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This paper explores the deterioration of self-worth in entrepreneurship. Using a 15-month participatory action research in the North of England, we found mismatches between expectations and experiences at three interacting levels—purpose, autonomy, and achievement—which surface as entrepreneurs reflect on execution, performance, and fulfillment experiences. Mismatches materialize as incongruence between the ideal states under pursuit and the actual experiences, which compound leading to a diminished sense of control, direction, and worthiness, which in turn further fuels a cycle of negative emotions, involving anxiety, isolation, shame, and guilt. We discuss implications for entrepreneurs’ mental health.