There are two schools of thought about where to start submitting short stories. The scary one says you should start at the top and work your way down until someone accepts your short story. The other one says you should start at the bottom (or near it) and use those credits to help you get into more professional markets.
I agree with the first – but scary – method.
The simple truth of the matter is, getting published in ‘for the love’ or token payment mags and ezines does not help you get published in professional markets. Places like Fantasy Magazine, Magazine of Science Fiction and Fantasy, and Strange Horizons probably don’t care that your story made it into Bob’s Mag O’ Fantasy.
Submitting your short story to the top magazines first is a ‘hey, you never know’ kind of proposition. I expect to be rejected from them, and therefore, am not devastated when the rejection comes. One problem with this method is that the time spent querying and submitting is probably longer than if you sent your good short story out to a lesser mag to begin with.
You have to start somewhere. Why sell yourself short? Why not aim high?