Episode 31

Episode 29: Rejection, Perseverance, and Design Matters with Debbie Millman

Debbie Millman has worked with some of the world’s biggest brands including Burger King, Hershey’s, Haagen-Dazs, Twizzlers—just to name a few. She’s written six books, is a frequent keynote speaker on design and branding, and she hosts the first and longest running podcast about design, Design Matters.

In this episode, we discuss the drawing that started it all, why rejection can be worse than failure, how Design Matters got started, and why persistence is the key to success.

I don't think it's possible to make a name for yourself doing work for other people. I think that the way you make a name for yourself is doing original work on your own. Which doesn't mean you have to quit your job to do it. I was doing Design Matters while I had two full-time jobs.

This episode is brought to you by Wix. Push the limits of design and start creating beautiful, impactful websites that are uniquely yours at

Subscribe to Overtime on Apple Podcasts or Spotify. Or download the episode via Simplecast.


Debbie Millman: I think the thing that you can do, the way that I would guide people to try to do something for themselves is to do something where you don’t have to ask anybody’s permission for something. Where there aren’t parameters put in place by somebody else, in which to make something. If you can sit down and try to do something with that lack of parameters, it might help guide you to something meaningful.

Dan Cederholm: Hello, everyone. Welcome to Overtime, Dribbble’s official podcast. I’m Dan Cederholm, your host, and this is episode 29 with Debbie Millman. Where do I even begin with Debbie? She’s had an amazing career over the years. Was named one of the most creative people in business by Fast Company. She’s the founder and host of Design Matters, the first and longest running podcast about design. She’s interviewed over 400 artists, designers, and cultural commentators. She’s the author of six books. She co-founded, with Steven Heller, the world’s first graduate program in branding at the School of Visual Arts in New York City. She’s appeared in publications like the New York Times, the New York Magazine, Print Magazine.

Dan Cederholm: She’s the former president of the AIGA. It goes on, and on, and on. Debbie’s just an incredible person, extremely humble, and very candid in our talk about everything from predicting her life’s work, drawing at age eight, through dealing with rejection and failure in her career, and Design Matters, and how that got going, and how that’s been going strong, and how persistence can mean everything in your career in design. We thank her for being on. It was a real pleasure to talk with her.

Dan Cederholm: This week’s episode is brought to you by Push the limits of design, and start creating beautiful impactful websites that are uniquely yours with Wix. We’ll be talking a little bit more about Wix further into the show. I also wanted to take a minute to mention Hang Time Seattle. This is Dribbble’s forthcoming one-day event in Seattle on May 15th that we’ve lined up. It’s our second event like this. We did one in Boston last year. It’s a very great event. A full day of speakers, plus an after party. This year we’ve already locked in Aaron Draplin, Dana Tanamachi, Khoi Vinh, and Nathan Yoder, and several more.

Dan Cederholm: You’re going to want to go to to get tickets. There’s an early bird discount running currently, so please go over there and get tickets for that. It’s going to be a great event if you’re in Seattle, or near Seattle, or want to go to Seattle, you’re going to want to be there. The whole entire Dribbble team will also be in attendance as well, so it’s going to be a great time. But for now, let’s get on to our chat with Debbie Millman. Debbie Millman, welcome to Overtime.

Debbie Millman: Thank you, Dan. It’s great to be here.

Dan Cederholm: It’s awesome to have you here. Such an honor. You have such an amazing career, and so many stories. I’m just really excited that you’ve taken the time today to talk to us, so super excited. You’re host of Design Matters, which is the first and longest running design podcast, which is super impressive. You’ve interviewed over 400 people for that show. I’m wondering, because I’m kind of nervous right now because of that, because you’re like the veteran here, and I’m not. But I’m wondering after, so 400 people, do you get nervous? Has anybody made you nervous on this show, or is it like second nature at this point?

Debbie Millman: Oh my goodness. Have you listened to my recent episode with Marina Abramović. I was so nervous that the first word out of my mouth I flubbed. The first word. It was like… She was so kind and generous about it. First of all, I left this in the episode, so if anybody listens to it, it’s the very first thing you hear. You hear me flub, and then you hear Marina say, “Okay, Debbie. Breathe.” Then I go like this … She’s like, “No, no, no, no, no. Breathe, from the center.” Then we start breathing together. She goes, “In, one, two, three, exhale. Inhale. Exhale. Okay. Now, you can ask me question.”

Dan Cederholm: Wow. Is it weird that I was breathing there along with you. I think I need to do that, actually. That’s brilliant.

Debbie Millman: Yeah, you can hear. I was so nervous that I couldn’t even say one word without making a mistake.

Dan Cederholm: I think I need some breathing. That must’ve helped though the rest of the episode for you.

Debbie Millman: Well, I was so self-conscious about breathing, I think it just made it even worse for me, but she was so kind that that somehow evened it out somehow.

Dan Cederholm: This is great for me to hear, because I figure if you’ve interviewed 400 amazing people …

Debbie Millman: Okay, Dan. Breathe.

Dan Cederholm: Yeah, exactly. Okay, I need to do that as well. That’s incredible. I want to start off really with, if you don’t mind telling us the story of this drawing you did when you were eight years old, I believe.

Debbie Millman: Yeah, eight years old.

Dan Cederholm: It’s incredible. A, it’s impressive because you were eight, and it actually looks amazing. There’s a lot of detail in it.

Debbie Millman: I know. I was really impressed by it.

