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Are you a perfectionist? Perfectionism can be maddening. Imagine rereading and rewriting a piece until you can no longer even understand how it will be perceived by other people.
Yet this type of revision is essential to creating a creditable piece of writing, whether it’s fiction, expository writing, or an essay for class. Perfectionism is annoying, but it can pay dividends.
Many famous writers have spoken to the importance of revision. John Updike and Joyce Carol Oates come to mind. Below is an example of Updike’s incessant editing from Rabbit at Rest:

On the other hand, I suspect some writers did not go too crazy with revision. Hemingway’s Old Man and the Sea, for example, contains several glaring typos which would have never made it past a truly thorough revision process. Perhaps he was working from such inspiration, and from such a position of experience, that he did not feel the need to revise to this extent.
When editing starts to produce diminishing returns, however, it is time to call your piece of writing finished. You only get one life, so you have to put up or shut up. Send it to the editor, hand your essay in to the teacher, play the game. You’ll know when it’s ready because you are no longer making improvements in your rereads and revisions. You’ve caught all the mistakes and phrased things as stylishly as possible. And importantly, you still feel pleased with what you’ve done.
No matter how dogged and disciplined you might be, if you are stuck in a process of never-ending revision, it is time to consider that you are either finished, or you will never be finished because your effort is lacking. Some writing can be turned around from bad to excellent. Some writing needs to simply be discarded.
If a piece of writing cannot be salvaged, it could be that the premise is somehow unsound, and therefore all the revising cannot save it. It isn’t a matter of style in this case; the issue could be the concept itself.
Don’t let your ego get in the way of mercilessly evaluating your own writing.
Just because you wrote it, it doesn’t mean that you hit the mark. Don’t be “married” to the first version that you wrote merely because you happened to write it. Sometimes it may be better to try a new effort rather than struggling with a work that just doesn’t connect. You may be a great writer, but even great writers miss the mark. In that case, dust yourself off and try again.