I’ve been working with students over the past few days on their college essays—using shared Google Docs and Zoom calls. It’s always an interesting process, and this year is no different.

Part of what makes these essays so meaningful is that we dig deep. Really deep. We look for those moments in life that carry real weight. That’s not always easy to get to, which means I ask a lot of questions:

“Have you had a particularly challenging experience?”
“How did you feel? Sad? Defeated? Frustrated? Demoralized?”
“What did you do after you felt those feelings?”

Most students are pretty uncomfortable talking about themselves this way, at least at first. But this is the path to uncovering their core values—the parts of themselves that matter most.

“And then what?” I ask again.
We go deeper. And then deeper still.

At some point, nearly every student laughs and says, “I’m telling you things I don’t usually share with anybody.”

That’s the key moment. The personal essay—the one that stands out—communicates something essential about the writer’s life, in just 650 words. That only happens when we get past surface-level experiences and into what’s real.

I’ve been helping students with college essays for over twenty years, and I still love this work. It’s personal. It’s rewarding. I’ve seen kids with average grades and test scores get into top schools because of the strength of their essays. I’ve seen students with excellent grades walk away with unexpected full-ride scholarships, their essays tipping the scale. But the part I love most is watching each student find that nugget of truth—the one that sheds real light on their life, their struggles, and who they are underneath it all.

That’s the real win, no matter where they end up going to college.

I feel lucky to do this work. Every time, I walk away knowing we’ve done something that reaches far beyond the college application process. We’ve connected. I’ve watched students push themselves to ask hard, important questions: Who am I? How do I show up in the world? What do I want my life to mean?

Honestly, we could all use someone asking us those questions from time to time. That reflection isn’t just helpful for a college essay—it’s powerful for memoir, personal essays, or any life writing that aims to tell the truth of who we are. I suspect the world might be a little better—for ourselves and for others—if we all took the time to dig that deep.