Greens Farms Academy has had just 3 headmasters in the past 45 years.
As the successor to Jim Coyle, Peter Esty and Janet Hartwell, Bob Whelan has big shoes to fill.
Fortunately, he’s well on his way. He’s 6-5, and a former basketball player and coach.
Even more fortunately, he’s got a strong, eclectic background. Whelan graduated from Brown University in 1991 with a double major in American civilization and philosophy. He spent several years as a founder, singer, songwriter and director of a rock band that recorded with Atlantic Records and toured extensively.
He returned to school, earning a graduate degree in education, policy and management at Harvard, then embarked on a career in development, teaching and administration at 2 leading day schools.
Coupled with his profound understanding of the challenges facing today’s students, Whelan is the perfect educator to lead the Beachside Avenue private school into the future.
Brown challenged him to think about his passions, he says. His band, Angry Salad (“despite its name, we were not mad and had no agenda”), was a joyful time. He was surrounded by “talented, artistic, creative people.”
After 6 years in Brown’s development office he taught ethics and writing, coached boys and girls basketball, and rose to associate head of school at Rippowam Cisqua in Bedford, New York.
Whelan’s most recent position was headmaster at 130-year-old Lake Forest Country Day, with over 400 pre-K to 8th grade students just north of Chicago.
There he developed innovative spaces, did cutting-edge work with social and emotional thinking, created a more diverse and inclusive community, and reinvigorated faculty and staff morale.
When a search firm approached him about GFA, he was intrigued.
“I’d always associated Westport with creativity and the arts,” Whelan says. “It’s a beautiful community, engaged in local life and the world.”
As he learned more about the school, he realized its students, faculty and mission aligned with his own sensibilities.
He accepted the position last fall. Since then, Whelan has worked with parents and alumni — and been mentored by Hartwell, the departing head.
Whelan is spending this summer meeting individually with staff members, alumni and alumni parents. He feels like an anthropologist, discovering how Greens Farms Academy got where it is, and how it heads into the future.
“I’ve always enjoyed the relationship between teachers, kids, parents and ideas,” Whelan says.
“There are surprises at every turn: learning that the school is coming off its most successful spring in its athletic history, and seeing how the performing arts help students raise their voices. I’m having a lot of fun in this process.”
Whelan is also digging deep into Westport. He’s finding “great energy everywhere” — during an early weekend here, he was amazed at the Fine Arts Festival — and is thinking about ways to open GFA’s doors to the town.
“There are opportunities for everyone to come in and learn. A school like this has a responsibility to leverage access to a community like this, that’s dedicated to education. It’s important to bring folks behind the stone wall.”
Being head of Greens Farms Academy — with its beautiful facilities, excellent faculty, strong endowment and high-achieving students and parents — is a great opportunity.
But Whelan is well aware of the challenges.
“The world is evolving,” he says. “As we think about the tools we want our children to have, we also want them to be people of character, who can express themselves articulately. How do we help develop not only those skills, but also help them lead a fulfilling life of purpose, as they contribute to their community? How do we model that here?”
He knows that social media and technology are “incredibly compelling. How do we make the real world relevant to them?”
But, he adds, “kids are kids. Whether it’s the 1960s, ’80s or 2010s, it’s important to preserve childhood. We can’t lose sight that developing skills is not mutually exclusive with developing a sense of balance in life.”
Whelan takes over a school that traces its founding back 93 years. Greens Farms Academy, its new head says, is “more dedicated than ever to deepening its roots in the community. As the school reveals itself to me, I look forward to seeing it reveal itself to those who don’t know it.”
Bob Whelan will be an active leader. Those big shoes will soon be everywhere.