At the end of the preliminary, critical section of the Encyclopedia Logic, Hegel notes that what has just transpired -- to wit, a thoroughgoing criticism of the history of philosophy of logic and ontology in 100 pages -- could have been achieved through skepticism about all presuppositions. In other words, instead of the detailed work Hegel has done, he could have begun by saying something like "hey, kids, you know what? Everything you thought you knew about logic is wrong. Now let's start over."
Why not just make that quick move? There's a pretty strong history of throwing out presuppositions and re-starting ontology. It's a move that allegedly permits foundational certainty, that means our knowing will be complete, real, 100% knowing, not only organic but also pesticide free and shade-grown, etc. Presuppositions, you see, are the genetically modified organisms of ontology. You're never entirely certain what they're made of or that they're going to work out the way you planned, and by the time you realize it, they've already irreparably mutated and cross-bred with everything you're growing. The skeptical move in ontology is the insistence that we start with virgin soil, virgin seeds, the pure sun, and water from untainted mountain sources. Start over again, you see, after razing what had been there before.
Hegel says doing so would be "sad," but more to the point, redundant, because the approach he's going to take to systematically construct ontology will do that work along the way. There's a constant negation of half-thought half-logic, abstraction and incompletion in Hegel's system. It picks up every single philosophical idea and perspective, both historically and systematically, and subjects each one of them to this negation. I can try to explain this basic move in Hegel's thought with the example of "immediate knowing."
Hegel says that one position on knowing is that we immediately know: this knowing cannot be justified in terms of what else we know, or in terms of our evidence, or anything. It is exactly like faith. This form of knowing isn't unfamiliar. Take this: "I know that this dog is speaking to me with the voice of god." Now, a claim like that cannot be given evidence. It cannot be justified in terms of other things the speaker knows (you can't say, "... and I know this because..."). This idea can only be asserted as true, and this assertion can only rest on itself. Immediate knowing, as a position about knowing, says that knowing cannot be tested or proven.
The skeptical move here would be to say that we shouldn't believe anything merely asserted, because it presupposes that the speaker isn't crazy, that a dog could possibly speak, that there is a god who could and would speak through a dog, etc. etc., and thus debunk the claim to know.
Hegel's claim is this: not only can't there be evidence either for or against a claim to immediate knowledge, but the claim to immediate knowledge can't be immediate. If "I know this dog speaks to me with the voice of god" can only be asserted as immediate knowing without any justification, that assertion, to have the content that it has, to have the meaning that it has, cannot be asserted immediately. "I know that this dog is speaking to me with the voice of god" requires that the proposition itself, to have any meaning at all, says something that even the speaker must be able to evaluate the truth or falsity of -- or else it is not a claim to know, at all. In other words, it can't be immediate, because it is in relation to something else that would be able to tell us whether the sentence is well-formed, says something predicable, etc.
What I think this means, about Hegel's view of philosophical positions about knowing, is that every positive stance about knowing that commits the error of being one-sided is not merely false (which they are, because they are one-sided), but that none of them can be meant as they are meant. Every philosophical position-taking is hypocritical.
Every philosophical position-taking is hypocritical.
"Except Hegel's?" you're asking. Or your dog is asking.
Yes, except Hegel's... insofar as Hegel doesn't take a position. The truth is the whole, if played out consistently, means that he can't take a position (or, technically, that if and when he does, he then undermines it).
So, skepticism isn't skeptical enough, because it's only skeptical that positions are true, or that any position could be true. Hegel's skepticism is that the position isn't what it is, and the position-taker can't take the position.
Far frickin out.