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Leaders are often wounded in practice, most often psychologically. This qualitative three-part interview study explored how six superintendents describe and understand a wounding experience—defined as a serious conflict, dilemma, or critical event in leadership practice that has a profound impact on the person. It addressed a gap in educational research by providing insights into how superintendents described, processed, and made meaning of their wounding experience and how they learned, healed, or recovered. They described wounding as originating from doing the right thing for students, conflicting with core values, and being blindsided. The study concluded that wounding is inevitable and often undiscussed, highlighting the need for supportive forums for leaders to voice, process, and heal from their experiences.