This study explores the transformative potential of entrepreneurship through the lens of Paulo Freire’s critical consciousness (conscientização). Using an in-depth, multi-method qualitative approach, we investigate how bar hostesses (i.e., sex workers) in Nairobi, Kenya exercise entrepreneurial autonomy (at the individual level) and emancipatory entrepreneuring (at the collective level) after engaging with a targeted virtual business incubator in the aftermath of the COVID-19 pandemic. The findings reveal how the virtual incubator became a platform for the bar hostesses to exercise critical reflection and collective action by identifying structural constraints (limit-situations), envisioning alternative futures (untested feasibility), and enacting transformative change (limit-acts). Participants developed entrepreneurial ventures that transcended stigmatized identities, enhanced agency, and created informal support networks, working collectively to build institutions rooted in mutual support and trust. By reframing entrepreneurship education through the Freirean lens of critical consciousness, we highlight how collective, community-driven approaches can transcend individualistic, market-centric narratives in entrepreneurship education.