Positionality statements, or statements acknowledging relevant background, context, and situatedness of researcher positions and identities are widely used in qualitative research. In recent years, public claims of insider status have been contested by the communities in question, often popularized in mainstream media. This article explores the complexities and factors that influence the way researchers think about their own positionality in relation to their participants, using written reflections on race and positional dynamics, as well as relevant literature. Through this article, I explore these complexities and the underlying motivations that compel me to present my location, identity, or positionality in particular ways. These reflections are valuable for provoking critical reflection about the way we interpret our own identities in relation to one another, and the reasons we may do so.