Holly Pisaturo’s classroom looks different from most. And that’s no accident.

“What’s the thing that will make it so cool it will bake in the difference?” She asks herself this when designing each new lesson. That kind of purposeful creativity is exactly what sets her apart and helped earn her the honor of Sarasota County’s Middle School Teacher of the Year. 

Pisaturo thinks intentionally about what will best ignite her McIntosh Middle School art students’ curiosity. Her room reflects that mindset: soft lighting, collaborative seating, and shelves lined with tactile artwork arranged in small thematic vignettes. Each display invites students to touch, explore, and reflect, offering windows into cultures and perspectives beyond their own, including pieces inspired by Africa, geodes, Georgia O’Keeffe, Native American pottery, arrowheads, and more. 

Pisaturo’s life began in Ohio. The youngest of four children, she moved to Sarasota after graduating from Youngstown State University, following her parents south with a strong hunch that she would someday need to care for them. This instinct to stand in someone’s corner began early. By 17, she was a cheerleader, a cheerleading adviser, and an after-school instructor teaching calligraphy, tie-dye, and cheer — roles she continued through college. 

She was a full-time mom when she started substitute teaching at her children’s school, a job that led to a permanent position. The job wasn’t an exact fit for her, so she stepped away, ran her own jewelry business, and eventually returned to substitute teaching. Even while pursuing other paths, including serving as director of volunteers at The Hermitage Artist Retreat and as an after-school program director at Tuttle Elementary School, she remained tied to the arts. The pull of education persisted, and two years ago she joined McIntosh Middle, where she now feels a deep connection to both the students and the school.

“In middle school, I get to teach all of it,” she said. “Middle schoolers are hilarious. It’s not always the calmest day, but they’re funny, smart, and they can make some art.” 

In fact, her students are creating extraordinary artwork, much of it displayed in the hallway outside her classroom. Many pieces resemble high school–level work; watching Pisaturo teach makes it clear why. During a recent visit, she instructed students on how to make paint from items found in their yards or kitchen cupboards. On her own time, she prerecorded videos demonstrating how to mix the paints and apply stroke techniques to create richly colored images. Students were fully engaged, and Pisaturo moved from desk to desk offering direction, encouragement, and praise. 

Recording the process serves several purposes. “When I present a project, I walk my students through the creative process I went through, with funny theatrics of any fails,” she said. “It’s important to show them both the awesome successes and the ones that didn’t quite work as planned, what I did to correct it, and that it’s OK to mess it up the first (or fifth) time.” 

These teachable moments are part of why Pisaturo was recognized as Teacher of the Year. When the announcement was made during a surprise assembly, the band played and the cheering from students was deafening. “They were over the moon,” she said. “We’ve got great kids here. Even kids I hadn’t had in class were excited.”

The mother of four and grandmother of two was joined by her husband at the celebration. Her son, recently deployed to Iraq, has been serving in the Army for the last five years. Her family made the day special, she said. “My husband emailed everybody on the planet, and they all watched the news. They’re all still bragging about it.”

When asked what sets her apart as a teacher, Pisaturo didn’t answer in her own words. Instead, she shared the notes she received from students. “After the assembly I got beautiful letters about how I work with every single student, how patient and kind I am, how I take time,” she said. “Letters from the heart.” 

Pisaturo teaches far more than art. She elevates students into leadership roles by assigning them as classroom teaching assistants and collaborating with departments such as art, culture, and climate. “They make gifts, cards, and products, and I see them lifted in those positions,” she said. “They have confidence. Even their stature changes.” 

It’s no surprise, then, that what she hopes for her own children mirrors what she hopes for her students. “I want them to find and fulfill their destiny and do spectacularly well,” she said. “That’s what I want. For them to be spectacularly successful.”