Starting from the main findings pointed out both by theoretical and empirical approaches of bounded rationality, the paper examines the influence of organizational context on attainment discrepancy as a driving factor for adapting individual aspiration levels. The methodology used is a non-standard experimental technique combining traditional cognitive psychology setting and a role playing scheme. A number of individuals, with the same risk attitude composition, was involved into an experiment in which each one had to face a simulated socio-organizational scenario and to take a three-steps choice to improve the initial troubled economic condition of the simulated firm. The paper, playing upon a mixed quantitative (statistical indicators) and qualitative (cognitive mapping) analysis, draws conclusions on how individuals react respectively to light and deep scenario failure. In the first case, individuals are extremely influenced by the organizational climate, simulated by a fictitious board of directors that listens to individuals’ reasons after each choice and addresses next firm’s strategy (a risk taking and a risk averse leadership style). This issue somehow opposes the original March and Simon’s major argument that aspiration levels decrease in case of unsuccessful outcomes. In the second case (deep failure), individuals increase their aspiration levels due to their risk seeking behaviour, and this takes place apart from any socio-organizational pressure or style. The latter experimental result is explained in terms of some cognitive mechanisms that are referable primarily to a sunk costs effect (people are urged to adopt a losing strategy instead of considering as definitively vanished the costs of the earlier period), and secondly to a selective attention process that supports subjective evaluation by which individuals consider a strategy good enough playing on specific reasonable criteria in their cognitive representation.