Dan Cederholm: Yeah. I was super impressed. I love the story behind this, because you drew this, and it kind of predicted your life’s work in a way.

Debbie Millman: Yeah, it really did.

Dan Cederholm: I wonder if you could tell-

Debbie Millman: It forecast everything that I’ve done in my adult life. Well, to give some background, it’s a drawing that I fond. My mother moved from Queens to Florida, like all good Jews. She gave me a box of ephemera that she’d kept in her basement that I didn’t even know that she had. When I went through it, it was book reports, and report cards, and all sorts of different ephemera. I came across this folded up piece of paper. Construction paper. I don’t know if you remember that from your childhood.

Dan Cederholm: Yeah.

Debbie Millman: I opened it up. It was very thin. I very gingerly opened it up, because it was folded in four, and I saw this drawing. It was something that I had no recollection of doing, but it was clearly my style. When I looked at it, I realized that without knowing what the future had in store for me at eight years old, I predicted a lot of what I ended up doing. I’m a native New Yorker, but at the time I was living in Queens, Howard Beach, Queens, and had only visited the city maybe one or two times to visit my dad when he was working at a pharmacy called City Drug right near Carnegie Hall. I guess that was my vision of what the city looked like. So, I drew a street scene. A city street scene, a Manhattan street scene, with stores on the street, and vehicles driving, and people walking.

Debbie Millman: I believe I was walking with my mom. I drew a little girl, and a mom, and she’s wearing a very popular Barbie outfit of the time, which I believe is called Tangerine Dream.

Dan Cederholm: Great.

Debbie Millman: I think labeled all of the various buildings and vehicles. The bank was labeled bank, and the dry cleaners was labeled dry cleaners, and the bus was labeled bus, and the tax was labeled taxi. But then, I drew a delivery truck, a big delivery truck which said potato chips on it, but in addition to the words potato chips, I also drew the Lay’s Potato Chips logo. There I am, looking at this drawing, like 40 something years later. I realized, okay, I am living in Manhattan, and I go to the dry cleaners, and the bank, and I’m on buses, and subways, and taxis, and I spent most of my career drawing logos for a living. So, there you have it. Just trust your inner artistic instincts when you’re little, and it will tell you everything about what you should be doing.

Dan Cederholm: I love it. I love that. Because I grew up in rural Vermont. My drawing of the world back then would’ve been green hills, and blue sky, and that’s it. Yours has so much color, and just energy. It captures the city, which is awesome. You were drawing logos at eight years old, really. From that moment on, was that sort of apparent that you would go into design, and creating brands and things?

Debbie Millman: No. I at that time had no idea what I wanted to do, but I was making everything at that point. I made a magazine with my best friend named Debbie. Her name was Debbie, rather, and we named our magazine Debutant, which I thought was really clever, and still a really good name for a magazine. What’s funny is, years, and year, and years, decades later, she reached out to me on Facebook I guess either reading or hearing about my talking about the magazine and was like, “Oh, I remember that. It was so much fun.” I was like, “Do you have a copy of it?” She’s like, “No.” I’m like, “Oh, damn. I would’ve loved to have …” Talk about finding the future, right?

Dan Cederholm: That’d be great.

Debbie Millman: I made magazines, and I used to direct little shows with my siblings for my family, and we’d be signing, and I’d do the set decorations. I made perfume from baby oil and rose petals. I was always making things. I think that’s what makes me happiest even to this day, just making things.

Dan Cederholm: Yeah, just being creative. Definitely creativity was a big part of your childhood, obviously.

Debbie Millman: Yeah, I mean I didn’t know that I’d end up being a designer, or even working in the world of branding, because back at that time in my life I didn’t know that those disciplines existed. I thought maybe I’d do something with art, or something with writing. I knew I’d like to write poetry, but I had no idea. As I think much as my parents might’ve loved me, I don’t know that they gave me particularly good guidance about what was possible. I was extremely insecure about what I could and couldn’t do, and really from a very, very early age operated out of a sense of fear as opposed to abundance or power. I was always worried that I wasn’t good enough to do pretty much anything, and have had to spend quite a long time trying to deal with that, and understand it, and try to get over it.

Dan Cederholm: Yeah, that sounds familiar. That’s imposter syndrome, right? That’s the way I think of it. Like, I can’t be an author, or a designer. Those are things other people do.

Debbie Millman: Yeah.

Dan Cederholm: Yeah, so I did read, or hear somewhere along the line you were talking about failure versus rejection. I think you were saying that in your mind rejection is sort of worse than failure as an experience.

Debbie Millman: I don’t know that one is worse than the other, but they’re very different. I mean, rejection is when somebody says to you, “No, we don’t want you. You’re not good enough. You’re not the right fit,” whatever it is. That is something that tends to be external. Failure is a sense of I think giving up. You can only say you’ve failed once you give up. In the meantime, you’re still trying. You might have obstacles and hurdles that you have to overcome, but you basically throw in the towel and say, “Okay, I’ve done everything I can do, and I don’t want to do anymore.”

Debbie Millman: That’s self-directed in a lot of ways. It might be as a result of marketplace conditions, or any number of things, running out of money, but you still are fundamentally making the decision that, “This is it. I’m done.” Whereas rejection, somebody else is telling you, “You’re done. We don’t want you.” I think they’re very different things. For a long time I thought that whole bunch of the things that I wanted to do that I wasn’t able to do were as a result of failure. I realized, no, that’s actually not it.

