This study uses a qualitative approach and bidirectional design to explore the unique intercultural adjustment challenges that Korean and Canadian self-initiated expatriates (SIEs) experience in each other’s workplace. Through semi-structured interviews we draw upon thematic analysis to surface unique cross-cultural challenges finding that a ‘one-size’ fits all approach to understanding SIE adjustment is overly simplified and omits contextual considerations. Canadian SIEs struggled with issues related to power distance, collectivism and communication styles, whereas language barriers, individualism and hierarchical differences were major challenges for Korean SIEs. We apply our findings to previous conceptual models of cross-cultural adjustment and discuss three criteria: size of cultural gap, direction of immigration and unique contextual factors as necessary for understanding the intricate dynamics of SIE and host-country national relationships. Implications and limitations of this study are followed by recommendations for future research.