Psychoanalytic training worldwide has frequently and regrettably degenerated into trade schooling. Against this, psychoanalysis should be a ‘calling’ that begins with each trainee’s acknowledgment of internally perpetuated suffering and thus with the rigors of being a psychoanalytic patient. The challenges of personal treatment as necessary to the journey of becoming a psychoanalyst are discussed and the pitfalls of the didactic and supervisory components of institutional training are examined. Regardless of the institutional application of ‘criteria of suitability’ for training, patient-trainees who are authentically destined to become psychoanalysts gradually experience themselves as ‘called’ to occupy the position behind the couch. This sense of transition is discussed in detail. Contrary to prevailing opinion, it is emphasized that foremost a psychoanalyst is neither an interpretive authority nor a democratic interlocutor. Rather, the psychoanalyst is a special sort of ‘friend’ who accepts, disturbs and honors the mysteries of the patient’s lived-experience. This implies that the principal function, position and attitude of the psychoanalyst is as a compassionate absenting-presence, whose labor is to facilitate the dissolution of the patient’s resistances to ongoing free-association. Only with fear and trembling can anyone authentically assume the functions of psychoanalysis, and the terrible aloneness of the psychoanalytic practitioner is discussed.