We apply a life course perspective to study young men's transition to adulthood within the context of their return to family after a period of incarceration. Our phenomenological analysis was based on 9 in-depth, semi-structured interviews with formerly incarcerated men between the age of 18 and 24. Our findings revealed that reentry was a developmental paradox that embodied contradictions about employment, maturity, and dependence on family. A key developmental contradiction was that although employment was essential for young men's ability to become independent, it was out of reach for most of the study participants due to their criminal justice involvement. Furthermore, lived meanings around dependency on family as a result of incarceration ran counter to young men's self-definitions of adult manhood. Recommendations are discussed to help resolve these contradictions and facilitate young offenders' ability to move forward in life.