This chapter contextualises the research approach with a discussion of ambiguity tolerance and negative capability, both qualities that Teaching Artists bring to their work in Drama-in-Education. This leads to an exploration of arts-based inquiry, with a focus on research-based theatre and approaches to data collection that allow for multiplicity and subjectivity. A personalised account reflects on how a Teaching Artist-researcher may grapple with and resist the linear trajectories of conventional approaches to data analysis. An alternative is offered that recognises that analysis is always occurring within and throughout Drama-in-Education by all participants—where threads of meaning emerge through data, narrative and theory. The chapter suggests that when Teaching Artists work as or alongside researchers, an additional layer of hybridity and reflexivity emerges.