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Debbie Millman on rejection, bravery, and the power of small, slow steps.

Creative Business
min read
In this article

This week on the Brand Your Passion podcast, I was joined by writer, designer, educator, artist, brand consultant and host of the podcast Design Matters, Debbie Millman!

Debbie is a branding expert and creative, and has been named “one of the most creative people in business” by Fast Company, as well as “one of the most influential designers working today” by Graphic Design USA.

In this amazing episode, we talk about the pressure to “make it” in your twenties, how the best opportunities can come from the worst moments, and the oxymoron of personal branding . Plus so much more!

Hey everybody and welcome back to this week's episode of Brand Your Passion. I am super excited and it is my honour this week to be joined by branding legend and creative, Debbie Millman. Welcome to the show Debbie! 

Thank you Hollie, it's really, really nice to be here. Thank you so much. 

You are so welcome! It is obviously my massive honour to have you on the show. And I am obviously dying to hear your branding expertise for the creatives who are listening to this episode, but I also am really excited to hear about your own creative journey and how you have built your own personal brand. And I've done a little bit of research about you. So I want to go back a little bit to when you were kind of young and how your creativity came through, if it did, as a child.

I read that your mother was a seamstress and your father owned his own pharmacy, and I'm curious to know if you think that growing up around those creative and entrepreneurial parents helped draw you to a life as a creative. 

Well, I think that we're all influenced by how we're brought up. And I think I was impacted both by the talent and the intelligence that my parents had, as well as their circumstances. And I think they're probably pretty equal in terms of what they were able to provide for me in terms of their drive, their ambition, their talent, but also the ways in which their own struggles and psychological issues impacted the way that I am now. So yeah, I do think all of that is, is super important in terms of how we shape how our personalities are shaped and how we make our way through the world. 

Yeah, definitely. And so do you think that you were kind of creative as a child, as a young person? Were you creative back then? 

Oh yeah, I was always making things, always, always, always making things. I was putting on little shows with my brother and I was making window decorations and I made my own perfume from rose petals. I made a magazine with my best friend. There was always, always something that I was doing that kept me creative. 

“There was always, always something that I was doing that kept me creative.” 

And from being a child, you ended up growing up and studying English with a minor in Russian literature. How did you get to that stage of your life and doing English?

Well, it really wasn't something that was well thought out. I was really quite confused at the time about what I was capable of doing, what I was worthy of doing. And for me, it was just an easy way to think about doing something that I enjoyed. You know? I majored in English and minored in Russian literature, but really I have a degree in reading. I wouldn't say that either was chosen very strategically in terms of what my future prospects for employment would be. You know, it was very much – this is what I enjoy doing and so let's just formalise it as a major. 

And I think so many creatives do that. Right? And going to college or university becomes sort of a time to figure those things out and realise, okay, this is what I want to do or this isn't what I want to do. 

Right. Exactly. 

Yeah. And throughout that process, you were writing in the school newspaper, which is where you found design, is that right? 

Yes. Everybody that worked on the paper from an editorial perspective was also expected to put the paper together. And so I was very involved in the design by default. That was part of my responsibility. So I literally learned on the job and found that I love designing the paper as much, if not more, than conceptualizing the ideas for each issue, assigning the writing and editing. Like I loved doing the design and spent a lot, a lot, a lot of time doing it and really fell in love with it. 

Debbie never gave up writing, even after becoming a designer. She has since written six, soon to be seven. Here is one of Debbie’s books, Brand Thinking and Other Noble Pursuits.

What was that experience like for you, having studied one creative passion – you said you love writing – but then finding something else in that process? Was it kind of exciting or was it like, “oh, I've just spent these X amount of years doing this?” 

Well, I think that at the time I really have to say looking back on those years that I was just an embryo. I was just beginning to become a person. I was so cut off from my interior life. I was so consumed with trying to find a way into the world that made sense, that it's hard for me to even remember what I might've been thinking. 

