The typology of learning from successive failures—the overconfidence effect on judgment errors

While entrepreneurial failure has been widely studied, it remains unclear why repeated failures do not always lead to learning, particularly when decision-making is shaped by cognitive biases. This study examines how interacting biases distort learning from successive failures, drawing on a longitudinal case of an entrepreneur who experienced repeated venture failures. Overconfidence, reinforced by optimism, motivational reasoning, and confirmation bias, produced persistent judgment errors in opportunity identification and venture evaluation. Applying attribution theory, we show that initial internal attributions at the organizational level enabled only superficial learning, while deeper learning emerged when the entrepreneur critically reassessed beliefs through hybrid attributions across individual, organizational, and environmental levels. The study’s key contribution lies in demonstrating that overconfidence operates through interactions with other biases, delaying reflective learning and allowing errors to persist. By theorizing these dynamics, the research clarifies when and why failure leads to transformative rather than repeated misjudgment.