A growing body of work in relational theory and career decision making explores how relational processes, not just people’s relationships but more broadly their connections to self, others, and society, inform career development and counseling. This article presents the results of a qualitative research study of midlife women in career transition that contributes to building an empirical foundation for relational perspectives in career development. Feminist relational psychology, specifically relational cultural theory, frames the study, focusing attention on gender and culture in the context of relational influences. It extends the current research by focusing on career transition for midcareer, midlife women. Findings presented here illustrate the ways participants’ connections across a range of relationships enhanced and supported the process of career change and how their disconnections hindered, and sometimes halted, their movement through the transition. Implications for research and practice are offered.