I do have some diaries of that time so I have been able to look back. But even rereading the way that I constructed my life, it feels very foreign. And I was really just trying to survive, you know? I didn't have any real role models. I didn't have any guidance. I didn't have any money. I didn't have any connections. I was super insecure and felt very unworthy of anything great. But on the other hand, I also wanted to have a great, sort of purposeful life. I had no idea what any of that meant. So it's very hard to look back at that time and think of my living at that moment very deliberately. I was just sort of trying to make my way forward and survive. 

And just knowing that you were enjoying the process of design so I'm just going to follow that and see where it goes?

It wasn't even following the process of design. It was – this is the only marketable skill that I have that will allow me to make money. And so I leveraged that little bit of experience that I had into getting my first jobs. 

What I didn't realise at the time is how woefully unprepared I was to actually pursue a career in design because I had learned everything on the job, working at my student newspaper, and didn't have any formal training. And so I remember going to an agency that helped place designers in freelance positions at magazines and in advertising agencies and so forth, and in order to be qualified to do that from the agency, I didn't know this till I got there, but you had to take a test. And it was really, you know, looking back on it now, it was a super simple test – how many picas is to an inch and so forth – but I didn't know any of these things. And I was so humiliated. I got this test and I'm sitting in the waiting room and other people are filling out the test and I knew I was going to fail. So I didn't want to take it, but I didn't know what to do. I couldn't run out crying which is what I wanted to do. So I just said I had to go to the bathroom and then I never came back.

But I mean it was a really humiliating experience because at that moment I realised how much I didn't know that I didn't know, and was really still trying to make it just by the seat of my pants, so to speak, and just kept learning and growing. And I remember being in another situation where I was freelancing and all of the type that I was laying down, (cause back in the day it was paste up and old school layout, that was before designers were setting their own type.) and, the margins didn't line up. And I remember the woman I was working for saying, “where did you pick up your skills? ‘Cause girl you don't know what you're doing. I'm paying you to do this and you’re not doing it right.” So that's how I kept learning. By people telling me I wasn't doing it right and then figuring out how to do it right. 

“That’s how I kept learning, by people telling me I wasn’t doing it right and then figuring out how to do it right”

Yeah. Wow. What a kind of immersive experience to learn so much on the job. And obviously I'm sure that wasn't a fun experience for you to keep being told that you were doing it wrong. But I think there's something to be said about the amount of people these days who are learning themselves and teaching themselves these skills, that it is doable. It's just a different process than going to study. 

I mean, some people get their degrees and know what they want and come out of the gate and get really interesting internships and then really interesting jobs and kind of move forward on a path that's very determined and deliberate and intentional. That was not the case with me at all. 

I graduated, I didn't have any idea what I was doing. I was living in a 10 minute walk up apartment. I was constantly learning as I was making mistakes. It took me a long time to figure out that I was good at what I was good at, which was branding. That took about 12 years. And so every single step was a small one. There were very few leaps, if any. And it was a slow methodical climb. 

Wow. And you mentioned earlier that you said that you knew you wanted to do something big, but you weren't sure if you were ready to do that or worthy of doing that. And I read in an interview that you said “I wanted to do something special but frankly I didn't have the guts to.” But that changed when you were about 30 and you decided you were going to change your life. What changed for you when you said “no, I'm going to do something about this. I'm going to change my life”? 

Well,I didn't go easily into that change. You know, I nearly had a nervous breakdown in that realisation. I mean, by the time I was 30, I already had a bad marriage behind me. I had had a year, well what I would consider now to be a decade, of rejection and failure in trying to find work and trying to find meaning. I mean I've always wanted a special life. I just didn't always know how to go about creating one. 

“I’ve always wanted a special life, I just didn’t always know how to go about creating one.”

And as you kind of had that slow change and realisation after, or during that time, how did you realise what you wanted or how you were going to get there, I suppose?

