The Tim Ferriss Show - #230: The Secrets, Tactics, and Creative Processes of High Performers and Achievers -- Debbie Millman

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Starting point is 00:02:43 Friday subscribers. So check it out. Tim.blog forward slash Friday. If you listen to this podcast, it's very likely that you'd dig it a lot and you can, of course, easily subscribe any time. So easy peasy. Again, that's tim.blog forward slash Friday. And thanks for checking it out. If the spirit moves you. Hello, boys and girls, this is Tim Ferriss, and welcome to another episode of The Tim Ferriss Show. I'm looking into a camera to record this as a behind the scenes, and it's a little too weird, so I'm going to look away and divert my eyes. Nonetheless, The Tim Ferriss Show is always about deconstructing world-class performers, teasing out the habits, routines,

Starting point is 00:03:23 favorite books, et cetera, that you can apply to your own life and test immediately. Whether those experts are coming from the worlds of chess or entertainment or sports business or otherwise, it is my job to dig into the details. This episode is a little bit different, but I'm very, very excited about it. This is Debbie Millman round two. Now, when Debbie first came on the podcast, I immediately knew when I hit stop on my recorder that it was something special. What I didn't expect necessarily was that her interview would very quickly become one of the most downloaded episodes of all time. That's out of more than 200 episodes, just shot way, way up there. I think it's past 2 million downloads

Starting point is 00:04:05 now. Debbie, at Debbie Millman on the socials, has been called one of the most influential designers working today. She's the founder and host of Design Matters, the world's first and longest running podcast about design, where she's interviewed nearly 300 design luminaries, including Massimo Vignelli and Milton Glaser. Milton Glaser has a fascinating story in terms of his 10-year exercise that he did with Debbie. And she talks about that in the first episode. Debbie herself has done it all. Her artwork has been exhibited around the world. She's designed everything from wrapping paper, wrapping paper, just since I flubbed that one, to beach towels, greeting cards, to playing cards,

Starting point is 00:04:40 notebooks to t-shirts, and Star Wars merchandise to global Burger King rebrands. She's a best-selling author and has really tried her hand at just about every aspect of design, and her story is incredible. In this round two, Debbie answers all of the questions that you guys were dying to ask her. These are your most popular. So you submitted questions and upvoted them. Topics include how to turn down stability for opportunity, because she came from a very conservative background, was very risk averse. How did she make the leap? How does she continue

Starting point is 00:05:10 to try new things? How to outsmart the competition in any job? The future of graphic design, her own personal creative process, and the most valuable lessons she's learned about life design. So designing an ideal life for herself, which she came to pretty late. So there's still hope for those of you out there thinking, ah, it's something you have to do in your twenties or while you're in college. No, not true. And she covers much, much more. So thank you so much for submitting and uploading all of your questions. And I hope you enjoy this episode as much as I did. Without further ado, as I always say, here is Debbie Millman, round two. Hi, this is Debbie Millman, and I am coming to you from the Tim Ferriss Show,

Starting point is 00:05:54 where we are conducting part two of my interview. And in this episode, I'm going to be answering listeners' questions. These were questions that were sent to Tim that he forwarded to me. So the first two questions come from Katja Mars. In the first question, she asks, for the exercise where you write out what your life looks like in 10 years, what if you see multiple potential lives and don't know which one will be better for you. What do you do? Katja, my recommendation is to write them all down. I had and still have multiple potential lives which all are being lived at the same time. I don't believe that any one person only has one specific calling. I think you can have lots of different things

Starting point is 00:06:46 that you do at lots of different times in your life. The remarkable thing about my life plan that I did after Milton Glaser's class was that not only did I write down my essay, but I also wrote down a list of the things that I hoped in my best possible life I could accomplish. And they were all from different parts of my life. And as the years have passed, and it's now 12 years since I did that original exercise, year after year, more and more of them seem to be coming true almost magically. Now, it might be because I declared them back then. It might be because I've been consciously or subconsciously working toward those goals.

