Unless you have a really creative idea, pick one of the five set prompts.
Read through all the essay prompts before picking one.
You're applying to colleges, so you might think you should talk about yourself and your extra-curricular activities, like in a typical personal statement. It seems obvious, but be sure you're answering the essay question!
For example, if I were writing Essay Question #3, I would make sure I've answered all three parts of the question, so ultimately, the admissions officer would have an idea of what I think history is, who "they" are, and what "they" aren't telling us.
The strongest essays will tell a clear story or develop an argument with evidence.
The admissions officers will be learning about you by seeing how you construct this argument or how you incorporate characters and language to tell your story.You may not have thought of anything like these questions before, but that's okay!The UChicago supplements are a great chance for you to step back from the typical admissions process, think about something different, and express yourself creatively.Pick the essay topic that gets you the most excited to write, think, and creatively make an argument or tell a story.For example, I'm most excited about approaching Essay #1, because I love dissecting jokes and think I have some great starting ideas for it, so I would choose that prompt.You can even take a look at the course catalog to see what's currently being offered for undergraduates and graduates in every field.In your essay, highlight professors' work that excites you or specific classes you'd love to take (not "Intro to..." classes, but workshops like, "I-Thou and the Subject of Psychoanalysis").If any of these interest you, explain why you think UChicago's flag grants, for example, would help you get a head start on your future research and career goals. Because you're quirky, you love to learn, you spend way too much time falling through the rabbit hole that is Wikipedia, you want to learn Econ from the masters, you...Let your sincere feelings about the college shine through!For the UChicago supplement, you'll have to write two essays: one answering a quirky prompt and the second explaining why you want to go to UChicago. When you take a look at the uncommon essay questions, you should laugh.The essays are meant to be fun, creative, quirky, and thought-provoking.