The boy's college essay went on a brief hiatus while he was writing a paper for class. But now it's back, and better than ever. Over the course of two weeks, I'd given him a series of assignments: (1) brainstorm a list of words related his topic, (2) break that list into two parts--events and feelings related to the topic, (2) write sentences expanding on each of those items, (3) delete boring information and add details to more interesting information, and (4) organize the remaining sentences into paragraphs. I told him to ignore style, sentence structure, etc. He needed to focus on the rough materials.
By going through this process, the boy was able to produce a full-length draft, reasonably well organized and coherent but stylistically clunky. So my next assignment was "Set aside this draft. Now, on a clean screen, write the essay again, concentrating on creating beautiful, evocative prose. If necessary, use your first draft to help you recall your ideas and organization. Otherwise, ignore it." The result was remarkable. This draft was elegant, poignant, frightening, thought-provoking. Of course it wasn't done yet, but the piece had changed from serviceable information to well-crafted memoir.
Our next step was sit on the couch and look at the essay together as I read it aloud to him. This is an excellent way to help a young writer find typos and notice infelicities, repetition, and lack of clarity. When heard in the air, the beautiful prose is so beautiful that anything less beautiful sounds like a kicked garbage can. This read-aloud also helped him recognize that his ending was still muddled.
So this is where we are: he's doing some minor tightening, and he's rewriting the last few sentences. I expect he'll be finished by the end of the week.