Hmmm, there is this one book I read, which is split into three parts. The first part is a fairly standard hero narrative, where the heroine wants to be a $super_elite_person_thingy, but she can't because she wasn't born to the right family / doesn't have the right training, etc etc, but by natural talent and hard work she eventually proves herself and becomes a $super_elite_person_thingy.

In the second part she meets someone who goes "okay you're a hero, you got in. But that hasn't changed anything for *the rest of us* who were in your position. You won a place in the system, congrats, but that hasn't changed the way the system works." and the rest of the book goes ahead and deals with that.

It's not quite the same as what you describe, but it's one of the few I can think of that's addressed the point of the protagonist winning doesn't automatically equate to progress, or them being *right*.



I have a vague idea that I may have seen fantasy series where the protagonist gets things wrong -- but usually it's to show that the protagonist was pretty spoiled near the beginning and grows up, or it's a inaccurate / biased narrator thing, and not *quite* along the lines of what you're referring to.