The Secret to Great Essays? Encounters and Talking to People

“The world can be divided into two kinds of people: those who loathe talking to Uber drivers, and those who love it.”

Without fail, this is one of the openings students remember year after year. It comes from an essay by a former Principia student who was accepted to Dartmouth ED, and we share it in our Successful College Essay examples folder when students start working with us.

I can see why so many of my students want to write something just like it. The opening is bold and funny, and the essay centers upon a driver he met on a thirty-minute ride from the Chicago airport. He learns via conversation that Travis was a world domino champion, and that he hoped to bring neighbors and police officers together over domino games. The student listened closely enough to learn what Travis cared about, then reached out after the ride. They stayed in touch and eventually brought Travis’s game to the student’s church community.

The details make the essay vivid, but what stays with me is the student’s ability to treat a stranger as someone worth knowing deeply. When students ask me how they can write an essay like this, I’ve often told them to pay attention to the world, interact with people often, and notice what strikes them in those moments.

But lately, I’ve realized that advice needs a little more context.

I recently shared the Uber essay with a new student, and she told me she couldn’t quite relate: she’d only ever ridden in driverless Waymos. Her response reminded me that much has changed over the past decade when it comes to casual interaction. You can order lunch on your phone and pick it up without speaking to anyone. Your Starbucks run might only involve a quick nod at the barista who made your mobile-ordered latte. And when something difficult happens, you might be more inclined to ask Claude what to think or say before you ask a group of friends what they think.

There’s some broader context for this shift. A study of college-bound high school seniors found that those surveyed in 2016 spent about an hour less each day interacting with peers in person than those surveyed in the late 1980s. Another study found that Americans ages 15 to 24 spent 57 more minutes at home per day in 2019 than in 2003. So it’s no surprise that it feels less and less easy for students to have the kinds of connections that make something like the Uber essay possible. But that doesn’t mean it’s not worth trying. It just requires a bit more effort and intentionality.

So if you’re hoping to write an essay that feels as alive as the Uber essay, where do those experiences come from? Here are a few ways to make more room for them.

Make a Weekly Commitment Beyond Your Usual Circle

A part-time job can give you something that’s hard to plan into a school day: regular conversations with people you didn’t choose to be around. So can a volunteer shift, Scouts, or a community group that brings together people of different ages and backgrounds.

A weekly commitment puts you in a room with people you wouldn’t necessarily meet through your friends or school activities, and that thus might not have the same viewpoints and perspectives that are common to your area or class background. It’s more meaningful than one-off volunteering which doesn’t often leave time or room for depth of connection. This creates what I like to call good friction. At a job or volunteer shift, you might have to work through a misunderstanding with an older coworker, hear a view you hadn’t considered, or learn how someone’s life brought them there. Those are the conversations I want students to make more room for.

So if you work alongside someone from a different generation, take the time to ask how they got where they are. What did they think they’d do when they were your age? Which small decision led to the next one? Their answer may take you through a move, a family obligation, a job they expected to leave after a summer, or an interest they discovered much later. You’ll get a better sense of how rarely a life follows the tidy path we imagine for it.

Choose something meaningfully related to your existing activities — coaching tennis, working as a lifeguard, volunteering at a nature conservancy — then make a point of getting to know the people there. Interesting stories often begin when someone answers a question differently than you expected.

Don’t Fear Disagreement

Lately, some of my students have struggled to think of a moment for disagreement essays, which are a common supplemental essay topic for colleges. As we talk, I often realize they haven’t had many chances to work through a difference of opinion with someone outside their closest circle. But colleges are incredibly interested in how students handle exactly that kind of exchange. Harvard asks applicants about a strong disagreement and how they engaged with the other person; Johns Hopkins asks about connecting across differences, and dozens of colleges have similar questions. So it’s important to get practice actually having disagreements before you’re tasked with trying to write about them.

Disagreements don’t have to become arguments or explosions! Start with someone you trust: a longtime friend, a sibling, or a relative at the dinner table. Start with common ground and letting them know that you’d like to try out having a discussion about something you know you have different opinions on. It could be as silly and simple as whether or not to turn on the pan before you start cooking eggs, or who had the best album of 2026. You’re just trying to get practice working outside of your conversational comfort zone.

First, tell them where you disagree, then ask how they arrived at their view. Practice identifying counterarguments and conceding when you’ve been convinced. Then work your way up to more challenging topics as your comfort level grows.

If your school offers one, a debate club can give you another place to practice making a case and listening to one, with guidance and structure, as can writing opinion columns for your high school newspaper. Eventually, you can try bringing that same curiosity to a thoughtful conversation with someone whose political views differ from yours.

And remember, the ability to have good disagreements without feeling fearful is a learned skill. You can watch fun content like Subway Takes for a lighter (but still impactful!) version of a good disagreement. Or if speaking up feels like the the hard part, Toastmasters’ Youth Leadership Program offers students ages 14 to 18 practice organizing and expressing their ideas. For a conversation with higher stakes — like wanting to address systemic issues at your school, or have a tough conversation with a close friend — the tools in a book like Crucial Conversations can help you think about how to say what you mean and remain open to the other person’s response.

Go One Layer Deeper

You don’t always have to talk to a stranger to hear something new. Ask a parent about a decision they made before you were born, or a teacher what first drew them to their subject. Talk with an adult at your place of worship. If a local issue matters to you, attend a community meeting and ask someone what brought them there.

And when someone gives you an interesting answer, resist the urge to move on. “How did you get there?” is one of my favorite questions. Ask them to trace the small choices behind an experience: who encouraged them, what they tried first, when they changed direction. You may hear a version of their life that has very little in common with the tidy sequence you’d imagined.

If you want a little help getting comfortable with this, Dale Carnegie’s How to Win Friends and Influence People is old-school, but its core principles still work. Be interested in the person in front of you. Remember what they tell you. Ask about it again.

Write Things Down

This is the most important element when it comes to translating these conversations to impactful essays: don’t forget the details! When a conversation sticks with you, capture it before the details flatten out. Write down the surprising phrase, the setting, and the question that led to the answer. Then give yourself a minute to write about your own part in it. What had you assumed? Did you change your mind? Why are you still thinking about this person?

That’s the part I look for when I’m helping a student find an essay: the reflection and impact, not just what happened. The Dartmouth student could have written a pleasant account of an interesting Uber ride. Instead, he explored why talking with someone who knew nothing about his past felt so freeing, and decided to go a step further to figure out what might happen if he followed that connection beyond the ride.

Here’s the truth: I can’t promise that a conversation with a coworker, a neighbor, or someone you meet on the way home will turn into the perfect essay topic. You’ll still have to do the hard work of figuring out why it mattered and how to tell the story in your own voice.

But the essays I remember most show me how a student interacts with the world: whom they make time for, what surprises them, and how an encounter changes what they think or do next. Getting offline and into places where people can challenge your assumptions gives you more chances to develop your values and perspective. That perspective is powerful and meaningful, long before and after you write a word of your essays.