This report discusses why Japan continues to struggle with and appears on the surface to be reluctant to embrace the English language as a medium to conduct business and indeed tourism as opposed to their South East Asian neighbours. The topics covered were the historical context of Japan's isolationist policy, Japan's educational system, and their English educational policy. In addition, I compared and contrasted Japan's test performance and/or results with other South East Asian countries based on secondary source data from three recognised international English proficiency tests TOEIC, TOEFL and IELTS. Next, I discussed the economic implications, due to the lack of an English speaking workforce. Finally, I included a case study, which focused on a Japanese company who adopted English as the company language.