The phenomenon labelled the “MENA gender paradox” by the World Bank is a common dominator for the MENA region countries. Women are not entering paid employment in the number one would expect considering the high rate of female educational attainment in the region. This study aims to investigate women’s motivations to enter paid employment albeit the frail chances women face in the workforce in the context of Jordan. I shed light on Jordanian women’s experiences in school-to-work-transitions and further if their expectations of this transition live up to women’s expectations. Based on evidence analysed I argue that even though women are faced with obstacles firmly established in Jordanian culture and society they strive to find ways to create the futures they want for themselves.