The Individuals With Disabilities Education Act (IDEA) of 2004 highlights the need for special education and related personnel to prepare youth with disabilities for adulthood, particularly in the areas of postsecondary education, employment, and independent living. In accordance with this policy, our study used qualitative case reporting to examine the personal perspectives of three adults with IDD in the outcome domains outlined by the IDEA. Using positive psychology and self-determination theories, we sought to better understand the diverse factors that contributed to the participants' “successes” in these areas. Results revealed a series of evidence-based predictors of success contributed to overcoming challenges to employment, postsecondary education, and independent living for participants. Implications for research, policy, and practice are discussed.