The influence of the family on its members is significant. Parents impart professional values and priorities that shape the perspective and often career choice of their children. Drawing on Family Systems Theory, this case study focuses on how the teaching profession connects and impacts one geographically dispersed, multigenerational family. Findings suggest that teaching connects family members through service to others, shared family values, early influences, identity construction, tradition, and even rebellion. Family members are proud of their fellow teachers, and of the younger generations for continuing the family 'business'.