This study explores 1) how participation in a cognitive-based mentoring program helps justice-involved and high-risk youth develop new sense of selves and 2) the challenges youth face as they develop these new identities in their home neighborhoods. Findings from surveys and semi-structured interviews highlight youths' experiences in the mentoring program. The cognitive-based mentoring program is a safe space for young people to interact with their peers and role models with a similar background in the criminal justice system. Once their weekly two-hour group meeting ends, all of the youth return home to neighborhoods where violence is prevalent. Accounts from young people reveal how they reconcile their newly developing sense of selves with their street identities as they navigate their neighborhoods. Young people's accounts reveal a sense of agency, but also highlight how structural conditions complicate justice-involved and high-risk youth's efforts to change. The implications of this study for at-risk youth and mentoring programs are also discussed.