In the Allegory of the Cave, Socrates suggests that, without philosophical education, we are all like the prisoners in the cave. To understand what being as prisoners in the cave is, we must understand why Socrates thinks that philosophy is important.
Socrates believes that what we know about the world is what the world wants us to know, therefore, our knowledge to the world is limited. Human is imperfect and the world that we live in is created by human, which means the world we live in is also imperfect. By being human is not about achieving the perfection, but to learn how to improve our imperfection. In order to achieve that goal, we must challenge ourselves to think and question about what we know, what the world wants us to know. It is then we can see the problems within our life and the world, and to find a solution to solve the imperfection.
In order to improve ourselves, we must challenge and free our mind to think and question outside of our comfort zone, the boundary line that the world set for us.
Socrates believes that life with philosophy is pessimistic. I think the word pessimistic is a bit exaggerated, but I do believe that life without philosophy would blind us from the truth about our own individual life, our community, our government, and our world. Also, without the truth, we would forever cage ourselves as a slave of this world.
You associate philosophical thinking here with the notions of questioning and improvement in general. This does perhaps make sense, although we also have to ask what is unique about philosophical thinking in itself.
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