As we sit here on New Year's Eve, lots of people are probably thinking about their resolutions for the coming year. For a number of people hoping to compete in Superstar, those resolutions likely include becoming a professional game designer (which includes freelancing, as far as I'm concerned).
Superstar is, on one hand, one of the best ways to do that. If you manage to be in the less than 5 percent of contestants who get into the Top 32, you're going to have Paizo and plenty of Third Party Publishers aware of your name and a ready forum to show them your work. If you make the Top 4, you have a guaranteed contract with the biggest name in the business.
That said, it's also one of the worst ways to do that.
Superstar is a display of skill, but there's also a tremendous amount of luck involved in the competition. You have four rounds to put out work that's going to appeal to the largest number of people and your fate in many ways is in other people's hands. Instead of sitting back and hoping game design fame and glory simply comes to you in this annual event, you'd be far better off to go out and get it. (Also keep in mind that even success in the contest doesn't mean you have it made; I've never seen any products from one of my favorite Top 4 contestants of a few years ago. As Neil Spicer and others have noted, Superstar is in effect a job interview and you still have to do the work even if you land the job or you won't stick around for long.)
I remember when I made my first run at Superstar, I thought I had it made. I expected people to reach out and ask me to write for them, throwing projects at me that I'd clearly shown I was going to be able to nail. New flash: It didn't happen. I've been approached a couple times in my young game-design career to contribute to something, but the bulk of my work has involved me making it happen. I spent that first year after Superstar doing no professional game design, in large part because I didn't know what to do. I sat there and waited, but the gaming companies never came knocking.
It wasn't until I didn't get into Superstar the following year that I really got my design career started. I love participating in contests — the adrenaline and deadlines really get my creative juices flowing — so I started searching them out. I now have Paizo's Compatible Products From Other Publishers forum bookmarked and check it every single day. If there's a contest that piques my interest, I make sure to throw my hat in the ring. (The Compatible Products forum also has other listings from companies looking for freelancers, so even if contests aren't your thing, it's worth checking daily.)
But as with Superstar, contests are a somewhat passive way of developing your career. You're forced to sit and wait and hope someone will announce one at a time you're free to work on it, meaning you're not really taking care of your destiny.Participating twice in Raging Swan's random encounter open calls helped lead me to more work with the company. Even then, though, the company didn't simply throw a contract at me. After having some success via the contests, I asked if there was any more work I could do. Creighton mentioned a Dungeon Dressing book he was working on, which I then successfully pitched an idea for. It wasn't just handed to me and if I hadn't had an idea worth publishing, I wouldn't have gotten the job.
Being proactive is important. Get to know the 3PPs and what type of products they publish. Check out their websites and see if they accept unsolicited queries. If they do, find one that's well-suited for your idea (Raging Swan, for example, doesn't do monster books, so it wouldn't make sense to pitch a book of fearsome birds). Scott Gladstein at Little Red Goblin Games has a great page with more information, including what a publisher is likely looking for in your pitch, since even that can be daunting when you haven't done it before (the information is largely applicable to any 3PP you pitch, and well worth a read). Adventureaweek.com is another site where you have all the opportunity in the world to have your work published.
Similarly, Wayfinder is a great opportunity to show off your work. The fan-produced 'zine publishes articles and art set in Paizo's campaign world. It's a chance to show your knowledge of the setting and experience doing game design that's meant for a shared community. Check out previous issues, which can be downloaded for free, for a wide variety of articles you can submit. Creating monsters is your forte? No problem. Prefer more campaign world-building with less mechanics? Wayfinder's got that too.
So why wait? If you're serious about entering Superstar, there's no reason to just sit around and hope your big break comes to you.