As higher education tries to reimagine its value in the post-pandemic world, professional live-in staff members are fleeing from their positions at a higher rate than new professionals are entering the field. These professionals are expected to work through challenging issues, with minimal training, experiencing secondary trauma, while working in a complicated living environment that can impact the professional's personal life that cannot be made up for in any salary or benefit. Institutions must find opportunities to balance these responsibilities with resources and services that prioritize the well-being and sense of belonging of the live-in professionals. This study explored the lived experiences of live-in professionals at small colleges and universities in Massachusetts and uncovered the unique challenges that these professionals face daily. The study examined the staff's perception of their job responsibilities with their realistic experiences in their roles. Burnout, lack of separation of personal and professional lives, and limited professional development and advancement opportunities were highlighted by the participants as contributing factors for attrition. The participants also highlighted the unique connection of the responsibilities of their role on campus and the requirement to live on campus in these accommodations while navigating typical life milestones such as relationships, families, and other personal goals in a time of increased compliance, evolving student issues and needs, and the regular use of technology in their personal and professional lives. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]