Self-esteem is linked to several positive outcomes. Thus, it is important to improve our understanding of how self-esteem develops and why people exhibit different self-esteem trajectories. Important events pertaining to self-esteem are life transitions, such as starting a career in young adulthood. Drawing on data from nearly 2000 participants in the Panel Analysis of Intimate Relationships and Family Dynamics (pairfam), we used latent growth curve models to examine the extent to which career entry influences self-esteem trajectories in young adulthood, particularly with respect to success at career entry and social investments in the individual’s career. In line with the notion of mastering developmental tasks, self-esteem decreased prior to career entry but increased thereafter; however, this pattern was observed only among individuals who entered the workforce at an average or late age. For early entrants, self-esteem remained stable. However, successful career entry enhanced the self-esteem trajectories of young and average-aged career entrants; namely, they exhibited greater increases in self-esteem after career entry if they were satisfied with their jobs, if their jobs paid well, and if those jobs were well respected. Social investments in one’s career had no effect on self-esteem trajectories. All of the final analyses controlled for education, job status, and gender. Overall, the results of this research indicate that self-esteem increases alongside (successful) career entry.