How to be cool: a Dad's guide

As a dad who’s been caught taking photos of empty baseball stadiums and explaining router security to strangers at parties, I’ve had to learn some coolness lessons the hard way. My son’s eye-rolls have been my greatest teachers.

Being cool isn’t about having the latest tech or knowing blockchain jargon (though I’ll argue those are pretty cool). It’s about carrying yourself with that quiet confidence that says, “Yeah, I know what I’m doing,” even when you absolutely don’t.

You know that person who walks into a room and everyone just kind of… gravitates toward them? They’re not doing anything special. They’re not the loudest person there. They’re definitely not flexing or trying to impress anyone. But somehow, everyone wants to talk to them. That’s the kind of coolness we’re talking about here.

The secret sauce? Authenticity with a dash of not trying too hard. The moment you chase coolness is exactly when it slips away---kind of like trying to photograph a perfect sunset while also enjoying it.

So take it from a guy whose son still occasionally says “Dad, that was actually cool”---just be yourself, but maybe turn the volume down on the enthusiasm just a notch.

Key takeaways: How to Be Cool

1. Stop trying too hard - The moment you chase coolness is when it becomes instantly uncool
2. Build confidence through small wins - Learn new skills and challenge yourself in tiny ways to create the “competence-confidence loop”
3. Be a good listener - Actually listen and ask thoughtful follow-up questions instead of waiting for your turn to talk
4. Own your real interests - Passion is attractive regardless of the subject matter, even if it’s “nerdy”
5. Admit what you don’t know - Saying “I don’t know much about that, but it sounds interesting” is cooler than faking expertise
6. Set boundaries - Cool people protect their time and say no when necessary
7. Break rules strategically - The “red sneakers effect” shows intentional nonconformity increases perceived status
8. Give genuine, specific compliments - Focus on what someone did rather than generic praise
9. Stay calm under pressure - Emotional regulation makes you someone others look to for leadership
10. Avoid neediness - Don’t constantly seek validation, be clingy, or require immediate responses

The real secret: Autonomy influences perceived coolness more than any other factor. When you’re genuinely comfortable with who you are, others are naturally drawn to you.

Table of Contents

What actually makes someone cool

Here’s something interesting I learned while overthinking this (because apparently I can’t just enjoy anything without investigating it): researchers¹ looked at nearly 6,000 people across 13 countries to understand what makes cool people, well, cool. They found that the coolest people share some pretty universal personality traits. They’re confident but not arrogant, open to new experiences, autonomous, and yeah - a little rebellious. But here’s the key part: they balance all that edge with genuine warmth.

Think about cool people like Keanu Reeves. The guy is cool not because he’s trying to be cool, but because he’s just genuinely kind to everyone. Or Ryan Gosling - quiet confidence without the ego. You know what they all have in common? They seem real. Like if you met them at a coffee shop, they’d just be… themselves.

The psychology behind this is actually fascinating. We’re drawn to people who display confidence and autonomy because these traits signal they’d be valuable allies or leaders. Consumer research shows that autonomy influences perceived coolness more than almost any other factor. We’re basically hardwired to respect people who march to their own beat.

But here’s where everyone messes up when learning how to be cool: the moment you TRY to be cool, you become instantly uncool. It’s like that scene in every sitcom where the dad tries to use teenage slang. Painful, right?

Dad’s guide to being cool

Less is more

As I tell my son, trying too hard screams “not cool.” It’s like my photography---sometimes the perfect shot happens when you’re patient and relaxed. Being comfortable in your own skin always beats frantically chasing trends.

One of the fastest ways to kill your coolness is being desperate for validation. I see this all the time - people making decisions based entirely on what will get them the most likes, the most approval, the most pats on the back. Cool people make decisions based on their own values, not on what everyone else thinks they should do.

This doesn’t mean being rude or inconsiderate. It means trusting your own judgment and being okay when not everyone agrees with your choices. The truth is, the more you chase approval, the less likely you are to actually get it. Cool people understand this - they respect themselves enough to respect others’ opinions without needing constant validation.

