The central aim of this paper is to highlight some of the challenges and opportunities I experienced in the field while conducting doctoral research. It focuses on some of the social and ethical issues associated with conducting research in two different Western military organisations and a remote Indigenous community in East Arnhem Land, northern Australia. Through the process of personal exploration and reflection, I seek to understand ‘how and to what extent these challenges’ (Barker, 2008, p. 09.1) shaped or impeded the research process and the ability to open dialogue regarding Indigenous Knowledges in military curricula. Using a decolonising lens, this paper analyses my journey in light of the methodology Institutional Ethnography, and the difficulties involved when selecting an appropriate research paradigm to suit multiple settings. It focuses on the interpersonal relationships between the researcher and participants; the strengths and limitations of insider/outsider perspectives (Barker, 2008; Innes, 2009); and the inherent roles and responsibilities of the researcher as a military employee and Indigenous woman from New Zealand.