Many people involved in international education, including students and parents, engage in a stepping-stone discourse that identifies English-medium learning in non-Western countries as a preparatory stage for postsecondary education in Western destinations, with the ultimate goal to secure competitive employment. The present study examines how this hierarchical model applies to Japanese English learners who are positioned in an ambivalent Japanese context where conflicting and emerging English study values and practices coexist with one another: the limited societal need for practical English in employment, the entrenched ideological idealisation of 'native' English speakers from/in the West, and the growing profile of English study with ASEAN teachers online or in ASEAN countries. Analyses of numerical and written data from 85 Japanese who have studied English both in ASEAN countries and in the West reveal that a flexible, two-way mobility derives from their privileged status as persistently novice English learners on the one hand and their divided self-identity -- either as an Asian non-native or an advanced Westernised citizen -- on the other. This study provides both pedagogical and research implications regarding Japanese students' divergence from the degree-seeking international student population.