Well again, I might not of stated it correctly but everyone was laughing at Emory when she said it. She was actually pretty funny and it was enjoyable coming directly from Georgia Tech in the morning, that was pretty intense. This was in the afternoon. But again the point was girls talk and boys don’t. It took us a long time to get our engineering hopeful to talk openly about himself so I understand where the OP is coming from. It was like pulling teeth 
One thing that helped my kids was to look at old photo albums. A thing of the past, I know, but the digital equivalent. They wrote about blueberry muffins in the morning, Legos, and rubber erasers. Essays do not have to be weighty and poignancy can come from unexpected topics.
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Tell your son to write whatever he would like to write about. Make it quick & easy.
This is your son’s current state of mind. Forcing him to write something that conforms to anything other than the essay prompt is not likely to yield positive results at this time.
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I’m going to be blunt here-- since my fellow posters seem to be trying to be polite.
You are WAY too involved, and you are grossly over-estimating the importance of a “self reflective essay”.
Most admissions essays- even to mega competitive colleges- land somewhere between “adequate and fine”. A brilliant essay won’t get a kid into a college if the rest of the application isn’t a fit for that particular college, and a somewhat prosaic (but grammatical) essay won’t keep the kid out if there’s something else there that’s compelling.
Most HS kids cannot produce Pulitzer quality writing and adcom’s know that.
If you are starting the Battle of the Application now- in June- you are in for a very long, tedious, stressful and tear filled senior year (not sure whose tears but for sure there will be tears). Encourage your kid to pretend that he’s writing a piece of fiction- something that happened to someone else, using nouns and verbs and a few adjectives. If he likes it enough to use it for an essay, he can have a surprise ending- pointing out that it happened to someone else, is pure fiction, it was in a dream. If it’s clearly sci-fi or fantasy (two genres that many HS boys love) he doesn’t even need the disclaimer.
“I’m trying to get him to edit it and getting a lot of pushback. But people – if this program is in any way competitive, he’s not going to look very strong. And this is just a taste of what it will be like when he starts having to work on college essays in a couple of months.”
Every time you say (or he senses) that his writing is banal or boring or prosaic what he’s hearing is “I’m a terrible writer, why bother”. So figure out how to get yourself out of the toxic mix of editor/critic/demotivator.
Every single essay my kids produced for colleges (including the short “why us” statements) ranged from atrocious to dumb to juvenile to “barely acceptable”. Each had an English teacher read them for overall grammatical and stylistic consistency-- and that was that. I am a major control freak and truthfully- was freaking out. But my kids guidance counselors all told me to butt out- one of them told me point blank I was driving my kid crazy-- so I freaked out all by myself. They all went to college and have done really great things-- both academically and now professionally. Their writing skills have morphed from “barely OK” to outstanding-- college will do that for you. And it happened without me- can you believe it?
But you really need to choose your battles starting yesterday. And a summer program essay-- really? Not the hill to die on.
Sending hugs. Been there. Didn’t hire a writing coach or an anything because I knew my kids would refuse to participate and I’m too thrifty to spend money on something that won’t get used. And it all worked out. It will work out for your kid also!!! As long as he doesn’t start his Vassar essay with “All my life I’ve wanted to attend Brown” he’ll be fine…
You’ve hired someone-- either fire that person and hire someone else who might click more with your kid, or stand back and let that person do their job.
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