This qualitative study focuses on 5 women who engaged in a career transition following the life-changing event of having a child. Gilligan’s 1982 groundbreaking work, In a Different Voice, brought to light the failure of developmental models to be applicable to women. This has proven especially true in the area of career transitions. Literature remains limited with regard to women who change careers, specifically in the area of transitioning to a new career after having a child. Giorgi’s (2005) phenomenological-based approach to in-depth interviewing as discussed in “The Phenomenological Movement and Research in the Human Sciences” was utilized in order to explore the subjective experiences of these women, in tandem with Gilligan’s philosophy that these experiences be expressed through the voices of the women themselves. Conversations included discussions regarding maternal influences, perception of self, and impact on future generations. Data analysis revealed the following themes: personal paradigm shift, personal courage, and personal congruency. The personal paradigm shift occurred as the result of the evolution of the women’s mental models of how life should be versus how life could be. As a form of courage that is self-referenced, personal courage enabled these women to explore this new mental model by taking actions that they may not have taken in the past. Personal congruency allowed these women to identify the various components of their lives and effectively integrate them into a whole that works for them through a pattern of integrity composed of values, principles, and ethics. The interview process provided a form of validation regarding their transitions while exploring the impact of past experiences. Ultimately, this study revealed the authentic nature of women’s career transition following the birth of a child. It demonstrates a need to look at women’s choices from not only a holistic perspective but also one that places importance on the influences women choose to either accept or deny.