In an effort to understand the positive and negative experiences that principals encounter as they navigate through their first year of administrative duties at the middle school level, this research study examined what events happened during their first year that encouraged the individual to stay in the position or discouraged the individual to leave the position. This study focused on problems and difficulties that arose, specifically associated with the middle school setting. To accomplish this study, three first year middle school principals were interviewed multiple times throughout the year. By collaboratively working with these participants in a phenomenological study, the researcher was able to empathize with the lived experience of each participant and come to know another person in order to check whether his experience of the phenomenon corresponded with another's experience (Husserl, 1931). The information from this study will add an important perspective and voice to the literature, that of three beginning middle school principals experiencing their first year of the principalship. Interpretation of the events that occurred during this first year of administrative duties will help prepare future middle school principals or help mentor beginning principals in order to overcome possible obstacles that are presented during the first year of leadership at the middle school level. With this information, professionals dedicated to improving educational leadership will be able to develop strategies that address these concerns, thus increasing the retention of beginning principals in middle school administrative positions. [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.]