I currently have two stories that I think are submission-worthy, one of which just brought in its third rejection. I'm looking forward to having more stories out in the mail, so as to spread out my attention span and not have so much invested in each one. It's interesting to learn about the process from the inside, though, even with only two making the rounds now.
Story #1 is a weird little short thing (1,300 words) that went out for the first time in November, and I'm still waiting for a reply on its second submission. That's due sometime within the next week. The first rejection sounded like a slight positive, and that's a hard subtlety to explain, but I will take it.
Story #2 is a more normal length, at 4,600 words, and I didn't start sending it out until January, but it's gotten a variety of remarks within its first three trips out, including one that sounded like "meh," one that sounded positive and indicated interest in more of my work, and one that was completely neutral and businesslike.
My goal is to be realistically persistent in submitting my writing to markets that seem right for each story. I'm not sure exactly how many rejections will tell me that a story is not ready for publication anywhere, and needs to be either revised again or trunked, but I suppose that keeping at it will make a clue begin to emerge along the way. I don't want to waste time--mine or anyone else's--but I don't want to give up on a story too easily, either. My new plan to get more written will, I hope, begin to teach me more about the short story form and how to engage the reader more thoroughly. I feel like practice is making some changes in the way my mind works, at least. I think I'm catching on to some new things.
What are you trying to learn to do?