I thought I'd just stop a moment and recommend the great "Philosophy Bites" podcast of David Edmonds and Nigel Warburton, in case any of you haven't heard it. They do a wonderful job, and have some of the best guests: there's a great, great piece with Princeton's amazing Philip Pettit they did recently, which I finally got around to hearing, which I particularly recommend (anything by Pettit is just fascinating).
And they are also extremely, extremely clear, though not much depth is actually sacrificed in the service of this. This is on the one hand not suprising, given the immense experience and knowledge of their guests, but also extremely suprising, given the nature of the medium and indeed the problems involved. But if there is anything I miss about philosophy sometimes, it is what they keep at work in the interviews: the imperative to clearly state something, to clearly formulate it, and clearly argue about it. It's that certain plain style aspect of philosophizing which I miss, that commitment to clear reasoning which makes Warburton quip that prose of Stanley Cavell, who is an extremely lucid writer in the scheme of things, is a bit "purple." Of course, it's more than a style (though a style too is usually more than just a style): it's an ethic, which makes me particularly fond of people like G.E. Moore--and Moore perhaps a little too fond of Wittgenstein.
I know people feel hemmed in by the sort of "common language" philosophy of the followers of the latter, and people outside philosophy often cite it disapprovingly as an example of the sort of weirdness of the imperative. But the truth is (and this is why those who diss the clarity-requirement I'm thinking of nevertheless usually love Wittgenstein) Wittgenstein doesn't really submit himself to the requirement of thinking clearly so much as identify clarification with a procedure for philosophizing. And while these two things overlap often, they aren't the same.
In short, Searle's "if you can't say it clearly, you don't understand it yourself" (which Warburton has at the top of his website) doesn't mean you need to work like Wittgenstein, even if you sometimes fall back on it and use it as a sort of guide to your thinking--i.e. using it even as a procedure isn't the same thing as identifying it with a procedure. Indeed, it means something quite broad: clear speaking and clear thinking usually go hand in hand, so if you're not speaking clearly about something, there's a good chance you don't understand it, and you need to think through it more. Hemingway spoke once somewhere of a bullshit detector, and it's basically that: a way of not confusing philosophy with poetry, even if you think the former is something of an art. But it is also a spur to thinking--that's the part people usually leave out--which encourages understanding: not unlike how Hegel thinks something is only known when you've seen both sides of it (which is all that much-maligned "synthesis" is, in the end: not grasping things one-sidedly).
And indeed, if it doesn't lead to bullshit, feeling this way about thinking through problems often leads you down certain more unsavory paths. One is the use of jargon as an excuse for technical language. Now, I am all for the use of technical language, and indeed the argument for saying things clearly could actually support this. Paul Ennis puts it best, probably, in these terms: sometimes you just need a word for something, and so the word chosen is one is weird. And that doesn't mean you don't speak clearly with it: all it means is that the word requires a special use. At the same time, and while it has been used against the cultivation of a clearer technical language (maybe I should speak intead of lingo, then), it's probably best to acknowledge a difference betwen jargon and technical language, because there is a use of specific terms that don't improve clarity (or even clearly demarcate the specifics of its use). An example of this would be theoretical discourse, of course, which is often just a way to allow thought to proceed precisely on the opposite principle of the one I'm talking about: the more you are led by unclarity, and into unclarity, the more you have thought something through. This trades on an insidious sophism--one which Searle precisely objected to, though perhaps a bit too harshly--which claims that what is thought is always going to be beyond my ability to refer to it, which isn't inherently wrong so much as wrong-headed: it smuggles in a notion that clear speaking involves direct reference to the object of thought, which as you can see from Searle's little formula is never mentioned, though it might be implied. One can't generalize from this that all clear thinking is referential, and therefore the only way to get beyond what we refer to is to use a weird term: indeed, it is often the case that when we use jargon, we precisely know what we're referring to, and just want to sound like an asshole.
The other way you go down if you don't make clarity a big part of your thought and speech, is something philosophers do all the time, actually, and isn't as insidious, though I find it unfortunate: it is gathering up what could be expressed clearly into a special "Problem," or "Argument" instead of giving it the form of exposition or even a technical term. The "mind-body problem" is one of these, though since that's more of a commonplace, I'm actually thinking more of something like what you encounter in ethics and aesthetics a lot, which usually describes a situation or a sort of crux which either amounts to an objection or something that needs to be thought around, or a position of some sort (in philosophy of mind, technical terms often do the same work: behaviorism means a position or proposition). It's a weird sort of work that is based on the same sorts of assumptions as formal logic, and while this isn't wrong, doing it in other areas than formal logic often leads to a lot of systematizing rather than sticking close to the subject matter. Sometimes, since the subject matter can be dizzying, and systematizing is precisely what you need (I don't mean to knock systems), but sometimes you'll be thinking through a problem and won't pursue a certain angle because you are too afraid it will ultimately end back in x position, in y problem, or, what's perhaps worse, that making an advancement in thinking amounts to merely getting past, resolving the contradictions in x position or y problem. And sticking close to the notion that saying things clearly often means thinking them through clearly can actually be quite liberating when this is the case. Most good philosophy I've read--especially in aesthetics, which is absolutely bogged down with -isms and formal problems of this sort--just returns to basics and tries to speak about what's going on clearly, just as most good academic work in general is, I find, remarkable for its ability to address something clearly but in a new way rather than obscurely.