This discussion asks why we clinicians find holding theory lightly so difficult. Commenting on Steven Stern’s clearly successful, but also conflictual, narrative, it guesses that we hold to our central, organizing, psychoanalytic beliefs because they possess selfobject, stabilizing functions for us in the face of work that threatens to disorganize us or otherwise exhaust us. When we meet a patient, as in this instance, who challenges these foundational ideas, we may hold them ever more tightly, and thus, generate struggles and impasses like the one recounted here. Only, as Stern so well explains, when we finally surrender to the rightness of the patient, embracing our own vulnerability and unknowing, allowing ourselves to be changed by the patient, has the patient an opportunity to find a way forward. This is the difficult path of clinical humility.