My original forays into Zen, I'm not proud to admit, were almost entirely intellectual and literary. Meaning I did a lot of reading about it, and got good enough with the terminology and the theory to fake a smart discussion about it, but I didn't study it on a personal level.
Eventually I edged into doing just that — read: I began practicing zazen — and the ballgame was renewed in toto. All the stuff I'd read before wasn't theory anymore; it was practice. That said, I still think the majority of what's written about Buddhism and Zen, and the majority of the way we talk about it, is way too insular for its own good.
That I see less a failing of Zen per se than a function of how any subject with a vertical interest profile (narrow but deep) is hard to get people to know about in a sincere way. Most of how we get to know about, say, something like Dungeons & Dragons is not because we read the gamebooks; it's because a friend of ours brings us into the weekly tabletop sessions, and we're surrounded by other people who get into it. We get infected.
Ideally, the best way to get into Zen is by way of other people. But because there are so few people who practice it, and so few legitimate institutions for same, many people automatically think of that as being too high a barrier to bother with. If Zen hews too closely to the original temples-and-bells-and-robes incarnation, it runs the risk of feeling alienating to people who aren't interested in "getting religion". If it's too freeform and label-less, then it runs the risk of devolving into yet another spiritual trinket that's as easily discarded as it is picked up. So they end up gravitating towards these pop-mainstream dilutions of Zen and Buddhism that encourage complacency instead of skepticism. The barrier to entry there is so much lower, and there's more there that the audience is familiar with, but the actual practice is weak tea.
Brad Warner talks about this problem a lot. From what I can tell, a fair amount of it is rooted in how talk of things Buddhist or Zen tends to follow several rigid, preprogrammed paths that revolve around buzzwords. The most common is "mindfulness" (yecch); another is "joy" (sigh). Most of them seem like Buddhist- or Zen-tinged versions of mainstream, Prosperity Gospel-inflected thinking from Think And Grow Rich to The Secret. (That stuff is as toxic to winners as it is to losers.) Good, unpretentious teachers who promise you nothing are hard to find, because who the hell wants to be in that business when it's far easier, and more profitable, to sell people happiness or success?
Brad's answer to all of this has been to write about this stuff in the most unpretentious and direct way he can. He's not in this to make himself "look all groovy and 'Zen'", as he put it, but to find ways to link all this stuff up to the things that fill our lives anyway. Most people still think of Zen as something ancient and weird, so anything that can make it relevant and immediate without also cheapening it is going to be worthwhile. One of the myths Brad helped bust for me was the idea that the Japanese today have an affinity for Zen. Ten-plus years spent in that country showed him how the Japanese regard Zen as being some old, weird thing in much the same way folks in the West do.
I'm still going back and forth about the best way to discuss this stuff with other people. Save for this blog, I don't really talk about it with others — I figure the point of this practice is just to make the world a better place for myself and everyone that happens to be near me (by dint of me being that much less of a neurotic twerp), and not to proselytize the practice itself.
I'm also not big on the idea of recommending that people read, say, D.T. Suzuki or any of the other old-school popularizers of Zen in the West. A lot of this material just hasn't dated well, or seems left-of-center to getting people to understand that the practice itself, not talking about it, is what matters most. Right now, I'm in the position of just hoping the results speak for themselves.