This research aims to take the life-course approach to delineate the association of adolescent educational and occupational status and the psychological well-being. A scale of depressive symptoms as well as a four-category, time-varying adolescent status variables (stay in general educational track, stay in vocational track, have a job, and currently with no job nor study) are used to explore adolescent developmental trajectories. We use the panel data from Taiwan Youth Project that followed adolescents from age 15 through age 22 and employ series of group-based trajectory modeling. The preliminary analysis confirms that various adolescent statuses do produce significant effect on the diverse depressive trajectories overtime. Specifically, we identify six developmental trajectories for adolescent depression. Among them, four trajectories have clear linkage with the educational and occupational status of youth. Compared with youth in the general educational track, the majority in the vocational track are more likely to report less depressive symptoms. However, the effects vary depending on the specific trajectories revealed. Therefore, in addition to the educational influence, its interplay with the occupational experience needs to be taken into account in explaining the psychological well-being of young adults in East Asia.