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The notion of countertransference has known a troubled history within the bound of psychoanalysis and was borrowed, more or less successfully and more or less adequately, by multiple psychotherapeutic currents, some placed entirely outside the spectrum of psychoanalysis. The author will try to approach countertransference from a psychoanalytical perspective, more specifically the way countertransference and regression (both of the patient and analyst) manifest themselves, as well as the adjustments necessary between the two, considering that without a good capacity for regression the analyst may miss the “unconscious to unconscious” meeting point - that, on the one hand; on the other, a regression too emphasized or too long of the analyst may jeopardise the treatment, by activating the unconscious defence mechanisms, both in the therapist and the patient, leading to the consolidation of resistance. This specific manifestation and adjustment make the profession of psychoanalyst “an impossible profession” (Freud, Green), considering that self-analysis is one of the (incomplete and insufficient) solutions at the therapist's disposal.