Debbie Millman: It was a result of being rejected. It’s up to me then to decided if I want to ultimately take that stance of being rejected, and have it be the final stance. Or, do I want to say I still want to do this anyway, and I’m going to figure out a different way to do it. That’s pretty much what I’ve tried to do, despite quite a lot of rejection, even rejection that I still get today. It’s not like easy street. You get to a certain point and you have some success, and therefore that just begets more and more success. It certainly helps to have some success in terms of credibility, and some sense of accomplishment internally, but it doesn’t mean that everything else that you try to do you’re going to be able to do smooth sailing.

Dan Cederholm: That’s both good and bad to hear, I actually think, for me. Because seeing like, Debbie Millman gets rejected. Why?

Debbie Millman: I get rejected on a regular basis, and I’m not joking.

Dan Cederholm: That’s surprising to me, though.

Debbie Millman: Yeah. I do.

Dan Cederholm: Because you’ve had so much success, and experience, and confidence, I would gather, from that.

Debbie Millman: Confidence is a really slippery slope. I’ve talked about this before, but for your listeners that might not have listened to my podcast or even know anything about me, it’s really worth talking about again. That is a conversation that I first had with a really incredible writer named Dani Shapiro, who writes magnificent memoirs. She was on the show a couple of years ago. After every episode of Design Matters … I do the show. I tape it live in front of a student audience, sort of like the way James Lipton does Inside the Actors Studio. There’s an audience there.

Dan Cederholm: Right. Yeah.

Debbie Millman: After I’m done with my interview, we come down to the sound studio, and we sit in front of the students, and the students have an opportunity to ask my guests direct questions, and the guest chooses who to pick. I’m not part of that. I’m just sitting there observing. Somehow, the conversation with Dani after the podcast was taped came upon the topic of confidence. I wish that I’d taped this, because it’s really one of the most significant conversations I’ve ever had.

Dan Cederholm: Oh, wow.

Debbie Millman: Dani ended up saying that she felt that confidence was overrated. That immediately peaked my interests. At that time there were a whole a slue of books that had just come out on confidence, and I’d gotten them all, and I was avidly reading them. When she said that confidence was overrated I was like, “Whoa, what do you mean?” She felt that, if you really look at it, most sort of obviously confident people are kind of often obnoxious. I agreed.

Dan Cederholm: True.

Debbie Millman: What she felt was more importance than confidence was courage. I asked her why. She felt that courage is taking a step into doing whatever it is you want to do, without knowing whether or not you’re going to be successful. That’s more important. People wait for confidence to be able to do something. I started to think, what is confidence? What is confidence? It took me about a year to come up with a definition that I felt was accurate. I feel that confidence is really the result of one thing. That is, the successful repetition of any endeavor. Once you have successfully repeated any endeavor, you then begin to expect that you can do that. That’s confidence. The expectation that you’re going to be able to do something to completion, and do it well.

Debbie Millman: The best example that I can give people is driving. When we start driving, the first time we get behind the wheel, most of us are really nervous. We turn on the ignition. We have this vehicle that we are now in command of. This huge instrument of possible destruction, and we have to run that. We have to manage that. Even when we take our driver’s license test, most people are really nervous, because they don’t know if they’re going to pass or not, because there’s not that confidence that we’ve done this so many times before, that we’re going to successfully accomplish this endeavor. But, after a couple of months of driving, then we have what I call car confidence. Every time we get into a car we don’t think, “Man, I hope I don’t kill someone today.” We have the sense that we can drive successfully.

Debbie Millman: I think that’s with any endeavor. You do something the first time … I can’t even think of anything that humans do the first time that we do successfully. We can’t walk successfully. We can’t talk successfully. We can’t do almost anything successfully. So, why would we think that something that requires a great deal of skill is going to be the one thing that we can do without practice? I think that Dani’s right. Courage is far more important than confidence, but you have to take that step into the sense of whatever nervousness you have, whatever fear you have, to be able to then make that attempt, potentially fail, and then do it again anyway, or keep trying until you get it right, if you want it badly enough.

Dan Cederholm: Yeah, that’s brilliant. I totally agree. I actually failed my first driving test, so that story makes even more sense to me. Because, I had to have the courage to go back again I guess and pass it. I wanted to pause here, and tell you more about our sponsor for this week’s episode. It’s With Wix, the web is your playground. Start with a blank slate, and design your website in any layout you want. Work with advanced features like retina ready image galleries, custom font sets, and sophisticated design effects.

Dan Cederholm: Each feature is intuitive to use, so you’re in control from design to live. With Wix, you’ll have real creative freedom to tell your story online, exactly the way you envisioned it. Push the limits of design, and start creating beautiful, impactful websites that are uniquely yours. Go to to get started today. That’s Wix, what will you create?

Dan Cederholm: You’ve been doing Design Matters for 13 years. Is that right?

Debbie Millman: Yeah. February 4th, it will be 13 years.

Dan Cederholm: Wow, which is incredible. Because, back then was podcast even a word when you first started?

