“What we need to be able to instill in people is the courage to do something knowing full well they might fail.”

–Debbie Millman 

You may know Debbie Millman from her podcast Design Matters—the world’s longest running podcast on design—or from her six books, two of which are collections of illustrated essays and poems. Named “one of the most creative people in business” by Fast Company, Debbie is a fierce figure in the world of design. She gravitated to a career in design because she realized that greatness could be achieved through design and ultimately, that’s what grounds her work. We caught up with Debbie in preparation for Dribbble’s Hang Time Boston event this month.

Tell us a story about a creative team that you were a part of and something that helped that team thrive?

One of my favorite stories is from work I did years ago with Skywalker Ranch on the design of the merchandising for Star Wars: Episode II Attack of the Clones. We felt that it was somewhat miraculous that we got the job. I remember when we got to Skywalker Ranch we were so excited about the work we’d done that we were high-fiving each other in the parking lot. When you're working in branding and packaging, to be doing something for Star Wars felt like the ultimate.

When we started to show our work, we were met with this stony silence. It turned out the clients hated the work. At first, we did what most people do when their work is met with utter outright rejection, we tried to defend it. What I've come to realize is that there's nothing you can do to persuade someone they should like something they don't like. This is even true if you go to a department store and put on an outfit and the salesperson tells you that you look amazing, and you think your butt looks big. There's no commentary that can be provided by anyone to convince you that it doesn't.

We started to defend the work and then I realized in that moment it was not going to help. I stopped the meeting and said we’d come back in a week with different work because I sensed they didn't like it.

What that taught me, and the team, and this is something that I think ultimately helped us thrive, was that when you're having a meeting of any sort you have to anticipate every scenario. What will you do if the client likes everything? What will you do if the client hates everything? What will you do if the client picks the thing that you like least? You have to anticipate the unanticipated, you have to be able to visualize every scenario and plan what your response is going to be so that you’re prepared. I believe in relentless preparation. What can you do to prepare for every possible scenario?

Some people might push back and say, aren't you being pessimistic? But my perspective is, you're not being pessimistic, you're being realistic. If you anticipate every possible scenario, you are then prepared for every scenario.

“Courage is taking that first step without knowing whether or not it's going to be successful.”

You talk about the importance of storytelling and creating a narrative that unveils the inevitability of an idea, how do you help your teams and students to become these master storytellers?

I do this a lot with my students, when they're presenting their thesis, for example, they're not allowed to use notes. This terrifies them. Who you are and your ideas are as important as what you're actually presenting. If you don't know a concept deeply in your heart and in your soul, and if it's not in your DNA, then you can't present effectively. You can't present with PowerPoint slides with bullets of ideas. You have to present with visuals that you can talk about and that you understand so well it becomes part of your DNA. Part of being an effective presenter is knowing what you're talking about. Most people rely on notes, they rely on everything except having it thoroughly in their heart.

Years ago, my goddaughter, who was then in grade school (she's since graduated law school) was talking to me about things she was learning. She was stammering and having a tough time articulating her thoughts. She looked at me and said the most profound thing anybody's ever said to me, "Debbie, life is so difficult when you don't know what you're talking about."

For me that was it, it was like, okay, that’s the mantra for living. Life is so difficult when you don't know what you're talking about. Either don't talk when you don't know what it is you're talking about, or only talk about things that you feel passionately about and believe with all your heart. 

Why do you think that the world needs creativity now more than ever?

Because creativity and branding have finally become democratized. Design became democratized a decade or so ago. Branding has only been democratized in the last couple of years as a result of the politics we're experiencing. We started to see it a bit with the creation of the peace sign in the 70s—an emblem that signified values and vision for the future. We’ve seen, in the last three or so years, branding become democratized. Before it was solely used as a capitalist tool, as something to represent shareholder value; there was always a return on investment expected.

We've now taken the very tools of branding and created movements. We saw that with the logo that was developed after the terrorism in France—the mashup of the Eiffel Tower with the peace sign. We've seen it with the Black Lives Matter hashtag. And then what I consider to be the most significant brand that's been developed this year, which is the pink Pussyhat. There's no return on an investment that's needed, there's no P&L, this is a brand that has become a profound manifestation of the human spirit, and this excites me more than anything. People have taken the power of branding now into their own hands.

