Closing the Gallery, Mike and Kathy Enter Their Freedom Season

by Anthony Kaauamo

“Don’t call it retirement,” Kathy Carroll said, repeating the advice a friend, Linda Kavelin-Popov, gave her. “Call it your freedom season.”

After twenty-three years of running the Mike Carroll Gallery, she and her husband are closing their doors, not to leave but to begin again. The phrase stayed with her because it fits. What they are stepping into is not an ending so much as a change in rhythm, a new season for two people who built a life, a livelihood, and a community around art. The building that held that story is part of it, but the heart of it has always been them: the risk they took, the work they made, and the island that became their home.

I am sitting with Mike and Kathy Carroll behind their home in his studio, a converted garage/ʻohana unit with a broad window that looks out toward the trees. Boxes are stacked in the corners. Rolled cardboard sleeves hold paintings that once hung on the gallery walls. Along one wall sits a row of hard drives, an archive of twenty years of work, mixed with pieces from a life before Lānaʻi, when illustration was still his living. The room feels both like storage and a beginning, a place that has been paused but not emptied. 

Twenty-five years earlier, they hadn’t planned to stay. They came to Lānaʻi in December 1999 for their twentieth wedding anniversary. Mike had just begun taking an oil painting class near their home in Chicago, revisiting the medium he studied decades earlier at Western Maryland College, where he double-majored in biology and art. For more than twenty years he had made a career as a medical illustrator, drawing surgical instruments and anatomical diagrams for textbooks and pharmaceutical ads. “You’re a pair of hands,” he said of that time. “They call and ask, can you draw this, can you do it by this time, for this amount?”

Their lives in Chicago were full but wound tight. Mike’s illustration work had become routine, defined by deadlines and precision, while Kathy worked in a large communications firm after managing transplant and clinical programs in the healthcare field. The anniversary trip to Hawaiʻi was meant to be a pause, ten days to rest. On the fifth day of that trip, they wandered into Lānaʻi City almost by accident. The quiet streets, the Cook pines, the slower rhythm all felt like another world.

They came across a small house that had been sitting empty for years. It needed work, but something about it stayed with them. By that evening, they were making an offer. At first the plan was simple, to fix it up as a vacation home and spend part of the year here. But each return lasted longer. By their fifth visit that year, the balance had tipped. They sold everything in Chicago, took two years off from their careers, and moved to Lānaʻi in January 2001.

On weekends they ferried to Lahaina to sell Mike’s paintings under the banyan tree, joining about sixty other artists in the Lahaina Arts Society. “You couldn’t just show up,” Mike said. “You had to be accepted.” They stood in the hot sun from morning to late afternoon, with visitors stopping by mostly to ask where the restrooms were. “I remember thinking, I’ve made the biggest mistake of my life,” Mike said. “We’d sold our house, we’d moved out here, and nobody even looked.” Then, just before closing, a woman stopped and asked if the paintings were for sale. She bought two. “It was like someone had handed us a million dollars,” Kathy said. Inside the historical courthouse where artists rang up their sales, they were told it was the largest first-day sale by a new artist in the group’s history. The next day they sold one twenty-five-dollar print, a sharp contrast to the sales they made the day before. “That’s when I realized it was going to be feast or famine,” Mike said. “But we knew we could do it.”

In December 2002 they opened their first gallery in the space behind Rainbow Pharmacy, formerly Island of Lānaʻi Properties and the Lānaʻi Visitor’s Bureau. Two years later, in 2004, they moved into the former Oyama’s Lānaʻi Family Store. Hirao and Kazuko Oyama had opened the store in 1952 under a lease from Hawaiian Pineapple Company. Hirao built it to match the historic architecture of the town’s early shops, sold furniture and televisions, and later ran VHS rentals, keeping the doors open for more than fifty years. When Mike and Kathy moved in, they became only the building’s second tenants. “We felt lucky to be part of that tradition,” Kathy said.

Life on Lānaʻi demanded patience and resourcefulness. Freight delays, slow seasons, and high costs were part of the deal. “Lānaʻi teaches you patience and resourcefulness,” Kathy said. “It is paradise, but it comes with a tax.” Much of the work fell to just the two of them and longtime staff like Diane Belez. “She was with us for eighteen years,” Kathy said, “We’d cinch our belts, cut back when we had to, and expand again when things picked up. Diane was always flexible.

In time, the Mike Carroll Gallery became the center of Lānaʻi’s small art world. Mike’s landscapes caught the island’s light and quiet, and his portraits became a record of the people who shaped it. Since 2003 he has been juried into every Schaefer Portrait Challenge, painting community legends such as Aunty Helen Fujie, Uncle Marco Eskaran, and Aunty Irene Perry. “I want to celebrate what people here do,” he said. 

One of those portraits was of Kathy herself, a nod to how their partnership shaped both the gallery and the island’s story. The painting shows her seated on a bench beneath trees, surrounded by cats, calm and steady amid the life she helped build through the Lānaʻi Cat Sanctuary, which transformed early trap-and-neuter efforts into one of the island’s defining community non-profits.

The gallery became another way the Carrolls supported Lānaʻi’s community, opening their walls to other artists and forms of work, including wood, textiles, ceramics, jewelry, and gyotaku prints—fish impressions made by artist Kristin Belew.

“For years [they would say], ‘You should buy the gallery,’” Kristin said, laughing. “Then one day Kathy just pulled us aside and said, ‘Hey, the business is listed for sale. If you want to think about it, now’s your chance.’”

“The first thing we thought of was just, I guess, being sad, right? That they were really doing it. Retiring,” said Kristin. “But that was the first serious thought of, like, oh man, what’s going to happen to this place? It’s so special. Where all of us are showing our work and just not having this icon that’s been there for so long.”

Mike wanted room to take risks again and return to large oil paintings. “I’m seventy-two now,” he said. “You start to see that light at the end, and I want to do some cool things before it gets me.” When the time came to think about what was next, they agreed on closing the gallery to focus on passions, but they wanted the gallery and space to continue in the right hands. They made the announcement over the summer and marked the change with an Aloha Bash Open House in August, a farewell and a welcome to the gallery’s next era: Deep Hawaiʻi Art, owned and run by couple Kristin Belew and Kacy Lorber.

Kristin came to Lānaʻi more than a decade ago as a scuba instructor and works as a captain for Lānaʻi Ocean Sport. She began experimenting with gyotaku a few years ago and over time her work entered the Mike Carroll Gallery. As her friendship with the Carrolls grew and they began planning to step back, Kathy asked if she and Kacy might want to take over the gallery. What had once been a lighthearted suggestion became a real conversation. After a dinner together, Kacy said, “All right, let’s do it. And ever since then, we never looked back.”

Mike now paints each morning in his studio at home, working through commissions and returning to larger oil pieces he never had space for before. Kathy plans to continue volunteering with the Lānaʻi Cat Sanctuary and serving on the Maui Humane Society board while helping at the new gallery one day a week. “For now, I just want to take a few months, go to the beach, and breathe,” she said. “After that, I’ll probably find another way to help, maybe something with seniors, since we’re aging into it.”

Their decision to stay, even without the daily demands of running the gallery, feels like the natural extension of the life they built here. They have watched the island change, seen new people arrive and others move on, but their sense of belonging remains steady. What they started will continue in new hands, in the same building that has carried generations of work and hope.

Deep Hawaiʻi Art Gallery will hold a soft opening in November, with its official opening planned for December.