Remaining childless is a process which is influenced by the continuously changing context in which an individual woman lives, and by the many choices she makes in various life spheres over her life course. Most previous studies on this issue have compared mothers and childless women at the end of their reproductive years, and have sought to identify the primary reasons for childlessness by regressing measures of accumulated experience of life events on the probability of having no children. Such an approach does not allow us to capture the wide variety of paths to childlessness. Using sequence analysis we reconstruct the major life course trajectories of childless women and reveal the complexity of the life paths that lead to childlessness in the urban populations of Italy and Poland. We conclude that more reflection is needed when designing studies on childlessness, and that we will be unable to understand the complexities of the process of remaining childless unless better data and methods are implemented in these studies.