While psychoanalytic and educational research consistently document a fraught relation between the two fields, they share in common the problem of how to influence others in the direction of psychical and perhaps more so in the case of education, social change. And yet, the changes at stake in psychoanalytic theory do not proceed from conscious effort or the right kind of knowledge. In this paper, I consider the problem of influence as an ironic registration marked not by the analyst's intention, insight or charisma, but by her capacity to survive the disillusionment of these ideals in the face of the analysand's regressive crises. Drawing on two analytic pairings (Loewald/Lear and Winnicott/Little), I show that the foundation of psychical change proceeds not from instruction or insight but, from the opposite direction: or, the analysand's regression. For education, what remains is a question of how the teacher can survive not only the helplessness of her own helping hand, but also the hatred of this vulnerable human condition.