This article presents an autobiographical account of an older woman’s lived experience of self-employment. Little is known about women who experience ongoing self-employment into their 50s and beyond. Shoshanna’s personal narrative describes her experiences and the challenges she has faced as she reflects upon her attempts to grow and sustain her business and the implications of ageism and gender inequality in laying a claim to entrepreneurship. The narrative proceeds to reflect on her activist work, as it is constructed through the creation of a social enterprise to support older people. Shoshanna’s narrative provides valuable insights into the intersection of age and gender in self-employment moving from discrimination to active support