The present study tracked a group of Year 12 students 9 months after leaving high school and sought to identify whether age, gender, data on career maturity, psychological wellbeing, and school achievement reported while still at school could be identified as predictors of occupational status. Data on these variables were able to identify broad postschool occupational groupings of school leavers at Time 2 (T2), whether they were in full-time study, full-time employment, or unemployed/part-time employed. Findings support the assertion that career maturity is a predictor of a successful postschool transition. Discussion focuses on the need to explore movements between the occupational groupings and implications for school-based interventions.Changes in the world of work for adolescents create an imperative to prepare individuals with the necessary skills for more complex and multiple job/ career transitions. Early work experience in a full-time job has been the major stepping stone for young people to adult life since the end of the Second World War. However, significant changes in the nature and structure of the work force during the 1990s meant that this stepping stone was largely removed. The proportion of 15-to 19-year-olds with a full-time job fell from 28% at the beginning of the 1990s to 17% by mid-1996. However, data also show that these 15-to 19-year-olds are all not in full-time education. Although the 1980s saw a significant growth in school completion, peaking in 1992 at 77%, the years since then have illustrated an annual decline, to a low