Psychasthenia 4: Insomnia is an interactive, playable artwork that explores the relationship between the regenerative world of sleep and dreams, and the increasingly pervasive technologies of self-care and optimization that are poised to occupy and transform it. Insomnia is not just about the external datification and manufacture of the self but the will towards wholesale transformation of the psyche. The user’s experience unfolds as one night’s dream journey. It begins and ends with a professional consultation with a sleep doctor, who offers his biohack to the insomniac user as the latest in a series of self-optimization apps. Fittingly for a project premised on the twin assumptions of individual agency and bodily mastery through technological intervention, we drew upon the iterative, cyclic nature of the hero’s journey motif as both metaphor and narrative structure. The experience unfolds across an increasingly surreal landscape across three levels of dreams: everyday, global, and existential.