This paper will present the results of a qualitative piece of research conducted with a cohort of fourteen gay/bisexual men who are educators in a variety of contexts and phases of education in the UK. The data consists of a series of personal narratives which we collected via semi- structured interviews. The particular focus of the paper is to appraise the role of critical incidents in the narratives the subjects tell about their professional lives. The researcher will also try to make sense of the "stories" and interpretations told by him in response to the narratives told by the subjects of his research. The critical incidents presented will be considered in terms of "gatekeepers" or watersheds in professional careers. Given the sometimes ambiguous and ambivalent relationship between education, educational institutions and homosexuality, these incidents will be reviewed in terms of their significance to the individual specifically in relation to his changing sense of self identity and self esteem.