Objective This study examined data from the second National Longitudinal Transition Study to determine variables associated with post-high school competitive employment, and to develop a logistic regression model for predicting successful employment outcomes. Design A longitudinal survey design. Setting United States. Participants A nationally representative sample (N = 2,900) of special education students who exited high school in the 2002/2003 school year. Main Outcome Measure Any competitive employment during the 6-year study period. Results A number of predictors of competitive employment were confirmed, including high school employment experiences, parental expectations of post-high school employment, arrest record, and school type. The strongest predictors were high school employment experiences and parental expectations of a post-high school employment. Conclusions The current study supports finding of several prior studies and fail to support others, such as the importance of self-determination for adult success. The findings highlight two aspects of the transition process that are critical for success: employment training and work experiences in high school, and high parental expectations for their child’s future.