Debbie Millman: I don’t know that it was a word. I was recording the show on a fledgling internet radio network called Voice America. I had gotten cold called by a producer there, thinking that they were offering me an opportunity to do the show, but they were really doing was offering me an opportunity to pay them money to produce a show for me, and essentially sell me the air time. I, at the time, was feeling really creatively bereft. Everything that I was doing at that point in my career was commercial, and all of the non commercial endeavors that I had been doing for most of my life, whether it be painting, or writing, or drawing, or anything-

Dan Cederholm: You’ve been doing Design Matters for …

Debbie Millman: Had fallen to the wayside in this quest that I had at that point to try to make a success of myself professionally. After a decade of doing that, I had some success, and was really grateful for that financial success, and professional success, but felt that my soul was dying creatively. When I had this opportunity that I hadn’t expected pop up offering me this chance to do something that I’d never done before, and because I had some money saved I thought, “Why not invest in myself and perhaps do something that I could learn from, or just experiment with?”

Debbie Millman: I started doing the show. The show was recorded live on Friday afternoons, at three o’clock Eastern time. Then it was rebroadcast another time during the week at like 2:00 a.m. Unless you were listening to the internet radio at the time I was being broadcast, you couldn’t hear the show. People started asking me if there was a way I could post it somewhere, so that they could listen to the show when it wasn’t live. I thought, “Oh, let me start putting it up on iTunes,” sort of like the way new musicians were putting up their digital files of their music. A couple of other people were doing that as well.

Debbie Millman: I think there are less than 10 podcasts still recording that started back then. I think on Wikipedia there’s a list of podcasts, and the year that they started. I saw that Design Matters was on it, which made me very, very happy.

Dan Cederholm: Wow.

Debbie Millman: I think that podcast started being recorded I think in either 2003 or 2004, and I think that there are less than 10 of us that have been continually broadcasting since then.

Dan Cederholm: Wow. That’s incredible. What’s really interesting about this too is I remember hearing you speak. You actually spoke at our Hang Time conference, Dribbble’s Hang Time in Boston, and you were talking about persistence. If someone came to you and said, “I want to start a podcast. How do I get to the point where you are with Design Matters?” How would you answer that, I guess?

Debbie Millman: I say that anything worthwhile takes a long time. I grew up in public as a podcaster. My first 100 episodes, many of them are unlistenable, in my opinion. I still keep them up there in an archive called the Design Matters Archive on iTunes, and the sound quality is really terrible, because who knew that podcasting would be podcasting back then. I was recording the show initially in 2005 with two landlines, handsets.

Dan Cederholm: Really?

Debbie Millman: Yes. Yes.

Dan Cederholm: Like a plugged in phone.

Debbie Millman: Yes. So, I would call a phone number in Arizona, where my producers were, from a landline. My guest would do the same. We would have a conversation through the telephone lines that was connected in Arizona by the producers at Voice America. Back then, I really felt like I was recording an episode of Wayne’s World. I mean, it was so prehistoric. We had the sensation of … I don’t know if you have ever been on a landline in a home with more than one phone, and two people get on the same landline at the same time to talk to grandma.

Dan Cederholm: Yeah.

Debbie Millman: And you hear that echo of the two voices. Well, that was what it was like to record my shows. At least the first 50 I think, and then I got some slightly better equipment, and it was somewhat better, but still really spotty. I used to get a lot of comments back when I first started. People started rating and commenting on iTunes and they’d be like, “Great content, but what’s with the sound, man? It’s terrible.” Finally, in 2009 I was invited to bring the show to by the late great Bill Drenttel, and he invited me to bring the show to Design Observer, but with the proviso that I improve the sound quality. He introduced me to a producer named Curtis Fox, who at the time was doing work with the New Yorker, and the Poetry Foundation, and he became my producer. He’s been my producer ever since. We’ve been working together now for nine yeas.

Dan Cederholm: Wow, that’s fantastic.

Debbie Millman: We’ve done about 300 episodes together. Then my previous archive is that other 400. But, I do keep it up so people can listen. I grew up as a podcaster in public, and I think, I hope that I’ve improved over time, and learned how to really conduct a conversation that is meaningful, and offer something that people just don’t hear everywhere else. I try not to ask my guests the same questions that I read in my research. What I prefer to do is actually ask them about their answers, so that we go into something deeper and a bit more intimate.

Dan Cederholm: Yeah. All right, I’m throwing my list away. That’s amazing, though.

Debbie Millman: I think it’s very possible that your listeners might not have heard anything I’ve ever said before, so in some ways I do think it’s important to talk about a person’s origins, but to try to do it in a way that makes it feel a little fresh, if possible. But you can be as stale as you want with me. I’m cool.

Dan Cederholm: No, I think for you it’s hard, because there are so many directions to go in, because you’ve had such a …

Debbie Millman: Haphazard career.

Dan Cederholm: Diverse career, doing all sorts of things. I’m looking at my list of topics here and I’m like, there’s a lot of cool stuff that I hope we can dig into. Persistence, I think that’s important. Especially when young designers, through Dribbble for instance, they would say, “How do I make a name for myself?”

Debbie Millman: Hard work.

Dan Cederholm: Hard work, right?

Debbie Millman: Hard work for a long period of time. It’s very rare to have the Jessica Walshes, and Jessica Hisches, and the Timothy Goodmans who come out of the gate, and hit the ball out of the park first pitch.

Dan Cederholm: Yeah, right.

Debbie Millman: It’s really rare. For every one of those, there’s probably 100, or 200, or 300,000 people that are slogging away, and trying to figure it out. To those people, because I was one of those people, I say keep trying. Keep trying with self-generated work. I don’t think it’s possible to make a name for yourself doing work for other people. I think that the way you make a name for yourself is doing original work on your own. Which doesn’t mean you have to quit your job to do it. I was doing Design Matters while I had two full-time jobs. One at Sterling Brands, and one at the School of Visual Arts.

