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Tim @ 5:15

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Hello, boys and girls. This is Tim Ferriss and welcome to another episode of the Tim Ferriss Show. I’m looking out 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, favorite books etc, that you can apply to your life and test immediately, whether those experts are coming from the world 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 2. 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 two-hundred episodes. It just shot way, way up there. I think it’s past two million downloads now. Debbie, @DebbieMillman on the socials, has been called one of the most influential designers working today. She is the founder and host of Design Matters– the world’s first and longest running podcast about design, where she’s interviewed nearly three hundred design luminaries, including Massimo Vignelli and Milton Glaser. Milton Glaser has a fascinating story in terms of his ten-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… right, right, wrapping paper– since I flubbed that one– to beach towels, greeting cards to playing cards, 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 2, Debbie answers all 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 very conservative background and was very risk averse; how did she make the leap; how does she continue 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 is something that 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 upvoting 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 2.

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Debbie @ 7:59

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Hi. This is Debbie Millman and I am coming to you from the Tim Ferriss show, 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 Katcha Mars….

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Katcha Mars @ 8:25

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For the exercise where you write out what your life looks like in ten years, what if you see multiple potential lives and don’t know which one will be better for you? What do you do?

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Debbie @ 8:36

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Gotcha. 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 could have lots of different things 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. They were all from different parts of my life. And as the years have passed– and it’s now twelve 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, 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.

Katcha Mars second question is as follows…

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Katcha Mars @ 9:48

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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 thirty or thirty-two or twenty-seven? What if he 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 the savings first for an unknown to pursue their curiosities right now, rather than wait for the right time?

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Debbie @ 10:27

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So, Katcha, 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 right time. That there is a possible right time to quit a job or a possible right time to have a child or a possible right time to get married. 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 part of the brain that all mammals share. 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 digestion, our eye blinking, our heart beating. It also controls things like our adrenalin. So if you were to walk across the street and nearly get hit by a car you couldn’t think at that moment, “adrenaline kick in, keep me safe.” That is something that happens involuntarily.

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 hard-wired 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 will your reptilian brain to be, “Woo hoo! 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 I guess Dani Shapiro, was that confidence– and I think I mentioned this in part one of my interview with Tim– confidence is overrated. Dani 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 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 thirty or thirty-two or twenty-seven. The fact of matter is I didn’t have the courage or the confidence to do any of the things that I’m doing now at thirty or thirty-two or twenty-seven. 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 wanna do it now, my suggestion is to 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 Sciota asked you questions as well…

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Jimmy Sciota @ 14:44

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It was already hard getting paid before so now with all the services online competition based work and price dropping, etc., it seems like the graphic design market is losing a lot of value.

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Debbie @ 15:00

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Contrary, 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, 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 five dollars and doing the 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– the culture or the condition of graphic design and branding– reflect the condition of our culture and you’re not gonna be able to get that kind of work from a service that offers that kind of work for five dollars.

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 difference 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?

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Jimmy Sciota @ 14:45

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Where do I see a future for a graphic designer?

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Debbie @ 16:41

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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 Magalhaess also has two questions…

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Ricardo Magalhaes @ 17:00

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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?

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Debbie @ 17:17

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Ricardo, I think you would benefit from considering, what is the purpose of doing what you do? 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 yourself 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 Su Mathews Hale. Su Mathews 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– the great marriage, a child, a great career, she’d worked at Pentagram, she was a partner at Lippincott– the only thing I could 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, Su. I can’t find this information. Where were you born? Where did you grow up?” When she wrote me back, the answer 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 sounds kind of tough, but I think that thinking about what we want is hard enough. 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. What demons they are battling.

Your second question is…

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Ricardo Magalhaes @ 19:25

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What questions do you ask yourself to overcome the so dreaded imposter syndrome when planning to do some kind of work?

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Debbie @ 19:32

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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? And so the question becomes, do I want to do this badly enough or do I want to give into the notion that I don’t deserve doing it? 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.

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Daniel Carbone @ 20:03

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How did you come to the shift in your lead gene? You mentioned that your lead gean had once been living in Manhattan. But I’m curious how and when that shift occurred?

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Debbie @ 20:13

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Well, Daniel, it wasn’t a shift so much as a major realization. I had been telling myself for decades that I had compromised on the intersection of Sixth 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 thirty 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. I did whatever it took. I lived in this awful, deplorable tenement walkup. 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’ve lived anywhere. I could have lived with my mother. I could’ve 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 thirty 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.

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Mike Pendergast @ 21:59

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You’ve been so influential on so many properties from Star Wars to orange juice. I’d love to know more about your approach. What does your creative process look like?

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Debbie @ 22:09

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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. 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 endgame. What is the vision of that look like? And then either start doodling, start trying, 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. 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.

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Aspen Maja Okatie @ 23:46

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Do you do any other exercises with your students like the ten-year goal writing exercise? And if not, could you speak to your time as a teacher and what you’ve learned in helping others with life design?

