The Résumé That Wasn’t His

Lessons from a Phone Call, Two Sand Cranes, and a College Kid.

Halfway Through the Teaching

My nephew Billy called me the other day, and I realized about halfway through the conversation I wasn’t the one doing the teaching.

I was outside in Florida, prepping the house for the end of winter, heading north for the summer, cleaning the downspouts full of palm fronds, a Miller Lite sitting on the window sill nearby. Two sand cranes were honking across the fairway, strutting like they owned the place. Billy heard them over the phone and laughed, wanted to know what it was. I told him, “Just a couple of birds judging me while I work.”

He was calling from Milwaukee, and at first it felt like one of those normal check-ins. A little catching up, a little small talk, both of us pretending the other’s day wasn’t secretly more interesting.

Then he dropped it on me. He’s been reading my Lenny’s Confessions posts. Not skimming, not liking and forgetting. Actually reading. Thinking. Letting them stew a little in his head. That hit me funny—part pride, part mild terror. There’s something about realizing someone you care about is paying attention to the stuff you’ve been tossing out into the world. Makes you want to apologize for at least half of it, and be proud of the other half, all at once.

Then came the question. He wanted to know how I manage to say things that land without sounding preachy. How I stay grounded while trying to help people. I had no elegant answer. Mostly I just shrugged, which is the closest I get to wisdom these days.

So I told him the truth. I don’t think it’s my job to fix anyone. I really don’t. And I sure as hell don’t carry anyone else’s burden. I learned that from a friend, someone who quietly showed me it’s not my job to fix anyone or carry their burden. That’s heavy, and it bends you in directions you didn’t sign up for. I just write. I stay in my lane. If someone reads it and takes something from it, that’s enough.

Most people, I told him, don’t need advice as much as they need someone to really listen. Not the “wait your turn” kind of listening, but the real kind. No judgment, no quick fixes, just presence. That’s what really matters. And that’s another thing my friend has shown me—sometimes the best help is just being there without trying to fix a thing.

There was a pause on the phone. That quiet where you know the other person is thinking, and you know something’s about to come out that isn’t small talk. And it did.

When Books and Birds Collide

Billy’s been reading this book, Golf in the Kingdom, and he wanted to share a passage. One that had him thinking about… well, everything, really.

It was about how we pile up inventions to make life easier, more efficient, more fun, only to lose a little of ourselves along the way. That every clever tool comes with a tiny trade—a part of our human faculty quietly withering in the background. It’s not dramatic, not meant to punch you in the face, but it sneaks up on you, and before you know it, you’re looking at your own reflection sideways.

Then he told me a story that put it in focus. A college kid came to him for a job recommendation, armed with a short résumé. Clean, structured, professional. Too professional. Like it had been vacuum-sealed in corporate polish. Billy could tell something wasn’t right. The kid admitted it: his girlfriend had written it using AI.

Billy didn’t scold him. He didn’t sigh loudly or threaten to cancel the recommendation. He just asked him a simple question: why not let it be more you? Why hand someone a version of yourself that isn’t really yours?

I almost snorted into my beer at that point. Because isn’t that the eternal dilemma of this century? Everything fast, everything polished, everything “done for you,” and yet the only thing we really own is the part we actually wrestled with.

What’s Really Lost in the Shortcut

That question isn’t just about résumés or AI. It’s about what gets lost when we let someone—or something—do the work for us. Convenience is tempting, but the struggle is where the magic happens. Where your voice grows teeth. Where your words earn their place.

Sure, AI can polish, smooth, correct. It can take your awkward sentences and turn them into perfectly structured little soldiers. But it can’t sit in the chair with you, sip your beer, and pause while you argue with your own brain over a single word. It can’t give the part of yourself that shows up in the stumbles, the hesitations, the “uh… maybe I should say it this way instead” moments. That’s what makes it yours. That’s what makes it human.

Billy wasn’t judging the kid. He was holding up a mirror and letting him think. That’s influence without shoving it down anyone’s throat. Teaching without carrying the backpack. It’s subtle. Hard to do. And yet, somehow, totally effective.

Fingerprints on the Page

Listening to him reminded me of my own writing. All the times I’ve stared at a blank screen, rewriting, deleting, starting over, wondering if it’s any good. I could’ve leaned on a tool to clean it up, make it sharper, faster, better. But then it wouldn’t be mine. It wouldn’t carry the little imperfections that make it feel like me. Writing is what I actually like doing. What would be the point if I skipped the struggle? The process—the struggle—is part of the product.

Sometimes, it takes someone else to point that out before you fully realize it yourself. And sometimes, it’s your nephew on the phone from Milwaukee who does it, and you just have to nod, sip your beer, and admit he’s right.

The Trade-Offs We Forget

That book line keeps coming back to me. Every new tool we embrace comes at a cost, sometimes small, sometimes subtle, sometimes glaring. Convenience for effort. Polished for raw. Speed for depth. Those trades are invisible until you notice them.

Billy saw it in a résumé. I see it in posts, in emails, in the ways we let tools speak for us instead of ourselves. There’s a hollow spot that creeps in if you’re not careful. The moment you skip the work of saying it yourself, you might still get a product that works—but does it live? Does it breathe? Does it have your fingerprints on it?

I like to imagine that kid reading his AI résumé aloud in the mirror, making the perfect sentences sound exactly like everyone else. I hope he laughs at himself a little and wonders if he could have done better, not by the algorithm, but by him.

Stay in Your Lane, Care Enough to Listen

I told Billy he did the right thing. Not because he caught the AI, but because he engaged with it thoughtfully. He didn’t shut the kid down. He invited him to think. That’s influence without force, teaching without preaching, helping without carrying.

I’ll keep writing my posts the same way I always have. A little rough. A little uneven. Entirely mine. If someone like Billy reads it and feels seen, or pauses for a second to think, or even just smiles quietly and nods, well… that’s exactly what I was hoping for.

And maybe that’s the balance he was asking about in the first place: how to help, how to share, how to be present without trying to fix the world. Just show up honestly, stay in your lane, and care enough to listen. That’s enough. Plenty, even.