Debates concerning digital automation are mostly focused on the question of the availability of jobs in the short and long term. To counteract the possible negative effects of automation, it is often suggested that those at risk of technological unemployment should have access to retraining and reskilling opportunities. What is often missing in these debates are implications that all of this may have for individual autonomy understood as the ability to make and develop long-term plans. In this paper, I argue (...) that if digital automation becomes rapid, it will significantly undermine the legitimate expectation of stability and consequently, the ability to make and pursue long-term plans in the sphere of work. I focus on what is often taken to be one of the main long-term plans, i.e. the choice of profession, and I argue that this choice may be undermined by the pressure to continuously acquire new skills while at the same time facing a diminishing range of professions that one can choose from. Given that the choice of profession is significant for not-work related spheres of life, its undermining can greatly affect individual autonomy in these other spheres too. I argue that such undermining of individual planning agency constitutes a distinctive form of harm that necessitates a proactive institutional response. (shrink)