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Debbie @ 23:57

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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. 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 the 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. We 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 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. 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. 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 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 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? 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 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 you’re intentional first impression is and then spend some time thinking about what is three words that only can be used to describe you. Take 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.

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Kelsey Hellman @ 27:58

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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.

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Debbie @ 28:10

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Kelsey, my first opportunity teaching came as an undergraduate teacher at School of Visual Arts where the chair of the graphic design and advertising department asked me if I’d be interested in teaching. And one of the things that I felt at that point in my life was that I wanted to try to work with students that were at the very spot that I was at the corner of Bleecker Street and Sixth 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 be accurate? And so that became my first class and I was teaching students extensively how to get a job. The actual classes was 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 that 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. I jumped at the chance. I love teaching. I feel that 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 they’re calling, as well as my firm belief that branding is not just a career about return on investment of advertising and marketing and positioning, it is a profound manifestation of the human experience. 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 Pussyhat. All of these things, humans are using the very tenants of branding to create social movements and social change and that’s why I do what I do.

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Nicole Haynes @ 30:49

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How do you ensure a healthy balance between work and play?

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Debbie @ 30:53

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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 my heart– my podcast, my teaching– until I was well into my forties. And so now that I have these opportunities to do these things, I’m just incredibly grateful to have these opportunities and I don’t see them as laborious. I just see them as joy. But, I also caution my students when they tell me, “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 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 gonna get to the painting or the essay on 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 are just not that important to you.

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Nicole Haynes @ 32:21

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What do you think’s 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?

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Debbie @ 32:30

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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 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.

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Leor Shank @ 33:13

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To what extent do you get creative blocks? Malcolm Gladwell mentions 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 effects. How do you stay so prolific?

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Debbie @ 33:30

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Leor, 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, they’ll get it done. 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. 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.

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Emily E. Godwin @ 34:34

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Who are some of your favorite visual artists?

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Debbie @ 34:36

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Well, Emily, Jean-Michel Basquiat is a perennial favorite. I also just met Deborah Kass and I’m smitten with all of her work.

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Kathleen Dylan @ 34:47

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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?

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Debbie @ 34:54

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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– whether they talk about it on the air or not– even in my research I found that the question what they do, how they do it, why they do it. The only two people that I’ve ever interviewed that seem 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 eighties when they told me this. So I kind of feel like by the time you get to your eighties it’s like, “Hey, fuck it. I am who I am. I do what I do, the world be damned.” And I think that’s wonderful. By the time you’re eighty, I think you should earn that. And so for all of us out there 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.

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Tony Fram @ 36:13

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In your view, what are the qualities of a good design student?

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Debbie @ 36:16

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Tony, curiosity. Wanting to learn. Being excited by learning. Always wanting to learn and know new things. Those of 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 as many as I can.

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Tim @ 36:43

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When you hear the word successful, who’s the first person who comes to mind and why?

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Debbie @ 36:49

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I would have to say Milton Glaser. As I 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. He’s made so much impact. He’s created the most profound logos, magazines, movements, and, of course, the I Heart New York Logo, which if there is 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.

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Tim @ 37:23

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What is something you believe that other people think is insane?

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Debbie @ 37:27

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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.

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Tim @ 37:52

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What is your favorite documentary or movie?

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Debbie @ 37:56

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My favorite movie is Manhattan by Woody Allen. I love that movie. I know that movie by heart. I also really, really loved the movies Fast Times at Ridgemont 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.

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Tim @ 38:21

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What are your morning rituals? What do the first sixty minutes of your day look like?

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Debbie @ 38:25

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Well, at this point in my life, the first sixty 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 sixty minutes are a mad rush to 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.

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Tim @ 38:52

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What obsessions do you explore on the evenings or weekends?

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Debbie @ 38:57

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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.

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Tim @ 39:13

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What is the best or most worthwhile investment you’ve ever made? It could be an investment of time, money, energy or other resource. How do you decide to make the investment?

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Debbie @ 39:23

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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 something, I tend to do it as often as possible. 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, which then became the High Line Neighborhood. So I think that quite by accident that became the best investment that I’ve ever made.

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Tim @ 40:04

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Do you have a quote that you live your life by or think of often?

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Debbie @ 40:10

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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 wave 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 way for me to self-sooth, but I really do believe that the longer that something takes, the longer it lasts and the less pressure you have to sustain it for the rest of your life.

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Tim @ 40:47

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If you could have one gigantic Billboard anywhere with anything on it, what would it say?

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Debbie @ 40:53

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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 ink. 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 we do it slightly more like this.” Those were things that really did benefit from the open-mindedness of both myself 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 dream this away.

This will be my last question…

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Tim @ 42:04

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What advice would you give to your 20, 25, or 30-year-old self? And please place where you were at the time and what you were doing.

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Debbie @ 42:12

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I’m going to say just anywhere between twenty and thirty because I have often said that that decade was ten 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 would be right here, right now. The arc of a life is really circuitous and you never know where you’re going and up. But what I can say is that despite all the pain and 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. 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.

End @ 00:42:27