Purpose: The major purpose of this paper is to examine how gender differences impact the enactment of careers. An additional goal is to examine whether, as suggested by recent conceptualizations, careers are indeed becoming more boundary less. Design/methodology/approach: This paper is based on the results of two in-depth qualitative studies (n = 52; n = 27). Findings: Two major patterns were found that describe the careers of professionals in the contemporary workplace. One pattern is called the alpha career pattern over the life span, people with this pattern first focus on challenge, then authenticity, and then balance. The second pattern is called the beta career pattern over the life span, people with this pattern first focus on challenge, then balance, and then authenticity. Practical implications: This paper offers a framework that HR managers and other organizational leaders can use to increase the authenticity, balance and challenge experienced by their employees in order to enhance organizational effectiveness. Originality/value: This paper addresses the numerous calls for the development of a model to explain the complexities of women's careers as well as to recognize gender differences in career enactment. It was found that, in general, men followed the alpha career pattern while women followed the beta career pattern. However, a limited number of women had career experiences that were more consistent with the alpha career pattern more closely aligned with men while some younger men consciously developed more family-driven beta patterns. (Contains 1 table.)