This study examined whether parents' reports of midlife identity concerns and psychological well-being are related to signs of their youngster's transition to adolescence, including pubertal status, involvement in mixed-sex social relations, and persuasive reasoning skills. The sample was composed of 129 families with a firstborn child between the ages of 10 and 15. Findings indicate only very modest direct relations between parental well-being and signs of adolescent development; instead, the relations are moderated by the strength of the parent's orientation toward his or her paid work role. Among parents with a weak orientation toward work, signs of adolescent development are negatively associated with well-being; among parents with a relatively strong orientation toward work, the associations are often positive.