This study used a school-based community sample (N = 920) to examine trajectories of depressive symptoms, self-esteem, and expressed anger in the critical years of emerging adulthood (ages 18-25). Using data from 5 waves, the authors discovered that multilevel models indicated that, on average, depressive symptoms and expressed anger declined, whereas self-esteem increased. Between-persons predictors of variability in trajectories included gender (gender gaps in depressive symptoms and self-esteem narrowed), parents' education, and conflict with parents (depressive symptoms and expressed anger improved fastest in participants with highly educated parents and in those with higher conflict). Across time, increases in social support and marriage were associated with increased psychological well-being, whereas longer periods of unemployment were connected with higher depression and lower self-esteem. Emerging adulthood is a time of improving psychological well-being, but individual trajectories depend on specific individual and family characteristics as well as role changes.