This grounded narrative inquiry study analyzes the self-selection transitional career motivations by California Community College chief fundraising executives when considering the pursuit of a California Community College presidency. A theoretical research framework is an approach that integrates narrative inquiry in the development of the grounded theory. Design influences are crafted in as lenses from Schlossberg's "transition theory," McClelland's "human motivational needs theory, and Thematic Apperception Test" (TAT). The study has an exploratory emphasis on perceived career factors that motivate chief fundraising executives who are typically considered non-traditional or non-academic candidates when pursuing a college presidency. Research questions explore the unknown reasons why chief fundraisers who have the skill sets that closely align with the college president rarely if ever transition to becoming a college president. This study is focused on the California Community College system and their senior chief fundraisers. Recent literature indicates fundraising is an increasingly important skill for a college president, yet only about 4% of community college presidents have had a career history in fundraising, and my research indicates that it has never happened in California. This gap in the literature is why this research has emerged. Ten chief fundraising executives in California Community College were interviewed about their transitional career considerations and perceptions relative to the pursuit of a community college presidency. Three themes emerged from the narratives. They are "antiquated system," "lack of position desirability," and "not valued." These themes became the relevant barriers chief fundraisers depicted as halting the transition process to become a president. A grounded theory was developed, named the Community College Chief Fundraiser Career Transition (CCCFCT) Model of behavior to explain the career transition process. [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.]