According to the Authors Guild Bulletin, Plato rewrote the first sentence of The Republic 50 times.
Here's the first sentence of The Republic, as published:
I went down to the Piraeus yesterday with Glaucon, son of Ariston, to pray to the goddess; and, at the same time, I wanted to observe how they would put on the festival, since they were now holding it for the first time.
Now don't tell me that doesn't draw you in. I couldn't help wondering what that opening looked like 50 rewrites ago.
I know, I know. This is probably a ridiculous example of what I'm getting at. Someone is certainly going to explain the meaning of this passage and provide all the reasons why this is actually a perfect opening for the book. It telegraphs meaning, and it hints at things to come. But it's a long way from there, stylistically at least, to "Call me Ishmael." Let's just admit that right now.
Anyway, this got me thinking about openings, not just first sentences, but opening pages. If you're like me, you rewrite the opening of your story or your book at least 50 times, until it is absolutely the best dang thing you've ever written.
And then you toss it.
Because odds are, if it needed that much work, it was wrong wrong wrong from the start, and you need to go somewhere else with it entirely. Meaning Brand New approach. Not just different words.
But how and when do you make this determination? I mentioned Richard Peabody's approach before--he routinely cuts the first 3-5 pages of work he's critiquing for others, and he's usually right. Because one part of knowing how to begin the story is knowing that before you find what it's about, you're likely to put too much down on the page. Especially if you're less experienced, but even sometimes if you're not...You're going to be tempted to take the reader for a walk down the street, past the cracks in the sidewalk, the sprinklers that come on even when it's raining, the ugly Airstream in the neighbor's driveway, the misshapen hedge of Japanese holly, all before you get to the house where the important conflict will occur between the mother whose letters have revealed a secret life and her daughter who based her whole life on what she thought she knew about her mother. Most of that early stuff turns out to be wallpaper. Wallpaper that should be stripped to find what's underneath. Otherwise, someone better get pushed into the holly hedge and escape in the Airstream before too long. It can be very tempting to look at those early pages with a sort of love bred from familiarity, to keep going over them and over them, in case it's really just the words that are not quite right.
But no, it's not the words, it's the whole thing. If it takes that much going over, it's time to start over, in my opinion.
I like the way the novelist Benjamin Percy describes the revision process in a recent issue of Poets & Writers:
"So much of revision...is about coming to terms with that word: gone. Letting things go."
He goes on to describe what happens in terms that remind me of early medicine in the days of leeches: "...the professional writer mercilessly lops off limbs, rips out innards like party streamers, drains away gallons of blood, and then calls down the lightning to bring the body back to life."
And as everyone knows, when the body is brought to life again, it's irrevocably changed.

Comments
"As everyone knows, when the body is brought to life again, it's irrevocably changed."
If you're not going to use it, can I? :)
Alice Munro's stories always seem to open at the end of the street, but because she's Alice Munro she can do whatever she wants.