Short story submission

I've been thinking I'll submit the original version of The Vigil for a short story contest. I'm enroute, as it were, to converting it over to a novel, but it can't hurt to try. Thus far I've submitted two inquiry letters to literary agents for The Summer of Pomba Gira, and received rejection emails. I've considered converting that story over to novella length and submitting it for a novella contest. It's easier to write something for a particular venue than to cut parts out of it once it's been written, I"m finding. I'd submitted a 600 word short for an NPR contest but didn't win it. It was a comedy piece to be read over the air (presuming one wins!) but writing humor isn't really my thing.

It will all happen eventually, it's just a matter of trying, refining the art, becoming accustomed to the medium from the reader's perspective, I think. I'm used to writing what interests me and I understand what interests me. I think that's problematic, because it assumes that the reader also knows what I'm talking about, which isn't always the case.