Efforts to tackle educator stress should balance self-care with demands for changes to the unjust systems that cause the stress. To illustrate how coaching can ensure that the steps educators take are equitable and include perspectives and voices of educators who have been historically marginalized, the author has created a composite story about coaching with an urban high school principal. This story and reflections that follow are drawn from multiple coaching conversations with BIPOC (Black, Indigenous, and People of Color) leaders. As the story shows, there are no clear-cut answers for solving the crisis in educator stress and mental health, but progress can be made by recognizing and validating the challenges, supporting self-care, and identifying steps toward systems change, and doing so with an inclusive and culturally responsive lens.