How do boys from diverse backgrounds manage in an elite boys' school? Interviewing a representative sample of 27 boys, blocked for race, class, and academic performance, we found that they navigated the school's academic geography by mastering “a drill” that included hard work, unwavering commitment, a will to win, a cool style, and self knowledge as learners. Some developed a transformative love of learning. But many marginalized boys struggled with the school's social geography. African American boys managed most effectively as they developed intra‐group discourses of race and class enabling them to take up the school's offers of “hegemonic habitus” without “selling out.” We discuss the liberating implications of helping students in both independent and public schools develop similar critiques.