This study explored how men recently released from prison conceptualized successful reentry. Qualitative analysis of 12 in-depth life history interviews with formerly incarcerated men revealed that they defined success beyond the literature’s typical focus on criminal behavior avoidance and future criminal justice system contact. The study found several interconnected definitions of success. Central to participants’ conceptions were connection to legitimate employment, ownership, or entrepreneurship, using past experiences to assist other former offenders or recovering addicts with their problems, and the achievement of heteronormative masculine expectations. The implications of these findings for future research and practice are discussed.