Redpointing a Painting

*This article appeared in the June 2025 newsletter for the California Watercolor Association.

There is nothing like getting a painting right the first time around but we all know that’s just not how it goes. (This is especially true if I’m planning to enter a painting into a show when stakes are high and brushstrokes become tight!) If you’re like me you have stacks upon stacks of “failed” paintings just waiting to be gessoed over.

In rock climbing, the term “redpoint” means to successfully climb a route after multiple attempts, with no falls or rests on the rope. A good friend of mine, and fellow CWA member often tells me how I’m “so good at redpointing a painting”: that I can just keep painting the same thing over and over again until I feel like I get it just right.  I couldn’t help but laugh at the analogy – but she’s right! Redpointing a painting is definitely part of my process.  I have attempted some studio paintings three, maybe four times before I’ve landed on “the one.”

At first glance, repeating a painting might feel redundant—or even like a step backward. Shouldn’t every artwork be a fresh, new challenge? But for me, painting the same subject more than once is one of the ways I learn: I can test colors, techniques, and even mediums – often times, I’ll try a painting in watercolor and then in gouache! I also find that I’m able to refine my technique with practice, allowing me to apply paint more quickly and with confidence because I know exactly what I want to do and when the time is right, especially with watercolor. More importantly, with each attempt, I deepen my understanding of what’s important and what details I can leave out.