This qualitative study explores the life history of four immigrants from diverse cultures, who have effectively navigated cultural differences and attained high-level leadership positions in Canada. The leaders’ life stories highlight key experiences that have influenced their identities, that is, the distinctive characteristics that are the source of their individual self definition and self-respect. The purpose of the study is to understand how social identity influences immigrants’ sense of personal agency and their capacity to shape individual potentialities into personal abilities. The study is situated in the leadership field within the multicultural Canadian context. It is grounded in my personal experiences as an Iranian-Canadian immigrant and guided by multidisciplinary literature on leadership, culture, identity, and motivation.Globalization, economic interdependence, and growing cross-national mobility have changed the face of the Canadian multicultural society. The clash of world-views, values, and life styles have become unavoidable, with arguably all Canadians experiencing the feeling of being “other” in their interactions with members of other cultures. Within the new Canadian mosaic, cultural consciousness is on the rise leading to increasing ethnic distinctiveness. It has become a factor distinguishing individuals by their differences as well as grouping them together by their similarities. Living in a multicultural environment as an immigrant has implications on issues of identity, but these implications have not yet been thoroughly explored. Much of existing cultural research is based on national orientation and contentious dualism (e.g., individualism and collectivism). But, cultures are dynamic and diverse. Understanding cultural constructs at the individual rather than the national level demonstrates the complexity and variability of individuals in the exercise of personal agency and the construction of identity. Through sharing and understanding the experience of four immigrants in leadership positions across diverse organizations, researchers may learn about immigrant challenges and ways these four individuals reconcile differences and conflicting cultural values. The resulting practical implication is (a) increased self and social awareness for immigrants with high potential for leadership, (b) enhanced multicultural knowledge for current organizational leaders, and (c) improved interpersonal relationships within a broad multicultural community.