I'm actually rather proud that I've never paid for a haircut, despite the fact that it goes against most logic. First off, I'm not saving that much money. Secondly, it pigeon-holes me into the following vicious cycle:
1. decide I need a haircut
2. cut my own hair
3. freak out over new haircut and try to hide it with updo's and various cranial accessories
4. let the hair grow out long enough until I can dismiss said haircut as "shagginess"
5. continue step 4 until step 1 comes about again
Have you ever held your bladder for a really long time just so you could have that moment of total relaxation when you finally let it go? Me neither, but that's the theory behind step 3. Cornered into desperation, creativity springs forth to save the day! I start off with the usual collection of hats, headbands, and pins. Then I start to experiment with styling my hair differently with the hopes that dramatic side parts cover the bad portions of my hair with good ones. Lastly, I warn people who see me on a daily basis in advance by drawing pictures of me with doo-rags and in tall updos associated with singing groups from the 60's. I like to think it lessens the initial shock while giving the situation some levity.
On a side note, I've actually had a few guy friends ask if I could cut their hair. Although I've cut my sister's hair multiple times (she cried the first time I cut her hair but has since hardened up to the experience), I refuse to cut a guy's hair. Guys can't afford the hair accessory path out that most girls have.
So why do I do it to myself, the most important person in my world? I've surprised myself each time despite the fact that I have a set routine for cutting hair. And assuming I think of other alternatives to my hairstyle other than emo-themed, I find the haircutting adventure to be a strange exploration into the various other personalities that I could be. I've often bought small accessories that don't fit in with the rest of my clothes, but usually chicken out such that I only wear them once as a novelty item. But your hair is always with you, and what's more, if it's bad, you can only make it shorter! The nature of hair's slow growth forces me to try out a new me, and to stick with it for awhile until I've reached the next awkward stage (which I usually refer to as my "David Cassidy stage"). And so I do it to, in my small and insignificant way, push myself out of my shell.