Writing a College Essay is Harder than You Think

If you’re applying to college this year, you’ve probably read articles on the internet by “experts” offering tips and advice on how to write the perfect college essay. Sometimes these articles have titles like “How to Hack the College Essay” and “The College Essay Is Easier than You Think”; other times they provide you with screenwriting jargon and other technical language to make you think there’s a formula for success. If you follow their advice, they claim you’ll nail the college essay and get into the college of your dreams.

If only it were that simple! We’re a small company that works one-on-one with students on their college essays, and every single one of our tutors not only holds a PhD from a top institution but has also published a book with a prestigious university press. And even though each one of us has a decade of experience working with students on their college essays (not to mention many years teaching in top colleges), it’s always challenging to help new applicants come up with a college essay that will really stand out.

In previous blog posts, we’ve broken down why a lot of the advice on college essays is wrong. For example, we’ve written about why you should never use the montage structure for your college essay and why it’s a mistake to brainstorm your values at the beginning of the process. We’re also wary of anyone who tells you to read examples of college essays “that worked” or who breaks down the writing process into some kind of science.

But we realized the best way to communicate how hard it is to write a college essay is by giving a snapshot into what goes on in our one-on-one sessions with students. Our process is thorough and intense, and it produces good results - but boy, is it challenging!

Brainstorming your college essay is hard

In our first couple of sessions with a new student, we embark on the most difficult part of the whole process: coming up with a topic.

We begin by chatting with the student and doing our best to connect with them. This is essential: if a student doesn’t feel comfortable with a tutor from the start, they won’t voice their ideas, and the whole process will fail. We often tell students that “fit” is a critical part of the college essay process, and if you don’t vibe well with your tutor, it’s best to switch to someone else straight away.

Assuming the student does feel a connection, we begin a long discussion with them about their lives, focusing on what makes them unusual. We ask questions designed to get them to reflect on their past experiences, and we engage in a lot of back and forth. Eventually the student starts pitching ideas to us, and we push back on just about everything they say. Why? Because their early ideas are cliched, and we’ve heard them a thousand times before. This part of the process is exhausting; the student keeps bringing up new points about themselves, and we keep knocking their points back.

But at some point in this first session or two, the student will say something that strikes us as interesting or curious or odd or different. This always happens, and when it does, we push them to keep pursuing their line of thought. The student will become more animated as they speak, which is always a good sign.

After a while, we say, “Would you like to write your essay on this topic?”

Inevitably, the student answers, “Yes,” because this topic feels different to them. It feels like an authentic expression of themselves, not something they have in common with lots of other people.

Structuring your college essay is hard

Of course, identifying a topic is only the first step in writing a good college essay. The next thing we do is ask the student lots of questions, so they explore their topic from many different angles. Gradually, a kind of “thickening” takes place. We get a sense of the story they want to tell – but they desperately need help structuring it.

Why do students have so much trouble coming up with a structure? The reason is that they’ve generally never written a personal essay before, and they don’t have much experience with storytelling. They’ve probably come across articles on the internet containing gimmicky tips and technical terms (“montage structure,” “inciting incident,” “raising the stakes,” etc.) but these terms only lead to more confusion and don’t actually help students. They need some guidance to work out how to tell their story from beginning to end.

It’s important to emphasize that we never tell students what to put in their essays, and we never write a single word for them. Instead, through careful consultation with students, we come up with five or six questions that lead them through the storytelling process, step by step. In other words, we help them break their story into smaller chunks. There’s no template for this. We don’t provide the same set of questions to each student. Instead, we try to mirror back what each individual student is trying to say by devising the right set of questions for them.

In other words, this part of the process isn’t easy, either.

Writing your college essay is hard

Once students have an appropriate set of questions, we tell them to start responding to them as part of their daily homework. We emphasize that they should write everything that comes into their head at this stage and that the quality of their writing doesn’t matter. In fact, we usually say that they should “write badly,” because many students suffer from perfectionism or writer’s block. Our aim is to help students get their thoughts on the page, not come up with a final version of their essay.

Students return to us each week with writing that may be a bit rough, but that’s honest and authentic - which is exactly what we’re looking for. We compliment students when we notice them following the thread of their story, but we also provide blunt feedback when certain sections aren’t working. This can be challenging for many students; they’ve just spent the past week revising their work, and we basically tell them that it isn’t good enough. Nevertheless, they almost always accept our feedback, and they come up with new material, week after week. Eventually, they end up with a draft of a story that will hold any reader’s attention.

Many students assume that the writing is the most difficult part of the college essay, but that isn’t true. If you work hard on the brainstorming and structuring stages, the writing usually follows naturally. Still, it isn’t easy.

The final touches are easy

When students have a draft of their college essay that meets our standards, we provide minor grammatical and stylistic suggestions on Google Docs or Word, and the student emerges with a document that’s finally ready to submit.

This is by far the easiest part of the process for us. All our tutors have significant writing and editing experience, so they’re experts at spotting mistakes on the page. Sometimes students are amazed that we can make our suggestions so quickly and decisively, but in truth any experienced writer/editor with a PhD and a major publication should be able to provide this kind of feedback.

There are no hacks when it comes to writing the college essay. People may try to convince you that it’s easier than you think, but the opposite is the case. Hopefully this discussion of our process will allow you to see that it is possible to write a great college essay – it just takes a lot of work. 

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Why You Shouldn’t Write an Essay on “Any Topic of Your Choice”