When a boat disappears over the horizon, does a distant observer detect the last moment in which the boat is visible, or the first moment in which the boat is not visible? This apparently ludicrous way of reasoning, heritage of long-lasting medieval debates on decision limit problems, paves the way to sophisticated contemporary debates concerning the methodological core of mathematics, physics and biology. These ancient, logically-framed conundrums throw us into the realm of bounded objects with fuzzy edges, where our mind fails to provide responses to plain questions such as: given a closed curve with a boundary (say, a cellular membrane) how do you recognize what is internal and what is external? We show how the choice of an alternative instead of another is not arbitrary, rather points towards entirely different ontological, philosophical and physical commitments. This paves the way to novel interpretations and operational approaches to challenging issues such as black hole singularities, continuous time in quantum dynamics, chaotic nonlinear paths, logarithmic plots, demarcation of living beings. In the sceptical reign where judgements seem to be suspended forever, the contemporary scientist stands for a sort of God equipped with infinite power who is utterly free to dictate the rules of the experimental settings.