UChicago Supplemental Essays: Any Tips?

I'm starting to draft my UChicago supplemental essays and finding them a little tricky. I've heard they look for creativity but I'm not sure to what extent. Does anyone have any advice on how to approach these essays? For reference, I'm aiming for something in the humanities.

Tackling UChicago's supplemental essays can indeed be a challenging but also an enjoyable endeavor. They're known for their unconventionally creative prompts that are meant to invoke thought-provoking responses. Here are a few steps that can guide you:

1. Choose Your Prompt Wisely: UChicago lets you choose from multiple prompts. Your choice itself can be revealing. Thus, select a prompt that speaks to you and that you believe you can answer honestly and intriguingly. You could also choose the "make your own prompt" option if you feel intrigued by this challenge.

2. Showcase Your Intellectual Curiosity: These essays are your chance to show what enthralls you and how your mind works. Show that you find joy in learning and thinking critically. If you're applying for something in the humanities, you might want to involve a literary or historical angle in your response.

3. Embrace Creativity: UChicago values imagination, so do not shy away from being original and even a little quirky. However, remember that your essay should still make sense and convey something significant about you. Be authentic. If humor comes naturally to you, feel free to use it. However, don't force it if it's not your usual style.

4. Be Specific: Avoid providing generic or cliche answers, and provide specific details and examples wherever you can. This not only substantiates your arguments but also adds depth to your essay.

5. Demonstrate Knowledge of UChicago: If possible, try to subtly tailor your response to fit the school. By demonstrating that you understand the university's academic environment, you make a stronger case for why you belong there.

For example, if you choose the question, "What can actually be divided by zero?" you could take a philosophical approach. You might talk about how dividing tangible items by zero is impossible, but dividing abstract constructs like time or emotions by zero leads to intangible yet intriguing outcomes. You can delve into how this ties into your explorations of existential thinkers, showing your ability to think logically while simultaneously expressing creativity and intellectual curiosity.

Finally, remember that while these essays might seem daunting, they're really just an opportunity for you to shine. Good luck!