This dissertation explored the misalignment among individuals, organizations, and society that resulted from reorganization, downsizing, and loss of employee loyalty in favor of organizational productivity in the late 20th and early 21st centuries (Gharajedaghi, 2006; Morfessis, 2007). The struggle to seek realignment is the focus of this study by exploring where women’s professional interests and careers at mid-life integrate with the dynamics of the workplace and society, and how and what is experienced that brings about the emergence of transformative change. To inform this qualitative phenomenological case study from a feminist view the researcher explored the lived experiences of seven mid-life women who left organizational jobs and sought careers with more meaning. Bracketed by the women’s experiences, transformative change was explored using Scharmer’s (2007) theory U. As the theoretical framework for this study, theory U goes beyond learning from past experiences to see, sense, and actually presence the future. The outcome of this study provides guidance to organizations, individuals, and society about the transformative experience and factors that contribute to an individual’s decision to seek more meaning from a purposeful career.