“It is not that you are defined by your outcomes or your achievements, but that you, as a person, inherently matter. ”
Lorraine Riley is Head of School at Marymount School of New York, and few leaders know a school as completely as she knows this one. She first arrived as a Butler scholar at 14, an experience she says changed her life, before going on to Georgetown as the first in her family to finish college. She cut her teeth with Teach for America in post-Katrina New Orleans, helping to rebuild a school system from scratch and leading an academics programme across eleven charter schools, before returning to Marymount to run admissions and, since 2025, to lead the school through its centenary year. She is also a Marymount parent, watching her two daughters begin the same journey she once did. In this conversation, Lorraine reflects on seeing one school through so many different lenses, the power of financial aid as an engine of social mobility, and why she refuses to accept that care and rigour are a trade-off.
🎙️ Episode highlights
Lorraine reflects on knowing Marymount as student, scholar, admissions director, parent and now head, and what that rare insider perspective brings as she leads the school into its next century.
She shares what Teach for America in post-Katrina New Orleans taught her: that what makes a great school, in any setting, comes down to the educators in the building.
She gives her honest, well-oiled advice to parents navigating New York's famously fraught admissions market, and why that feeling you get walking into a school matters more than the noise.
She speaks personally about arriving on a scholarship and never once being seen as anything other than a Marymount girl, and why the school is made better by every student financial aid brings in.
She explains how Marymount uses its Catholic identity to deliver a different message in a world of toxic achievement culture: that a girl matters inherently, not just for what she achieves.
Her controversial opinion: a nurturing environment and academic rigour are not competing priorities. You need one to have the other.