Looking back, it's pretty absurd that my high school's college essay counselor didn't teach me the conventions and purpose of the personal essay as a literary form. Having your clients read great personal essays is such a smart move. Love it.
I graduated from one of the schools he was rejected from and I am 100% certain my supplemental essay made all the difference. Applicants were asked to explain how their favorite piece of art (painting/music/book/etc) impacted them. I wrote about my favorite novel. But even I knew at 17 that admissions wasn’t asking for the sake of asking, they really asking “what is inside this girl’s heart and head that others can’t see?”
Every year a story like this goes viral and it is always the same type of student with an application and personal essay that shouts “I have no inner life.”
when AI writes and reads all our emails and applications, we will once again have to meet and know each other by walking down the street and talking face to face
“I start by presenting them with the personal essay as an art form — I might have them read David Sedaris or George Orwell — and then zero in on the college essay once they understand how to put together a successful piece of writing.”
Going through this myself currently applying to Masters program. I feel like I can write anything sometimes, but never feel like I can write the college essay, haha. Applying for a masters is its own weird point in the personal timeline. Not young anymore, so it feels weird to write so vulnerably, but you’re old enough that you should have some wisdom.
Once upon a much more innocent time, when I was a naive and successful college applicant, I would have considered using a coach on the essay the equivalent of cheating on an exam or plagiarizing a paper. When I wrote my personal essay I saw the challenge as saying something about myself without writing about myself, since the application had already required short essays on my academic and extracurricular interests. (I wrote about a particularly influential teacher I'd had.) That I was able to frame the challenge without coaching and execute an effective response demonstrated something real about my abilities
Over a long period of time, a good editor can certainly teach you to write better. But hiring one for one essay still strikes me, 45 years later, as profoundly dishonest. So much as I'd like writing ability to count for something in college admissions, I'm on team no essay--even without considering the effects of AI editors.
Thank you, Lisa -coming for a different culture, the need for the personal essay, in its most common form, the one that you critisize, was baffling to me. Infuriating, at times.
personal "anecdote"-my kid overhearing conversation in her high school:
"X have cancer"-"wow, she's so lucky, it's a great essay material!"
maybe these two girls talking were particularly dumb for their age, I hope so
thank you for reframing it to me in a different way
Here's my question: How does he know that the essay is the reason he got rejected? Or does he just assume that is the only objectionable thing in his application?
That kid’s problem is that he’s trying to impress a world that no longer exists. He’s selling black and white TVs in 1965. That’s probably a good enough essay to have been accepted to good schools in 2015, but it’s not 2015 anymore. In 2025, you don’t need smart guys to write code anymore, even if they’re good at selling that code. AI can do that for you. If the Winklevoss twins were 25 years younger, they wouldn’t have needed to hire Zuckerberg to code Harvard Connection. They could’ve just prompted ChatGPT.
What will matter in software going forward is understanding users: what they need and why, how they use a product, what causes them irritation, etc. This is actually what mattered in software in the past, too, but past founders were also coders and so they myopically saw their coding ability as their unique value proposition. And of course, it’s what matters in non-software businesses, often with similar shortsightedness. A successful chef thinks his restaurant succeeds because of his cooking, but the world is full of talented chefs whose restaurants failed. If you’re looking to invest in a restaurant, the question to ask is not “is this guy a good cook?”
What’s interesting is that this kid probably has something to offer besides his ability to write code. He’s just too wrapped up in one limited self-conception to realize the other aspects of his personality.
So it ended up being an essay that said kind of a lot about him as a person. Alas, what it said was that he doesn’t have a lot of foresight and naively expects things to stay the same as they’ve been because the way they’ve been benefits him, and that he lacks the ability to pivot when circumstances change. So yeah, of course he was rejected. Elite colleges are looking for future distinguished alumni, not trend riders.
Disclosure: I work in software and my job might be negatively impacted by AI. But I was a humanities major. I both have experience with tough job markets and have a broad enough background so that in the long term it won’t matter.
