This study examines the mediating role of employment preparedness in improving employment, mental health, and construction of work-life goals among young vocational school graduates who participated in the School-to-Work effectiveness trial. The trial included a 1-week intervention program that focused on enhancing employment preparedness. In this trial, 416 graduates of secondary vocational institutes were randomized into a control and experimental group. All the study participants were assessed at baseline, immediately after the intervention, and 10 months later. The results showed that the School-to-Work intervention increased employment preparedness, which in turn increased employment at the 10-month follow-up. Furthermore, employment predicted work-life-related personal goals and lower financial strain, which in turn was associated with lower depressive symptoms. The implications for theory and practice are discussed.