Overtime, choosing not to have children has become a more common phenomenon. Alongside this change, studies have found that women without children are just as fulfilled, if not more so, in their lives as those who have had children. These studies, in the context of theories of second-wave feminism, psychosocial theory, and stigma theory, are reviewed. This study presents a dissatisfied older woman who has not had children to examine the differences in such cases. As a product of thematic analysis, five themes stand out during Holly's interview: focus on the past, stigma, fear, relationships with younger generations, and regret. Results are discussed in the context of what they may mean for future research and practice with the suggestion that perhaps an over-focus on the past, in lieu of present and future circumstances, may be a factor in childless women's dissatisfaction in life.