Many students struggle in writing the college essay. Over the years, I have read many books, hoping to find the "perfect" one to assist my students in what can easily become a grueling process.
Surprisingly, my favorite source came not from a college admissions book but from a short essay written by one of my favorite radio personalities: Ira Glass, host of the public-radio program This American Life. If you've listened to his show, it's a real treat and a great model for storytelling.
Below I excerpted his article "Tell a Story" found in Samantha Ettus's The Expert's Guide to 100 Things Everyone Should Know How to Do.
Start your story with a provocative piece of bait. This can be a big original thought about the action that's about to come, like: "Happy families are all alike; every unhappy family is unhappy in its own way." That's the sort of thing you might invent if you were one of the greatest writers who ever lived. If you're more like me, simply reach for an original, snappy-sounding idea that might be more or less true: "Society has a deal with people in certain unpleasant jobs." Or: "Like you, I'm tired of the Internet."
The other way to begin a story, the easier way, is simply to get the action rolling: "Last night I dreamt I was in Rome again." "Marley was dead to begin with." Classics. You just start things in motion, let one even lead to the next.
Remember, at its heart, a story is simply a sequence of actions. This thing happened, and then this, and that led to this. If you do it right, the sheer momentum will keep people engaged, because it'll feel like it's all leading somewhere. Also, handily, a sequence of actions, laid out this way, will generally raise questions ("What happened in Rome?" "Who's Marley?'), and unanswered questions are more bait, pulling people deeper into your story.
Be specific in the details. The surprising, telling detail is part of the pleasure of a story. In his account of attending a summer camp for American kids in Greece, David Sedaris explains that they'd to gift shops and shoplift “pint-sized vases, little pom-pommed shoes, and coffee mugs reading SPARTA IS FOR A LOVER." In any piece of writing, the more you're in it to amuse yourself, the better it'll be. Work in stuff you find funny, or moving, or interesting. If you never find things funny, moving, or interesting, please don't try to create stories.
Part of the craft of telling a story is sensing when you should keep the action going, and when you can pause for description, or some little observation you make, or an interesting digression. In many kinds of stories, you'll want to stop the action for a moment of reflection about what the point of the story is...
In most stories, we watch someone go through an experience, and it leads to some new perspective about the world—usually for them, but sometimes only for us. Sometimes this new perspective is stated straight out. Sometimes we observe the characters' transformation through their actions. They get into situations we've seen them in before but now they act differently. If no on in your story changes and no one learns anything, Seinfeld not withstanding, it's probably not a story.