The lack of postsecondary success for African American males has garnered significant attention from academic scholars and public policy leaders. While this scholarship provides a strong portrait on issues related to African American males, there are still significant gaps to be addressed. Most notably, current research tends to focus on students entering four-year institutions and rarely presents student narratives about their educational experiences. The purpose of this study is to explore the experiences of African American males in various stages of transition from high school to their local community college. Students discuss three main areas--encouragement for their postsecondary aspirations, assistance with navigating multiple pathways to access, and persisting through stereotypes and perceived barriers. Discussion connects findings with theoretical frameworks to enhance our understanding of the experiences of this traditionally marginalized population.