This paper explores the family, school, and community experiences of two male youth who had recently been released from custody facilities and how these experiences contributed to their sense of belonging and self-esteem. Addressing the limited literature on self-esteem and belonging of young men who had been incarcerated, the exploratory study considers key themes of trust, family, friendships, and perceptions of belonging and self-esteem which emerge from interviews and guided journal writing sessions. A key finding is that alternative literacy programs, such as journal writing, provide mechanisms to engage young men in building their self-esteem and sense of belonging. The paper concludes with recommendations for teachers, community program facilitators, and social workers to support marginalized youth after having been released from incarceration as they re-enter family and community life