The College Essay Meets Chess

By Allison Karpf, College Essay and Application Advisor

I have helped students and their families navigate the college application process for over a decade. When faced with the college essay, one of the first questions students ask is, “What should I write about?” My answer is to think deeply about what is most meaningful to them or what best showcases their character.

For many chess students, that answer could be to reflect on their experience playing chess. The Common Application, which most colleges accept, allows 650 words for students to showcase themselves. A good college main essay explores a student’s personal story—and tells it in a compelling way.  Choosing to write about what chess has taught them can be an excellent opportunity for a student to show what they most believe in, how chess has shaped, challenged, or helped them grow, and what they have learned from it along the way.

According to, the Common Application essay questions released for the class of 2025 are the same as last year and include seven choices:

  1. Some students have a background, identity, interest, or talent that is so meaningful they believe their application would be incomplete without it. If this sounds like you, then please share your story.

  2. 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?

  3. Reflect on a time when you questioned or challenged a belief or idea. What prompted your thinking? What was the outcome?

  4. Reflect on something that someone has done for you that has made you happy or thankful in a surprising way. How has this gratitude affected or motivated you?

  5. Discuss an accomplishment, event, or realization that sparked a period of personal growth and a new understanding of yourself or others.

  6. Describe a topic, idea, or concept you find so engaging that it makes you lose all track of time. Why does it captivate you? What or who do you turn to when you want to learn more?

  7. Share an essay on any topic of your choice. It can be one you’ve already written, one that responds to a different prompt, or one of your own design.

A chess student could choose any one of these seven and find a way to discuss how chess has impacted their life or their communities.

Below are two examples of recent students who answered essay choices #1 and #4 above and allowed me to share their essays anonymously. They will both be attending top universities this fall.

Student Example- Common App Essay Question #1:

I was 5 years old, rain pounded the roof, and Bart Simpson was about to change my life. My twin sister and I were entertaining ourselves by running in circles and shrieking while my grandparents no doubt regretted their choice to visit that day. Every time I ran past the shelf that held my dad’s prized Simpsons chess set (the pieces were characters from the TV show), my eyes would linger on the shiny colorful tin. Grandpa finally grabbed the set and told my dad the time had come to open it so he could introduce the game to us. Dad argued that the collectible would one day be our college funds, but Grandpa’s persistence eventually convinced him. Over the next few hours, Bart, Lisa, Homer, and Marge (and Grandpa) taught us the basics of chess—how to set up the board, how each piece moves, and how to look for danger, then a good move, then a better move. I was so captivated by the elegant dance of the pieces that when first grade started, I couldn’t wait to join the school chess team.

I was 7 years old, at my first tournament, the State Championship. My way-too-big team t-shirt reached past my knees as I sat nervously across from each opponent. I lost all five rounds. The ability to look a few moves ahead wouldn’t come until later. Despite the losses, I had fun with my teammates and felt a part of something special. There’s a saying in chess: you learn more by losing to better players than winning. I was young enough to accept this. Messy handwriting aside, I started notating my games so I could study them.

I was 9 years old, heading to the National Championship in Louisville, Kentucky. The tournament took place in the ballroom of a massive hotel that was also hosting a bodybuilding competition. Our coach secured a team room where we could hang out between matches, and the huge bodybuilders stopped by to cheer us on and ask for chess pointers. I started to use more sophisticated openings like the King’s Gambit and Sicilian Defense, resulting in a few wins. I came home with a small trophy, a commemorative Louisville Slugger, and instructions on how to always work two muscle groups at a time.

Photo by Evan Rabin at HIgh Schoo
Photo by National Master Evan Rabin at 2024 High School Nationals in Baltimore

I was 11 years old, and I’d just tied for first place in my section at the Supernational Scholastic Chess Championship in Nashville, Tennessee. At 5300 kids, it was the largest tournament in history. As I walked across the stage to cheers and applause, I felt exhilaration. The trophy I received was almost as tall as me. When I carried it off, the top accidentally hit the floor and snapped off, but I could fix that later. The fact that my score helped our team take second place in the country meant more to me than the individual win.

