For the Ideal College Essay, Follow These Steps

We’re going to drill down into a particular kind of essay that will not only help you sell yourself to colleges; it just might change your life.

First, let’s talk about what a personal essay is and what it does. The term essay comes from one of my heroes, Michel de Montaigne. He’s famous for having invented the essay as a literary form. He called it an assais. Or, in English, an assay. That’s where you melt down a metal or other substance to analyze it. See what it’s made of. Determine its worth. At the advaßnced age of 38, Montaigne decided to do this with himself. In the middle of a terrible pandemic, he retreated to his chateau to examine himself—under the assumption that, as a human, he shared the most important traits with other humans. By assaying himself, he would assay all of humanity. 

And this is what you need to do in your college essay: assay yourself. Show your worth as a candidate. Make the admissions officer fall in love. And this is what you need to do in your college essay: assay yourself. Show your worth as a candidate. Make the admissions officer fall in love. 

Let’s start with the Don’ts

First, don’t brag about how awesome you are.

Admissions officers tell me they get way too many of these types of essays:

1.     How I learned I was an amazing leader. As captain of my soccer team, we were about to lose the championship when I discovered at the last minute that I had the ability to inspire my teammates!!!

2.     The day I discovered that foreigners are actual people. My rich parents sent me abroad so I could learn how to use “empathy” in every other sentence. 

3.     My grandmother taught me values, and then she died.

Actually, that last one  doesn’t count as bragging. It’s just that admissions officers tell me they’re sick of reading about grandmothers. Too many students do that.

Well, so what? Why can’t you just write about whatever you want? Because the college essay is not just a literary exercise. It’s a rhetorical one. It’s a sales document, an act of persuasion. And the first rule of rhetoric is… 

It’s not about you.

Rhetoric is all about the audience. It’s about getting and holding their attention, gaining their trust, and convincing them. Before you can do any of those things, you have to know a bit about your audience. For one thing, she’s bored. She has to read thousands of these essays—thousands of grandmothers and trips abroad and young awesomeness. Or she’s seeing a wordy repetition, full of “life journeys” and “empathy” for strangers. 

Meanwhile, she’s looking for something—something she rarely sees often enough. A particular trait that she usually can’t see in a transcript or board scores, or even in alumni interviews. Focus on that one thing, and you’re on your way to a winning essay. One that hits the bullseye with your audience. 

And what is that one thing? Let me keep you in suspense for a minute longer. Because I can already hear your objection:

What about the prompts? 

I mean, what about the questions the Common Application lets you choose from? And what about the prompts individual colleges use? 

Well. As every media consultant will tell you, you should give the answer you want, regardless of the question. In the case of essay prompts, I’d suggest ignoring them at first—just ignore them; at least until you’ve written a draft or two. Focus instead on the one thing the admissions officer is looking for. And that one, most important thing she’s looking for is…

Your ability to grow.

That’s the main secret to a winning essay. Every admissions officer I’ve talked to says this is the most winning trait, the one that doesn’t show up in transcripts. An ability to learn, to adapt, to change—to grow: this reveals the student who will get the most out of a college education. 

And it’s especially important if you don’t happen to be perfect, if you didn’t do a jillion activities and score perfect grades from age three on. Plus, a character’s growth and change form the backbone of every great story. Which is what every winning college essay should do.

1.     Show an ability to grow.

2.     Tell a great yarn.

When you look at the prompts, you can see that a personal growth story works for every single one of them. So never mind the prompts. Make sure your essay does these two things: growth, and storytelling.

Now let’s talk about how to achieve that.

We’re about to go over the details of a very specific kind of essay. I call it the epiphanic essay, because it has to do with an epiphany—a discovery, a moment of sudden awareness. 

An epiphany usually starts with some sort of crisis, an internal conflict. 

So that’s what you’re going to start with. You’re going to write a sentence or two that sums up the whole deal: your personal crisis that leads to a moment of self-discovery.

Huckleberry Finn faces just such a crisis when he has to decide whether to turn in his friend Jim, a runaway slave. As a good southerner, Huckleberry knows it’s a sin not to return stolen property. And Jim has stolen himself. But Huckleberry chooses friendship over his own moral code. All right, he says to himself. “I’ll go to Hell!” And he instantly grows in this self-discovery. 

