is an author, an educator, a brand strategist, and the host and founder of the first and longest-running design podcast,
Design Matters. As the former chief marketing officer at Sterling Brands, she worked with clients to develop some of the world’s most widely recognized brand identities and merchandise. She is the editor in chief of
Print magazine and the cofounder of the first graduate program in branding at New York City’s School of Visual Arts. She is president emeritus of AIGA and one of only five women in 100 years to have held the position. It wasn’t until her 40s that she began to realize and enact her full potential in her field. At age 54, Debbie continues to be a leader in the design world, both in discipline and in discourse.
Graphic Design USA named her one of the most influential designers working today.
Lisa: Tell us about the early part of your career.
Debbie: When I was in my 20s, I had no idea what I wanted. I knew that I wanted a lot, but I had very little encouragement or guidance as I was growing up, so I felt really inhibited about what I was both qualified for and entitled to. I didn’t feel that I was smart enough or capable enough or pretty enough or rich enough or anything enough to do much of anything. I mostly just fell into things and took almost whatever was offered, only because I was afraid that nothing else would come along. And so I would say the first ten years of my career in my 20s and into my 30s were experiments in rejection and failure, because I just kept trying to figure out what I was capable of and what I could do. It was a very tough, tumultuous ten years. I applied to a graduate program in journalism and I didn’t get in, and I applied to Whitney’s Independent Study Program and I didn’t get in, and so I just kept plowing along doing design.
When I was in my early 30s, quite by accident, while I was at a job at which I was very unhappy, I was contacted by a headhunter to work at a branding company. I was offered the opportunity to do sales, and while I didn’t really fancy myself a salesperson, or consider the possibility of a career in sales, I thought it was an opportunity to get out of the company I was in. I would also have an opportunity to learn about the world of branding, which I was really fascinated by. So I did that and at this point I was 31 or so, and I found that I was really good at selling branding. I intrinsically understood it and the motivations for organizations that were looking to rebrand in the fast-moving consumer-goods category. So by accident, I learned that I was really good at something I didn’t even know there was an opportunity to be good at.
I did that for two years and then the company was folded into another company, and it became very challenging politically. My boss quit and the creative director walked out one day, and it was really tumultuous. I called another headhunter and I asked her if she had anything that she could think of that I might be able to do. She thought I might do well at this little fledgling company she knew that had just come out of bankruptcy called Sterling. She hooked me up with the CEO, and we met and had a meal together. He told me about how he was trying to revive the agency, and I decided that I didn’t have much to lose. That was in 1995. I was 33.
Lisa: At 54, you are a star in your field. We sometimes assume that people who are stars in their field have always been stars, but you and I both know that’s not true.
Debbie: It’s not. It took me ten years after college to find my career path. And from there I really worked as hard as I could to make an impact. I was managing new business, marketing, and public relations. I worked harder than I ever had before, and for a period of time, I gave up much of my outside-of-work creative projects like painting and drawing and writing that had always been so important to me.
Lisa: That hyperfocus really paid off: three short years after you started there, you became the president of the design division at Sterling. At that point, some would say you had reached a pinnacle of success, but while this was all happening for you, you actually felt there was something missing from your life. Your career as we know it now hadn’t even begun yet.
Debbie: I had been focusing on this one path at Sterling and I started to feel like all I was doing was commercial work—that I wasn’t doing anything that was purely design, anything that was beautiful for its own sake.
I was trying really hard to get involved with AIGA and I’d felt a lot of rejection from them. Then in 2003 there was an article written about me in Speak Up by Armin Vit, which attempted to take down my whole career in branding. The article made fun of my work and trashed me and trashed the identities I had worked on—for companies like Burger King and Star Wars—and basically called me a corporate clown and a she-devil.
I was devastated. I was crushed by it. I was humiliated and embarrassed. I didn’t know if people at Sterling would find out I was written about this way and if it would hurt the company. I ended up writing into the forum (it’s still online to this day), to try and defend the kind of work that I was doing, and then the situation only got worse. I got torn down even further, but I tried my best to stay classy and not allow myself to be bullied, and also not to bully back. I stood my ground, and then a couple of weeks later, Armin wrote to me and apologized, not for thinking that my work was a pair of turds, as he put it, and which he told me he believed, but for the way in which I was bullied on the site.
