Up until two days ago, I had very long hair. When it was wet, it hung almost to my waist. Since it's wavy/curly (varies by the day), it was a fair bit shorter when it was dry: just below the bottom of my bra strap. I really liked having long hair, but it eventually started to wear on me.
First and foremost, long hair is a royal pain to maintain. Especially if it's curly. Curly hair is prone to dryness and breaking, which means speshul snoflayke hair products that cost a fortune and a maintenance routine that is, frankly, ridiculous. Neither of these things guarantee that your hair will cooperate, either. Sure, the $25 a bottle hair conditioner plus silicone-free products improved my ratio of good hair days to bad, but I still had enough bad days to where my hair spent most of its time in a bun because it looked like crap wavy and I couldn't be bothered to straighten it (long hair takes forever to flat iron, and doing so repeatedly can damage curls and make them more likely to look cruddy the next time around). Air-drying is another necessity, which can really suck when it's cold out and you don't have the two to three hours it takes for your hair to dry all the way.
Second, as I hinted above, keeping one's hair long is expensive. If you keep your hair shoulder-length or shorter, your hair gets cut faster than it gets damaged by less-than-ideal product. If your hair is long, though, the $25 a bottle conditioner is necessary. You also have to spend more money on haircuts since you're supposed to get it trimmed more frequently, and a lot of salons charge extra if your hair is that long. Apparently cutting long hair is also a pain.
The third and final reason why I decided to cut my hair, is that chlorine and other pool chemicals really accelerate the drying and splitting process. I didn't fancy adding another set of steps to my already out-of-control haircare regime in order to keep the pool from frying my hair, so I decided to skip merrily down the path of last resistance, buy a hair dryer, and get the length taken off.
My hair is currently right at shoulder length. All said and done, I lost somewhere between eight and ten inches in length. I'm still getting used to it, but mostly, I like it. It's nice not having to use two handfuls of omgexpensive conditioner every time I wash it, and I can wear it straight guilt-free, which means no more leaving the house with wet hair during the winter! I also don't have to worry about my ends not matching my roots (I don't dye my hair, but it does change colors seasonally) or obsess over whether a given activity is going to damage it beyond all repair. It's a pretty nice feeling. I'll post a picture sometime tomorrow, once I have enough daylight to get a decent shot with the webcam/cell phone.