In this article life history data from the U.S. National Survey of Families and Households (NSFH), and the Dutch survey on Older Adults' Living Arrangements and Social Networks (NESTOR-LSN) are used to shed light on the various pathways leading to and associated with childlessness, and the proportions of men and women who have followed a particular pathway (e.g., marrying late, divorcing early, never leaving the parental home). The central question is whether the childless took different routes during early adulthood in the domains of family, education, and employment. Data point to the critical importance of transition timing, especially with regard to leaving the parental home and marrying. Delayed transitions had domino effects and blocked second chances at securing an economic base and becoming a parent. (Contains 6 tables.)