Wonder what it’s like to commission a piece of art?

Paul Wasn’t Even Looking for Art — and Then He Commissioned a Painting

What one collector’s experience taught me about how good this process can really feel.

Paul Caso showed up at the Union Street Fair for music, food, and a few drinks with friends. He wasn’t necessarily looking for art. And then he arrived at my booth, saw a wall full of octopuses, and came in.

That’s honestly one of my favorite things about doing fairs: the people who visit my booth that weren’t even looking for art. Because when someone stops by, not out of obligation, but out of genuine pull, something real is already happening.

The piece that caught Paul’s eye was already sold. Instead of shrugging and moving on, he turned to me and asked if I could make him a new one.

It Was Easier Than Paul Had Expected

This is the part I want you to hear if you’ve ever thought about commissioning something but talked yourself out of it: Paul said the whole process was easy.

Paul knew roughly what he wanted, which was an octopus with the same pose as the one in the sold painting, and possessing the same glimmer on the suction cups of the “arms,” and he wanted the overall artwork to be larger, with a darker background. He even sent me a physical frame so the new piece could hang in the exact same dimensions as a painting he already owned. That was basically it. We were aligned from our very first conversation. The price I quoted at the fair was the price he paid. He dropped off the frame, and in under two weeks, the painting was ready.

“You immediately got what I was looking for,” he told me. That’s what I’m always aiming for: to really listen, then go and make something that matches what someone sees in their mind, or something even better.

The Unveiling of Paul’s Art Commission

When Paul came to pick up the finished piece, I had it gift-wrapped. I love doing that. A commission is a gift, even when you’re buying it for yourself, and it deserves a special moment.

Paul told me that he got a little bit nervous unwrapping the art in front of me. I totally get that. There’s something vulnerable about opening custom art in the artist’s presence, especially when it was made specifically for you. What if it’s not quite right? What if you feel like you have to try to exude more excitement than you actually feel?

But here’s what Paul told me his initial reaction was: “I loved it. I immediately got it home and took photos of it and sent it around to friends. And everyone said, ‘oh, that is really cool!’”

That’s the moment I work toward. Every. single. time.

The Art Was Better Than Paul Had Even Imagined!

Paul had asked for a darker, simplified background. What he got was something a little more alive than that, with a deep, atmospheric quality, almost starry, like the octopus was floating in space. He didn’t ask for that specifically, but I steered it that way while I was painting.

“The background had more pop than I even expected,” he said. He calls the piece “The Cosmic Octopus.”

I ended up painting that octopus a few more times after the fair, since other people had fallen for the original too, but Paul’s commission is my favorite of all of them. Something about that particular background and that particular octopus came together in a way that I really enjoy visually. I’ve told Paul, and I’ll say it here: it’s one of the best things I’ve ever made.

Kirameki VII – Paul’s version

Paul’s Commissioned Art is Exclusive and Reflects His Personality

When I asked Paul if there was something about a commissioned piece that he would not have gotten from something “off the shelf,” he said this:

“I don’t really love just going to TJ Maxx and picking up a print that everyone else has. I like to connect to the artist and their work.”

Paul now has “The Cosmic Octopus” painting hanging in his living room in Montana, right next to another painting with colors that pair with it perfectly, and he told me that it stops guests in their tracks. It starts conversations. It also holds a special memory for Paul: a specific Friday afternoon, a fair, a group of friends, and a wall of octopuses he almost walked past.

“I’ll never forget stumbling upon it,” he said. “It’s a moment in time.”

The painting has become so meaningful to Paul that the octopus has turned into something of a spirit animal for him. He’s even thinking about getting his first tattoo based on it, and he’s asked me to draw it for him to take to the artist. I said “yes” immediately!

That’s not something that happens when you’ve chosen a print from a store’s shelf.

With an Art Commission, You Don’t Have to Know Exactly What You Want

One of the things that holds people back from commissioning art is the fear that they won’t be able to describe what they’re looking for. Or, that they’ll get it wrong, or the artist will get it wrong, and then what?

Paul had already seen a painting that he loved, so that’s what we worked from. But even if you come to me without a clear reference point, that’s okay. The conversation is the process. You tell me what appeals to your visual senses, what you want to feel when you look at your painting, and what it needs to live alongside. I ask questions. We figure it out together.

And sometimes, and OFTEN, actually, what comes back is better than what either of us was picturing (pun intended!).

If You’ve Been Thinking About an Art Commission…

I love making artwork for my walls, for fairs, and for the pure joy of it. But commissions are something different and wonderful. They’re collaborative. They’re intentional. They put a specific piece of you, your taste, your story, your space, into the work. And they give the artist something to work toward that has real meaning for both parties involved.

If you’ve been thinking about an art commission, I’d love to hear from you. Tell me about the space. Tell me what you love. Tell me what you almost bought once, but didn’t.

Let’s make something even better than what you were imagining!