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At some point, most college-bound students are tasked with writing an overcoming challenges essay. The prompt crops up in various forms, as a supplemental short essay about overcoming a challenge, and in as the main essay itself.

Some students may feel inclined to write about a dramatic experience (say, spotting a grizzly bear outside the kitchen window), mistaking the drama of the moment for a significant challenge. Others may get to work, only to realize they don’t have much to say about the time they got a C in P.E. (that dreaded frisbee unit). Students who’ve overcome unspeakable difficulties, like a death in the family, may find that reducing the tragedy to 650 words feels insufficient, or worse—as if they’re attempting to profit from suffering. One or two students may stare down the blank computer screen as their entire existence shrinks to the size of a 12-point font. Should they write about the challenge of writing about the challenge of writing an overcoming challenges essay??

Don’t worry. Focusing first on how to tackle the essay will help any student decide what they should write about. In fact, how the essay is written will also prove more influential than the challenge itself in determining the strength of the essay.

Decoding the Prompt

Let’s take a look at the overcoming challenges essay question included among the seven 2023-24 Common App Essay Prompts:

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?

Notice how the prompt places an immediate emphasis on the “lessons we take,” rather than on the obstacles themselves, or any potential success. This is because the challenge itself often says less about the student than the way the student chose to tackle it, or the way they now reflect on it. In other words, obstacles often come at us randomly; it’s our personal response to the circumstances which reveals something of who we are.

While studying a prompt for clues, it’s helpful to think from the perspective of the admissions officer (the essay reader). What can they glean from an overcoming challenges essay?  A lot, actually. A thoughtfully written essay may tell them about the student’s personality, as well as things like problem-solving techniques, rigor, persistence, creativity, and courage. These insights can work to prove to the admissions officers that the student has what it takes to overcome challenges in college, too. These future challenges may range from the inevitable academic obstacles that occur with heavy courseloads, to that arise as college students form their adult identities.

Picking Your Topic: A Brainstorming Activity

With the question of identity in mind, let’s now approach the overcoming challenges essay backwards, by brainstorming the final message the student wants it to contain.

For this three-part exercise, the student will first set a five-minute timer. With the clock ticking, they’ll jot down character traits, values, and any descriptive words or terms that say something about who they are. If stumped, change perspective. The student may imagine what their best friends, parents, coaches and siblings would say. (For example, tenacious, logical, scientific, peacemaker.) Even mild criticism can be helpful, as long as it’s not cruel. While a student’s brother may call him a “perfectionist,” perhaps this word will trigger other relevant words, like persistent and detail-oriented.

Next, the student will set the timer for another five minutes, pull out a second sheet of paper, and jot down any challenges, obstacles, setbacks, failures, and achievements that come to mind. Don’t hold back here or overanalyze. (For example: underdog at state swim meet, getting lost on the family hike, petitioning for a school compost system…)

Lastly, the student will place the two pages side by side, and draw lines between the items on the list wherever connections occur. One student may draw lines between persistent, curious, gamer, passionate about electronics, and saved the day during the power outage. Another set of lines might connect caring, observant, creative thinker, and helped sister leave abusive cult. Whatever ideas are sparked here, the goal is to identify which challenges will demonstrate something essential about the student to an admissions officer.

Topics to Avoid

The internet is rife with advice on what not to write when writing an overcoming challenges essay. Yet this advice can be confusing, or downright hypocritical. For instance, some may advise against writing about death. Yet a student who lost their father at an early age may be capable of writing a poignant essay about their search for an alternative father figure, and how they found one in their soccer coach.

I suggest avoiding guides on what not to write until after the student has done a thorough round of brainstorming. Otherwise, they risk censoring themselves too early, and may reject a promising idea. Once they’ve narrowed down their list to three ideas or less, they may want to check our guide on College Application Essay Topics to Avoid.

The reason why certain types of overcoming challenges essays miss the mark is that they emphasize the wrong aspect of the experience, which turns the topic into a cliché. While it’s generally a good idea to avoid trivial topics (again, that C in P.E.), any topic has the potential to be compelling, if it’s animated through personal opinions, insight, and description. Details bring an experience to life. Structure and reflection make an essay convincing. In other words, how the story is told will determine whether or not the topic is worth writing about.

So, rather than avoid specific topics, consider avoiding these scenarios: if you can’t show the essay to your best friend or grandmother, it’s probably not ready to show a college admissions officer. If you must write a clichéd topic, don’t choose a typical structure.

Techniques to Hone

Techniques that animate an overcoming challenges essay are the same ones used in storytelling. Think setting, visuals, sounds, dialogue, physical sensations, and feelings. “Showing” instead of “telling.” Crafting the essay with these inner and external details will bring the challenge to life, and catch the reader’s attention.

Another technique which works well when trying to avoid the trappings of cliché involve subverting the reader’s expectations. In storytelling terms, this is a plot twist. The student who got a C in P.E. may actually have a stellar essay on their hands, if they can break away from the “bad grade” trope (working harder to improve their grade). Perhaps this student’s story is actually about how, while sitting on the bleachers and not participating in the game, they found themselves watching the frisbee spin through the air, and realized they had a deep interest in the movement of astronomical bodies.

Some of the strongest overcoming challenges essays demonstrate what students have learned about themselves, rather than what they’ve learned about the obstacle they confronted. These essays may show how the student has come to see themselves differently, or how they’ve decided to change, thanks to the challenge they faced. These essays work because the reflection is natural and even profound, based on the student’s self-awareness.

