A comparison of organizational leadership choices and decision-making behaviors faced by current educational leaders and by the literary figure Lord Jim is the focus of this paper. Conrad's protagonist, when confronted by three critical life decisions, chooses erroneously. Like Jim, organizational leaders confront critical incidents that demand decisions based on personal risk-taking. A conclusion of the paper is that leaders must first experience a personal "rite of passage" to develop honesty and integrity, and learn to balance romantic notions of leadership with realistic situations. (LMI)