The current study relies on in-depth interviews with twenty Black males who graduated from Du Bois Academy (pseudonym), an urban, all-boys public charter secondary school and explores their educational perceptions and experiences. In particular, the author examines the interplay between students' in-school experiences and navigating a disadvantaged urban neighborhood. Using student narratives as the guide, the findings reveal that the urban neighborhood confronts these students with an ongoing litany of challenges that have a significant impact on how they think about themselves and school. The students accent how their masculine identities mattered and identify employing resilience to maintain and enhance their academic aspirations. This research provides an opportunity to investigate how schools might help students' self-actualization, resilience, and persistence.