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The point of departure for our considerations is a well-established opinion that in the age of rapid global changes of the contemporary world, education does not meet people’s expectations and despite the attempts to reform it, remains in crisis. We attempt to specify the foundations of the problematicality of contemporary education and to put forward a methodological approach serving to enhance the understanding thereof. The authors distinguish between the problem with education and the primary problem of education. It is demonstrated that what is responsible for the problems with education is to a large extent “problem reasoning,” which dominates the relation between contemporary man and his environment and is blind to the distinction between problem and question. Blurring this distinction and expelling important issues from the realm of education translates into focusing attention on standardized teaching and neglecting vital issues pertaining to upbringing, which results in the forming of “one-dimensional man,” who fails to deal with uncertainty of the contemporary world, while “forgetting” the non-problem-related, which means—positively speaking—question-related, modes of implementing his open existence.