Youth with disabilities face many barriers in making the transition from high school to stable long-term employment. Researchers used case study methodology to examine the career development process and postschool employment outcomes for a sample of individuals with disabilities who were working in living wage occupations 7 to 10 years after exiting high school. Key influences on initial post-high school placement included (a) participation in work experience, (b) transition services and supports, and (c) family support and expectations. Ongoing career advancement was supported by a combination of factors including (a) participation in postsecondary education or training; (b) steady work experiences; and (c) a set of personal attributes, including self-efficacy and persistence. These themes were present across all participants, but specific experiences and outcomes varied by gender.