WESTPORT — Bob Whelan wasn’t always an educator.

Growing up, and in his early college years, he was a basketball player with professional aspirations. He earned a walk-on spot on the roster of Brown University’s junior varsity team.

Then he was a touring musician, opening for bands like the Goo Goo Dolls and Barenaked Ladies with his band Angry Salad.

But he eventaully made his way into the field of education, most recently serving as the top administrator at Lake Forest Country Day School in the Chicago suburbs. In October, he was named Greens Farms Academy’s new head of school, effective July 1, when longtime Head of School Janet Hartwell is to retire.

Despite his many successes and myriad experiences, Whelan is a bit self-deprecating when talking about his forays into music and basketball.

At 6 feet, 5 inches tall, Whelan was an ideal size for a college small forward and walked onto the JV team at Brown University as an undergraduate.

“The initial dream had been to play in the NBA. But after my sophomore year in college, it was visibly apparent that my junior varsity status was not going to draw the attention of the (Boston) Celtics and the (New York) Knicks,” Whelan said.

His scouting report, Whelan said, might have gone something like this: “Unremarkable speed, inability to shoot from all that far away. But a real workman-like attitude out there, he really hustles.”

“My great legacy in the minds of my roommates who would come to the sparsely attended JV games were the decidedly small shorts I had to wear as a guy at the bottom of the ladder,” Whelan said.

Similarly, Whelan characterized his musical chops as “marginal, at best,” and called himself the worst musician in Angry Salad, which was formed in the years after he graduated from Brown with a double major in American civilization and philosophy. Angry Salad toured extensively throughout the country and the world — they had, Whelan said, a sizable following in China — in the mid- to late-1990s, ultimately landing a record deal with Atlantic Records. At first, it felt like a big break for an up-and-coming band.

“I would characterize it as getting the keys to the executive washroom and then getting in and handing out towels,” Whelan said.

At a major label, Angry Salad was competing for promotional resources with the likes of Kid Rock and Hootie and the Blowfish. Those were not competitions that Whelan’s crew won. When AOL and Time Warner — which owned Atlantic — merged in 2000, Whelan said most of those at the label who cared about Angry Salad were terminated and the band’s time with Atlantic came to a close.

“Parts of it were straight out of the movie ‘Spinal Tap,’” Whelan said. “It was great in terms of cultivating humility — and it was a whole lot of fun.”

At that point, Whelan, who was born in Maine to two educators, decided to again change his career course. He returned to Brown to work in the university’s development office while also pursuing a master’s degree in education, policy and management from Harvard University.

“I had always known education and educational leadership was in the background as a calling,” Whelan said. “In many respects, the apprenticeships I did in other fields helped me better understand what it took to work with talented educators and kids and communities. It was natural, there was something kind of magnetic about it.”

For six years after receiving his master’s from Harvard, Whelan worked at Rippowam Cisqua School in Bedford, N.Y., ultimately becoming the associate head of school before taking over as the head of school at Lake Forest Country Day School.

He will replace Hartwell, who has been the academy’s head of school since 2003 and will retire at the end of the school year.

“During the in-depth interview process over several stages, Bob’s energy and enthusiasm for Greens Farms and its mission were evident to all,” the GFA board of trustees said in a statement at the time of his hiring.

Since his time at Rippowam Cisqua School — a private middle school that would sometimes send students to Greens Farms for high school — Whelan said he was intrigued by the community ethos of the school and the willingness to work together to create a whole larger than its individual parts — something Whelan learned he was fond of both on the basketball court and on stage with his bandmates.

“I was always intrigued by the school. There was something about the school that I realized had to be part of their core values,” Whelan said. “The more I saw and got to know Janet (Hartwell), the teachers, students, administrators, parents — they routinely bring it back to that sense of community where everyone is known and understood and looking to create that ideal learning environment.”

justin.papp@scni.com; @justinjpapp1