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How to Write the Overcoming Challenges Essay + Example

April 17, 2023

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 social and moral challenges 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.

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Kaylen Baker

With a BA in Literary Studies from Middlebury College, an MFA in Fiction from Columbia University, and a Master’s in Translation from Université Paris 8 Vincennes-Saint-Denis, Kaylen has been working with students on their writing for over five years. Previously, Kaylen taught a fiction course for high school students as part of Columbia Artists/Teachers, and served as an English Language Assistant for the French National Department of Education. Kaylen is an experienced writer/translator whose work has been featured in Los Angeles Review, Hybrid, San Francisco Bay Guardian, France Today, and Honolulu Weekly, among others.

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How To Level Up Your Overcoming Challenges Essay

This article was written based on the information and opinions presented by Robert Crystal and Kaila Barber in a CollegeVine livestream. You can watch the full livestream for more info.

What’s Covered:

Components of a challenge-based essay, how to structure your essay, challenge-based essay tips.

In this article, we cover ways that you can revise challenge-based personal statements to help highlight your own skills, values, interests, and qualities.

For students who have faced challenges, writing a challenge-based personal statement could be a good option. The challenge-based essay is made up of three main pieces: challenges and effects, steps you took to overcome your challenge, and what you learned.

Clear and Compelling Challenges and Effects

When writing a challenge-based essay, the first step is to make sure that you write about the challenge and its effects clearly and compellingly. You want to avoid leaving any room for interpretation from the reader by simply and concisely outlining your challenges.

Keeping your challenge concise will allow you to show your reader what you went through and how it impacted you, while also leaving space for you to show what you did and what you learned.

For example, if in your essay you mention that you struggled with your mental health, but you don’t provide any other details, the reader will either make their own assumptions about your experience, or they could just skim through your essay without making any assumptions at all. To avoid the challenge of being misinterpreted, it is important for you to be specific about what you have faced.

Steps You Took To Overcome Your Challenge

The next step in a challenge-based essay is to make sure that you’ve elaborated on what you did to overcome your challenge. While your challenge is important, the admissions officer is more curious about what you did to overcome your challenge and the steps that you took to make your situation better. 

What You Learned

The last part of a challenge based-essay is a section in which you elaborate on what you learned. Here, you should build upon what you did to overcome your challenge by including what you learned from overcoming it. This is your teaching moment to show that you reflect and learn from your experiences and environment.

As you write, keep in mind that each component should make up about one-third of your essay. This is important because it is common for students to focus mainly on what the challenge is and write 45% to 50% of the essay talking about the challenge and its impact. 

Instead, you should split your essay into thirds, with challenges and effects, what you did, and what you learned each taking up approximately one-third of your total word count. Approaching your essay in this way provides you with two-thirds of the essay to show your values and personal growth. 

There are several handy tips that can help you write a challenge-based essay like this. These tips include, in addition to writing clearly and concisely to build a compelling narrative, using active verbs, including your insights, and connecting everything back to your values.

Use Active Verbs

When talking about what you did to overcome the challenge, it is important to use active verbs. Examples of active verbs include words like customized, designed, facilitated, recruited, and restructured. Active verbs clearly and specifically show the reader what you did, and these are most crucial to include when you write about the steps you took to overcome an obstacle.

Include a Strong Insight and Connect to Your Values

During the “what you learned” section, make sure that the insights that you include are strong. Strong insights demonstrate to the reader how you’ve made meaning from the challenge that you’ve faced, and are an opportunity for you to showcase your values, self-awareness and critical thinking.

This essay should be written in a way that makes your core values clear to the reader. One exercise that you can do to help find connections and linkages to your core values is to consider guiding questions like the following: 

• What did you do as a result of your challenge? 
• What moment did something change for you? 
• Did you take responsibility for anything you hadn’t before? 
• Did you start paying for things? 
• Did you learn a new piece of technology? 
• Did you help someone or did someone help you?

As you write and revise, you can use these guiding questions, and questions like them, to reflect and become more aware of your own core values. You may find that once you clarify and include more of your own values, your insights are strengthened.

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I need some help brainstorming for my college essay. I'm thinking about writing a narrative about overcoming a significant challenge in my life. Can you share any tips or examples to help me get started?

Sure, I'd be happy to help you brainstorm for your college essay. Writing about overcoming challenges can make for an engaging and compelling narrative, as it shows your resilience, growth, and/or problem-solving skills. Here are a few tips and examples to help you get started:

1. Reflect on your life and identify a few challenges that you've faced. They can be academic, personal, or extracurricular in nature. Some examples might include dealing with a health issue, working through a family conflict, or overcoming a fear.

2. Choose one challenge that had a significant impact on your life, and focus on the process you went through to overcome it. Be specific about the steps you took and the feelings you experienced during this process. This will help you create an engaging story that demonstrates your personal growth.

3. Show, don't tell. Use descriptive language and vivid details to paint a picture of the challenge and how you overcame it. This will help your reader connect with your experiences and emotions.

4. Consider the impact that overcoming the challenge had on your life. Did it teach you a valuable lesson, change your perspective, or shape your character? Be sure to link this growth to your future goals or ambitions, showing how your experiences will contribute to your success in college and beyond.

For instance, let's say you faced a challenge with financial hardship which affected your ability to participate in extracurricular activities. Instead of giving up, you came up with innovative ways to continue pursuing your interests: by becoming actively involved in affordable or free community programs, connecting with like-minded individuals online, and building your own projects. In this essay, you could discuss your determination and resourcefulness, how these experiences enriched your life, and how they influenced your desire to give back to your community in college and beyond.

Another example could be about overcoming a language barrier after moving to a new country. The essay could revolve around your struggles with the language, the help you received from teachers and peers, and the various strategies you employed to improve your language skills. You could then discuss the sense of accomplishment and confidence you gained, and how those qualities would enable you to actively engage in diverse communities and enrich the campus life during your college years.

Remember to keep your essay focused on your experiences and the lessons learned, rather than writing about the challenge itself. This will ensure that your essay is engaging, personal, and relevant to the goals and values of the colleges you are applying to.

Good luck with your essay, and I hope these tips help you craft a powerful narrative about overcoming challenges!

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