This part of the game -- the illicit, post-story part -- is better than anything that might have preceded it in the name of story. In a world empty of fate, gone slack without a narrative, my character, alone and aimless, has a life for the first time.
The weird thing is, most open world games allow you to wander around without doing any quests at all, or just enough to level up so you don't get killed. Why does he have to exhaust every scrap of content before he feels "free at last"? This has something to do with the world outside games -- I don't want to call it "real" -- where we do stuff to "get stuff done", but like waiting for a river to flow past, we never get to the end of it.
What the author is seeking is not the freedom to wander, but a higher-order quest, where the reward for getting stuff done is not the character's satisfaction that Skyrim is free of monsters, but the player's satisfaction, impossible in his own world, that he has come to the end of getting stuff done.
Now I see two angles. One is practical, that we're always being told to do stuff we'd rather not do. The solution is to work toward a post-scarcity utopia, like the pre-scarcity utopia in Jean Liedloff's The Continuum Concept, where the right to say no is so powerful that it's forbidden to even ask someone to do something.
The other angle is philosophical, and I don't see any solution. In games, the meaning of life is a set of clearly defined tasks, and if you're not doing those things, you're in a space that is clearly defined as having no meaning. In our own world, we can never be sure.