Debbie Millman is by all accounts not a failure. She’s president of design at Sterling Brands, host of a the Design Matters podcast on Design Observer, chair of the Masters in Branding program at the School of Visual Arts, and the author of several books. But she wishes that earlier in her career, she would have had more courage to fail, if failing had meant she’d pursued her original creative dreams.
Several years ago, Millman described these sentiments in an essay for Steven Heller’s book, Design Disasters: Great Designers, Fabulous Failure and Lessons Learned. “In thinking of the myriad failures I had experienced over the course of my life at that point, I decided to write about my biggest failure of all: my complete lack of belief in pursuing my original dreams,” Millman writes in her introduction to the essay. Now, she has hand-illustrated this essay, called “Fail Safe,” in a medley of mediums: color graphite, oil pastel, Sharpies, felt, metallic paper, newsprint, adhesive type, paint, tape, and rubber stamps that she bought from designer Louise Fili. She reads the text on the 80 pieces of art out loud in a video made with Adobe. Her narrative will resonate with anyone who has feared failure (read: everyone) or felt they’ve compromised their own creative dreams for security and stability.
What would Millman’s life look like now if she had, earlier on, pursued a path of creativity instead of security? “If I’d had more courage, I would’ve pursued a less commercial path,” Millman tells Co.Design, then drops what might be a shocker to her fans in the design world: “Maybe I would’ve gone into musical theater,” her passion in high school. “I could be a bit player on the Broadway stage.”
Does she really wish she had gone the starving artist route, painting (or musical theater-ing) in a garret by night and waitressing by day? “No,” she says. “I don’t regret the decisions that I’ve made. I really truly understand why I made them.” It wasn’t until several years ago that Millman finally started painting and writing again, doing more personal, hands-on creative projects that have meaning deeper than that of her commercial work. “One bit of advice I can give people is to remember that anything worthwhile takes a long time,” she says. “I’m now in my fifties, and it’s taken me this long to get to a point where I can create artwork or illustration work that feels more personal and meaningful.”
Young people might take comfort in learning that fear, that great blocker of creativity, is endemic even among the most successful creatives, as Millman points out: “Out of 21 great graphic designers I interviewed in my book, How To Think Like A Great Graphic Designer, all but two–Massimo Vignelli and Milton Glaser–said they experienced that sort of fear of being found out, or not being able to repeat their successes, or suffered impostor syndrome.” The route to successfully managing that fear is not necessarily confidence, which Millman calls overrated (“No one likes someone who’s really overconfident”), but courage, which involves feeling fear and saddling up anyway–and doing it now, not tomorrow, not in 20 years.