I had never heard of blogs before that, and I thought that there was something really interesting about the idea of conversing in real time with fellow designers, holding them accountable, debating ideas and having a discourse. I told him that, and then he wrote me back and asked if I wanted to write for the site. And I quickly agreed and started writing for Speak Up that same year, and everything after that sort of snowballed. I started writing, and one of my pieces even went viral in 2004.
Lisa: So you began writing about design. That must have felt great to the part of you that was looking for something beyond work at Sterling.
Debbie: Yes, and then very shortly after that I was cold-called by a fledgling Internet radio network that was looking for me to host a show, but I very quickly realized they weren’t going to pay me. I actually had to pay them for the airtime, but at that point, as we’ve been discussing, I was really anxious to do something creative that wasn’t about selling work to clients. It was about ideas and discourse, and so I took the idea of writing about design in real time to talking about design in real time. I did that for a hundred episodes starting in 2005 until 2009. I did about twenty-five shows a year, paid to do it the whole time, and got better and better at it. I had no aspiration before doing it to be a radio host. iTunes had just taken off and I thought, Oh, let me put this up on iTunes, and by default it became the first design podcast. There were no design podcasts because there was no such thing as a podcast, so all of that happened very organically.
And then in 2009, Bill Drenttel asked me if I’d be interested in bringing the show to the Design Observer, and we got a new professional recording set up. I really started to take it even more seriously.
Lisa: Then you got an important call that led to yet another amazing opportunity.
Debbie: The Speak Up team of writers, as sort of this band of misfits, went to the AIGA conference in Vancouver in 2003. While en route to the conference, I met Joyce Kay, who was then editor in chief of Print magazine, and I told her about Speak Up. She came to one of our parties, and she invited me to participate as a panelist in a sort of live, on-the-spot event that she was doing as part of the How Conference the following year in 2004. There I met art director, journalist, critic, author, and editor Steve Heller. I invited him out to lunch. I told him that I was interested in writing a book and shared my ideas. He said that he thought my ideas were terrible and to keep working and coming up with better ones. Four months later, out of the blue, he referred me to a publisher who had offered him a book deal that he passed on and suggested they call me instead, and that was how How to Think Like a Graphic Designer, my first book and my best seller, came to be. Steve also asked me to create a Masters of Branding program with him at the School of Visual Arts. And then Emily Oberman called me to be part of the New York board of AIGA, and I served on the board for two years; then I moved to the national board; then I was asked to be the president of the entire organization. So every single thing that happened post-2003, I can trace back to that one forum on Speak Up. Every single thing.
Lisa: That is a perfect story of turning lemons into lemonade.
Debbie: It wasn’t even turning lemons into lemonade. It was turning lemons into lemon meringue pie! I think anything worthwhile takes a long time and requires working through the rejection and criticism. It’s almost impossible to have a career without ups and downs, and the more time you take to learn from your experience, the longer your career will last.
Lisa: In your late 30s and early 40s, all of these things outside of Sterling began happening, as a result of your perseverance and courage, that enriched and grew your career: writing, the podcast, your initial involvement with AIGA. You also took a class from design great Milton Glaser that inspired you to take all of those things and grow them with intention.
Debbie: Yes, that was in 2005. It was a summer intensive at the School of Visual Arts for midlevel designers and creative people who needed or wanted to reinvigorate their practice and their discipline. The class was all about declaring what you wanted for the next phase of your life. And so I came to the class really open and desirous of making this big leap to my next chapter. One of the last exercises in the class was to envision what you wanted your life to be like if you could do anything you wanted. I made this list of about twenty things I wanted that seemed really, really farfetched—big, fat dreams. And if I look at that list now (it’s been eleven years and it was a five-year plan), at the end of five years, I would say 60 to 70 percent of it had come true; at ten years, I would say 80 percent had come true; and at this point, probably 90 percent. And they were big dreams—not like, Oh, I wanna remodel my bathroom. It was, I want to rethink my whole life, I want to teach, I want to be part of AIGA in a significant way. So I went from wanting to be involved in AIGA to running the national organization within four years. I wanted to teach, and by the end of my five years, I was running a graduate program.
Lisa: Many women talk about getting more confident as they age, but you argue that while confidence is important, courage is more important. Tell us about that.
Debbie: I think confidence comes from a repeated effort that continues to go well. So if you try something and you are successful at it, you feel that if you do it again you will be successful again. And that repeated success breeds confidence. I think it’s actually more important to have courage, because you tend to be more afraid of doing things that you’ve never done before and through which you have no previous experience of success. Courage is m...