A case study is presented of a client, involved in business dealings and personal relationships with members of organized crime, who upon looking into his mirror one morning recognized for the first time that his life was quickly slipping away. Unless he broke free, he decided, by doing something bold and outrageous—in the style of his free-spirited and violent youth—he was doomed to a depressive existence for the remainder of his days. He stalked women by night. Disturbed by a series of frightening dreams of his involvement in the murder of a stalked and raped woman, he approached the author for psychological help. During the course of treatment it became apparent that the client lacked a sense of personal goodness. An exploration of the problematic nature of virtue and constructive behavior in psychotherapeutic theory is presented here, together with a rationale for the role of the therapist as mentor as well as therapist for people who lack early and present experiences with constructive role models.