Within correctional settings, career development interventions focus on teaching employment skills to offenders to help them obtain work in the community. However, ongoing changes in labor market trends affect job insecurity and, thus, criminal recidivism. This article first reviews some of the existing career development interventions used with offender populations. The authors then suggest that a more dynamic approach to career development—with offenders embracing the paradoxical complexities of making career decisions that incorporate notions of flexibility, change, chance, curiosity, and hope—is needed to ensure successful transitions to the community.