In this paper, I present the idea that the documentary film My Octopus Teacher (Ehrlich & Reed) is an evocative allegory for some key threads in the ongoing learning at the heart of psychotherapy. On the one hand, the film is a narrative about a relationship formed between the narrator and documentary-maker Craig and an octopus that he encounters in daily dives in an underwater kelp forest. On the other hand, it is a story—dream of a man and an octopus who swim together in the protomental seas of the unconscious, a space where fluidity and symmetry rule, and where the boundaries between I and thou dissolve. Alongside the theme of mutual dream work, the documentary presents an evocative allegory of what it takes to practice as a therapist: the maps of our own disintegration that inform our work, and the key dispositions of learning to watch and observe and to fine tune our faith.