Starting point is 00:07:24 But I believe that if it's something that you really want in your heart and you put it out there, you have the potential no matter what walk of life it is in that you can accomplish them. Kachemar's second question is as follows. You made the hard decision to turn down the role of CEO and do your own thing, and it worked out well. But by then, you were already established in your career with major brands and bragging rights in your portfolio. What if you had done this at age 30 or 32 or 27? What if you did this before you even worked at a top agency? What advice would you have for someone contemplating turning down the stability of a comfortable known, of a guaranteed way to establish themselves and build up a savings first for an unknown to pursue their curiosities right now rather than wait for the right time? So Katja, what I'm going to say right off the bat is that there is no right time. I think that we humans delude ourselves by thinking that there is a possible

Starting point is 00:08:27 right time, that there's a possible right time to quit a job or the possible right time to have a child or the possible right time to get married. And I think that because of the way our brains are constructed, we delude ourselves with this. Our brains are actually what are called the triune brain. It's a brain that is three in one, tri-une. And the three parts of our brain are the neocortex, the limbic brain or the mammalian brain, and the reptilian brain or what Seth Godin calls the lizard brain. And the neocortex is the part of the brain that controls much of our modern thinking, our ability to have abstract thought, language. These are the parts of the brain that marketers love so much. The limbic brain or the mammalian brain is a part of the brain that all mammals share.

Starting point is 00:09:17 Mammals rear their offspring live. We don't hatch eggs. We very much tend to care for our offspring. We have deep feelings of connectivity and love for others that is all coming from the mammalian brain and then the reptilian brain the oldest part of the brain which sits right on top of the spinal cord that is the part of the brain that controls all of our involuntary activity so our our digestion, our eye blinking, our heart beating. It also controls things like our adrenaline. So if you were to walk across the street and nearly get hit by a car,

Starting point is 00:09:52 you couldn't think at that moment, adrenaline, kick in, keep me safe. That is something that happens involuntarily. And the reason I'm telling you all of this is because when we are living with our reptilian brain, which we all do, that part of the brain hates uncertainty. That is the oldest part of the brain that kept us safe, that wants to keep us secure. That is the part of the brain that is the deepest, most hardwired part of who we are. And that part of the brain doesn't like uncertainty. It doesn't like instability. It doesn't like being vulnerable. And all of those things that you're asking about doing are all things that have an uncertain answer that make us feel insecure, that makes us feel vulnerable. So you can never will in the same way that you can't will that adrenaline. You can never

Starting point is 00:10:42 will your reptilian brain to be, woohoo, change, insecurity, instability, vulnerability, bring it on. We're going to have tendencies to want to retreat from those feelings. And so one of the things that I learned from doing Design Matters from my guest, Danny Shapiro, was that confidence. And I think I mentioned this in part one of my interview with Tim. Confidence is overrated. Danny Shapiro has said that what is more important than confidence is courage. I believe that confidence is developed over time after repetitive success at any specific endeavor. The more you do it, the more successful you are, the more confidence you have that the next time you do it, you will be as or more successful. What is more important is courage because you have to take that first step without

Starting point is 00:11:29 any guarantee of safety or security. You have to put yourself in a vulnerable position and then just take that step. So you asked what I would have done at age 30 or 32 or 27. The fact of the matter is I didn't have the courage or the confidence to do any of the things that I'm doing now at 30 or 32 or 27. I was tremendously afraid that I was not smart enough or pretty enough or talented enough or connected enough or rich enough to do any of the things that I really wanted to do that probably required none of those things. I think it just requires a belief that it's possible, which I didn't have. So if you want to do it now, my suggestion is

Starting point is 00:12:11 do it now. If you're afraid to do it now, try to live in a moment of courage for one moment and take that first step. No amount of money, no amount of security is ever going to give you the sense that this is the right time because it's uncertain. That first step is uncertain. Do you want it badly enough to be able to risk that or not? And that's the question that you have to ask yourself. Jimmy Sciotta asked two questions as well. He asks, it was already hard getting paid before. So now with all these services online, competition-based work and price dropping, etc., it seems like the graphic design market is losing a lot of value. Au contraire, Jimmy. I disagree. I think the graphic design is more important than ever. What is happening, though, is because it's more important than ever, we see a lot of people entering the market that are willing to give it away for less money.

