Roman Stoicism is typically read as a therapeutic philosophy that is centered around the care of the self and presented in the form of a self-help manual. Closer examination reveals a less reassuring and more challenging side to the school’s teachings, one that provokes ethical reflection at the limits of the self’s intactness and coherence. The self is less an object of inquiry than the by-product of a complex set of experiences in the face of nature and society and across any number of flashpoints, from one’s own or others’ beliefs, actions, values, and relationships to the difficulty of sizing up one’s place in the universe. The pressures of natural and ethical reflection put intuitive conceptions of the self at considerable risk. The Roman Stoic self proves to be vulnerable, contingent, unbounded, relational, and opaque—in short, a rich matrix of problems that point beyond the individual self and anticipate contemporary critiques of the self.