Drawing on a variety of qualitative data, this case study explored one Chinese adolescent's decade-long educational journey at various American schools. The findings reveal academic triumphs, familial conflicts, and developmental dilemmas experienced by the student and the family across different sociocultural spaces. This research has implications for parents and adolescents as they cope with education, adolescence, and immigration. It also has implications for teachers about how to make connections between the Chinese home and culture and the school curricular for these students' well-rounded academic and personal development.