(Fun is in quotation marks because all writing is fun to me. I can't think of a way to define writing without a deadline without being irritatingly repetitive for a title.)
I have trouble sitting down to write new stories if I'm not working under a deadline. A few of my favorites have been written off the top of my head, but I think my best work comes from the three Thunderdome battles I've done and some other competitions in which I've taken place. If I get randomly inspired, I will force myself to sit down and write at least a few hundred words on it, but I get bored quickly if the story doesn't click immediately.
Yet I'm extremely organized and I've never been a procrastinator. I keep all my stories, finished or unfinished, in a three-ring binder with separate pockets for each story I'm writing. I have notebooks filled with comments about where I'm going with stories.
But unless I have some sort of deadline, I can't knock out a good, solid story. It takes weeks to write even 3,000 words if I don't have someone waiting on a draft. How do other people fight that? I know there are just-for-exercise threads here, like the flash forums, with general deadlines for prompts but I'm more interested in figuring out how to write longer stories without fighting myself every step of the way.
You can give yourself a deadline. It will be easier to stick to if you give your friend a bunch of money. If you meet the deadline, your friend gives the money back. If you don't meet the deadline, you lose it.
A daily word count goal works for me. Take a break if you get bored. Perhaps listen to music while writing to alleviate boredom. Listen to instrumental music if vocals are too distracting.
If you don't outline your stories, give it a try. It may eliminate the whole story not "clicking" immediately thing once you start writing it.
Giving yourself a deadline doesn't work, I've tried. The only thing I can come up with for is to to look at other publications that are requesting submissions and have deadlines. It could, depending on the requirements push you to write something different. So even if the story ends up not being right for that publication you will still have a story.
You could also just keep battling people, become the ultimate warrior :-)
I usually enter Thunderdome or some competition. I usually grow more attached to the stories I write there.
Other than that, writing a story varies. It can take either a long time or a short while, followed by countless revisions. It all depends.
The best thing to do is to just type out a first draft, even if you have to force yourself. Come back to it later and add what you want. Make another draft.
This usually works for me.
I can't put together my thoughts clearly right now, I hope you can make sense of what I'm trying to say. It looks like a jumbled heap. I am sleep deprived and loaded on coffee, which has left me in a neutral state (Who cares right?)
Anyways, I hope that helps.
I usually force myself through drafts these days, whether it's for WAR or not.
WAR has been a really fantastic experience, but it's odd, writing a story and then moving on immediately afterward, letting the characters go and going to the next tale. I'm still used to spending weeks on one story, perfecting it over and over. That all said, I want to get submitting again, so I'm editing my "Blue Hawaii" from the previous round of WAR. We'll see how that goes.
I don't multi-task very well with writing.
What if you found an accountability partner? You could both work on some reasonable deadlines together, and have some check-ins along the way.
Just an idea.
I've quickly become a competition nut from being on this site. I've done three Thunderdome battles and I'm signed up for the Duo Competition and Bill and I are looking for a challenge in the Team Slayer thread.
Accountability partners sounds like a really good idea. Setting a deadline for myself can be tiring, because my brain knows there's no actual deadline, but I can usually do it if I have a good idea.
Outlining can be difficult for me, but if I have a plan, I'll stick to it. That's why I love Scrivener.
I think the hardest part for me is that I have so many things floating around. I always want to focus on one, and then I jump to another. With my competitive drive now, I keep wanting to do more and more battles and less revising and working. It's getting in the way of my actual writing, it seems.
I'm half-asleep so take everything I said with a grain of salt.