This paper explores the potential for the concepts of time and space, together with the analogy of landscapes, to aid the exploration and understandings of women's careers. Drawing upon case studies of women who chose to opt in to self‐employment, we examine how the multi‐faceted histories of these women are drawn upon as they remember the past, explain contemporary experiences, and anticipate their futures. All the women spoke of opting in to self‐employment as the best of times; they talked of greater control over work content, the relationship between family, gender and paid work, and self‐determinism and autonomy. They noted times when their careers were frayed but only in retrospect could they assess the context, consequences and impact of events. The framework of careerscapes — our unique blending of the notion of careers along with socio‐economic and geographical interpretations of scapes — offers a framework to examine frayed careers and multiple aspects of working and caring over time and space.