This chapter aims to investigate how women entrepreneurs, living and working in Dubai, experience the city’s cosmopolitan environment and what impact cosmopolitanism has on their business practice. Women in the UAE and particular Dubai are leading entrepreneurship into a new era as ever-increasing number of local and expatriate women come forward to turn their ideas into successful businesses. The study is based on in-depth interviews with female entrepreneurs and highlights similarities and differences encountered by local and expatriate women in Dubai. The four themes important to female entrepreneurs in Dubai are delineated: opportunities for entrepreneurship; access to resources; loneliness in a cosmopolitan city; and entrepreneurs’ societal status in Dubai. As one of its principal conclusions, the chapter discusses a trade-off between an opportunity to start own business, on the one hand, and agreeing to willingly comply with temporary and lower-level societal status that permits to do this business, on the other hand. The chapter concludes by offering insights into Dubai’s cosmopolitanism through the prism of Pierre Bourdieu’s theory of power and habitus.