Cultivating preservice teachers' "shutaisei" has been the focus of Japanese university-based teacher education since the late 1990s. This article contains the self-study of three teacher educators at different Japanese universities. All three of us believe that helping students cultivate their "shutaisei" should be an important part of our teaching practices; however, framing "shutaisei" and pursuing it in practice poses complex dilemmas. In this article, we explore our individual understandings of "shutaisei's" meaning in theory and practice, and reflect on how and why we considered it in these ways. We discussed our practices every two weeks online; all the conversations were videotaped and analyzed. Ultimately, through this self-study, we (teacher educators) found: (1) We had defined what "shutaisei" means based on our own educational experiences; and (2) We had suggested our own "shutaisei" to the students without being aware that it is based on our own educational experience. Teacher education institutions, we recommend, should provide opportunities for faculty members to explore themselves and their practices.