Housing and residence life as a functional area serves as a major entry point for careers in higher education and student affairs. With the majority of annual job postings within entry-level, live-in housing roles, the future of the field may well be predicted in these high-impact, high-turnover positions on college campuses. As these functional areas continue to struggle to find themselves fully-staffed throughout their academic year cycle, the impact on both the student experience and organizational health is impacted. This study utilized an interpretive phenomenological approach to explore the experiences and feelings of those entry-level, live-in housing professionals who chose to leave their position mid-year to take another position within a different function of higher education and student affairs. In focusing on an off-cycle transition the narratives pulled from those with a stronger motivation to leave the function of housing and residence life, which highlighted the cause for attrition. Twenty semi-structured interviews were conducted with qualifying participants to better understand the essence of their experiences of making this career transition decision. Much of the existing research follows the path of professionals who chose to leave the field of higher education and student affairs entirely. This study adds to the literature both the narratives and experiences of those professionals who have chosen to leave a career in housing and residence life but still remained engaged within the field of higher education and student affairs. [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.]