Seems like you have a lot of people recommending .32's and .380's...maybe that's a good thing. Then again, maybe it isn't.
Have you really tried carrying a "midsize?" You know, something larger than a traditional backup, but smaller than a full size service pistol? Something in a larger bore (as in 9mm, 40, 45)?
Many people will tell you that a gun carried is better than a gun left at home - and there's no arguing that point. To carry a gun just because it's REALLY small, rather than to carry what you're capable of carrying, is the real shame.
I have many friends that are over 6'-3", 220 pounds, and most of them say that they have to just HAVE to have a tiny carry gun - that they can't conceal anything larger.
On the other hand, I have a friend who's close to 5'-6", and about 120 pounds soaking wet, and carries a Colt Combat Commander, in .45 ACP, DAILY! Is he a cop, or some kind of security guy? Nope - just the average, everyday guy that works from 8 to 5, in an office, and has never once had a problem with "printing" or anything of the like. He also doesn't have any complaints about the gun not being comfortable, or my favorite - the "it's just too heavy to carry all day" argument.
I've carried extensively over the last few years, and the one thing I've learned is that a person can carry the finest pistol made, but unless that person's wearing a GOOD holster, with a proper gun belt, they're just wasting their time - these well-intentioned people get frustrated and immediately start looking for what some people refer to as "mouseguns."
Me? Heck, I'm not a big guy (just shy of six feet), but I've carried everything, and have probably spent a couple of thousand dollars on leather. I've carried with ankle rigs (Glock 27), shoulder rigs (Beretta 92FS), and SigSauer P220's in SOB rigs. All have positives and negatives, but, after trial and error, I've found that my HK USP Compact .45 fits like a glove on me in a Galco Conceable, with an offside mage pouch and a Kramer gun belt. I can wear it all day, every day with a suit jacket on, or even with shorts and an untucked "polo" shirt during the summer while on a cookout (or, come to think of it, even a thicker t-shirt).
So in conclusion, do yourself a favor - go to a good gun shop, try on a holster from a reputable company, with a real gun belt, and discover how comfortable it can be, carrying a larger bore weapon.