Childhood shyness plays an important role in terms of learning and socialization and can have profound effects on individuals’ thoughts, feelings, and behaviors that can carry over into adulthood. The present study investigated how self-identified childhood shyness might influence elementary school teachers’ current perceptions of shyness among their students. Participants were 14 elementary school teachers. Interviews were conducted over the telephone and ranscribed for content analysis. Analysis revealed themes of social factors,personal factors,and relating to shyness that contributed to childhood shyness. Moreover, these experiences of childhood shyness appeared to contribute to teachers’ current perceptions of shyness (among teachers who self-identified as shy children). Implications for future research and holistic educational practices are discussed.