Did you know that the term "freelancer" was coined by Sir Walter Scott (just a Wikipedia link - for obvious reasons, Scott has neglected to get himself a website) in Ivanhoe (another book I haven't read yet) as a term for a medieval mercenary. That is, I am free to carry my lance (and leave) whenever I like, as opposed to the sworn knights who would be in trouble if they tried a stunt like that.
A couple of people have asked me to talk about how I got to be a freelancer in the first place, but I've been resisting actually writing the post. I'm kind of uncomfortable crowing too much about my RPG freelancing, in part because it seems rude and in part because I'm afraid that if I seem to enjoy it too much, someone will take it away from me. Of course, I am also enormously proud of myself, my freelancing is a big part of my life and it's silly to try to talk around it, and the lure of rockstardom is often too strong to resist (once, at party, after I managed to work in that I was a White Wolf freelancer a cute girl actually said - only partly in jest - "wow, you just got a whole lot cooler"), so it usually ends up slipping out eventually anyway. In any case, I promised this post, and what the Burning Zeppelin promises, it delivers.
The story of how I got my first freelance contract is short, sweet, and almost entirely thanks to the Abigail.
About a year ago, I started reading the livejournal of one Matthew McFarland, a White Wolf writer and developer whose work I was very fond of. In a sense, it was the beginning of my use of the web to market myself, though at the time I didn't see it as such. I was just interested in reading the thoughts and comments of someone whose writing I liked, not to mention the length Actual Play posts about his Mage: the Awakening, Werewolf: the Forsaken, and Promethean: the Created games. Anyway, at some point last June or May, Matt posted about working on a project for White Wolf and believing that it was a good opportunity to get some new blood into the line. The request was for writers who, if I recall correctly, could write cool and evocative stuff, could meet a deadline, knew the setting and system of Mage well, could meet a deadline, knew how to take instruction from an editor, and could meet a goddamn deadline.
With the Abigail's urging (and by urging, I mean "checking on me three times to make sure I'd actually done it) I sent Matt an email saying that I believed that I could do all of the above. He asked for a writing sample, which I spent about a week agonizing over. You can read the results here: Mason's Angel. By the end, I was reasonably fond of it, but more importantly, Matt liked it. I had a contract in my hand within a week.
Of course, that was only the beginning. I had my first contract, but then I had to keep it. Ultimately, the key to successful freelancing proved very simple, and Matt summed it up pretty well in his livejournal post:
Cool and Evocative isn't something I can't give you, but you can give it to yourself. Write lots and you'll write better. Of course, you don't need me to tell you that.
On the other hand, Knowing the Setting and System only really applies to RPG writing, though I suppose something similar could be said about any other kind of freelancing. You're going to find it a lot easier to write about something you know well. When it comes to RPGs, however, this requirement gets a lot more specific. One of the things I wasn't surprised to read in my writer's guide or hear at the GenCon "How To Write for White Wolf" seminar is that nobody wants a setting guy who can't write system. If you think you can write awesome, evocative, chilling setting material but would rather someone else did the statting, well... guys like that are apparently a dime a dozen. People who can back their ideas up with cold, hard mechanics are a lot more valuable.
Some writers apparently have trouble with Taking Instruction, which kind of baffles me. If you give shit to your boss about how he tells you to do your job, you get fired, right? I should know, it happened to me once. Writing shouldn't be any different. I've always taken the attitude that when I'm freelancing, the developer is the boss and I'll do whatever he says. If my precious writing-baby was so dear that I couldn't compromise it, I should have kept it at home, or better yet, in my head. Taking money for my writing means letting it out into the world, fitting it into other people's visions and ideas, and making it comprehensible to customers. I think this makes writing better, but even if you disagree, you have to acknowledge that the editor is the boss and you are the lowly employee. Deal.
Finally, one of my strengths is Meeting a Goddamn Deadline. This is very hard for me to acknowledge, because in the rest of my life I'm the reigning king of late, rushed, and incomplete (and I stand to inherit totally fucked up when I come of age). Despite all that, I have never handed in an RPG contract late, and I never will. I'm pretty convinced that I could be half the writer I am and still get work in the RPG industry based on that fact.
There you have it, the sum of my wisdom when it comes to RPG freelancing: be in the right place at the right time (with the right girlfriend - no, you can't have mine), and once there, write your best, know your stuff, do as your told, and have it in on time, and you to can have cute girls (or boys, or both, whatever floats your boat) telling you you're cool.
And also, money for writing.