This study examines the impact of entrepreneurship on the well-being, identity, and family dynamics of mothers raising additional needs children. At its core is caregiving entrepreneurship, exploring how emotional labour, advocacy, and adaptive capacities transfer into business contexts. Grounded in a feminist ethics of care, role enrichment, and resilience theory, the study conceptualizes caregiving as a generative site of growth rather than an external constraint. Mothers of additional needs children often develop profound resilience through daily care. This research investigates how these capabilities enable entrepreneurship while negotiating well-being across overlapping roles. Crucially, it identifies a resilience tax, a hidden, embodied cost where the persistence required to sustain a venture under structural adversity depletes the founder’s well-being. While entrepreneurship offers autonomy, this tax reveals the toll paid by mothers navigating systemic care gaps to maintain legitimacy. Furthermore, the study examines how framing entrepreneurship as an enabling opportunity risks individualizing the responsibility for care and economic security without challenging the broader structural arrangements that position women as primary caregivers. Using art-based methods, including Lego® Serious Play®, Photovoice, and indepth interviews, the study uncovers complex emotional dimensions such as maternal joy and defiant resilience. Findings reveal that entrepreneurial activity extends from care competencies, enabling mothers to create social and economic value. By centring the lived experiences of nine mother-caregiver-entrepreneurs, this study challenges deficit-based narratives and economically driven models of entrepreneurship. It reframes success through a care-informed lens, positioning joy and identity formation as transformative dimensions of well-being on the mothers’ own terms.