By age 7, I was coding. By 10, I was giving lessons for $30/hour. By 12, I published my first app on the App Store. By 14, my online gaming website was earning $60,000 annually. And by 16, I had a six-figure exit. YouTube was my personal tutor, teaching me everything from programming to filing my LLC’s.
Why did he want to go to college? Sounds like he went to the college of life and succeeded without having to spend 100k a year. Did he just want the fancy degree from an elite school?
This is an astute and badly needed reminder that the ‘personal’ in “personal essay” is an exercise of self-knowledge, one of the rare intellectual tasks still demanding a soul rather than a brand, not a bureaucratic checkbox.
What so many miss, both critics like Mounk and performative meritocrats like Yadegari, is that elite colleges are sniffing out the kind of success that smells suspiciously of algorithmic ambition, and not rejecting success. The problem isn’t achievement — it’s achievement without interiority, a résumé dressed up as a memoir.
To me, the deeper tragedy isn’t that students like Yadegari fail to “sound human”, it’s that our culture has raised a generation for whom being human is now a performance reviewed by a panel of strangers. We have taught them how to optimise, monetise, and brand themselves to death, but not how to think about who they are when the metrics disappear.
The college essay, when properly understood, is less a PR campaign and more a trial by intimacy. It’s the moment the admissions officer asks, “Will I be stuck sitting next to this person at 2am during a philosophy seminar, and will they say something — anything — that isn’t copy-pasted from LinkedIn?”
We currently live in a society in which the humanities are treated like quaint relics and AI increasingly mimics “insight,” the simple act of narrating one’s own life (messily, vulnerably, unsellably) becomes revolutionary. Colleges are looking for signs of an unscripted mind, not perfection.
And that, ironically, is one thing no $60,000 gaming website can buy.
Looking back, it's pretty absurd that my high school's college essay counselor didn't teach me the conventions and purpose of the personal essay as a literary form. Having your clients read great personal essays is such a smart move. Love it.
I graduated from one of the schools he was rejected from and I am 100% certain my supplemental essay made all the difference. Applicants were asked to explain how their favorite piece of art (painting/music/book/etc) impacted them. I wrote about my favorite novel. But even I knew at 17 that admissions wasn’t asking for the sake of asking, they really asking “what is inside this girl’s heart and head that others can’t see?”
Every year a story like this goes viral and it is always the same type of student with an application and personal essay that shouts “I have no inner life.”
when AI writes and reads all our emails and applications, we will once again have to meet and know each other by walking down the street and talking face to face
“I start by presenting them with the personal essay as an art form — I might have them read David Sedaris or George Orwell — and then zero in on the college essay once they understand how to put together a successful piece of writing.”
May your tribe increase.
Going through this myself currently applying to Masters program. I feel like I can write anything sometimes, but never feel like I can write the college essay, haha. Applying for a masters is its own weird point in the personal timeline. Not young anymore, so it feels weird to write so vulnerably, but you’re old enough that you should have some wisdom.
Once upon a much more innocent time, when I was a naive and successful college applicant, I would have considered using a coach on the essay the equivalent of cheating on an exam or plagiarizing a paper. When I wrote my personal essay I saw the challenge as saying something about myself without writing about myself, since the application had already required short essays on my academic and extracurricular interests. (I wrote about a particularly influential teacher I'd had.) That I was able to frame the challenge without coaching and execute an effective response demonstrated something real about my abilities
Over a long period of time, a good editor can certainly teach you to write better. But hiring one for one essay still strikes me, 45 years later, as profoundly dishonest. So much as I'd like writing ability to count for something in college admissions, I'm on team no essay--even without considering the effects of AI editors.
He also spelled “rite of passage” incorrectly.
The SAT can’t be gamed either. You take it in person and you can’t pay someone to cheat for you (as easily as you can the essay at least).
They should quit asking personal questions and give the kids a passage from literature and ask for a quick analysis.