Huck Finn’s pith: Should I obey the law or save my friend?

In Paulette Jiles’ wonderful novel, News of the World, a young girl learns to trust a man she has been taught to believe was her enemy. A white girl captured by Plains Indians who treat her as one of their own, she learns during a battle to love an old man who should be her worst enemy. 

The girl’s pith: Can a white man be my friend?

But the best example I can give is that of my son George. At the beginning of seventh grade, he developed chronic headache syndrome—a splitting headache that can lasts for months, even years. It gets triggered by a virus, and in a type-A person like George, it creates a sort of negative feedback loop: the headache causes stress, which makes the headache worse. Like Huck Finn, he found himself confronting his own type-A identity. He spent a whole miserable semester out of school, lying on our living room couch. Eventually, he ended up in a psychologist’s office with wires attached to his head, trying with his own brain to make a set of red bars on a computer monitor all turn green. The psychologist, a Dr. Kravitz, was a biofeedback expert. He tells George that the way to change the bars on the screen is to let go of his struggles. Dr. Kravitz tells him, “Try not to try.” 

Being the goal-oriented type he is, George sits down at the machine and pushes his brain. “Uuuuggggh!” He’ll make those bars turn green. And of course they don’t.

This is the pith of his essay, the moment of greatest conflict, on the edge of his epiphany, when he learns the secret of trying not to try. 

Is it easy to come up with this sort of pith, a moment when you have to rethink your very you-ness? Of course it’s not easy! Writing isn’t easy! 

Anyway. Think of a moment in your own life, when your own identity was challenged. When it made you miserable, or when you discovered you were wrong about yourself, or when you found that the very trait that made you such a loser turned out to be an asset.

Let’s try the epiphanic technique on the topics that are boring those poor admissions officers across the land.

Instead of “How I discovered I was an amazing leader…”

I suddenly realized that the best way to lead may be not leading at all.

An epiphanic essay on leadership might have as its pith the moment when the weakest member of the team inspired all the others, making the writer suddenly realize that leadership means more than being the best at something. It means discovering the best in others.

What about the foreign-trip essay, the one where the kid finds that primitive backward people are actually human? Well, a great pith might be this:

I watched in disgust as one of the high-status people treated a lower-ranked member of the village with condescending scorn. And I realized that I had done exactly the same thing every time I told a non-PC joke.

For the grandmother essay, a pith might be something like:

When I showed her my prizewinning watercolor, she went up into the attic and brought down a box. It was full of the most beautiful art, including watercolors. I suddenly realized I wasn’t so unique after all. Instead, I felt like a link in a wonderful chain.

So that’s the pith: I thought I was special, and learned I was a part of something much bigger. 

Or, the thing I was proudest of, the trait that made me, me—was exactly what was bringing me to my knees. As in George’s essay.

Or, what I thought was a good thing—something that made my kind special—was actually the worst kind of sin.

Or, my biggest weakness, something I was most ashamed of, became my biggest source of strength.

Got it? The pith is the first thing you write—just a brief note about how your identity was challenged. It might take a long time to craft your pith. Which is why it’s a really bad idea to try and write a college essay in one weekend. Or even one month.

Back to George and his essay. At this point—actually, after a couple weeks of trying to figure out what the heck was the pith of his essay—he had his moment of maximum conflict. It was also the climax of his story, though he didn’t realize it yet. 

So let’s turn to the next step.

One of the biggest mistakes beginning writers make when they try to do an outline is to write it in proper order—writing the beginning first, then the next part, then the next, and so on until at last you put down a few words for the ending. This defeats the purpose of an outline. You might as well just write the darn essay.

To make the outline work, you need to first put down the elements in no particular order. What do I mean by elements? Let’s look at George’s story:

First of all, there’s the pith: My type A-ness is ruining my life, and I need to find a way to deal with it. 

OK, what other elements are there? He lists a bunch of scenes, descriptions, and actions. Again, these are just the various parts he’s laying out. Sort of like the scene in Deadpool where the blind woman lays out the parts for the Ikea furniture-- Kullen. Or was it the Hurdal? Love that movie.

