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What Should I Paint? With Gallery Director Jock

Written by Milan Art Institute | June 16, 2025

For over a decade, I have met artists from all different backgrounds and styles, and the one question that emerging artists always seem ask is, “What should I paint?” or, more directly, “What do people want to buy?”

Well, the good AND bad news is that I don’t know. Yes, I could tell you about the average client's aesthetic—the colors, sizes, and themes that a gallery might sell based on their region or demographic—but those answers do not address the question because it is inherently unanswerable by anyone other than you. The real question is, “What do I want to say to someone I might never meet?”

We are constantly looking for connection in life. Sometimes it’s a song that makes you dance, or a joke from a comedian that makes you think, “OMG, I thought I was the only one who noticed that!”

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My first year as a gallery director was at the Signature Gallery in Waikiki, Hawaii. The gallery had your usual “feel good” art you might expect to find on an island vacation destination: sunset paintings, whale sculptures, etc. However, we had one painter that had been dubbed “unsellable” by some art consultants.

Richard Oliver is a painter and musician from South Wales, UK. His figurative paintings did not fall into any familiar label or category (think baroque/gothic, or if Tim Burton painted as Margaret Keane).

I remember the first time we met, he talked for twenty minutes about one painting. He showed how he employed the golden ratio when making his compositions, and to me, each painting felt like visual poetry. A portrait might, on the surface, feel off-putting or sad with muted, somber tones. However, with a little backstory and introspection, the true impact was felt.

One afternoon, a group of ladies came into the gallery, and I began giving a tour of our artists. Sometimes people just want to look, and that’s okay; but these girls were fun—as sparkling and bubbly as the mimosa lunch they had just finished. They smiled at the sunset paintings and took pictures next to the six-foot bronze dolphin sculptures, until they reached Richard's section.

After a beat of silence, one of the girls spoke up, “What…is this?” Their Hawaiian rollercoaster ride just broke down in front of the haunted mansion.

I had grown to expect this type of reaction, and I learned the great responsibility a gallery director has to represent the artist properly. As I explained the stories, I could tell they could appreciate what he was doing, but their eyes started to wander to the bright and colorful underwater paintings.

And this one,” I said as I pointed to a painting depicting a beautiful woman on a beach, behind her a ship moored on the rocks, “This is Calypso. She longs for love, offering all of her affection and even immortality, but it slips through her hands like the sand beneath her feet.”

I read the page-long description the artist had left me, and just like that, the girls all looked to their friend, who fumbled in her purse while staring at the painting until she found her wallet.

You know the feeling you get when a magician surprises you with misdirection or the plot twist in a book makes you gasp? Well, the group of women I had been talking to were in town for a writers’ convention, and Catherine Bybee, New York Times bestselling author of over 50 romance novels, had just seen a painting that summarized the protagonist in her novels. She not only bought that original, but she went on to become a collector and good friend.  

Do you know why AI will never replace artists?  Because it cannot fall in love. Chat GPT will never feel the sting of heartbreak, experience the exhilaration of adventure, or know the strength it takes to bury a loved one. These are the building blocks of power artwork. These are the stories that fuse with paint and canvas to reach out and connect with someone.

Listen to your inspiration, be honest, do what moves you, and I promise, you will have answered the question of “what should I paint?”

Milan Art Institute Gallery Director

 

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