Eliza Fenwick (1764–1840) lived a transformative and transnational writing life, the story of which includes a diverse range of published materials as well as life writing in the form of extant letters written between 1797 and her death in 1840. Fenwick moved from promising radical author (supporting emerging democratic, liberatory philosophies), to conservative schoolmistress and businesswoman; from the urban center of London to colonial slave-dependent Bridgetown, Barbados, and then to North America; from her status as wife of radical journalist and author John Fenwick (1757–1823), to her status as a single-working mother and then grandmother who established an independent life for herself and her family in what was then Upper Canada (now Ontario, Canada). Her career trajectory took her from promising novelist in the 1790s, to children’s book author and editor in the early 1800s. As the need to provide financial security for herself and her children overtook her literary ambitions, she channeled her literary talents (imagination, elegant prose style, eye for telling detail, and ear for dialogue) into her life writing. This essay chronicles the narrative trajectory of her life and work.