Teachers in Puerto Rico are more than just educators--they serve as mentors and guides and play a significant role in shaping their students' lives as they lead them towards transformative changes. As teachers consider transitioning from their jobs to other objectives outside the academic field, they must prioritize their students' best interests. Retirement is an inevitable phase in teachers' lives and can be a challenging process. Teachers must be creative in their approach while evaluating which ideas work, avoiding financial problems, and prioritizing their mental health. This qualitative research case study focuses on the economic remuneration Puerto Rican teachers receive for their retirement and its possible consequences concerning poverty, stress, and mental health. It is crucial that leaders from the government and educational organizations understand the mindset and reasoning behind teachers' decisions to retire. A deeper understanding of teachers' retirement-related decisions will ensure continuity in organizational processes and lead educational institutions to a level of excellence and a culture of collaboration. [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.]