In this methodological reflection, I describe the multidisciplinary hermeneutic process of philosophizing about teacher dissatisfaction. I discuss how philosophy serves as a starting point for interpretive work based on interviews with former teachers and readings of qualitative and quantitative research on teacher attrition and dissatisfaction. The result has been a project that enabled me to offer new descriptions of phenomena and to develop concepts that can be used to interpret the moral dimensions of teacher dissatisfaction. The fact that I return to language and concepts as my research outcomes is why, despite my multidisciplinary approach, I continue to describe my work as philosophical. I suggest that philosophical enquiry pursued through empirical research has the potential to inform larger empirical studies, serve as a "sensitizing instrument" for empirical analysis, and to open discursive spaces where common understandings limit interpretive possibilities.