Using the narratives of five U.S. women entrepreneurs in various stages of entrepreneurship, we explored the emergent, common themes that generate a sense of wellbeing. Their stories emphasized the need for autonomy and flexibility, challenge, family relationships, support, and feelings of accomplishment. The narratives of these women entrepreneurs help us understand factors that motivated them to start their businesses, contributed to their successes or difficulties, and had an impact on their families (including spouse/partner and children) and the significance of their ventures to their overall wellbeing. These women reflected on meaningful aspects of owning a business and conveyed how their experiences may benefit other aspiring women entrepreneurs.