In this article, I write of an 11-year odyssey with a patient who despite our best efforts, remained mired in emotional deadness, anomie, and depersonalization. The journey led me to question my core assumptions about co-creating an effective therapeutic alliance as well as my competence as an experienced psychotherapist-psychologist, well-trained in empirically validated treatments. What I realized was a failed treatment, that led me to pursue psychoanalytic training. In the process, I grew to understand that our parallel traumatic life histories, and my inadvertent and unconscious reluctance to acknowledge my own countertransference, kept me from joining with him in the intersubjective experience of profound grief – that which, in retrospect, I believe would have made all the difference in his treatment.