This paper reports on findings of an interpretive study, which used the Kaleidoscope Career Model as lens through which to view the careers of professional women in education. The study used hermeneutic phenomenology, a methodology novel in management and career management to gain a subjective perspective on women’s career experience and what career means to them at different career stages. Findings indicated that women did not “opt-out,” or adopt a clear-cut gender beta career pattern. Rather, they mirrored an alpha pattern with challenge continuing into mid-career. The three Kaleidoscope Career Model parameters operated in an ongoing way in women’s lives, and authenticity was a powerful theme throughout their careers. However, women in late career tended to “lean back”; their desire for authenticity became subjugated by their need for balance. These findings add to extant Kaleidoscope Career Model research and reveal factors, which contribute to women’s ability to “opt-in” rather than out of their careers.