had teaching at SVA on my list was 'cause there I was at SVA learning and I had, I wrote this list of things in.

Over the years, it just started to, they started to manifest one [00:10:00] after another. Now, it wasn't that they only just plopped in my lap. It was also some things that I very deliberately tried to get, but I'd mostly forgotten that they were things that I had written about because they were just things that I wanted anyway.

And, I think 13 years later, every single one came true. And because I was always looking to expand the type of classes that I was teaching, and Milton had to give his approval of my teaching at SVA and my running the grad program. when he stopped teaching, I asked him if I could start using that exercise in my classes and he said yes.

I told him that I wanted to expand it though to 10 years, because I felt like five years. Especially if I was doing this with young people. Wasn't enough time, it was just a blip. And so I felt like people needed more runway. And so I've been teaching it ever since, changed it to a 10 year plan [00:11:00] and for whatever reason, of all the things that I do, people are very, mostly always interested in this.

And I don't know, maybe because it's more magical than anything else that I do, and in many ways more optimistic. But, people really do seem to love the idea of it.

Radim Malinic: Well, thank you so much. the reason why I ask you about this story, ' cause one of your former students, Donne Goed, who was the first guest of this 

season, I was like, I was told her, look, this is the guest I've got coming up and I've got Debbie coming up, and she said,

 Debbie's class was incredible because first of all, she made you ask yourself questions about what you really wanted, and in my case, I've manifested almost everything that I have written in her class. The more she taught you how to present yourself and a guide.

How to get you what you wanna be is One of the sentences that also changed me was the courage is more important than confidence.

 She gave me a lot of confidence into coming into workplace, and I oh her Lord, and I don't think she realizes. She's phenomenal, incredibly smart and beautiful [00:12:00] human. You see the things that you manifested in that Milton's class, it starts at this.

Pyramid effect. I don't know how to describe it. It started things you wanted to do something for yourself, and this is how you've influenced so many people along the way that you know, when your name is mentioned. These kind of reactions come back. What I want to know, Debbie, when you said you basically, it was quite clever how you got there through the early edition of the newspaper, so on the first come, first serve basis, but you said you were in your mid forties.

What is it about our mid forties that. Kind of make us think in a way that, you know what, maybe there's a change. I need to rethink what I do. Look for new, ideas, opportunities. And in your case, you just wrote them in an essay, kind of forgot and only to find out a bit by bit. 13 years later, all of them has my manifested themselves.

Debbie Millman: Well, I think that if we look at our lives through the decades, our [00:13:00] twenties are very much about establishing who we are, experimenting, playing, searching, longing. Then we move into our thirties and I think we start to get a little bit more serious about our careers. Some of us get married, we start to think about a family.

We start to accrue the more mature aspects of adulthood, and I think by forties you have achieved a lot of what you'd hoped for in your twenties, if you're lucky and. You begin to consider other things, you start to consider time in a different way. At that point, you know your life is probably halfway over unless you're really lucky and live, a little bit longer into your nineties or a hundred and so things become slightly more [00:14:00] both.

Tangible, but also amorphous. you want more, but you're not quite sure how to go about it, and by the time you're in your forties, it's a little bit harder to experiment. one of the things that I've learned as I've gotten older and wrote about in my last book was as I've gotten older, I find it.

 A lot more difficult and vulnerable making to do things that I'm not good at. I don't wanna be humiliated, I don't wanna be embarrassed. I don't wanna seem less than and. It's harder to start new things because I don't want to feel silly or look silly. And so when we're in our forties, I think we're on the one hand trying to reach mastery, but also trying to consider other possibilities.

Paula shares always said that the fifties is about okay, you've made it lifetime achievement awards, if you're lucky, et cetera, et cetera, et cetera. I don't know that she went beyond the fifties at the time. I think she probably made that chart. It's a wonderful chart. I'll look [00:15:00] for a link and send it to you.

