Given the unity of language-and-world and of what-we-say-and-do at the level of the language-game, it is easy to see how Wittgenstein's "It [Philosophy] leaves everything as it is' gave occasion to the reproach of conservatism. The chapter discusses this criticism and argues that given Wittgenstein's profoundly anti-foundational stance this is not what his position embraces. That "Doubt comes after belief" refers to the embeddedness of our acting in a matrix of certainty; therefore, the child is initiated in the form of life. I then focus my attention on the reception of Cavell's position in philosophy of education debates. Questioning some of the turns this debate has taken (by stressing for example departure from, practicing freedom differently), it is argued that some authors model every relationship between a grown-up and a child along the lines of the way the grown-up is always in a process of attaining a further next self. Ignoring the distinction between the latter process and initiation results in confusions which do neither justice to Cavell or Wittgenstein; moreover, they obfuscate relevant distinctions of the nature of education and child-rearing.