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This study looks at the relationship between future orientation, challenging tasks and technological training-seeking behaviors in the technological environment that is Industry 4.0. Industry 4.0 is a source of various challenges (Cascio & Montealegre, 2016; Culot et al., 2020), especially in terms of the skills required in these companies. It therefore seems natural to ask ourselves about the factors leading to self-training behaviors, here in the form of technological training-seeking behaviors. We propose that the cognitive skill demand mediates the relationship between future orientation and technology training-seeking behaviors and that it also mediates the relationship between challenging tasks and technology training-seeking behaviors. A questionnaire was submitted to 290 employees of an Italian aerospace company. Structural equation analyses showed that cognitive skills requirements partially mediate the relationship between future orientation and technology training-seeking behaviors, and fully mediate the relationship between challenging tasks and technology training-seeking behaviors. This study adds further evidence to the literature on self-learning behaviour through technology-seeking behaviors. These results highlight the need for companies to engage their employees in future orientation and challenging tasks to trigger self-training behaviors.