This chapter is an account of the development of my ideas about the role of child psychotherapists working within organisations such as the NHS; in fact, within any organisation that provides mental health services and support to individuals and their families. Over the years my ideas about the value and usefulness of a psychoanalytic training have significantly changed. I began, as I think many of my colleagues began, with a faith in the power of insight into one’s self, which therapy can offer to individuals in distress, and ended in a firm conviction in what Jeremy Holmes describes, with reference to Sutherland’s work, as “outsight”. This refers to the belief that “man is a person sustained by his social relatedness” (Sutherland, 1966, in Holmes, 1993a, p. 16), and that for psychoanalytic insight to be useful it must attend to the larger context within which the individual is placed: the family, the community (including the wider community of the helping professions), and the complexities of social reality.