The consequences of economic crisis are different from one European context to the other. Based on life design (LD) approach, the present study focused on two variables—career adaptability and a positive orientation toward future (hope and optimism)—relevant to coping with the current work context and their role in affecting life satisfaction. A partial mediational model between career adaptability and life satisfaction, through a positive orientation toward future (hope and optimism), was tested across Italian and Swiss countries. Seven hundred twenty-six Italian and 533 Swiss young people between the ages of 12 and 16 years were involved. Results provided support for the model in the Italian group and a full mediation model for the Swiss one. The data suggest that the context may have an effect on how career adaptability has an impact on general life satisfaction. These results have important implications for practice and underscore the need to support adolescents in their LD process.