The restructuring of nurse training involves the implementation of tools that encourage self-development and empowerment, along with a reshaping of the function of accompaniment during training, which becomes a shared function. This work is part of a psycho-socio-educational approach to accompaniment in self-directed learning and also in the field of practices of health and social work. This study contributes to the identification of the conditions of efficiency of contracting between student nurses, tutors, and instructors. It aims to explore the benefits of a triangular steering of the learning contract centered on the student’s individual project and also the benefits of meetings during training as triggers to a process of self-construction of skills. Moreover, the study aims to identify the effects of contracts on professionalization. Our study reverts to the basic question of learning by contract as a pillar for self-directed learning in an alternating training context. The empirical approach takes into account a qualitative study carried out with fifteen people (tutors, managers, student nurses, and instructors) in three health care facilities and a quantitative study based on seventy-eight first year students, 106 second year students, and forty-seven third year students at the same nursing education institute. The study shows that learning by contract is empowering and professionalizing, if the conditions of learning and the contractual relationship are favorable for the student.