How do you know when your work is good enough to publish?
It depends on your goals. Is your goal to be a published author, making a living at writing? Then you only need your writing to be good enough to get published, and to convince people who read it to pay you to write more.
That's my goal. My main goal. It would be nice to be a world-renowned author with lots of awards and attention, but I think that happens more by luck than even by hard work. Someone with the talent and skill and marketing sense and who can put in a colossal amount of hard work... still might not become world-famous. But as long as you keep writing, you've got a chance.
That's why my main goal is to get paid for writing. Because if I can get paid for writing, I can give up my day job, and then I can spend all the time I would have been programming, writing. And then I'll be writing 8-10 hours a day, instead of the 1-2 I have time for right now.
But to get paid for writing, you have to be able to write stuff people will pay you for. And you have to know if it's good enough before you send it off to be read, because if it's not good enough, your work will get rejected and ignored.
So when I ask, "How do you know when it's good?" what I'm really asking is, "How do you know when it's good enough that someone will buy it?" This isn't a hard and fast line; consider short story A, which would be bought for print by 5% of the potential buyers, versus story B, which would be bought for print by 30% of the potential buyers. Is it good enough? That depends on whether you can find someone in the set of buyers who will buy your work.
One indicator that it's good enough, or almost good enough, is that an editor or agent shows interest in it -- or if someone actually buys it. Then you know that professionals in the field consider it [almost] good enough. With a little more work, a little more practice, maybe it finally will be good enough.
The only thing you can accurately say about a work that hasn't sold is that it hasn't sold yet. Maybe it won't ever sell; maybe you just haven't found the right buyer yet. When it does sell, then you've got proof that you can write something sellable; but that doesn't mean you can do it again.
But if you're a writer, you'll sure as hell keep trying. I know I will. I will write until the day I die.
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