This chapter explores how the long-term impacts on the professional development of 50 years of US study abroad in Japan are related to the host country of Japan, host region of Asia, and the world. The findings of the mixed-method study confirm the commonly held notion of study abroad fostering professional bridge leaders between the home and host country and individuals ready to work in a global world. Most notable, the empirical findings revealed that the study abroad host country acts as a gateway to the host region of Asia in terms of career trajectories. The study abroad experience influences participants to be professionally mobile, both temporarily and permanently, across geographical borders to Japan, Asia, and the wider world. Moreover, they engage with these dimensions in their professional experiences at home in the United States. Most notably, historical, gender, and patriarchy contexts influenced career trajectories by pushing and pulling them from career opportunities at home in the United States and abroad in Japan, Asia, and the wider world.