The research investigated the association between school engagement and adult education and occupation outcomes, within the context of a 1985 Australian longitudinal national cohort study of the factors affecting children's long-term health and well-being. School engagement may be more modifiable than other factors related to academic success, such as academic attainment, which is influenced by family background. A School Engagement Index was constructed using questionnaire items on school enjoyment and boredom. Related school engagement items included learner self-concept, motivation to learn, sense of belonging, participation in school or extra-mural activities, and enjoyment of physical activity. In 2004–2006, participants (aged 26 to 30 years) reported their highest level of education achieved and current occupation. Potential covariates included age, sex, markers of socio-economic status in childhood, personality and school-level variables (i.e., number of students, single sex versus co-education; government, private or independent). Logistic regression was used to estimate the odds of achieving post-compulsory school education and achieving higher status occupations. Findings revealed that each unit of school engagement was independently associated with a 10% higher odds (OR 1.10 95% CI 1.01,1.21) of achieving a post-compulsory school education. Maternal education, self-concept as a learner, motivation to learn, all also significantly predicted achieving post-compulsory school education. School engagement was found to mediate the association between the personality characteristic of agreeableness and education outcomes. Higher school engagement was also independently associated with achieving higher status occupations 20 years later (OR 1.11 95% CI 1.03, 1.20). Importantly, this was independent of a host of background factors.