Finding stable employment has been identified as one of the best predictors of post-release success among prisoners. However, offenders face a number of challenges in securing employment when released from prison. This article examines processes that shape the abilities and motivations of parolees to secure gainful employment by examining interview data collected from parolees in Queensland, Australia (n = 50). We explore the role of social networks and commercial employment providers in helping parolees find work, the perceived value of institutional work and training, and the meanings, challenges, and impact of managing the disclosure of one’s criminal past to employers. Findings highlight that the role and influence of employment on a parolee’s reintegration is conditional on his or her supportive social networks, ability to manage stigma, and personal changes in identity, which elevate the importance of work in a parolee’s life. Our findings also show how employment provides opportunities for offenders to self-construct and articulate new identities.