When a short story is no longer a short story

Over the years, I've usually planned out my writing pretty well. I always felt that each element of the plot had a purpose and a place that added to the cohesive whole of the story. Consequently, I've really struggled with the concept of "killing your darlings." For those of you who haven't heard about this writing tactic, it essentially boils down to being able to let go of certain aspects of your story, especially when they don't add anything to the plot. Part of the reason I've been unable to remove some of these sections from my writing is because I find they're usually quite intertwined with the rest of the story and to remove them would require massive restructuring of the whole plot. To kill your darlings, you must be able to recognize them for what they are. In writing my short story for the next Midnight Writers' Anthology, I suddenly found the story I wanted to tell was much longer...
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