What is often regarded as luck in entrepreneurial and managerial settings may reflect an underlying process of recognition, interpretation, and timely action. This chapter traces the conceptual evolution of serendipity from its literary origins to its contemporary relevance in organization theory and innovation studies. Based on academic studies, the chapter outlines the dialectical dynamics and three necessary conditions for serendipity (agency, surprise, and value) and shows how these conditions translate into a fragile, stage-based journey from triggering to realization. Drawing from empirical cases and original fieldwork in digitally transformed SMEs, it also reveals how contextual enablers and organizational practices shape serendipitous discovery. A taxonomy further improves the conceptual clarity about the phenomenon, distinguishing four types of serendipity: Walpolean, Mertonian, Bushian, and Stephanian. Finally, the chapter discusses how serendipity can be measured through a validated six-item scale for managers, organizations, and entrepreneurs. It also includes concrete application in recent studies linking it to organizational behavior, entrepreneurial well-being, and patents. Serendipity, the chapter argues, is something that can be actively triggered and meaningfully harnessed.