I try to stay technologically “fit” by writing software code. I know. A round on the elliptical machine, or even picking up Tae-bo (do people still do that?) or the likes might be a better use of time. But I guess I’m stuck in some of my old ways as I have been coding for over 30 years now. Woah. Where'd that number come from?

Writing code. Laying out a page. Cutting paper. Taking a photograph. Thinking out loud in text (as I am doing now). All of these tasks lie in the creative domain. You can do them, and do them, and do them. And you inch forward. You progress. And it feels quite nice because the immediate result is right in front of your eyes. Your hands did it. The materials obeyed your wishes. You have expressed yourself as you need to, in your own voice and without any intermediary. It’s an important kind of frame to keep in oneself, I believe, and that’s the reason why I try to stay fit in doing what can be done quickly — like coding — as a way to stay in touch with the agility of a directly expressed medium where high-speed iteration is the norm.

Leading people is quite different. Everything takes at least twice as long as you expect, if you are lucky. Iteration equals disruption. Creativity is construed as flakiness. So it’s no surprise to me that many people often ask me, “Do you still make your ... art?” They often say this with a pained look on their face. As if somehow what I do today ... isn’t what I really want to do. What underlies that question, of course, is the thought that, “Artists make art. Artists don’t lead organizations.” And it is that stereotyped thought, that resounds in literal stereo inside my head ... that makes my work as a leader for me, as an artist, extremely exciting and provocative as a direction in life. A direction that I feel fortunate to get to take.

Art is about finding meaningful patterns. Traditionally artists found these patterns in how we see and touch and feel. And then, artists found a role in how society feels and works, and found a means to broaden their scope of what their “canvas” might be. In 2013, the canonical example that everyone knows, of course, is Ai Weiwei. It’s not hard to think of the many others that creatively lead from within the domain of the arts and resonate outwards. However, it is much less common for artists and designers to lead institutions or organizations — but there are excellent examples out there like Mark Parker of Nike.

In the leadership domain, I’ve found some patterns that I have been finding meaningful to my developing journey as a creative leader. There’s the work of John Gardner. There’s the work of Gianpiero Petriglieri. And there’s the work of many leaders that I get the opportunity to watch and learn from up close. Actually, I started this post for a specific reason — I wanted to quickly document something I learned from Regina Dugan. Regina said something I hadn’t heard before ... to the effect:

“Most people think that when you take on a big, impossible goal with a team, that you immediately set yourself up for failure. That history will show that every time such a goal is marked in the sky, and a team is assembled, that failure is the common outcome. I, for one, have seen the contrary. That the more aspirational goal you set as a leader, the more likely that it gets done. Because the quality of the goal, determines who will join your team. And it is often the best people in the world that want to take on the most difficult challenges of our times.”

In other words, the quality of the challenge you choose as the leader, determines the quality of team that you get to create. Or, the quality of the challenge that you choose as a leader, largely determines the outcome. This is such an inspiring thought for me, and I’m so happy to get to share it with you. If you haven’t seen Regina’s talk on TED, I recommend that you do. And now back to the skies for you, and back to my treadmill routine of figuring out UTC time in Python for me. -JM

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