The current study traced the principal's own interpretation of loneliness in the workplace throughout various career stages in the principal's career cycle. The study posed two questions: (1) How do school principals explain the personal and organisational factors that influence their loneliness experience as it relates to different contexts? (2) How do school principals interpret their loneliness experience during work in relation to their career stage? Based on semi-structured interviews with eight elementary and secondary school principals from Israel, we differentiated between two aspects of loneliness as perceived by the interviewees: one is loneliness that is associated with disappointment in the school staff performance and commitment to work. The other is loneliness associated with a sense of over-identification with the school accompanied by sensitivity to criticism. From an analysis of the principals' accounts, several insights can be provided. Empirical and practical implications are suggested.