This multi-case study explores the lives of six former preK-12 teachers and their health and well-being during and after teaching. Using the framework of self-care, the purpose of this research was to investigate how teachers' health, well-being, resilience, and other internal characteristics intersect with external factors of teaching and schools; accelerating teacher stress, burnout, and attrition. Through four of these former teachers' voices, we learn from lived experiences how already deteriorating schools and teacher working conditions were further exacerbated by the COVID-19 pandemic. The major themes revealed included the ineffectiveness and difficulty in early teaching careers; negative impacts/barriers to effective teaching and self-care; COVID impacts on teaching; school violence impacts on teaching; positive affirming experiences in post-teaching life; and finally issues/suggested policy changes. To address these negative impacts on teachers and the school community, leisure programming is presented as a pathway to personal development, to be paired alongside professional development. Opportunities for leisure, as part of a comprehensive employee health and wellness plan, are offered to fully support and sustain the whole individual, including multiple avenues for self-care. [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.]