Through life histories of the Japanese tour guides, this chapter examines how the image of “magnificent nature” in Canada was tied to a proliferating discourse of freedom in contemporary Japan, and traces cultural translations of work and company. Many of the guides’ narratives corresponded to the powerful discourse of escaping Japan and liberating oneself from the corporate system, circulated since the late-1980s. Neoliberal corporate re-structuring intensified throughout the 1990s, stimulating debates over work and company. The co-existence of competing notions of work—as an activity of personal satisfaction and social contribution, or as merely a means to pursue personal satisfaction outside work—confused many workers and motivated some to leave their company and Japan simultaneously. The chapter examines how those who escaped the corporate system, while dreaming of freedom from old communal ties and living in magnificent nature, made themselves transnational flexible laborers.