Actually I find that I almost never understand philosophy.

IMO most philosophers don't understand the stuff they write themself... Which philosophy do you have in mind? I'm from Germany so many of my friends are fans of Heidegger, Sartre, Hegel or some other continental or postmodern philosopher. You know, I don't claim to understand what these folks are talking about. But it's probably because most continental philosophers are kinda crazy, not because I'm stupid. In contrast to this I don't understand QM or AI, simply because it's too complicated, not because it's gibberish. Well, it could be that e.g. Heidegger is simply too intelligent and complicated for guys like me, but this hypothesis appears to be rather improbable after you actually read some lines of this dude. But if we are talking about, say, Dennett, then the situation is different...