How did you replace yourself as the person who holds all the context, when the context is the actual business?

Around $180k/mo, 16 people, 6 years. I've systematized delivery, sales, ops, all the stuff you can write down. The thing I can't seem to offload is that I'm the only one who holds the full context, the history with each big client, why we do things the odd way we do, what a given client actually means when they say a vague thing. It lives in my head and nothing breaks until I'm out for a week and then everything does, quietly.

I've tried documentation. The problem is the context isn't facts, it's judgment built from years of pattern, and a wiki page doesn't transfer "this client says fine when they mean angry, watch the second email."

For operators who got past this: did you accept that some context is non-transferable and just build redundancy around the risk, or did you find a way to actually move judgment, not just facts, into other people's heads? Did you pair someone with you for a long apprenticeship, did you let them make mistakes that the context would've prevented, and how long did it actually take before you could be out for two weeks without the silent breakage? Not after "document everything," I've done that, the documentable part isn't the problem.