This is a narrative in a dialogue form in which the author, now an octogenarian, describes his intellectual evolution from a published laboratory researcher to engagement in the full-time clinical practice of psychoanalysis and psychodynamic psychotherapy. He reviews the development of his ideas through his many publications and offers commentaries on the nature of the origin, environment and content of his thinking at the time each of these were written. In the current article, part one of several projected articles, he covers the period from 1953, when he received his medical and research training and published his first papers, through 1965, when he resigned his positions of Chief of Psychiatry at the Veterans’ Research Hospital in Chicago and co-director of the Psychiatry Resident Training Program at the Northwestern University Medical School and entered full-time clinical work while continuing teaching psychodynamic psychotherapy at Northwestern University.