This study explored the extent to which ambiguity can serve as a catalyst for adult learning. The purpose of this study is to understand learning that is generated when encountering ambiguity agitated by the complexity of liquid modernity. "Ambiguity," in this study, describes an encounter with an appearance of reality that is at first unrecognizable, oblique, simultaneously evoking fear of "no-cognition" and the potential hope for multiple meanings irresolvable by reference to context alone. Specifically, this phenomenological study engaged nine adults who make meaning--cognitively, affectively, and interpersonally--with an extraordinary capacity for mastering complexity. The findings suggest that metaphor facilitates probing encounters with ambiguity, revealing three capacities for "generative learning within ambiguity." Given the unprecedented demands for rapid change and adaptation confronting adults today, exploring the value of ambiguity may facilitate the capacity for vital learning and intelligent action.