I’m undertaking a 1000-day reinvention project, blogging here daily to track my progress. In Thursday Thinker, I share a smart idea or theory.
How does art emerge? Does a creator conceive of a painting, or an essay, in their head and then just get it down on canvas or paper? Or is it somewhat less controlled and more mysterious than that?
In their book Art & Fear: Observations On the Perils (and Rewards) of Artmaking, David Bayles and Ted Orland write:
Control, apparently, is not the answer. People who need certainty in their lives are less likely to make art that is risky, subversive, complicated, iffy, suggestive or spontaneous. What’s really needed is nothing more than a broad sense of what you are looking for, some strategy for how to find it, and an overriding willingess to embrace mistakes and surprises along the way. Simply put, making art is chancy—it doesn’t mix well with predictability. Uncertainty is the essential, inevitable, and all-pervasive companion to your desire to make art. Ane tolerance for uncertainty is the prerequisite to succeeding.
I started a new painting yesterday, one to go with an essay I have in progress, about a brief relationship I had in fall of 2014. I wrote about this essay a bit yesterday in my blog post about conscious and unconscious desires in story.
The direction the essay is taking has surprised me, as it is very different than where I thought I was going when I started it. I thought I was writing about the tendency people have to label other people with DSM-5 disorders: narcissism or sociopathy or borderline personality disorder. And I was going to write about lately how attachment styles have seem to have taken over at least some of the Internet discourse about when other people fail to respond properly in relationships. The key, I was thinking, the key to the glass house (the tentative title of the essay, what law professor Graham gave me) was a reality check: often relationships don’t work because the other person just doesn’t like you that much, not because that person is a narcissist or borderline or because they have avoidant attachment style.
But as I wrote it and then conceived of a painting to go with it and pondered false and true goals in my story, my thoughts about what I wanted to say have changed. I started wanting to write about how Kat, Graham’s ex-girlfriend, was actually a role model for me though I didn’t recognize it at the time. Not only was she not a narcissist or borderline, she was a hazy suggestion for where my life might go, where it could go if I only let go of this all-consuming desire to repartner. She pushed back on Graham’s wish to spend all his time with her, to get married, to insinuate himself into her daughter’s life. She told him she only wanted to see him a couple times a week, not every night like he wanted. She told him to get control of his drinking. And eventually she left him, and moved out of state.
I didn’t expect the essay to go in this direction, but it’s a welcome surprise.
I started a painting called Cat Lady—or maybe Kat Lady— to go with the essay. It is just a big portrait of an abstracted cat, painted with bold colors and obvious brush strokes. It is definitely risky to me as it differs so much from my other paintings in the series and my painting in general. It’s also risky because I’m moving more into the realm of the representational. But it’s exhilarating too to do something so different.
The painting exists hazily in my imagination as a combination of an abstract painting of a cat I found online, a photo of my own cat in which she looks regal and haughty, a color scheme I picked out to express what Graham told me about Kat, and an understanding of how I typically paint.
I’m excited to see how it progresses, because, to me, a painting that has been realized is far more interesting than what I can imagine.
Bayles and Orland write:
Imagination is in control when you begin making an object. The artwork’s potential is never higher than in that magic moment when the first brushstroke is applied, the first chord struck. But as the piece grows, technique and craft take over, and imagination becomes a less useful tool. A piece grows by becoming specific.
The specificity of a painting as it develops—or an essay as it goes through multiple revisions—is one of the most exciting aspects of working as a creator. I had one of my Things Men Gave Me paintings accepted into a show. It’s a piece that turned out very different from what I imagined when I started it.
The specifics of it are what make it good: the strange color scheme of light blue against dark greens and reds, the scribbled out secondary wine glass behind the primary one, the scratchy writing along the left side and the bottom.

I’m so excited to experience how Kat Lady becomes specific.
As I develop skills in painting and writing, my art gets better, and it also becomes more distinctively my own. Making good art is not simply a matter of talent. It is about skill. But it’s also about being willing to express yourself fully and vulnerably in your art.
Bayles and Orland take as a primary assumption of their book that “artmaking involves skills that can be learned” but artmaking is not just about skill, they write:
The conventional wisdom here is that while “craft” can be taught, “art” remains a magical gift bestowed only by the gods. Not so. In large measure becoming an artist consists of learning to accept yourself, which makes your work personal, and in following your own voice, which makes your work distinctive.”
Following your own voice is risky. It feels scary. Most pieces you paint or write or otherwise produce won’t be notable and won’t get any recognition. But you keep doing it, if you’re driven to be an artist.
It’s that drive to make art that matters, not pure talent. If you can’t stop making art, you will do it over and over again, developing both skill and voice as you go. “You learn how to make your work by making your work,” write Bayles and Orland.
Art emerges from the work of an ordinary person, one with flaws and weaknesses:
The flawless creature wouldn’t need to make art…. If art, is made by ordinary people, then you’d have to allow that the ideal artist would be an ordinary person too, with the whole usual mixed bag of traits that real human beings possess. This is a giant hint about art, because it suggests that our flaws and weaknesses, while often obstacles to our getting work done, are a source of strength as well. Something about making art has to do with overcoming things, giving us a clear opportunity for doing things in ways we have always known we should do them.
So: art emerges unpredictably, driven by imagination, shaped by an artist’s voice and skill, and tempered by that artist’s flaws and weaknesses.
I’m writing this today having shared my art more widely yesterday. I feel vulnerable and exposed, but exploring the reality of making art and how it gets created has helped me feel a little less scared.