#3. You Love Your Work
Writers have evolved to love their work, which is weird, because rampant breeding isn't something people associate with making jokes about Transformers online. But if you're making money online, it's because you kept at it for zero reward until that happened. Some people want to quit their jobs because they hate them and go write instead, which is the exact wrong attitude for a writer. You write because you love it. You write on top of your regular work, because words might be the true expression of your soul, but your unique spirit doesn't pay the rent.
I'm a unique free spirit, in that I can only afford things that are free.
Some people get hired straight into writing because they were smart enough to do the "find out what you really want to do and work at it utterly" thing in college, which is what college is for. The rest of us simply work two jobs, where the second is unpaid for a long time.
This means that you're pouring all your free time into writing, work that matters to you, instead of spending it in an endless parade of distractions to forget the next day's early start. You keep doing this until you're earning as much from the writing as you were from your old job, then you reward yourself by taking a 50 percent pay cut by going full time and betting "I can work twice as hard as I have been doing just to earn as much as I was." Anyone who doesn't truly enjoy the job is naturally selected against very quickly. Which means that if you make it, you're slightly more immune to online problems than most.
#2. No (Relative) Lack of Security
The biggest problem with freelancing has always been a lack of job security and the knowledge that you can be completely screwed by random employer decisions. So holy shit, real world, thanks for equalizing that problem, but you really shouldn't have. Employees who've been making themselves less dispensable than the company's oxygen supply for 20 years are suddenly finding themselves fired because of "the economy."
Screw those assholes, I'm taking my air generator with me!
I am not happy about this. It's punched several of my friends in the balls so hard they need to carve their underpants from ice every morning. Some friends worked hard for years to get a very nice contract and were then hauled into the office and told, "That really is a nice contract you have, but if you don't want to be fired the second it ends you'll sign this new one, which bends you over a table right now. Here's a pen."
They would have preferred a crotch shot. Daily.
I truly wish things were still going well for everyone else, because writing for a humor website is far easier when people aren't throwing themselves off tall buildings. But right now the idea of risking job security to follow your dreams has less downside than a Mobius strip.
Special Note: Get some medical insurance. Seriously. Don't screw around. Save money from your regular job, marry someone with a good plan, find someone who looks exactly like you, has a health plan, but doesn't get sick much, something. If insurance is too expensive, keep working and writing and working at selling writing until it isn't.
#1. Honest Feedback
If you gave a real writer a choice between honest, intelligent feedback or oral sex, they'd choose the feedback. Because they can get oral sex by themselves, and if it happened all the time they'd never get any writing done. If that sounds like misplaced priorities, well done on not being a writer. (Although I can confirm that "both" is still the best choice.)
You can't get honest feedback in the real world. Anyone you're showing your work to already knows you, and knows you're just starting out, and that you've put weeks of work into that piece. (If you haven't, don't be bothering your friends and family with that first-draft crap.) No matter how much you insist they should be honest, they know they have to deal with you for the foreseeable future. They ARE NOT going to tell you how bad it sucks, launching into a detailed blow-by-blow of exactly why, because that's something people only do to people they hate.
AND YOUR CHARACTERIZATION LACKS DEPTH!
I found one person prepared to give honest feedback when I sucked and praise when I didn't, so I married her. But since she's taken, now you you'll need the Internet. (Once you're working as a writer, this can change. My friends now know that honest feedback really helps me. And since I aim to write for devastatingly handsome and witty people, they're the perfect test audience. Hi guys!)
This is Commenters Part 2: The Trollening, because like any unnatural monster, they come back at the end when you thought you'd already dealt with them. And again, they're brilliant. People online have absolutely no interest in you as a human being. Many seem incapable of thinking that way, so they're honest. If 99 percent of all comments are hateful and stupid, it's only because 99 percent of people honestly are, and instead of being a nightmare, it means the 1 percent that remains is genuinely valuable.
Because when someone comes out of the Internet woodwork to say something positive, that's worth infinity million. They had no reason to claim they liked your stuff. They'd already read it and enjoyed it, and instead of darting to another site like a comedy one-night stand, they took several online seconds (which could have been spent on porn or talking to people they actually know) to tell you that. And when your work wins out over fake genitals and real people, that's praise.
In places like the Cracked writing forums you get even better feedback, genuine critiques from people with no interest in shouting "cocksucker." (I find that most people who shout "cocksucker" only wish they were friends with one.) You can get started right now, write now, and get intelligent feedback from other people for free. If you feel like being generous, you can become a better writer by returning the favor and reading their material, learning even more and telling them what you think.
Writing online means getting paid to learn about amazing things and then telling people what you think. It's the best job ever.
If you're thinking of writing online, you should also prepare with The 4 Worst Things About Writing For The Internet and The 8 Most Obnoxious Internet Commenters. Then sign up on the Cracked writer thread anyway, because you kick ass.
Luke McKinney got started when a he put a stupid poster he made for his workplace online, and a Cracked editor noticed it. His life has constantly improved ever since. He also tumbles and has a website.