Recently, I coached a student through a college-application process. It occurred to me that many readers will need to do this at one time or another (as parents, or aunts, or uncles), so I'm collecting a few thoughts here:
(1) Don't talk down. Treat the kid as an adult. If he voices frustration, that's a good thing. (If there isn't a struggle, there isn't any learning.) If all the material doesn't sink in now, it may nonetheless sink in two years from now.
(2) Walk the walk. I think, if you're helping a kid with a college essay, it's only fair that you yourself draft a "college essay." Let the kid see your multiple failures and your rare epiphanies. ("Rare" if you are *yours truly* .....) Do you know how easy it is to wag a finger and say, I told you to write FIVE rough drafts? Do you know how much harder it is to go ahead and write five rough drafts? Do the drafts from your own point of view--and your finger-wagging will take on new authority.
(3) A good draft is a mix of detail and reflection. Too many pieces traffic in generalization: "I discovered myself as a team member." "I added my own style to the role." On the flip-side, a draft can be *all* sensory material, without any lessons learned. The right essay is in the sweet-spot between PROBLEM CASE "A" and PROBLEM CASE "B." (For an example, see the NYTimes: "This Is the Racism That I Face at My Elite High School.")
(4) Every writer has a gender, a race, and a family history, and most writers have a religion. These areas may feel uncomfortable; they are areas to visit, and then the writer should stay, and stay, and deal with the discomfort.
(5) It's very likely you can throw away the first two or three paragraphs. Again, this will make a teen cringe. Again, it's generally necessary.
That's how I would approach an "essay" meeting.
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