Stepping Out of Your Comfort Zone in Painting (Patreon)

I just returned from two wonderful painting retreats in Italy. Both were amazing, but something stood out to me. It is something I have seen often in my own painting journey and in others.

It was not the beginners who were the most timid. It was the more advanced painters. The group with more experience seemed far less willing to take risks, to try new approaches, or to accept instruction that felt unfamiliar. And honestly, I understand why.

When you have put in years of work, when you have struggled through the awkward stage of learning and finally reached a point where your paintings look good, you do not want to go backward. You do not want to be “bad” again.

But here is the truth. That fear of failure can trap you.

Many painters reach a comfortable middle ground. They are no longer beginners, but they are not truly progressing either. Their work stays the same year after year because they stop pushing themselves. And that is a shame, because the beauty of painting is that you never really arrive. There is always more to learn, more to discover, more ways to grow.

For me, that is what keeps painting alive. If I thought I had “arrived,” I think I would lose interest. What excites me is knowing that every step forward means risking some steps back. The path to better paintings always runs through bad ones.

Think of it like Michael Jordan. Every off-season he did not just practice his strengths. He identified his weaknesses and worked relentlessly until they became strengths. That is how he stayed at the top of his game.

Painting is no different. If you want to grow, you have to be willing to fail. You have to try new techniques, let go of control, and paint something ugly if that is what it takes to reach the next breakthrough.

I like to think of every “bad painting” as one more necessary step toward a good one. You cannot skip them. Every great artist you admire has stacks of unseen canvases they do not love, or paintings they wiped away entirely. You are not seeing their failures, but I promise you they are there.

So here is my encouragement to you.
Do not cling too tightly to what you already know. Do not be afraid of the “bad” paintings. They are not setbacks, they are stepping stones.

The best part of this journey is that we will never be done learning. That thought should inspire you, not discourage you. Embrace the process, embrace the failures, and keep pressing forward.

Because that is where the real joy and the real growth lies.

Now go get painting!

Your Paint Coach, Chris