Young adults with severe psychiatric disabilities face many significant challenges that put them at risk for being able to transition into adult roles, some of which include: high unemployment rates, the low participation in postsecondary training and education programs, and a strong probability of remaining on public assistance after high school. These young adults also have impairments in the cognitive processing of forethought, planning, and risk assessment—yet most programs do not emphasize the necessary skills and experiences. The purpose of this study is to investigate participants' experiences with education and support to identify the factors that would facilitate their vocational development and recovery. This study used a mixed method research design that involved both quantitative and qualitative measures. The study involved thirty-three participants from the Jump Start program, a career development and mentoring program that matched young adults ages 16–26 with severe psychiatric disabilities with mentors who themselves have had a psychiatric disability. The central research instrument used was an open-ended semi-structured participant questionnaire. There were three quantitative measures that were used: a Demographic Inventory, the Recovery Attitudes Questionnaire (RAQ-7) and the Interpersonal Support Evaluation List (ISEL). In-depth interviews were conducted with seven mentors from the Jump Start program to evaluate the mentoring relationship from their perspective. The study found that many participants prefer specific and tangible learning activities that supported them in taking positive steps in their recovery. Results also showed that interaction with supports was a critical component of their vocational development and recovery. In particular supports involving place, professionals, family, staff and peers played significant roles for the participants. The research also demonstrated that the mentoring relationship made a difference in the lives of both the participants and the mentors. Based on the findings, the researcher recommends three topics for further study. These include: (1) a longitudinal study with a larger sample as an examination of participants' experiences with education and supports; (2) a study designed to identify the variables, which foster young adults readiness to change their behaviors; and (3) a study that looks at what specific factors affects participants' ability to change their behaviors.