I work at a school in an auxiliary capacity — not as a teacher, but in one of those behind-the-scenes roles that quietly keeps things running.
This year, I was asked to take on something new: to serve as a mentor to seven students, walking with them from 9th grade all the way through graduation.
It’s a mix of personalities and temperaments — some outgoing and talkative, some thoughtful and reserved, and of course, the shy ones. You know the type: polite, kind, quiet… the ones who make you wonder if they’re really connecting with what’s happening around them.
The Playlist Project
Last week, in our small group meeting, we did a project I like to call “Playlist.”
Each student wrote down one or two of their favorite songs so we could build a shared Spotify playlist — something that reflects all of our tastes and maybe helps us learn a little more about each other through music.
Music is funny that way; it opens doors conversation sometimes can’t.
As we talked about the songs they picked, I mentioned that Chicago is, in my opinion, one of the greatest bands of all time. The horns, the harmonies, the songwriting — there’s just something timeless about it.
The Shy Student
Now, here’s where it gets interesting.
One of the boys in my group — the shyest one by far — didn’t say much that day. In fact, before this mentorship started, I had never met him.
That’s unusual, because in my role at the school, every student eventually comes through the school store where I work. I get to know them by name — by what they purchase, by their routines, by the small talk that happens across the counter.
But somehow, this particular student had slipped through unnoticed until this year.
The Surprise Gift
This morning, he walked in, quiet as always, but holding something in his hands.
He said, “Hey… I found this at a garage sale this weekend, and I thought you might like it.”
He handed me a cassette tape — Chicago’s If You Leave Me Now.
I was stunned. Not because of the tape itself (though it’s an awesome find), but because of what it meant.
He listened.
He remembered something I said offhand, connected it with something he found, and thought to share it with me.
The Lesson
That’s the moment mentorship surprised me.
Just when you think you’re not getting through — when you’re convinced the shy ones are drifting quietly in the background — they remind you that they’re paying attention.
That your words matter.
That they see you, too.
Mentorship isn’t always about advice or wisdom or big, profound moments. Sometimes it’s about being consistent — showing up, sharing a little of yourself, and giving space for connection to grow naturally.
And sometimes, the quietest student gives you the loudest lesson of all:
They were listening the whole time.
Soli Deo Gloria.
TheoloJeep 
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