Therapists’ quest for constructing meaning systems of their patients’ experiences progresses in cycles. These cycles consist of: (1) efforts to achieve closures, propelled by the depressive position with its concomitant judgments, resolutions, and decisiveness, and (2) efforts to dissolve closures, propelled by the schizo-paranoid position, searching anxiously and excitedly for new ways to construct meaning. By struggling to facilitate their supervisees’ cycles of achieving and dissolving closures, supervisors help them to grow as clinicians. Supervisees usually welcome the supervisors’ help in constructing meaning systems and achieving closures. They become wary, however, when their supervisors suggest that they dismantle these systems and dissolve their closures because these suggestions undermine their self-assurance as well as their sense of morality, both nourished by the depressive position. Several approaches are suggested for supervisors to facilitate their supervisees’ efforts to dissolve closures.