How to Write a Winning College Essay

Writing well is difficult. Writing well, while constrained to word limits as college essays often are, is even more difficult.

The challenge of producing a compelling essay can be due to a variety of factors. Perhaps, it may be since your audience isn’t clear and you have to guess. Or it may be because it is difficult to amalgamate the different stories and themes you wish to put together. Other times, writing is difficult because the personal storytelling writing style college applications ask for is vastly different from the expository writing style that dominates the classroom, AP exams, SAT testing, and other settings you’ve seen.

What distinguishes a good essay from a great essay varies from article to article. However, we can build a framework on how to tackle the problem by taking a look at rules some of the great writers follow. These rules can be broken down into two parts: the way you use words to construct sentences and the way you use words to construct stories.

George Orwell

George Orwell

First, let’s take a look at George Orwell’s 6 points, which he eventually implemented in his famous 1984 novel. 

  1. Never use a metaphor, simile or other figure of speech which you are used to seeing in print.
  2. Never use a long word where a short one will do.
  3. If it is possible to cut a word out, always cut it out.
  4. Never use the passive where you can use the active.
  5. Never use a foreign phrase, a scientific word or a jargon word if you can think of an everyday English equivalent.
  6. Break any of these rules sooner than say anything barbarous.

George Orwell, Politics and the English Language (Horizon, 1946) 

The rules that Orwell lays out create a solid foundation for the use of words, instead of the creation of stories. Indeed, even reading some of his work leads to the conclusion that corruption of the english language leads to corruption of ideas. Word choices matter regardless if the message conveyed is the same, and this principle is especially true for college essays where thousands of applicants compete for the attention span of weary admissions officers. Those who are able to convey what they mean in a concise, yet memorable way rise to the top.

Next, let’s examine Kurt Vonnegut’s 8 rules that lay a foundation on how to create a compelling story.

Kurt Vonnegut

Kurt Vonnegut

  1. Use the time of a total stranger in such a way that he or she will not feel the time was wasted.
  2. Give the reader at least one character he or she can root for.
  3. Every character should want something, even if it is only a glass of water.
  4. Every sentence must do one of two things — reveal character or advance the action.
  5. Start as close to the end as possible.
  6. Be a sadist. Now matter how sweet and innocent your leading characters, make awful things happen to them — in order that the reader may see what they are made of.
  7. Write to please just one person. If you open a window and make love to the world, so to speak, your story will get pneumonia.
  8. Give your readers as much information as possible as soon as possible. To heck with suspense. Readers should have such complete understanding of what is going on, where and why, that they could finish the story themselves, should cockroaches eat the last few pages.

Kurt Vonnegut: Bagombo Snuff Box: Uncollected Short Fiction (New York: G.P. Putnam’s Sons 1999)

While Kurt Vonnegut’s rules are intended for writing fiction, they are good guidelines for college essays. These rules obviously should be tailored to the essay you are writing, and some rules such as the 5th rule should be used with discretion dependent on your topic.

Students applying for college often make the fatal mistake of simply listing their resume in a 600 word format trying to convince admissions why they want to attend that particular college. Too often, students put together blocks of nonsense consisting of jargon such as “I desire to leverage my global network to…” or “I want to realize my potential as a future leader…”. Doing this is a one way ticket for your application to end up in the trash bin. You are more than just nonsense buzzwords — show admissions your personality and who you really are.

While the essay is based on your experiences or thoughts, it is in essence a compelling story as to why a college should want you. You need to convince the admissions officer that you are the perfect for that university, not the other way around.


For the essay writing process, you need to place yourselves in the admission officer’s shoes. If colleges wanted to simply put together the applicants with highest test scores, there would be no need to spend much money on an admissions office. Furthermore, reading through thousands of essays is a grueling task that no one wants to do, but is a necessary process because colleges want to create a class profile of diverse students. This can include diversity in interests, diversity in thought, diversity in background, or other ways that make you special.

It is extremely difficult to develop some sense of a candidate’s personality through just a list of achievements and awards. The essay, however, is the most candid way for the admissions officer to peer into your true thoughts. Even if you are a painting genius or world class marimba player, colleges want to know what kind of personality you may bring to the class profile. The beautiful part of college admissions is that it is holistic — every part of your profile is considered equally. In other words, a compelling essay can secure you a spot in the incoming class, even if you have a lacking GPA or SAT/ACT scores.