How To Write Your Common App Essay – Part 3 Of 8

This week, Noodle Pro Jamie Berger discusses Prompt 2 of the Common App essay, which he (affectionately) calls “the failure prompt”: The lessons we take from obstacles we encounter can be fundamental to later success. Recount a time when you faced a challenge, setback, or failure. How did it affect you, and what did you learn from the experience?

Jamie has been a test prep, writing, and academic coach for 32 years. He has a BA from Columbia University, an MA from City College of New York, and an MFA from University of Massachusetts, Amherst.


Every year, after working with my coachees to decide what aspect of themselves to focus on in the Common App essay – and yes, we brainstorm about what they want to tell colleges about themselves first – we take a look at the prompts, the framework for their self-reflection.

And every year, as much as I’m fond of the “challenge, setback, or failure” prompt, I’ve never worked with a student who decided to use it. Year in and year out, they see the word “failure” and think, “oh, no, I’m not falling for that trap!”

All our lives, we are taught to smile, give a firm handshake, and put our best foot forward; conversely, we are told – especially in making a first impression in everything from an interview to a date to an application – never to accentuate or even mention negatives. That’s why there’s the cliche/joke of someone in a job interview who, when asked, “What’s your biggest weakness?,” replies, “I just work too darn hard.” or “I care too much.” That is, their only negative is an *extreme* positive.

So, as much as I like the prompt, and the boldness it demands, I understand that students feel like it’s a lose-lose. Either they point out something “bad” about themselves, or they seem like they’re being fake by flipping the question around to point out how great they are. They pick another prompt and they write a great essay, and that’s fine.

I still hold out hope that someday a student will work with me on the “failure” prompt.

Who, in particular, might be wise to choose Common App prompt 2?

  • A student who had a rough freshman year for any number of reasons and has since improved every semester.
  • A student who had an injury or illness that interrupted a serious sport, dance, or other physical career and found another great outlet for their skills, interests, and genius!
  • A student who got in trouble somewhere along the line –  and for whom colleges will undoubtedly know about said trouble – who wants to address his or her misstep. (Warning: do NOT try this at home without consulting your college counselor!)

The Common App essay is the place where you show colleges something of who you are that they won’t see in your transcript or test scores. It’s where you show them your skill as a self-reflective writer; and where you show them your emotional intelligence, vulnerability, and path of growth into young adulthood. What better way to do all that than to step up and address a challenge, setback, or, yes, FAILURE? Go ahead and write a draft of it. Even if you decide not to use it, it will probably still inform your essay.

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