This paper concerns some self-assessment initiatives in a comprehensive school in Rome (primary and lower secondary school) in 2021 and 2022. In particular, a written semi-structured interview on the well-being and discomfort conditions, developed by a group of teachers in collaboration with the Roma Tre University, and the results of its administration with schoolteachers are discussed. Furthermore, the reflexivity questionnaire ‘When I teach’ designed by Sapienza University of Rome (Botta, 2022) is described and its results are discussed. The results are in line with the ones of other studies (Gozzoli, 2017) and reveal that there are not only important wellbeing factors but also the ones of discomfort to reflect on. Finally, it is emphasized how a self-evaluation initiative in a school that carries out research on itself can become an experience of self-training for its teachers and improvement of the whole school.