By Ben Feuer. Photo by Morgan Sherwood

Every year, a few students get into schools (and newspapers) by writing totally unconventional essays. Essays that break the mold, that reinvent the basics, and that often completely ignore the question asked and the school’s requirements. But, hey, essays are an art form, and art is all about breaking the rules – right?

Sure. But there’s a smart way and a dumb way to take risks. And if you’re planning to be this year’s Ziad Ahmed and write that crazy, bare-your-soul tone poem in place of an essay, check out this advice first.

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SOME GROUND RULES

Don’t write a risky essay for a match or safety school – you’re better off simply taking your chances with a strong, compelling conventional essay and seeing how it goes.  You only write a risky, hail-mary essay for a reach school. 

You should always seek the approval and agreement of coaches, counselors and family members before embarking on a strategy.  Note that I didn’t say they have to approve of all your choices or your final draft – if you’re choosing to take a risk, do so by your own rules – but you should at least make sure you’re not missing something important or obvious before making a bold move. 

Make sure the ‘risky’ essay you’re writing is actually risky. A lot of the time, people think they’re being daring and original when they’re really just being derivative or obnoxious. Again, use your lifelines on the risky essay – not so people can tell you what to write, but so that you can gauge their honest reactions to what you have written.  And don’t copycat what got a lot of press last year. That’s the complete opposite of risky.

Don’t make your first-ever essay a risky essay. If you’re new to the essay writing game, start with some of the easier ones, and work your way up to the crazy ones.  That way, you’ll be sure of who you are as a candidate and what you have to offer before going off the deep end.

HOW DO I WRITE A RISKY ESSAY?

The whole point of risky essays is that they are cheeky, original and daring. So you should already have a pretty good idea of what you want to write about. If you don’t have a strong concept, why are you even considering a risky essay in the first place?

Now that you have your concept, make sure it aligns with all the other aspects of your candidacy. Consider Ziad Ahmed again (linked above) – he considered himself first and foremost a provocateur and activist, so his provocative, activism-themed ‘essay’ fit his candidacy to a T.  The purpose of an essay is to reveal who you are, to give the committee a strong sense of who they’re considering admitting. If you’re going to break the rules, you have to be giving them twice as strong of a sense.

Write your first draft quickly. Don’t slow down or give yourself too much time to second guess. Remember that a draft is just that, a draft. If it doesn’t work, chuck it and do something new instead. But trust your instincts. They’re what drove you to make this decision in the first place, so stick with them, and they’ll stick with you.

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Writing an essay, any essay, is hard, but writing a risky essay is four times harder. Like the best modern art, it may look simple, but the simple exterior conceals a lot of truth and authenticity (and hard thinking) beneath the surface. The risky essay is not for everyone – remember, for every one student who gets in this way, 1000 are getting in the old-fashioned way, by doing the work and answering the question asked. But if you’re a risk-taker, you’re not about playing the odds anyway, are you?