That feeling when you start playing it safe...
There's a particular feeling that comes over me sometimes when I'm painting. It's subtle at first—a slight hesitation before I make a mark, a little voice suggesting I should be more careful, a tendency to reach for smaller brushes and safer colors. Before I fully realize what's happening, I've tightened up. The joy has leaked out of the process, replaced by something that feels more like control than creation.
I've come to recognize this as caution creeping in, and it's taught me one of the most important lessons of my artistic practice: the very moments when I feel the need to play it safe are precisely when I need to do the opposite.
The Parallel Between Canvas and Life
The more I paint, the more I realize that what happens on the canvas mirrors what happens in life. When we feel uncertain or vulnerable, our instinct is often to protect ourselves—to make smaller gestures, to stay within the lines we know are safe, to avoid the risk of making a mess. It's a completely natural response. But in art, as in life, caution rarely leads us toward growth or authenticity.
Think about it: when have your biggest breakthroughs come? Probably not during the times you were playing it safe. The moments that shape us, that reveal something true about who we are and what we're capable of—those usually come when we're willing to be a little reckless, a little vulnerable, a little loose.
This is the ongoing journey I find myself on, both as an artist and as a person. It's not something you master once and move on from. It's a practice, a constant return to the question: Am I holding back right now? And if so, what would it look like to let go?
One Brush, No Safety Net
In this week's painting demo, I gave myself a simple challenge: use only one big brush for the entire painting. No switching to smaller brushes for details. No precision tools to hide behind. Just one brush, forcing me to work in broad strokes, to commit to gestures, to stay spontaneous from the first mark to the last.
It's remarkable how much one small constraint can change everything. When you remove the option to tighten up and fiddle with details, you have to trust your instincts. You have to make bold decisions and live with them. You have to accept a certain amount of wildness in the work.
And here's what I'm learning: that wildness, that looseness, that willingness to let things be imperfect—that's where my personal style lives. Not in the careful, controlled moments, but in the ones where I'm brave enough to be messy.
The Practice of Loosening Up
When I notice caution creeping in—and I always do eventually—I have a few strategies I return to. The one-brush approach is just one of them.
Sometimes I'll deliberately work in a different medium. If I've been tight with oils, I'll switch to acrylics, something that forces me to approach mark-making differently. Sometimes I'll pull out an old painting that didn't quite work and paint right over it. There's something freeing about working on a surface that's already "ruined"—suddenly you're not precious about wasting a good canvas, and that permission to mess up changes everything.
Often, I'll spend time in my sketchbook with absolutely no expectation for the outcome. Not every mark needs to be a masterpiece. Not every session needs to produce something worth sharing. Sometimes the whole point is just to play, to remember what it feels like to make marks for the pure pleasure of making marks.
These practices aren't just about producing better paintings, though they often do. They're about cultivating a mindset, a way of approaching both the canvas and the world. They're about building the muscle of letting go.
The Never-Ending Journey
I want to be honest with you: I don't think I'll ever fully "arrive" at a place where I'm always loose and spontaneous. This isn't a problem to be solved once and checked off the list. It's an ongoing practice, a constant negotiation between control and surrender, between intention and instinct.
Some days I paint with complete freedom. Other days I catch myself tightening up again, and I have to gently remind myself to loosen my grip. And you know what? That's okay. Maybe that's even the point.
Because every time I notice caution creeping in and consciously choose to work against it, I'm not just making better art—I'm practicing a way of being in the world. I'm learning to recognize when fear is trying to convince me it's just being smart or careful. I'm building the courage to take risks, to trust myself, to let things be imperfect.
And slowly, painting by painting, year by year, that looseness is becoming more natural. It's finding its way into my personal style, yes, but it's also finding its way into how I approach challenges, how I handle uncertainty, how I show up in my life.
An Invitation
So here's my invitation to you, whether you're an artist or not: Pay attention to where caution is creeping into your life. Where are you playing it safe when you could be playing it loose? Where are you reaching for the small brushes when you could grab the big one?
Maybe it's in your creative practice—your painting, your writing, your music. Maybe it's in how you approach your work, your relationships, your daily life. Wherever it is, consider what it would look like to do one thing differently. To add a little wildness back in. To give yourself permission to be messy.
Because here's what I'm learning: our most authentic expression—whether on canvas or in life—doesn't come from our most careful, controlled moments. It comes from the moments when we're brave enough to let go, to trust ourselves, to stay loose even when everything in us wants to tighten up.
It's a never-ending journey, this practice of letting go. But it's one worth taking.
What would it look like for you to loosen up today? I'd love to hear about it.