The aim of this study was to examine the challenges of being either a parent–coach or a child–athlete of a coach within the context of Swedish youth sport. Conceptually, the paper draws on educational and sociological theories regarding changing perspectives in child-rearing. The results are based on data gathered from interviews with parent–coaches and child–athletes (ages 13–15) of coaches involved in team sports. The results indicate that a range of meanings emerged through these unique sets of interactions, resulting in both positive and negative experiences for both children and their parents. To manage the perceived challenges, four behavioural strategies were used including: fairness, distancing, defence, and quitting. Overall, this study provides a deeper understanding of the challenges of these unique dual roles in relation to contemporary child-rearing perspectives.