It's often said that if you want to be a better writer you need to do two things: read and write—a lot. This is both true and obvious. But it doesn't mean a little help won't go a long way. On the writing side, this help comes in many forms, the most common being the writing classes offered by universities across the country. And if you take a few of these classes you'll no doubt find yourself writing a bunch of short stories.
This is no accident. Short stories are, well, short, meaning the aspiring writer can put in a bunch of reps before tackling something more substantial.
On the reading side, the same holds true. Volume is important, but volume with guidance is better. Unfortunately, that guidance is harder to come by. Even if you take a class, there might not be much structure to the reading outside of the professor's taste in literature. So you might be writing short stories while reading novels. You're also likely to find some how-to books, not all of which are bad. (The two I'll recommend are Stephen King's On Writing and Jon Franklin's Writing for Story.) And when the assigned reading consists of short stories, they tend to be anthologies, like the Best American series, rather than collections from a single author.
This is misguided. There is one kind of book that will teach you more about writing than any other, and it's not a novel or a how-to; it's the humble short story collection.
This doesn't mean I don't read novels, or that I think anthologies are crap. I tend not to trust book reviews, so anthologies are the primary way I find new authors—and their novels. More importantly, to read an anthology with your writer hat on is to expose yourself to repeated examples of how authors tackle different technical problems: introducing characters, handling flashbacks, using metaphor, dialogue, etc. Single-author collections do all of this as well, but they have one advantage. In single-author collections, technical tricks and story themes that you might not have even noticed when reading a one-off story begin to jump out at you.
It's the difference between asking yourself, How does this story work? and asking yourself, What is this writer up to?
Take Shirley Jackson. I recently finished her collection The Lottery and other stories, named after her most famous and influential piece. And while "The Lottery" is a dope story, what I found myself thinking about as I put the book down was a pattern I'd noticed in which she organized many of her stories ("The Lottery" not included) so they arrived at a kind of weird climatic twist.
Jackson follows this pattern in at least four of the book's stories: "Like Mother used to Make," "Trial by Combat," "Seven types of Ambiguity," and "Come Dance with Me in Ireland." The stories, which are all quite different in terms of setting and plot, establish a kind of hero who the reader roots for. The hero must deal with a another character, who is a little bit off, socially. And in every story something happens at the end that negates much of the hero's actions, revealing the situation to be more complicated than the reader had realized.
In "Seven Types of Ambiguity" for example, a student in a bookstore is hoping to save enough money to buy a special edition book kept behind the counter. When a rich couple comes in looking for books to fill the shelves in their new home (the couple is clearly ignorant of literature), the student helps them. He then leaves the store as the couple pays the shop owner. When paying, the couple ask the shop owner to throw in the special edition book that they know the student wants. This is the climax. The reader hopes the couple will give the book to the student, but they don't. He's gone. Instead, the book will sit on their shelf at home, unread.
Maybe that doesn't sound like a great short story to you. It doesn't really matter. The important part is spotting the pattern. Now, I can try to deconstruct it, looking at pacing, how Jackson uses tension, and how she builds in a surprise that is not out of character. A good writing exercise might be to write my own story to fit Jackson's pattern.
In a sense, the great Shirley Jackson has become my teacher.