Starting point is 00:13:05 But you do get what you pay for. And any service that's offering a product that we do for less money is going to provide less value. Initially, I was really, really worried about all the services that are selling logos for $5 and doing bidding and giving the project to the lowest bidder. And what I found is that you really do get what you pay for. Anybody that is going to those services to get creative work is likely not going to get the benefit of sound strategic thinking, which makes all the difference in great graphic design. I believe that graphic design and branding,

Starting point is 00:13:40 the culture or the condition of graphic design and branding reflect the condition of our culture. And you're not going to be able to get that kind of work from a service that offers that kind of work for $5. So I don't think you have to worry about that. Think about how do you provide added value? How do you provide the benefit of what you do best to your clients? Can you identify what that benefit is? If all you're offering is good design, that's kind of a commodity. What else can you offer? Can you talk about how your design is going to make a difference? People are not looking for a difference in flavor or a difference

Starting point is 00:14:18 in form. They're looking for how is this going to make a difference in my life? Can you prove what your work can do to provide that? Jimmy's other question is, where do I see a future for a graphic designer? And my answer is, the future is whatever you make it, whether you're a policeman, a fireman, a doctor, a neurosurgeon, a podcaster, you create the future that you want to create. It is not specific to any discipline. Ricardo Magalhaes also has two questions. He asks, the pace in the industry is overwhelming and impossibly hard to keep up with. The feeling that someone will do better than me, why bother, is a constant. What are the right questions to ask oneself, actions to take, to prevent the act of creation from being so paralyzing? Ricardo, I think you would benefit from considering what is the purpose of doing what you do?

Starting point is 00:15:15 Is the purpose of doing what you do for fame, for money, for some sort of accolade, or is it for the sheer joy of doing what it is that you're doing? If you are constantly comparing yourselves to others and asking yourself, why bother? Then you have to ask yourself, why am I comparing? What am I worried about? Why do I need to compare? I would also suggest that you listen to the very beginning of my episode of Design Matters with Sue Matthews Hale. Sue Matthews Hale was somebody that I was asking those questions about as well. On my podcast, I like to talk about the trajectory of a life and how people overcome obstacles. And as I was researching her life, I saw this incredibly beautiful, well-dressed, gorgeous woman who seemed to have it all. A great marriage, a great child, a great career.

Starting point is 00:16:07 She had worked at Pentagram. She was a partner at Lippincott. The only thing I couldn't find was where she had grown up and what were her origins. And I did something that I rarely do. I actually wrote her and said, hey, Sue, I can't find this information. Where were you born? Where did you grow up? When she wrote me back, the answer

Starting point is 00:16:25 stunned me. She wrote me back and said, I was abandoned on the street when I was two years old in Korea. I was left on the street. I was picked up and brought to an orphanage where I was found by my parents. You never know what somebody's life is like. The arc of a life is a circuitous one. At any moment, something wonderful or something terrible could be happening that we don't know. Concentrate on your own life and doing what you want from your own heart. Try not to compete with others. It's hard enough doing what you want, let alone comparing what other people have or what you perceive they have. And I know that that sounds kind of tough, but I think that thinking about what we want is hard enough.

Starting point is 00:17:04 Thinking about what somebody else wants or doesn't want or does or doesn't do, you have no idea what their interior life is like or what demons they're battling. Your second question is, what questions do you ask yourself to overcome the so dreaded imposter syndrome when planning to do some kind of work. Well, that implies that I've overcome the dreaded imposter syndrome. And I haven't. I deal with it all the time. And the question for me is, at my age, if I don't do it now, when am I going to do it? If not now, when?

