Research Summary: The aim of this research is to investigate the complex dynamics of entrepreneurial orientation in family businesses headed by women. With an emphasis on how emotions affect entrepreneurial processes, it provides a deeper comprehension of the emotional undercurrents affecting individual entrepreneurial orientation and, in turn, firms’ entrepreneurial orientation. This article adopts a qualitative approach through a multi-case analysis of a sample of seven women-led family businesses. The study shows that emotions significantly shape women’s entrepreneurial orientation, delineating different configurations of firms’ entrepreneurial orientation. Crucial feelings like guilt, shame, and satisfaction interact to create a range of firms ‘EOs, from analytical to emotionally-driven. Managerial Summary: This study promotes more inclusive and supportive business practices that recognize and capitalize on women’s distinct emotional and entrepreneurial capabilities, aiming to create more equitable and sustainable business environments. It does this by highlighting the emotional contributions made by women leaders in family businesses. Findings underline how crucial emotional intelligence training is for family company executives, especially women. Developing support systems designed to handle female executives’ emotional obstacles can improve strategic choice-making and corporate expansion.