Based on long-term ethnographic fieldwork, I explore how gender, ethnic identity, and education inform career, marriage, and family in the lives of sons and daughters of lăutari (professional Romani musicians) at the intersection of traditional Romani and contemporary Romanian society. Sons are socialized to adopt the occupation of their fathers, becoming professional musicians who will support future families; they perpetuate traditional lăutar culture. While daughters are also socialized within the family to assume domestic "female" roles, most in my fieldwork have rejected them, deviating significantly from the traditional culture of their mothers as they pursue, instead, upward mobility and socio-economic empowerment. They are pioneering new roles for lăutar – and Romani–women. For both sons and daughters, journeys of upward mobility are distinguished by achievement and success but also by dilemmas of identity and belonging as well as tension and conflict as they reconcile traditional Romani and urban, modern Romanian lives.