I'm still working on that. Each and every day, it changes all the time. That's not something that I can say is strategic or organised. It's really just a matter of: what do I feel brave enough to do today? 

“What do I feel brave enough to do today?”

And I mean, most of us don't have all those things figured out right? And that was at 30 and there are creatives and people who are in their early twenties who are freaking out about having everything sorted. 

I know. I mean, now I'm nearly 60 and it's still a process. The pressure that young people put on themselves to “make it” so to speak is so damaging. 

And you know, one of the things that I've been talking about a lot lately in the interviews that I do is something that David Lee Roth, the former lead singer of van Halen told me in an interview. I asked him what it felt like to be the world's biggest star in the mid eighties. Because he was, I mean, van Halen was the number one rock band in the world. And he said, “you have to be really careful when you reach the tippy tippy top of the tallest mountain because it's usually cold, you're almost always alone and there's only one direction.” 

And it really moved me because one thing that I've always, one thing I can say has been a fairly consistent journey for me is wanting to still be cognizant that my best work is in front of me, as opposed to behind me. And it's been one of the things that I tell my students when they're thinking about, you know, “making it” when you're in your twenties, big time making it as well. Do you really think you're going to be able to sustain that and evolve and grow that for the 40 years following your twenties? That's a hard thing to do. So my feeling is take small steps up the mountain and hope that you reach the mountain top the day before you die. 

“Take small steps up the mountain and hope that you reach the mountain top the day before you die.” 

I'm so glad that he passed on that story to you so that you could pass it onto us because I mean, I'm only 26 and I think about that sometimes. I'm like,” what if I achieve everything I want to achieve now and then what? What am I going to do? What am I going to have to look forward to?”

Hollie, I don't even think people really become fully conscious of who they are until they're 30. You know I've been talking about this a lot because I'm about to be 60. And the first 30 years of my life – zero to 30 – were just sort of practice version of being a human. What does it mean to be alive? What does it mean to have a consciousness? What does it mean to have desires and goals and ambition and talent and pain and heartbreak?  And then I would say the second 30, – 30 to 60 – have really been about creating this life, creating this journey. And I’m finally now, as I am well into middle age, beginning to feel like I know who I am. 

And I'm in a position where I'm looking at my family history. My mother is well into her eighties, my grandmother lived into her early nineties, her sister lived into her early nineties. So there's a lot of longevity. So I'm hoping that I follow suit and live till I'm in my early nineties which means I have another 30 years. And so I’m two thirds of the way through and now I'm thinking about, “well, how do I want to really spend my time? How do I want to only do things that really matter to me?” And, and now is when I think, okay, you know, the shit has hit the fan. I have now got to decide what is worth my energy and if not now, when and so forth. So give yourself a break. At 26, you're still in that embryonic stage. And really if for anybody that's in their twenties: be gentle with yourself, give yourself opportunities to fail without shame because that's the only way you're going to be able to experiment with the possibilities of your life. If you only do things that you know you're going to be successful at or that you know you're going to be able to master easily, then you're not, you're not striving for enough. 

“For anybody in their 20s – be gentle with yourself. Give yourself opportunities to fail without shame. Because that’s the only way you’re going to be able to experiment with the possibilities of your life.”
“If you only do things you know you’re going to be successful at,  or that you know you’re going to be able to master easily, then you’re not striving for enough.”

I think that's so good. It relieves a lot of the pressure for those of us who are earlier in our lives and our careers because when you think about it, those ten years in our twenties, like you say, are just one tiny sliver of the whole rest of our lives. So we don't have to put all that pressure on getting it perfect right? 

And you said that when you were in your twenties, you experienced a lot of rejection or “failure” throughout that stage of your career. I remember when you spoke at Webstock, which is where I first met you and first heard of you, your talk was about rejection and how those kinds of worst moments of your life can turn out to be the best moments. 

