The Ugly Middle: Pushing Through the Messy Part of Creativity

Let’s talk about the “ugly middle”—a stage in the creative process that has haunted me for years. I first recognized it in my Hollywood studio, across from the Hollywood Forever Cemetery on Sunset Boulevard. It was a beautiful, light-filled space where I was deep in the early years of my painting journey, stumbling through chaos and uncertainty.

Looking back, I realize my first decade of painting was about finding my voice—without art school, critiques, or guidance. I had jumped straight into commissions, selling through galleries without fully understanding how to develop a painting. Every piece hit a wall where I thought, This is awful. I don’t know what I’m doing. Maybe I should stop. More often than not, I did.

But over time, 25 years in, something shifted. I realized the ugly middle never disappeared. Every painting reached a phase where it felt wrong, chaotic, or completely lost. My instinct was to paint over it. Yet, if I stayed with it, something unexpected could emerge.

Eventually, I stopped fearing this phase. I saw it as a necessary transformation—not just in painting, but in life. We’re all navigating broken systems and uncertain paths, and the ugly middle is where real progress happens.

Now, when I hit this phase, I step back and shift my perspective. I change the brush size, introduce an unexpected color, or get closer to the part of the painting that frustrates me. The breakthrough often comes right after the hardest moment.

The ugly middle isn’t failure—it’s growth. It’s where my voice develops, where the real questions arise: What brought me here? What can I learn? Instead of abandoning the work, I let curiosity take over.

If you’re in the ugly middle—of a painting, a project, or life—stay with it. Keep pushing. Let the process guide you. What’s waiting on the other side might surprise you.