Purpose – Austrian economics figures centrally in organizational entrepreneurship research. However, researchers have focussed almost entirely on the Austrian school's “gales of creative destruction” and “entrepreneurial discovery” metaphors, which are rooted in equilibrium assumptions and thus downplay the more subjective and dynamic aspects of entrepreneurship. The purpose of this paper is to question such assumptions, proposing instead a “kaleidic” metaphor drawn from the radical subjectivist strand of Austrian economics. The paper develops, grounds, and enriches the theoretical concepts this metaphor embodies in order to advance the general understanding of entrepreneurship as a radically subjective, disequilibrium phenomenon, as well as the specific knowledge of entrepreneurs’ career and venture experiences. In doing so, the paper highlights creative imagination as a wellspring of entrepreneurship. Design/methodology/approach – The paper employs a case study design to inductively develop the theoretical concepts embodied in the kaleidic metaphor and deductively ground them in the accounts 12 entrepreneurs provided about their career and venture experiences. The paper employs symbolist methods to develop thicker descriptions, generate alternative understandings, and facilitate richer interpretations. Moreover, the paper adopts a reflexive approach in considering the study's implications. Findings – The results suggest the kaleidic metaphor comprises five overarching ideas that resonate, often very strongly, with entrepreneurs. Originality/value – The study is the first to theoretically develop and empirically ground the ideas the kaleidic metaphor embodies. The paper contributes to a growing body of conceptual work and joins a handful of empirical studies by organizational entrepreneurship scholars using the radical Austrian perspective.