Happy families are all alike; every unhappy family is unhappy in its own way. -
Anna Karinina, Leo Tolstoy. Chapter 1, first line.
I can't recommend a single book. Every aspiring writer is also unhappy in their own way; there is no book entitled
How to write a good short story that isn't a lie for that reason. I recommend a number of different books to address different issues. Some people need help finding their voice as a writer. Some have no sense of plot. Some need help finding the time, energy, space and drive to write. These are clearly not your issue so we'll gloss over them.
Your first question is one it seems you know the answer to, but don't know that you know it because you've approached the question from the wrong direction. There is no way to quantify what makes great short stories great because it's not the same. It's uniquely true of each piece.
The Lottery is a great short story because it hones in a primal part of ourselves that we're scared of, every line every word of that story forebodes; we'd like to think that because we're civilized enlightened creatures that couldn't happen anymore...then Jackson destroys that and it shakes us.
The Swimmer is a great short story because it presents us with a realist plot of a man to do something both meaningful and absurd which ultimately doubles as an allegory for the slow-unraveling of a life and the spiritual-bankruptcy as possessions replace relationships and society glosses over that void with the illusion of false-happiness and a "stiff upper lip", a plague which Cheever sees as prevalent in suburbia. It poses a question which makes us think...
If a nice house with a picket fence, a swimming pool, a car in the driveway and the nuclear family is the American dream, why are we so unhappy? Once, through his actions, Neddy finds himself outside of this illusion, he is lost. The end of the story is a parable...you can't go home again...but also a cliffhanger: Who would ever choose to go back to the illusion and if you can't go back to the way things were...where do we go from here? What makes one great is not what makes the other great.
The Gift of the Magi by O. Henry is a great short story because we all wish we could be that selfless; we feel for the characters at the same time that we suspect that they've learned something in their sacrifice which we'll never know.
So...where do we go from here as writers? I tell all starting-out writers (regardless of their chosen writing format) the same things:
1.) Write what you know and what you enjoy reading. If you enjoy cowboy stories, write about cowboys. (Larry McMurtry) If you enjoy the psychological drama of family life, write about that. (Henrik Ibsen) If you're a unhappy mid-level executive with a rich escapist fantasy life, write about that. (James Thurber)
2.) Show, don't say. Which one really tells you something about Damon?:
- Damon was a bad man.
- When Damon needed smokes, he'd follow an old woman home from the supermarket and into the elevator. Once the elevator started moving, he'd crack her skull with his pipe-wrench and steal her wallet. Easy money every time and no worries; any witness met the same fate.
3.) Adverbs suck badly. Don't use them, they're lazy and suggest poor verb choice. Again, which one reads better?:
- George walked slowly in the gutter.
- George skulked in the gutter.
The exception to this is when the adverb itself tells us something which can't be said in a better way (often in opposition to the verb):
- Nathan Hale marched warily towards the gallows, lingering for one opportunity to escape with his hard-won secrets which he knew would never come. He remained a soldier's spy until his end.
4.) Don't be afraid to have fun with language. Words tell us everything in a piece of writing. Be creative in your word-choice, a great word out of context can describe the unspeakable.
As the nails entered, Christ's wounds fulminated. Fulminated means "to explode with rage." or "let loose with profane invective." Find the character's voice...Juliet's monologue from Romeo and Juliet (Act II, scene 2) sounds awkward coming from Dolph Lundgren, adults don't say "poopie" and 4th graders don't say "whereas". Sometimes you want to break the rules of word-choice, it makes a story interesting.
5.) We have 5 senses with which we experience the world. Yet most writers get hung up on two: hearing and sight. I like to give my pupils a challenge to write a short story describing an experience by a blind deaf man.
As Henry picked up the new food in front of him, he felt its' flaky crispness even as the gooey chunky insides glommed between his fingers. It smelt of his father's orchard and his mother's hearth. In his mouth, it tasted sweetly of apples imbued with spring rains and the warmth of the sunshine. Apple pie would never taste as joyful to anybody else. I don't really buy into that
New Yorker style of writing or the "take the last sentence off" thing. A great first line and a great ending can make a mediocre middle great. I do think the one way in which that is true is that a lot of starting-out writers just don't know when to stop writing. You don't need to say "Happily ever after." although I did once to finish a really depressing story, it was the right ending for a story about a case of mistaken identity which ends in a public execution...because it was both unexpected and somewhat cynical...it certainly wasn't a happy ending for at least one character.
You're absolutely right in a sense, grant writing is short story telling...the motivation is the same.
Tell a story, tell me why I care. Help me see the problem or the world differently. Connect with the reader. Grant writing is about touching the emotional core of the reader, same as short story writing. I'm taking a online course in grant-writing now and one of the things that they keep saying is "don't describe the proposal, tell the story of the proposal and what the grant will do."
As for approach I take when tutoring...most of my pupils come to me with a writing piece in hand that they want to make better rather than an idea they want to write about. It helps me see what they need help on. In those cases that they have an idea but not a piece, I help them flesh it out and then send them home to write it. It doesn't have to be well-written but it's easier to work with a first draft than a premise.