I don't know that she went beyond the fifties, 'cause I don't know that she was beyond the fifties at the time she wrote it. But now that I'm in my sixties, the big question for me, Randi, is if not now, when you know, what am I waiting for? And I've done a lot of things, but there's still a lot of things that I haven't done.

And. A big part of not having done them is fear in doing them and being a beginner at something, or being inexperienced, or not being successful at something that I really want when I expect a certain level for myself in a ver in the various things that I do.

So I expect something to look a certain way and sound a certain way and have a certain sense of what I want the outcome to be. Whereas when you do something new, you have no idea. And humans hate uncertainty and I hate uncertainty. And so, That's what I'm grappling with now a lot in my sixties.

What do I want for this last third? If [00:16:00] I'm lucky of my life and I want a lot, I want more than I even had ever wanted before, only because I do feel that, I hate to use the word, but sort of desperation of time running out and I don't wanna sound like a Debbie Downer, and I'm the only person that's allowed to use that term. Towards me, and that's it. just letting you know now. but nobody's gonna live forever. But when we're 20, we think we will. When we're 40, we hope we will. And when we're 60, we know we won't. And so I think that to me has become the underlying mantra of my life at right now.

Radim Malinic: When you describe this beautifully, when you said it's harder to start, it's harder to know to do new things, I was thinking like, is there element of unresolved self-acceptance? Is there something that. I mean, I was, let's be honest, I was quite [00:17:00] surprised when you said, I'm getting older and I'm finding things harder. Because I was riddled with anxiety and insecurities when I was 20, but it was the medium of creativity that kind of changed the lane for me of, okay, you can focus on this. this is your hideaway space. This is your escapism, and you can be something and you can do something that way. And we sort out rest later.

When I stopped worrying about, the perfectionism or am I doing the thing right or no? Do I care what people think about my work? I felt like the element of self-acceptance came much, much, stronger and I could let go of thinking whatever people think doesn't matter.

Oh, I've never gotten to that point ever. I don't know that I ever will. It would be a great accomplishment if I could say, I have no F's left to give about what I do and how other people perceive me. Well, I haven't turned into a psychopath, I mean,

Debbie Millman: Oh, I know. I can tell I wouldn't, I've heard very good things about you.

Radim Malinic: but it's the element of letting go a little bit. But I was surprised when you said that,[00:18:00] we've taken it back to, to donne's. when she said that you told her that the courage is more important than confidence. I am. This topic of daring creativity, daring forever as a topic of my next book, and it's not a book about jumping out of planes or doing something stupid, it's about actually doing the thing you would regret never starting.

 and it's a book about courage, self-acceptance, curiosity, and gratitude. I would like to know your take on the difference between confidence and courage.

Debbie Millman: Oh, absolutely. Before I do that, I don't, I don't wanna forget to say this, I just saw Dena's new film that she did with Santiago Caria. It is amazing. The work that she is doing is just extraordinary. And, she was my student 10 years ago, I had this incredible class of students. And there's, I don't know, maybe 10 or 15 that have really gone on to like super [00:19:00] stardom.

and she's one of them. And Santiago shared a link with me of this little film that they made. And I say little only 'cause it's short. It's really not little. It's quite grand. but it's magnificent. and so I just wanted to make sure I told you that, 

 So confidence. I hear over and over again in my classes. I'll do that when I feel more confident I'm gonna do that when I feel more secure. And I ask them when they think that's gonna be, like, how are you gonna get that way? You can't go into a supermarket and buy a box of confidence.

It's not gonna work that way. Confidence my definition of confidence is the successful repetition of any endeavor that you have. Confidence based on previous experience. Keywords, previous experience that the last time you did that thing, you didn't fall on your face, that whatever it was, a [00:20:00] podcast, a marathon, a meal that you were making, that somehow you created something that wasn't a failure, and it could be something that you've done.

many times. Or it could also be something that because you've been so successful at other things, you feel like you can have that success, follow you into something else. But the key here is understanding that you've built a foundation of confidence based on the successful repetition of any endeavor.

