How'd You Make That?

Three masterpieces, from glimmer through struggle to breakthrough.

- Adam Moss

James Joyce’s crayon edits of Ulysses.

FOR 40 YEARS, I was an editor, mostly of magazines, including this one. As an editor and as a reader, I found the story of how creators create irresistible. I liked that these stories had a classic structure to them—each inherently dramatic, starting with nothing and ending with something. I assigned a story on Stephen Sondheim in which he explained how he wrote a single song. I traced the evolutions of buildings and novels and soap-opera arcs. Cultural procedurals were especially good material. When I quit my magazine job, I decided to try my hand as an artist. It wasn’t entirely abrupt: In my work, I always found it satisfying telling stories in photographs and graphics and drawings, and in spare moments—a whim at first—I picked up a paintbrush to try making images myself. When I left my job, I began to paint more seriously. That was the beginning of my torment: I just wasn’t very good.

Decent paintings sometimes emerged, but they seemed almost by accident. And they were accidents I couldn’t necessarily re-create. I was conservative—if one part of a painting showed promise, I would protect it and put the rest of the painting at risk. Sometimes I could get something going and then tentatively feel emboldened to try something new and then fall back, and that would scare me—so I would retreat to what I knew, which meant resuming the bad habits. I got frustrated easily and gave up easily, never knowing when to persevere or surrender. You can see that these are all problems more of the head than of the hand (though there were plenty of technique issues as well). Basically, it all seemed impossible.