Dealing with developmental tasks in work and family domains is an important challenge for young and middle-aged adults. We investigated a transition that has evolved into a normative task for women, namely, the retransition back to paid work following maternity leave. In a diary study with 149 mothers who had just returned to work, we examined the daily experienced regrets concerning this return. In addition to personal resources (i.e., emotional stability, feeling prepared for the transition) and financial requirements needed to return to work, daily experienced family stress predicted decisional regrets. Moreover, our results suggest that leave length is related to psychological resilience in the face of day-to-day stress experiences: Late returners reported fewer regrets in general and were unaffected by daily family stress. Return-to-work regrets, in turn, were predictive of withdrawal intentions. This underlines the relevancy of the timing of the transition back to work in terms of successful development during this life phase.