Guided by ecological and integrative theories of child development, this article examined the associations between multiple systems of influence (school and family) and the educational aspirations of Black Bermudian adolescent boys. This study used qualitative data gleaned from semistructured interviews with students in their senior year at a Bermudian public high school (N = 18, Mage = 18). Findings revealed that family members and teachers encouraged boys to stay committed to school, thereby supporting high school graduation, academic confidence, and educational aspirations for higher education. However, boys had not learned enough about the complicated process of college and fellowship applications to execute their educational goals, leaving them to wonder “what’s next?” This study contributes to our cross-cultural and nuanced understanding of the important role that families and teachers play in the educational lives of Black male adolescents and suggests that interventions targeting families and teachers might promote the educational attainment, and consequent earnings, of Black male students.