Through anthropological analysis, two professors—one Mestiza (Apache and Spanish American), one Northern-Western European American (Danish, Swedish, German, French, English, and Irish), and six Native American educational leadership doctoral students offer storied sketches of three college professors on intersections of culture and college teaching. Professors took part in a year-long culture and teaching faculty development project and engaged in cultural introspection to understand how their values, identities, and cultural origins influence their teaching and interpretations of students. Researchers used open thematic and metaphorical analysis of published cultural autobiographies, teaching observation notes, and interview transcripts for each professor to develop storied sketches of their meaning making of culture and teaching. Professors’ cultural self-reflections yielded original insights about teaching across cultures. Authors share paths forward for culture and teaching introspection and for developing teaching across cultural strengths and ways of being.