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Eventually you actually do have to question questioning things.

What a lot of people will do is if you don't come up with the answer that they want you to, they'll just keep on trying to get you to question it, hoping to spend the roulette wheel enough times that eventually it lands on the answer they want and then once you've arrived at the answer that they want they'll throw a padlock on that roulette wheel and it's no longer acceptable to question anything.

So that's why you question things until you've come up with answers that you are satisfied with, but once you have some answers at your satisfied with you don't really need to go back and relitigate everything constantly. In some ways, that's why spinster exists -- the powers that be asked you to keep an open mind and question everything right up until they reached the answer they wanted, and now in a lot of places around the world they want to make it illegal to question the new doctrine that they impose.

In modern Western philosophy the skeptics questioned even the idea that we exist. Eventually, skepticism was defeated to a degree by the famous phrase "I think, therefore I am". The idea being that simply being a thing that can think for itself proves that that thing must exist. Exufficiently skeptical person could continue to be skeptical, but this answer was considered good enough that then those same modern philosophers could move on to different questions.

One of the criticisms of Western postmodern philosophy is the fact that postmodernism effectively acts to smash down all Grand narratives without ever intending to rebuild those narratives. Regardless of what answers you come up with you just keep on questioning and deconstructing. This is one reason why for philosophers they moved on from postmodernism to other ideas such as metamodernism which tries to keep a degree of the skepticism of postmodernism while returning to at least accepting the concept of a grand narrative from modernism, or entirely different philosophies which actually try to solve The world's questions rather than just ask more questions.
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