In the paper, we propose a new approach to vocational guidance of school children based on classification of pupil wishes between given professional trajectories, which are presented by profiles of successful professionals. Both wishes and profiles are replies in free text form on a questionnaire proposed by skilled psychologists. Such an approach avoids the well-known deficiencies of traditional methods including binary questioning, talks about concrete professions, and interviews with school psychologists. We use the simple terms selection for preprocessing and the traditional method of voting for classification. The mentioned procedures are discussed and the proposed approach is preliminary checked on invited specialists. This joint Russian-Irish research has been carried out with Moscow school children (2 schools) and Moscow specialists (2 trajectories). The results of presented pilot study look very promising. It is the basis for current applied research in Moscow and the future activities in Dublin.