With Generation Z entering the global workforce, it has become increasingly important for companies to understand the traits, career aspirations, and expectations that drive their career choice. This paper explores the main drivers of career choice among Gen Z students, which are related to the elements and values they expect regarding jobs. The research included 119 students enrolled in undergraduate or master’s programs at two universities in the same field of study but situated in distinct Central and Eastern European countries, the Republic of Slovenia and the Republic of Serbia. Data collection took place in April–May 2024. The results show that the main drivers for career choice in Slovenia and Serbia are Life Balance, Freedom, and Expertise, but in different order. At the same time, Organization Membership and Entrepreneurship are the lowest-ranked values in Slovenia, and Entrepreneurship and Management are in Serbia. The paper further examines the influence of national cultures on the identified career expectation themes among students in Slovenia and Serbia. By exploring Gen Z’s expectations regarding careers, the research presented in the paper could give valuable insights for businesses to shape their strategies to meet this generation’s evolving needs and aspirations, ensuring pathways to meaningful and sustainable careers.