Improved healthcare and increases in life expectancy have led to people working later in life, leading to increased numbers of workers who have experienced career transitions. Consequently, workers in midlife must consider how to spend their remaining years of productivity in order to meet generativity needs. This qualitative study investigated midlife career transition and identity in a volunteer sample of eight adults who had experienced midlife career transition. Participants, ranging from approximately 40 to 60 years of age, were recruited from among the staff, faculty, alumni, and graduate student population at a small, Midwestern liberal arts college. Study interventions consisted of in-depth semistructured interviews and the researcher’s engagement in visual journaling. Open-ended interview questions yielded thick data of the participants’ experiences of midlife career transition. The researcher’s visual journal responses to the same questions yielded metaverbal and written data of her experience during midlife career transition. Analysis of interview data and the researcher’s journal responses revealed four categories. These included (a) accepting uncertainty, (b) increased flexibility (c) increased self-awareness, and (d) increased identity congruence. The findings suggest that midlife career transition may lead to increased acceptance of uncertainty, increased flexibility, increased self-awareness, and increased identity congruence, with future research recommended to study the prevalence and scope of career transition issues, as well as the use of visual journaling with individuals experiencing career transitions.