The purpose of this study was to explore career outcomes in young adulthood among adolescents with ADHD and/or high abilities. The sample included respondents who had the ability and ADHD measures from Waves 1 (1995), 3 (2002), and 4 (2009) of the National Longitudinal Study of Adolescent and Adult Health in-home questionnaire. Using multiple group path analysis, we examined the pathways for three groups of individuals (i.e., ADHD, high ability, and both/twice-exceptional). We discovered financial and educational family background predicted occupational status and career goal attainment, as well as supports and barriers among various family and adolescent predictors (e.g., school attachment, educational aspiration, depressive symptoms). Knowledge about these trajectories will help professionals design tailored career and educational services for adolescents with high ability, ADHD, and both.