You spoke about how you had been sent a blog post where someone was trash talking you essentially, talking about your work and your career in a really not nice light. But instead of kind of letting that stop you, you joined that conversation and it led to so many kinds of great things in your life. How did that feel for you in the moment if you remember, and then were you immediately ready to dive in and join that conversation? Or was it hard at first? 

Everything is hard for me at first. I'm not one who goes into any new experience with optimism and joy. I’m very tentative about doing anything that I don't know how to do. I tend to be very resistant to change. I don't like to be in a position where I'm not in control of things although that's a bit of a sort of self-deluding concept because we control whatever we're in control of. 

And so, yeah, it was a super, super difficult time for me, very much a struggle. I struggled through trying to understand how to authentically contribute to a conversation that was about decimating my entire career to that point. But ultimately it was an experience that, while at the time felt completely demoralizing and shameful and humiliating, did become the catalyst for almost every important thing that came after. And so you don't really know what the purpose of something is until you experience it and, and really go through the entire experience. 

“You don’t really know what the purpose of something is until you experience it, and go through the whole experience.” 

You know, there are moments in my life where I was so consumed by heartbreak, I didn't think I would be able to survive it. And whether it be relationships ending, or this terrible experience back in 2003, discovering this sort of vitriol about me – those felt insurmountable. Now I look back on them and I think, “oh my god, if that relationship hadn't ended I wouldn't have found my true love or if I hadn't gotten fired from that job, the things that I have now would likely not be in the state that they are.” But you don't know that until you're through it. 

I'm not a particularly religious person, but I think I'm more on the spiritual side. And while I don't think that everything that happens has a purpose and a meaning, I do think that everything that happens leads us to the next thing that happens and we don't know what that will be. And so, you know, I think if anything, I’m proof that many, many bad things can happen to you but you can still emerge on the other side intact and stronger. 

“I believe that everything that happens leads us to the next thing that happens, and we don’t know what that will be.”

Amazing. And I think it's such a testament to you that even though it was so hard and awful to read those things about you, that you still joined that conversation. I mean you could have just ignored it, but then that's hard to not say anything too. 

So what made you decide, “no, I have to say something and I'm going to join in and do what I can to turn this around”

You know, at the time I was president of a branding consultancy that I had spent a good number of years building. And I was really worried that my staff or my partners would see this post on this website, Speak Up, and I wanted to ultimately, (cause it took me a while to decide, I think it took me about three weeks to decide to join in.) But I was being called a corporate clown, I was being called a she-devil, my work was called a pair of turds. And this was the Burger King logo and the Star Wars identity for Attack of the Clones. So I felt like I had to, if nothing more, defend the firm. 

But I did go in very disingenuously. I pretended it didn't really matter to me and it really did. But I also didn't want to be the hysterical female. I didn't want to seem overly emotional and like I was taking it too personally. I don't know what I would have done differently but I know I would've done something differently about that. I wouldn't have been so like, you know, “like this matters?” In fact it mattered more than anything at that moment. 

“I’m proof that many many bad things can happen to you, but you can still emerge on the other side intact and stronger.”

And like you said, the great thing about that experience is that it did lead to some incredible things in your life because you then started writing for that blog that had written those things about you.

I'm now the godmother to Arman's oldest child so who would have thought, you know? Life is a circuitous one and that’s sort of, I think the beauty in it as well. 

Debbie’s first book, How to Think Like a Great Graphic Designer

Yeah. So you started writing for that blog and then joined that team. You wrote your first book, and then you founded the graduate program in Branding at the School of Visual Arts. So I want to hear a little bit about that transition from doing the design, which you still do and have been doing, but to starting to teach branding and design. Was it doing that writing and sharing your expertise in that way that led you into teaching? What influenced that journey.

Well, I think I always wanted to be a teacher. When I was a little girl I would force my brother to be my student. I was so serious about it that my parents got me an attendance, ledger so that I could create all the names of all the students and then call the roll. And this was something that I spent a lot of time doing. I was so dedicated to this that my brother ended up skipping kindergarten because he knew everything he needed to know. He started to read and started to write. And he went straight to first grade because of how much I was teaching him. Which to this day is one of our great prides, you know, that I was able to do that. I mean, I don't know how well but I'm proud of it. 