Thank you, Lisa -coming for a different culture, the need for the personal essay, in its most common form, the one that you critisize, was baffling to me. Infuriating, at times.
personal "anecdote"-my kid overhearing conversation in her high school:
"X have cancer"-"wow, she's so lucky, it's a great essay material!"
maybe these two girls talking were particularly dumb for their age, I hope so
thank you for reframing it to me in a different way
Here's my question: How does he know that the essay is the reason he got rejected? Or does he just assume that is the only objectionable thing in his application?
That kid’s problem is that he’s trying to impress a world that no longer exists. He’s selling black and white TVs in 1965. That’s probably a good enough essay to have been accepted to good schools in 2015, but it’s not 2015 anymore. In 2025, you don’t need smart guys to write code anymore, even if they’re good at selling that code. AI can do that for you. If the Winklevoss twins were 25 years younger, they wouldn’t have needed to hire Zuckerberg to code Harvard Connection. They could’ve just prompted ChatGPT.
What will matter in software going forward is understanding users: what they need and why, how they use a product, what causes them irritation, etc. This is actually what mattered in software in the past, too, but past founders were also coders and so they myopically saw their coding ability as their unique value proposition. And of course, it’s what matters in non-software businesses, often with similar shortsightedness. A successful chef thinks his restaurant succeeds because of his cooking, but the world is full of talented chefs whose restaurants failed. If you’re looking to invest in a restaurant, the question to ask is not “is this guy a good cook?”
What’s interesting is that this kid probably has something to offer besides his ability to write code. He’s just too wrapped up in one limited self-conception to realize the other aspects of his personality.
So it ended up being an essay that said kind of a lot about him as a person. Alas, what it said was that he doesn’t have a lot of foresight and naively expects things to stay the same as they’ve been because the way they’ve been benefits him, and that he lacks the ability to pivot when circumstances change. So yeah, of course he was rejected. Elite colleges are looking for future distinguished alumni, not trend riders.
Disclosure: I work in software and my job might be negatively impacted by AI. But I was a humanities major. I both have experience with tough job markets and have a broad enough background so that in the long term it won’t matter.
By age 7, I was coding. By 10, I was giving lessons for $30/hour. By 12, I published my first app on the App Store. By 14, my online gaming website was earning $60,000 annually. And by 16, I had a six-figure exit. YouTube was my personal tutor, teaching me everything from programming to filing my LLC’s.
Why did he want to go to college? Sounds like he went to the college of life and succeeded without having to spend 100k a year. Did he just want the fancy degree from an elite school?
This is an astute and badly needed reminder that the ‘personal’ in “personal essay” is an exercise of self-knowledge, one of the rare intellectual tasks still demanding a soul rather than a brand, not a bureaucratic checkbox.
What so many miss, both critics like Mounk and performative meritocrats like Yadegari, is that elite colleges are sniffing out the kind of success that smells suspiciously of algorithmic ambition, and not rejecting success. The problem isn’t achievement — it’s achievement without interiority, a résumé dressed up as a memoir.
To me, the deeper tragedy isn’t that students like Yadegari fail to “sound human”, it’s that our culture has raised a generation for whom being human is now a performance reviewed by a panel of strangers. We have taught them how to optimise, monetise, and brand themselves to death, but not how to think about who they are when the metrics disappear.
The college essay, when properly understood, is less a PR campaign and more a trial by intimacy. It’s the moment the admissions officer asks, “Will I be stuck sitting next to this person at 2am during a philosophy seminar, and will they say something — anything — that isn’t copy-pasted from LinkedIn?”
We currently live in a society in which the humanities are treated like quaint relics and AI increasingly mimics “insight,” the simple act of narrating one’s own life (messily, vulnerably, unsellably) becomes revolutionary. Colleges are looking for signs of an unscripted mind, not perfection.
And that, ironically, is one thing no $60,000 gaming website can buy.