For those of you who aren’t painters, I want to tell you this secret. To be a painter – even an amateur one like me – you also have to be a gambler. Painters have to be willing to lose, repeatedly, until a painting is finished.

Every time I make a painting, I reach a point where I must put everything on the line, bet it all on the next brushmark. And many times, I lose.

Now, I’m not a gambler in any other way. The only slot machines I ever remember playing were the ones I visited at the Las Vegas airport en route to the Grand Canyon. I didn’t win. Lottery tickets tempt me sometimes. But the potential jackpot is less compelling than the greater likelihood of losing. I’ve never considered myself particularly lucky.

Instead, I prefer a sure thing if I can get it. I am a creature of routine and sameness for this reason. I know what I like and try to maximize my chances. Maybe I just like control. Don’t most of us?

But painting is never a sure thing. It’s a practice of uncertainty and risk. Painting is always a gamble. 

The first brush strokes come with low stakes. There’s a lot less to lose when so little has been invested. But as a painting progresses, so increase the moments of possible ruin. With each new brush stroke, the razor’s edge becomes thinner.

Yes, mistakes can be corrected and even Bob Ross style happy accidents may add life to a painting. But I can tell you it’s not as easy to fix a painting as you might think, especially not if you want to preserve some precious part you’ve attached to. Changing one thing often creates a domino effect of other needed adjustments. This is doable. In fact, better paintings often result. But there is almost always something lost. And it is a gamble. The losses may never be recouped by the final bet.

When you look at a painting, there is typically no hint of the artist’s sweat, or that razor’s edge in view. You decide if you like it or not, and move on. You don’t see the paintings that have been tossed, scraped down, or sanded away, sometimes after countless hours of attention. But the artist remembers. The artist can’t separate the painting from the process of making it.

Maybe there are painters out there who don’t identify with what I’m saying at all. I’d love to know YOUR secret! And I’m aware there are ways of painting that make outcome more predictable. Still, I recently heard that Anne Packard once threw one of her paintings into the ocean. I know the struggle is real, even for great painters!

And I know the paintings I’ve wanted to throw into the ocean are often the ones I become most attached to. I don’t throw away the ones I don’t like. Instead, I let them rest where they taunt me until I have the courage to go back and try again. These are the ones I suspect others won’t value the same way I do; these are the ones that contain a bigger piece of my heart.

I don’t really like gambling. I hate to lose, especially in a contest with myself. I’ve had enough loss in my life already. But I am a painter, which requires me to be a gambler. I keep painting. Because sometimes I win. And only because I am willing to try again.

And sometimes I even understand: What is meant to be kept, can never truly be lost.

And sometimes I even know: we only find out what is truly possible, when we are willing to surrender everything we have attached to.

Are you a gambler? Are you willing to release the things that hold you back for the possibility of something greater?

Here are a few recent paintings that were saved from the trash.