Most studies of internationalization of firms over the past forty years have focused on how firms choose markets and/or entry modes at the first attempt or at the subsequent attempts later to enter foreign markets following the first successful entry. At the same time, researchers have noted that there have been a high number of firms withdrawing from their international operations because of their failures in foreign markets. There have been a few studies dealing with the question of how firms can re-internationalize successfully after having failed in previous internationalization. However, studies dealing with the question of firm’s successful re-internationalization after having failed previously are lacking. More specifically, the knowledge of how small firms choose their products, markets, and entry strategies in re-internationalization has remained unclear. Researchers suggest that the success of small businesses depends on many factors. The key determinant is the entrepreneur himself/herself. According to school psychological characteristics, entrepreneurs would have unique values, attitudes, needs, and drives in order to succeed. Researchers also maintain that psychological traits may exhibit certain degree of entrepreneurial orientation and internationalization of small firms is directly related to personality and experience of business owners. This study investigates how psychological traits of entrepreneurs, including the need for achievement, locus of control, risk-taking propensity, and tolerance for ambiguity, influence entrepreneurs´ choices of product, markets, and entry strategy in their re-internationalization process. Our analysis suggests, entrepreneurs make different strategic choices in re-internationalization process based on their psychological traits. Moreover, experiences of entrepreneurs and foreign language knowledge play a mediating role in the relationship between psychological straits and their strategic choices and in the success of re-internationalization process.