The instability resulting from major changes in recent decades has fostered a climate of uncertainty and risk that has had repercussions in terms of unemployment, social inequality, and precariousness. To cope with this phenomenon, especially in the context of career transitions, individuals have had to activate multiple psychological resources. In particular, these resources are required in the transition from academic life to the world of work and in the propensity and courage to make certain choices. In our study, we examined two main hypotheses: the mediating effect of courage and proactive personality in the relationship between career adaptability and university satisfaction in a sample of 657 (336 Italian and 321 Spanish) psychology students attending their final year of studies; through a multigroup analysis, the comparison of the two different subsamples, coming from different cultural contexts: Italian and Spanish. The results suggest important differences between these two groups.