Writing the Overcoming Challenges Essay, or Drafts, Drafts, Drafts

Everyone writes differently, some by outlining (never a bad idea), some by free-styling (good for capturing sensations and memories), some by lighting a candle—but don’t procrastinate too much. The only “must” is to revise. After a first draft, the student should begin to look for several things:

1) Clarity and Detail. Is the challenge recounted with precision? Is it personal?

2) Structure. Consider mapping the structure, to visualize it better. Does the structure suit the story? Can it be changed for clarity, or to keep the reader more engaged?

3) Cliché. Identify words, sentences, and ideas that are dull or repetitive. Mark them up, and in the next draft, find ways to rewrite, subvert, condense, and delete.

4) Lesson Learned. Has the student reflected adequately on the lesson they learned from overcoming a challenge? To add more reflection, students might ask themselves what they have felt and thought about the experience since. Would they do something differently, if faced with the same challenge? Has their understanding of the experience evolved over time?

By the final draft, the experience and the reflection should feel equally weighted. To get there, it may take five or six drafts.

Overcoming Challenges Essay Sample

The Happiness Hotline

First there were reports. Then we were told to stop socializing, go inside, wait. Covid struck. Everyone knows what ensued. It probably looked different from where we were all (separately) standing, even though we faced the same thing. Those first weeks, I stood at my bedroom window. It was dark by early evening in Oregon. The weirdest part—after the fact that we were collectively sharing the loneliest experience of our lives—was the silence.

… it was really quiet.

So quiet, I could hear my mom sigh downstairs. (So quiet, I couldn’t remember if I’d hummed aloud, or if I’d just heard myself in my head.) When I looked out the window, I could hear the stoplight at the end of our street. Green to yellow. Click.

Before going on, you should know three things. First, this is not a Covid essay. This is about melancholy, and the “sadness that has taken on lightness,” to quote Italo Calvino. Second, from my bedroom window, I can see down a row of oak trees, past the hospital, to my friend Carlo’s house. Third, Carlo is a jazz singer. Maybe that sounds pretentious, a freshman kid being a jazz singer, but that’s Carlo, and I wouldn’t be me without Carlo being Carlo. He’s someone who appreciates the unhinged rhythm of a Charlie Parker tune. He’s an extrovert who can bring introverts like me out of my shell. He convinced me to learn trombone, and together we riff in the after-school jazz club.

In the first month of the pandemic, we called each other nightly to talk rap albums, school stuff. At Carlo’s house, he could hear a white-crowned sparrow. He could also hear his parents talking numbers behind the bathroom door. The death toll was mounting. The cost of living was going up too. As the month wore on, I began to hear something else in our calls, in the way Carlo paused, or forgot what he was saying. Carlo was scared. He felt sad, isolated, and without his bright energy, I too, felt utterly alone.

Overcoming Challenges Essay Sample (Continued)

After some dark days, I realized that to help ourselves we needed to help others. It was pretty obvious the more I thought about it. People are social creatures, supposedly, even introverts. Maybe our neighbors needed to remember the noisiness of life.

We built a happiness hotline. That sounds fancy, though essentially, we provided three-way calls on my parents’ landline. The harder part involved making flyers and putting them up around town, in places people were still going. Grocery stores, the post office. We made a TikTok account, and then—the phone rang. Our first caller.

For months, if you called in, you could talk to us about your days in lockdown. People went really deep about the meaning of life, and we had to learn on the spot how to respond. I’d become a journalist and a therapist before becoming a sophomore. After chatting, the caller would request a song, and if we knew how to play it, we would. If not, we improvised.

Now we’re seniors in high school. Carlo visits the hospital with band members. As for myself, I’ve been working on a community music book, compiling our callers’ favorite tunes. I don’t want to forget how important it felt to make these connections. Our callers taught me that loneliness is a bit like a virus, a bit like a song. Even when it stops it can come back to haunt you, as a new variant or an old refrain. Still, sadness can take on lightness when voices call through the dark: sparrows, friends, strangers. I learned I’m good at listening into the silence. Listening isn’t only a passive stance, but an open line of receiving.

Analysis of the Overcoming Challenges Essay Sample

This student uses their musical passion to infuse the essay with vivid detail. There’s a focus on sound throughout, from the bird to the stoplight. Then there are the callers, and the clever way the student conceived of breaking through the silence. The narrator’s voice sharpens the piece further, elevating a clichéd Covid essay to a personal story of self-discovery.

In fact, the essay briefly breaks with structure to tell the reader that this is not a Covid essay. Although techniques like this should be used sparingly, it works here by grabbing the reader’s attention. It also allows the student to organize their thoughts on the page, before moving the plot along.

Outwardly, the student is overcoming the challenge of loneliness in a time of quarantine. Yet there seems to be an inner, unspoken challenge as well, that of coming to terms with the student’s introverted personality. The essay’s reflection occurs in the final paragraph, making the essay experience-heavy. However, clues woven throughout point to the reflection that will come. Details like the Italo Calvino quote hint at the later understanding of how to alleviate loneliness. While some readers might prefer more development, the various themes are threaded throughout, which makes for a satisfying ending.

A Last Word on the Short Essay About Overcoming Challenges

The short essay about overcoming a challenge requires the same steps as a longer one. To write it, follow the same brainstorming activity, then focus more on condensing and summarizing the experience. Students who’ve already written a longer overcoming challenges essay can approach the short essay about overcoming a challenge by streamlining. Instead of deleting all the extra bits, keep two interesting details that will flavor the essay with something memorable and unique.