Creative Leadership Insights from Debbie Millman

The all-new REACH Conference by HOW Events—November 13-14, 2017—will inspire and empower creative professionals by curating best-in-class leaders to share powerful knowledge that accelerates professional development. The world is a more complex place than ever before and the role of the designer is transforming to a position of business innovation, strategic differentiation, critical problem solving, and corporate leadership. REACH is an opportunity for creative leaders to have access to some of the most successful thinkers, doers and makers working today. Learn strategies, insights, and leadership skills to thrive in this challenging landscape.

Here, as the REACH conference approaches, the great Debbie Millman teaches us what it takes to make a difference in the design world:

What “non-creative” skillsets are most important to thrive in your current role?

I don’t think there is such a thing as a “non-creative” skillset. Any behavior or initiative or undertaking can be approached creatively. I try to approach both the things that I make and the things that I manage with creative energy that includes (on my best days, some days it is hard to muster it all) empathy, patience, thoughtfulness, generosity and kindness.

What advice would you give your younger self to accelerate your professional growth?

Do what you love, and don’t stop until you get what you love. Work as hard as you can, imagine immensities, don’t compromise, and don’t waste time. In order to strive for a remarkable life, you have to decide that you want one. Start now.

What are the characteristics of a good leader?

The world is a subjective place. There is no empirical definition of what makes something good; often only the test of time reveals whether it is or isn’t. Like art, opinions on greatness are varied and fierce. The quality of your work may very well be judged by those who aren’t schooled in the discipline, which can make for very challenging presentations or interviews. But showing a prospective employer the benefit you can provide can be far more effective than telling them how, and only a leader can do this with gravitas, panache, and meaning. The tenet to “lead by example” is the most widely accepted guideline for effective leaders, and it clearly makes sense. But it’s not the only principle worth following. The best definition of leadership I’ve ever read was written by the late great David Foster Wallace, in an essay titled “Suck It Up” from his book Consider the Lobster:

It is just about impossible to talk about the really important stuff in politics without using terms that have become such awful clichés they make your eyes glaze over and are hard to even hear. One such term is “leader,” which all the big candidates use all the time—as in e.g. “providing leadership,” “a proven leader,” “a new leader for a new century,” etc.—and have reduced to such a platitude that it’s hard to try to think about what “leader” really means and whether indeed what today’s Young Voters want is a leader. The weird thing is that the word “leader” itself is cliché and boring, but when you come across somebody who actually is a real leader, that person isn’t cliché or boring at all; in fact he’s sort of the opposite of cliché and boring. Obviously, a real leader isn’t just somebody who has ideas you agree with, nor is it just somebody you happen to believe is a good guy. Think about 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. If you’ve ever spent time in the military, you know how incredibly easy it is to tell which of your superiors are real leaders and which aren’t, and how little rank has to do with it. A leader’s real “authority” is a power you voluntarily give him, and you grant him this authority not with resentment or resignation but happily; it feels right. Deep down, you almost always like how a real leader makes you feel, the way you find yourself working harder and pushing yourself and thinking in ways you couldn’t ever get to on your own. In other words—and you have to suck it up and just ignore the clichés here for a second, because these aren’t just words, and there’s important stuff in back of them—in other words, a real leader is somebody who can help us overcome the limitations of our own individual laziness and selfishness and weakness and fear and get us to do better things than we can get ourselves to do on our own.

In thinking about your own leadership style, consider the following questions:

  • Are you more interested in being right or doing the right thing?
  • Can you admit when you are wrong and fight for what you know is right?
  • Can you take responsibility for your decisions, as tough as they may be?
  • Do you believe in what you are doing with your whole heart?

How do you thrive in complexity?

I try to avoid compulsively making things worse.

What professional development are you working on?

I am always in pursuit of awareness. Self-awareness, awareness of the world, awareness of politics, culture and innovation.

Where do you find personal inspiration to stay motivated and focused in your role? Any favorite reads, blogs, etc.?

I tend to walk a lot and get a tremendous amount of inspiration and new ideas when I am out and about. Designers who inspire me are Paula Scher, Emily Oberman, Marian Bantjes, Jessica Hische, Jessica Helfand, Paul Sahre, Brian Rea, James Victore. Artists who inspire me are Ed Ruscha, Richard Tuttle, Lawrence Weiner, Jenny Holzer, Sue Martin, Mike Kelley and the list goes on and on. I get infinite inspiration from my dogs. My bed inspires me

What skillsets do you feel are most important to succeed as a creative leader?

Every job is hard. Design is hard, marketing is hard, and working at McDonald’s and Starbucks and Walmart is hard. Why does it feel “easier” to do something we don’t love than to do something we actually feel passionate about? I think we lose our courage to pursue our creative dreams when we feel that the only way we can make a living is to conform. I realize now that making a living doing what you love requires a personal belief that you have something meaningful to contribute. What makes this particularly difficult is that making a living doing what you love doesn’t come with a real “rule book.” There is no single process for anything. In many ways, making a living doing what you love is an anti-process! For example, you may have a process for being creative, but the actual act of living creatively is organic and (nearly) involuntary: you have to do it—you have no choice—or a part of you dies. If you are considering settling because going after what you want seems too hard to do, remember that hating what you do every day is even harder. I guess this is a long way of stating that I believe one of the most important skills necessary to succeed as a creative leader is to, at all costs, avoid settling.

What would you consider one of the biggest challenges in the creative leadership role today? And what one piece of advice would you give someone new to this role?

The notion of a “vocation” has changed rapidly over the last two centuries. As recently as 150 years ago, most people didn’t consider happiness or fulfilling their purpose when considering their job. Most people were happy to have paid work in the first place, and they were grateful that they were able to provide for their families.

People hire other people and pay them in order to sell more products, communicate ideas better, move things off of shelves, to write code, to invent and innovate. But when you work for someone—anyone— you are essentially asking him or her to give you money to do that thing. That thing might be something that you love or went to school for or have deep interest in—or all of the above. The people that hire you (for the most part) are not interested in what you love or what your dreams are or what inspires you. The people who interview you are primarily interested in moving more products or communicating more clearly or winning an election or inventing new marketplace opportunities. Interviewers and employers expect a return on the investment of giving you money in exchange for doing what you were hired to do, and doing it efficiently and with zeal. To them, love has absolutely nothing to do with it. It takes work to get the work you love. It takes knowing how to interview well, how to communicate flawlessly, how to articulate your own purpose and to simultaneously do this while facing tremendous rejection.

Personally, I don’t take rejection particularly well and I tend to take it very personally and get very dejected with myself. This will lead to my wanting to abandon my efforts and to throw in the towel. But then I try to remind myself that I don’t know that anybody that really puts their whole self into something really feels any differently in the face of rejection. Why would they? Why should they? So my advice is this: If you want something badly enough in the face of rejection, you must keep persevering. Many, many, many, many people far greater than I have been rejected numerous times and many of those people have ultimately achieved real greatness in spite of (or even because of) the rejection. I don’t think rejection is ever final until you stop trying to succeed.


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