This article explores juxtapositions of serendipity and discomfort in methodological and ethical issues raised by my research with a First Nation in Canada, in light of the changing conditions of fieldwork in indigenous contexts. It also offers reflections on the liminal condition of the PhD candidate. Personal narratives on the processes of both entering ‘the field’ and the academy, focused on experiences of discomfort, lead to larger anthropological debates, especially regarding the tensions between applied, activist and academic anthropology. Ultimately, I argue for the use of ‘reflexivities of discomfort’ as a critical tool to produce relevant anthropological knowledge.