Purpose: This study explored the different manifestations that school principals attribute to their sense of loneliness, with reference to their career seniority. The study posed two questions: (1) what are the various interpretations that school principals attribute to their sense of loneliness, in regard to the way in which it is manifested in various contexts? and (2) what do school principals note as the reasons for their feelings of loneliness? Design/methodology/approach: Based on 22 semi-structured interviews with Israeli school principals, two distinctive themes of loneliness expressions were found. Findings: Two distinctive themes of loneliness expressions were found--(1) episodic loneliness, which includes three categories: a sense of alienation, loneliness resulting from conflicts and lack of support from superiors, and (2) persistent experiences of loneliness, which included three categories: loneliness associated with an exclusive sense of responsibility for what happens at school, a feeling that the principals' experience cannot be understood and being alone in a sense of commitment to tasks. Originality/value: Despite the importance of studying loneliness in the workplace, this issue has received little research attention in the context of employees in educational systems in general and school principals in particular. Studying loneliness among school principals is of great importance due to the contention that schools' organizational structure may encourage the experience of loneliness.