This case study reflects on the interplay of the roles of insider and outsider in my work-in-progress PhD study. I adopt a qualitative approach to explore the dynamics of national identity construction in post-1997 Hong Kong through conducting in-depth interviews with activists and participants in two social movements, the Anti-National Education movement in 2012 and the Umbrella Revolution in 2014. Specifically, I reflect on my experience of being both an insider and an outsider, highlighting the tensions and dilemmas arising during my 4-month fieldwork in Hong Kong, where my hometown and my “field” is. In this case, I discuss the advantages and challenges of both insider and outsider positions by addressing the impacts that both “insiderness” and “outsiderness” can have at different stages of the research process, including designing the research, planning my fieldwork, recruiting participants, and conducting interviews. Drawing on this experience, I conclude that the boundaries of insider and outsider are not static but fluid. As researchers, being conscious of our position helps us conduct ethical and credible research.