This chapter presents the case of Arina - a business trainer, career consultant, and expert in managing employee responsibility - who proactively navigates her career in Russia after the political and economic collapse of the Soviet Union in 1990. With this case, we introduce the concept of career reinvention that involves an investment in new knowledge and career plans, as well as a career divestment, encompassing decisions not to pursue a previously attractive career goal. To reinvent her career, Arina pursues various career paths which require important career-related decisions including divesting from previously attractive career opportunities and work-related identifications that are no longer viable in the new economic context. Her story illustrates how to reinvent one’s career through navigating turbulent times and proactively enact one’s environment, creating personal success and employability.