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In this chapter, we explore how higher education institution (HEI) leaders perceive the relationship between their international background and their commitment to and vision for internationalization. Our 10 Canadian HEI participants thought there was a direct link between their international backgrounds and commitment to internationalization. While all spoke of the benefits of internationalization, some viewed internationalization through an ethical, socio-cultural lens whereas others privileged internationalization’s instrumental values. We point to tensions facing some leaders in reconciling their ideal visions of internationalization with neoliberal pressures facing HEIs in a global era. We demonstrate the importance of attending to the inter-relationships between broader socio-historical drivers of internationalization and the personal biographies of those charged with advancing internationalization agendas. Our findings lead us to develop a new theoretical concept, which we term the ‘internationalization imaginary’, to understand the interplay between the individual, local, national and global forces shaping internationalization in higher education.