 So let's go back to the beginning of attempting that endeavor, that attempt. That particular endeavor had no certainty associated with it. When you initiated the journey and what provoked you to do that, what motivated you to do that? What gave you the sense that you could do that? Two [00:21:00] things. Courage and hope.

Courage and hope. And so you needed the courage to step into that certainty. I'm sorry. You needed that courage to step into that opportunity, that endeavor before you knew what the result would be. The confidence only comes after the result. It never comes before, and so you need to be able to have some faith.

In your own courage to buoy that courage up, to take that first step. And if you think back to all the things we learned how to do, eating, talking, pooping, these all take time. we can't even go to the bathroom without potty training. So why would we think that? [00:22:00] Anything else any more complicated than that would be something we could just do successfully out of the gate.

 We can't, that's the first part of this. The second part is that we as humans. Hate uncertainty. The reason we hate uncertainty is because our brains started as reptilian brains and have evolved over time to have three parts, which are reptilian, mammalian, and the neocortex. And the neocortex is the part that we're all very familiar with.

We use it to. Our awareness will creativity, all of that is controlled in that part of our brain. The mammalian brain is what makes us wanna be connected and social and take care of each other. The reptilian brain is all involuntary action. it controls our metabolism and our heartbeat and our heart blink eye blinking.

Things that we don't think about, they just happen in our bodies. And part of that. [00:23:00] Involuntary control are is where our fear factors come in. If I were to walk across the street and nearly get hit by a bicycle in New York City, I wouldn't have to will my adrenaline to inject its cortisol in me. I would be immediately, instantly impacted by my adrenaline.

 I would not think adrenaline kick in. It's all involuntary. And so when we think about. What our prehistoric brains are trying to keep us safe from, it's anything that we don't know, it's anything that would make us feel vulnerable and uncertain. What is that? The future, what is that? Not doing something that I've never done before.

And so between our. Need for certainty and our requirement of courage, it makes anything, any precipice that we are about to cross or wanna cross without knowing what the [00:24:00] outcome is going to be. Extremely stressful.

Radim Malinic: When you mentioned when you ask people like when you're gonna do it, and they say, I'll do it when I'm more confident. It kinda reminds me of when you go, when you put people in gym for, in January, usually when they feel guilty about Christmas and there'll be a PT trainer, I will say, oh, can I show you some moves or can I show you what to do?

And people would say, I'll do it when I feel a bit stronger. I do it when I feel ready. Like you feel again, I think we, we go to this sort of fear of not being enough, the fear of not being, quite rightly accepted. And when you talked about sort of bicycles and, and.caught this whole, it made me think of a quote by,a cycling coach called Charlie Gels and he works for EF Education and.

His quote, which I'll read to you in a second, made me think about difference between failure and losing. I think when we talk about confidence and courage, I think we potentially have hijacked meaning of the word failure because he was talking to his team just before the race at Tour de France [00:25:00] and he said it's okay to lose.

It's not okay to fail because losing is something we do over and over again as we try to win a stage toward De France. Stage failing is not doing what you want to do the way you want 'em to do it. And I think we are sometimes so harsh on ourselves as creatives and are sort of gentle soul thinking, I'm failing here.

Even though we do what we wanna do the way we want to do it, we just potentially haven't accepted that. Sometimes you're gonna lose.

Debbie Millman: Well, yes and no. I mean, I mostly agree with that, but I think that failure, the only real failure is when you give up on yourself, everything else is losing and losing or rejection and that's fine. we can't win every race. We can't. We can't win anything all the time. It's just not the way the world works, unfortunately.

Wouldn't it be great if it did? I think that the only failure is giving up on yourself, and there's a [00:26:00] difference even between understanding that you might need to do something different. But if you just give up in defeat, maybe you just needed a little bit more time.

I think there was a great football coach, since we're talking about sports, that said, I never lost a game. I think he was the coach of the Green Bay Packers years and years and years ago, and I can't remember his name, but I can remember the quote. He said, I never lost a game. I just ran out of time. I loved that.

