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The phenomenon of the “brain drain” in Italy is becoming an expression of market changes. In this climate that involves the whole professional world, to which Italy seems to adapt with difficulty, “expert” workers increase their professional empowerment by emigrating. This generation of “drained brains,” in fact, lives in uncertainty, linked to the decision to move abroad, in which the individual is aware of the outcomes of the decision but is unaware of the probabilities linked to the different outcomes (Lopes 1983). Indeed, different aspects come into play in the decision-making process, but since the decisions made by the “brains planning on leaving” can be considered risky decisions, we will analyze the psychological literature of reference on risk perception and propensity, on individual differences in traits, and on the influence of the affective/emotional dimension. After analyzing the literature on decision making, the study aims to explore how question and answer (Q&A) websites dedicated to the Italian brain drain become decision-making spaces, based on listening to other people’s experiences. The methodology is quantitative and qualitative. For the quantitative part, a sentiment analysis was carried out (Pang & Lee 2008); for the qualitative part, a diatextual analysis was performed (Manuti & Mininni 2017).