A few weeks before his retirement last June, Principal Jim Gilchrist got a call from a former Aspen Community School student. The youth, then in high school, was struggling and wanted some advice.

“I was so flattered that he came in,” recalls the now-former K–8 administrator. “I instantly cleared my schedule.” He gave the boy some suggestions, steering him toward pursuits he enjoys and excels at. But the real takeaway for Gilchrist was this: “The fact that he came back here let me know that we treated him well. This wasn’t a place of fear to him. If I went back to my own elementary school now, I’d probably get a wedgie there.”

Perched on a mesa above Woody Creek with a stunning view of the Elk Range, the Aspen Community School is aptly named. With just 135 students, all of whom are on a first-name basis with teachers and staff, it’s a tight-knit place. 

Gilchrist, 61, served as principal for 18 years and as a language arts teacher for 14 years before that. When he joined the staff in 1986, the institution was private, but since 1995 it’s been a public charter school in the Aspen School District. Gilchrist consistently touted the school’s high test scores and low class sizes, but the secret sauce in the dish has always been the quality and authenticity of the relationships there. “You really have to set your intention to connect with people,” he says. “Since we’re not fixing cars or building widgets, we’d better start with the relationship piece.”

So, in what ways can an educator go about that? Says Gilchrist, “How about starting with, ‘Wow, Johnny, you look upset,’ as opposed to, ‘Hey, where’s your homework?’”

Gilchrist grew up in Chappaqua, New York, but moved west after college to rock climb, which he still does avidly. Wiry and always on the move, he works hard and tends to play even harder. After school, he would often skin up Tiehack with one or more of his outdoor-loving teachers. And this past spring and summer, Gilchrist skinned and skied the bounty of high-country corn snow well into June. 

He’s also a family man. He met his wife, Lynn Nichols, when she was a teaching aide at Aspen Community and he first came for an interview. Their two kids, Carson and Griffin, both attended the school, hitching a ride with Dad from their home in the Fryingpan Valley. The campus became a second home for a family deeply steeped in the values of lifelong learning, responsibility, and collaboration that underpin the school.

Says Skye Skinner, former executive director of Compass, the nonprofit organization that oversees both the Aspen and Carbondale Community Schools, “People would come at Jim—with frustrations, demands, or great ideas—and he always received them with an open mind and receptive ears. He is adept at listening and responding, while staying true to our educational mission and values.”

That ethos, of bringing your best self and the right values to school every day, helped Gilchrist build a dedicated staff that consistently delivers for kids. When it came time to identify a successor to the longtime principal, the school hired a teacher from within, reflecting a core belief that the magic happens in the classroom.

Says new principal Casey White, a longtime instructor in the grades 1 and 2 learning center, “There’s a real rhythm of conscious reflection at ACS, and it leads to informed decisions that make the place better.” 

That’s a tradition she’ll proudly continue, while Gilchrist rock climbs, fishes for trout, and travels with Nichols to beautiful places they haven’t yet visited during a well-earned, and now endless, school break.