Widowhood in Nigeria is often accompanied by harmful cultural practices that undermine women’s rights, dignity, and economic capacity. While entrepreneurship is increasingly promoted as a pathway to women’s empowerment, little is known about how traumatic widowhood experiences shape entrepreneurial engagement. This study employs Interpretative Phenomenological Analysis (IPA) to explore the lived experiences of 12 selected widows; 2 each from each clan in Ndokwa West Local Government Area of Delta State navigating entrepreneurship after harmful widowhood practices. Analyses reveal four interconnected themes: economic disinheritance, social surveillance, psychological scarring, and resilient reconstruction. The findings demonstrate that harmful widowhood practices do not simply precede entrepreneurial activity but fundamentally shape its possibilities, meanings, and trajectories. The study contributes to feminist and entrepreneurship scholarship and offers policy relevant insights for designing context-sensitive empowerment interventions.