Some of the most rewarding actions we take in life are difficult. The outcomes of these actions are surrounded by uncertainty, and what relevant data is available indicates a high probability of failure. The quintessential entrepreneurial act of creating a new business is a prime example of this kind of difficult action, and the question of why people engage in this entrepreneurial act is of continued interest to entrepreneurship scholars. To examine this question, I draw on recent philosophical work on hope. Specifically, there is growing philosophical interest regarding how hope can help resolve the puzzle of how people can rationally choose to engage in difficult actions. I integrate and contribute to this line of inquiry by developing a typology of hope and entrepreneurial action. In doing so, I contribute to conversations around entrepreneurial action, rationality, and the philosophy of hope.