This study explored how the educational experiences of nine graduates of a transition program located in a public university in the Southeastern United States impacted their postschool outcomes in areas of employment, independent living, and the social realm. Utilizing the Halpern’s Community Adjustment Model both as a conceptual framework and an analytic tool to explore and frame the meanings participants attached to their lived experiences as graduates of the transition program, this study attempted to understand how the participants attributed their current lives to their experiences, preparation, and lessons learned while in the program. The nine participants all had intellectual disability, ranged in age from 22 to 32 years, and came from varying demographic backgrounds with regard to race, gender, and social economic backgrounds. Two rounds of interviews were conducted with each participant to arrive at an understanding of how they viewed the program, their experiences in it, themselves, their lives, and the relationship between all of these aspects. The phenomenological research perspective was used to understand the meanings participants gave to their current and imagined lives and how they related their current lives to lessons learned in the program. Findings revealed the program had profound effects on graduates and their outcomes in areas of employment, independent living, and the social realm were significantly greater and more positive than peers with similar disabling conditions as evidenced in literature. The participants described non-conventional outcomes not typical of same-age peers with intellectual disabilities.