Based on the author’s experience in conducting fieldwork on religion in Ethiopia, in this article she analyses the complexities of being an insider in a certain socio-political and economic context. Instead of ascribing an essence to insider-ness as a straightforward and definite category, it is argued that insider-ness is a product of dynamic and complex intersubjective interactions and processes. It is an ambiguous position marked by a continuous shift resulting from the researcher’s navigations between multiple identities at different times and environments in relation to research participants. As pointed out by Bourke (2014), the perpetual flux of one’s identity as an insider or an outsider stems from the researcher’s position: gender, class, ethnic background and religious as well as political persuasion. Furthermore, in as much as one enjoys the associated benefits thereof, the insider is faced with myriad challenges due to her or his variegated identities that in turn inform interlocutors’ perceptions, expectations and responses.