Because that's a mindset, that's a mindset. That's a mindset of if I had more time, I'd have done it. I would've prevailed. And I think that's really beautiful.

Radim Malinic: I think you beautifully said it, that failure is just, when you give up because everything else is losing. Because how many times would you see internet meme that says, it's a fear of failure and I've got a fear of failure, but no one's got fear of giving up. People just think that what they're doing right now is potentially, stopping them from sort of [00:27:00] progressing somewhere else.

Debbie Millman: that. I love that we talk about fear of failure, but not fear of giving up. That's good. Hope you put that in your book. That is really good. I've never heard that before and I really love that.

Thank you.I think the word failure, I think. Is unnecessarily heavy. everything is a progress. Everything that we do is taken us somewhere. you talk about 2030s, forties, like we are always on that trajectory going forward and forward.

Radim Malinic: Like none of us would ever decide to stop and say you know what,I don't want to pursue this thing because I'm too scared, or, I'm this because

Debbie Millman: the thing is. 

Radim Malinic: we still have to go.

Debbie Millman: Yeah, but this is what, this is the thing about fear of failure. Fear comes before failure. It's fear of failure. We're not talking about fear after failure.

Radim Malinic: Yeah.

Debbie Millman: something else. But that fear before the failure or before anything. Before anything. That's the thing we, that's part of the [00:28:00] involuntary behavior that I was telling you about before.

We can't prevent ourselves from feeling the vulnerability of the unknown, which some people see as fear and often is an actual terrifying feeling. We can't. Prevent that anymore than we could prevent our heart from beating or our eyes from blinking or needing to go to the bathroom. I mean, those, these are things that are involuntarily happening in our bodies, and it's kind of an interesting concept that all of these things are happening in our bodies without our permission.

They're just happening. We have no control over them. I've talked about the fact that we have no control of what's happening in our bodies. God forbid I could be growing a tumor right now and I would never be knowing it until it presented itself. Now, hopefully that's not happening. I'm just using this as an example.

Radim Malinic: Yeah.

Debbie Millman: [00:29:00] I have no idea. my mother-in-law early this year passed away from cancer. when she was diagnosed, she was at stage four. She had no idea. She had no idea what was happening in her actual body. We also can't control anything that's happening outside of our bodies. right now it feels like in this world we have no control over what's happening.

 So what actually can we control? Maybe our behavior, maybe we can control our recognition that these things are out of our control and how much are we gonna let these things that are out of our control impact the way we behave and live. So we're not gonna be able to get rid of the fear, because the fear is part of our physiology.

 It's part of the brain that controls all of our involuntary behavior. Fear being one that is there to protect us.

Radim Malinic: Debbie, you've spent the last 20 years, if more than 20 years, talking to people, talking about their stories, talking about their careers. You've learned a lot about some incredible minds, [00:30:00] creative minds, but I'm sure you've learned at the same time a lot about yourself.

 What was the process of interviewing people and getting to understand how we sort of. operate how we think and how we are pretty much very alike, even though we are quite unique.

What was it that you've learned?

Debbie Millman: I think over the years my process and approach to my interviews has evolved quite a bit, and so for me, the work that I do before the interview is a large part of how I approach. Each interview because I get to know the person through my research and then try to use that learning to craft a conversation that they will be most comfortable in and that they're part of the conversation becomes easy and not anxiety making.[00:31:00] 

And so I've learned. a little bit how to do that. I hope, and I've learned how to listen. In a way that I didn't before. people think they're listening, but really they're just waiting for somebody else to stop talking until they can start talking again. And so it's not as much, and I learned that, I've had some producers and couple of other folks that.

Our avid listeners shared different things that I didn't know I was doing, that they helped me understand that maybe I shouldn't be doing them. and that's great. you can only seek out criticism is another thing I always tell my students, seek out criticism because you want to know what people.

Don't like about your work. That doesn't mean you have to change it, but it's often better just knowing. And if enough people tell you the same thing, you might wanna consider evolving it just a little bit.