If this is something you struggle with (and honestly, who doesn’t?), I made a whole video breaking down exactly how to stop caring what people think:

Rock your confidence

I watch my kid walk into a room of new faces with his head high and think, “that’s it right there.” Self-assurance turns ordinary moments extraordinary. Even when you’re nervous, acting like you belong works wonders (you are who you think you are so be confident).

Look, I’m going to be honest with you: confidence is non-negotiable when learning how to be cool. But I’m not talking about that loud, chest-thumping, “look at me” kind of confidence. That’s actually just insecurity with better marketing.

Real confidence is quiet. It’s being comfortable with who you are, regardless of the situation. It’s knowing your worth without needing to announce it to everyone. Cool people carry this kind of confidence naturally - they don’t have to talk about it because everyone else can see it.

Here’s something practical: build confidence through small daily wins. Learn a new skill, complete a personal goal, challenge yourself in tiny ways. Each small success creates what psychologists call the “competence-confidence loop” - you feel more capable, which makes you act more confidently, which leads to better outcomes. The coolest thing about this? It becomes self-reinforcing over time.

Also, your body language matters more than you think. When you maintain eye contact, stand tall, and speak clearly, you not only project confidence to others - you actually start to FEEL more confident yourself. Your brain is weird like that. Cool people understand this connection between how they present themselves and how they feel inside.

Smart rule-breaking

Some rules are meant to be questioned. I teach my son there’s a difference between mindless rebellion and thoughtful risk-taking. Stand out for the right reasons---creativity and originality---not just to cause trouble.

Here’s where things get fun and where coolness really comes alive. Cool people break rules - but they do it strategically. Researchers call this the “red sneakers effect.²” When someone deliberately breaks minor social rules (like wearing red sneakers to a formal event), we actually perceive them as having higher status and more confidence, assuming the behavior is intentional.

The key word there is “intentional.” Context matters. Wearing sneakers to a black-tie event might work if you’re already established and the context is right. But showing up in sweats to a job interview just looks like you don’t understand the situation. There’s a fine line between confident nonconformity and just being clueless.

Choose quality over trends. While everyone else is chasing the latest fashion or gadget, cool people invest in timeless pieces that reflect their personal style. This shows discernment and confidence in your own taste rather than just following whatever’s popular this month.

Authenticity is key

Nothing’s cooler than being real. I’ve watched my son try to copy his friends and lose his spark. The moment he returned to his quirky self, everyone noticed. True coolness isn’t manufactured---it’s unlocked when you stop pretending.

Being authentic means sharing your real interests, even if they’re considered “nerdy” or unusual. You into obscure music? Own it. Vintage cars? Cool. Medieval history? Honestly, that sounds fascinating. Passion is attractive, regardless of the subject matter. Some of the coolest people I know are deeply into interests that most people would never think to explore - beekeeping, pottery, vintage comic books. Their enthusiasm makes these interests seem fascinating to everyone else.

It also means admitting when you don’t know something. There’s nothing cool about pretending to be an expert on everything. In fact, saying “I don’t know much about that, but it sounds interesting” is way cooler than trying to fake your way through a conversation. Nobody believes you anyway, and cool people are secure enough to admit what they don’t know.

And don’t be afraid to express your true opinions, even when they differ from the group. Respectful dissent actually increases your perceived coolness over time because it shows you think for yourself. Just make sure you’re being respectful about it - there’s a difference between having strong opinions and being that argumentative person everyone else avoids at parties.

One of the biggest mistakes I see people make in their quest for how to be cool is trying to adopt personality traits that don’t match who they really are. If you’re naturally more introverted, don’t force yourself to be the life of the party. If you’re not naturally funny (and hey, not everyone is), don’t try to be the class clown. Cool means being the best version of yourself, not a cheap imitation of someone else.

Actually talk to people (and listen)

Social skills are what turn confidence and authenticity into actual coolness in real life. But “effortless” is the key word here - forced social behavior is painful to watch and even worse to experience.

