After 300 agent rejections, in spite of your revisions? Based on your critique group's feedback? Or is it "just a feeling"? When is it time to hang it up and start trying to sell the next one? How do you know?

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My feeling is that revising again after 300 (?) rejections is a waste of time. Start another novel.
It's hard to let go of one novel and start another one, but it's the best thing, especially after a significant number of agent rejections and revisions. I wrote six novels before I placed one. Two of those are certainly unpublishable. One was borderline. Two more were agented, so I assume they were in the ballpark. Your unsold novel won't disappear. It will still be there if you want to go back and revise it in a couple of years. And in writing another novel you may learn how to effectively revise the first one.
OK, I wasn't clear enough. I don't have 300 rejections. My question was how do you know when to hang it up... what your personal litmus tests are.
I'm of the opinion that the writer should always be working on the next novel/story. For me, it is time to start a writing a new novel when I've finished the old one. My gut tells me whether it is good or not (I am, after all, an avid reader...) and when I'm done writing one, I send it out. When I'm done with the next, I send that out as well.

I guess, ultimately, if the market were to give me a resounding no - the 300 rejection scenario - I'd take that hint. Doesn't mean anything at all about the quality of the work. I've never had a critique group. I have a novel that I thin is pretty good, but no one wants to take it. So I pull it out of circulation for a while and send out the next one. When that breaks through, I might get asked if I have anything else lying around. It happens.
Selling inventory is the best revenge for all those rejections. :)
Ah, yes. 300 rejections didn't sound quite right. But neither is my case an example of when to give up. I'd usually stop marketing after 5 rejections. Like Naomi, I was completely wrapped up in my protagonist's story and could not stop writing the next installment. After 3 novels had gone through a brief marketing experience, I wrote some short stories with the same protagonist. The third one sold. The sixth won a Shamus award. By then the 4th novel (THE HELL SCREEN) was finished, found an agent, and found a publisher along with one of the others. By now all my early novels are in print.
You don't need to give up as soon as I did, but you should keep writing in the meantime.
Quitting after five rejections - you must be even more sensitive than I am! I quit marketing two novels after about 18 rejections each. People told me that was much too soon to give up, but my ego was too fragile at the time. I'm very happy I went with a print-on-demand publisher for Mood Swing I feel much more like a bona fide author even if it doesn't have the cachet of a traditional publisher, and it gives me the confidence to try the traditional route as well.

And yes, I realize rejection is part of the scene at all levels - at Malice, I dined with a famous, award-winning writer who said her new series idea had been rejected by numerous publishers before it found a taker. I'm determined to grow a tougher skin.
Before I sold, I kept proposals going out on my previous manuscript but got on with new material right away. I never stop writing unless it's a short break for sanity reasons. I realized that if I sold, I'd need inventory for a multiple book deal. For me, I learn from each book so I don't like rehashing old material. I prefer to move in. And rehashing can stir up self-doubt. Keep writing, Christa!!

After I sold, I devised a concept for my next 3-book series and drafted the writing sample, synopsis brief and cover letter overview. If I hadn't sold this series, I planned to write it anyway since I believed in the project, but some authors might set it aside to start something else and keep generating new proposals. After you sell and have some track record, a publisher might buy a book off a proposal so no use spending time writing the whole thing when you can sell on a partial.

But having said that, be prepared that rejections and waiting are still a way of life even after you publish.
Depends if you are just trying to sell that one novel/storyline or if you are attempting to become a novelist. Not mutually exclusive, yet not the same thing, either. If you are attempting to become a working career novelist, I would put the novel aside after a healthy number of agent/small press rejections. I think that the market, not a critique group, is the best judge. It could be that your novel is before its time; if that's the case, as others have suggested, you can bring it out later.

In my case, I was fanatically devoted to my story and my protagonist. It didn't make any logical sense. But I just kept at it for 15 years while I made money writing nonfiction, etc.. Now I'm focused on being a career novelist, which makes my decisions sometimes more business-based. But the deal for the first will always be the sweetest, because my intentions were much more pure.

You'll know when to give it up when you feel that you are totally in a dead end. If it's relatively easy for you to walk away, maybe you weren't that invested in the story, anyway.
My first novel didn't sell so I wrote two more that didn't sell, but believed so strongly that the first novel was a good story that I rewrote it several times. That's the novel that became Beneath A Panamanian Moon. I won't dig up the other two mss, but that one I couldn't let go.

I think that's how you tell. When even after rejections and you've written other books, you're still convinced that this is good, just not good enough. Then you rewrite.

Be as honest as you can be and listen to your gut. That's what I think.
What Naomi said. There are more stories to write for me. I've told several people who are very serious writers that it is time to move to the next project. Presumably a long career will see you write a few dozen novels (Look at Ed McBain for one). Given that perspective, there is no reason to think about how long to flog the first book because the career writer will always be moving on to the next project.
I think I have the opposite problem. I gave up on the novel in stories after ten agents said rewrite it as a novel or said no outright.. I guess this is why reason I write short stories--less at risk, less investment. After reading this, maybe I will send it out again. But I'm not going to rewrite it as a continuous narrative. I think what charm it has lies in the little arcs, not in the bigger one.

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