Starting point is 00:17:37 And so the question becomes, do I want to do this badly enough? Or do I want to give in to the notion that I don't deserve doing it? And at this point in my life, I have to say, if I want it badly enough, I have to do it. I can't wait anymore. Daniel Carbone asks, how did you come to the shift in your lead gene? You mentioned that your lead gene had once been living in Manhattan, but I'm curious how and when that shift occurred. Well, Daniel, it wasn't a shift so much as a major

Starting point is 00:18:06 realization. I had been telling myself for decades that I had compromised on the intersection of 6th Avenue and Bleecker Street in Manhattan that summer of the police's synchronicity and David Bowie's modern love. And what I came to realize all these years later, we're talking 30 years later before I had the realization, was I only compromised in that. I didn't compromise in the one most important thing, which was to live in Manhattan. And I did whatever it took. I lived in this awful, deplorable, tenement walk-up. I lived having to walk through somebody else's bedroom to get to mine. I lived having to sleep on the floor one night because they were busy doing what couples do in the room that was preventing me from getting to mine. I didn't realize that until years later. I could have lived anywhere. I could have lived with my

Starting point is 00:18:55 mother. I could have lived back then living in Brooklyn or Queens was really, really inexpensive. I decided that I needed to live in the most expensive city in the world because I wanted to be in the most exciting city in the world. And so I did whatever it took to be able to do that. At that moment in time, living as an artist would not have allowed me to do that. And so I made that compromise in the face of making a decision about what that lead gene was. I just didn't realize that for 30 years. It took me a long time to say, hey, wait a minute. I've been lying to myself all this time. I did do what I wanted to do. I did that because I wanted that more than anything else. And so one of the things that I talk about is what is that non-negotiable for you? What is that one thing that you want more than anything that you're willing to sacrifice everything else to get. And that's the decision that I made at that time. Mike Prendergast asks, you've been so influential on so many properties from Star Wars to Orange Juice. I'd love to know more about your approach.

Starting point is 00:19:56 What does your creative process look like? Mike, my creative process is really messy. I don't really have a process. I don't know that there really is such thing as a process, a cookie cutter way of approaching anything. In terms of my approach, I think that I start out with a desire to make something, whether it be a package design, whether it be a podcast, whether it be a lesson plan, whether it be a piece of art. And I have this vision for what that is. Sometimes that vision happens really fast, and it comes when I've been marinating and germinating and thinking and thinking and thinking. And sometimes it comes really slow after doing exactly those same things and feeling really helpless that I'm never going to be able to come up with an idea.

Starting point is 00:20:40 The one thing that I can suggest is if you are stuck, take a walk. Walking really helps me generate ideas. The more I walk, the more ideas I have. So in terms of approach, think about what you want. Think about what it is you want to make. Think about the end game. What does the vision of that look like? And then either start doodling, start drawing, start making, start sketching, start pulling your hair out, whatever it takes to get that process started. And then keep going until you feel like you have something worthwhile. That might take an hour. That might take a day. That might take a year.

Starting point is 00:21:16 That might take a lifetime. But I think if you enjoy the process of making, the fact that you don't have a result makes it somewhat easier. But I say somewhat because I think the whole idea of making anything in the first place takes a great deal of courage. Good luck with that. Aspen Janae Mulcahy asks, do you do any other exercises with your students like the 10-year goal writing exercise? And if not, could you speak to your time as a teacher and what I've learned in helping others with life design? Aspen, I spend a lot of time with my students helping them understand how they come across. And this stems from the notion of how do you want to be perceived? And one of the other exercises that I ask my students to undertake is to think about how they come across, think about what that first perception is.

Starting point is 00:22:09 And I ask them to write two paragraphs. The first is what they believe their first impression is, how they show up and what people perceive about them. The second is about what they want their first impression to be. This culminates in their writing a statement about what they project today and what they project tomorrow. So for example, I might write, today I am shy and recessive, tomorrow I will be more curious and engaging. I call this the intentional first impression.

