In 2012, I began a life history research dissertation examining the lives of three Black art teachers in order to understand how they conceptualize and reconcile their social and professional identities as Black/artist/teacher. As a constructivist researcher, my goal was to understand the multiple social constructions of meaning of this group, within the context of a contentious historical past. The aim of this work was to seek narratives revealing factors impacting individuals' decisions to embrace ‘artist’ as an identity and subsequently choose a career as ‘art teacher’ despite conflicting messages. Thinking about such challenges leads to a more general consideration of the relationship of an emic perspective, as a generative way of drawing out rich testimonies from participants. Applying methods of life history interviewing, this study sought to get inside the minds of these individuals in hopes to better understand the challenges associated with reconciling their identities. This case study describes several aspects of a PhD project, illuminating specific situational and methodological challenges that arose in the course of the research. It also illuminates the particularities in using life story interviews to elicit perspectives of experiences affecting identity negotiation among individuals whose experiences are shaped by racial, ethnic, and cultural heritages.