Radim Malinic: your research is quite phenomenal because you get your guests to relive some of situations. When they ask you, [00:32:00] Debbie, how did you find that? where do you go to these corners of their deepest, darkest history and secrets where you can unearth those gems?

Debbie Millman: Well, I just go deep, deep, deep, deep, deep into Google. I spend a lot of time reading. As much as I can of whatever it is that my guests have written, produced, created. And the internet is a really vast place now. And because I do love to read and because I do love to go into these wormholes, and that's essentially a big part of my job now.

That I find it glorious to be able to do it, and a real privilege and hours can go by and I'll look up and I'll be like, oh my God, how did that happen? Because I'm reading and going from one place to another. And also with podcasting, you do get a lot more. And so because there are podcasters that I really rely on myself to conduct [00:33:00] really good interviews if they've interviewed somebody that I'm going to interview.

I have those interviews transcribed. I might or might not actually listen, but I will read them and then I'll take parts of those interviews that I wanna ask more about into my interview. And so I'd say something like, I understand you've said X, Y, Z. What about X, Y, Z was compelling to you, or whatever it is that I'm following up?

So I've talked about this before as well. I see a great interview, like a game of billiards where the point in billiards is not so much volleying like tennis billiards. You want to have the billiard balls spread out over the table so that you can get. Each one into a pocket and then still leave the billiard balls on the table to be able to navigate into other pockets.

 And so I [00:34:00] need to be prepared wherever my guest is taking that billiard ball that I'm following, and I can go there with you. And a lot of the skill that I feel like I've developed is actually knowing. When to edit or pivot. And so it's my job to know as much as I can if my guest suddenly goes 10 years into the future.

So they go directly from something in their childhood to something in their college years to. I have to be very willing and it's hard to do to follow them there and not backtrack. Oh, there's this one other thing I wanted to talk to you about when you were 10 years old. Occasionally I'll do that very occasionally, but generally speaking though, it might seem like I am leading the conversation.

Any good dancer, like any good dance team, you need to be in sync. And so I'm really following them. I might be the person that [00:35:00] asks a question, but the first question I ask then takes us to wherever they are interested in going, and as long as I've done my research, I can keep up with them. If I haven't, then I'm just asking questions like, so.

Tell me how you got here. I could be talking to somebody seven year, 70 years old. really, you want 70 years of history in an answer. So, I try to anticipate anything that they might be interested in talking about, and then have enough information about that topic that I can actually have a conversation with them that's meaningful to them.

If it's meaningful to them, it'll be meaningful to my listener.

Radim Malinic: I think the testament to a good show is when people come to you afterwards and they say, Hey, thanks for having me on your podcast. And by the way, I thought you way too much. I thought you way too much. Like you got really out of me, not so much. And I'm like. I didn't even ask you half of the things, you just lead the conversation and you [00:36:00] just let people talk.

And the active listening is such a gift because ultimately, personally, from experience of doing this things, being inspired by someone so thorough as you are, it's an experience where when you actually, when you leave space for others to show up for themselves and actually tell you about them, you realize that.

It carries you more than a piece of creative work that you are like, Hey, do you like my design? Do you like my days? Do you like my illustration? Do you like this? Because you already had a lot of tunnel, 50% of your audience going, well, some people might not like this. Amplifying human stories, amplifying non curious stories.

it's such a gift that every time I see, a new booking, I'm like, oh, we are gonna have more chat. Are we gonna have more conversations? And actually, what can I learn from this? Because I never know where these conversations go. I didn't show you by the way that I show up with two blank pieces of paper.

I don't have prepared questions.

Debbie Millman: Wow. That's incredible. 

I,

yeah,I have 10 pages generally speaking. if I have less than 10 pages, I don't feel prepared. And I used to do it on [00:37:00] paper, but now I do it so that I can scroll up and down and go anywhere, wherever I want, wherever they take me. I have a place that I could go with something.

 Now, I also ask a lot of off script questions in that a lot of where we go is. not something that I have a specific question about already planned, but because I already know so much about them and they are talking about something that I have a sense of, I can then ask a more educated question and I really envy people that can just, and my wife is like that too.

