How do envisioning dreams like fairy tales inform the therapist’s ability to talk with their clients about dreams? Using the research methodologies of heuristics and hermeneutics, the author tended to a dream while enrolled in a graduate program in psychology. He explains his dream as an imaginative story that reflects many of the ideas and concepts of depth psychology. The mythopoetic function of the unconscious is explored in relation to archetypal, historical, and fairy tale figures appearing in the dream, such as Bilbo Baggins, Trickster, Cleopatra, the Dalai Lama, and Frederick Douglass. Threads of depth and applied psychology are woven into the discussion, creating a link between the author’s dream and fairy tales. The research suggests that dreams, when envisioned as imaginary tales, are less frightening and more palatable, inviting selfdiscovery and transformation in the process of psychotherapy.