Yes, it becomes second nature at some point. If you're not doing anything illegal, don't overthink it. It also helps to understand that most people are completely oblivious to what others are wearing on their belts. I've open carried and am convinced few people even notice if it's behind your hip. I good belt built for supporting the weight of a handgun in a good holster is the key, and makes a HUGE difference in comfort and confidence. I've regularly carried a 1911 with two spare mags for over three decades. This winter I've switched it up to a Beretta M9 and one spare. Both are large but I forget I have them on, and go about my business. In summer, I either carry the 1911 or a compact 9mm depending on clothing.