How to Write Effectively About Your Challenges

Ryan Kelly

“Tell us about a personal challenge you’ve faced and how you overcame it.”

This is one of the most common questions asked in admissions essays, and it also comes up frequently in interviews–whether for a job or a seat in an incoming class.

It’s not easy to answer, especially because students get caught up in worries about whether their challenges are “good enough” to discuss versus other applicants.

I advise them not to play the comparison game because there is always going to be someone out there who has walked a more difficult path than you. The goal is to be thoughtful about the challenge you select, and then pour everything you can into telling your own compelling story.

The first step is brainstorming and coming up with ideas:


  • Which of your activities had the most setbacks or failures? Can you recall one or two specific moments that required your resilience?

  • Which of your activities presented the steepest learning curves? Why were they so challenging? Did you have to change something about yourself to succeed?

  • Did any of your activities expose you to people much different than yourself? Were there difficulties in communicating and collaborating with them?

You can probably see a trend - we’re looking for moments of suffering, moments of hardship and doubt, moments of conflict and tension.

Why? Because those moments are the ones that cause the most personal growth. They’re also the moments that will illustrate your best qualities and show that you can overcome obstacles. In essence, you’re trying to convey a before-and-after picture of you based on the experience.


You need to recognize the genres you’re writing in, so that your challenge essays don’t sound like everyone else who’s writing about the same types of experiences.

Let’s cover some of the common genres and their cliches:


These essays often start with candidates entrenched in the lab, hunkered over some kind of complex experiment or equipment. It’s often hard to distinguish what’s actually happening in layman’s terms. There’s often a list of jargony phrases and techniques that were mastered over time, followed by a takeaway about analytical skills, attention to detail, and problem solving.


These essays often start with some line about being “met with blank stares” from student(s). Then they discuss some concept/lesson that went poorly and the steps the candidates took to improve their communication. They typically end on the reward of “finally helping the student(s) make a connection.”


The worst essays of this genre start with some meeting, like an executive board, and then catalog the various obligations and responsibilities that had to be balanced. Ironically, these leadership essays are devoid of characters and dynamic team situations. The narratives often get bogged down in boring administrative details, just like the activities themselves.  


These essays often start with an introduction to some patients and/or families in the hospital, with a description of their injuries or symptoms. The candidates might comfort them, listen, and/or offer them a warm blanket. The essays end with takeaways about the power of compassion and doing anything within their limited power to help someone.

If possible, try to deviate from these themes and cliches. For example, think about what makes your leadership experience unusual or memorable - maybe you had to run an event while suffering from a stomach flu, or maybe you had to lead people who were much older than you?

But if the cliche examples sound all too familiar, don’t fret. The real reason things come off as cliche is because they lack specificity and memorable details. Even if you fall into the conventions of a genre, you can still make the essay unique through your voice and storytelling.


If you like numbers, I’d say a challenge essay is about 70% storytelling, 30% reflection. The examples and concrete details are the key to convincing your reader of your personal growth and the activity’s significance. It’s not enough to just say it.  

Often with such limited space, it’s best to focus on one powerful story that best exemplifies the activity overall. If you cover everything, the different parts will be diluted of their power.

It’s important to remember that you often have a separate chance in your application to describe the activity’s responsibilities, tasks, noteworthy accomplishments, etc. So when you write the challenge essay, just dive right into your narrative. The readers will already have plenty of context, so don’t bother anchoring them with tons of factual information.

You’ll need to be economical with your words/characters, so consider your story’s function and intentions before writing. Let’s break down an example to see how a most meaningful works:




The hook uses imagery or lively language to draw you into the setting and story, while also quickly introducing the major conflict.

Broken exit signs. Smashed ceiling tiles. Bulletin boards smeared in lewd graffiti. Not exactly a wholesome environment for a dormitory.

I was a new sophomore RA, and ResLife expected me to monitor a rowdy bunch of junior football players in Murphy Hall.


The plot focuses on the most pivotal actions, conversations, or events, and then explains their consequences and resolution.

When I covered the floor rules, the guys laughed and rolled their eyes while tossing a ball around. Most were on the cusp of legal drinking age and took advantage of that grey area. As I addressed noise complaints, I struggled to gain cooperation from manchildren who viewed me as a mascot. Things turned sour when I wrote up their teammate while on duty. I felt like I was living with a crew of strangers, or worse, enemies.

But I finally earned their respect when I escorted one of them to the hospital after a near overdose. I coached him through the unpleasant process of drinking liquid charcoal, and he assured the team that I had their backs. Later, a few of them helped me fix the ceiling and confronted the floormate who vandalized my flyers.


The reflection covers the most important lessons and takeaways, explaining how the experience has shaped / will shape your actions and perspective.

In the future, I will need to gain people’s trust--whether patients, families, or colleagues. Some will be doubtful, confused, or angry, potentially viewing me as a threat or outsider. As an RA, I learned the importance of showing consistent and genuine concern as a way to break down barriers and forge relationships.  

Why does this example succeed?

  • The readers receive a vivid, concrete glimpse into the experience; they can clearly see the conflicts and happenings of the plot.
  • There’s a clear resolution that illustrates the candidate’s impact on the people and situation.
  • The chosen story exemplifies the overall challenges and rewards of the experience in the bigger picture.
  • The reflection clearly explains why the lessons of the experience were crucial for the candidate’s development, and why they’ll be useful moving forward.

All that in only 1318 characters! You see? It’s possible!

Don’t expect to achieve the perfect balance between showing and telling right away. Like any other writing, a challenge essay requires several messy iterations before it will look and feel polished like our example above.

But if you follow my steps, I guarantee things will be less messy for you.

Finally - don’t underestimate the power of these essays. They’re not merely elaborations on the activities; they’re important narratives that help set the tone for your application.

If done well, they’ll help to create a great first impression, provide key insights into your character, and make you much more memorable to admissions committees.

Best of luck!

- Ryan

For over 11 years, Ryan Kelly has guided hundreds of students towards acceptance into top colleges and graduate schools, with an emphasis on standing out while also staying true to themselves. Read more about Ryan here. Or book a free intro meeting with him here.