Art & Fear: Observations on the Perils (and Rewards) of Artmaking is the best book I know about the artist mindset. One of its central ideas is that artists often stop growing because they become attached to outcomes: approval, consistency, or the need to avoid failure. Artists also gravitate toward what gains them positive feedback.
There’s a moment in every painter’s development when things start to work. Drawing is competent, values are accurate, color is no longer embarrassing. People compliment your work and some of it sells. You’ve arrived.
Beware, it’s a trap.
It’s comfortable. You know how to solve most problems before they arise. You have a reliable process. Your paintings look like paintings. And because of that, it’s dangerously easy to stop pushing. After all, why fix what ain’t broke?
The problem is that technical proficiency, while necessary, is not the same thing as having an artistic voice. One is about solving visual problems. The other is about saying something that only you can say. They are very different goals.
You can be very good at painting and still produce work that feels generic. You lean into what you know works: safe compositions, familiar color harmonies, predictable brushwork. Over time, your paintings become polished, and interchangeable with so many others.
Hitting this point is an achievement, but it doesn’t mean you’ve arrived. Sadly, some never move beyond it. The way out isn’t more polish—it’s more risk.
If you’re ready to push past technical competence and start developing a stronger, more personal voice, I go much deeper into this in my advanced workshop in July. It’s all about voice, although we will discuss technical issues.
You do you
An artistic voice means making decisions that aren’t strictly right (but based on a knowledge of the rules, as I mentioned last week). It means aggressively editing reality and choosing colors based on harmony, not because they’re really there. It means moving beyond the safety net and allowing yourself to fail.
I’ve watched many technically-proficient painters refuse this jump. They’ve worked so hard to minimize mistakes. Now I’m suggesting they reintroduce uncertainty. That feels like regression, but it isn’t.
Technique is about control. Voice is about intention. Without control, your intentions can’t be executed. But without intention, control is empty.
You can see this clearly when you compare paintings that are ‘correct’ with those that are compelling. The former check all the boxes—accurate drawing, believable light, competent handling. The latter might bend or even break some of those rules, but they carry conviction. They feel authored.
How to escape the ‘good enough’ trap
Start by noticing where you’re playing it safe. A little voice in your head will be saying, “but this might not work.” Do you avoid subjects because they’re too hard? Default to the same compositions? The same color harmonies? Those patterns are clues that show you where you’ve built comfort, and where you need to push.
Paint something you don’t fully understand. Exaggerate values. Simplify more than feels comfortable, or complicate something you normally simplify. The goal isn’t to make a masterpiece. It’s to stretch your decision-making beyond autopilot.
In the end, good-enough painting isn’t a technical problem. It’s a creative one. And the only way through it is to risk not being good enough—for a while—until you push yourself into greatness.
Registration is now open for workshops in 2026! Reserve your spot:
- 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: