A student, left, works with Anna O'Keefe ’18 through CitySquash.
True, Anna O’Keefe ’18 does not play squash. Still, she graduated straight into a perfect-fit job at CitySquash, a nonprofit that helps prepare economically disadvantaged students to dominate the T (it’s a squash thing) and, more critically, for college. O’Keefe is CitySquash director of college access and success.

CitySquash, based in the Bronx and in partnership with Fordham University, starts working with students as early as third grade in an intense, long-term effort to ensure their college success. O’Keefe works with high school juniors and seniors on test prep and college applications.

“That’s the access portion of my role. And then I also work with college students, so I support approximately 40 to 45 college students right now at colleges spread throughout the East Coast,” she explains. She helps them with financial aid, academic support, and other needs.

She has a lot of responsibility, and she relishes it, reminding herself daily that everything she does advances students.

“I wanted to go into a job like I’m in right now at CitySquash because at Hamilton I was an American studies major, and that gave me a lot of freedom to craft my own academic path. And what I ended up doing at Hamilton was focusing my major and my studies and ultimately my senior thesis, on opportunity in higher education,” she explains. “I found that I was really passionate about access and equity in education, and I wanted to transfer what I learned doing my research into some sort of professional role. And I came across CitySquash, and now I’m here.”

Long-term, O’Keefe wants to earn a master’s degree and pursue a career in higher education. One of the things she learned from Hamilton, she says, is the value of education. “I think that actually one of the coolest parts about what I’m doing at CitySquash is that CitySquash really values the type of education that Hamilton offers. Really we send students to schools very similar to Hamilton that are liberal arts, that value that type of engagement,” she says.

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