Business failure may be a challenging experience for many entrepreneurs, yet entrepreneurs continue to engage in venture creation and development. The present study integrates Social Cognitive Career Theory (SCCT) with recent theoretical and empirical insights on habitual entrepreneurship to explain and predict how past performance shapes entrepreneurs’ subsequent career-related cognitions and behavior. Leveraging a novel cross-national dataset of 2,093 experienced entrepreneurs in Latin America, this study found that compared to experienced entrepreneurs without prior failure, failed entrepreneurs are more likely to start new businesses. The study also found, counter to expectations, that the likelihood of entering paid employment decreases, rather than increases, after a venture failure. The study concludes by considering the implications of these findings and suggesting avenues for future research.