Middle school is the perfect time to build a skill that every elite college is looking for: the ability to think deeply and reflect personally. While your child may not be writing college essays for a few more years, the habits they build now, such as curiosity, self-awareness, and thoughtful communication, will shape their voice later.
As an admissions strategist who works with high school students on hundreds of college essay prompts each year, I’ve come to appreciate how incredibly rich and reflective these questions really are. So much so that I started using simplified versions of these prompts with my own late-elementary and middle school kids,and the results were incredible. These essay-inspired questions helped them think more clearly, express themselves more confidently, and see the world (and themselves) with more curiosity.
This blog offers 20 open-ended questions, each based on a real or adapted college essay prompt from schools like Stanford, MIT, Yale, Caltech, UChicago, and the Ivy League. Each question includes:
- The college prompt it’s modeled after
- A version tailored for 11–14-year-olds
- A reflection on why the question matters and what it reveals
- A tip for parents to guide a thoughtful, supportive discussion
Let’s get started.
1. If you could solve one problem in the world, what would it be—and how would you do it?
🎓 Inspired by Stanford University:
"What is the most significant challenge that society faces today?"
Why it matters: This question invites your child to look beyond themselves and think about what they believe the world needs most. Their answer reveals their values—whether they prioritize fairness, health, environment, education, or kindness.
Parent Tip: Ask, “Why does this problem matter to you personally?” Encourage them to consider both big and small ways to create change, even at their age. It’s about mindset more than mastery.
2. If you could witness any moment in history, what would it be—and why?
🎓 Inspired by Stanford University:
"What historical moment or event do you wish you could have witnessed?"
Why it matters: Choosing a historical moment helps children reflect on courage, invention, injustice, or transformation. Their choice shows how they connect to the human story and what they believe is worth remembering.
Parent Tip: Ask, “Would you want to be a bystander, or a participant in that moment?” This can lead to deeper insights into how your child views bravery, power, and leadership.
3. What’s something you’ve taught yourself just for fun?
🎓 Inspired by MIT:
"Tell us about something you do simply for the pleasure of it."
Why it matters: Colleges look for students with intellectual curiosity, and this question helps young students reflect on learning without pressure. It’s also a window into what energizes and motivates your child.
Parent Tip: Ask, “How did you stay motivated when no one was making you do it?” This can lead to valuable conversations about grit and self-direction.
4. What’s one idea or discovery that changed how you see the world?
🎓 Inspired by Columbia University:
"List the titles of the books, essays, poetry, short stories or plays you read outside of academic courses that you enjoyed most during secondary/high school."
Why it matters: This prompt helps students build the habit of connecting what they learn to how they live. Their answer will show how they absorb new ideas and let them reshape their thinking.
Parent Tip: Encourage them to reflect on how certain readings or discoveries have influenced their perspective. Ask, "What did you learn from this that changed your thinking?"
5. What’s a rule you think should be changed—and what would you replace it with?
🎓 Inspired by University of Chicago:
"What advice would a wisdom tooth have?"
Why it matters: Challenging a rule encourages independent thinking. It shows whether your child is tuned into fairness, logic, or creativity—and how they balance structure with change.
Parent Tip: Ask, “What might be a downside to your new rule?” This introduces critical thinking while still validating their ideas.
6. What’s something about you that makes you feel different—and how has that shaped who you are?
🎓 Inspired by Duke University:
"We recognize that not fully ‘fitting in’ a community or place can sometimes be difficult. Duke values the effort, resilience, and independence that may require. Feel free to share with us circumstances where something about you is different and how that’s influenced your experiences or identity."
Why it matters:
This question encourages honest reflection on times your child felt like an outsider. It helps them begin to understand how identity, inclusion, and difference shape perspective and personal growth—something college essays often explore with depth and maturity.
Parent Tip:
Instead of jumping in to offer reassurance, try asking, “When did you first notice this difference?” or “How has it changed how you treat others?” These conversations can reveal how your child copes with and grows from challenging social dynamics—an important part of self-discovery.
7. What’s something that brings you real joy—and why?
🎓 Inspired by Brown University:
"Students entering Brown bring diverse perspectives, identities, and interests. What brings you joy?"
Why it matters:
Joy is a powerful lens into identity. This question invites students to reflect on what lights them up—not what impresses others. Colleges like Brown value applicants who are deeply connected to their own sources of happiness and meaning.
Parent Tip:
Ask, “When was the last time you felt totally in your element?” or “What’s something you could do for hours without getting bored?” Helping your child name their joy makes it easier for them to pursue it with intention.
8. What’s something you changed your mind about—and what helped you see it differently?
🎓 Inspired by Princeton University:
"Tell us about a time you changed your perspective."
Why it matters: The ability to reflect and adapt is key to emotional maturity. This question encourages students to value growth over stubbornness and shows how their thinking evolves.
Parent Tip: Ask, “Was it hard to admit you were wrong or that something new made more sense?” Discussing discomfort openly helps build resilience and honesty.
9. If you could invent a school subject, what would it be—and why?
🎓 Inspired by Yale University:
"You are teaching a Yale seminar. What is it called?"
Why it matters: This question reveals what your child believes is missing from their education. It’s a fun way to see how they’d shape the world if they were in charge.
Parent Tip: Ask, “What skills or values would students learn from your class?” Help them think about long-term impact and creative expression.
10. What’s a challenge you’ve faced, and how did you deal with it?
🎓 Inspired by the Common Application:
"The lessons we take from obstacles can be fundamental to later success."
Why it matters: Reflecting on challenges helps build emotional insight and resilience. Even small struggles can reveal big strengths.
