The digitalisation of educational contexts has changed the practice of teaching and learning. In this, teachers have a key role in enacting digital technologies for this purpose and have different opportunities to do so. This article explores how digitalisation can affect teachers by focusing on: (a) how teachers manage to capitalise on digitalisation; and (b) how digitalisation can affect and reconstruct their self-understanding. Two teacher colleagues of English as a foreign language (EFL) in the same teaching team are interviewed and observed. Drawing on the interplay between self-image, self-esteem, job motivation, and task perception, it is shown how the teachers' self-understanding is played out and changes due to the call for digitalisation. Whereas one of the teachers has been able to capitalise on digitalisation in a way that has been beneficial both professionally and personally, the other has felt pressurised by it. A conclusion is that a limited or extended use of digital technologies should not be taken as an indicator of teaching quality.