A newly developed instrument (retrospective well-being curves: WBC) was applied in two studies. In Study 1, a sample of 145 adults (M = 26.6 years) completed the WBC twice for different normative transitions. In Study 2, 151 university freshmen (M = 21.5 years) reported on their subjective well-being at 9 consecutive measurement points during their transition to university and completed the WBC at T10. In both studies, personality factors were assessed. Retest reliability of the individual growth parameters (intercept, linear, and quadratic change) was moderate to high (Study 1), whereas convergent validity of the growth parameters was moderate (Study 2). The results demonstrated distinct well-being trajectories for different transitions. Situational factors (e.g., timing) and personality factors (neuroticism and extraversion) were significantly associated with well-being. The results indicate that, although the use of the WBC may be limited by its retrospective design, the instrument provides a time-efficient way of measuring hedonic adaptation processes.