I have heard this many times: “I only carry when I am going to a bad part of town.” Or, “I only carry when I am doing so-and-so and I might need my gun.” So, in other words, aside from these perceived high risk environments or tasks you don’t carry. This is a significant problem, but the unfortunate norm among the vast majority of concealed carriers.
Here is the problem people; there is no such thing as knowing when you may need your defensive weaponry in civilian life. If you knew when you needed your gun then morally, ethically, and LEGALLY you should just not be there to begin with. You don’t get to choose when a bad thing may happen: the criminal actor, or multiple actors, choose the where and when. The idea of carrying a handgun is to have a weapon that you can carry on your person at all times, not for expected trouble, but for the unexpected emergency.
If you know that you run a higher-than-usual risk of being violently assaulted then you should re-evaluate your life choices and avoid the particular environment that is giving you such reservation. Sure, if you own a business and carry the cash out of the store on Friday evenings, might it be possible that you are more likely to be held up at that moment? Yes. The underlying problem, however, is that by carrying only when doing this task you are not only convincing yourself that it is more likely to happen at this time than usual, but you are convincing yourself that it won’t happen at any other time. Thus, if it does happen at any other time you will not be armed and you will be thinking to yourself “I can’t believe this is happening!”
Carry your gun, carry it all of the time and everywhere legally permissible, or don’t carry at all.