Like it or not, if you are applying to colleges from a wealthy part of New England, the admissions officer reading your essay is going to automatically assume that you have a silver spoon in your mouth. Our advice is to do everything you can to avoid furthering this stereotype.

First off, some don’ts. Don’t write an essay about some grandiose project that could be misinterpreted as a justification for why you think you are better than everyone else. Also, unless you’ve overcome some ridiculously difficult or traumatic obstacle, don’t write that essay either. There’s a kid out there who swam to the United States from Cuba with missing limbs to escape certain death. His essay will make you look naive and sheltered in comparison.

Whatever you do, please oh please, don’t write about volunteer work or a sport you play. Colleges get these types of essays so often that admissions officers eyes glaze right over if they even see the word mission or soccer. Your chance at grabbing their attention with one of these essays is basically zero.

So what should you write about then? The college application essay should be two things: humble and creative. It should differentiate you from the thousands of other candidates that your prospective college is considering. It should be an essay that your parents tell you is not “impressive” enough. It should be playful without being flippant. It should be insightful without being preachy. And (here comes the big cliché) it should say something about you that can’t be found anywhere else on your application.

An exercise that I find helpful is to have students take ten minutes to list anything – absolutely anything – that they find interesting. It can be how they arrange shoes in their closet, why they find traffic lights interesting, how they decide on a nail polish color, the plot of a movie they recently watched, or about the time that they locked themselves out of the house. One thing that never ceases to amaze me is how good teenagers are at making lists under timed conditions.

Once they have completed the list, I ask students to go through the various items and try to find strands that connect the different items:

Red traffic lights remind me of the time I locked myself out of the house.

I wonder who was in charge of picking out the shoes for the actors in Birdman?

Whenever I lose my mom in the grocery store, we meet in the kitty litter section.

The idea is to break through the typical stagnation and get the creative juices flowing. Otherwise, students generally get locked into the typical “I helped build a house in Costa Rica” or “being the class president taught me a lot about leadership” mindset. (Ugh and double ugh. Do you want to read either of those essays? The answer is no. No, you do not.)

I’ll generally ask a lot of questions about the items on the lists and sooner or later we’ll generally hit on something that (a) is interesting and (b) the kid is passionate about. Believe it or not, teenagers are passionate about some really interesting topics. Sometimes it just takes a little bit of exploration to find out what those topics are. I swear, sometimes kids even surprise themselves.

Some of the best essays incorporate two of the ideas from the list into a single piece. Perhaps there’s only a tiny connection between the two ideas at the beginning of the essay, but the connection becomes more clear as the essay progresses. By the time the reader arrives at the conclusion everything has been tied together beautifully.

The exact level of creative comfort varies from student to student, but once a student finds something that they are passionate about, they’ll generally take the ball and run with it. The most important thing is to break out of the cookie cutter college application essay mindset.

There’s always someone who had it tougher than you. So let them write that essay. There’s always someone who is more impressive than you. So let them make a fuss about themselves. What should you do when you can’t win?

Change the rules of the game.