This study explored principals’ perceptions of their own loneliness and their styles of coping with it. The study posed two questions: (1) How do school principals experience the personal and organizational factors that influence their loneliness in various work contexts? (2) What strategies do school principals use to cope with their sense of loneliness and when are these strategies are expressed? Based on 12 semi-structured interviews with Israeli school principals, it was found that they express two distinctive aspects of loneliness as perceived by the interviewees: a sense of abandonment by their superiors and a sense of alienation in relation to school staff. Likewise, the paper revealed five strategies that school principals use to deal with loneliness in the workplace, emphasizing the importance of building a good rapport with teachers and getting support from role players inside and outside the school. Practical implications are provided.