The goal of this article is to investigate the role of imagining as a foundation for doubting in Wittgenstein's "On certainty". In this paper I argue that imagining alternatives to existing situation within a language game is what underlies doubting.
In my paper I distinguish between imagining within a game and imagining a new game. The former one is referring to doubting in Wittgensteinian sense since it provides alternatives within the existing game struggling to be the true one.
In contrast imagining a new game cannot be identified with doubting since it requires reimagining the hinge foundation of the game or the life form.