Pardon my cyncicism, but you may suffer a little from being too interested in communicating with the hoi polloi, the civilians, the canaille. Your blog is readable and interesting. You may assume that obviously all philosophers would like to be broadly be understood, but I invite you to check your experiences to see if they hypothesis that they don't has some viability. Searle is likely a brilliant exception, and I hope you find whoever the brilliant exceptions at Columbia and attach yourself to them.
It IS important to keep in mind that your life goals are NOT the same as the department's or your advisor's.
Having checked my experiences carefully, I'm pretty sure he's right: most philosophers care very little about being understood by anyone who doesn't have a PhD, and far too many philosophers (read: Continental Philosophers) don't really care if they're not understood by even that relatively small subset of the population. This is, I think, a Very Bad Thing.
I'm pretty sure I've mentioned in the past that one of the reasons that I very much admire John Searle and his work is that he really makes an effort--or at least is naturally very good at--writing with a very high degree of clarity; a relatively educated person (i.e. someone with a high school diploma and a curious mind) can pick up many of Searle's books and, though he might not understand all of it, will at least understand enough to be able to converse intelligently about its contents. By contrast, I read a lot of philosophers as an undergraduate (Saul Kripke springs to mind) who, while brilliant, are almost indecipherable to those without savant-like abilities in analytic philosophy (again, Kripke springs to mind). While I like to take snide pot-shots at Continental Philosophers (Kant, Hegel) and Postmodernists (Derrida, Foucault), this is even more of a serious criticism of them--in some cases (e.g. Derrida), it's not even clear if the author knows what the hell he's talking about.
I think a lot of this stems from / mirrors the trend in philosophical education--if you do graduate work at a top tier (top 20 or so) school, you're expected to want (and maybe even get) a job at a major research university, where you'll have a 2/2 teaching load and spend the majority of your time cranking out journal articles and books. By contrast, teaching seems to be something that is thought of as best left to the "second rate" philosophers; people who go to lower ranked institutions are expected to get hired by small liberal arts colleges, teach 4/5 or even 5/5, and spend very little time doing research. It's sort of a meritocracy-meets-division-of-labor approach. The end result of all of this, I think, is that the people with the most "academic talent," (i.e. those coming out of NYU/Princeton/Rutgers/etc.) will, by the end of their PhD, have developed the habit of writing only for other philosophers; they'll be told explicitly and implicitly that the "academic dream job" is one with little to no teaching responsibility and lots of time for research. I don't buy this model, but I do think there's room for nuance.
Philosophy is a very broad discipline, covering everything from "Does God exist?" to "How do I know other people have minds?" to "Is it ok to clone humans?" and much more. While the answers to all of these questions do impact Average Joe somehow, obviously some are going to have more relevance to every day life (questions of normative ethics are particularly relevant), and some will have less relevance (nit-picky ontology questions about the nature of color, maybe). Given this, it seems reasonable to assert that philosophers ought to be able to write at two levels: a very precise, technical, academic level that is designed to deal with very small technical issues (is consciousness an emergent or supervenient property?), and a broader, less technical, more accessible level to communicate important philosophical ideas to the general public. My major objection to the system as it stands is that there is not enough overlap here--if an author is skillful, many questions can be dealt with simultaneously on both levels. Searle is great at doing this--most of his books and articles could easily be written for the layperson, but also give careful and skillful consideration to important philosophical questions. This balance should be the rule rather than the exception, I think.
Similarly, I think universities (even, or perhaps especially, the top tier) should focus on a balance between research and teaching, ensuring that graduates from prestigious philosophy programs are capable of teaching quality philosophy classes, a task that is significantly harder than those without teaching experience tend to think it is. I can honestly say that many--if not most--of my theoretical developments have come as the result of discussing the issues while teaching (either formally or informally), and I think this is a fact that is under recognized: by being a better teacher, you will become a better researcher, as your ideas will (must) be made clearer as you explain them and are challenged by those who disagree.
Philosophy, broadly, is concerned with the same task that science is concerned with: figuring out what's true about reality. Whereas science deals with specifics and facts, philosophy deals with generalities and concepts; both are essential if we really want to get at an accurate description of the world around us, and it's important for both to be understood by the majority of people if we want to have an educated population.