Purpose– The purpose of this paper is to discuss issues related to entrepreneurial undertakings of women in the United Arab Emirates (UAE) with the purpose of contributing to the development of context-dependent knowledge of entrepreneurship. Focussing on the life narratives of two expatriate female business-owners who created a common enterprise, the case permits to uncover and critically assess the different stages of the entrepreneurial process in a unique cultural setting.Design/methodology/approach– The authors employed a narrative case study approach to allow for a rich contextual information to emerge from the detailed accounts of individual lives and entrepreneurial experiences of case protagonists. Data were gathered from multiple sources (e.g. interviews, e-mail exchanges, web sites) and subsequently analyzed and coded into prevalent themes by two researchers and one assistant independently, permitting to achieve both data and investigator triangulation.Findings– This case elucidates the entrepreneurial journey of two female expatriates who launched their individual businesses and joined efforts in the establishment of Heels and Deals (H & D), a network that helps UAE-based women-entrepreneurs reach their professional aspirations within a patriarchal society. The cofounders are now at a cross-roads where they have to make a choice between running their own businesses to secure their sustainability and focussing on H & D to lead its international expansion. The narratives of the case protagonists allow contrasting the discovery and creation views of entrepreneurship and examining the role of leadership skills and personality characteristics in entrepreneurial success.Originality/value– Despite an increasing number of businesswomen in the UAE, little is known about the way they approach the complex entrepreneurial process and deal with challenges and opportunities faced on the road. The case bridges this gap by offering the possibility to reflect on how expatriate female entrepreneurs in a Middle-Eastern context balance multiple trade-offs to succeed in their business-related endeavors.