Abstract: While most acknowledge the value of ICT and recognize its potential for new modalities of teaching and learning (including E-learning) that are made possible by them, the uncertainty about our collective and/or individual future often leads to feelings of discomfort. This paper presents a philosophical perspective on the unbridled optimism of some and the deep worries of others about the future of education (and by extension the future of humanity) in the era of E. Based on the principle of detrivialization, this paper argues that this uncertainty is an essential feature of a world in which learning is meaningful – without uncertainty, no learning is possible or even needed. Through learning and education, we try to take ownership of where we are headed, (and where not). In that sense, E-Ducation opens up more of an uncertain future.