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In this chapter, the authors explore the notion of loneliness in the CEO role. Traditionally, leaders are portrayed as possessing plentiful personal and social resources whereas lonely people are portrayed as socially and personally lacking, and so the notion of being lonely in a leadership position seems counterintuitive. The authors explore the elements of the CEO role and discuss the various ways the position can induce or perpetuate loneliness. The authors review the research on loneliness in relation to the CEO role and lay the foundation for future research in this underdeveloped area. The authors propose that loneliness is likely to develop when CEOs either are new to the leadership role or enact negative individual behaviors and might be felt more acutely during times of poor performance, criticism, and difficult decisions. The authors discuss implications and suggestions for future research.