My son was ten years old when he looked up from his cereal and asked, “Dad, how do you be cool?”
I had exactly zero seconds of preparation for this. I’d rehearsed the birds-and-bees talk. I had a whole speech ready for “why can’t I have a phone.” But how to be cool? I stood there holding a spatula, mouth slightly open, realizing I had no answer.
Which is ironic, because I’m a guy who once explained subnet masking to a group of parents at a birthday party. While wearing cargo shorts. Cool is not exactly my brand.
But the question stuck with me. Partly because I wanted to give my kid something real (not just “be yourself,” which is the parenting equivalent of “have you tried turning it off and on again”). And partly because I realized I’d been thinking about coolness wrong my entire life.
Table of contents
Open Table of contents
The question that stumped me
Here’s what I knew for sure: I wasn’t going to Google “how to be cool” and read my son a WikiHow article. (I checked later. It has illustrations. They’re not great.)
The real problem is that coolness is one of those things everyone recognizes but nobody can define. It’s like asking “what makes a good baseball swing?” You know it when you see it, but breaking it down into steps feels wrong. A great swing isn’t a checklist. It’s a feeling.
My son wasn’t asking because he was being picked on or struggling socially. He was just… curious. He’d noticed that some kids had this thing about them. They walked into a room and people noticed. Not because they were loud or showing off, but because they seemed comfortable. Like they belonged wherever they happened to be standing.
That’s actually a pretty advanced observation for a ten-year-old. I told him I’d think about it and get back to him, which is dad code for “I need to figure this out before I say something dumb.”
What cool actually means (from a dad who overthinks everything)
After way too much thought (I’m a chronic overthinker, which is itself not cool), I did what any totally cool person would do: I read academic papers about coolness. My wife walked by, saw what I was reading, and sighed. A knowing sigh.
Turns out researchers actually studied this.1 They surveyed nearly 6,000 people across 13 countries and asked what makes someone cool. The answers were almost identical everywhere. The cool person? Confident but not arrogant, authentic, autonomous, and warm. Not rich. Not attractive. Not trendy. Just comfortable being themselves.
My dad instincts weren’t totally off. I landed on something simple.
Cool is the gap between caring and not appearing to care.
Cool people care about things. They have passions, opinions, standards. But they don’t perform their caring for an audience. They’re not trying to prove anything to anyone. There’s this quiet solidity to them.
Think about the coolest person you’ve ever met. I’d bet they weren’t trying to impress you. They were just… being. Maybe they told a story without checking if you were laughing. Maybe they wore something weird and didn’t mention it. Maybe they disagreed with the group and said so without making it a whole thing.
My buddy Matt is like this. We worked together years ago, and the guy just has it. He shows up to meetings five minutes late with his caffeine drink of choice that week, says three things that are smarter than everything else combined, and leaves. He rotates between Eagles and Phillies hats like it’s a religion. He doesn’t care about your fantasy football league but will listen to you talk about it anyway. He never once described himself as cool, which is (of course) the coolest thing about him.
I told my son about Matt. “He doesn’t try,” I said. My son nodded like that was the most profound thing he’d ever heard. Kids get it faster than adults.
What looks cool but isn’t
This part was actually easier to explain. My son already had instincts here.
Trying to be the funniest person in the room. There’s a kid in every class who’s always “on” and cracking jokes during quiet reading time. That’s not cool. That’s anxiety wearing a costume. The actually funny kid drops one line at the perfect moment and goes back to eating his sandwich.
Name-dropping and showing off. I’ve been guilty of this. There was a phase where I’d casually mention tech conferences I’d been to. Nobody was impressed. My son once watched me do this at a neighborhood cookout and later said, “Dad, why were you being weird?” Kids are brutal and correct.
Following every trend. I watched my son try to copy his friends for a while. New slang every week. Sudden interest in things he clearly didn’t care about. He lost his spark during that phase. The moment he went back to his own weird interests (he was really into dinosaurs for a while, just dinosaurs), his friends actually thought that was cooler.
Being mean and calling it honesty. Some people think coolness is just saying whatever you want without caring who it hurts. That’s not cool. That’s just being a jerk with better marketing.
Dad-tested rules for being cool
After thinking about this for way too long (and observing my kids, my colleagues, and basically everyone at Little League), I came up with a few rules. They’re simple. That’s the point.
Stop trying so hard
This is rule number one and it carries the rest. The moment you chase coolness is exactly when it runs away from you. It’s like trying to fall asleep. The harder you try, the more awake you get.
