This research explored how older people describe their paths to late-life childlessness. In-depth accounts from 38 childless older people, age 63–93, highlight the complex journeys and diverse meanings of childlessness for male and female participants, single and partnered, including some who had outlived children. Positioning theory is used to show how the conventional voluntary – involuntary binary is insufficient for capturing their experiences. Childlessness was for some an active choice to break a family violence cycle; for others, it was an outcome of social upheaval. It evoked feelings of both grief and relief over time, it was seen as evidence of discernment in being unwilling to parent at any price, or it was something that felt “natural” within a meaningful life. Rates of childlessness are increasing; this research highlights the fact that pathways and meanings of childlessness vary so much that it is unwise to assume that people have similar experiences of nonparenthood, especially in later life.