So I always, I always felt like that was something that I wanted to do. I was teaching back in the nineties at FIT, fashion technology. And then I started teaching adjunct in the School of Visual Arts in 2006. And then Steve Heller approached me in 2007 about starting the Masters in Branding program. A program like that had never existed before so I was very excited about being able to create something from nothing and create the kind of program I wish that I could have had while I was coming up the ranks. 

It's a program that is focused on the various disciplines that really comprise branding. Branding is a combination of a whole slew of other disciplines: cultural anthropology, behavioural psychology, economics, business strategy. design. And so these are the tenants and the threads that we teach in the program. 

It's now 11 years old. We graduated 250 people and so many of them are making such a big imprint on the field. And I'm so proud of our students. We still have quite a lot of the founding faculty but are always growing and looking for new ways to incorporate thinking into the program. 

And it's been a big challenge over the last year as we transition from an in-person, on-site, intensive, 10 and a half month program to one that's now more global and online. And again, I went into that kicking and screaming, thinking there’s no way I’m stopping teaching and projectile crying, trying to master zoom and canvas. But now I'm really excited about it because I feel that teaching online, in a lot of ways, democratizes the process. You know, you don't have that hierarchy where students sit in the front and the back and the sides, you can see everybody all at the same time as long as you have your zoom screen set to 49 people. And we only have 22 people in the class, so it's great. 

And it changes the dynamics I think in a really positive way. And there are drawbacks in not being able to see people and physically engage with them face-to-face, but there's still a great opportunity in lots of other ways. So much so that we're going to be launching a hybrid program so that we can offer the opportunity to people that aren't able to come to the United States or can't afford to live in New York, to be able to still take the program and be part of it in a really meaningful way. It's been a really interesting time to rethink modalities of education and pedagogy. 

Yeah, that's incredible. I mean, I know I've looked at your program and there’s a Master's in Typography I looked at once and they’re all in the US and I was like, that's never going to happen, I can't do this. So it's incredible that these new ways of teaching and learning are coming to make it more accessible for anybody, wherever you are or whatever your circumstances are. It can become a little bit more approachable and accessible for everybody which is amazing, 

And you and your students have literally written the Bible on Branding! I love that title, I think it's amazing. And that is one of six books that you have published, soon to be seven. (I love that that's kind of a full circle from your English degree that you did English and now you are still doing the writing!) But do you want to tell me a little bit about your new book that's coming up? 

Absolutely. I would love to, I'm very excited about it. So the book is called Why Design Matters. It’s conversations with the world's most creative people and it is an anthology of some of my very best interviews that I've conducted on Design Matters over the past 16 years. And it is a coffee table book, it's 10 by 10, and it'll be 350 pages. So it's a big clunky book. It features beautiful photography that I've sourced from all over the world. 

One of the other things that happened with COVID was being unable to conduct photoshoots. Originally I was going to have three photoshoots in three cities and be able to take original photographs of my interviewers and interviewees over the years, bring them all together and take photos and that wasn't able to happen. So I ended up sourcing them, I became my own photo editor. But now I really was able to source some of the most magnificent photos ever taken of the people that are included in the book. 

So it includes about 60 interviews. It's organized into five areas, legends, culture makers, so forth. I'm really pleased with it. Roxane Gay, my wife, wrote the introduction, and I have essays by people like Tim Ferriss and Maria Popova and Steve Heller and Zac Petit – people that are really important in my life. And it'll be out October 26th. Hopefully I'll be able to do some online or potentially in-person events around the book. It's a, it's a book that really represents a lot of my life's work, so I'm very excited about it.

Debbie’s new book, Why Design Matters, features 60+ interviews from her award-winning podcast, Design Matters.

How incredible! Having all of those interviews together in one valuable piece is going to be amazing. And I read that you had also been filming a documentary, is that right as well? 

