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The problem this study investigated was high rates of school leaders’ work-related stress results with mental illness and death. The primary objective of the study was to investigate the influence of work-related stress on emotional and psychological well-being and performance of school leaders in Vulindlela Circuit.  The study was premised within interpretivism, and we used interviews qualitative technique, to elicit data from 25 secondary school leaderships about their reflections and experiences with work-related stress. The interview transcripts were analysed using NVivo version 14, a program for qualitative data analysis, analyzing the reoccurring themes and patterns of the study, supplemented with narratives. The study discovered that role conflict, role ambiguity, and overload were common workplace stressors affecting the emotional and psychological well-being of school leaderships. The findings are important because they will serve as awareness and mitigation of school leaders’ work-related stress. The study recommends the rolling out of tailormade wellness programmes that will promote mental wellness, and support well-being and stress-reduction techniques through greater task clarity. This study contributes education research on school leadership workplace stressors in Vulindlela Circuit and larger South African context, by laying the groundwork for future studies on interventions to improve school leaderships' performance and well-being.