Chicago Booth Essay Breakdown – Essay 2 (2009)

Describe a time when you wish you could have retracted something you said or did. When did you realize your mistake and how did you handle the situation? (500-750 words)

We have all experienced this. The “OH NO” moment. Woulda, shoulda, coulda.

There are tons of ways to skin this sucker. But let’s analyze the words in the question a bit. “A time when you WISH you COULD HAVE RETRACTED something you said or did.”

This isn’t as simple and straightforward as “tell us about a mistake.” Very easy to slip into thinking about it that way. But the words are carefully chosen here.

It all comes down to REGRET.

Yes we’ve underperformed, yes we’ve failed at stuff, yes we’ve said or done things we shouldn’t have—-> but there are a special few instances where we wish we could rub the lamp, and beg the genie to take us back in time and ERASE it from ever happening. And it has to do with regret. And guilt.

• We knew the correct decision, but were pressured to do something ELSE

• We hurt someone’s feelings, and it stayed with us; proving to be somehow more profound than whatever good came at its expense

• We tried to repair a mistake with a band-aid, and the mistake kept compounding, and at some point we just wish we could go back and own up to the mistake at an earlier point in time

The secret sauce here is regret. And it’s different from getting a B+ as opposed to an A. It’s different from being confident about making a call and simply being wrong. Sometimes your process may be pristine, but the outcome just doesn’t work out. That’s not what we’re after.

We’re after the thing that caused you to look at yourself in the mirror and for a brief moment, NOT FEEL PROUD. “I should have known better.” This will lead you to a thing you did or said to someone that will answer this question nicely. Now, structurally, we’ve seen this with other questions similar in nature—-> do not get ahead of yourself. In other words, don’t introduce it (there are always exceptions) knowing what you did wrong at the outset.

It will be more effective to walk us through the “situation” while it was happening, and possibly to convey the dilemma you may have experienced at that time. Sometimes there will be no dilemma and you’ll recognize the error well afterwards. That’s okay too, in that case walk us through the thing you said or did as though it made perfect sense given the circumstances.

THEN reveal what went wrong, and WHY YOU FELT BAD ABOUT IT. This is crucial. There is a human component here. Your confidence was shaken, your sense of morality was punctured… something happened that made you feel bad. Let’s dig into that.

Finally, walk us through how you acted on that cognitive dissonance. How did you turn that negative energy into POSITIVE energy to right the wrong?

This is LIKE your typical mistake essay, but it seeks a slightly more honest admission of personal regret. Identify the best example of THAT before crafting this sucker.

Why Stanford, Why Tuck, Why Wharton, etc.