Acquiring a job after incarceration is a perpetual challenge for ex-offenders. With nearly 95% of incarcerated individuals eventually returning to communities, the effort to understand and maintain employment and self-sufficiency may be a critical component of success. The purpose of this descriptive study was to examine the career thoughts of offenders (N = 241) nearing release. By investigating an individual's self-perception of employability and capability, those who serve incarcerated individuals may be better prepared to meet the challenge of barriers to employment after release. Results indicate that the youngest generation has higher levels of commitment anxiety; and less educated prisoners have significantly higher decision-making confusion, external conflict, and overall CTI scores. Implications and findings are discussed and future research is proposed.