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Today’s school leaders face a daunting task: be highly effective systems managers, strong instructional leaders, and engaging community partners, all with reduced resources. With the onset of the COVID-19 pandemic, school leaders added health care professionals to their list of duties. In March 2020, the District closed all of its schools and moved to an online virtual learning environment. For many school leaders, this work reality was exhausting as they tried to balance professional responsibilities and personal life. The District invested in Wellness Wednesdays for Administrators, a protected online environment where school administrators engaged and deepened their wellness and self-care practices. Participants learned strategies to aid in their wellbeing and mitigate the negative effects of stress, anxiety, and fatigue.