by Lisa Congdon
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 beg
an 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 more important than confidence because it forces you to try new things, to move outside what is comfortable.
Lisa: You also say that every year you age, your life gets better.
Debbie: I had such low self-esteem for the first thirty years of my life and didn’t believe that I could have much of anything that I wanted. It was really, really important to me to try to fit in. At least if I had anything, it would be that I fit in. I’d think, At least I have a community of friends I can depend on. The older I’ve gotten and the more I’ve been able to depend on myself, I can see that I can take care of myself and be self-sufficient. I began to be less fearful about being my real self. Along with becoming braver in my career, I also came out as a lesbian at 50 years old. I started to feel even more open to the possibilities of my life.
Lisa: What advice would you give to older women who might be feeling fearful or stuck and are considering pursuing a passion, coming out of the closet, or changing their life in some significant way?
Debbie: Because of the way I was brought up, I felt very afraid of ever putting myself in a situation where I was vulnerable. If you are coming from that place in your heart, it’s very, very hard to do anything that requires confidence, courage, stamina, or persistence over the long haul. I think that if people want to do something they are afraid to do, it will likely stem from a place of not feeling capable.
And so my advice—and this is what I did—is to look at why you feel you can’t rely on yourself. Why do you feel that you won’t be able to do something you really want to do? What is the mindset that is creating that foundation of belief? And if you can work on that foundation of belief and why you feel that way, then from there you will find profound momentum. We often edit what’s possible for our lives before we even imagine what’s possible. We start to censor before we even dream.
Lisa: You have entered the last half of your life, and you’re thriving in a way that you didn’t in the first half. So what’s next for you? What gets you out of bed every day?
Debbie: The possibility that I can do anything. Once I faced having a finite amount of time left in my life, I began to think, I want to do everything I possibly can. Mostly I just don’t want to live with as much fear. I want to continue to feel like I can approach anything with an open heart and an open mind, and try my best not to let my fears and my pettiness or my small-mindedness stand in the way.
had never so much as stepped inside an art museum when she first picked up a paintbrush at age 76, even though her painting style was eventually compared to those of Henri Rousseau and Bruegel the Elder. She went on to become one of the United States’s most well-known artists, beloved for her primitive depictions of rural farm life.
Born Anna Mary Robertson in Greenwich, New York, in 1860, she received only limited schooling before leaving home at age 12 to keep house for a neighboring family. She worked as a domestic until her marriage to Thomas Salmon Moses at age 27. The couple eventually bought a farm and raised five children (another five died in infancy). After her husband’s death in 1927, she continued to live on the farm, now managed by her son, and eased into retirement, taking up embroidery, as she had never been one to be idle.
By age 76, arthritis had begun to make embroidery painful, so she turned to painting, creating detailed landscapes of farm life drawn from her own memories. “Grandma” Moses, as she had come to be known, entered her work (along with her jams and jellies) in the county fair, and the paintings were displayed at the local drugstore, where they were noticed and purchased by an art collector named Louis Caldor. Caldor was able to interest galleries in her work, despite the fact that, at age 79, it seemed unlikely to many that she would continue to produce more new work. Four years after beginning to paint, she had her first one-woman show in 1940 at the age of 80.
Riding a wave of interest in self-taught artists at the time, her popularity grew as she worked prodigiously—spending five to six hours every day painting at an old kitchen table. Outfitted in her iconic gray topknot, high frilled collars, and wire-rimmed spectacles, she became a midcentury pop culture figure, appearing in magazines and on television, but never changing her pragmatic outlook and plainspoken manner. In her words, “If I hadn’t started painting, I would have raised chickens.” She continued to paint nearly every day until her death at age 101, creating more than fifteen hundred canvases.
is most known for her 2008 return to the Olympic Games. She was 41 years old at the time, the oldest swimmer to ever earn a position on the U.S. Olympic Swim Team, and she won medals in every event she swam: three silvers. This was no easy feat, but it was also the third comeback of her competitive swimming career. She’d done it twice before—first, after a two-year break prior to the ’92 Olympic Games, and again in 2000, at the age of 33. She walked away with five medals that year, again, as the oldest swimmer on the team. Dara is the first and only athlete to swim for the United States in five Olympic Games. And she is one of only a few Olympians to earn medals in five different Games. She lowered her own American record in the 50-meter freestyle ten times, more than any other American—a record she broke at the age of 40, just sixteen months after giving birth to her first child. Since retiring, she’s written two books, including Age Is Just a Number: Achieve Your Dreams at Any Stage in Your Life. She currently tours the country as a motivational speaker.
Lisa: During your swimming career, you won twelve Olympic medals, broke your own record ten times, and earned so many accolades for being “the first,” “the oldest,” or “the only” that it’s hard to keep track of them. Looking back, how do you characterize your most significant accomplishment in swimming?
Dara: I don’t think I have just one! If you’d have asked me that when I was younger, I’d probably have given you a medal or a race and say this was it, but now that I’m older and I look back, it’s not really that. The journey it took to get there is what’s memorable for me, and what I learned about myself and what it took to be the best that I could be. Also, trying to balance motherhood and going after my dreams and goals has pr
obably been the most rewarding journey leading into the 2008 Olympics.
Lisa: So, you famously had not one, but three comebacks. What in particular inspired you to come back and compete in the 2008 Olympic Games?
Dara: There are many similarities between each comeback, and I think the main thing is that I missed the sport. You are a part of something your whole life and you go away from it, and there’s a part of you that just really misses it. I know that I personally missed the competition. I think even at my first comeback—I was going to be 25 back in ’92—I was considered really old for swimming. And I said to myself, All right, I’m older now, let’s do it! Each comeback had to do with missing the sport, loving the sport, falling in love with it again after I was away from it for a while, and also just trying something that no one had done.
Lisa: Speaking of that, in both of those games, in particular in 2008, you were the oldest swimmer on the Olympic team at 41. What was that like for you, in terms of your relationships with the other swimmers?
Dara: It was different because I was the same age or older than the coaches and trainers. I wondered if I would be like the mother hen or an aunt or big sister. Where would I fit in? When you’re on a team like that, there’s such camaraderie that you see the differences with, say, turning on the radio in the van on the way to practice and they want hip-hop and I want classic rock, or the fact that I can’t do nine workouts a week. I was doing five workouts a week, while they were doing so much, because my older body couldn’t recover. As far as community and getting along, I don’t think anyone treated me any differently. I thought, if anything, that I could help the younger ones if they had questions. It’s a great feeling trying to be there for the kids who look so nervous, just trying to talk to them. Maybe they didn’t have a good swim, or maybe they had a great swim—whatever the circumstances were—it was nice to know that I could be there for them if they needed me.