Debbie Millman: I had a day job at Sterling, and a nigh job at SVA, where I’d been running a graduate program. You make the time to do what you want to do. That gets back to the other thing that I say all the time, which is busy is a decision. If you say, “I’m to busy to make self-generated work, or to make work that I feel is different, or attempts to be original in some way,” then it’s just not a priority. It’s just not something you really, really, really want to do. Because, we somehow find the time to watch Game of Thrones, or House of Cards, or Homeland, or whatever it is. If we have time to binge watch a TV show, or spend three hours last night watching the Grammys, you have time to make work.

Dan Cederholm: Yeah, if you love what you do, and you believe in it, then being busy doesn’t seem like a chore, right?

Debbie Millman: Yeah, I feel like it’s not really work then. It’s really a labor of love. That being said, I do have to really be clear that I am not married, and I don’t have children. That does make my time a bit more elastic. But, I do feel that because I ran a business for 22 years of at one point 150 people, and a graduate program with 20 plus students, it did make my time a little bit more complicated and restricted, but it was still important enough to me to try to make something that was non commercial, that was from my heart, without restrictions.

Debbie Millman: I think the thing that you can do, the way that I would guide people to try to do something for themselves is to do something where you don’t have to ask anybody’s permission for something. Where there aren’t parameters put in place by somebody else, in which to make something. If you can sit down and try to do something with that lack of parameters, it might help guide you to something meaningful.

Dan Cederholm: Yeah, I totally agree with that. That’s actually an interesting opposing opinion about … Well, some people say, “Well, you shouldn’t show work that isn’t real.” If it’s not from a client or something.

Debbie Millman: But, what is real? What does real mean? If you’re creating a visual essay, if you’re creating a graphic novel, if you’re creating some type of visual identity for something that you’ve created, how is that not real. I think that real is a subjective word. If you mean it’s not being sold in the marketplace, and people aren’t buying it, then I don’t know that Design Matters would qualify, because it’s free.

Dan Cederholm: Yeah, interesting. Yeah, I totally agree. I love that.

Debbie Millman: How did Dribbble come about? How did that happen? If somebody had said early on, “Who are you making this for? Is it real?”

Dan Cederholm: True. True.

Debbie Millman: Real is on a spectrum.

Dan Cederholm: Yeah, it was certainly a side project.

Debbie Millman: Like gender and identity, I think real is on a spectrum.

Dan Cederholm: Yeah, absolutely. That’s good news for everybody that’s creative, I think. You’ve got to start making stuff, even if it’s just for you initially.

Debbie Millman: Then the other part of it is, why are you doing what you’re doing? If the goal is fame and fortune, it’s not really a good discipline to be experimenting in. There aren’t that many graphic designers that are independently wealthy.

Dan Cederholm: That’s true.

Debbie Millman: If fame and fortune is really your end game, then maybe going into entertainment is a better bet. I think that meaning making is sort of what designers do. If you’re making something that’s meaningful, then that’s the reward. Financial independence is an amazing thing to have, but if that’s the goal, you very well may risk creating something that’s meaningful, because you’re in the pursuit of other things. I spent a lot of time in the pursuit of other things, mostly because I was terrified of not being self-sufficient, and I wasted a lot of time in that regard. I felt that safety and security was the most important thing to me for a very long time, because I didn’t feel that inside. The one thing I can say is the pursuit of safety and security does not come with a bank account. It doesn’t get solved with a bank account. That’s what I mean.

Debbie Millman: It’s something that you have to work on that goes way beyond what you think you need in order to feel or accomplish that. That can only come inside. I remember when I was in my early 20s, I remember thinking, “Oh, if I only had $1,000 in the bank, I would feel safe and secure.” That was in the ’80s. It was a long time ago. $1,000 was a lot more money than it is now. But then, as soon as I had that it was like, “Well, maybe I need $2,000,” because things don’t really make you feel safe and secure. If you feel insecure, you have to work on why you feel insecure.

Dan Cederholm: Yeah, and then it’s 4,000, and then you’re never secure if you don’t work on that.

Debbie Millman: Yeah, exactly it’s a hedonic treadmill, and you always need more, and more, and more to fill you up.

Dan Cederholm: Yeah.

Debbie Millman: Boy, I’m really taking you down a buzz kill here, aren’t I?

Dan Cederholm: No, actually I look at it the other way. I look at it as encouraging for … I think as a young designer, and I was in this boat too, very intimidated by just the industry, and how do people break in? How do they get to where they are? I didn’t go to school for much of anything actually, so I had self-conscious-

Debbie Millman: I went to school, and my degrees are in Russian literature and English literature. I joke now that I have a degree in reading.

Dan Cederholm: Oh, wow.

Debbie Millman: I didn’t study design.

Dan Cederholm: See, that’s great to hear. That’s also great to hear, because I think once you have been persistent for a certain amount of time you realize that people got to where they are like you said earlier, from working hard, and putting yourself out there, and taking the risk. Going back to Dani Shapiro’s, having the courage to take the risk. I think that that’s something that everyone can do. It’s not easy for everyone, but it’s something that everyone’s capable of doing, which is encouraging I think.

Debbie Millman: what did you go to school for?

Dan Cederholm: I went to school for, funny enough, audio engineering.

Debbie Millman: Interesting.

