How do you name your World? (Or nations, etc., for that matter...)

[Scipio]

As much easier (or maybe not) as it might be, I find that I just cannot allow myself to choose a random series of letters that sound nice as a name for a location. I guess I just have this insurmountable instinct that such names are meaningless; at best one can design a language around existing names to give them meaning after using such an arbitrary approach. While I have taken a linguistics course or two, I don't feel that I have the know how (and likely as much the inspiration) to create my own language from scratch, so I guess I tend to use culturally or geographically relevant names. This may not be a good thing however, as it means I end up borrowing a bunch of (albeit lesser-known) region/settlement names from Earth history/latin phrases (ex. Lusitania, Solis Orientalis), and for examples of the latter, Bogwatch, Glenwood, Montfort, the like... though all of those of course would only appear in a distinctly medieval European setting. I don't know... I guess in all honesty despite my self-satisfaction in having a "meaningful" name, I still end up with something generic-sounding for that. There's definitely a balance to be struck; with random letter combinations you run the risk of "Yeah, let's go to 'fantasy name that I predictably cannot pronounce'", whereas with a more pragmatic approach you may end up a bit too mundane. Of course, with regard to this trade-off, a lot has to do with the character of your world- historical or high fantasy?