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I can give pointers. Your initial set of assumptions and reasoning is very close to that of Descartes' Meditations (I linked to that earlier), so I presumed you were familiar with his work. However, he continues his line of reasoning to "prove" that God exists, hence the joke. Since your line of thought agrees with his, you might want to read him.
You could do the whole "correct" path of Socrates, Plato, Aristotle, Roman Sceptics, etc etc, but although some are enlightening (especially the sceptics should appeal to the cynics), it can be dry at times. Personally, I totally dig Kierkegaard, for instance. He rocks. And Socrates is awesome, too. He's like the Big Daddy of Philosophy.
To put it differently: There's a big difference between having humility and learning about existing ideas before thinking you have everything figured out, and taking famous work on faith or not questioning it, or making assumptions either way about how "smart" it is.
Oh, but I never said you shouldn't question it, I agree that you should. I once wrote a paper on Descartes' Meditations II and III, pointing out the errors in his way of thinking (I don't know how good it was, I flunked out of uni before it got graded). That doesn't make me smarter than him, I've got access to knowledge of those who came after him. But to question it, you need to read it first.
Also, philosophers are never popular. Maybe they had groupies and fanclubs in ancient Greece or Rome, but not since then. They're famous because other people say they are, and those other people are generally more knowledgeable than I am. So it's at least an indication that their work is worth reading. It isn't always, there's a lot of crap around, but you never know until you read it.
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I think I understand you. I probably heard Descartes first few arguments somewhere in my past. If you remember (or look it up), I was trying to dissuade his first point: that we might be a fleeting dream of a butterfly with an entirely constructed reality. If it sounds like a similar argument, I would think it is so because it uses the same starting point, not the same logic. And btw, I think we can show that his logic falls apart to an uncreative mind at the first meditation, which is the simplest and most agreeable of them that I read on wikipedia. As long at the "dream of a butterfly" has any definition, there would be artifacts that it would predict. Every one of these can be tested against our senses and logic, and disproven in kind.
I recently purchased (for cheap) a translation of Plato's Republic. Alright, it was several months ago and I've only read about 5 chapters so far (it sits in my car). From this, I can see why Socrates was far ahead of his time, being willing to let argument change his mind and to actually care about the result of the arguments. I would think though, if philosophy builds on older philosophies like science does, that we should be a lot further along than they were. Thus I ask again what contributions the study of philosophy has given us, say, since the birth of science.
As for reading something before you question it, I don't think that is always necessary. It's necessary for the most fair and complete version, sure, but sometimes it falls apart long before then. I have still not read the whole christian bible, for example. I have read most of it, but it's really hard to get through vague chapters on how to kill cattle, or the biology of bats being birds, or to reread the history in the dullest forms of inconsistent genealogy. I think it's fair to still say it's a relatively useless volume though, based on the bits that I have read. More importantly, we don't have the mental capacity and time to read everybody's opinion. I skipped about 20 pages of theology discussion before I posted (reading the first few and the last few pages only). To question it, all it takes is a vague understanding, not a complete and exhaustive one.
An analogy, since I assume there are things you don't like about politics. Do we really need to listen to every single senator for hours at a time before we take a vote? Yes, they all question it (at least the half that is expected to), but the same logic they all use generally falls apart at some point.
Here's Dawkins talking about one of his books(Evolution: the greatest show on Earth).
http://fora.tv/2010/03/01/Meet_The_Author_Richard_Dawkins#fullprogram
Also, he claims, right at the beginning, that Evolution is a fact, not a theory. This is an interesting claim from such an advocate of scientific thinking. I haven't read the book, so I don't know if he uses any more specific arguments to support that claim, but it might be a good topic for further discussion.
Forgive Richard for saying it's a fact. It's a fact in the sense that anything in science is, with an absurd amount of support and no philosophical competitors. Yet every time we call it a theory, some nut job says "it's only a theory", which can grate on an evolutionary biologists nerves. I don't own the book yet, but from what I've read in the bookstore he does indeed back it up with a lot of evidence, as much as can fit in a book that size while still being readable by an eighth grader.
Just to add that things don't have to be 'true', for some absolute value of true, for them to be a fact only provable and not false. So facts are true as far as we can tell. This is a bit of a simplification but the best I can do with my limited wordsmith skills.
Huh? This reminds me of "I know you hate that your meme is a meme, so I created a meme of you hating your meme so you you can be hating you hate your a meme is a meme". Wordsmith skills indeed