Subversive redemption—the sense of overturning the conventional order of things in order to recover lost parts of the self—is a virtually neglected topic in psychoanalysis. With free association, Freud empowered patients to harness unconventional thoughts and feelings. Patients who engage in subversive redemption frequently have a strong sense of agency prompting them to open up in new ways in lieu of “playing it safe.” When patients begin to express certain forbidden ideas, the boundaries of analysis are broadened, freeing the analytic pair to become fully authentic. Psychoanalysis provides patients with an arena to renew themselves as they risk “killing off” their status quo positions to achieve the paradox of living more dangerously in the safety of the analytic surrounds. Patients then feel more confident about undertaking the process of subversive redemption in the wider world.