Dan Cederholm: Yeah, and I was a musician, and I just wanted to play music. Part of it was like, “Well, I don’t know if I can make a living doing music. Maybe I can get a job recording it.” But never really applied that, because the hours are crazy and all that. I had minimum wage jobs, and then until the web came along really, and that kind of changed everything for me. It sort of brought all the creativity into one place where I could learn by just reading people online. The mystery of design for me kind of eroded away a little bit I think with the web, and the internet, and connecting that way.

Debbie Millman: I wish it did for me.

Dan Cederholm: Yeah, does that … Same?

Debbie Millman: No, no.

Dan Cederholm: Oh, no. It didn’t.

Debbie Millman: I still, I find the whole web very mysterious, and alluring, and seductive, but really a mystery.

Dan Cederholm: Wow, yeah.

Debbie Millman: I mean, it helps to be able to know how to do things in the way that you do.

Dan Cederholm: I see.

Debbie Millman: I don’t have that same skillset.

Dan Cederholm: But there’s so much more. If we go, I want to dig into your time at Sterling.

Debbie Millman: Sure.

Dan Cederholm: This is what’s fascinating about you I think, because you’ve had sort of facets of your career that on their own are incredibly impressive, and then you add them all up, and it’s kind of overwhelming. You were at Sterling Brands, and you’re working with huge companies. Burger King identity, and Hershey Bar I think is another one.

Debbie Millman: Yeah. Twizzlers.

Dan Cederholm: There’s a whole bunch of them.

Debbie Millman: Häagen-Dazs. Yeah.

Dan Cederholm: Häagen-Dazs. Basically go to the supermarket, and you’re looking at Debbie Millman’s work. How did you get there? Because that’s a whole different … Going from drawing the Lay’s Potato Chip logo when you were eight to working on brands that are giants.

Debbie Millman: I would say that it was completely circuitous. I graduated college, as I said, with a degree in reading. My one skill was old school layout and paste-up, because I learned that on my student newspaper back in the early ’80s. When I was a senior in college, I was the editor of the Arts and Feature section of the student newspaper. One of the requirements of the editor was to actually make the paper as well. We had to design and layout the paper. I very quickly fond out, just by doing it, how much I loved it, and loved it maybe even more than editing, and writing.

Debbie Millman: When I graduated, I needed to be able to make a living, and the only skill that I had, the only marketable skill was layout and paste-up, and so I started out as a layout and paste-up girl in a bullpen at a cable magazine. Worked in the design business for 10 years. I had my own business for a little while with a friend of mine named Cliff Sloan. He has his own business now. I left that business. He ended up selling it, and making a lot of money.

Debbie Millman: I was really confused about what I could do, and what I couldn’t do, and I wanted so much. I guess, if I look back on it I’d say my pervasive feeling all through the ’80s and ’90s, or the first half of the ’90s was longing. I just longed for so much. I didn’t know how to make it happen. What I thought was going to be the big job of my dreams at a company called Frankfurt Gips Balkind in the early ’90s ended up being a bit of a nightmare, in that the person that hired me didn’t really like me very much.

Debbie Millman: At that point, I would say it was a career low, because this was what I thought would be my dream job. I thought this was going to be the job that would change my life, and worked really, really, really hard to get it. Then when I did, they didn’t want to hire me as a designer. They didn’t like my work. They hired me as an account executive, and that meant I had to be managing other designers. Even that was a nightmare. Not that the job itself was a nightmare. It wasn’t particularly fulfilling, but being there was hard, because I wasn’t liked by the boss. My advice to people is never go to work for somebody that doesn’t like you, because it’s never ever going to get better.

Debbie Millman: They’re never going to wake up one morning and say, “Well, I’m really glad I did hire that person.” It does not work. I stayed there for about a year. I was so unhappy, and I got a cold call from a head hunter, and so the big theme here now is second time … Well, this was the first time I’d gotten a cold call from somebody that changed my life, because the second one was with Design Matters, but I got a cold call from a head hunter who had a job at a branding agency, but it was as a sales person. Here I’d gone from being a designer, to what I considered to be a rung down, which was an account executive, and now I was going potentially another couple of rungs down. Not even managing the work. Just selling the work, and then giving it to somebody else to manage, and somebody else to design.

Debbie Millman: But I was so desperate to find another job that I went on the interview. I got it. Then, became a sales person at a branding consultancy called The Schechter Group in the early ’90s, early mid ’90s. For the first time in my life, I was good at something. As much as I dreaded the idea of being a sales person, I think because of all of the experience that I had in my dad’s pharmacy, working on the weekends when I was in college, growing up in that environment full of brand, having that sort of sense of … I mean, drawing a logo at eight years old. I’d had this sort of instinctual knowledge and understanding, and I don’t know an allegiance to brands and branding, and so I was really good at it.

Debbie Millman: Unfortunately, the company was in the middle of an implosion. They were merging with Interbrand, and my boss walked out one day, and the creative director walked out. At that point I knew another head hunter and called her, and asked her if she knew of anything out there. She recommended that I meet with Simon Williams who is the founder and CEO of this tiny company called Sterling Group. He had bought the company out of bankruptcy from Michael Peters when it was The Michael Peters Group earlier in the ’90s, I guess late ’80s early ’90s.

