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After 12 years at Phillips Andover, Rev. Anne Gardner joined Harvard-Westlake in 2020 as the school’s chaplain. While prior to Anne’s arrival, Rick Commons had framed the role as an “entrepreneurial chaplaincy,” Anne had no idea how unorthodox it would actually become. Anne spent the first year of the job remote from Los Angeles, and then the second year working with students and adults who were still adjusting psychologically and spiritually to the fear and isolation of a global pandemic. In its aftermath, Anne sees her role as helping community members ask the big questions—such as, “Who am I? How do I decide right from wrong? Whom do I emulate? What gives my life meaning?” In Anne’s case, life was given meaning by two brave and resilient parents—a mother who became a biochemist, and her father a World War II hero and amputee. It was they who inspired Anne’s sense of gratitude and public service, as well as her commitment to a somewhat unlikely career as an ordained minister. Anne admits that as a gay woman, she carries an unusual combination of characteristics for clergy—but that she enjoys leaning into this cognitive dissonance in others, as a way to demonstrate both a common humanity, as well as the many spiritual paths to intellectual and religious leadership. Anne credits both her parents and her Jesuit education as profound influences on her life and career.