Starting point is 00:22:41 We should be able to determine how we come across in a much more ownable and decisive way. Don't leave it should be able to determine how we come across in a much more ownable and decisive way. Don't leave it up to others to determine who you are or how you show up. And if you think about how you do this, if you actually create a conscious plan to be you on your best day when you show up, then you'll be able to show up that way. It's not about manipulation. It's about intention. I also ask my students to determine the three-word combination that could only describe them. And this should be an accurate and deep expression of who you are. The three words should be reflective of your full self, not just your best self. So the word should be cognizant of your strengths

Starting point is 00:23:25 as well as what you might perceive as your weaknesses. But I find that your perceived weaknesses actually give us an opportunity to peer into a part of yourself, ourselves, that is really meaningful if we dig deep enough. For example, I had a student that identified that one of her words of the three was know-it-all. And I asked her to deconstruct why she was like that. And she identified that she came across as a know-it-all because she was really insecure about being smart. And she wanted to be perceived as smart. And what that meant was if she needed to be perceived as smart and didn't just accept the fact that she was smart, that she harbored a suspicion that she wasn't smart. She wasn't

Starting point is 00:24:11 smart enough. She wasn't as smart as the other people around her. So by coming across as a know it all, she was compensating for this deep seated fear that she wasn't smart enough. And just knowing that, just facing that feeling that she didn't smart enough. And just knowing that, just facing that feeling that she didn't feel smart enough allowed her to really understand whether or not that was valid. And she wasn't coming then out of a place of aggression or manipulation. She was understanding that her need to do that was really trying to cover up a feeling that may or may not be accurate. And if it wasn't accurate, why did she need to be doing that? If it was accurate, what did she need to be doing that would allow her to feel or be smarter?

Starting point is 00:24:51 And improving that would help her stop actually having to compensate for something that may or may not be accurate. So think about what those three words can be. There should be some tension in those three words. Ultimately, that unique combination, if you really do this successfully, should be something that only, only could be used to describe you. But part of that is being able to identify some of the things that you're afraid of others knowing about. So spend some time with this exercise. First, spend some time thinking about what your intentional first impression is, and then spend some time thinking about what are the three words that only could be used to describe you, taking into account that some of what you perceive to be weaknesses are areas that are available to you to consider more honestly and become stronger around.

Starting point is 00:25:47 Kelsey Hellman asks, Debbie, how much of your time is spent teaching college courses? How do you fit this into your already busy career? I've always been fascinated by people who incorporate teaching with their job and would love to hear more. Kelsey, my first opportunity teaching came as an undergraduate teacher at the School of Visual Arts where the chair of Bleeker Street and 6th Avenue in 1983. How could I work with students to prevent them from starting to curtail the possibilities of their life before they were even possible? How could I work with students to help them, to keep them from editing what was possible in their lives based on their own internal fears that might not

Starting point is 00:26:47 be accurate. And so that became my first class. And I was teaching students ostensibly how to get a job. The actual class is called differentiate or die, how to get a job when you graduate. But really what I was trying to help teach them was how to believe in what is possible for your future and go after it. So it's not about just getting a job. It's about how do I fulfill my calling? How do I get the dream job? How do I live as if my life depends on my doing what is in my heart? And how do I make that heart sing? And so that has been the basis of my undergraduate teaching now for the last decade. I started my graduate program in 2009 when Steve Heller asked me if I'd be interested in co-founding this program with him, which would be the first program of its type in the world. And

Starting point is 00:27:37 I jumped at the chance. I love teaching. I feel like it's the most important thing that I do. What I try to do with my students is instill in them a sense of possibility, a sense of what is possible in their lives, both in terms of their calling as well as my firm belief that branding is not just a career about a return on an investment of advertising and marketing and positioning. It is a profound manifestation of the human experience and that we are now using branding way more than just being able to delineate one product from another. We're using branding to help develop movements and causes. Think about Black Lives Matter. Think about the pink pussy hat. All of these things, humans are using the very tenets of branding to create social

Starting point is 00:28:33 movements and social change. And that's why I do what I do. Nicole Haynes asks, how do you ensure a healthy balance between work and play? Nicole, this is where I might have to reveal that I think that all of my work is play at this point. I have wanted what I'm doing in my life for so long. For so long, I've been longing for all of these opportunities, that now it doesn't feel like work. It feels like this tremendous gift that I was given. I didn't really start doing the things that I love with all of my heart, my podcast, my teaching, until I was well into my 40s. And so now that I have these opportunities to do these things, I'm just incredibly grateful to have these opportunities.

