Conceptualising one’s academic self in relation to the multiple roles and identities that present themselves in academia can be an overwhelming, consuming and isolating experience. We, Una and Michael, have similar professional biographies in teacher arts education in Ireland. This chapter maps, tracks and unpacks the trail which we have followed as we pursue our multiple identities of Teacher, Researcher, Artist and Leader over the past two decades in the field of initial teacher arts/ education. Our arts based explorations investigate the lived experiences of these disparate, but often intertwined and sometimes conflicting roles. Grounded by theory concerning arts leadership, identity, and self-recreation, and using a narrative inquiry and arts-based approach, we interrogate our respective professional biography within the broader context of educational change and development to seek points of alignment, intersection and collaboration. We critically and dialogically reflect on how we strive to remain true to our values, beliefs and ambitions whilst progressing the priorities, needs and strategies of school, university or external stakeholders.