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Healthy and adaptive strategies for regulating emotions and coping with the demands of their jobs can help school-level leaders mitigate the factors and forces heightening the emotional aspects of their work, stave off the negative effects of work intensification and achieve wellness. As with most individuals in most professions, school-level leaders use several different strategies to manage their emotions and cope with the stresses associated with their work. Some of these coping strategies are associated with positive outcomes including situation selection and exercising autonomy over their workday, talking to colleagues, reappraisal, humour, controlled breathing, exercise and engaging in hobbies outside of work. However, even the most experienced and effective school-level leaders demonstrate a proclivity for engaging in coping strategies associated with maladaptive and negative outcomes. These maladaptive strategies include worrying about events over which they have little or no control, masking one's emotions using expressive suppression, using thought suppression to deal with symptoms of emotional exhaustion, distraction, manipulating the emotions of others as well as use of illegal or prescription drugs, alcohol and other forms of self-medication. This chapter concludes with a discussion of how there can be some overlap between these strategies in practice and how they are classified.