This chapter examines the problems involved in writing the history of a school that one was intimately involved in, as a student, teacher and parent. It is concerned with the difficulties in writing history as a partici­ pant, a participant-observer, and, finally, a former participant. It looks at the processes I engaged in during the research and writing of my book on the history of The Dalton School (Semel 1992), and suggests that I relied on anthropological and sociological methods of field research, as well as traditional methods of historical investigation to examine a school where elites send their children. Given these field methods, it examines the problems endemic to such research and how I dealt with them. Lastly, it suggests that this type of research is to some degree a psychoanalytic journey, in which I had constantly to make sense of my own subjective experiences as they related to the larger historical record. Despite the problems encountered, I conclude that writing history as a participant and former participant is a valid form of research.