Individuals with barriers to employment such as people with disabilities or people who transition from prison to the community face different challenges in navigating the world of work. Participants in this study were incarcerated males (n = 87) who completed the Career Thoughts Inventory (CTI) and the Self-Directed Search (SDS), in addition to self-reported demographic information including disability status. This study examined the relationships among positive or negative career thoughts using the CTI and career interests using the SDS. Results of this study provide a rich description of the sample and indicate statistically significant relationships among participants' generational affiliation and the CTI subscale, Commitment Anxiety. Statistically significant relationships were also identified among participant's race and the dominant career interest code as measured by the Self-Directed Search.