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For the past several years, I've had my head shaved or very nearly shaved. Prior to that, I've gone through intermittent bouts of long/short/shaved/whatever with my hair. It's perfectly straight. There is lots of it, but it's very fine. I sometimes miss the easy ponytail, but not very often.
When it was really long (middle of my back long), I would get followed around in stores. People at concerts and on the street would ask me for or if I'd like to purchase drugs (never happened with the shaved head). One of the times I had long hair (in college) I decided to be both sloppy-looking and uber-responsible (running the campus pub, president of a social club, liaison to administration, etc.) just to confound people's stupid perceptions. It sometimes worked- like when I would have a scheduling meeting by telephone with an administrator and then deliver the flawless event... only to have the same administrator ask me if he/she could meet (me) the manager in person (because the hippie in front of him/her couldn't possibly be the manager).
My conservative mother has not approved of a haircut of mine since high school... and that's getting to be more years ago than I'd like to admit. Last few years of clean-shaven self-imposed baldness have been the cleanest and easiest of all haircuts. Just don't forget the sunscreen.
If you do grow out your hair, you'll go through several stages. The worst is what I called "***** length" - the point at which you have hair in your eyes but it won't yet tuck behind your ears. Horrible length - you'll be tempted to cut it often. Don't! Next comes the Dutch Boy look, where your hair tucks behind your ears but is too short to tie back. This was my least favorite, though my ex-wife liked it. Should have known. I suggest against the samurai look - the high ponytail with scraggly under quasi-mullet. It's tempting... but bad news. Do not succumb to the thought that cutting the hair on the back of your neck beneath the high ponytail is a good idea. All one length is what you want.
But, you still need to get haircuts at every step of the process. Get the ends trimmed and everything evened-out. You'll have to get some good conditioner as well- or you'll end up looking like a missing/lost member of Twisted Sister. One guy who used to cut my long hair in Atlanta had formerly toured with Kansas in the same capacity... so while he was accustomed to teasing and volumizing hair, he knew a few things about conditioning. Washing everyday may or may not be a good idea depending on your hair and the products/water you use to clean/condition it. Shampoo warm, apply conditioner then rinse w/ cooler water.
In any case, it's fun to do the social experiment. I really never cared what was going on with my hair, but it was amazing how many other people around me did, and how they thought my hairstyle defined me.
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