Female progressing into executive roles and senior leadership position experience various challenges in the corporate sector. In order to overcome these impediments and barriers many females transition into the world of entrepreneurship. Females expect that the entrepreneurship podium will empower, enhance and uplift their female status and opportunities relative to their male counterparts. Females equally experience a different manifestation of challenges which is similar to the challenges in the corporate sector which is indicative that gender discrimination is pervasive. The extant literature supports the notion that females currently only form 28% of top decision-making roles in South African businesses and board representation encompasses only 19% of the female gender. These statistics demonstrate that female progression is stifled by challenges and lag behind their male counterparts. The aim of the research was to assess and understand the dynamics that women face in their senior executive role in the corporate sector as well as when pursuing a career in entrepreneurship. A qualitative research method was utilised and 14 semi-structured interviews was conducted. This approach provided an in depth analysis and understanding of the challenges that female encounter in the corporate sector as well as in the female entrepreneurship environment. The results confirmed a number of factors that impede the progression of females in the corporate and entrepreneurship, namely, male domination, stereotyping, personal barriers, networking, social and cultural beliefs and indoctrination, coaching and mentoring, work-life balance, "pull me down syndrome". In addition, the study also revealed that females create their own selflimiting constraints due to excessive responsibilities, added pressures, motherhood and plainly they prefer not progressing due to their comfort zones and intimidation by males and females alike. In terms of recommendations it was found that programmes, workshops and support structures need to be implemented in order to facilitate female entrepreneurial success and assist females attempting to climb the corporate ladder. Initiatives are hurled at successful, prominent females to become role models and support the sisterhood of female business female advancement and progression in the business and employment sectors. Further research recommends that the sample size of females be increased and to categorise them in terms of race, ethnicity, culture and different hierarchical levels of employment to gain a clearer lens which to view these hindrances that still persist currently. Additionally, the geographical location of these females might provide interesting results in this regard. Furthermore, we can break it down into different industries that females participate in and investigate the impact thereof on female progression.