Through qualitative interviewing and narrative analysis, this study sought to illuminate and examine the life story of a formerly incarcerated Trinidadian woman. To gain insight into her experiences across the life course, criminal and conventional, I conducted two semi-structured interviews with the same woman in the context of Trinidad and Tobago, focusing on experiences of motherhood, interpersonal relationships, employment, and those of incarceration. The aim was to uncover the events and relationships that the study participant presented as the most significant and determinative in her life story. Through narrative analysis, I also sought to understand how they could be further interpreted through four tenets of life course theory: agency, interpersonal relationship effects, events’ timing and sequence, and the historical context. Narrative analysis identified victimisation, the subsequent undermining of personal agency, motivated advocacy and motherhood’s responsibilities as the narratives that were most central to the participant’s presentation of her life story’s trajectories. Identifying both events and personal interpretations of those events, I have posited that qualitative narrative analysis paired with a life course approach can identify experiences crucial to the development and motivation of criminal behaviour. I have also put forward that a greater focus on qualitative research into female offenders’ life histories in the Caribbean region would serve to deepen both the global and regional knowledge bases, and to better inform public policy with offender-oriented insight.