This contribution gives an overview of the specific demands and opportunities of the transition from compulsory school to vocational education and training in Switzerland. It argues that structural and psychological factors are important to understand inequalities of success in this transition. The results of empirical studies are presented which show that factors regarding personality, social support, and individual engagement in the career preparation process are important factors promoting interindividual differences in the development of career adaptability and congruent career choices prior to this transition. Implications for counseling practice are presented.