This study examines the quality of the transition into employment roles among a socioeconomically diverse cohort of 1,143 high school seniors who were interviewed as seniors in 1998 and 2 years later. Focusing on both subjective and objective dimensions of work adaptation, analyses examine differences in these outcomes associated with taking a high school career-major versus a more traditional academic program. This type of major is intended to assist in the career development and economic adaptation of more disadvantaged young adults and follows from an ecological model emphasizing the importance of connections between educational and employment institutions in the socialization of young people. Results indicate small but significant effects of having the career-major for the perceptual variables. Group differences were not found for the variables assessing more objective qualities of their jobs. The discrepancy between subjective and objective outcomes may suggest a short-term psychological optimism in the absence of an objective situation that would justify this view. Discussion centers on the need for stronger institutional support for school-work connections.