Metaphors play a crucial role in entrepreneurship, facilitating communication and conveying complex ideas. While existing research on metaphors primarily focuses on how they are employed to create external stakeholder legitimacy, this study delves into the concept of “self-legitimacy,” arguing that entrepreneurs often use metaphors to convince themselves of their venture’s desirability and plausibility. We explore self-legitimacy through the historical analysis of Josiah Wedgwood’s correspondence. Wedgwood, a renowned potter and entrepreneur, utilized metaphors in his letters to legitimate his ventures and business decisions to himself, providing a unique window into the entrepreneurial self-legitimation process. Through an analysis of over 900 letters, this study uncovers Wedgwood’s use of metaphors as images of the future, juxtaposed against the reality of his resources and aspirations. The findings shed light on the role of self-legitimacy in building resilience and coping with the inherent uncertainty of entrepreneurship.