There is an increasing trend in attrition, staff shortages, and compensation claims in education. Thus, there is a growing need to figure out what leads to burnout and what increases engagement in teachers. While most focus has been on the conditions of the workplace this book claims there is also a need to understand teachers’ workplace orientations and coping strategies as predictors of well-being. First, it draws together thinking on self-beliefs, motivation, and stress and coping to provide a comprehensive theoretical framework. Second, it follows a large group of teachers over two time periods, providing empirical support for the claims of this framework. The findings indicate the central role of self-worth and how it is enhanced or threatened in the teaching workplace. It also notes that teachers’ motivation orientations are critical in determining teacher burnout and engagement. Using the work of Martin Covington, four groups of teachers are identified– success-oriented, overstrivers, self-protectors, and failure accepters – each with different implications for theory and for schools and their leadership.