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This AERA paper explores how black boys in a single-sex school define and describe masculinity. Drawing from qualitative research data, I examine how boys assert, define, and contest peer and school conceptions of masculinity. I argue that boys describe manhood as discrete stages through which one must “level up”. Boys viewed the school and its demands to “level” as grinding tasks, or obstacles, concurrent with, but not integral to, becoming a man. This paper argues for schools to do away with “the grind” through increased attention to the relevance and resonance of school practices to shape boys’ experiences with respect to, not in tandem with, structural and cultural forces that inform their in-school experiences.