The health of the teaching profession is essential for the innovation and productivity potential of our young people. Teachers are faced with preparing young people for an unknown future, with the reduction of manual tasks and an increased focus on people skills, problem-solving, and creative thinking. Teachers are critical in helping students achieve, belong, and develop socially and emotionally. But how well prepared are teachers and other school staff for shifting conditions, and how satisfied and productive are they? The reality is that many teachers, leaders, and school staff are struggling. Drawing on two research studies, this chapter explores experiences of staff wellbeing. Findings indicate that for young people to be well, to achieve at school, and to be prepared for the future, teachers must also be well. Strategies for supporting teacher wellbeing and implications for the future are discussed. A well-educated population is key to a nation’s prosperity, peace, and human flourishing.