Play has long been recognised as a vehicle by which significant developmental advances occur during early childhood. Children use play to explore their relationships, their psychosocial skills, and their environment, and through their experiences, they begin to adopt specific capacities and values that have an impact on future socio-emotional and academic outcomes. To understand more fully the factors that contribute to well-being in early childhood, we explored footage of a full "day in the life" of a 5-year-old boy in transition to kindergarten, and we conducted interviews with him, his parents, and teacher. We identified agentive and communitarian strivings to be significant sources of his thriving and primary elements of many episodes of play during his filmed day. Previous research indicates that the development of strong agentive and communitarian skills and values is related to positive psychosocial outcomes. The current case study explores our participant's agentive and communitarian behaviours as exemplified through episodes of play, and the ways in which these skills and values are encouraged and supported by his caregivers. Implications regarding the role of parents and educators in the facilitation of agentive and communitarian skills are discussed.