While trying to preserve the autonomy of their playful activity consisting in a game of ‘questioning and answering’, the Gymnosophists defy Alexander the Great and, more importantly, go against their own chances of survival (since giving a wrong answer to the king’s question amounts to losing their life). Thankfully, we do not need to face such dilemmas when philosophising with children. Nevertheless, the Gymnosophists’ example helps construct a notion of philosophy for/with children as an autonomous playful activity that albeit (implicitly) purposive it is, however, without (explicit) purpose (something akin to Kant’s aesthetic judgement). Alluding to an Aristotelian sense of ‘telos’ in its connection with Platonic ‘paideia’ I understand philosophy for/with children as an activity that we carry out for its own sake. This does not mean that we are to abolish elements such as antagonism, competition, excellence, etc.―there is no question: the competitive element is there. But what does it mean? We could fix its meaning according to a purpose (we compete to excel or persuade and win) or we might entertain the idea of keeping its meaning rather vague or undetermined, implicit.