Debbie Millman on Taking Risks, Chance Encounters, Failure, Design & Avoiding Compulsively Making Things Worse…*

This past Tuesday, the online journal The Great Discontent published a deeply inspiring interview with the great Debbie Millman. Millman, a Renaissance-woman if ever there was one, is President Emeritus of AIGA, a contributing editor at Print Magazine, and Chair of the Masters in Branding Program at the School of Visual Arts in New York City. She also hosts the fantastic (seriously, check it out) podcast, Design Matters, the first weekly radio talk show about design on the Internet and has authored five books on design, including Look Both Ways: Illustrated Essays on the Intersection of Life and Design (HOW Books, 2009). Below are some of my favorite insights from the interview, which I strongly urge you to read in its entirety over on The Great Discontent.

Enjoy & rethink…*

“My first ten years after college were experiments in rejection and despair. I knew that I wanted to do something special but, frankly, I didn’t have the guts to do anything special. When I graduated, I didn’t feel confident enough, optimistic enough, or hopeful enough to believe that I could get what I really wanted. I wasn’t living what I would consider to be my highest self—in fact, I was probably living my most fearful self.”

{…}

“My whole life has been one thing leading to another, leading to another, and then another. It has been completely circuitous and mostly unplanned. Lately, I have been thinking a lot about these chance encounters: those elusive happenstances that often lead to defining moments in our lives. But what if one of those defining experiences never occurred? What if something wonderful, something that we have come to depend on, that serendipitous bit of luck that provided us with a big break or a big deal or the Big Time never happened? One of those “if I hadn’t been eating a gigantic McDonald’s breakfast on the 7am flight to Vancouver in the middle seat, I wouldn’t have apologized to the beautiful, elegant woman sitting next to me on the plane; we wouldn’t have started talking and I wouldn’t have found out she was an important editor of a cool design magazine; we wouldn’t have become friends and so on and so on” type of moments. I call this “six degrees of serendipity”—the quintessential recognition that if this didn’t happen, then that wouldn’t have happened, and we wouldn’t have ended up right here, right now, in this way.”

{…}

“A moment that I thought was a complete and total failure—this takedown of everything I’d done to date—ended up turning into the foundation of everything I’ve done since. I’ve just created a lecture titled “How the Worst Moments of Your Life Can Turn Out to Be the Best” because the worst professional experience I ever experienced turned out to be one of the most important professional experiences of my life.
I was really ashamed of all my failures for a long time. Now, I feel it’s important to share these experiences. I am hopeful that it can give other people hope and context to see things a bit differently. It’s not a failure until you stop trying.”

{…}

“Honestly, I feel like everything I’ve done has required some risk. I don’t think you can achieve anything remarkable without some risk. Risk is actually a rather tricky word because humans aren’t wired to tolerate it very much. The reptilian part of our brains wants to keep us safe. Anytime you try something that doesn’t have any certainty associated with it, you’re risking something, but what other way is there to live?

The first ten years of my career were very much organized around avoiding failure, but my inadequacies were completely self-constructed. Nobody told me that I couldn’t do something; nobody told me that I couldn’t succeed; I had convinced myself and lived in that self-imposed reality. I think a lot of people do this. They self-sabotage and create all sorts of reasons for not doing things under the misguided assumption that, at some point, they might feel better about themselves and that will finally allow them to take that risk. I don’t think that ever happens. You have to push through it and do it as if you have no other choice—because you don’t. You just don’t.”

{…}

“I want very badly to make a difference with my life. I’d like to make a difference by contributing to the world conversation about design.”

{…}

If you could give a piece of advice to a young person starting out, what would you say?
“I would provide five bits of advice:

Do not be afraid to want a lot.

Things take a long time; practice patience.

Avoid compulsively making things worse.

Finish what you start.

Often people start out by thinking about all the things that they can’t do. Once you take that path, it’s very hard to get off of it. Shoot high and shoot often.

{…}

“I feel happier and more a part of the world when I feel connected to others through likeminded communities. I feel really, really happy being part of a design tribe.”

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