This chapter addresses issues of agency and structure in career-decision making. We follow and reflect on the career path of a Portuguese manager who leaves her country during the financial crisis to pursue her career as a self-initiated expatriate in Germany. We use multiple constructs and theoretical frameworks to understand her career choices, namely career success, employability and boundaryless career attitudes. These can help understand several elements of her unique experience but, by emphasizing the individual agency, would not be complete without a broader look at the contextual elements. By adopting a Brain-Drain/Brain-Gain perspective, and by carefully considering the institutional characteristics of the two countries, we can more fully understand how career choices are made within the array of opportunities available.