This study explores how women make decisions about educational transitions, focusing on the complex interaction of personal, social, cultural, economic, and institutional factors that influence women as they move from high school to work, from high school to college, and from the workforce back to school. It also compares men's and women's experiences of transitions, and seeks to clarify how institutions create obstacles or opportunities for women making educational transitions. In a telephone survey of 1,070 respondents conducted between December 1998 and January 1999, three groups were identified: those moving from high school to full-time work; those moving from high school to college, and those moving from full-time work back to college. The study found that many women-by choice or necessity-travel not on a track but in a circuitous path as their education interacts with other life changes such as marriage, divorce, and parenthood. In separate sections, the report profiles several individual transitions, exploring the contexts of respondents' decision-making, noting goals, aspirations, and rationales for respondents' decisions, and the obstacles and barriers they faced, shows the impact of life transitions on educational decisions, and suggests some solutions. An appendix provides a demographic profile of respondents. (Contains 24 references.) (CH)