A review of empirical research on self-employment of individuals with disabilities in the United States found that success appears to be influenced most by three factors: accountability systems, level of supports, and individual characteristics. In the present study, a conceptual framework based on that review was tested on federal data on individuals with disabilities who had become successfully self-employed through Vocational Rehabilitation (VR) services. Data from all 50 states and the District of Columbia were analyzed using structural equation modeling. The initial model did not converge to an admissible solution; therefore, it was respecified. The subsequent model converged to an admissible solution, however, model fit varied across location and time. A number of factors yet remain to be uncovered and tested to explain these variations. The study concludes with a discussion of limitations, recommendations for further research, and implications for researchers, VR agencies, and policy makers.