Struggle and failure are not problems

On Tuesday, my painting student apologized for not finishing his homework. He’s got lots of stuff started, but nothing finished. “Don’t worry about it,” I answered. “I’m in exactly the same place.”

I’ve been fired up about painting since I got back from Sedona in October, but I have nothing I want to show anyone—not my drawings, nor my paintings. I’m working on three things simultaneously this week. They’re slow going, in territory I’ve never explored before.

What painting is not

Painting is not performance art, but today we’re expected to post two or three new things on Instagram every week, or make reels where it looks as if we never stumble, stop to think, or throw down our brushes in irritation.

For most lines of work, productivity equals finished products, neatly packaged for sale. And if you never finished anything, art would be a pointless exercise. But painting is not linear, especially if you’re trying to grow. Alex Katz admitted to destroying a thousand paintings during his first ten years as a painter. Much of the real work of painting happens in the thinking and tinkering phase.

Contrary to popular thinking, struggle and failure are not problems. In fact, they’re a sign that something important is happening.

When we’re painting a lot and finishing little, it’s because we’re exploring. We’re testing ideas, pushing habits and breaking patterns that once felt comfortable. That’s messy, uncomfortable work.

What’s really happening

We’re training our eyes. We’re developing new visual language. We’re discovering which choices lead somewhere and which ones are non-starters.

I’ve noticed that when students are learning something new, they’re often temporarily worse than they were before. I like to frame that in terms of playing the piano. Pianists often learn the left-hand part and the right-hand part separately. When we put them together, it can feel like we can’t remember either part. It takes a little while for the whole to gel.

In painting, there’s a strong temptation to force work to completion just to prove that we’ve still ‘got it.’ But that is like practicing a musical part with the errors left in. It locks in old solutions precisely when we’re trying to leave them behind.

Slow-to-finish paintings are not evidence of failure; they’re evidence of risk-taking. We’re asking harder questions, and not settling for something that’s just okay.

Practice

There’s a reason musicians practice and athletes train. But, fifteen-minute painting-a-day challenges are no substitute for concerted, deep effort. Concert musicians practice up to 40 hours a week.

If your studio is full of half-resolved attempts but your brush is rarely at rest, don’t panic. Ask yourself:

• What am I learning right now?
• What am I testing?
• What feels uncertain—but promising?
• What needs work?
• Where do I want this to go?
• Why do I want it to go there?

My student in Trust the Process showed us this fortune cookie that she got right before class on Monday. It made me smile.

That class is full up but if you’re interested in How to see like a painter or Painterliness: Looseness and Bravura Brushwork, they’re registering now.

Registration is now open for workshops in 2026! Reserve your spot:

• Canyon Color for the Painter | Sedona, AZ, March 9-13, 2026
• Advanced Plein Air Painting | Rockport, ME, July 13-17, 2026
• Sea & Sky | Acadia National Park, ME, August 2–7, 2026
• Find your Authentic Voice in Plein Air | Berkshires, MA, August 10-14, 2026
• New! Color Clinic 2026 | Rockport, ME, October 3-4, 2026
• New! Composition Week 2026 | Rockport, ME, October 5-9, 2026

Can’t commit to a full workshop? Work online at your own pace:

Seven Protocols for Successful Oil Painters