Both cognitive and socio-cultural traditions have traditionally theorized learning in terms of processes of progression within single communities. Since 1995, educational scholars have started to focus on learning as a horizontal process of boundary crossing between multiple communities. Problematic in this approach is that boundaries are often analytically laid out on system level, without explaining whether and how boundaries relate to discontinuities at the level of a learning process of an individual student. What is needed is theoretical elaboration on how an individual learner can be simultaneously part of one and another practice. By drawing on a dialogical approach to Self we intend to theorize learners as participants of practices and transcendent selves. Doing so, we point out that boundaries are dynamically evolving discontinuities that mediate or obstruct potential hybridizations of school and everyday life experiences in learning