Research on retirement has largely focused on individual and spousal outcomes, overlooking its impact on older children (youth) in the family. This study examines how parental early retirement intentions spill over to young adult children’s well-being, specifically their subjective well-being (satisfaction with life) and financial well-being (financial anxiety). Drawing from gender schema theory, we hypothesize that mothers’ and fathers’ intentions to retire early exert distinct influences on youth’s well-being. Using data from 129 triads of mothers, fathers, and young adult children (N = 387) in Singapore, results reveal that mothers’ early retirement intentions are negatively related with youth’s satisfaction with life, reflecting mothers’ role as emotional anchors within the family. Conversely, fathers’ early retirement intentions were positively related with youth’s financial anxiety. Youth’s overspending behaviour was a significant moderator of these relationships. These findings highlight the critical interplay between parental retirement decisions, youth financial behavior, and well-being outcomes. This study has important theoretical contributions as it highlights that their parents’ retirement decisions do impact youth’s well-being. Our findings provide practical insights for fostering resilience among youth and parents in families undergoing significant career transitions.