The Coin Flip Gallery: What Happened When Chance Picked My Paintings for Me

Every artist has a wall in the studio that nobody sees. Mine is the corner behind the dehumidifier where the 'not-quite-right' paintings lean against each other, faces out, like kids waiting to be picked for dodgeball. Some have been leaning there for three years.

When the folks at Riverbend Coffee offered me their back wall for a two-month show, my first instinct was the same instinct every artist has: play the hits. Show the crowd-pleasers. Hang the pieces that photograph well and sell even better.

Then I did something dumber and more interesting. I let chance decide.

The Rules of the Game

The setup was simple, almost insultingly so. Every finished painting in the studio—finished meaning I'd stopped fighting it, not that I loved it—got a number on a green painter's tape tab. Forty-three pieces total. Then I pulled methods of selection out of my own junk drawer:

• A twenty-sided die left over from a college D&D phase
• A mason jar of folded paper slips
• A 1976 Kennedy half dollar that belonged to my grandfather

Odd numbers came off the reject wall. Evens came off the 'safe' stack. Ties, gaps, and existential crises went to the coin. Heads meant the piece went up. Tails meant it stayed home, no appeals, no second-guessing, no 'well, actually.'

The whole selection process took about forty minutes. That's the part that should embarrass me. Forty minutes to do what I usually stretch across three weeks of agonizing, moving pieces around, holding them up to different light, asking my partner whether the blue one reads as 'melancholy' or just 'unfinished.'

The Randomizer Has No Taste (That's the Point)

Here's what a die doesn't know: that the painting of the rusted grain elevator in my hometown was the one a collector in Santa Fe almost bought. That the small portrait of my neighbor's dog once made a gallery owner in Portland say 'hmm' in a way I'm still decoding. The randomizer picked pieces with no résumés, no baggage, no history of near-sales and almost-shows.

And some of them were good. Genuinely, confusingly good.

The grain elevator painting made the wall. So did a small abstract I made during a bout of food poisoning, working in fifteen-minute shifts between trips to the bathroom. I'd never once considered it show-worthy. Hung at eye level under decent light, it held its own against anything I'd ever labored over. Maybe better. There's a looseness to it—a refusal to overthink—that I can't fake when I'm trying.

What the Coin Left Behind

The more revealing data, though, was in the cuts. The coin sent three of my 'safe' pieces home. One of them had been in every show I'd done since 2021. Watching it get tails'd was like watching a friend get voted off an island you're also competing on.

But standing in the empty spot where it usually hangs, I asked myself the question every artist avoids: was it in every show because it was my best work, or because it was my safest? Because I could defend it? Because it had already been validated and required no further risk from me?

I don't have a comfortable answer. I have a truer one: it was a habit. A painting that had accumulated so many frequent-flyer miles it became part of the furniture of my identity as an artist. The coin doesn't care about identity. The coin cares about heads and tails.

The Night of the Opening

The show opened on a Friday in March, in a coffee shop in a strip mall between a nail salon and a vacated mattress store. Not the Whitney. But forty-three pieces went down to twenty-two, and twenty-two went up, and here's what I noticed:

People lingered differently. The pieces I would have called my 'strongest' got polite nods. The weird ones—the food-poisoning abstract, a half-abandoned landscape I'd painted over twice—stopped people mid-sip. One woman stood in front of the grain elevator for a full four minutes, then bought it.

The piece I'd have bet on to sell? Still leaning behind the dehumidifier. Still waiting.

What I'd Tell You to Steal From This

I'm not saying fire your taste. Taste is the thing that took you ten years to build; don't hand it to a plastic icosahedron permanently. But taste has a shadow side, and the shadow side is fear wearing a beret. It calls itself 'discernment.' It says the loose piece isn't ready. It says the weird one isn't you.

So here's the assignment, if you want it: number everything. Flip something. Let a coin, a die, or a folded slip of paper make one decision you've been circling for months. It doesn't have to be a gallery show. It can be which track opens the album, which piece goes in the portfolio, which draft you send instead of polishing for another week.

You're not outsourcing the decision to randomness. You're outsourcing it to a version of yourself with no stake in the outcome—and that version sometimes sees clearer than the one clutching the paintbrush.

The show comes down in May. Two pieces sold, one commission came from it, and the grain elevator went home with a woman who'd never bought art before. As for the painting that's been in every show since 2021?

It's still good. But it's going to sit out a season. Tails is tails.