This article explores how collaborative self-study, initiated by experienced challenges and insecurity in new roles, contributes to the professional development of teacher educators. We document how four vocational teacher educators created a free space for self-development in a self-study process of dialogue and collective reflective inquiry. This study was initiated during the 2019/2020 academic year as we facilitated a school-based mentor course for vocational high school teachers. We analyze personal reflective journals written during and after mentoring sessions, group meetings, and throughout the process. Drawing on the self-study tradition within educational research, we examine the dilemmas, challenges, and opportunities this experience presented for our roles as teacher educators. The results indicate that investing time in group meetings established an atmosphere of mutual trust and developed the self-study group as a free space. Furthermore, we show the value of collaborative self-study as a tool for individual and collective self-understanding and professional development for teacher educators. Our experiences indicate that a self-study group must be self-selected to achieve an open and trusting process. Furthermore, the study shows that creating free space in academia is possible but highlights a need for academia to recognize free space and self-study as integral parts of the work culture.