The extensive literature on workplace stress, its causes, and the consequences for human health and organizational effectiveness, is being complemented by a growing, alternative emphasis on employees' well-being. However, in education (where well-being is particularly at risk) sustained examples of positive organizational approaches, rather than individuals' stress management, are rare. This article seeks to demonstrate the importance of well-being as a tough-minded concept. Secondly, it presents new findings from research in two schools facing challenging circumstances, which are committed to long-term Well-Being Programmes. The findings accord with inter-disciplinary well-being theory, and offer new commentary on the association between well-being, the management of feeling, and informal learning in the workplace. The research indicates the importance of cognitive attitudes such as non-judgmental openness in schools facing challenging circumstances. Some implications are suggested for educational leadership, for the role of unions, and for further research.