The Gift of These Students

An Interview with Rachel Skerritt

Member, Board of Directors, The Steppingstone Foundation
Head of School, The Boston Latin School

Whenever Boston Latin’s Rachel Skerritt thinks about her extraordinary career as a teacher and leader, Steppingstone always has a special place in her heart.

Today, the Head of School contributes her passion and wisdom to Steppingstone’s Board of Directors. Back in the summer of 1999, she embarked on “my first real teaching job” in the Magnet Program, Steppingstone’s pilot initiative to prepare students for Boston’s public exam schools. While some details are hazy, “I remember feeling it was a pretty perfect fit,” she says. Then held at the Holland Elementary School, the program brought her back to her Dorchester roots. Guided by Steppingstone’s co-founder, the dynamic Mike Danziger, “it felt like a family.”

The freshly minted University of Pennsylvania graduate fed off of the Scholars’ “contagious energy and enthusiasm.” Having graduated from Boston Latin only four years earlier, she’d been in their shoes. She did her best to prepare them for the coursework and culture ahead.

In the fall, when she began teaching at Boston Latin, she reunited with some of her Scholars as “sixies”—i.e., seventh graders—in her English classes.

Today, in her day-to-day work at Boston Latin, she leads a community of nearly 2,500 students. While it’s difficult to know every student, “it’s always fun to connect with Steppingstone Scholars,” she says. She values seeing their Advisors personally checking in on them and, if she has a moment, she’ll share her own connection and history with Steppingstone.

Rachel traces her passion for teaching and urban education to her undergraduate days as an English major at Penn. She’d arrived imagining herself as a professor and scholar one day. Early on, in reading Jonathon Kozol’s Savage Inequalities in a sociology class, she realized how “blissfully ignorant” she’d been about the tragic impact of educational inequities on the lives of generations of schoolchildren in Boston. “The book struck me because it was about a city I grew up in but had never bothered to learn the history,” she reflects. “To place myself in that story was very powerful for me. I could easily imagine a very different pathway for me and my neighbors.”

In retrospect, she sees her own path to the Ivy League as having started at age 7 with a spot in a third grade advanced work class. It pains her to think about how many students were left behind along the way.

Expanding on her point, she recounts participating in an event right before the start of the pandemic with Steppingstone Alumna—and fellow board member—Mariel Novas. As Mariel shared her educational journey, “it was scary how much I already knew what she’d say,” Rachel reflects. The common elements of their stories reminded her how narrow the path to college success can be for students of color.

At the same time, she’s seen how access and opportunity can completely change the trajectory of the lives of students and families. “Education is the door to those pathways,” she says.

In opening doors, “Steppingstone should be a model,” Rachel adds. “With the right program structure, values, and support, we can close the opportunity gap,” she believes.

When it comes to outcomes, she notes that people often frame the discussion in terms of what access to top schools means to underserved students, as if the students are the only beneficiaries. She puts the focus on what they mean to their schools. They bring so much, including their brilliance, voice, passion, and resilience.

“With the gift of these students, our schools are infinitely strengthened,” she says emphatically.

When she thinks of her own school, she thinks of students like Efe Osifo, Steppingstone ’01, BLS ’07, as one of countless examples of Scholars who’ve made her alma mater stronger. Having been his seventh grade English teacher, she loved hearing him speak about his own passion for teaching at Nobles as part of Steppingstone’s virtual Annual Meeting last month.

From Rachel’s vantage point on the Steppingstone Board, the loyalty and longevity of the staff stands out to her as a “consistent force.” She applauds their intentionality.

“I have no doubt in the ability of Steppingstone to take care of their students,” she says.

For anyone who questions the ability of our educational systems to prepare students for rigorous academic study and a path to college success, Rachel points to Steppingstone as a counternarrative.

She’s no stranger to educational debate. When it comes to ideas for revitalizing the nation’s urban schools, there’s no shortage of experts. When someone talks about what students deserve, she asks them to picture the young person in their life to whom they’re closest.

“What would you want for that student?” she asks.