UChicago Questions

美国芝加哥大学 , my alma mater, is known for non-standard supplementary college admission essay questions. WSJ published an article on this, and if you have a subscriber, you can see the divisiveness reactions from parents and readers. I confess that it wasn't easy for me. I remember this18-year self asking after looking at questions then:" What? Are you serious? How am I supposed to write about this?!"

It turned out that the admissions essay writing process itself was an important education. It forced me to think and think really hard. I remember thinking without coming up with anything for days. Needless to say, I was frustrated. A few days before the application due date, I wrote both essays in the middle of the night. My mom was my proofreader and got busy in the morning. One essay was about being a packrat reflecting on my childhood experience living in different countries and moving from school to school. Another essay was about a picture shown on the back of the UChicago brochure. The black and white picture showed the feet of the person who was sitting on a stone bench on campus. I wrote about what that person might be pondering and if I was sitting there, what I would be thinking about.

I believe that more important than the essay questions is the willingness and ability to go through this process and engage and confront with questions that look different and do not have standard and cookie-cutter answers. These questions force our brains to step outside the universe that is the most familiar to us. These questions asked our brains to embrace the uncomfortable and the unexpected.

How does the above relate to investing and entrepreneurship?

Having a good startup idea is only one part of the success. Other part is execution. Evaluating startup idea is easy after seeing thousands of them. Evaluating execution is extremely hard because I am evaluating people who will be implementing the idea. One way I use to evaluate CEOs and senior executives is asking questions that I believe that other investors do not ask. Many founders and management team want to understand what I think the right answer is and give me that answer. That is not what I am looking for. Rather, I am trying to see how they embrace the unexpected, the uncomfortable, and the challenging questions. I want to see how they answer with some logic, openness, humbleness, and confidence. I want to learn how they think.

No AI and Deep Tech readings this week. I leave you with some admissions essay questions from the University of Chicago. Enjoy! Some of these are good ice breakers too if you feel adventurous. Have a great week ahead!

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Was it a cat I saw? Yo-no-na-ka, ho-ka-ho-ka na-no-yo (Japanese for “the world is a warm place”). Mo?e jutro ta dama da tortu je?om (Polish for “maybe tomorrow that lady will give a cake to the hedgehogs”). Share a palindrome in any language, and give it a backstory. Inspired by Leah_Beach, Class of 2026, Lib Gray SB ’12, and Agnes Mazur AB ‘09

What advice would a wisdom tooth have? Inspired by Melody Dias, Class of 2025

You are on an expedition to found a colony on Mars, when from a nearby crater, a group of Martians suddenly emerges. They seem eager to communicate, but they're the impatient kind and demand you represent the human race in one song, image, memory, proof, or other idea. What do you share with them to show that humanity is worth their time? Inspired by Alexander Hastings, Class of 2023, and Olivia Okun-Dubitsky, Class of 2026

UChicago has been affiliated with over 90 Nobel laureates. But, why should economics, physics, and peace get all the glory? You are tasked with creating a new category for the Nobel Prize. Explain what it would be, why you chose your specific category, and the criteria necessary to achieve this accomplishment. Inspired by Isabel Alvarez, Class of 2026

Genghis Khan with an F1 racecar. George Washington with a SuperSoaker. Emperor Nero with a toaster. Leonardo da Vinci with a Furby. If you could give any historical figure any piece of technology, who and what would it be, and why do you think they’d work so well together? Inspired by Braden Hajer, Class of 2025

What can actually be divided by zero? Inspired by Mai Vu, Class of 2024

Subway maps, evolutionary trees, Lewis diagrams. Each of these schematics tells the relationships and stories of their component parts. Reimagine a map, diagram, or chart. If your work is largely or exclusively visual, please include a cartographer's key of at least 300 words to help us best understand your creation. Inspired by Maximilian Site, Class of 2020

"Do you feel lucky? Well, do ya, punk?" - Eleanor Roosevelt. Misattribute a famous quote and explore the implications of doing so. Inspired by Chris Davey, AB’13

Joan of Arkansas. Queen Elizabeth Cady Stanton. Babe Ruth Bader Ginsburg. Mash up a historical figure with a new time period, environment, location, or occupation, and tell us their story. Inspired by Drew Donaldson, AB’16

What’s so odd about odd numbers? Inspired by Mario Rosasco, AB’09

How are apples and oranges supposed to be compared? Possible answers involve, but are not limited to, statistics, chemistry, physics, linguistics, and philosophy. Inspired by Florence Chan, AB’15

“A man cannot be too careful in the choice of his enemies.” –Oscar Wilde. Othello and Iago. Dorothy and the Wicked Witch. Autobots and Decepticons. History and art are full of heroes and their enemies. Tell us about the relationship between you and your arch-nemesis (either real or imagined). Inspired by Martin Krzywy, AB’16

Dog and Cat. Coffee and Tea. Great Gatsby and Catcher in the Rye. Everyone knows there are two types of people in the world. What are they? Inspired by an anonymous?alumna, AB'06