The purpose of this study is two-fold. The first purpose is to explore how native English-speaking teachers in Korea describe constraints of their teaching experience in a different culture. The second purpose is to attempt to analyze these teachers’ perspectives on what kind of support proves to be helpful during the initial teaching experience. By analyzing collected data from in-depth interviews and focus groups during threemonth period, this study tried to capture certain cultural patterns and operational principles underlying the native English-speaking teachers’ meaning making of their teaching in a different cultural context. The overall findings from this study shed light on the direction of future research in several ways. First, research participants in this study point out the importance of the teachers seeing themselves developmentally. It was also posited that the process of becoming a teacher in a different culture is somewhat idiosyncratic, however, strongly affected by contextual factors, especially by the role of the native cooperating teacher and the role of the mentor. The results of this study were discussed in a way to generate practical suggestions for improving the support system for the native English-speaking teachers.