A Korean national database, the High School Graduates Occupational Mobility Survey, was used to examine the influence of perceived social supports (family and school) and career adaptability on the subsequent job satisfaction of work-bound adolescents 4 months after their transition from high school to work. Structural equation modeling analysis revealed that social supports indirectly influenced job satisfaction by enhancing career adaptability. Perceived school support and family support were found to be highly correlated with each other, indicating individuals are cognitively consistent in their perceptions of environmental supports. Gender differences existed on all chosen variables (except for career planning), with women reporting greater levels than men. A significant gender difference was also found in the relationship between career adaptability and job satisfaction. Men were more influenced by career adaptability in experiencing job satisfaction than women. Interpretations of these findings were shared in light of career development theory and Korean culture.