Sensemaking can be described as the ongoing, retrospective development of plausible images that rationalize what people are doing. The core idea is that when people are confronted with unexpected, confusing, or ambiguous situations, they act, and through their actions, they create the very situations they seek to understand. Reality, then, is an ongoing accomplishment that emerges from efforts to create order and to make sense of experience. Because of the increasingly complex, fleeting, and uncertain character of organizational life, sensemaking is a critical capability for organizational members, particularly leaders. Without attention to how meaning is constructed and how organizational dynamics evolve beyond control, leaders risk jumping to conclusions, overlooking or ignoring early warning signals, and missing opportunities to learn from mistakes. Cultivating a culture that supports sensemaking is therefore essential. Yet the sensemaking perspective has become fragmented, with core notions under-theorized and inconsistently applied. Unless its constituents and assumptions are critically examined, sensemaking risks remaining diffused and underutilized as a tool for navigating complexity. In this introductory chapter, I set the stage for a philosophical inquiry of sensemaking that seeks to clarify, deepen, and reorient the sensemaking perspective for contemporary organizational life.