The study explored vice-principals’ interpretations of their loneliness experiences in the workplace. The following questions guided the research: (1) How do vice-principals perceive the consequences of their loneliness in regard to their personal and professional lives? (2) In what ways do vice-principals perceive that their loneliness experiences are manifested? Based on 19 semi-structured interviews with Israeli school vice-principals, six categories illustrating the consequences of loneliness in the workplace were found. More than half of the vice-principals highlighted emotional consequences, and primarily noted that their loneliness was largely expressed as feeling a lack of belonging. The other vice-principals highlighted functional consequences and primarily indicated that their loneliness was marked by an absence of emotional support. Empirical and practical suggestions are discussed.