After reading through Plato's Allegory of the Cave and taking some time to think about it, I can't help but agree with what Plato and Socrates are trying to teach us. The allegory is meant to show that those who never question, never learn anything outside the norm and look deeper at what they think they know, believe that what they see is right and real even though it isn't. In the allegory when someone finally goes out of the cave and sees the sun, whch is meant to represent true knowledge, they realize there is so much more to everything they had thought before. They then feel an obligation to go back into the cave and explain to the others, but are almost always rejected and ridiculed as those still trapped in the cave write these new ideas off as impossible and ludacris. This is showing how people become so set in their ways and comftorable with what they've known for so long, that they are unwilling to branch out and gain further understanding by looking at different ideas and questioning their own. If they are unable to break out of this, like the prisoners in the cave, they become just that - prisoners in the caves of their minds.
I believe philosophy to be liberating because like we see Socrates explain in The Apology, to truely be wise you must be able to realize and and accept that you don't know everything about everything, or anything about anything really. Everything is subject to change with further examination and there is always more to be taken out of every idea and situation. Being able to recognize and accept this would be extremely liberating because it would mean giving up all control of what you think you know about everything in your life.
Although he's implying that those without philosophy are like prisoners trapped in a cave, I don't think Socrates is neccesarilly being pessimistic. He's certainly showing how much better life is outside of that, but he explains that those in the cave are content and comfortable because they don't know any better. They think they're right and don't understand what they're missing so even though they are not truely enlightened, many of them believe themselves to be. Only after breaking through that and seeing the truth do they recognize that they had been stuck in that sort of mental prison.
This is an interesting post. The passage you mention from the Apology here is really important too. It tells us that knowing the limits of our knowledge is the most important thing we can know.
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