Is there a contradiction at the root of philosophy? Here's what it might be: Philosophy began "in wonder", and asks us to question things -- the roots of our opinions, our beliefs, religions, the essence of objects, the values of life, etc. But it does NOT, emphatically, ask us to question the value of questioning. It ASSUMES (something philosophers should never do!!) that we should question. That seems to me a normative claim never questioned by you philosophers. And even if we WERE to question the value of questioning, we'd be engaging, it seems to me, in an act of performative self-contradiction. We'd still be assuming that we should question!

To be sure, there may be a performative contradiction in philosophy, insofar as to ask the value of the question is to ask a question. However, that bit of circularity does not mean that no philosopher has ever pursued the issue. On the contrary, many philosophers have asked the question of questioning. When Socrates claimed that ‘the unexamined life is not worth living’ this was not simply a statement, but part of an argument that pursued the issue of what type of life has value – indeed, what is value as such – and whether or not specifically philosophical questioning should be a part of it. In other words, it was not an assumption, but something argued for. Similarly with Kant in the famous essay ‘What is Enlightenment?’.

Both Nietzsche and Heidegger also tackle the issue, and do so in a way that seeks to uncover a mode of philosophising that is able to avoid traditional forms of questioning. The former in investigating the value of belief in truth, the latter in investigating whether the structure of questioning predetermined a part of the answer. These philosophers have not only noticed the problem you raise, but tried to do something about it: to pursue a philophical method that is able to bypass the model of knowledge that may be contained, implicitly, in previous accounts of philosophical questioning.

To question whether we should question is not to assume that we should question: at most it is to assume that questioning is permissible. Moreover, even to assume that we should question whether we should question seems coherent. We might thereby usefully discover that our assumption was incorrect.

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