Teaching is a profession with an extremely high level of turnover, especially among new teachers (See et al., 2020). Research supports that there is a correlation between job satisfaction and teachers choosing to stay or leave (Lane et al., 2019; Shibiti, 2020a). This qualitative case study sought to understand the experiences of teachers and administrators in regard to leave time, job satisfaction, and motivation in small rural Missouri public schools. Interviews were conducted with current teachers with six to ten years of classroom experience and current administrators with at least three years of administrative experience to gain an understanding of the participants' firsthand experiences with leave policy. Participants shared stories and insights of how leave policy impacted morale at their school, as well as how specific factors influenced their decision to stay or leave their current position in their school district. Additionally, teachers and administrators gave feedback on the most significant factors associated with job satisfaction and motivation within the educational realm. The study produced four overarching themes directly influencing teacher retention, morale, job satisfaction, and motivation in the workplace. [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.]