Lisa Henderling & Jay Dorin

October 2026 Issue

by Tamela Maxim
Photography (top) by Cassidy Dunn Photography

If you spend even five minutes with fashion illustrator Lisa Henderling and her husband, filmmaker/photographer Jay Dorin, you quickly realize you’re in the presence of two people who have lived several lifetimes’ worth of stories. Their careers—one rooted in elegance, color, and line, the other in adventure and documentary grit—couldn’t be more different. Yet together, they form a partnership that is equal parts creative, adventure-filled, and deeply devoted.

Lisa: A Life Drawn in Color
Lisa’s artistic path began in Queens, New York, just a short train ride from Manhattan. “Growing up in Queens gave me access to everything New York City had to offer,” she said. Her parents, former vaudeville dancers, assumed she’d follow in their footsteps. “I had absolutely no talent for the stage. At all!” she said, laughing. What she wanted, what she begged for, were art lessons.

New York’s free trade high schools changed her life. She tested into the High School of Art and Design, where half the day was academics and the other half was pure art immersion. “It set me on a career path at only 15 years old,” she said. From there, she attended the Fashion Institute of Technology, drawing live fashion models and learning from instructors who had the required minimum of ten years’ industry experience. “I learned how to draw the human figure and what worked in a fashion venue.”

During her early career, everything was entirely done by hand: pen and ink, watercolor, colored ink, and even cut Pantone film. “Pantones were sticky and clear,” she said. “You could overlap the colors and get different gradations.” She freelanced in Miami, walked into ad agencies with her portfolio, and landed jobs based on her unmistakable style. “They’d say, ‘We need an illustration of a couple on a boat having cocktails,’ and I’d do it.”

Everything shifted in the early ’90s when a young art director asked, incredulously, “You don’t work on the computer?” Lisa realized she had to adapt. What surprised her was how much she loved digital illustration. “I never wanted to paint, and I never liked mixing colors,” she said. Digital tools gave her the precision she craved. Even today, she sketches by hand, then scans and finishes her work digitally.

Her clients grew to include Macy’s, BIC, Snapple, Publix, Carnival Cruise Lines, Nordstrom, Kmart, and countless other well-known brands. She illustrated packaging, billboards, soda cans, game boards, magazine spreads, and so much more. “Some of my favorite projects were packaging,” she said. “It felt like I was part of people’s everyday lives.” A project she especially loved was designing a billboard for Macy’s to promote a new store in Florida.

Now living in Sun City Hilton Head, Lisa designs posters for the community’s 500-seat theater. She’s also exploring new ways to market her prints.

Jay: A Life Stranger Than Fiction
Jay’s path zigzagged wildly before landing in filmmaking. He first tried engineering but found the technical demands too much. He quickly realized engineering wasn’t for him, tried teaching high school shop classes for a bit, soon realizing he needed a different direction.

Then came Woodstock. Jay spotted a cameraman floating by in a rowboat, holding a 16-millimeter camera. “I looked at him and said, ‘Now this is a job!’” That moment changed everything.

Through a friend, he met filmmaker Mike Jackson and became a production assistant on a Time Life documentary. He learned camera work, sound, editing, budgeting—everything. Time Life later asked if he did still photography. “Of course I do,” he told them, then gratefully learned composition from their photographer when his amateur skills were revealed. “Another gift from the universe,” he said.

His documentary work took him around the world: Jamaica, Paraguay, to mountains, revolutions, and indigenous communities. “Sometimes the truth is stranger than fiction,” he said.

Lisa often gets asked whether he’s exaggerating. “I say, no, that really happened!”

Jay later wrote for Scholastic magazines, mentored by editor Bob Stine—later known as R.L. Stine of Goosebumps. After years of filmmaking and attending personal growth workshops, he became a guidance counselor for at-risk kids, specializing in drug and alcohol counseling at Miami Beach High School, and later as guidance counselor at Kingston High School in New York. “The file cabinet is full of thank you notes,” he said.

Now retired in Sun City, he serves as vice president of the table tennis club and runs a weekly ping-pong program for people with Parkinson’s. “The fortitude they have; it’s beautiful.”

A Partnership Built on Art & Heart
Lisa and Jay met at a workshop for couples, even though neither was part of a couple. Jay arrived in his coolest clothes. They were the only two single people there. She turned him down for a date that day, but Jay didn’t give up. He had a friend who was a yacht captain, so the next day he invited Lisa to go sailing. Despite some hesitation, she said yes. Their magical journey began, and they’ve built a sweet life across many places, including Miami, California, Oregon, New York, and now South Carolina.

Jay credits Lisa with generously providing love and support when his life hit some rocky spots. Lisa appreciates his extroverted qualities. He not only encourages and persuades her to step outside her comfort zone, but he’s also there when she asks for color advice. Their creative lives intertwine, each supporting the other.

Looking Forward
Lisa worries about the impact artificial intelligence (AI) has and will have on illustrators but believes luxury brands will continue valuing original hand drawn art. Jay believes in serendipitous moments that guide life’s path. Together, they continue creating, mentoring, laughing, and living boldly—proof that art and adventure can share the same home, the same marriage, and the same extraordinary life.

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Pink Magazine was honored to feature Lisa’s work on the July 2025 cover. You can learn more about her at
www.lisahenderling.com. To see more of her work and to purchase prints, search for Lisa Henderling by name at
www.inprnt.com.