sheveksmath
What slows you down is when new ideas are introduced, like when you go from multi-paradigm languages like Python & Typescript to a more purely functional language like Haskell, or learning about ownership in Rust where there may be no equivalent in other languages. But ideally you only need to learn them once, and in a way that allows you to identify and apply them in a variety of contexts.
But regardless of whether you have a fancy doc site or just a single README, I think it's important to just get information down that's actually important and written as clearly as possible, and then sorting by how commonly that information may be needed. It's also helpful to put yourself in the shoes of a junior developer or someone completely new to the project: does x make sense outside of this context? Oftentimes when we refer to some project-specific concept, we don't realize that there are implicit mental dependencies that someone must have before they can understand what we're talking about. The best documentation makes the fewest assumptions they can get away with about the reader's previous knowledge.