This paper describes a longitudinal, collaborative case study, made in the framework of the project Students' Ownership of Learning (SOL) during one academic year with one vocal teacher and two female students. The aim of the study was to relate the interaction between the teacher's and the students' intentions and expectations to the institutional level as well as to the rules and "real-life" practice of the musical profession that the students are trained for. In the study, one-to-one tuition in higher music education was theorised as a culturally and historically grounded activity system consisting of relationships between musicians, instruments, music-making traditions and audiences. The concept of contradiction was used as a tool when analysing individually experienced obstacles for musical learning. The results describe how learning obstacles such as conflicting views on the purpose of the activity may be articulated, confronted and transformed into options through collaborative work. By linking the individual and collective levels of knowledge and by using professional practice as a developmental transfer, all aspects of the "conservatoire tradition" may be seen as holding potential for development and expansion.