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Business School Application Failure Essays Series – Part II: Experienced Failure

May 08, 2019 :: Alex Collazo

[Don’t forget to dig into Part I of this series! Wahoo!]

Dartmouth Tuck used to ask applicants to “tell us about a time you: received tough feedback, experienced failure, or disappointed yourself or others. How did you respond, and what did you learn about yourself as a result?”

The multi-part question is a lot to bite off, but the idea behind each of these sub-topics is the same: how do you handle failure? Do you give up, do you blame others, or do you take responsibility and improve? This topic is absolutely worth taking the time to think through, because it contains basically every version of the “failure story” question all in one prompt. If this type of question doesn’t come up on any of your application essays, it almost certainly WILL come up in the interview, and folks, this one is a biggie.

Think of this as a drill you run in football practice. The exercise may seem like it has nothing to do with the game, but when you’re at the season playoffs and you complete the game-winning pass you’ll realize all that prep you did WAS relevant: you were building muscle memory. In this series, we’ll break down this question and address each piece, building that muscle memory so that when you come across a “failure” question either in an essay or in an interview, you can make like Tom Brady and bring home the ring. Here, we dig into Part II.

PART II: Tell us about a time you…experienced failure.

This is the quintessential failure essay. Just as in the first option, the key here is to OWN it. Applicants who describe a failure while trying to avoid owning up to the mistake, weakness, or knowledge gap that LED to that failure are shooting themselves in the foot, while applicants who ADMIT to the failure and take responsibility are striking gold.

First things first, you need to bring the reader into your thought process, your mindset, your M.O. BEFORE you bombed. You were certain that XYZ steps were the way to go, you were positive you were on the right path, and sure of success. Drop the reader into the story there, and only once you’ve convinced us of that line of thinking can you begin to show us where it all went sideways. Less than halfway into the essay we should have gone from “everything’s going swimmingly and I know exactly what I’m doing,” to “this is an unmitigated disaster!”

The next step is the most vital aspect of this essay: As you tell us how it all came tumbling down around you, make sure you identify where and how YOU were at fault. This is that “ownership” piece, and shows the adcom that you can honestly self-reflect—the key to being able to improve and grow. This is difficult for two reasons. Firstly, you need to be confident enough to be completely vulnerable. As we often discuss, this is simply a matter of knowing that admitting to failure and weakness will actually STRENGTHEN your app, while trying to hide it or justify it will WEAKEN it.

Recommended Reading: How to Nail the MBA “Impact Essays”

The second reason this can be difficult is much more practical: sometimes it is simply difficult to know why exactly things went wrong. This is where a little reflection will go a long way, and taking the time to do this NOW, before you write this essay or hear this question in an interview, will serve you well. The key to figuring this out is to “un-know” what you learned as a result of this failure; take yourself back to the decision or set of decisions that led to your failure and remind yourself of what you DIDN’T know back then. This would be like showing us charts and graphs from just before the 2008 crisis and selling us on the idea that NOTHING was wrong, and there’s absolutely no way that a housing bubble is imminent.

Once you’ve convinced yourself (and us) of this logic, go back in time again, but this time bring the sports almanac with you. Suddenly, you’ll see all the ways in which you were dead wrong. You’ll end up with as clear a sense of what caused the failure, and how you were responsible, as you could hope for. This should help clarify what you LEARNED as a result of that failure, and how you grew from it. And that, folks, is the key to the failure essay in a nutshell.

Truly successful people have learned to think this way reflexively. The really successful CEOs, game-changers, and badass innovators have learned that rather than erase the stain of their previous misguided thinking, they need to remember EXACTLY how and why they shanked it the first (or first hundred) times. That’s the kind of thought process you should emulate in this essay.


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