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School-level leaders are suffering. They are experiencing a well-being crisis after years of working long work hours, managing an unrelenting workload, and navigating shifting policy contexts. School leaders that are experiencing work intensification and highly stressful work environments can suffer personal and professional consequences. On a professional level, school-level leaders are immersed in intensified work environments that mute the power and potential increasingly associated with their role. This chapter describes challenges that threaten school-level leaders' productivity, job satisfaction, happiness and well-being, such as work intensification, burnout, stress as well as loneliness and isolation. In these ways, the emotional aspects of their work can influence school-level leaders' ability to lead happy and healthy lives, while also having the supplementary effect of making the position less attractive for the next generation of school leaders. Research conducted in jurisdictions around the world is discussed throughout the chapter to demonstrate that the well-being crisis experienced by school leaders is an international phenomenon. I also use this discussion of the challenges facing contemporary school-level leaders to encourage them to reconnect with the reasons why, and the emotions they felt, when first pursuing a position in K-12 school-level leadership.