That is the question. My answer: I will one day, I have no doubt. I have not yet.
Naturally, I have a story about this. I submitted a novella to a publisher who'd put out a call for a specific flavor of story. My novella did not make the cut, but I liked the characters and the story. So, I briefly considered self-publishing it. Why briefly? Because the rejection came in on a Thursday and by Monday morning, I had email from an editor desperate to fill a hole in an anthology she was editing. She asked if I had a story tucked in a drawer that I could dust off for her.
Here's my self-publishing point. I was dreadfully uncomfortable to have not come into the anthology the traditional way - via a submission that could be rejected. The story had already been rejected in one incarnation. Sure, I'd reworked it. But the point is, not every idea can be a hit out of the park, right? What if this story was just a stupid idea that deserved to be rejected? From this brief experience (which, again turned out just fine because the editor sent edits back saying it was a perfectly fine story. I got to refine it further based on her suggestions and fix what needed fixing) I discovered how much I rely on someone else telling me whether my story passes muster or not.
Why yes, I am a neurotic, self-doubting mess. What makes you ask?
It appears that self-publishing will require two things of me when I get around to it: 1. I'll have to suck up my emo and get a story out there so the market can tell me whether a story is stupid, mediocre or brilliant. 2. I'll want to pay a professional editor to tell me when something I've written isn't fit to wrap dead fish (and subsequently how to fix it - if it's worth saving at all).
I suspect that *how* one goes about publishing isn't as important as having plenty of content to publish on a regular basis. While I'm working on the content part, I follow several blogs that beat the self-publishing drum - places that will teach you everything you could ever want to know regarding the hows and whyfors of the process. http://www.kristinekathrynrusch.com/ (specifically her Thursday blog posts on the business) and http://jakonrath.blogspot.com/ which kind of covers everything under the sun, but if you hunt down his self-publishing posts, they're goldmines of information.
There you have my secret strategy: Keep writing and keep learning about self-publishing.
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