Due to the taxing and cruel nature of the teaching profession, purely entering this profession may increase one’s probability of experiencing mental health difficulties. Educators are constantly bombarded with demands from various role-players within the educational system, creating unappetizing environments for them to function in. This is reflected in educator attrition rates, where the outflow of educators seems to outweigh the influx of educators. Despite the common difficulties experienced by educators, some even manage to flourish. Unfortunately, little is known about the prevalence of educator well-being, its antecedents, and outcomes from a health-promotion or positive functioning stance (especially within the South African context). Therefore, a cross-sectional study among 258 secondary school educators from two local districts was conducted to assess the prevalence of work-related well-being, establish antecedents of work-related well-being, and pinpoint outcomes related to work-related well-being. Almost half of the participants fell within the moderately mentally healthy categorization, followed by flourishing individuals. A relatively small percentage of the sample languished. Person-environment fit and positive practices were associated with work-related well-being, while work-related well-being was associated with in-role performance, intention to leave, and organizational citizenship behavior. To ensure the retention and performance of educators, create appealing work environments!