Debbie Millman: He was really struggling to make this business come alive, and I was struggling because I had this skill, but didn’t know where to put it. We met, and he offered me a job, and I started there in 1995, and it was one of the best decisions that I ever made. They needed me, and I needed them. Together, Simon and I created this business that for quite a long time seemed unstoppable. We were just in a real zone together. We build this company. When I started it was one small office. Maybe less than 20 people. I would say maybe 15, 18 people, and when I left in 2016, we had 150 people in five offices. In 2008, we sold the business to Omnicom, and then I stayed on for another eight years after that. Then finally, finally took the big leap into the great unknown to do what I’m doing now.

Dan Cederholm: Wow.

Debbie Millman: It was a great run. It was a great run. I loved what I was doing. But, by the end I was very disillusioned with the state of branding, and the state of politics, and felt that I needed to use whatever talents I had to do something that was a bit more meaningful.

Dan Cederholm: That’s interesting. Yeah. Earlier on, I think you had received, and this is kind of unbelievable to me actually, but you had received some criticism of some of the branding work that you were doing.

Debbie Millman: You mean on Speak Up?

Dan Cederholm: Yeah. I didn’t know about that until recently in my research here, but I was kind of shocked at that, because to me working on brands like Hershey, that’s impressive. That’s sort of like, for someone that’s into branding and wanting to do that, to me that’s where you want to get. The pinnacle of working with these brands that millions of people are going to see. I was kind of surprised by that.

Debbie Millman: Well, it was a different time. That was 2003, and what you’re referring to, for the people that might not know, I very unexpectedly found that I was being taken down by a web blog. It was the first ever design blog called Speak Up, and that year I had been asked to be a juror in AIGA’s national competition. AIGA is the American Institute of Graphic Arts. I actually had been invited to be a juror, because I had been rejected from a brand experience group that I had already been on the board of. When I applied to be on the board again, I was rejected when every other single person on the board was accepted, so I was the one person that was rejected from that. I was really, really hurt by it. They apparently thought my work was too traditional.

Debbie Millman: I was really hurt. I loved being part of that group, and I loved working with AIGA at that time. When that happened, Ric Grefé, I guess as a bit of a consolation prize asked me if I wanted to be a juror in the upcoming competition, in an effort to really still keep me involved. It was a very gracious and generous thing to do. So, I did it, but then when the book came out, when the annual came out, all the jurors had work in the annual to validate their being a juror, and my work was Burger King, and some work we did for Star Wars, and so people felt that it was way too commercial, and ugly, and that I had no business being involved in this prestigious competition, and that AIGA had sold out to us corporate clowns. I was referred to as a she-devil who was trying to manipulate AIGA for my own benefit.

Dan Cederholm: Oh my God.

Debbie Millman: Which none of this could’ve been further from the truth. I mean, all of this couldn’t have been further from the truth. I had actually been rejected by AIGA, and Rick was trying to give me a bit of an olive branch to keep me involved. At that moment in time when that article came out in May of 2003, I really felt like the most hated person in design. I felt like everybody int he sort of establishment, which was AIGA had rejected and hated me, except maybe Rick. And everybody in the anti-establishment which was Speak Up, these young kids trying to make a difference and take down all the sort of monoliths around had also hated me. It was really hard. It was a very hard time in my life. I felt really profoundly rejected.

Debbie Millman: I ended up writing in to try to defend myself in an ever so dignified manner back then, and I think I held my own. Then Armin Vit, the founder of Speak Up wrote to me separately, and apologized for calling my work “a pair of turds” on the internet. He didn’t apologize for actually feeling that way. He actually apologized for articulating it in that way. Armin and I have since become really good friends. I’m friends with his entire family. He’s actually one of my closest friends, and I am the godmother to his oldest daughter. It’s a very happy ending.

Dan Cederholm: That’s incredible.

Debbie Millman: It is incredible. It is really incredible. Armin actually designed my website, my current website,

Dan Cederholm: Wow.

Debbie Millman: He designed it, and it’s absolutely stunning. Yeah, you never know where life is going to take you.

Dan Cederholm: My goodness.

Debbie Millman: I say that that worst moment of my life turned out to be the most important, because that notoriety then parlayed me into being able to write for Speak Up, which I did, which then resulted in my meeting Joyce Kaye, the then editor-in-chief of Print Magazine, who then asked me to start writing for Print Magazine. Then it caused Emily Oberman, who was the president of the New York Chapter of AIGA to take an interest in my work. Then she invited me to be on the board of the New York chapter of AIGA. Then before you knew it, I was on the national board, and then I was the president of AIGA, all of AIGA. It was crazy. Nobody would believe this if it hadn’t actually really happened. It wouldn’t seem possible.

Dan Cederholm: That is incredible. The two institutions, and actually Speak Up not an institutions, but these two things that were so critical of you, you ended up being a part of, and also the president of. That’s just absolutely incredible.

Debbie Millman: Life is very mysterious, Dan.

Dan Cederholm: Oh my gosh, right. That’s got to feel good, right? After you were saying it was a tough time.

Debbie Millman: Yeah, it does.

Dan Cederholm: What was going on, but then to turn that around.

Debbie Millman: It feels magical actually. I’m not a woo hoo kind of person, but I can’t help but feel like that was just some sort of strange destiny.

Dan Cederholm: Yeah, I think it was. I’m glad it happened that way. I shouldn’t say that. Tell me if you feel like that experience helped fuel another chapter of your career, I guess.

