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Entrepreneurship is widely promoted as an inclusive pathway to opportunity, agency, and future-oriented mobility. Accelerators, incubators, and entrepreneurship education programs advance aspirational narratives that frame entrepreneurial success as broadly accessible through effort, creativity, and resilience. Yet extensive research demonstrates that entrepreneurial ecosystems are deeply structured by inequality, with access to capital, legitimacy, and recognition patterned by gender, nationality, class, and migration status. This study examines how individuals make sense of entrepreneurial possibility when these aspirational institutional narratives collide with lived experiences of structural constraint. Drawing on a twelve-month qualitative study of a university-based entrepreneurship accelerator in the United Arab Emirates, the analysis integrates participant observation, interviews, and program artifacts to trace participants’ emotional and cognitive interpretations over time. The paper develops the concept of entrepreneurial reckoning to describe the unfolding sensemaking process through which individuals attempt to reconcile institutional promises of inclusion with encounters of exclusion within aspirational entrepreneurial settings. Findings show that reckoning produces divergent trajectories—adaptive persistence, selective withdrawal, and disillusioned exit—patterned by structural position, interactional embeddedness, and narrative alignment. By theorizing inequality as a lived interpretive experience rather than a background condition, the study advances research on entrepreneurial sensemaking and inequality and offers new insight into how aspirational institutions unevenly shape entrepreneurial futures.