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Through a New Teacher’s Eyes: A Culture of Curiosity and Kindness

November 11, 2026

As part of our ongoing attempt to see and articulate Waring’s culture, we sat down with new math Jenna Wilkey to ask her what she’s noticed about life on campus.

Before coming to Waring, Jenna taught middle school math in the Lawrence Public Schools. Before that, she lived in Sarajevo and Belgrade, where she was a volunteer coordinator with refugees, taught English, and took testimony on border violence. She holds a BA in Economics and Global Environments & Sustainability from the University of Virginia, and an MA in Education from Boston University. At Waring, Jenna teaches math and electives, and works as a Tutor, the school’s version of an advisor.

During her first days on campus, she noticed students’ willingness to work with each other––and with their teachers.

Once students are told who they’re working with, “without any further input they find their groups,” she says, “and find locations…They’re excited to work with anyone in the class. And there’s often multiple people stepping up to lead the groups.”

She sees this same self-direction in class discussions. “One person takes the lead, and then someone else naturally starts talking without me having to jump in,” she says. “They’re like tiny adults.”

At Focus/Flex, the daily free periods when students are responsible for their own time, she noticed a group of her students “ all reading a book together. One person was reading out loud while everyone else was following along…They were engaging in a discussion about literature outside of the class.”

But what she notices most is students’ kindness. On Waring’s start of the year Camping Trip, “my Tutorial seniors did a wellness check on me…they were just kind of like, ‘this must be so much for you. How are you feeling?’…I was like, I should be checking in on you!”

And when the editors of this blog let Jenna know that they would be running the post by her to be sure it reflected her opinions, she had another impromptu reflection on Waring’s culture: “wow, people really care about what you think here.”