This study is part of a framework that views study abroad programs as an opportunity for experiential and transformative learning. Using a mixed-methods approach with a quantitative multi-wave study, this research examined the relationship between cultural intelligence and the internationalism career anchor – the individual predisposition and desire for international mobility for work. This study considers the role of resilience and intercultural interactions as predictors of cultural intelligence. In addition, we examined the transformative learning process by relating the development of cultural intelligence to specific critical incidents or critical experiences in intercultural interactions that can be considered triggers of the learning process. A sample of 170 outgoing Italian Erasmus students completed a self-report questionnaire prior to departure and another upon return home. The study also included a control group (n = 52) consisting of students from the same university who had not participated in the Erasmus program. The results revealed the positive value of the Erasmus experience, particularly in terms of strengthening the internationalism career anchor, cognitive cultural intelligence and resilience. The results also showed that students’ pre-departure resilience and intercultural interactions with other international students from different countries can explain higher levels of cultural intelligence and the desire to work abroad or take on global work assignments. No significant change across time was found for the same variables in the control group. In addition, the critical experiences reported by students highlighted a strong cognitive and motivational component associated with the Erasmus program. Some practical implications for higher education are discussed.