Based on a secondary analysis of studies on Flemish primary schools, the article argues that the metaphor of the gatekeeper, on the threshold between the outside-school and the inside-school world, is a powerful frame to capture some of the particular complexities of principals' emotional experience of themselves and their working conditions. More in particular, the image allows for a more refined and in-depth understanding of the emotional and relational aspects in the position and role of the principal. Apart from depicting the working conditions of leadership in terms of the gatekeeper-image, the authors contend that the inevitable normative character of education contributes to a sense of vulnerability and emotionality in leadership. Two themes appeared to be prominent in principals' experience of their gatekeeper's position: first, being caught in a web of conflicting loyalties and second, the struggle between loneliness and belonging. Underneath these themes--it is argued--lies the issue of the principal's professional self in the particular school. The article concludes with suggestions for the training of (future) principals. (Contains 2 notes.)