Josh Wolman
Head of School

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Before joining Aspen Country Day School in 2014, Josh was Associate Head of School at Sidwell Friends School in Washington, DC. A graduate of The Park School outside Boston, Josh was a boarding student at The Hotchkiss School; he graduated from Colby College in 1991 with a BA in American Studies. He holds an M.A. in Educational Administration with a concentration in Private School Leadership from Teachers College at Columbia University. He and his wife, Rachel, are parents of two Aspen Country Day School graduates. See more.

Three items you couldn’t live without?

My family, tennis, and Aspen Country Day School.

Something we wouldn’t know about you?

I summited Kilimanjaro a few years ago. That was a good adventure.

Most interesting job before this?

I’ve had a lot of good jobs, and I feel lucky. When I was the admissions director at Sidwell Friends School in Washington, DC, I met so many people — professional athletes, politicians, a whole host of different people. I also met people who didn’t necessarily know about the school and had the opportunity now to go, and I really liked that. Also, I was a tennis pro in Nantucket when I was a freshman in college. That was the best.

Best teacher?

As a senior at Hotchkiss, I had a great English teacher for an elective called Sports and Literature. We read books like The Natural and A River Runs Through It. My math teacher in Fifth Grade at The Park School was Miss Williams. She had high expectations and everyone wanted to work hard to meet them.

What do you like most about Aspen Country Day School?

As we talk, I’m looking outside at Highland Bowl through my window and the river right outside. On this campus you’re connected to nature and obviously the setting is incredible. But it is the people who are most important — your teachers, your friendships.

Student interviewers

Stewart C., EJ B.