I think the case re: lesson / learning is less clear, because in a “learning” there’s no teacher, you’ve all learned something, whereas lesson implies teacher and taught.
A lot of the time, a metaphorical lesson has no teacher, too. "Learning" is imported to the tech scene from India, where "a verb-ing" seems to be able to be the noun form of one instance of the verb (in certain contexts).
I find that limiting the number of things that drive you up a wall is good.
"I have something to ask of you" is not a novel term for request. And ask is softer than request, giving the other party more opening to decline. I don't hate it.