How do you write a compelling college essay about overcoming a challenge?

I’m a Yale graduate and college admissions advisor with over 8 years of experience helping students gain admission to top universities like Harvard, Stanford, and MIT. I’ve reviewed thousands of essays, and I can assure you that you don’t need a dramatic or life-altering event to write a compelling challenge essay — admissions officers often appreciate authentic stories about everyday struggles, as long as they’re told with reflection and specificity.

Your topic — balancing school with a part-time job — can be very strong if you focus on the depth of your reflection and the uniqueness of your perspective rather than the size of the obstacle itself. One way to make it stand out is to zoom in on a specific moment or turning point instead of summarizing the entire experience. For example, rather than saying, “I learned to manage my time better,” you could describe a day when you faced a critical decision about how to spend a lunch break before a big test and a late work shift — a decision that became a subtle but meaningful shift in how you handled responsibilities.

Go deeper than surface-level takeaways like “I learned hard work pays off.” Ask yourself: Did managing these commitments teach you an unexpected skill, reveal a passion, or change how you approach relationships? Maybe you discovered the importance of advocating for yourself, or developed a scheduling system that now anchors your approach to challenges.

Authenticity always resonates. Admissions officers can tell when an essay is honest and specific to you. I’ve worked with students who built memorable essays around seemingly small moments — like one who turned an accidental text to the wrong person during a hectic workday into a reflection on presence, adaptability, and the value of slowing down.

Focus on how the experience shaped you, and don’t shy away from admitting areas where you’re still growing. Admissions teams are looking for self-awareness and resilience, not just dramatic plotlines.

Over the past 8 years, I’ve helped thousands of students craft essays and applications that stand out at the most selective schools, including the Ivy League and Stanford. To give each student the highest level of attention, I keep my caseload small — booking early guarantees a place. I’m currently offering free consultations for new Sundial families where we’ll review your goals, brainstorm essay ideas, and outline a clear application strategy. You can book directly through my profile.

I know this process can feel overwhelming at times, but you are fully capable of navigating it successfully. I’m always here to help guide you through it. You’ve got this!