The digital transformation in education is an ongoing process that was accelerated by the COVID-19 pandemic. In the post-pandemic era, this transformation is still far from complete and remains an ongoing challenge for many educational institutions. Based on the experiences of secondary and higher education teachers, this study offers insightful information about how educational institutions should continue a sustainable digital transformation without repeating past mistakes. Qualitative data was collected in online focus groups using a semi-structured interview guide based on the principles of appreciative inquiry. Respondents are 42 secondary (n = 20) and higher education (n = 19; or a combination of SE/HE n = 3) teachers from three regions in EU-region Meuse-Rhine. In addition to experiences related to teaching, students, and support, the topic of well-being emerged from the interpretative phenomenological analysis. Results show that a sudden change in digital technology noticeably impacts the emotional and mental well-being of teachers. The school’s digital policy is the key concept that aligns teachers’ well-being to digital learning, including facilitating factors such as a clear vision, adequate technical/practical facilities, professionalization, and training while maintaining a social connection with colleagues and students. To stay ahead of impending challenges, this holistic and systemic study emphasizes the importance of balancing different stakeholders’ interests within the complexity of digital transformation as a way to guarantee a sustainable implementation of the appropriate application of digital technology for learning.
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