This Participatory Action Research (PAR) project worked with four active street-life-oriented Black men to document how a community sample of street-life-oriented Black boys between the ages of 16 and 19 frame and use “street life” as a site of resilience inside schools. Qualitative data were collected in the form of written responses on 156 surveys, 10 individual interviews, and one group interview. Data were primarily collected inside the street communities of Harlem, New York City and Paterson, New Jersey. Qualitative findings reveal the young men, overall, hold positive views of formal education and its significance in their lives. Yet they hold negative attitudes regarding previous and current educational experiences. Also, results demonstrate the young men ultimately position their street orientation as an adaptive identity to have inside schools.