The most important social skill that cool people master? Being a good listener. Actually listen to what people are saying, ask thoughtful follow-up questions, and show genuine interest in their answers. Too many people spend conversations just waiting for their turn to talk instead of actually engaging with the other person. Don’t be that person. When you truly listen and respect what others have to say, people notice and appreciate it.

Humor is powerful, but it has to be natural. Don’t force jokes or try to be funny all the time. Cool people use humor to connect with others, not to dominate conversations or beg for attention. Sometimes the funniest thing you can do is just notice something amusing and share it genuinely. (Yes, dad jokes count. Fight me.)

Stay calm and composed, especially in stressful situations. When everyone else is panicking or overreacting, the person who keeps their cool (literally) becomes someone others look to for leadership. This doesn’t mean being emotionless - it means being emotionally regulated. It’s like being the one person who doesn’t lose it when the Wi-Fi goes down. This kind of confidence under pressure is what separates cool people from everyone else.

How you say things matters

How you speak matters just as much as what you say when it comes to coolness. Speak with clarity and purpose, avoiding too many filler words. You don’t need to use overly formal language, but cutting out the “ums” and “likes” will make you sound more confident and thoughtful. Cool people understand that communication skills matter in life.

Tell engaging stories with specific details rather than vague generalizations. Instead of saying “I had a crazy weekend,” paint a picture: “I ended up helping my neighbor catch his escaped chickens at 6 AM Sunday morning while still in my pajamas.” Details make stories memorable and create real connections. (True story, by the way. Those chickens were fast.)

Ask unique questions that spark interesting conversations and show genuine interest. Instead of “How was your weekend?” try “What’s the coolest thing you learned this week?” or “If you could have dinner with anyone, living or dead, who would it be?” These kinds of questions lead to much more engaging interactions than the standard small talk script. Cool people know how to talk in ways that make others feel interesting and valued.

Cool in different scenarios

At work

Confidence is key, but so is knowing when to pipe down. I’ve learned people actually listen more when you make space for their ideas too. My son watches everything I do---showing him that respect gets you further than always being the loudest voice.

When you give compliments at work, make them genuine and specific. Instead of generic praise, focus on something the person did or a quality they demonstrated. “I love how you always ask thoughtful questions in meetings” is much more meaningful than “you’re so smart.” Specificity shows you’re actually paying attention and that you respect their skills.

Cool people at work don’t need to dominate every conversation. They contribute meaningfully, listen actively, and respect others’ expertise. This kind of confidence - the quiet, competent kind - is what makes people want to work with you and learn from you.

At school

As a dad who volunteers for field trips (and sneaks photos of my little man while I’m there), I’ve seen how much teachers appreciate kids who participate. Jumping into discussions and helping classmates creates instant connections. My son’s confidence grows every time he raises his hand and helps other classmates.

The same principle applies whether you’re in actual school or just learning something new in life. Participate genuinely, ask real questions, show interest in the material, and help others when you can. That’s how you build a reputation as someone worth knowing. Cool people aren’t afraid to be curious and engaged - they understand that genuine interest in learning is one of the coolest personality traits you can have.

In social gatherings

Be friendly but authentic. I tell my kid it’s like baseball---you don’t need to swing at every pitch. Being genuinely interested in others works better than trying to impress everyone. The coolest people make others feel comfortable, not intimidated. They create an atmosphere where everyone else can relax and be themselves.

Become a connector. When you meet people who share common interests or could benefit from knowing each other, make introductions. This positions you as someone who’s well-connected and thoughtful about others’ needs. Plus, it creates goodwill that often comes back to benefit you later. Cool people understand that social life isn’t about collecting contacts - it’s about building genuine relationships.

Host small gatherings around shared interests. This doesn’t have to be anything fancy - it could be a movie night, a hiking group, or even just regular coffee meetups. Taking initiative to bring people together shows leadership and creates opportunities for deeper friendships. When you respect people enough to create spaces for connection, you become someone others naturally gravitate toward.

What kills coolness fast

Let’s talk about what destroys coolness faster than anything else: trying too hard. The moment you become desperate for attention or validation, you lose the very thing you’re trying to achieve. It’s brutal, but it’s true. Cool people never seem like they’re working for approval - they just live their life authentically.

