The authors draw from a 16-month ethnographic study to examine Latino middle school boys' early college and career aspirations. Sources of information and support for students, as well as contextual factors that shaped students' early career aspirations were explored. Findings indicate that early college and career exposure may allow Latino middle school males to form feasible college and career plans. While parents and older siblings served as sources of encouragement, teachers and other institutional agents played a more direct role in assisting students prepare and plan for college. The AVID program provided exposure and concrete information that allowed students to identify different colleges and admissions requirements. Findings from this study may be beneficial for school leaders who hope to engage Latin males during this critical stage of development and help improve their college participation rates.