Starting point is 00:29:18 And I don't see them as laborious. I just see them as joy. But I also caution my students when they tell me that, oh, I can't do that. I'm too busy. I tell them, hey, busy is a decision. We decide what we want to do based on what we think are the priorities in our lives. And if we don't get to them, I suggest you look at how important they are to you. How important are they? Is it more important

Starting point is 00:29:46 to watch Game of Thrones or write an essay or paint a painting or make a podcast? And if those things are more important, you're never going to get to the painting or the essay or the podcast. And so we decide the things that we want to do. And if you feel like you're using busy as an excuse to getting to do them, then they're just not that important to you. Nicole also asks, what do you think sets people like you, Tim, and many other high-profile achievers apart from those who just coast through life without ever really feeling impassioned by their work? Well, Nicole, I can't speak for Tim, and I can't speak for any of the other high-profile achievers you're talking about. What I can tell you is that for me, I have profound insecurities

Starting point is 00:30:32 and I use my work to create meaning for my life. I think that people that coast through life without ever really feeling impassioned by their work, might just have had really good parenting and don't feel the need to make a name for themselves by their work because they feel just intrinsically good about who they are. So if you aren't feeling impassioned by your work and just feel impassioned by life, bravo. Congratulations. You have something that very few of us actually have. Lior Shank asks, to what extent do you get creative blocks? Malcolm Gladwell mentioned that being in a large-scale newsroom with tight deadlines eliminated his writer's blocks simply because there was no room for such luxury. I wonder if you ever experienced similar

Starting point is 00:31:17 effects. How do you stay so prolific? Lior, I work under tremendous deadlines as well. And I find that if you want something to get done, give it to a busy person to do. If they want to do it, they'll get it done. And so because of the deadlines, because of the constant pressure for a new podcast or a new lesson plan, which I can't really control, I feel that I have to operate under this intense need to get it done. I do experience block mostly from ideas. So for example, if I have to write an essay or if I have to create a piece of art, there are times where I don't feel impassioned, where I don't feel the muse. And that's worrying because that does create delays. I find the best way to get over that block is sleep. I feel more creative obstacles if I haven't gotten enough sleep.

Starting point is 00:32:11 And sleep regenerates your brain, it regenerates your cells. And I find that if you're in a regenerative state, you're much more likely to be creative. Emily E. Godwin asks, who are some of your favorite visual artists? Well, Emily, Jean-Michel Basquiat is a perennial favorite. I also just met Deborah Cass, and I'm smitten with all of her work. Kathleen Dillon asks, has Debbie found common threads, if any, in her interviews of creatives as to how they have designed their lives, and if so, what are they? Kathleen, what I have recognized is that almost everybody that I've ever interviewed, with the exception of two people, still face debilitating self-loathing and also are tremendously insecure about what they do. I think that people view high achievers simply as high achievers and that they don't experience tremendous self-doubt. And almost everybody that I've interviewed,

Starting point is 00:33:11 whether they talk about it on the air or not, even in my research, I've found that they question what they do, how they do it, why they do it. The only two people that I've ever interviewed that seemed to be really secure about what they were doing in this world in their creative life were Milton Glaser and Massimo Vignelli. And at the time, the common denominator that they shared is that they were both in their 80s when they told me this. So I kind of feel like by the time you get into your 80s, it's like, hey, fuck it. I am who I am. I do what I do. World be damned. And I think that's wonderful. By the time you're 80, I think you should earn that. And so for all of us out there

Starting point is 00:33:51 that are feeling self-doubt or are worrying about the value or the purpose that we have in our lives, know that I think every single creative person battles that too. Tony Fram asks, in your view, what are the qualities of a good design student? Tony, curiosity, wanting to learn, being excited by learning, always wanting to learn and know new things. Those are the most important qualities of being a good design student. So now I'm going to answer some additional questions from Tim Ferriss himself. Tim sent me a whole slew of questions, and I'm going to answer Milton Glaser. As I've just said, there's something about Milton where he is just fully engaged with life. And he's been fully engaged with his creative life for his entire life. And he's made so much impact.