Debbie Millman: Yes. Absolutely. What I can say for people who have experienced or are experiencing either similar kinds of rejection, or feelings of not being good enough is try as best as you can to let other people feel what they feel, but don’t let those feelings prevent you from doing whatever it is that you really, really want to do. If you really, really want to do it, if you let anybody stop you from doing something meaningful, then the only person that’s going to suffer is you. It might not be the right avenue, or the right moment, or the right opportunity, but if you want something badly enough, my feeling is you have your whole life to make it work.

Debbie Millman: If you feel that if you haven’t done it by the time you’re in your 30s, so what? So what? I feel like the longer it takes, the longer it’ll last. I think that the people that make it really quickly have the then added burden of having to sustain that success for the rest of their lives. Whereas, if you’re a slow burner, and then take time to be able to express what you want to express, and do it in a way that gets the kind of response that you feel is important to you, then the longer it takes, then the more likely it is that you’ll have more longevity. You’ll just be doing it for that much longer.

Dan Cederholm: That’s a really interesting perspective on that, and super encouraging I think. Maybe instead of design, I can finally be that rockstar I always wanted to be.

Debbie Millman: Yeah, I mean even in this conversation. My real first success, professional success. I mean, I had a couple of other things that I did that I was really, really proud of prior, but my first real sort of sense of accomplishment came when I started at Sterling in 1995, and even that took a few years to manifest. At that point, I was already in my mid 30s. I didn’t really, really manifest something with Sterling until I was in my 40s. Give yourself some time and some runway.

Dan Cederholm: Yeah, that’s wonderful. As a last question, do you still take cold calls today?

Debbie Millman: I don’t get so many. I get a lot of cold emails, and I try to keep up with them.

Dan Cederholm: Yeah, I suppose email is …

Debbie Millman: But I do get the cold call occasionally. I’m always nice to cold callers, because I just feel like it’s such a hard job, you have to be. But, I do get a lot of cold emails. The issue that I have is just keeping up with them, but I do try, but I’m not always as quickly responsive as I would like to be.

Dan Cederholm: Right. You’re right.

Debbie Millman: It’s really hard.

Dan Cederholm: Yeah, no it is. It’s very hard. You’re right. I guess back in the literal cold call days, the phone can only ring a certain number of times.

Debbie Millman: Dan, you know what I tell people now is if you want to reach someone, the best way to try to get to them is by calling, because people don’t really talk on the phone anymore.

Dan Cederholm: Yeah.

Debbie Millman: I mean, when was the last time you talked on the telephone. It’s very rare. We text. We Skype. We WhatsApp. It’s a very different world.

Dan Cederholm: It is.

Debbie Millman: I remember back in the day when I was doing my first book, How to Think Like a Great Graphic Designer, I wanted to interview Massimo Vignelli, and I had never met him, and I decided I would just call his studio to see if I could speak to an assistant, to see if I could arrange to interview him for my book, and he answered the phone. Massimo answered the phone.

Dan Cederholm: No way! Really?

Debbie Millman: Talk about a tongue twister. I could barely speak. Yeah.

Dan Cederholm: You weren’t expecting him to pick up.

Debbie Millman: I was not expecting him. He was really nice and said, “okay.” Then, because I was such a clod, when I first met with him and did my interview, I thought he pronounced his last name Vignelli, and said to me just as we were starting the interview he said, “No, no, Debbie. It’s Vignelli. Vignelli.” I was like, “Oh, God. I am such an idiot. I’m such an idiot.”

Dan Cederholm: No, but you’re not. I mean, you called him, and you took the risk, and it worked, and he talked to you. That’s fantastic.

Debbie Millman: I mean people, given the choice, I think mostly are generous.

Dan Cederholm: Yeah. I think you’re right. I think calling somebody is … Email is just too hard to keep up with, but calling. That’s good advice.

Debbie Millman: Yeah, especially if there’s a big giant PDF associated with it. That’s just a real obstacle.

Dan Cederholm: Yeah.

Debbie Millman: Send people something in the mail that’s beautiful, that’s going to capture their attention, that is uniquely meant and made for them.

Dan Cederholm: Yeah.

Debbie Millman: Or, call somebody on the telephone. But email is just a lazy way to try to feel like you’re being productive.

Dan Cederholm: Yeah.

Debbie Millman: That sounded harsher than it is, but it is pretty true.

Dan Cederholm: No, I totally agree. Yeah, and physical mail, yeah, huge. It’s funny. When we started Dribbble, we sent out … Before it was Dribbble really, but we sent out handwritten postcards and a t-shirt to people that I wanted to see … Selfishly, I just wanted to see what they were working on. I think in a way it sort of guilts people into checking something out more than an email would. Like, “Hey, I’ve got this new thing. Check it out.” I think if you send, yeah, something physical …

Debbie Millman: It’ll capture somebody’s attention, and if they like it then they’ll remember it.

Dan Cederholm: Yeah, absolutely. This has been awesome, Debbie. I can’t thank you enough for being on here today with us.

Debbie Millman: Thank you, Dan. I really, really love what you’re doing at Dribbble, and congratulations for all of your success. It’s such a great, great thing that you’re doing.

Dan Cederholm: Thanks so much. That means a lot. We’re going to keep listening to you on Design Matters, and find you at Keep up the awesome work.

Debbie Millman: Thank you, Dan. You too.

Dan Cederholm: Bye bye.

Debbie Millman: Bye.

Dan Cederholm: This has been Overtime, Dribbble’s official podcast. I’m Dan Cederholm, and thanks for listening to this week’s episode. Please subscribe to us on Apple Podcasts, or wherever you listen to podcasts, and we’ll see you next time. Thanks again.