The Art of Regret: What I Wish I’d Done Differently

We’re told to “live with no regrets.” But let’s be honest—that’s a lovely sentiment and a terrible strategy. Regret is part of being human, and it’s certainly part of being creative.

For many artists, regrets don’t come from what we did. They come from what we didn’t do. The sketchbook we left untouched for years. The opportunity we passed up because we didn’t feel ready. The time we let someone’s offhand comment get into our head—and stayed there far too long.

These regrets creep into quiet corners:
“I wish I’d started sooner.”
“I wish I hadn’t listened to them.”
“I wish I’d believed in my own style before I diluted it.”

They’re not failures. They’re markers—reminders of who we were and how far we’ve come. And while regret stings, it also instructs.

The Missed Chances

Some of us regret not applying for that grant, submitting to that show, or following up with that gallery. Maybe we were too afraid. Maybe we thought we weren’t good enough yet. Maybe we were just tired.

Looking back, we realise those moments weren’t about lack of skill—they were about lack of confidence. And that hurts in hindsight. But it’s also a guide: when a new opportunity comes, will you shrink again? Or will you remember the weight of hesitation, and try anyway?

The Wrong Roads

Regret also comes from choices we did make—sometimes out of desperation, sometimes because we didn’t know better. Underpricing work. Accepting exposure instead of payment. Spending months on commissions that drained all the joy out of creating.

At the time, they felt necessary. But now, with distance, we see what they cost. And that insight is fuel. It helps us set better boundaries, raise our prices, protect our time, and recognise the difference between an opportunity and an obligation.

The Silence

One of the deepest regrets many artists carry is the years of silence—the seasons where we didn’t create at all. Life got in the way. Confidence eroded. We convinced ourselves that creativity was indulgent or unimportant. And then came the ache: that slow, haunting sense of being disconnected from something vital.

The good news? Picking up a brush, a pen, or a camera after that silence is more powerful than never putting it down. It takes courage to begin again. And it’s never too late to return to the work that calls you.

Regret Is a Mirror, Not a Sentence

We don’t talk about regret enough in the art world because it’s messy. But when we push past the shame, regret becomes a mirror. It shows us where we lost faith in ourselves. And more importantly—it shows us how to regain it.

You are allowed to regret. And you are also allowed to grow.

Whether it’s a project you never finished, a piece you sold too cheaply, or a voice you silenced for too long—those regrets are part of your story. But they don’t get to define the ending.

They get to inform your next step.

So here’s your invitation:

What do you regret—and what has it taught you?

Share it. Talk about it. Not because we need to dwell—but because someone out there needs to hear that they’re not alone. That missteps don’t mean you’re off the path. Sometimes, they are the path.

Let’s make space for honesty in the creative process. Not every brushstroke is bold. Some are hesitant. And some, yes, are filled with regret. But together, they still create something worth seeing.