This transatlantic study investigates how doctoral students conceptualize and navigate positionality. With a significant proliferation of doctoral programmes internationally, and many enrolled students conducting research within their own personal or professional contexts, the need to explore how they address positionality is pressing. In this qualitative paper, we present findings gathered from doctoral students researching in the social justice field in Ireland and the United States of America. The students attended two Research in Progress Seminars (Session 1: n = 20; Session 2: n = 18), where they completed a number of pedagogical activities aimed at probing their experiences and their perceptions of each other’s research. The findings evidence that doctoral students experience two central positionality dilemmas when conducting research as self-identified insiders. First, the proximity dilemma centres on how a researcher assimilates their personal experience with a topic into their research, without compromising their researcher credibility. Second, the power-empowerment dilemma centres on how a researcher can leverage current systems to bring about greater equity, without reinforcing inequities by researching within them in the first place. The paper concludes by endorsing continua approaches to positionality that are fluid, momentary and scalar, to support doctoral students in mitigating dilemmas arising from perceived insiderness.