Recent studies have revealed that students are ambivalent about contemplating entrepreneurship as a career, and that only a few anticipate following a career in entrepreneurship after graduation. Moreover, within the start-up industry, the gender gap is still evident. The purpose of this multiple case study was to explore how and why women choose to pursue a career in either entrepreneurship or the corporate world, through the framing theory of Eagly’s Social Role Theory of Gender Difference. The researcher explored this phenomenon through a qualitative research method and a multiple case study design. The target population for this study was composed of first generation female entrepreneurs and corporate employees. The study sample consisted of 18 women; nine of these participants were first generation female entrepreneurs and nine participants were first generation corporate businesswomen. The key instrument of data collection in the study was open-ended interviews, with the collection of field notes during the interviews for triangulation purposes. The researcher subsequently analyzed the collected data with the help of Nvivo software.