Wellbeing matters yet it varies across individuals and contexts. Entrepreneurs face unique challenges influenced by gender, occupational roles, and external factors like policy uncertainty, which can significantly impact their wellbeing. Coping mechanisms—both individual, such as religiosity, and institutional, like safety nets—are crucial for managing these pressures. A key test of entrepreneurial wellbeing is the ability to navigate factors beyond one’s control, such as policy uncertainty. Entrepreneurs are particularly vulnerable to such uncertainty, facing greater risks compared to employees. Gender dynamics further complicate this, as female entrepreneurs often deal with compounded pressures from societal expectations and systemic inequities. Using data from sources like the World Values Survey and the Economic Policy Uncertainty Index, we empirically examine these dynamics. Our findings provide a more balanced take on entrepreneurship, revealing the emancipatory limits entrepreneurs face in terms of wellbeing, thereby, highlighting the challenges within the entrepreneurial journey.