She doesn't prepare. I mean, she reads and researches but doesn't prepare scripted questions. that would terrify me. That would just terrify me. I really have a lot of admiration in people that can do that on the spot. I find it to be remarkable, like magic.

Radim Malinic: I can tell you that potentially comes from DJing because I never had my DJs as planned. I would always start panicking 30 seconds like I'm gonna read the room. I'm gonna play this and start crumbling my record by going, oh, this is what I'm gonna do next.[00:38:00] 

Debbie Millman: yeah. But then that means you're really good with improvisation. and I think there, there's a difference between improvisation and acting. those one is scripted and you learn your lines. And the other is, has a sense of there being some collaboration and magic in the process.

Radim Malinic: Thank you. I mean, hopefully. is there anyone still left that you haven't interviewed that you would love to get on your podcast?

Debbie Millman: Oh my God. Is there a list lists and list and lists and list and lists.

Radim Malinic: What is the process of actually getting people like Ethan Hawke and some of the absolute mega stars of creativity onto the show, do you find is it difficult to get them on or is it actually that they're volunteering?

Debbie Millman: Well, it's not so much like Ethan just hit me up and slid into my dms and was like, babe, can I come on your podcast? That, that, it's his people. I, it's not Ethan. I just think that the show has, because it's been around for so long and. I have really been very lucky with a lot of the guests that I've gotten that I'm [00:39:00] probably on like some PR lists now, and so my, one of my more recent episodes with was with Suzanne Vega, who I'm, it was one of my heroes musical heroes, and I got an a note from her PR people.

I probably got that note because I got a different note from a different group of people that represented Ricky Lee Jones, another one of my. Musical heroes and so I look at those two kinds of interviews as like life symmetry. Like these are people that helped form me and now I get to share how they were formed with others.

Like to me, it's just incredible. But then there are times where I just reach out, I'll just send a note through their contact page. On their websites. and I get, I wrote Mike Mills, the film director, that way I remember sitting, it was years ago, it was Thanksgiving. And I was thinking about, what do, what am I thankful for and what would I like for this next year to be?

[00:40:00] And Mike Mills had come out with a movie that I love. And, I just wrote him, I just wrote him on the contact list and then he wrote me back, like directly and I was shocked. And then he was on the show. And then at the time he was, married to Miranda July. And our interview, she, he and I, our interview was wonderful, lovely.

We did it in person in Los Angeles. And then, couple of months later, I wrote him, I said, Hey, could you put in a good word for me with your wife? And he did. And then she came on the show. So it's really just. it's an interview, begets an interview. And so you get one artist and then you might get another artist and then suddenly you can have 10 artists.

And the same thing with designers and musicians. And the, probably the biggest surprise I ever had was when I was contacted by Thomas Kale's people. Thomas Kale, is the director of Hamilton. many ways, one of the co-creators of Hamilton and about. Five or six months after that, the play came out [00:41:00] after the Broadway show launched.

Radim Malinic: I got a note from his people and I thought it was a prank. I did.I mean, with podcasting and generally giving people space to express themselves, did you ever think where it would take you, 'cause I remember if I got it right, you were doing your, the initial podcast, I think on, I could throw a telephone line

and now we obviously a little bit more high tech than that, but I think beyond the technical advancements.

It's almost like it, it makes you grow more as a human and sometimes you don't really know when you begin on, when you start a journey where it takes you, what potentially would be the milestones and the enjoyment of that journey. Did you ever think what would happen next?

Debbie Millman: No, never. It was not something that I. Grew up aspiring to be 'cause there was no such thing. And even in those first a hundred episodes that I did on Voice America, they're terrible.really terrible interviews. I didn't know what I was doing. The other [00:42:00] part at that time, I started each episode with a monologue.

you're talking about how early podcasters wanna talk about themselves. That's what my early monologues were. They were musings of a 40 something wannabe. And when I ended up getting a real producer, which was because at the time, the late Great builder tell invited me to bring the show to Design Observer.