Well I was, pre-COVID. Adobe was working with me on a documentary to really show the journey of the book but unfortunately that couldn't be continued because I didn't do any photoshoots and I didn't have any meetings with the designer and my editor and so forth. So that didn't happen. Maybe I'll do a little promo of the book or something like that because that would be a fun thing to do. Actually, I think I'll approach Adobe and ask them if they would be willing to do that instead. 

Yeah. I think it would be amazing to see some of that because so many creatives love to see other creative processes. And I'm sure it's a cool experience to share that process too, of writing a book and bringing it all together. So hopefully you're still able to do something. That would be great.

Definitely, but I'm really happy with the cover and really happy with the design. I've been working with Alex Kalman, – Alex is Tibor and Maira Kalman’s son – so there's another sort of wonderful sense of the circuitous nature of life. Tibor Kalman was somebody that was so impactful to how I think about design, how I think about a career and the meaning of design. And then Maira Kalman, of course, is one of the great, great illustrators and artists of our time and somebody whose work I've been collecting for decades. So to be working with Alex, who's a great designer in his own right, is something that feels kind of miraculous. 

That's incredible. And, does it feature any of your own kind of illustrative work or lettering?

No. The only thing that is mine from a visual standpoint is the cover, which includes a scribble, a giant scribble, which represents the sort of circuitous nature of a conversation and a life and an idea, any journey. It’s one of my favourite things and we were able to get Harper Collins to approve that. So I'm very excited about it. 

One of Debbie’s books, Self-Portrait as Your Traitor, is full of illustrated essays and visual poems.

Yeah, that's great! 

I love to ask this question to everybody and I'm excited to hear your perspective, obviously having been through the process yourself of branding your own work and working with so many brands around the world, like Burger King and all of those amazing brands. 

What one piece of advice, if you can narrow it down to one, would you give to creatives when it comes to branding their passion? 

Well, I think that the term “personal brand” is a bit of an oxymoron. You know, brands are manufactured into things that people can draw and create with their imagination and with their ability to be innovative. They're not really real in the truest sense of real, you know? Brands don't have a consciousness, they don't breathe air, they don't have living, beating hearts, they don't bleed, they don't cry, they don't have souls or feel pain or pleasure. 

You know, brands very well may be the promise of an experience, but brands don't ever get to experience or reflect on that experience. So there's really nothing personal about brands other than the choice an actual person makes to accept or reject one in their life. People can own brands and they can create brands and they can direct brands but I don't think that they should aspire to be brands. I think that what is more important is to think about your character and your reputation and the work that you make and thinking about that in that way, for me feels much more personal than trying to create an impersonal brand. 

That’s a really great way to think about that. I think there is sort of that pressure or expectation to make a personal brand, so I like that way of looking at it as more of your character and your value and what's important to you and those sorts of things. So I love that. 

Thank you very much for sharing that incredible wisdom and expertise and for sharing your story with me. It's incredible to hear anybody's creative story and to hear their journey, so I'm very thankful and grateful. 

I would love for you to be able to tell the people where they can find you and what you would love for them to check out from you, if you would like?

Thank you, Hollie. Well, you can find me on my website, or on Instagram or Twitter at @debbiemillman – super easy. 

And we will all look out for Why Design Matters in October and we’re very, very excited. 

Thank you. Thank you. Thank you. I really appreciate it. Thank you, Hollie. Thanks for the great questions and great conversation. 

Anytime. Thank you so much. 

My pleasure. Good to see you again. So much fun!

Thank you so much to Debbie for joining me on this episode of Brand Your Passion – I LOVED this conversation and I hope you did too. It’s an honour to hear from someone with so much branding expertise, and experience as a creative themselves, so I don’t know about you, but I learnt so much from Debbie! 

You can see Debbie’s work and find all of her links at, and preorder her upcoming book, Why Design Matters, here!

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April 21, 2021


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