Starting point is 00:34:54 He's created the most profound logos, magazines, movements, and of course the I Heart New York logo, which if there's any logo on this planet I wish that I could have done based on my love of New York and my love of design, it would be that logo. So Milton Glaser. Another question from Tim. What is something you believe that other people think is insane? Well, I am a conspiracy theorist. Most of the close people in my life think that I am insane for some of the conspiracy theories I believe in. I'm not going to go into detail here because I'm so worried that everybody in the world listening to this will think I am insane. But if there is a conspiracy theory out there, chances are I believe it. What is my favorite documentary or movie? My favorite movie is Manhattan by Woody Allen. I love that movie. I know that movie by heart. I also really, really love the movies

Starting point is 00:35:57 Fast Times at Richmond High and Elf, mostly because I don't stop laughing all through Elf, and I think that Jeff Spicoli is one of the great characters in all of cinematic history. Tim asks, what are your morning rituals? What do the first 60 minutes of your day look like? Well, at this point in my life, the first 60 minutes of my day are mostly about trying to get my dogs out fast enough so they don't pee on the bed or the floor. And I would say that only half of the time I am successful. My first 60 minutes are a mad rush to

Starting point is 00:36:32 get outside to make sure that they can relieve themselves without losing any of their dignity. I also try to have coffee at the same time. What obsessions do you explore on the evenings or weekends? I am obsessed with sleep. I love sleep. I love having a comfortable bed and beautiful blankets and great pillows. And so I am obsessed with the notion of what can be regenerating while I am in slumber. What is the best or most worthwhile investment you've ever made? Could be an investment of time, money, energy, or other resource. How do you decide to make the investment? I am the kind of person that only likes to do things that I feel comfortable doing. It's very, very hard for me to do new things that I feel awkward doing. So when I tend to like to do

Starting point is 00:37:24 something, I tend to do it as often as possible. And I think that persistence and that resilience is something that pays off in the long term by doing something over and over again for as long as possible. But I think that my best investment was probably buying my co-op in 1993 in a neighborhood that was at that time in New York City considered a crack neighborhood,

Starting point is 00:37:46 which then became the Highline neighborhood. So I think that quite by accident, that became the best investment that I've ever made. Do I have a quote that you live your life by or think of often? I have a few, but I think my most heartfelt is everything worthwhile takes a long time. And that has been a mantra for my life. I also really love a line from James Joyce's Ulysses, which is the longest way round is the shortest way home, which I think is just a more poetic way of saying everything worthwhile takes a long time. And maybe I just tell myself that because most of the things in my life have taken a long time and it's a just tell myself that because most of the things in my life have taken a long time and it's a way for me to self-soothe. But I really do believe that

Starting point is 00:38:30 the longer that something takes, the longer it lasts and the less pressure you have to sustain it for the rest of your life. If you could have one gigantic billboard anywhere with anything on it, what would it say? I love this question. It's something that I sort of have in my office. It's not a large billboard, but it's a chalkboard with one word on it. And it's high up on the window where I hope everybody can see it when they walk in. And it says, yes. Try to say yes to almost everything or say yes, but or yes, and. Some of the most important things that I've been offered in my life were opportunities that didn't quite seem exactly right. But when I was able to say yes, but how about if we do it a little bit differently? Or how about if we do it slightly more like this, those were things that really did benefit from the open-mindedness of both myself

Starting point is 00:39:28 and the other person that was offering the opportunity. Look at opportunities as options in that you can take those opportunities and make them more about what you want or what you can do or what you can create. And so think more from an opportunity of how can I generate more from this as opposed to how can I drain this away? This will be my last question. What advice would you give to your 20, 25, or 30-year-old self? And please place where you were at the time

Starting point is 00:40:00 and what you were doing. I'm going to say just anywhere between 20 and 30, because I have often said that that decade was 10 years in experiments, in rejection and failure. What I would tell myself is stop worrying so much. I would tell myself that every dream that I've ever had about who I could be would be possible if I wanted it badly enough. And if I wanted it badly enough, work as if my whole life depended on it, because it did. It would be. It has. And so I would still, even though it would hurt like hell, go through, want to go through every single thing that I've gone through. Because if I hadn't, I wouldn't be right here right now.

