The treatment of Michael, a 10-year-old boy, illustrates a blend of drama therapy and psychoanalytic psychotherapy informed by self psychology. This chapter will focus on the first 6 months of Michael's treatment and describe how, through the expressive media of art and drama, Michael actively used me to articulate, illustrate, and illuminate his subjective world. As I describe the art work, play and dramatic enactments that Michael created, I want to add my own voice—not simply the objective experience-distant voice of the therapist describing the process of therapy, but a narrative of my subjective experience as I attempted to join Michael in his fantasy world of confusion, chaos, and fear. As I take you with me, much as Michael took me with him, I can highlight the clinical and technical points I wish to make. I will also discuss the theoretical concepts that shaped my thinking about him, focusing primarily on the issues of transference and countertransference.