This study used a phenomenological qualitative approach that engaged Black students in discussions about the burden of acting White and its impact on their in-school and postschool outcomes and postschool transition visions. Six seventh- and eighth-grade Black students identified as at risk for school failure, a principal, and five teachers participated in this study. The authors identified and addressed the following themes: (a) the existence of the burden of acting White; (b) students' definitions of acting Black or White; (c) teachers' inability to intervene and counteract the impacts of acting White; (d) the significance of postschool visions; and (e) academic orientation. The authors conclude by discussing the need for transition programs focused on self-determination.