Women remain a minority in the college presidency, representing only about a quarter of all presidents. Using interviews, document review, and a researcher's journal, this qualitative study examined why women choose to pursue or not pursue presidencies of small- and medium-sized, public and private, 2-year and 4-year New England colleges. It included interviews with 11 presidents, 4 women who decided not to pursue presidencies, and 4 search firm consultants. The semi-structured interviews used the Critical Incident Technique and focused on the decision-making process around applying to a presidency. Text analysis and coding used a narrative approach. A critical feminist lens helped explore how more women might move forward but also how organizational structures might prevent women's desires to advance. Interviews revealed that mentors and family played critical roles in women's decisions to pursue presidencies, and lack of conflict with a spouse's career often facilitated the move to a presidency. This study concluded that women's expanded notion of ambition--one that aims for a fit between a position and overall career, family, and life goals--shapes how they make decisions about specific job opportunities. It may also, however, obscure how boards and search committees understand women's ambitions, preventing full recognition of strong candidates. Recommendations for women aspiring to presidencies included valuing their own leadership definitions, making ambitions clear to their networks, working with multiple mentors, discussing ambitions with family, and pursuing roles even if they do not meet all qualifications. Recommendations for boards of trustees and hiring committees included actively supporting presidents, clarifying expectations of presidents' spouses, and understanding how women talk about their ambitions. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]