He was like, here's a little proviso though. You need to have better sound quality and you need a producer. And so he introduced me to Curtis Fox, who was doing something with the New Yorker at the time, and he's been my producer since 2009. He's given me a lot of notes and he's helped me grow quite a bit.

But that's when I abandoned the monologues and not because Curtis thought I should, but because I knew if I wanted to take this more seriously, if I was investing this kind of money into putting this podcast together, then I needed to focus on my guest and not me.

Radim Malinic: All of this makes me [00:43:00] think back to the class with Milton, your essay defining, writing what you potentially wanna achieve you achieve within 13 years. Is there another version of that essay? Is there something that express yourself in the next 10 years?

Debbie Millman: Well, the one thing that I didn't have on the list was love. And so in 2017, a lot of people had asked me prior, so I was on Tim Ferriss' show in 2017, his podcast, and we talked about the 10 year plan. And so then I got a lot of questions because I did the plan in 2005. People were like, oh, you're gonna write another one.

And it hadn't really occurred to me. And so I decided in that year that I'm gonna write another one and. I decided that I needed to have it done by, I wanted it done in 2017. So, when I wrote it, December 31st, 2017 and on, it was love. Like I wanted to fall madly in love. I meet my soulmate, and in October of 2018 I did, and [00:44:00] in 2020 we got married.

So you have it.

Radim Malinic: It always seems that your essays come to fruition already within a year that you

Debbie Millman: No, no, no, no. Notno. no. Not at all team. No, not at all. I mean, as I, the five year plan took really 13 years. 13 years. 13.

Radim Malinic: Well, I was only going to 2017 and the word love, and you

Debbie Millman: Well, that, that, you know,maybe, the ma magician that was helping me was looking at she's already 57. Let's get this started.

Radim Malinic: It's incredible, Debbie, with the voices that you hear in the industry and outside industry that this amazing minds. What is the general mood of creativity and where are we gonna go with, our industry 10 year plan, a five year plan, because. The fear as we talk a lot about fear, the arrival of AI has shaken up a lot of people potentially not, still looking for that confidence, haven't done that, those repetitions enough that they feel confident.

All of a sudden you've got tech coming in and shaking it all [00:45:00] up. And how do you see the fear, which is, automatic kind of dealing with all of it. And where do you see the state of conversation happening in the next five, 10 years?

Debbie Millman: The conversations about AI remind me a lot of the conversations that people were having in the eighties about. The computer in general, and prior to the eighties, designers worked on drafting tables and used exacto blades and wax machines and t blade, t squares. And there was a very hands-on approach to the work that was done.

A lot of craft. And when the computer, when Apple launched their max. A lot of really established designers at the time, the older states, people were vehemently opposed to them and declared that they would never use computers ever in [00:46:00] their work. And I can't even begin to tell you how many studios I visited over the last 40 years since seeing those very same people in front of a screen. Because we had, I think the big fear at the time was if you have a computer, it makes you a designer and it doesn't, and it didn't. And I've used enough AI now. To know that a good prompt doesn't result in soulful, original work, it can help you get ideas. It can help you do certain things faster.

It's great for research as long as you verify your sources. In some ways I think it's better than Google in that regard. Now you can get a lot more information just by asking a question as opposed to having to go through pages and pages of sources. but again, you have to check the attribution. I think that AI is going to fundamentally transform science, math, medicine, and [00:47:00] that's incredible. Large language models, large models, that man that can manage numbers, that will transform a lot of the way that we live. Any creative endeavor, any original creative endeavor starts in our brains, which AI has yet to master and.

They might come up with options, but they're not gonna come up with original ideas. AI is good at combinatorial, creativity, not originality.

Radim Malinic: You, you said the S word soul, 

and I always think about it when people worry about certain clients, replacing creative teams with AI replacing, copywriters with ai and you're thinking. You will always find people who want to have work with soul for their audience, for their customers, like for, for what they're creating.

