'How to be Childless' uncovers the voices and experiences of childless women from the past 500 years and puts them in conversation with research from a broad range of disciplines, from psychology to philosophy to sociology. It addresses two main questions: What are the pathways to childlessness, and how do childless individuals flourish? Eschewing two dominant narratives - that the childless are either barren and alone or that they are carefree and selfish - it views childless individuals as complicated human beings with nuanced life stories. The pathways to childlessness, so often labeled simply "choice" and "circumstance," are far more complex and interweaving. This work examines issues including regret, old age, attitudes toward childlessness, the household, and legacy.