In this paper I consider some of the affinities between the teacher-student dynamic in academic supervision, and the therapist-patient dynamic in the therapeutic relation. Drawing on my own experiences, I identify several difficulties that pertain to these two settings. First, in the context of the classroom, I consider how the requirement to speak and the requirement to write call for different modes of engagement, and can provoke different types of anxiety. I explore the function of mediating texts as a way of engendering a critical distance from one's own speech acts. I then turn to Sigmund Freud's intriguing evocation of the quality of "aloofness" as that which should colour the patient's engagement with the transference situation. I shall treat Freud's recommendation of aloofness as a mode of critical distance--and a type of impersonality--that can be put to work in the classroom as well as in the consulting room. Finally, I ask what happens when distance fails; when there seems to be no space for impersonal critique. One way of thinking about the failure of distance is through the lens of shame. Here I focus my thought on the contention that the scope for shaming is especially prominent in vocational settings that challenge and interrogate the subject's capacity to know.