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College prep pedagogy aimed at low-income students of color attempts to foster “grit." Findings from a two-year ethnographic study of low-income Black men transitioning to college reveal pitfalls of this practice. Participants in the study encountered a two-tiered effort paradox. First, high schools and life circumstances regularly primed participants to overexert themselves in pursuit of escaping poverty and meeting long-term goals. Second, participants’ resulting efforts proved not merely futile but counterproductive, keeping them committed to untenable workloads past a point of no return and causing exhaustion and failure. The effort paradox is a structured way that ambitious young people from low-income families can fail not despite their best efforts but precisely because of them.