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Though multiculturalism in American schools is a popular academic topic, research has been mostly concentrated on policy and pedagogy. There is, relatively, much less known about the individuals who work at these institutions. This dissertation project aims to investigate the transformative experiences and relationships that foreign-born multicultural educators attribute with encouraging them to work in countries besides their birthplaces. Framed as a narrative-based inquiry, study participants participated in three interview sessions, describing the relationships and experiences that encouraged them to make such a life-changing decision. Their stories were combined with autobiographical information from the researcher to cooperatively weave a narrative that emphasizes transformational learning as a primary driver behind the immigrant experience. Transformative learning theory, developed by Jack Mezirow, is a framework that contemplates the decision-making, sense of self, and reflection foundational to dramatic changes in one’s life, identity, and social roles. Participants were purposively sampled from a private trilingual immersion school with foreign-born instructors. These educators exemplified a growing diversity that currently characterizes the average American school, whether private or not. This research project aimed to investigate the transformational aspects of their journeys and contribute to the epistemological gaps in transpersonal spaces of multicultural education.