Through a qualitative study of senior executives, the authors examine how they incorporate loneliness into their self-narratives, and how the way they do so influences their relationships to their executive role, their history, and to other people at work. They found two distinct ways of incorporating loneliness—defensively and developmentally. Those who incorporated loneliness defensively narrated it as provoked by their roles, which required them to be guarded and detached, and consistent with their history of self-reliance and independence. They maintained distant relationships with coworkers and believed that loneliness was a necessary, albeit unpleasant, requirement for a successful career.Executives who incorporated loneliness developmentally also narrated it as necessary, not in relation to their ascent to an executive position, but rather to the responsibility that this position entailed. They challenged the connection between self-reliance and success, and instead narrated loneliness as a feature of their choice to serve their firm and its people. Building on these findings, the authors develop a model that recasts loneliness as a psychosocial phenomenon and reveals how executives’ narratives of workplace loneliness shape their interpersonal and intrapsychic worlds, as well as the ways they occupy and deploy their selves in their roles.