Why Your Essay Feels Fake (And Why You're Stuck)

Nothing stifles creativity and creates inauthenticity like being judged, assessed and compared to others. Unfortunately, that's precisely what a college admissions officer is going to do with your essay. This is the core tension I navigate with many of my students. How do you feel safe enough to say how you really feel, within the context of a system that's judgemental and competitive?

One technique that works well is to exit that system entirely for a moment. Put the essay aside and go tell a trusted friend your "real" answer, with no agenda or expectation other than to communicate your truth to someone else.

One time, I was coaching a student who wanted to write about how their time living in Mexico City shaped their values. They had brainstormed a few ideas for how to tell the story, but nothing was really landing. So we put the essay aside for a moment and I asked them: how were you actually shaped by living in Mexico City? What is the real answer to that question?

We followed that thread and discovered multiple ideas for compelling, unique, and authentic stories. These stories don't often emerge from the outset because students think their "real answer" is too mundane or not impressive enough, so they feel pressure to conjure up something better. But in almost every case, we've been able to work the authentic answer into a better story, because it came from a place of realness.

When coaching the band System of a Down through a case of writer's block, producer Rick Rubin famously instructed frontman Serj Tankian to open a random book and just start reading. He picked up the Bible. The first phrase he saw was "Father, into your hands I commend my spirit. Why have you forsaken me?" which became the bridge to the song "Chop Suey!". It had nothing to do with the rest of the song. But for whatever reason, it worked.

This technique can yield unique, unusual sources of inspiration for the direction of your essay. But it's also tricky to put into practice. I've found that many students have been taught to think in terms of "right" and "wrong" answers to problems, with the "right" answer attainable with enough effort and perseverance.

While this works well for STEM problems, it can hinder the creative process, because the best ideas often emerge spontaneously, fueled by unexpected sources of inspiration. It's not a process that can be controlled. This is where a good coach can help guide you.

Mark Twain said "I didn't have enough time to write a short letter, so I wrote a long one instead." I've found students sometimes think more words, more examples, and more description strengthens their point. Oftentimes, it doesn't.

Writing is a bit like baking in this way. Adding more ingredients to the recipe, even if each of those ingredients are individually delicious, can easily ruin it. Even when you have nailed the recipe, making the cake bigger doesn't make the cake better. Your diners can only eat so much before they start to lose appreciation for your flavor.

This is why some of the fanciest desserts at Michelin star restaurants are small, simple, and innovative. To Mark Twain's point, writing less is counterintuitively actually harder than writing more, because it forces you to distill what it is you're really trying to say clearly and concisely.

This is why I use the following exercise to strip an essay down to its bare essence, and build it back up from there:

Write at the top of your page: "What I'm really trying to say is..." and then write no more than three sentences. No fancy language, no college essay voice, just the core truth. Often these three sentences become the anchor that the entire essay needed. Everything else can be built back up around that central insight.