Community colleges in the United States are facing what some researchers are calling a "crisis" (Piland & Wolf, 2003; Shults, 2001). The current generation of community college leaders, those born to the birth cohort known as the Baby Boomers, are eligible to retire early in the 21st century. These retirements will leave a significant gap in the leadership of community colleges. The women in this generation of community college leaders have made great progress in reaching parity with men in leadership positions. The next generation of female senior administrators in community colleges will come from members of Generation X; however, the literature has yet to describe the experiences of this group of female leaders. This research was undertaken to explore the influences, both internal and external, that shape the career advancement decisions and goals of Generation X female mid-level administrators in community colleges in the Southeast. Interpretivism, life course theory, and feminist standpoint theory served as the framework of the study. Two research questions guided this study: 1) How do current Generation X female mid-level administrators in selected community colleges in the Southeast perceive leadership, and what are their career advancement goals? 2) What personal and professional factors do they take into consideration along their career paths and how do they experience this process? This qualitative interpretive study utilized semi-structured interviews of 10 Generation X female mid-level administrators in selected community colleges in the Southeast. The findings of this study suggest that Generation X female mid-level administrators find themselves experiencing paradoxes in both their personal and professional lives. They are communal team leaders, but they feel they must possess certain agentic traits in order to be effective leaders. They are sandwiched between the Baby Boomers and Generation Y at their institutions, working to find a balance between the two. They are well aware of what is needed to develop professionally, but their career goals are relatively undefined other than a general tendency toward leadership and they often seem to move into higher level positions by happenstance. Finally, they praise their spouses for being supportive, yet they have to participate in a "delicate dance" to garner that support. The organizational and relational structures in which these women must maneuver also contribute to these paradoxes. To support the career advancement of these women, several implications for practice are offered. Senior administrators are encouraged to develop formal mentoring programs, foster stretch assignments for employees, seek input before making sweeping structural changes, and allow time for employees to participate in civic activities. Generation X female mid-level administrators are encouraged to participate in stretch assignments to build job knowledge and confidence. They are also encouraged to obtain the doctorate as one means to stand out among colleagues. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]