Parent Tip: Ask, “If this happened again, what would you do the same—and what would you do differently?” That’s where growth begins.
11. What’s a new skill or subject you’d love to learn—and why?
🎓 Inspired by Princeton University:
"What is a new skill you would like to learn in college?"
Why it matters:
This question taps into a student’s curiosity and desire to grow. It shows what excites them intellectually or creatively and helps them imagine learning as a lifelong adventure—not just a school requirement.
Parent Tip:
Ask, “What would it feel like to be really good at that skill?” or “Who do you know that’s great at it already?” Encouraging your child to picture themselves as a learner helps shift their mindset from “Can I?” to “When I do…”
12. Who’s someone you’ve never thanked—but really should? What would you say to them?
🎓 Inspired by University of Pennsylvania:
"Write a short thank-you note to someone you have not yet thanked and would like to acknowledge."
Why it matters:
Gratitude builds emotional intelligence. This question gives students a chance to slow down and think about people who have helped them grow—often in quiet, powerful ways. It fosters reflection, humility, and connection.
Parent Tip:
Ask, “What did this person do that stuck with you?” or “How might they feel if they heard this from you?” You can even encourage them to write and send the note. Practicing appreciation builds stronger relationships—and character.
13. What’s one question you wish someone would ask you—and how would you answer it?
🎓 Inspired by UChicago:
"Create your own prompt and respond to it."
Why it matters: This is one of the most personal questions you can ask. It gives students a chance to share what they want to talk about but don’t often get to.
Parent Tip: Ask, “Why do you think people haven’t asked that before?” It may uncover hidden parts of their identity or inner life.
14. What are three things a new friend should know about you?
🎓 Inspired by Harvard University:
"Your roommate assignment is here. Please submit a note to your future roommate that reveals something about you or that will help your roommate—and us—get to know you better."
Why it matters:
This prompt encourages students to reflect on their identity, quirks, values, and how they show up in relationships. It also helps them practice being open and welcoming—key to both friendship and future community living.
Parent Tip:
Ask, “What do you think makes you fun or easy to be around? What’s something that takes a little time to understand?” This is a great way to explore both self-confidence and emotional insight.
15. If you could redesign your school, what would be different—and why?
🎓 Inspired by Caltech:
"How have you been a creator, inventor, or problem solver in your community?"
Why it matters: Imagining a better system nurtures vision and critical thinking. It shows how your child balances creativity with practicality.
Parent Tip: Ask, “What’s one small change you think your principal might actually say yes to?” Then brainstorm together!
16. What’s one community that’s shaped who you are—and how?
🎓 Inspired by Cornell University:
"We all contribute to, and are influenced by, the communities that are meaningful to us. Share how you’ve been shaped by one of the communities you belong to."
Why it matters:
This question helps students explore the connections that define them—whether it’s family, a team, a cultural tradition, or even a shared online interest. Understanding how we are shaped by community builds identity, empathy, and gratitude.
Parent Tip:
Ask, “What’s something this community has taught you—or helped you through?” You might also explore, “How are you different when you're with that group versus others?” This kind of reflection builds self-awareness and pride in belonging.
17. What’s something new you dared to try—even though it felt uncomfortable?
🎓 Inspired by Vanderbilt University:
"Tell us about a time when you dared to try something outside of your comfort zone. Why was that important to you?"
Why it matters:
This question encourages kids to reflect on risk, vulnerability, and courage. It’s not about getting it perfect—it’s about what it feels like to stretch yourself, and why taking that step matters more than the outcome.
Parent Tip:
Ask, “What made that moment feel scary or different? What would you tell someone else who was nervous to try the same thing?” Sharing stories about growth and bravery—especially the messy kind—helps kids develop confidence and resilience.
18. What would a successful year look like for you over the next 12 months?
🎓 Inspired by Carnegie Mellon University:
"As you think ahead to the process of learning during your college years, how will you define a successful college experience?"
Why it matters:
This question brings the abstract idea of “success” down to a personal, realistic level. It helps students think intentionally about their short-term goals, values, and growth—not just achievements, but also how they want to feel, act, or relate to others.
Parent Tip:
Ask, “What’s something you’d feel proud of this time next year?” or “What does success mean to you—not to teachers or classmates, but to you?” This can guide your child toward internal motivation and help them define goals that really matter.
19. If someone asked, “Who are you?”—what would you say?
🎓 Inspired by Dartmouth College:
"‘Be yourself,’ Oscar Wilde advised. ‘Everyone else is taken.’ Introduce yourself."
Why it matters:
This question encourages middle schoolers to step into self-definition. It asks them to go beyond labels or roles and think about how they see themselves—and how they want to be seen.
Parent Tip:
Ask, “What makes you you—no matter where you are or who you're with?” You can even answer this question together. Modeling openness and curiosity makes this a powerful bonding moment, not just a writing exercise.
20. What’s something you love to wonder about—and where do you think that curiosity might take you?
🎓 Inspired by Dartmouth College:
"In 'Oh, The Thinks You Can Think,' Dr. Seuss invites us to 'Think and wonder. Wonder and think.' Imagine your anticipated academic major: How does that course of study sync with Dr. Seuss's advice to you?"
Why it matters:
Curiosity is the root of lifelong learning. This question helps kids identify what fascinates them most—whether it’s outer space, human behavior, machines, or social justice—and connects that wonder to their potential path forward.
Parent Tip:
Ask, “What’s something you keep asking questions about—even when no one’s making you?” Then ask, “If you kept following that curiosity, what might you learn or build one day?” This helps your child link imagination to future learning in a joyful, empowering way.
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