Where’s Waldo

Tips for Tackling Wacky College Essay Prompts

  • How do you feel about Wednesday? (U Chicago)
  • What’s broken, and how do you fix it? (Notre Dame)
  • Our campus is powered by wind turbines. What empowers you? (Carleton)

Colleges are requiring more out-of-the-box essays than ever to gauge not only candidates’ writing but their wit and creativity as well. That’s because admissions officers buried in SAT scores and activity lists and transcripts enjoy the three-dimensional, wild-card feel to these open-ended questions. Explains Villanova: “Your essay provides a view into your thoughts, opinions, hopes and dreams.”

  • Celebrate your nerdy side (Tufts)
  • Write an essay somehow inspired by a super-huge mustard (U Chicago, again…)
  • Give us your top ten list (Wake Forest: Note there is no hint as to what top ten list – Movies? Pizza? Presidents? Second baseman? One student chose her “Top Ten Crayola Crayon Colors.”)

So faced with such crazy prompts, what’s a busy senior to do? Let me offer three tips to tackle these creative supplements:

  1. Brainstorm through Freewriting: Here’s a technique I imported from the Creative Writing classes I used to teach. Let your inhibitions go and write down whatever comes to your mind relative to the topic as quickly as you can for three straight minutes. Leave punctuation and spelling to the side. Just write, freely. No stopping. Then come up for air and you’ll always find a few nuggets to copy, paste and run with.
  2. Trust your Voice: These essays offer you the chance to “show your voice” – that is, your particular narrative style. The same way your choice of phone cover or laptop stickers or playlist shows your style. So an authentic, conversational tone fits the bill here. (That said, do be sure to proofread your final draft!) U Chicago demystifies the challenge this way: “We want you to use this as a time to be creative, to take a prompt and run with it in the way that you think represents what’s going on in your brain best.”
  3. Mix up the Medium: Change it up and try writing on a tablet, or your phone. Or just change up the font on your computer: Comic and Gothic fonts can elicit a different tone than Times and Cambria. Or here’s a crazier idea: do a free write with actual pencil and paper! A slight change in medium can cast a new light on your writing as you free yourself from the order of the 5-paragraph essay and let it go and discover a more colloquial voice.

I hope these tips arm you to take on these supplements with more confidence. To finish up my blog, I must defer again to one more U Chicago prompt as the closing credit:

So where is Waldo, really?


A couple of admissions seasons ago, a NY Times reporter quizzed me on supplements, so check out more.

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