A couple of years ago, I joined my friend Michael Tarnoff on the You and I Make a Thing podcast to create self-portraits in the style of Chuck Close. It was a challenge, not just in technique, but because I was learning Procreate for the first time. I had no idea what I was doing.

I fumbled constantly. I kept drawing on the wrong layers. But each mistake forced me to slow down and check in with the process. I wasn’t trying to be perfect. I was just trying to learn.

Michael fumbled too, but in his own way. He’s more of an abstract artist, and his self-portrait blended representation and abstraction in a way that was striking and beautiful. Watching his approach inspired me to loosen up. To be less rigid and more open to experimentation.

What surprised me most was that I didn’t get tired of looking at my own face. I thought I would. But the repetition became meditative. Detached, even. The portrait turned out recognizable, though filtered through a grid and a screen and a whole lot of guesswork.

Looking back, I realize I still carry that moment with me. I let myself fumble when I start something new. Because that’s where I need to be. Not polished. Not sure. Just present and willing to see what happens.

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