Entitlement is an emotionally based but not necessarily pathological mode of experiencing psychic reality, one which belongs to both analyst and patient participating in the intersubjective matrix. I use myself as an example of an analyst who initially believed he was constructively analyzing treatment-resistant entitlements. The course of the work involved identifying expressions of entitlement in myself, as well as in the patient or supervise. I came to understand that distinctions such as normal or pathological, entitled or counterentitled, often become irrelevant. The focus of the work shifts toward uncovering the bidirectionality of entitlement experiences, revealing the varying elements of entitlement and discovering how they function in the therapeutic relationship.