How to Be Cool: 4 Lessons from Science and Hollywood

I taught myself how to be “cool” as a junior high student many years ago. It was an intuitive process for me at the time, though filled with social experiments and trial and error – and lots of beating up on myself to get it just right.

I’ve spent years trying to figure out a good way to teach all the aspects of being cool. A way to boil it all down to something simple, streamlined, and easily remembered and used by anyone who aspires to “cool”: who wants to be that person that everybody else just looks at and says, “Man, that guy is cool.”

How do you transform someone who “doesn’t get it” – whom others laugh at, make fun of, disrespect, or ignore – into someone they look up to, gravitate toward, and esteem?

To do this, of course, you need good tactics – you need to be able to give them the “what to do”; but more than this, you need the underlying principles: what is it about cool people that just makes them so damn cool?

Well, after years of non-starters on an article about this, I will say that I have successfully boiled “cool” down to four (4) core elements that are eminently doable and absolutely teachable.

Get all four of these right, and you will be – without question – unstoppably, unspeakably, almost unbearably cool.

And the best news is, all any of them takes is a little practice and, yes... a little discipline.

What Does It Mean to “Be Cool”?

Before we get too deep in, let’s take a breath and define “cool.” What is it?

The word “cool” as a positive description of an individual entered the modern lexicon to describe someone’s composure:

“He’s as cool as a cucumber.”

All that means is that he’s calm; he’s impassive; he’s unmoving.

Rather than hot and high-spirited, he is suave and composed. Maybe even calculating... or at least thinking 3 or 4 steps ahead of everyone else in the room.

We look with admiration upon people who remain unflappable even in high stress situations (and in fact, this will be a central tenet for our understanding how to be cool), and we do so with almost alarming breadth.

In The Dark Knight, Heath Ledger’s Joker is “cooler” than Christian Bale’s Batman because the Batman gets angry when you push his buttons right. Meanwhile, no matter how unexpected the situation or how well his opponents succeed, the Joker never loses his cool, and never gives up the appearance of being completely in control and having things playing right into his hands.

Not to mention the fact that he constantly adds “value” (in terms of insights, information, energy), achieves massive outcomes with seemingly little effort, and breaks rules like the anti-authority psychopath he is... all while challenging others to step up their games and join him, too.

Psychopaths / sociopaths (of which Ledger’s Joker character was one) are demonized in the media and made to sound like pure out-of-control nut jobs, but when you meet them in real life, they are frequently among the most magnetic, charismatic, interpersonally appealing individuals you will meet – because they are very cool customers.

You will also frequently notice that many experienced military veterans and many successful entrepreneurs also come across as extremely “cool” – this is not just the domain of those with their empathy switches turned off. Why? In their cases, they’ve generally faced massive amounts of hardship and punishment, and come through a crucible of trials and tribulations and survived:

• The military man surviving basic training, combat, and hazing experiences, putting himself through a gauntlet of discipline and navigating the military chain of command when he’s typically come from a loose and supervision-free background

• The entrepreneur surviving years of near-failure, trying to not go out of business despite no income and spiraling debt, fighting with the world to make it, beating back vultures who want to prey on his meager early successes, figuring out a path without anyone to guide him, and emerging as one of the few success stories in a realm where 9 out of 10 fail out within a few years, and most of the remaining 1 out of 10 never make more than a middle class income.

On the other side of these experiences, the other side of the fire, is a level of self-sufficiency and a degree of “seen it all, been through it all” that the average man does not know and cannot know, which leaves the military veteran or entrepreneurial success story or others similar to them cooler and calmer and less intimidated by the vagaries of life than the majority of the masses around him.

How to Be Cool: The 4-Part Coolness Formula

Obviously then, unflappability is one part of our 4-part formula. Here’s what all four of the parts are:

1. Always provides value; never only takes it

2. Remains cool and unflappable; always in control

3. Sticks to the Law of Least Effort religiously

4. Breaks the rules at least some of the time
   

Before you wave your hands and announce is too much for you, let’s talk about what these aren’t.

“Always provides value; never only takes it” doesn’t mean that someone cool never receives value. To the contrary; thanks to the Law of Least Effort, cool people are tremendously focused on attaining results for their efforts.

Rather, what it means – and we’ll explore this much more in-depth below – is that even while they get value, they give MORE value. They are virtual value-distribution machines.