Because ultimately there will be people always taking shortcuts and there will be always people who actually will double down on humanity. And as you said, or not creativity that comes from within [00:48:00] because there will,I would love to believe that there always will be demand for work like that.

Debbie Millman: Yes. 

Radim Malinic: I think the realization that even though I've been publishing books for 10 years and been in the creative industry for 25 years, it is the generosity that changes everything because ultimately. it brings me to one last quote of this since we all about quotes today, and that's from Chris Cornell 

and Chris Cornell.

Once upon a time an interview with Jules Holland on BBC once said, look, if I was the best musician I could ever be, but be into music as much as I can be, practice enough and be into music enough, then the best band in the world will come and beg me to play for them. Except that never happened.

Therefore, we had to create our own dream band, and that was Sound Garden. And this is the guiding line, which I feel, when we talked about courage and confidence and self-acceptance is ultimately what you put out there. What you create for yourself will always be yours. You can always drive a destiny.

You can always drive your soul into the place [00:49:00] that makes you happy, that makes you content, and makes you satisfy. Creatively, can actually open so many possibilities because I never really thought that, Kind of reversing the process and saying, look, I'm gonna start a place where I wanna see other people rather than I wanna be elsewhere.

Because I'm sure that, you send some of the pitches to people, but you must have in your inbox full of, whatever PR companies go in, Hey, there's a dentist supposed to be on your show and there's a, a lawyer. have you never listened to this show?

Debbie Millman: Well, that, that's true. I do get a lot. I get a lot like. Many, many, many, every day from people that think that because it's called design matters, that somehow it has something to do with, Constructing pools or windows. And in as much as I love a good pool and I love a good window, it's not, it's, that's not my bag.

And so I always find it really interesting, again, getting on these lists of PR people that, are just trying to do their job. Nothing against it at all, other than I've never interviewed a pool [00:50:00] person and I probably never will.

Radim Malinic: What about a window? 

Debbie Millman: It depends than if I got free windows. Teasing. No, probably not.

Radim Malinic: Debbie,we haven't covered so many topics that we should have done, but let me just talk quickly, ask you about books because your books are phenomenal. Your last book was really inspiring and just sort of changing the topic, and I'll talk about something which is, again, close to our souls process of making books.

And again, this feels like a question for another whole podcast, but 

Debbie Millman: I'm happy to do a part two if you want to. This has

been so much fun and 

Radim Malinic: then we'll. 

Debbie Millman: love having great conversations.

Radim Malinic: So I think we need, we'll need to book a, a number two 

because I have to thank you because what you've created for yourself. you didn't wait for the best podcast in the world to come and beg you to interview for them because that didn't really exist at that time.

Now you've created all of these things that. Where your light was, was guiding you. You created this and, having people like DNE and others, having these amazing stories about what we do. I think we believe [00:51:00] in, how about we long be gone? This in this world, I think we believe in the breadcrumbs full of soul, full of heart, full of love that, people can follow and ultimately create work that, it's just fascinating and amazing that we potentially would not have 

Debbie Millman: Yeah. Yeah. I mean, a lot of what I've created was because I wasn't. Readily accepted or invited into the best band in the world, or the best firm in the world, or the best anything in the world. And so I kind of had to make my own way, and that was fraught at times and still is. But I'm glad I did it that way, this way 

Radim Malinic: Fantastic. Debbie, thank you very much for part one, and I'll take you, I'll take you up on your words and we'll, we'll definitely speak very soon because I wanna know more and 

Debbie Millman: Okay, 

Radim Malinic: we're just only scratching the surface. So thank you so much for today. Thank

you. 

Debbie Millman: my absolute pleasure. It has been truly, an honor and a delight.

Radim Malinic: Thank you.

 [00:52:00] 

Thank you for listening to this episode of Daring Creativity Podcast I'd love to know your thoughts questions and suggestions So please get in touch via the email in the show notes or social channels This episode was produced and presented by me Rad Malid The audio production was done by Neil Mackay from 7 million Bucks Podcast Thank you and I hope to see you on the next episode