This chapter explores the process of working with community members on a rural community research project. A growing body of literature calls for rural research and policy development that involves participation and partnerships, specifically engaging youth and rural community members to build sustainable rural communities. It discusses the issues and possible responses to youth out-migration. The chapter explores the reasons youth choose to stay or return to a rural community, and why they leave, and extended this exploration by connecting generations to explore the context, drivers, and playing fields that can shape a rural community. Scholars stress the importance of rural community history and context and sustaining rural communities. An exploration of the researcher's role and membership in rural communities is critical, because researchers are in a position of power and play an intimate role in observation, data collection and analysis.