The present study is among the first that has investigated how teachers’ perceptions on quality of school leadership, work-related meaning in life, and optimism explained the psychological well-being of 509 kindergarten teachers in Hong Kong, China. Structural equation modelling showed that teachers who perceived better perceptions on quality of school leadership found more work-related meaning in life, and were higher in optimism, while work-related meaning in life positively explained optimism, only optimism mediated perceptions on quality of school leadership and psychological well-being. Findings implied the importance of the reciprocal relationship among perceptions on quality of school leadership, work-related meaning in life, and optimism. School management should pay attention to such relationships when designing school plans and teacher training programs to enhance teachers’ psychological well-being. Copyright © 2023 The International Society for Quality-of-Life Studies (ISQOLS) and Springer Nature B.V.