US universities offer supplementary essays as a way of enabling applicants to express why they like the university. The real reason they want to give you extra essay questions relates to the concept of the early decision round. They want you to “reveal your preferences” and show how seriously committed you are to the school.
If you write an essay to a college like Columbia about why you want to go to that school and you offer generic diatribes about New York, their core curriculum and the need for broad exploration, diverse classmates and other generic answers, they know you really haven't researched the school in detail. The really winning supplementary essays (which take a long time to write!) have to be so specific that what you can say literally ONLY apply to the single college you are applying to.
Some application essays are quite generic from school to school. They might ask you to describe the community you are from, for example. Unsurprisingly, high schoolers in the frenetic rush to apply to college, who have procrastinated writing application essays, try to copy/paste answers from school to school. This is the death cross! A university that can detect you are just answering with generic responses, and not customized to their university, knows that you are just spraying across multiple universities hoping one admits you. And let's be honest—they are usually right. For every one student I meet who genuinely loves a certain single university and is head over heels in love with it for a set of specific reasons, I would literally meet more than one hundred students who choose based on rankings a set of prestigious schools (and my previous arguments justify this as being rightfully so, in not all, but many cases).
University of Chicago wants to handbrake the spray-and-pray, copy/paste application essay strategy and force you to use your time to answer their truly cryptic prompts. I consider myself reasonably sharp holding several degrees in applied mathematics and have written academically in law school and doctoral programs but answering a question such as “what can actually be divided by zero” is very difficult. It is difficult by design. UChicago wants to force you to do a bunch of extra work that will only be relevant to their school. They do this so that they can shake off all the candidates who aren't that committed and who can't be bothered to write their complicated essays.
Between testing your willingness to “talk” through the difficult supplementary essays to testing your “action” through their binding admissions process, UChicago has mastered the game theory of admissions for a school that is highly prestigious but not considered in the upper echelons of competitive colleges. In doing so, they have shot up the rankings in recent years, artfully manipulating their yield rates and reading through the masses of college admits to find the kids who are really willing to commit. Good on them—but I hope for your sake that the other colleges don't copy UChicago!
You'll notice that nowhere does UChicago publish the specific acceptance rates by the stream of binding versus nonbinding. They never will (unless they are forced to under massive public pressure). This is intentional because they don't want you to actually think about this too deeply and try and game their attempt to game you. On their Class of 2024 admissions page4 for example, they list only that they accepted 2,511 students, enrolled 1,848 students, and had 34,372 applicants. This translates to a mind-blowing yield rate of 73.6%. This is only beaten by Harvard and Stanford with 81–82% yield rates. UChicago beats MIT, Princeton, Yale, UPenn, and Dartmouth on yield rate. Arguably, all of these other colleges are usually more desirable for applicants than UChicago, but through designing an application process that ruthlessly filters kids, they have been able to game their yield rate and shoot above their peer schools landing at an enviable US News ranking.5
I hope UChicago doesn't get too angry at me for revealing their strategy, but power to the student I say!
UChicago aside, what are the key learnings for you?
First, almost every student reading this should apply early decision. We all want to have a shot at applying to Harvard and Stanford, but I can tell you with absolute certainty that every year when I look at most applicants, they really have no realistic shot and shouldn't waste their breath applying. Giving up an early decision option to have a shot at applying early action to Harvard, Stanford, Yale, Princeton, or MIT is usually crazy. Most applicants cannot get into this tier of school but try anyway, and in doing so, end up getting to a far worse eventual university than the school they could have been admitted to if they had committed early decision.
If you miss the early decision opportunity, and then have to apply in the regular round, you will find yourself swimming in an ocean of talented kids who are all bombing out applications to eight-plus schools each. So unless you have a very strong profile, you'll be submerged by the competition.
Generally in life you should be optimistic, but when it comes to university early decision time, you need to swallow your pride and be pragmatic. Wipe your tears if your dream school is Harvard but your SAT score is 1490. It probably isn't happening. That is okay. Don't let your ego stop you from not committing early to one of the many brilliant choices that require a binding commitment and locking in your offer. This is an important critical decision. Make sure you ask an expert which college you can realistically get into in the early round.
Second, be a flighty lover and preach your love to everyone (bad advice in life but good for college admissions!). What am I talking about? In your supplementary essays you need to hit each school with crafted essays that highlight exactly why you love their school with super-specific examples that only apply to their university and no other. This makes it more credible that you actually sincerely love their university beyond all others, and that's why they are more likely to admit you, assuming that you will, in turn, take their hand when they offer it.
Let me give you an example. If you apply to Harvard, the crowd favorite, you can tell them that you love them because they are a high-ranking, prestigious university. You can tell them they have myriad classes to choose from, offer a wonderful liberal arts education and many extracurriculars like debating and Model UN that extend your passions. You can tell them you want to take advantage of unique research opportunities and meet inspiring, diverse classmates.
But that would be a terrible essay.
Go back and read that last paragraph. Scratch out Harvard and you could say the same thing about Yale or Princeton or any other reasonable university. That is the test you have to do. If a single sentence of your supplementary essay can apply to another university, try again—it probably isn't specific enough. I've sent more than 50 students to Harvard alone and any opportunity we have to showcase their specific interests in Harvard, we focus on communicating what Harvard, as a magnificent institution of learning, offers uniquely as Harvard.
Let's say you like economics, business, and finance (a good portion of applicants). What could you talk about when applying to Harvard?
You could mention Harvard Student Agencies, the world's largest student-run business organization that lets you as a freshman manage retail stores and get practical hands-on management experience.
You could talk about the unique Statistics with Quantitative Finance track. This was introduced in the last decade as the interest in students going into quantitative trading has grown enormously. Very few other universities offer anything like this.
It might be nice to mention the legendary Professor Blitzstein who teaches the wildly popular Statistics 110 who makes even the most abstract statistics concept fun and understandable with his thought experiments.
You might want to mention the Harvard i-Lab. This is an entrepreneurial launchpad that lets students launch their own company, find mentors, gives them an office space to work from, and opportunities to meet investors. It is a relatively well developed incubator compared to most colleges.
