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New educational leaders must learn to approach their new place of functioning with only partial understanding of what their new role entails and plenty of unstated expectations to fulfill, customary protocols to follow, and constituencies whose points of view are key to the new arrival’s long-term success. Using complexity theory asset-based leadership as frameworks, this research unpacks stories of bicultural leaders in the borderland area of the United States as they begin their journeys as new school leaders in their communities. Findings demonstrate layers of complexities in sociopolitics, the need for navigational capital among these new school leaders, and sociocultural anchoring needed by all individuals within their unique characteristics and diversity of experiences.