In the old days, a common DOS warning ended with, "...press any key."
And yes, there were plenty of tech support calls that asked, "where is the ANY key?"
Every interaction with your public runs the risk that some people just won't get it. They won't understand the protocol at your jazz club, or figure out how they use that new thing you just built. They won't get your verbal shorthand or they'll be frustrated by your presumption that they're insiders.
One approach is to n00b-proof your offerings. To create products and services so simple and so well-explained that every single person will get it. Big warnings, extra paragraphs of copy, limited features... make it idiot-proof.
The problem with this approach is that you can never be simple enough. And of course, the bigger problem: Once you dumb it down so every single person gets it, you bake out the magic and the mystery and the elegance. Simple example: it's not obvious how to use an iPhone, not obvious what to do when you walk into a church for the first time, not clear what to do when you visit Facebook for the first time either. At the symphony, should there be big applause signs so that people don't clap at the wrong time?
Great design is intuitive. Great design eliminates confusion. But not for everyone, not all the time. The words and interactions you use often have a sophistication that will confuse some portion of your audience.
Why not consider making it easy for the confused to ask for help? And treat them with respect when they do. If you don't create a little confusion, it's unlikely you've built something remarkable.
And to go one step further: sometimes it's okay to lose the n00bs. Not in an arrogant way (except for some brands) but in a way that says, "this might just not be for you..."