The present study examines the educational transition from upper secondary education to further education or work in Finland from the stage-environment fit and the life course perspectives. The stage-environment fit approach states that an educational transition may elicit positive or negative changes in well-being depending on the fit between an individual's developmental stage and environment. Within the life course perspective, we review the historical time and place (Finnish education system, education and labour market) and examine the timing of the transition: on-time or off-time completion of upper secondary studies and transition to further education or work relative to other young adults and normative expectations. The sample is drawn from the “Staying on Track of Learning” study which follows an age cohort of adolescents from a medium-sized town in Finland. Participants (N=529) completed self-reports on depressive symptoms one to three times during upper secondary studies (age 16-18). Upper secondary education institutions provided register data on diploma attainment. Within two years of graduation, young adults were reached for a follow-up on studies, work and depressive symptoms. The two perspectives are combined in the longitudinal trajectory analysis of depressive symptoms across the transition in relationship with the timing and transition outcome.