This study investigates how young adults in vocational education perceive risk in regard to their professional futures in East Germany and the United States. It analyzes students’ career aspirations and life plans in both countries and how they cope with uncertainties at the labor market. It further outlines underlying values, beliefs, and attitudes that guide young Americans and East Germans in their planning. Several theoretical frameworks ground this study and comprise the majority of the relevant literature. This cross-cultural comparative case study takes a mixed method approach using a concurrent triangulation design. The inquiry is framed by theories in the field of risk and cultural risk perception, school-to-work transition, vocational education and training, and welfare studies. In both countries, 129 students filled out a questionnaire. Additionally, narratives from nine focus groups and 29 biographical interviews were conducted. A three level analysis of the data was compiled that outlines the themes and categorizes them according to an individual, institutional, and macro-structural level of influence on risk perception in each country. Emerging premises on an individual level were choice, family and career planning concerns, geographical and occupational flexibility, further education and training, and agency. On the institutional level the influence of public career advisement institutions, teachers, parents, peers and friends was outlined. On the macro-structural level unemployment, political welfare reforms, the vocational education and training system were themes that have been of concern among the East German population. The dissertation also offers a comparative analysis of the data. This study reveals that young adults in East Germany are highly concerned about their occupational futures and tend to be pessimistic about current welfare reforms. They hold on to the idea of a standard biography and try to make strategic career plans. Their counterparts in the United States are highly optimistic about their futures, expressed little concern about labor market policies, but also appeared to be short term oriented in their life planning in order to remain flexible and mobile.