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Each year, as the founding headmaster of the Boston Arts Academy (BAA), an urban high school that boasts a 94 percent college acceptance rate, Linda Nathan made a promise to the incoming freshmen: All of you will graduate and go on to college or a career. After fourteen years, Nathan took stock of her alumni: of those who went to college, a third dropped out. Feeling like she failed to fulfill her promise, Nathan reflects on ideas she and others have perpetuated about education. Interrogating five assumptions about education today, she reveals how these beliefs mask systemic inequity, and explores how educators can better serve all students, increase college retention rates, and develop alternatives to college that don't disadvantage students on the basis of race or income. Drawing on the voices of BAA alumni whose stories provide a window through which to view urban education today, When Grit Isn't Enough helps imagine greater purposes for schooling.