Don’t copy other people’s style, interests, or personality traits. People can sense when you’re not being genuine, and it makes them uncomfortable. The coolest people develop their own sense of who they are rather than mimicking everyone else.

Avoid being overly available or saying yes to everything. Cool people have boundaries and their own lives. If you’re always free and always eager to please, it suggests you don’t have much going on. Sometimes the coolest thing you can do is politely decline an invitation because you have other plans. Respect for your own time shows self-respect.

Don’t put others down to make yourself look better. This is the opposite of cool - it’s insecurity masquerading as confidence. Cool people lift others up; they don’t need to tear anyone down to feel good about themselves. They understand that showing respect and genuine interest in others is far cooler than any attempt to seem superior.

Nothing kills coolness faster than neediness. This shows up as constantly seeking validation, being clingy in relationships, or getting upset when you don’t get immediate responses to messages. Cool people are secure enough to give others space and don’t require constant reassurance. They trust in their own worth and don’t need everyone else to validate it constantly.

Keep growing and building skills

True coolness isn’t a destination - it’s a way of being that you maintain over time in your daily life. This requires ongoing personal growth and self-awareness. The most interesting cool people never stop evolving.

Keep learning new skills and exploring interests that genuinely excite you. Stagnation is the enemy of coolness. The most magnetic people are always growing, always curious, always becoming more interesting versions of themselves. Whether it’s picking up a new hobby, developing professional skills, or just exploring things that spark your interest - keep moving forward.

Practice self-care and maintain your physical and mental health. When you feel good, you project that positive energy to others in every aspect of life. This doesn’t mean you need to be perfect, but taking care of yourself shows self-respect and gives you the energy to engage fully with life. Cool people understand that you can’t pour from an empty cup.

Set boundaries and learn to say no when necessary. Cool people protect their time and energy. They understand that saying yes to everything means saying no to the things that really matter to them. This kind of confidence in setting boundaries shows that you respect yourself and your priorities.

Stay curious about the world and keep an open mind to new experiences. Whether it’s trying a new restaurant, learning about a different culture, or just having a conversation with someone whose perspective differs from yours, curiosity keeps you interesting and engaged with life. Cool people never stop learning, never stop being interested in the world around them.

The real deal about coolness

Ultimately, striving to be cool isn’t about perfection. It’s about confidence, authenticity, and above all, having a good time in life. By simply being true to oneself, coolness becomes effortless, surprising how low-maintenance it can really be!

At the end of the day, true coolness comes from within. It’s not dependent on external validation, trends, or what everyone else thinks of you. The coolest people understand this fundamental truth: when you’re genuinely comfortable with who you are, others are naturally drawn to you. They don’t worry about what everyone else is doing - they focus on being the most authentic version of themselves.

The journey of how to be cool isn’t about transformation - it’s about becoming more authentically yourself. Start with one small change, whether it’s improving your listening skills, pursuing a genuine interest, or simply being more honest about who you are. Cool people didn’t become cool overnight - they developed confidence, skills, and self-awareness over time.

Most people spend their whole lives worried about what everyone else thinks. Cool people worry about being true to themselves. And that’s exactly what makes them worth knowing. They respect themselves enough to not chase others’ opinions, and ironically, that confidence makes everyone else respect them more.

Easy for me to say all this when my son just shrugs, says ‘Cool,’ and goes back to his Nintendo Switch. Did I actually teach him anything useful? Who knows! But that’s parenting for you—throwing wisdom against the wall like spaghetti and hoping something sticks.

The truth is, confidence and authenticity—the real ingredients of coolness—aren’t things you can fake forever. They come from doing the deeper work to build yourself to fit your real life. Because being genuinely cool starts with being genuinely you.

The coolest thing you can do right now? Stop trying so hard to be cool and start being genuinely you. Listen to your own interests, respect your own values, talk about things that actually matter to you, and build a life that reflects who you really are. That’s where the real magic happens - and that’s what makes cool people, cool.

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