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Writing About Your “Biggest Failure”

Brian F2025-05-01T16:30:11+00:00

Many applications will ask you to write about your “biggest failure.” This can feel like a trap. After all, aren’t your application materials supposed to make you look like an amazing SUCCESSFUL person?

If done correctly, your “Biggest Failure” essay can convey a picture of you that is successful, thoughtful, humble, and persistent. Here are three tips for writing a strong “Biggest Failure” essay!

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Brian F

Brian Fobi is the founder of Gurufi and co-founder of FourthWrite, admissions essay editing services that have helped more than 7,000 students craft honest, compelling essays for college, graduate, and professional school applications. With nearly two decades in the admissions industry — as both a university admissions reader and independent consultant — Brian has developed a deep understanding of what makes an application stand out. Before admissions consulting, Brian practiced human rights law in Johannesburg, South Africa, and has taught writing at Duke, Yale, and Harvard. He holds a B.A. in History from Washington & Lee University, a Ph.D. and Master's in History from Yale University, and a J.D. from the University of Michigan Law School. Brian's guiding principle is simple: the best essays are the honest ones. He and his team never ghostwrite, plagiarize, or rely on AI — instead, they work to bring out each client's authentic voice and help them tell their own story in the clearest, most compelling way possible.

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