Based on in-depth interviews with 20 teachers in Singapore and a subsequent survey of 316 teachers, this essay analyses the sources of teachers' work stress and ways of coping. We propose to conceptualize stress and coping as different but related phases of human adaptation. Stress is constituted by threats to what is ultimately valuable to a person as a self in that it hinders and obstructs the consummation or completion of behaviour. Coping requires not only direct action of problem-solving but also pilliative action, which entails finding a perspective from which to re-affirm self as a person. This perspective usually evolves out of intimate and personalized social relations.