Starting point is 00:40:54 The arc of a life is really circuitous and you never know where you're going to end up. But what I can say is that despite all the pain and the hardship and the abuse, where I've ended up right now is exactly where I want to be. And so even with those moments of despair that I experienced, even what seemed like the worst moments of my life, those turned out to be the most important, the most impactful, the most necessary. And therefore, I wouldn't change anything. I hope you enjoyed part two of this episode on The Tim Ferriss Show. It has been a true honor to be on Tim's show. And I want to thank both Tim Ferriss and all of his wonderful, generous listeners. Thank you. Hey guys, this is Tim again. Just a few more things before you take off.

Starting point is 00:41:47 Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out.

Starting point is 00:42:31 Just go to 4hourworkweek.com. That's 4hourworkweek.com all spelled out and just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it. This episode is brought to you by Wealthfront. Wealthfront is the future of financial advice. They've become incredibly popular among my friends in Silicon Valley and across the country because they provide the same high end financial advice that the best private wealth managers deliver to the ultra wealthy, but for any account size and at a fraction of the cost. For instance, they monitor your portfolio every day across more than a dozen asset classes to look for opportunities to rebalance or harvest tax losses. Now,

Starting point is 00:43:10 would you do the same? Are you doing the same? Probably not. And the power is in the software. Wealthfront now manages more than $4 billion in assets, which is up from around $2.5 billion when they started advertising on this podcast. They're growing incredibly quickly. Unlike old-fashioned private wealth managers, Wealthfront is powered by innovative technology, making it the most tax-efficient, low-cost, hassle-free way to invest. They don't have bloated sales teams or retail locations, so they can deliver all of this sophisticated financial advice and these services at a fraction of the cost of a traditional financial advisor. So at the very least, go to wealthfront.com forward slash Tim and take their free risk assessment survey. It only takes a couple of minutes and Wealthfront

Starting point is 00:43:54 will recommend a personalized portfolio of investments. In other words, they'll tell you exactly where they would put your money. So even if you don't use their service, you have a huge leg up and you have additional information for making good decisions. They use investment theory to automate good financial behavior and decisions that people typically don't make but should. So go to Wealthfront.com forward slash Tim to get your first 15K managed for free or just to get more details. Check it out. Wealthfront.com forward slash Tim. This episode is brought to you by 99designs. I've used 99designs for years for all sorts of graphic design needs.

Starting point is 00:44:29 Whether you need a logo, website, book cover, or anything else, 99designs was created to make great designs accessible to everyone and to make the process of getting designs much, much easier. So when I first started out, for instance, testing prototype covers and getting prototype covers for the four-hour body, I want the contest route. That is one option. This is a great solution if you're looking for fast, affordable design work and the ability to choose from dozens of options risk-free. Let's say you need something late night, quick turnaround. Well, people in other time zones,

Starting point is 00:44:59 other countries can also help you solve that problem. Since then, I've worked with 99designs on a separate path or a different option. And that is the one-to-one project service. So in a number of cases, and I'll give you one example, when I wanted to create the cover for my audio book, The Tao of Seneca, this was a very important project to me. I decided to use their one-to-one project service. And with this service, you can invite a specific designer to your project, agree on a price, and then work together until you're satisfied and they allow you to iterate and provide feedback and all this stuff and I haven't shared it yet but we also got some incredibly good really some of the best illustrations I've ever seen from using this one-to-one project service with a handful of different designers and illustrators.

Starting point is 00:45:45 It blew my mind. 99designs makes this all very easy and efficient. So you can check out the Tao of Seneca design and other work that I and your fellow listeners, for that matter, have done on 99designs at 99designs.com forward slash Tim. And right now you can get a free $99 upgrade on your first design. Again, that's 99designs.com forward slash Tim. And right now you can get a free $99 upgrade on your first design. Again, that's 99designs.com forward slash Tim.

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The Tim Ferriss Show - #230: The Secrets, Tactics, and Creative Processes of High Performers and Achievers -- Debbie Millman

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The Tim Ferriss Show - #230: The Secrets, Tactics, and Creative Processes of High Performers and Achievers -- Debbie Millman

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.