This chapter argues for a rethinking of the role of English language educators. There is money in English language teaching, but an attitude of indifference that English language educators should best focus on the usual business of English teaching alone is not enough in the twenty-first century. The times demand they go beyond their roles as mere transmitters of linguistic and cultural knowledge. To shed light on deeper societal issues challenges the notion that social-cultural and economic entitlement is English language education’s true and primary value. This chapter discusses cases from an Asian perspective, highlighting the transformative journey of non-native English language educators and their students as changemakers. Transcending the traditional boundaries of the English language learning classroom is possible. It can also be most meaningful, especially in appreciation of the historical and geopolitical dynamics of the times.