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My family, and wife's family all know. My closest friends know too. Why? Because of our conversations, I've convinced several of them to get their own CHL. They know me, and that I'm not weird or crazy, and through that the idea of self-protection, and carrying a gun is less odd or scary.

With casual acquaintances and clients, I generally don't bring it up. If shooting, guns, or self-defense comes up, I can usually lead into the conversation by getting them to admit they have a CHL first. If they do, then I figure the door is open. If they don't, then I'll steer clear. For example, a client might be discussing having their car broken into. I'll ask what they would have done if they had happened upon the thief in the middle of the crime, and they might respond with either call the police, OR whip out their gun. If they say they would pull out their gun, I plainly ask if they have a carry license. It's all good from there.