Building on the prior delineation of serendipity as a distinct mode of engaging with uncertainty, this chapter shifts focus to the individuals and organizations that appear particularly adept at navigating the Unexpected Game. It begins by contrasting passive beneficiaries of blind luck with those who deliberately create conditions for the unanticipated to emerge and be recognized. A dedicated reflection on Leonardo da Vinci illustrates how systemic curiosity, disciplined observation, and intellectual solitude can nurture a mind prepared for the unexpected. Then, extending beyond trait-based interpretations, the chapter proposes a learning-based view of serendipity. Evidence from ongoing empirical research supports the view that serendipitous outcomes emerge not from who individuals are, but from how they learn. Across diverse cases, serendipity materializes through the alignment of three semi-independent learning streams: the accumulation of shadow options through deep and curiosity-driven exploration; the encounter with emergent problems surfaced through weak ties, anomalies, or contextual mismatches; and moments of identity shift in which individuals reinterpret their role or project, enabling new connections to become actionable. These learning streams help explain why some people convert unexpected cues into meaningful opportunities while others overlook them.