A disproportionate number of urban youth attend underresourced and segregated schools. While tenets of the American Dream are inculcated in urban youth, a dearth of educational resources is available to help realize this dream. This qualitative study explored the narratives of urban youth (N = 85), many of whom sought to be the exceptions, embracing higher education as a pathway to successful futures, yet few identified resources that would make access to higher education possible. The capital accrued in their communities allowed them to navigate their social environment; however, it was an insufficient bridge for future success in higher education. Furthermore, they espoused a belief in their own self-reliance as the one resource on which they could count on. Ironically, the youth also accepted "not making it" a result of their own shortcomings. We link findings to empowerment agents who would cultivate both bridging capital and critical consciousness among/for youth.