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This phenomenological, qualitative project examined the educational experiences and college access journey of Black males (N=15) attending urban high schools in South Los Angeles and Pasadena. Research shows that when afforded equitable college access resources and supports, Black males retain and achieve in higher education equal to their minoritized peers in the college setting. I analyze an enrichment program that tackles this issue by engaging students in culturally relevant programming and championing positive cultural identity development. Participants engaged in focus groups and interviews. Data collection and analyses highlight the impact of anti-black sentiment on college aspirations and perceived barriers and review the following themes: no room for black boy joy, College and career knowledge, and Re-imagining obstacles.