Many boarding school applications include a question about setbacks or challenges. Students often struggle to find the right tone: perhaps they write about something that feels too trivial (e.g., 'the one time I got a B grade'), or perhaps they write about something overly dramatic or in a self-punishing way.
The goal is to write about something that was meaningful—insomuch as it resulted in a different perspective, or reframed an entrenched notion, or increased maturity / empathy / appreciation. "Failure" essays should leave Admissions Officers with a sense of a student's self-awareness, growth, and perspective.
In this article, I summarize four points I raised with my daughter: (1) failure essays are not actually about failure; (2) pick the right story; (3) show don't tell / avoid cliches; (4) avoid over-confessing.
Key Principle: Failure Essays Are Not Actually About Failure
Unless the event selected is wildly inappropriate, Admissions Officers won't care much about the event itself. They're evaluating:
- Honesty
- Resilience
- Teachability
- Maturity
- The ability to reflect on an experience
The narrative itself does not need to be tragic or materially eventful.
Picking the Right Story
Stories don't need to be cinematic or dramatic (in any case, stringent character limits preclude being able to get into too much detail). Some options to consider are:
- A team they didn't make
- A project that fell apart/went sideways—or even ended up fine, but was a disaster to get through
- A conflict they mishandled
- A moment of poor judgement
- A time they felt overwhelmed
My daughter wrote about her extreme introversion—as a challenge she largely overcame. In statements about her introversion, and where relevant, she also raised other adjacent struggles that she is aware of and continues to work on. From a more tactical perspective, a physical challenge my daughter wrote about was about a specific technique she's historically avoided in her sport because the technique is difficult and often results in physical discomfort. As part of this response, she wrote about a deliberate decision she made to work on applying the technique on a specific course, with the goal to become better by competition season. In these two examples (which she used differently across several prompts), the stories were personal and based on lived experiences (also meaning she found it easy to write about them).
Avoiding Clichés
Suffice to say, stay away from:
- Moral of the story-type endings (e.g., this taught me never to give up)
- Sweeping generalizations (e.g., I learned that hard work always pays off)
- Melodramatic framing (because it's distracting, and you'd be wasting characters)
Instead, focus on answering introspective questions like:
- What surprised you about how you reacted
- What did you learn about your habits or assumptions
- What would you do differently next time
- How have you applied/will you apply lessons learned in the future
- How did the outcome and/or your lesson(s) learned impact those around you
Strive for authenticity and specificity, and these features will naturally 'show' vs. 'tell' Admissions Officers about your maturity.
Avoiding Over-Confession / Self-Flagellation
Don't let the intrusive thoughts or negative feelings/language make their way into the response. Negativity may be inadvertent or deliberate; in either case, it's unnecessary.
I called this out a few times in my daughter's responses. And I understand it... she was writing honestly, and was using the tone and language that she has in her mind when recounting challenges. Putting aside self-esteem issues to work through, Admissions Officers neither need a front row seat into a student's deep insecurities, nor want to leave a response feeling uneasy or bad for students.
Students should neither wallow in or confess to every detail about mistakes. One easy-to-understand, simple example—paired with reflection—is enough. Failure/challenge essays work best when they reveal character, not guilt.