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A lot of writers I admire say: "I didn't know how long the story would be." Me too, I'm the kind of writer who don't know where (and when) the story is going to end. So I'm confused—is it better to have a deadline?
By better I mean: more likely to finish something. And that something to be of good quality.
I don't see how a deadline could improve the quality of what you're writing; if you don't leave yourself enough time and make yourself rush, it could have the opposite effect. It can certainly motivate you to sit down and actually write, though, rather than thinking about what're going to write.
You've said you don't plot your stories in advance, so I'd imagine (especially if you're talking about a longer project) that it's not practical to set a deadline in your case. So obviously, in your case: no, a deadline isn't going to help you.
However, there are ways of disciplining yourself - and thus making yourself more productive - even though you don't know how long you'll need to finish your story. Just set yourself some kind of accomplishment that you will do each day. Use whatever measurement makes sense for you: word count, or some more subjective measure (only don't cheat!). I use page count, as I write my first drafts by hand. However you set your limit, don't make it too easy, or too hard: just a little more than is comfortable, so you're pushing yourself a little. It's amazing how easily you can cease to be 'blocked' if you know you aren't getting up from the desk without writing your daily quota.
If a deadline forces you to finish something, and make you finish something more often, it will lead to better quality of your writing. Perhaps not on the text you are currently writing, but it will improve your skill over time.
A teacher in a pottery class once divided the class in two. He told the first half that they would get a grade based on the quality of one vase. The other half would receive a grade based on the number of vases they produced.
Who do you think made the vases of highest quality in the end? The half that produced many.
The same principle applies to writing. If you write one book each year for ten years, the results at the end will probably better than if you focus on one book for ten years.
If a deadline forces you to produce more often (but perhaps of lesser quality in the beginning), it will lead to better quality over time.
I think it depends on the personality and approach of the writer. I tend to revise, edit and demand impossible perfection from myself. As a result, I am better with a deadline. There is a finite ending to the project and I know I have to accomplish everything within a designated period of time. I find it better to have a deadline so I can move forward with other projects rather than obsessing about one.
In my experience, deadlines are useful. I have a hard time with the last 10% and the deadline helps me get there. Deadlines help to motivate me to write instead of doing other things, such as spending all day meandering online. If I meet the goal, I'm succeeding (at least at something). If I don't have a goal ("meet the deadline"), it's harder to tell when I'm failing.
As a novelist, I think that deadlines force me to write more and more often, keeping me in touch with the flow of the story -- therefore better quality. (Of course, at the same time, I take breaks to step back from a piece and get a fresh perspective.)
All that being said, "having a deadline" and "knowing how long the story will be" are two different things. If I have a deadline and yet my story keeps getting longer, then obviously I will need to spend more time writing! It's a vote for working harder, sooner, rather than waiting until the last minute.
As a writer, I work better with a deadline. Let's call it a very flexible deadline. It sometimes help if I break up a project into little "deadlines" or checkpoints. I guess it's different for everybody, what works for me may not work for you. Personally it increases my productivity if I set achievable goals and reasonable limits on myself.
