The goal of this paper is to highlight the role of assessment today, analyzing it within educational contexts based on self-directed learning. In addition, the role of new technologies will be emphasized, highlighting how the high level of technologization we are experiencing allows for a twofold analysis of society: on the one hand, we note how interactions are mediated mostly by a screen; therefore, emotions undergo a necessary transformation, ranging from a mitigation of empathy to a fetishism of it. This element becomes fundamental to understanding the non-bearing of judgment. On the other hand, on the other hand, it is possible to see how the passive use of these technologies lead to autonomous learning, in some cases better than traditional learning. All this leads to the need to reflect on ways to initiate literacy and acculturation paths to assessment (Scriven, 2000; 2008).