A successful entry into work is one of the key developmental tasks in young adulthood. The present 4-wave longitudinal study examined the interplay between occupational motivation (i.e., goal engagement and goal disengagement) and well-being (i.e., satisfaction with life, satisfaction with work, satisfaction with partnership, positive affect, depressive symptoms, autonomy, purpose in life, positive relations with others) during the transition from university to work. The sample consisted of 498 university graduates from 4 majors with favorable or unfavorable employment opportunities. Data were analyzed using latent growth curve modeling. The results showed that increases in goal engagement were associated with increases in numerous aspects of well-being. Increases in goal disengagement were associated with decreases in numerous aspects of well-being. However, this dynamic was not without exception. Goal engagement at graduation was associated with a decrease in autonomy and, for individuals with unfavorable employment opportunities, an increase in depressive symptoms. Goal disengagement at graduation was associated with an increase in satisfaction with work. These findings elucidate why some individuals may opt for overall maladaptive motivational strategies during the transition into the workforce: They provide selective well-being benefits. In sum, how young adults deal with their occupational goals is closely linked to changes in their well-being.