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The essence of a tool is to enable humans to go above and beyond. The first inventions meant they were able to increase their strength, to see the invisible or to tame nature. The same can be said for computers and other tools related to thought. Their power should not come as a surprise since they were designed with that purpose in mind. But we should be aware that they allow us to think ahead while also influencing our way of thinking. Reasoning mainly consisted of speculating, confronting these hypotheses with reality and changing some of them as a result. But in a time of Big Data and algorithms, we refer to “virtual reality” and “augmented reality”! What is left of our ways of modeling and experimenting? Thinking is clearly no longer what it used to be! This essay takes us back to ancient Greece where logical and critical thinking were first formalized. It also reminds us of more recent developments in cognitive sciences that include creative thinking. With these benchmarks, Luc de Brabandere and Lina Benmehrez introduce the reader to information technology using a philosophical approach, connecting necessary clarifications and useful questioning.