Jake Watson Reflects on Rewarding Return to Sidwell as New Latin Teacher

This school year, Sidwell alumnus Jake Watson ’18 joined the Upper School faculty as a Latin teacher. Prior to his arrival, Watson attended Yale University and studied Classics, specifically Latin and Greek.

Explaining his motivation for choosing a career in teaching, Watson said, “I had always been interested in teaching because I am really excited about working with young people. I learn a lot when I teach.”

Watson, who is transgender, also expressed gratitude for coming back to Sidwell as a male.

“My former teachers who were really important to me now see who I fully am, [and] I think they know me better because of it,” he explained.

Watson works alongside several of his past Upper School teachers, which he said was “one of the main reasons why [he] wanted to come back.”

Throughout college, Watson viewed his high school teachers as mentors and frequently communicated with them.

“I stayed in touch with Ms. Gilman, Mr. Gross and a lot of my middle school teachers who I’m working with now,” he said. “They’ve been really meaningful mentors to me throughout my whole life and the last four years,” he added.

Watson also strives to provide his students with a safe space for open discussions.

“As a student, I really valued the trust that teachers had in us,” he noted.

Since the beginning of the school year, Watson has incorporated collaborative activities and games into his lessons, as he “did best as a [Sidwell] student when we were having fun in class, and it felt more like a collaborative effort.”

Watson also noted that a major change at Sidwell has been more awareness of the LGBTQ+ community and issues that affect it, such as pronouns.

“Even four or five years ago when I was here, we weren’t asking folks about their pronouns,” he said. “I don’t remember many teachers who were out, and I find [the school’s progress] awesome.”

Watson’s return to Sidwell has helped him reflect on the school’s role in his life.

“To join my past memories with my present self brings this sort of completeness to where Sidwell is in my heart,” he concluded.