As the child of 2 professors who encouraged voracious reading and dinner debates, Kerstin Warner Rao said that “education was inescapable.”
She pretended to be a teacher for her sister. Yet as an art major at Vassar College, Kerstin’s goal was to become a New York City artist.
She learned quickly that materials are expensive, and most artists make little money. In 1987, when a friend invited her to teach at Brooklyn’s St. Ann’s School for the gifted, she gave it a shot.
On Day 1, Kerstin fell in love with her 3rd graders. They were vulnerable. They had senses of humor. And when she saw a light bulb switch on in their heads — when they grasped a new concept, in an “aha!” moment — it felt addictive.
Kerstin taught for 3 years in Brooklyn. She married, and moved with her husband to her home state of Minnesota. She taught for 4 more years there. When her child was 18 months old, the family returned to her husband’s native Connecticut.
They chose Westport for 2 reasons. It had a reputation as an artist’s colony. And Kerstin’s Brooklyn mentor, Dee Appleman, ran A Child’s Place preschool on Hillspoint Road.
Kerstin interviewed for 2 jobs. Teaching gifted children in Greenwich was her dream. But with a young child, she did not want to commute. So in 1999 Kerstin she became a Greens Farms Elementary 4th grade teacher.
The school was reopening, after years as the site of the Westport Arts Center. Music instructor Suzanne Sherman Propp sang a theme song she’d written for the new school. “Tears ran down my face. That song made us a community,” Kerstin says.
She was inspired too by master teacher Karen Ernst Da Silva, who gave each new Westport teacher a sketch journal. Two decades later, Kerstin has filled 20.
That first year at Greens Farms was tough. There was no cafeteria, playground, gym or library. But the staff grew close. Kerstin still meets regularly with her 4th grade colleagues: Mary Ellen Barry, Christine Theiss and Erin Shepard.
The next year, Kerstin interviewed for a spot as the gifted teacher at Bedford Middle School. She’s always had an affinity for gifted students with learning challenges — dyslexia, ADHD, whatever — and her sample lesson with the most challenging 7th grader won her the spot.
For the next 20 years, Kerstin was an integral part of “Workshop,” as Westport’s gifted students program is called.
The program dates back to 1974. Founder Annette Fournier was an educational pioneer, Kerstin says. Workshop takes students — those identified as requiring services beyond the scope of the regular curriculum — for half a day, once a week. They are given free rein to think, create, grow, test boundaries and take risks, with like-minded peers — all without the pressure of grades.
“They can write plays, and not worry that they’ll be teased for weird puns,” Kerstin explains. “They work on puzzles, improv, role-playing. They do anything that keeps their minds alert and challenging. At the same time, they foster strong, deep friendships.
“They don’t have to worry, ‘What does the teacher want?’ ‘What’s the angle of this test?’ It’s ‘what am I curious about?'”
Kerstin knows that a gifted program can be criticized as elitist. The response, she says, should be not to cut the program, but figure out how to expand it for more students.
She is grateful to the Westport Public Schools for their long commitment to Workshop. Still, it has suffered budget cuts. Once, there was a full-time gifted teacher and full-time paraprofessional at all 5 elementary schools, and both middle schools. Right now, Bedford is the only school that still has a full-time workshop instructor. The others are part-time, with other duties.
Kerstin — who is still in touch with many former students — say that they are the ones who kept her going for more than 20 years. “This is more than a job. It’s a calling. I got to know every child as an individual — their hopes, their dreams, their worries. And every day we laughed. Really, really heartily.”
Last summer was difficult, though. In the midst of the pandemic, Kerstin had difficulty sleeping, reading and concentrating. Her anxiety level was high.
Working with a therapist, she realized she was unable to teach this fall. The school district was “unbelievably supportive and kind,” Kerstin says, helping with her medical leave as she took care of herself.
Now — as she retires from the Westport school system after 22 years — Kerstin is clear about the importance of speaking openly about mental health. She challenges this “very competitive town to bring its ‘A’ game about mental wellness. Be compassionate, vulnerable, real with each other. Have the courage to support one another, and model and share our journeys.”
Bedford principal Adam Rosen invited Kerstin to speak to the staff. “I was upfront, that I was in no condition to come back this year,” she says. At the Board of Education reception for all retirees, he gave a heartfelt speech honoring her. (Click below for his speech, and her response.)
“Many of my students have struggled with mental health issues,” Kerstin notes. “I always told them that was just one moment in time for them.” Still, it was not easy for her to stand in front of colleagues and reveal her own vulnerabilities.
“Mental health still has a stigma,” she says. “It can hit anyone, out of the blue. But if your culture supports you, that’s amazingly important.”
So now — nearly 40 years after leaving art behind for a career in education — Kerstin returns to her roots.
She created a new greeting card business: Cuppa Cards. Her drawings are based on bouquets from the Westport Farmers Market.
Kerstin’s cards are on sale at Aarti Khosla’s Le Rouge Chocolatier. She’ll expand to other Connecticut stores this summer.
Her second new business is Curate Your Mate. Based on her own experience as a divorced woman who started dating again in her 40s, it’s a “midlife dating coach service.”
“I’m not a matchmaker,” she stresses. “I’m a 1-on-1 coach who helps you figure out your goals, and how to achieve them.”
That’s not so different from what Kerstin Rao did for the past 21 years, for her Workshop students. She met them where they are, heard their dreams, and walked proudly with them on their journey to fulfillment.
Which is exactly the description of every “gifted” teacher.