Individual and contextual factors in childhood and adolescence that were hypothesized to contribute to career pathways were examined in a prospective study. Four career pathway groups were distinguished in a sample of 202 at-risk men (23-24 years of age); namely, young men with long-term unemployment, short-term unemployment, full employment, or a college education. Measures of educational attainment, family and peer characteristics, and personal adjustment during childhood and adolescence were used to determine if they would predict early adult career pathways. Findings indicated that the long-term unemployed young men, overall, showed the poorest levels of educational attainment, family and peer characteristics, and personal adjustment during childhood and adolescence. The most important predictors of differing career pathways were educational attainment, arrests, and mental health problems. Implications of the findings for conceptualizing the school-to-work transition within an integrative framework are discussed.