“You develop confidence after the successful repetition of any endeavor.”

What's something you're working on now with your personal leadership style?

I'm working with SYPartners as a Leadfully advisor helping people find and define their leadership skills. At the same time, I’m learning the SYPartners leadership tenants, which has been great. The way they’ve articulated leadership styles is fascinating. It’s about getting to know people through leadership and helping people find their inner leader. There's a big question about whether you're a born leader or you learn the skills to be a leader. And I'm very much in the camp of you learn the skills to be a leader, that everybody has an inner leader. It's been interesting and fulfilling to work with people as a leadership coach.

What have you learned from the way you’ve organically grown into a leader in the design industry?

You can't become a leader overnight. Leadership is a privilege. It's a lot of responsibility because you have to be accountable to the people you’re leading. A lot of people want promotions, and they want to be leaders, but once you become this leader you have a responsibility to everybody you're leading.

I think the greatest definition of leadership is one by David Foster Wallace from his book Consider the Lobster. Here’s a portion of it:

A real leader is somebody who, because of his own particular power and charisma and example, is able to inspire people, with “inspire” being used here in a serious and non-cliché way. A real leader can somehow get us to do certain things that deep down we think are good and want to be able to do but usually can’t get ourselves to do on our own. It’s a mysterious quality, hard to define, but we always know it when we see it, even as kids. You can probably remember seeing it in certain really great coaches, or teachers, or some extremely cool older kid you “looked up to” (interesting phrase) and wanted to be just like. Some of us remember seeing the quality as kids in a minister or rabbi, or a scoutmaster, or a parent, or a friend’s parent, or a supervisor in a summer job. And yes, all these are “authority figures,” but it’s a special kind of authority.

That, to me, is the ultimate definition of what leadership is and what a leader needs to be. Ultimately, who you are and what you believe is as important as your portfolio. You have to stand for something.

If you think back to Martin Luther King’s I Have a Dream speech, he didn't opinion poll or focus group that, he didn't go out and say, "What do you think about that statement? Do you think it's too nebulous? Do you think it's too surreal?" He spoke from his heart. Even somebody like Vince Lombardi, he's another person who I admire. His mission statement was, "I never lost a game." When people questioned him saying, but Coach Lombardi you did lose games, he’d say, "I didn't lose; I just ran out of time." I love that. That's another real tenant, that you don't see something as a loss, but as an evolution of growth and ultimately success.

“You can't wait for confidence to show up. You build your confidence over time.”

If you had a magic wand what would you do to design a world where anyone could build creative confidence to solve real-world challenges?

There's an inherent issue I have with the concept of confidence. I had a great conversation with the writer Dani Shapiro about confidence, and she said she felt confidence was overrated—everybody's seeking confidence. We’re often waiting for confidence to show up, and then once we feel confident we'll do whatever it is we want to do.

What I think is more important than confidence is courage. Because courage is taking that first step without knowing whether or not it's going to be successful.

What is confidence? I've deconstructed confidence and I believe confidence is the successful repetition of any endeavor. That's when confidence comes. When you know the next time you do it you're likely going to be successful. Most people that drive have car confidence. You don't start off having car confidence, you don't wait to have car confidence to start learning how to drive. You start learning how to drive and you’re terrified behind the wheel of this giant machine that could kill someone. Most people don't go and take their driver's test fully confident that they're going to ace it. They're nervous. You develop car confidence after the successful repetition of driving and not killing someone or crashing.

That's when you develop confidence. You develop confidence after the successful repetition of any endeavor. It comes after repetition. But the ability to try something new requires courage and that's far more important. What we need to be able to instill in people is the courage to do something knowing full well they might fail, they might be rejected, but it's only a failure if you accept defeat. We need to instill a sense of acceptance, try this, experience what it's like to do it. Success will come after the repetitive practice. It might take 10 years if you believe like I do in Malcolm Gladwell's 10,000 hours. That's what we need to instill in people. You can't wait for confidence to show up. You build your confidence over time.