This essay argues that contemporary Caribbean women exploit the malleability of life writing as a genre in a variety of ways that recognize the precariousness of life-making and self-making in the post-plantation Caribbean. While each of the writers discussed here critically refashions life-narrative for their own distinct purposes, they frequently share an interest in filtering personal life experiences through familiar familial and regional histories to emphasize the imbrication of the personal and political. Narrating life-stories is presented in these texts as inextricably linked to the difficult cultural politics of self-making that is so powerfully evidenced from The History of Mary Prince through to the present. While life-writing remains haunted by the region’s violent history, Caribbean women writers continue to excavate that history in order to record, affirm, rescue, restore, and celebrate self and life-making possibilities, however fragmented, precarious, or itinerant.