The purpose of this article is to investigate how an innovative collaboration between one lower secondary school, upper secondary school and industrial company can contribute to a more informed educational choice (vocational vs. programme for specialisation in general studies) among today’s youths. Eight lower secondary school students, five upper secondary school students, one employee in the participating industrial company, one teacher from lower secondary school, one from upper secondary school together with the section leader for vocational education programme (upper secondary school) have been interviewed. Thematic analysis has been used to analyse the data. The theoretical perspectives undertaken are self-determination theory and social-cognitive theory. Findings highlight that the study’s innovative collaboration gives youths an essential insight into the future school- and work practices. During the collaboration, the youths learn about the competence needs for future work life, and gain knowledge about their own learning potentials. Practical experience, new ways of collaboration, work centred communication, engaging and challenging training situations, experience of meaning, together with responsibility taking for own and other’s learning contribute to a more qualified education choice. We find that the pupils in lower secondary school experienced this innovative collaborative practice to produce more autonomous than controlled motivation, and more positive outcomes in terms of both behavioural, cognitive and affective dimensions of learning, at school.