A longitudinal sample from the Educational Longitudinal Study of 2002 was used to determine differences in work outcomes between (a) individuals with learning disabilities or emotional-behavior disorders and (b) individuals with or without disabilities. Twelve factors were arranged into individual, family, school-peer, and community categories. Individuals with high-incidence disabilities were more likely to be unemployed, whereas those without disabilities were more likely to be employed for 20 hr or more per week. A limited number of risk factors were significant contributors of work outcomes. Ordered logistic regression revealed individuals with high-incidence disabilities and all women experienced less positive work outcomes. Parental discussions with children about work plans enhanced the likelihood of positive work outcomes, but only for adolescents without disabilities.