Abstract Introduction: This study examined the lived experiences of Female Entrepreneurs in Lagos State, Nigeria, who transitioned from traditional corporate employment settings to venture into uncharted entrepreneurial territory. In their transition from employee to entrepreneur, this study identified the existence of glass ceiling in both phases. Considering the perception of a woman’s identity in the Nigerian patriarchal system, practical attention and analysis have not been given to their experiences as employees and entrepreneurs. Seven (7) Nigerian Female Entrepreneurs with established businesses in Lagos, Nigeria, participated in this study. Method: A qualitative research method that builds upon the philosophy of social constructivism was used to decipher the transition. Storytelling theory assisted the interviewees in expressing themselves freely and facilitated this research. Also, Schlossberg's Transition Theory was the foundational theoretical framework for this study. Result: The result of the study identified the inherent glass ceiling in their transition. Some peculiarities of the glass ceiling within Nigerian context include financing barriers, gender discrimination, a good support system, and limited female mentors. This was framed as the “second glass ceiling”. They discussed their coping mechanisms to overcome challenges and build successful businesses during transition. Conclusion: The conclusion demonstrates helpful modifications that can aid groups, organizations, academic institutions, and policymakers understand Nigerian women’s situation in corporate and business domains. Such understanding could promote equality of opportunity within society and organizations, eliminate entrepreneurship barriers, and aid their long-term retention of corporate or entrepreneurial engagement. In the long run, this will benefit the Nigerian economy, corporate organizations, female entrepreneurs in Nigeria, and their communities.