How do you teach psychotherapy? What does it mean to supervise? Who should teach psychotherapy? I am involved with this question at both psychoanalytic institutes where psychoanalysis is taught and in psychiatric residencies where psychiatrists are taught. In both institutions, the teaching is done by those willing to teach, and not necessarily by the best teachers. Further, as with all work environments, friends are tapped first, again based on personal relationships and not necessarily based on what is best for students. And despite my continued plea for humility in this field, the sad truth is that we don’t know how to teach it, and student satisfaction is no proof of good teaching. Like psychotherapy itself, we have no clear guidelines about what to do and we have no clear guidelines about how to measure our effectiveness. My answer, not surprising to my readers, is to accept that psychotherapy is an art, and as such, those who choose to enhance themselves our signing up for art school, learning ideas and concepts, but no firm path to doing the work. Further, I value my credentials and I think those are important, and as such, those who teach, in my opinion, should have completed training programs which are recognized by the field, such that dynamic psychotherapy should be taught by graduates of psychoanalytic institutes since they have spent hours reading and discussing psychoanalytic concepts, and without this rigor, the depth of discussion is limited. Yet, since teaching is mostly a volunteer activity, few leaders want to impose restrictions, and so quality control is often sorely lacking. Politics is everywhere. Friends take care of their friends, and so opportunities are shared, sometimes to the detriment of students. Navigating around these waters is the art of life. Recognizing that merit based promotion is often rivaled by cronyism. We help our patients wrestle with these ideas, and so as therapists, we should understand it. I think we do, but it is still a challenge.