There are benefits and challenges associated with conducting research in a familiar setting, especially when the researcher is more an insider than an outsider. The aim of this article is to explore the author’s experience as a native scholar conducting ethnographic research among the Swahili peoples of Lamu, Kenya. This article focuses on methodological issues related to conducting ethnographic research among the author’s own people, including examining the issues of anthropological reflexivity as a native ethnographer and highlighting the author’s experiences embodying multiple identities. Native ethnographers must consider the challenges associated with negotiating multiple roles in the research setting, especially in the presence of sociocultural factors such as gender stratification, complex kinship networks, socioeconomic hierarchies, illiteracy, and poverty. Embracing rather than being confused by the multiple levels of understanding native researchers bring to studies of their communities opens up new avenues of research and possibilities.