DescriptionCounterfactual thinking (imagining what might have been) has been shown to play an important role in individual learning from failure, though its application to entrepreneurship has been limited and equivocal. This research seeks to better understand the relationship between entrepreneurial failure and counterfactual thinking (CFT), specifically, the likelihood of entrepreneurs to engage in CFT immediately following failure and the type of CFT that is activated under such circumstances. Entrepreneurial failure is distinct from other business failures in its significant psychological, social, and financial implications experienced by the individual. Considering the degree to which emotion permeates the entrepreneurial process and the principles and mechanisms of counterfactual thinking, I investigate the relationship between entrepreneurial failure and counterfactual thinking. I propose that the intense emotion and cognitive biases of the entrepreneur, when confronted by the unique context of entrepreneurial failure, combine to create a person/situation environment which triggers enactment of CFT. I theorize that entrepreneurs who learn from their failure utilize upward-directed, self-focused CFT to improve future performance. Support for the hypothesis presented is obtained in two vignette studies aimed at determining which type of CFT is enacted by entrepreneurs following entrepreneurial failure. The findings from these studies provide insight into the under-explored relationship between entrepreneurial failure and the entrepreneur who recovers and learns from such failure, and as a result, the entrepreneurial thinking, entrepreneurial learning, and entrepreneurial failure literatures are advanced by this research. Since the implications of upward-directed, self-focused counterfactual thinking for entrepreneurial learning are significant, it will be important to understand under which circumstances this type of CFT is enacted. With this insight, we can both predict future success in entrepreneurs who naturally utilize this type of CFT and train budding entrepreneurs to learn from their failure to ultimately succeed.