I love freelancing. Given my choice, I’d do nothing else for the rest of my life. To date, I’ve not ever had a full-time job outside of writing and games, and I’ve effectively spoiled myself for any other kind of career.
I’ve had a few points at which I had long-term contracts (effectively salaries) with certain clients. I co-founded a noted RPG publisher (Pinnacle Entertainment) and ran served as its president for four years. I was also the director of Human Head Studios‘ tabletop games division for a couple years. But for the vast majority of the past 19 years since I got out of college, I’ve been a determined freelancer.
The thing about freelancing work is that its as steady as the deck of a storm-tossed ship. It rocks back and forth on the waves, and it’s up to the pilot of the ship to keep a steady hand on the wheel and trust to his skills and good fortune. Every now and then, even the most stalwart freelancer find his ship tossed upon the shoals, and he had to decide whether to ride it out or jump ship and start paddling for land.
The past few years, however, I’ve noticed a pattern in the timing of my freelance work. I start out the year in January with plenty of work and a good plan for taking care of it all in a manner that will keep my family fed and allow me the luxury of occasionally seeing my bed.
Come the spring, though, enough new projects drop in my lap that I need to give up the dream of dreaming through the night. I file for an extension on my tax return and hope that I can get back to them again before too long.
The trouble, of course, is that the best gigs never come first. If they did, I’d just take those and express my regrets to the others. Instead, I always seem to start out with some fun but clearly not spectacular projects and sign contracts for those. Then the better offers come in, and I have to decide between letting them slip away or sacrificing the little free time I have.
Free time always loses out.
I then work like crazy through the summer. I apologize to my all-too-understanding wife about having to bring my work along on our family vacation, but I thin the regrets over that by keeping work hours that would make a banker blanch. (Fun during daylight and work at night.)
Once we’re back home and school starts for the kids, I settle back into my office and realize that the deadlines I have are farther off than usual, the stress is less, and if I’m not careful I might actually run out of work. I take advantage of the breather for some home improvement projects, catching up on my sleep a bit, and—yes—finally doing those taxes.
Then I remember what comes in September. It’s the season of the pitch.
It’s about this time of year that companies start their plans for the next business cycle—either next year or farther out, depending on how big or ambitious they may be. They’re looking around for new ideas, and they’re open for suggestions. They want to discover the greatest new projects and bring them to life.
That’s where I come in. I reach into my bag of tricks and pull out a fistful of boomerangs. Then I scribble my ideas on them and let them fly. Some come back, and I throw them out there again. The ones that don’t are the ones I love best. Someone out there liked it enough to snatch it for herself.
That time is now. I have anywhere from a half-dozen to a dozen (or more) pitches, projects, and deals in various stages of development. Some of them are just for fun. Others might make me rich. Most fall in between. And I have no control over which ones will interest anyone. I just keep tossing them out there and hope I get enough responses before my arms get tired.
This season usually lasts until November. Then the week before Thanksgiving, right in the middle of the month, the companies make up their minds. They want to get things signed and sealed before the winter break, and we spend the next few weeks making that happen. Then we all go hibernate for the holidays.
Come January, it all starts over again. Right now, I can’t think about that though. I’ve got an idea for something else, and I have to find another boomerang on which to write it.

4 Comments, Comment or Ping
Jeff Preston
This is an excellent article. I’ve been doing freelancing on and off since 2002 and to be honest, I’ve paddled for land a few times now. This year is my most dedicated and driven year and I’m riding it out.
I’m glad there is a cycle to this thing…I’ve wondered repeatedly if it was just me.
Sep 21st, 2008
Dave Wilson
I think you nailed it…there are definitely times of year more likely to be conducive to successful pitching, and others where it’s best to keep the head down and nose to the keyboard…so to speak. September, for genre writers, means conventions like World Con and WFC where editors and publishers and authors often pound out deals for the coming year…
D
Sep 21st, 2008
Matt Forbeck
I’m sure the cycle differs for others, especially since I write for a number of different fields, but that’s how it’s worked out for me. Glad you both liked it!
Sep 21st, 2008
Dave Wilson
For short story authors, I know that folks like Marty Greenberg definitely plan their pitch season around the fall, when they can meet up at conventions, and I remember other deals hammered out at World Horror Conventions past, and at Dragoncon, which also falls around the end of the summer, along with WorldCon and WFC.
Sep 22nd, 2008
Reply to “The Season of the Pitch”