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This paper describes clinical and personal challenges when the therapist had to disclose his illness to long-established patients as a clinical and ethical imperative. Uncertainty about duration of treatment was processed in ways unique to each dyad. Mutual efforts at affect regulation became potent avenues of repair in some cases, although unexpected conundrums arose at the interface of privacy and disclosure, recognizing the intrusiveness of illness and its highly personal meanings. Vivid clinical vignettes and key pieces of clinical reading appeared to the therapist like visitations, spanning his career, corresponding to sustaining thoughts, admonitions, and former self-states. In kinship with authors of fiction, the therapist looks for a way through, to rebuild a holding environment capable of containing and utilizing the unwelcome news, responding very differently to each patient’s expression of compassion and caretaking, with particular sensitivity to those he feared were reenacting their own suppression of need. These became pivotal elements to explore relationally in trying to broaden the field in which topics of illness and mortality could rise above pathos, guilt, pity, despair, and other forms of isolation. In each relationship, a different wilderness was navigated.