The purpose of this research was to highlight the importance of studying and promoting well-being to help manage stress and prevent burnout among school principals, examine potential gender disparities, and to consider implications for future practice. Grounded in a positive psychology framework, this study examined the correlations among school principals' workplace well-being, perceived stress, self-compassion, and intent to remain in their roles using a non-experimental, descriptive survey method. In Washington State, 124 school principals responded to an online survey over a span of 11 weeks. Descriptive, correlation, moderation, independent t-test analyses were performed on quantitative data, and qualitative data was analyzed through inductive content analysis. Results revealed that principals, although reporting moderate stress levels, exhibited suboptimal levels of workplace well-being and health. Well-being was a strong correlate of whether principals intended to remain in their roles the following year. Stress demonstrated strong negative correlations with workplace well-being and self-compassion, emphasizing the crucial role of stress management in fostering well-being. Self-compassion had a statistically significant relationship with well-being but did not moderate the effects of stress on well-being, nor did it have a statistically significant relationship with principals' intent to remain in their position. Gender-based differences were negligible; instead, qualitative findings unearthed more universal multifaceted stressors faced by principals, shedding light on the complex relationship between occupational stress and well-being in this sample. Implications for future research and practice based on the study findings are further discussed. [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.]