As administrators in K-12 settings retire, it is often not apparent why they chose to retire, particularly if the retirement was sudden or there was unusual turnover in a geographic area. Each administrator has experiences unique to his or her situation. In this qualitative research study, the experiences of a group of K-12 administrators in a South Atlantic region who were making the decision to retire were explored. In addition, the purpose of this study was to identify and explore strategies that these administrators used to consider the decision of whether or not to retire. The results served to expand the body of knowledge in professional studies in education, specifically, educational leadership, and helped to close a gap in the existing literature concerning the subject of retiring K-12 administrators. In the study, the following research question was addressed: What experiences contribute to K-12 administrators' decisions to retire? A basic qualitative research design was chosen, as it allowed for the use of one-to-one, personal interviews as a data collection method. Twelve administrators were interviewed, and the results revealed four themes that constituted reasons for considering retirement: compliance issues, including state mandates; financial considerations; external and internal issues, including time to retire and health challenges; and post-retirement plans. Strategies employed by the participants when considering retirement included utilizing human resource personnel to evaluate retirement options; financial advisors to evaluate current financial and retirement status; and personal assessment of fatigue levels, family situations, and desired post-retirement lifestyles. [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.]