This year-long ethnographic study explored the occupational aspirations and informal educational experiences of 25 diverse homeless adolescents who found social welfare assistance through Empower, a nonprofit organization. Using organizational habitus and intersectionality as theoretical frameworks and constant comparative analysis, I found that Empower staff tailored educational programming and economic opportunities based on raced and gendered stereotyped notions of young people. Because of their precarious social positioning and the intersection of multiple marginalized identities, the Black adolescents were most positioned to obtain occupations that reproduce their ascribed social status, while the White youth were poised to improve their socioeconomic conditions.