The Change That Changes You

I used to think good painting meant having a plan.

For years, I approached each canvas with a clear vision of where I was headed. My Coastal Waters series emerged from this methodical approach—paintings that captured light on granite, the weight of weathered cliffs, the particular blue-grey of Maine water. They're strong pieces and I'm proud of them.

But late last year, I wanted to take a fresh look and reimagine my practice.

The shift came from an unexpected place. When my wife Sonia and I decided to launch AICharmLab, I suddenly found myself in a world where I knew almost nothing—morning stand-ups where I was scrambling to understand basic concepts. Business decisions had to be made with half the information I wanted—conversations where I was transparently the least knowledgeable person in the room.

It was humbling in the best possible way.

In the startup world, you quickly learn that waiting until you understand everything means never moving at all. You make the next best decision with what you know, stay alert for new information, and pivot when necessary. What felt terrifying at first—this constant state of not knowing—gradually became energizing. Those gaps in my knowledge weren't obstacles. They were spaces where something genuinely new could happen.

I didn't expect this mindset to follow me back into the studio, but it did.

The first painting I started after months of startup intensity began in a whole new way. Instead of executing a predetermined vision, I found myself asking different questions. What happens if I discard all reference photos and paint entirely from my imagination? What happens if I follow where this brushstroke wants to go? What if I obliterate this section and start over?

Each mark became an experiment. Each color choice revealed three possibilities I hadn't considered. The painting—a wild explosion of flowers, painted completely from imagination—seemed to paint itself through me rather than being painted by me.

The paintings that emerged from this new way of working pulse with an unmistakable energy. Not because they're technically superior, but because they were born from genuine uncertainty. They surprise me because I couldn't have planned them. They feel alive because they came from a place of aliveness rather than a predetermined outcome.

In creating these paintings, I've learned that creative breakthroughs don't feel like success when they happen. They feel like barely controlled chaos, like being slightly lost but moving forward anyway, like trusting your hands when your brain doesn't know what comes next.

The startup taught me, and continues to teach me, that the most interesting solutions emerge when your usual tools don't fit the problem. You have to improvise and remain flexible, resourceful, and willing to be temporarily incompetent in the service of something larger.

Your best work—the work that only you can make—lives in the space between what you know how to do and what you're discovering how to do. It requires stepping away from the safety of proven methods and into the fertile uncertainty of not knowing what happens next.

4 Questions for Author and Creative Coach Pia Mailhot-Leichter