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Writer's pictureCassandra Hsiao

Blog: How to Write an Overcoming Challenges College Essay

Updated: Dec 29, 2022



As deadlines and deadlines creep up on us this year, you might be thinking to yourself: my biggest challenge is college application season. And you’re not wrong nor alone in that feeling; applying to universities is indeed a massive undertaking. When you’re confronted by a question like, “What is the biggest challenge that you’ve overcome?” it’s easy to start spiraling out—what if my biggest challenge isn’t significant enough? What if I haven’t overcome any challenges?


No fear, Cassandra’s here with 4 tips on how to write this challenging essay.


1. Don’t Look for “Big,” Look for Authentic


Some of the best “challenge” essays I’ve read are about the smaller moments in life, like not landing a dream role in a school musical or conquering stage fright. Your topic doesn’t have to be grandiose or somber or life-altering in order for this to be a good essay. In fact, if you try to force your essay into something that it’s not, your admissions officer will be able to see through that quickly; inauthenticity is the last thing you want in your essays.


Your officers know that everyone’s lives are different; what might be a huge challenge for one person might not be challenging for another, and that’s okay. What’s important here is that you choose a topic or story that you genuinely felt like was challenging to you. Forget about the scope—let’s just make it authentic to you and your voice.


Specificity is key. Even if you’re choosing a “cliche” topic, for example, challenges in the sports world, you can still make this essay sing by putting in details only you could’ve written. Everybody’s point of view is unique. Describe your situation/world in a way that has your fingerprints and lens on it.



2. Show the Struggle AND the Victory


Remember that you are telling a story with a beginning, middle and end. I like to think of it as a classic plot structure for a movie or a book. Take a look at this chart above


. See how much of the struggle or the rising action takes up? Ideally, your essay should aim for 70% struggle, 10% turning point, and 20% celebration/lessons learned. Paint us a picture of the blood, sweat and tears you went through. Let us feel the difficulty of this challenge. You might think that these details are too insignificant but if you spend time showing and not telling us the story, we’re right there in the trenches with you. We’ll empathize with you every step of the way.


A turning point in the essay is important. Often, I find that it might be an epiphany, a realization that something’s not quite working in your initial approach to overcoming a challenge. Once you write that in, this will logically and naturally propel us to the last 20%, which is showcasing the New You: what do you look like after overcoming this challenge? Have you emerged from this difficulty stronger? Braver? More equipped? Don’t tell us that, SHOW us. If you had shaky hands at the beginning before taking your first hang gliding lesson, end on an image of steady hands guiding the glider through the skies. And don’t forget to give us a taste of that sweet victory celebration too. In the same way we feel your struggle, we also want to feel your euphoria and glee at overcoming the struggle.


3. Avoid Summary


The biggest mistake I see students make is including a conclusion paragraph that neatly summarizes all the lessons learned from overcoming this challenge. Why is that a mistake? It’s a waste of real estate. If you did your job correctly, that is, SHOW and not TELL us a story of your struggle, we should implicitly understand the lessons that you’ve absorbed and how you’re a better, different person now.


It’s good that you wrote the summary/conclusion paragraph—now copy and paste it into a new document as a lamppost for your next draft. Make sure your essay reflects it; if you’re struggling to meet a word count, hold up every sentence to this lamppost and ask yourself, “does this help achieve what I want my readers to implicitly take away?”


4. Don’t Forget to Answer The Question


Some essay questions ask for more than just telling us a time where you overcame a challenge. It might ask you to make a connection to your academics and what you hope to study in the future; it might ask you to draw a line between what you overcame and how you plan to contribute to student life on their campus. Whatever it may be, make sure you answer ALL parts of the question!


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