THIS
I had absolutely never thought of this, but Lindybeige here is about to make a lot of sense to you.
Allow to me to paraphrase him and explain the gist of this video.
When we imagine dice rolling, too many of us imagine it as representing the character’s “effort” (this being a certain combination of inherent skill, trained skill, and pure luck). But in reality, it makes much more sense for the roll to represent part of the world.
Say, for example, that a character has a climb skill of 65%. If he wants to climb a wall, and rolls a percentage die and it comes up 63, the player will sigh in exasperation, and say something like “I just BARELY make it over the wall.”
How we should think of it, however, is that the character can climb 65 percent of walls. The roll represents whether or not this happens to be one of these walls.
This also allows for more rules to make sense. For example, by vanilla Dungeons and Dragons rules, if the Rogue fails at a slight of hand check to pick a lock, then they aren’t allowed to repeat a roll. Which doesn’t make any sense if all that happened is that the rogue tried to pick the lock and then failed. If, instead, this is one of the locks that this rogue doesn’t know how to pick, then it makes a lot more sense that they can’t try again. It’s just too complex of a mechanism.