I recently started carrying full time. My problem is I had never invested in the proper belt, holster and clothing to feel comfortable carry in all situations. I made it a priority this year to sort it out. I now have the proverbial box full of holsters and a couple that I like, I have some good gun belts, larger pants for IWB, and change from tucked in polo shirts to untucked Safari and fishing shirts.
I carry my G23 or G27 nearly everywhere appendix IWB or OWB. Not at the office because of corporate rules, but I also work from home a lot. I carry my P3AT in a pocket holster to church because the grandkids crawl all around us then. As they get older I'll carry the G27 even there.
It's great that you are looking for ways to increase your carry time. Make sure you have proper gear and equipment, then do the 48 challenge whether it is to carry more places or to carry loaded. I did it incrementally, too; as I got comfortable with one level of carry I then sought out where/how I could improve. The more you carry the more you realize other people do NOT scan you for you a gun on your hip.
A few professionals or other CCW might be able to tell you carry but so what? The vast majority of the public is not even thinking in those terms. We are use to seeing people lug around medical devices, various holstered beepers and phones, folding knives, etc.
I think the first month or two I felt the most awkward, but now I feel naked without it. I used to think how great that would be to be able to walk around armed and now when I pull on my pants I see that holster and Glock and it is cool to be prepared to defend my family at all times. It is easier just to wear it at all time then to try to figure odds and when and when not to carry. If you are switching your carry in and out then sooner or later you will leave it behind when you normally wouldn't or you will underestimate the risk.
Could anyone have predicted eating at Luby's diner with their elderly parents would be dangerous? Attending classes at a high school or Virginia Tech? Working at a church office? Often, then very places we are conditioned to think of as safe is exactly where evil, twisted perps act out because they know it will be totally unexpected.