I take a little issue with your assertion that "I live in a free country" is to assert nothing. Your argument is less a philosophical one and more a semantic one. Most people would agree that the statement "I live in a free country" means that one lives in a country in which a certain set of standards are met, even if some specifics change. Among those standards are 1) that one can express one's thoughts freely without threat of persecution; and 2) that rule of law is supreme so that the government can't arbitrarily violate citizens' lawful rights. This is freedom by definition. If you're arguing that definitions don't matter unless we understand the context in which the word is used, then really what you're doing is basic linguistics. Of course, Wittgenstein argued that all philosophy is a critique of language, so maybe I'm the one making the semantic argument. But nonetheless my main point is that we can't argue about any subject unless we understand what words mean in this or that context.
That particular passage seems to have hit some nerves. I like the comment though and am happy to clarify. The things that you assert are freedoms by definition are indeed freedoms, but they aren’t the only possible freedoms. Soviet diplomats used to be fond of pointing out that, in many places in America, it was dangerous to walk the streets at night. The Soviet Union, on the other hand, had almost no street crime. In their view, being able to walk the streets of any city at any hour was a relevant freedom, and being able to say bad things about the government wasn’t. This was no idle construct either. I remember a news story from the 1970’s about a small but interesting group of elderly Americans who had made the decision to emigrate to Poland. Why? Precisely for the reason the Soviets had emphasized – the freedom from crime. You and I might care about free speech but, frankly, many people don’t. There are all sorts of ways a society can call itself free, and that is really my point. When a person says “I live in a free country” they haven’t told you anything until you find out what kind of freedom they care about. I think that’s still philosophy and not linguistics, though frankly I’m not sure you can draw a sharp line between the two. I spent about a year and a half beating my head against liar sentences, and learned a great deal about both language and philosophy in the process. I was not, by the way, invoking Wittgenstein. My knowledge of Wittgenstein is pretty rudimentary. Again, I enjoyed and appreciate the comment. Thank you!
Yes I suppose I operate from a position of assuming that by "freedom" we aren't talking about the complete set of possible freedoms, but the more narrow view of freedom that is associated with modern liberalism. But you're right that there is a blurred line between linguistics and philosophy. The two, although separate, aren't really separable. They're inextricably convolved. Anyway, I did enjoy the writing, but it's always more fun to critique than to compliment, just to get the conversation moving :)You and I might care about free speech but, frankly, many people don’t. There are all sorts of ways a society can call itself free, and that is really my point. When a person says “I live in a free country” they haven’t told you anything until you find out what kind of freedom they care about.