Today, I am 17 years old. The access to online chess allows me to interact with players from Albania to Zimbabwe. As Captain of the Chess Team, I get to pass along my love of the game to younger kids. I teach them not to fall for the four-move checkmate, to “play the board, not the player,” and to recognize the life lessons chess can teach us. In tournaments, if a player touches a piece, they must move it. The consequences of their choice affect the rest of the game. I now find myself facing decisions about the future that will directly affect the rest of my life. Over all the years of losing many more games than I’ve won, I’ve unknowingly been training myself to make intentional choices, pivot when needed, and recognize that each new board is a fresh start.

It turns out that the Simpsons chess set is currently worth only $39.99 on eBay. To me, though, it will always be priceless.

Student Example–Common App Question #4:

My living room was a portal. Set beneath the television stand was the chess set my dad had bought for my 10th birthday; on the screen above played a warm, quippy gentleman lecturing on chess theory–this was Grandmaster Ben Finegold. And me? I was glued to the couch, envisioning myself in his lecture room, nodding along to his stories, inside jokes, and teachings.

Over the summer of 5th grade, my dad’s job took us on a new move to a new country, the US. I discovered Ben shortly after the move, and in that next month, I watched every one of his video lectures–120 hours worth. I loved chess, and I wanted nothing more than to find a community like Ben’s.

Instead, chess became something very different.

I came home after my first chess tournament as a victor: I won all my games, and in my hands was a trophy to boot. My mom and I were delighted; I would become a chess prodigy. The next year was daily training, coaching, and 51 more tournaments.

Just two years after I began tournament chess, I had pushed into the top 100 players in my age group. A year after that, I was a US Chess Candidate Master. I had succeeded–yet this way of chess was unlike what I had first imagined. Along the way, the beauty that came with chess had left me. I found myself playing for results–not to actually play chess. It felt soulless. When the pandemic hit, it was a relief–tournaments were over, and for me, it was a much-needed escape.

Months later, while scrolling on YouTube, an old Ben Finegold lecture appeared on my feed. I clicked on it; immediately, I felt the warm embrace of a reunion with a long-forgotten friend: “I’m Grandmaster Ben Finegold, and you’re not.” As I continued to watch, the shell began to crack. Ben and his community did not play to reach a title or win a prize. They loved chess and loved it together; that was all that mattered.

On a whim, I sent out a flier to my town’s Facebook page for a summer chess camp. And then something unexpected happened. My one class grew to two, then to three. The response was overwhelming; after just one week, my camp–and schedule–had reached capacity. As a chess player, I never lost sight of my love of chess–I just forgot how I was meant to play. Now, as an instructor, I would show my students that chess is not about competition but camaraderie.

I found a bit of magic in teaching chess that first summer. Watching my students embrace my lessons through confidently mastered opening strategies and boldly executed battle plans brought me pride I never felt on my solitary journey. I recruited a friend to assist the effort: we dubbed the coming year our “Expansion Era.” Soon, we were teaching a crowd of two dozen students in our library’s meeting hall. Chess was no longer just a path to personal achievement; it was a community.

Our small library club has blossomed into a national non-profit. As I prepare for Monday night lectures, I put on an old Ben Finegold video as a reminder that chess is a game meant to be enjoyed for its own sake

Eventually, I met Ben online; we played chess and chatted briefly. I do not remember how it ended; I’m pretty sure Ben beat me, but I didn’t care. Through my club and Ben’s teaching, I had already won–and that was the real reward.

I thanked him for the game.

And I thank these students for their excellent commentaries on the many lessons and heroes found in chess! For more information on how your student can bring chess (or their favorite passion and values) into a strong college Common Application essay and complete college application, feel free to reach out.

Allison Karpf is a former high school English teacher. She holds a bachelor’s degree in English from the University of California, Berkeley, a master’s degree in Education from Stanford University, and a NJ English Teaching Credential.  

Allison helps students find their voices and create original narratives for their college essays. She guides them through each step of the college process: Common Application, college list, and all essays. She either meets students face-to-face locally in the Northern New Jersey/NYC area or works nationally and globally over Zoom. 

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