Working as a writer is all about filling the pipeline.
It's very rare that I take on more than one project at a time. I'm not saying that its impossible to work on more than one thing at once, but it definitely helps to do a good job if there's only one thing occupying your attention at one time. That means that the best way to do things is to continually look for more work, and then block out time to spend on those projects. Freelancers frequently face one of two problems. The first problem is that you don't have enough work to fill all the holes in your schedule. The second problem is that you have enough projects but you underestimate the amount of time it will take on another project, and that throws your whole schedule into chaos.
I've faced both problems in the past. In one case real life kept throwing me a bunch of curve balls, and on top of that I had projects do. It wasn't my finest hour as a writer, but what can you do? You can't make yourself less burned out, nor can you create time where there is none. All you can really do is hope that the guy you're writing for is a patient and forgiving person.
The other problem is the one facing me right now. I had cleared my schedule entirely, and I had intended to keep it that way for a good long time. I had intended to get a nice normal job and simply enjoy gaming again. No deadline stress, no getting burned out on the subject matter, just enjoying the hobby again. That all changed when I lost my last job due to some stupid political BS that had nothing to do with me. So I've finally decided to play to my strengths and go full time with my writing, and most people who know me think that's a good thing.
The problem I'm currently running into is keeping busy. I'm currently working on a 60,000 word project, and I'm about 2/3 of the way done with it. I'm hoping to be done with it by the end of the month, but I'm taking it on faith that there will be more projects lined up after that. Right now there's nothing definite. Most of the major publishers are in a holding pattern due to the release of 4th edition D&D. Many are unsure whether they'll pay the $5K to get an early start on compatible material, some aren't sure whether they'll make the switch at all, and I think that a lot of them are just waiting to see what the others will do. The end result of this is that there aren't very many freelance gigs to go around at the moment. This is not the best time to be trying to fill the pipeline. I'd get something going with WotC, but they aren't showing the 4th edition rules to anyone who doesn't already have them, which means that it will be June before I can start on anything new for them.
So one thing I have going at the moment is that the company that is publishing the True20 product I'm currently working on thinks they can keep me going for a while. They think I do good work, they enjoy working with me, and the nice thing about True20 is that it won't be going through an edition change anytime soon. So that's one thing I can sort of count on. I'm not going to lie and say that they pay as well as WotC, but they're good people and I enjoy working for them.
Another thing I might have going is a novel, but this is a big maybe. Back in November of last year I started a novel because it was National Novel Writing Month. I didn't make it to the 50,000 word goal, but I did get over 20,000 words. More importantly, I think its a good story and I also think its publishable. I recently contacted a novel publisher about publishing with them, and the vibe I got from their email was that they were interested, so send the manuscript for what I have. That has now been sent, so now I just wait to see whether they like it or not and want to see the rest. This is my first real attempt to get a novel published, so I'm hoping for the best but preparing for the worst. The one thing I have going for me that should keep me out of the slush pile is that I have done a lot of writing for WotC.
So right now I'm faced with the daunting task of re-breaking into the writing profession. I suppose this is a pretty minor complaint when you stop to consider that I didn't get paid for any of my work for the first two years I was doing game design. Breaking in to the industry isn't the easiest thing in the world to do, but as my friend Eric Cagle said, once you're in, you're in.... unless you really do something to f*** it up.