In providing the background to a pivotal session, Stuart Pizer reveals his clinical work as an unsupervised neophyte, prior to his own analysis and analytic training. These early therapeutic efforts were flawed, leaving Pizer at times “grimacing with mortification 26 years after the fact.” But they were also extraordinarily helpful to the patient. Schaffer discusses the challenge of supervising similarly talented beginners: how does one teach psychoanalysis without desiccating a treatment? How does one teach a relational approach, with no “basic model” and few rules, to a beginning analyst infused with an unformulated, yet often passionate, sense of what is “curative”? Pizer recognizes that were he to meet the same patient today, he would not conduct the same treatment. Now trained and analyzed, not to mention more cautious and “world-weary,” Pizer would not do what he did then. But what if he were the supervisor then? Schaffer concludes her discussion by asking Pizer how he, now a seasoned analyst, would supervise his early therapist self.