One of the challenges facing community colleges in the United States is the looming retirements of executive/senior-level leadership, particularly the president, on a wide scale. This study explored the career aspirations of executive-level leaders within the community college using Social Cognitive Career Theory as the conceptual framework. Within the context of a three-person collaborative dissertation project, a mixed methods case study approach was utilized for the research design. It first examined the perceived and preferred organizational culture(s) by administering the Organizational Culture Assessment Instrument (OCAI). Building upon results of the OCAI, interviews with executive-level leaders explored how personal and institutional factors impact their aspirations of to ascend to the community college presidency. The findings of the research indicate that affecting change, being asked, and the desire to help are personal factors of influence that motivate executive-level leaders to seek the role of community college president. On the other hand, age, family, and potential work-life imbalance might dissuade executive-level leaders from seeking this role. The study reveals that organizational culture (the "culture of caring") and formal leadership development programs are positive factors of institutional influence. Institutional factors that dissuade executive-level leaders from seeking the community college presidency are politics, the state of the institution being led, and the unknown. This study advances the field of educational leadership in that a number of personal and institutional factors are adduced that influence the aspirations of executive-level leaders to progress to the community college presidency. The findings identify the need for research across multiple institutions and the need to expand Social Cognitive Career Theory to include personal-cognitive barriers of race and gender. [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/en-US/products/dissertations/individuals.shtml.]