One man's version of a prepared is often another man's version of paranoid, though I imagine that most of us can find a "reasonable" level of readiness.
I'm a police officers, and I always carry my gun while I'm off-duty (okay, swimming and such excluded). A number of my non-LE friends seem to think that this borders on delusional paranoia, and I've been asked how many times I actually had to use my "unnecessary" gun while off-duty. Of course, how many times have they needed to use their car's airbag? Their seatbelts? Their first aid kit for something other than a band-aid or Tylenol?
I don't mind the questions from my friends on the subject, and I certainly don't tell everyone I know that I'm carrying. It isn't a great deal of trouble for me to carry, and I'm used to having the gun with me for most of the week anyway (due to work). However, unlike some folks I've seen on this forum, I certainly don't carry a pistol along with 6 shotguns, a rifle, 4,000 rounds of ammo, and 2 years worth of food with me everytime I run to the grocery store for a gallon of milk!
I think a person's overall attitude towards life says a lot about how they feel on the topic of carrying a gun. I spend a lot of my free time in the wilderness, and I'm often the guy in the group who meticulously prepares for the unexpected before a backpacking trip. Some of my hiking friends hardly even bring what they need for the expected issues in a wilderness environment, let alone what they might need. Personally, I think a person's mindset towards overall preparedness says a lot about their decision on whether or not to carry a gun, and how they feel about other people carrying a gun.