I tell my son it’s like hitting a baseball. The kids who swing out of their shoes trying to crush it? They miss. The kid who relaxes, sees the ball, and swings smooth? Line drive up the middle.
Be comfortable in your own skin. Easier said than done, especially at ten. But the work starts with accepting that you don’t need everyone to like you. You just need to be okay with yourself.
Know your thing and own it
Everyone is into something. The cool move is to own it completely, even if (especially if) it’s not what everyone else is into.
I collect baseball cards and drag my son to games whenever I can. That’s my thing. Is it “cool” by conventional standards? Depends who you ask. But I love it, and when I talk about it, people can tell it’s real. That realness is what people respond to.
My son’s thing changes every few months (dinosaurs, then Minecraft, and now Legos). But when he’s deep in something he actually cares about? That’s when his friends lean in. Not when he’s pretending to care about whatever’s trending.
Be interested, not interesting
This one’s counterintuitive. The coolest people in any room aren’t performing. They’re asking questions. They’re actually listening. They make you feel like what you’re saying matters.
I learned this the hard way. For years I thought being cool at social events meant having good stories. So I’d show up armed with anecdotes about server outages and hiking trips. People were polite. But the conversations that actually clicked? Those happened when I shut up and asked someone about their thing.
My son figured this out at school before I did. “The popular kids aren’t the ones who talk the most, Dad. They’re the ones who actually listen.” He was eleven when he said that. I had nothing to add.
Turn the volume down one notch
I’m an enthusiastic person. I get excited about new routers. I once cornered someone at a party to explain why their Wi-Fi setup was suboptimal. (They did not ask.)
Cool people have enthusiasm, but they’ve got a governor on it. They’re not suppressing who they are. They’re just not at full blast all the time. It’s the difference between a guy who likes baseball and a guy who won’t stop talking about WAR stats at dinner.
I told my son: “Be yourself, but maybe turn the volume down just a notch.” He said, “You should try that too, Dad.” Fair point.
Cool in the real world
These rules play out differently depending on where you are.
At school (or work, same thing): Confidence matters, but so does knowing when to let someone else talk. I’ve watched my son grow just by raising his hand more and helping classmates when they’re stuck. Participation plus humility is a killer combination. People notice when you make the room better without making it about you.
In social situations: Be friendly but don’t swing at every pitch. You don’t need to be in every conversation or impress every person. Being genuinely curious about someone else works better than any rehearsed story. The coolest people at a party make others feel comfortable, not intimidated.
Online: This is where coolness gets tricky for kids (and adults). The internet rewards the loudest, most extreme version of everything. But real coolness online looks the same as offline. Post things you actually care about. Don’t perform for likes. Don’t get into arguments you wouldn’t have in person. My son doesn’t have social media yet, but we talk about this a lot.
What my kids taught me about being cool
Here’s the twist I didn’t expect: my kids have taught me more about coolness than I’ve taught them.
My son’s ability to walk into a room of strangers with his head up and just introduce himself? I couldn’t do that at his age. I still struggle with it at mine.
The way kids commit fully to whatever they’re doing. When my son plays water polo, he’s not thinking about how he looks. He’s just playing. Adults forget how to do that. We’re too busy being self-conscious to actually enjoy anything.
And the brutal honesty. When I do something uncool, my son tells me. Immediately. Without softening it. “Dad, stop doing the thing with your hands when you tell stories.” I didn’t even know I did a thing with my hands. Now I’m conscious of it, which is probably worse, but at least I know.
The biggest lesson? Kids don’t overthink coolness. They just respond to it instinctively. If you’re genuine, they lean in. If you’re fake, they check out. Adults should trust that instinct more.
The part where I wrap this up
I eventually gave my son an answer. It was something like: “Be yourself, care about your thing, don’t try too hard, and listen more than you talk.”
He shrugged, said “Cool,” and went back to his Nintendo Switch.
Did I actually teach him anything? Probably not with that one conversation. But that’s parenting for you. You’re throwing wisdom against the wall like spaghetti and hoping something sticks. And then one day your kid does something kind without being asked, or handles an awkward situation with grace, and you think maybe some of it landed.
The truth is, coolness isn’t a skill you learn once. It comes from doing the deeper work to build yourself to fit your real life. From spending quality time with the people who matter. From choosing to make things harder on purpose because growth isn’t comfortable.
Being cool is really just being comfortable with who you are. And sometimes that means being the dad who collects baseball cards and explains router security at parties.
My son still rolls his eyes at me. But every once in a while, he says, “Dad, that was actually cool.”
I’ll take it.