This paper deals with Wittgenstein’s rule-following paradox, focussing on the infinite rule-regress as featured in Kripke’s Wittgenstein on Rules and Private Language. I argue that one of the most salient and popular proposed solutions (championed by John McDowell), which argues that rule-following is grounded in “custom,” “practice” or “form of life, remains unsatisfactory because part of this proposal is the rejection of further “theory” (commonly attributed to Wittgenstein) which seemingly makes it impossible to substantiate the claim of how customs, practices (...) or forms of life ground rule-following. I argue that this conundrum can be solved by introducing Wilhelm Dilthey’s overlooked notion of objective spirit as the objectivated sediment of historical human communality. This proposal allows us to substantiate Wittgenstein’s hints at the connection between rule-following and customs, practices, and forms of life without introducing “problematic theories.” Combining Wittgenstein’s views with Dilthey’s notion of objective spirit results in a solution that is neither skeptical nor straight, but therapeutic. (shrink)