At a time when both philosophy of education and the arts are under threat within education, this article inquires into interdisciplinarity as one way of approaching the disciplines of philosophy of education and aesthetics. The article offers a retrospective autobiographical intellectual history and phenomenology of the author's own learning and scholarship within Higher Education in three main areas--philosophy of literature education, women's studies, and philosophy of music education, areas paralleling the three periods of her academic career. One sub-theme of this narrative about the balancing act of working in literature and music through philosophy of education is the author's ongoing resistance to professionalization or disciplinary academic control--of literature, philosophy, and music--while being a critical student of educational theory and practice in these areas--philosophy, literature and music within philosophy of education--of thus being "betwixt and between." Two other themes comprising the article's subtext are ""praxis"" and "embodiment." The "double entendre" of the phrase "working through" entails, first, using the arts of literature and music to practise philosophy of education; and secondly, embracing the psychological, ethical, and spiritual introspection that comes with critical engagement of the arts and its discourses. In short, the article aims to reprise some burning philosophical educational questions that have preoccupied its author over the years, questions deemed especially pertinent to the current increasingly diverse membership in the discipline of educational studies. (Contains 12 notes.)