The purpose of this research study is to investigate the lessons from entrepreneurial experience that lead to entrepreneurs’ personal development as well as to the development of their organization. The topic was explored by conducting in-depth interviews with 16 entrepreneurs who have more than 3 years of experience in working in their own enterprise. The findings of this study are summarized as follows. First, entrepreneurs learn lessons on the various aspects of business, the self, human network, and management. More specifically, in each category, they receive messages that seem contradictory at first glance: they learn about the importance of both profit and value in business, about their own limitations and possibilities, about intimacy versus keeping distance in networking, and about intuition and expert knowledge in management. Second, despite the ambivalence and paradoxicality inherent in these lessons, the entrepreneurs integrate them through harmonizing and balancing. Third, human relationships play a key role in entrepreneurs’ learning and growth. Establishing and managing relationships is such a significant activity for entrepreneurs that it is, either directly or indirectly, connected to all types of growth experience. Furthermore, entrepreneurs learn about business, the self, network, and management through socializing with other people. This study’s contribution is threefold. First, entrepreneurs’ learning from experience is a kind of ”higher-level learning,” a transformation of one’s meaning structure. Second, it is suggested that entrepreneurs’ profit-seeking image as a businessman need to be emphasized in relation to entrepreneurship. Third, learning through relationships with more experienced entrepreneurs or peers is important in entrepreneur education.