This conceptual article explores how antifragility might support a fuller theorization of coaching in the context of a world characterized by increasing levels of complexity, volatility and unpredictability. Antifragility, a term which describes how certain systems become stronger when exposed to volatility, has been embraced by and applied within a range of disciplines and industries but is yet to receive any substantive attention in the coaching literature. This article introduces the concept of antifragility and explores how antifragility might support a process of greater critical reflexivity in how the purpose of coaching is conceptualized and the types of coaching conversations it might facilitate. It is proposed that antifragility offers a valuable lens for re-examining and redefining some of the under-theorized norms of coaching including the still largely unchallenged assumptions concerning the benefits of performance enhancement, growth and efficiency. In doing so, this article seeks to add to the growing number of scholars who are calling for coaching to reposition itself as a vehicle for social change rather than a method of individual and organizational optimization.