The purpose of this preliminary study was to explore the residual barriers and facilitators for a selected group of individuals with severe physical disabilities who had been afforded a comprehensive set of strategies and services aimed at meeting their basic personal as well as academic needs. Their perceptions of both barriers and facilitators, experienced while in school and post-graduation, were the focus of this qualitative research study. Due to the funding source, differences between individuals who majored in science, technology, engineering, and mathematics (STEM) and non-STEM fields were also explored. Personal interviews were conducted with a stratified random sample of 13 individuals with severe physical disabilities (IWSPD) that necessitated personal assistance and had lived at Beckwith Hall and its forerunners at the University of Illinois. Frequent educational barriers included social isolation with fewer attitudinal, programmatic, financial, or health barriers. Career barriers included more instances of social/communication and architectural/environmental barriers. Education facilitators included the disability support staff on campus; living in Beckwith Hall; state and university financial assistance; positive attitudes of faculty, staff, and fellow students; and accessibility of campus. Career facilitators included work supervisors and colleagues, with few other facilitators mentioned. STEM students were more likely to report (a) campus inaccessibility as an educational barrier, (b) career barriers of access, negative attitudes, financial expenses, and health problems, (c) disability support staff and Beckwith Hall as educational facilitators, and (d) a wider variety and frequency of career facilitators. This study provides initial yet valuable insights into the lived experience of IWSPD as they progress through postsecondary education and transition to the world of work. Significant educational supports are needed to ensure the success of IWSPD.