The elements list just lays out the parts. Then, once you have all the parts laid out, you mess around with them. See what order to put them in. Which is the next step in crafting our essay. You write an outline.

The classic way to organize a story is the Hero’s Journey.

The main character leaves home, or his comfort zone or whatever, because of some sort of challenge or conflict. She may be reluctant at first, but ends up committing. She attempts some solutions, tries and fails. Along the way she gathers knowledge and maybe an ally or two—a wise counselor, or friends, or fellow warriors. Alone or with the others, the hero overcomes obstacles, deals with setbacks…and ends up in a climactic battle. Or on a ledge. Or at a moment of truth. Or in a mind-blowing dialog. In any case, the climax constitutes a clash of opposing forces. And its outcome is some sort of victory for the hero, often an unexpected kind of victory. And, most important, the hero learns something to take back to the village. Or, to college. Whatever.

George’s essay topic seems perfect for a hero’s journey outline. He arranges the elements in an outline that tells his hero’s journey, and tweaks some of those elements along the way. In one of those elements, he begins to ask himself questions. The first question he asks himself is if he should be like Job, in the Bible. God gives Job boils, kills his family, takes everything he has, but in the end Job accepts his fate. God puts everything back to rights. So let me show you the end of George’s essay, when he asks the questions while staring at a beautiful picture on the wall of a field of grass.

What if I acted like Job? Would my life come back? Maybe this is what trying not to try is like. Instead of putting myself in the field, what if I simply let the field be the field?

One bar goes green.

Okay, one bar is green. I’m starting to get what the doctor is saying, but I don’t really like it. Will this be one of life’s limitations, spending the rest of my life trying not to try? Will I have to change who I am?

The world has expanded for me and I am no longer the center. Sure: I can’t change everything. And there is the crux of the whole thing: I’ll always be hardheaded and stubborn. Still, as I look at the painting it comforts me. It’s perfect and peaceful without me. It’s beautiful all on its own. I don’t have to do anything. 

Accepting things that are beyond me, being comforted by something that exists regardless of what I do: is this what faith is?

All the bars turn green.

Forgive me for bragging about my son, here, but that essay ended up being one of five that were read to the entire first-clear class at Middlebury College. And I’m convinced it helped George sell himself to the school. He portrayed himself as a seeker of wisdom. One who can grow and change, who’s willing to challenge his own identity. And who knows a great epiphany when he sees one. All by writing about his headache. Which was entirely his idea.

Keep in mind that this kind of essay isn’t easy to pull off. And it shouldn’t be. The epiphany comes after a struggle, and so does this essay. You should maybe write a bunch of piths to find that one that truly suits you. Then, be prepared to rewrite the list of elements several times before even attempting an outline. Once you draft the essay itself, you should be willing to rewrite it a bunch of times. Make every sentence beautiful and rhythmic, full of concrete details, and clean of all clichés. Then work on transitions between paragraphs, so that one flows inevitably into the next. Focus on the climax, the moment of truth—your epiphany. Finally, experiment with different endings. The ideal ending should make the admissions officer gasp. 

And take your time. Even Shakespeare probably did his share of rewriting.

Is it worth it?

I believe that the college admissions essay is one of the most important pieces of work any student can do in high school. And not just because it can help you get into the college of her choice. It’s much more than that. 

The essay truly is an assay, a self-examination. And I’m not just talking about the aspiring writer. I’ve worked with students who went on to brilliant scientific careers, or became accomplished photographers, successful business owners. All of them tell me that this act of assaying themselves was one of the fundamental moments in their maturity. 

But wait, there’s more.

There’s an old story I heard at Dartmouth, about a classics professor who taught a course in ancient Greek. When only one student signed up for the course, the professor went ahead and taught it anyway.

A colleague said to him, “Why on earth are you teaching that entire course to just one student?”

And the old professor reared up and said, “To save his immortal soul!” 

And that is the moral to my story here. Why do you go through the agony of teaching such a torturous writing exercise?

To save your immortal soul.