Reducing the recidivism of young offenders is a critical research issue, not only to enhance the future outcomes for the young person but also to reduce the future risk to the community. Navigating the immediate transition from detention back into the community is positioned as a critical milestone. This small qualitative study describes how young offenders participating in a formal mentoring program in Australia experienced the transition from detention to the community and the intrinsic drivers of their behaviour throughout this transition. Perspectives of their mentors and caseworker were also solicited. Importantly, their stories were interpreted through the lens of positive psychology and self-determination theory to discuss the relevance of one’s pursuit of autonomy, relatedness, and competence. Increasing our understanding of these intrinsic motivators will assist young offenders to pursue a better life away from crime and benefit both themselves and the wider community.