“Remains cool and unflappable; always in control” does not mean that they do not feel emotion, either. Cool people can, and do, feel, just like regular people. What it means instead (and again, much more to come on this in just a moment) is that they modulate (control and temper) their external emotional displays, and force themselves to think before they act. You might just as easily say that they are very careful about how they react in all manner of situations.

“Sticks to the Law of Least Effort religiously” does not mean that cool individuals take no action so as to seem minimally effortful. The Law of Least Effort has two parts: minimize effort while maximizing returns. Someone who dives to catch a baseball in a natural, unrushed, effortless-looking way is a firmer adherent of the Law of Least Effort than someone who stands still and doesn’t bother when he could catch the ball because he doesn’t want to look like he’s exerting too much effort. The latter man simply looks inept, and ineptitude is the antithesis of the Law’s focus on results and capability.

Lastly, “Breaks the rules at least some of the time” does not mean you go around stealing knick-knacks and vandalizing buildings and ripping off old ladies. Although, if you do a few of these things, much as I hate to admit it, it probably will make you cooler (to a point). There are lots of ways to break the rules, however; the main point of this one is that you are not controlled by the rules.

Now let’s dive into the meat of this article, and busy our minds on how to be cool.

Cool Factor #1: Always Provide Value

One of the Commandments of Cool: always provide value; never take it.

The first thing I look for whenever someone tells me he doesn’t know how to be cool and that other people don’t like him, or consider him annoying, or exclude him from groups, is someone who operates from a negative value position.

That is, he’s someone who does not add value to the social situations he enters himself into; he subtracts it.

He siphons it away.

He attempts to tap other people for his own social needs, without providing sufficient payment to them for this up front.

Here are some of the ways guys make themselves look uncool with this accidentally:

• Trying to lead in ways that don’t match the group. For example, hanging out with a group of guys and girls who really just want to relax and talk, and he starts proposing that they all go out and play Frisbee since the weather’s so nice... but this is completely misaligned with the vibe of the group. This forces everyone else to have to try to communicate their disinterest in the idea to him, which hurts the vibe and detracts from the emotions of the situation.

• Asking for value without providing sufficient return value. An example of this is asking someone for help or whether he can borrow XYZ object, without providing at least some social value in return – a warm smile, graciousness, and a sense of appreciation from a high value person, for instance. Alternately, he may attempt to offer return value, but it’s not properly gauged and isn’t something the other person values, or isn’t valuable enough to balance out what he’s asking for (e.g., a value imbalance). Thus, he’s a net drain on value as a result.

• Directly or indirectly insulting others. Cracking jokes at others’ expense, “tooling” others, positioning oneself as “over” or “above” something others have expressed interest in – all are examples of posturing that others pick up on and detract from the overall value being passed around. Sometimes people lower on the social ladder think this behavior signifies “coolness” since they see those higher up than them doing it, but it’s really social ladder climber behavior and you never see it in the upper echelons of “cool”... it’s more the behavior of the middle and lower upper individuals, infighting with each other for minor (and often fleeting) position changes. People who do this and seem somewhat cool owe their coolness to other factors, not this; they are cool (kind of... if you’re lower on the ladder than they are) in spite of this behavior.
  

• Bring the mood down with negativity. Complaining, whining, bitching, moaning, fatalism, pessimism, victim mentality – all these things are major detractions from the mood and make someone seem genuinely uncool. Cool people can be sad... but they are sad in powerful, contemplative ways – they do not complain, bitch, whine, or mope about, because they are not lashing out impotently, nor are they casting about for help. They are only momentarily sad, reflecting on a loss or defeat before picking themselves back up and sallying forth once more into the fray to go get what they want out of life.
  

The individual who knows how to be cool follows a different set of rules than these; while the uncool individual looks tryhard because he is following a rule set of, essentially:

1. Try to take the lead
2. Get the stuff you want
3. Position yourself as powerful
4. Gripe to get attention and compel others to help
   

... while the cool individual follows a completely contrary set of rules:

1. Lead if the group needs it and will benefit from it
2. Provide value to others, in exchange for value, or just for fun
3. Ignore selfish status jockeying (and shrug off anyone who tries it)
4. Never bring the group down with your own problems or weaknesses
   

See the difference in the mental models of the uncool person and the cool person?

• The uncool person is very focused on his status within the group
• The cool person is almost entirely focused on what he brings to the group
  

While the uncool person looks around for ways to steer the group or take control of the group or get value from the group, the cool person thinks about how he can add to the group and provide value to the group and be a net positive addition to the group.

The result? The guy who provides the MOST social value to the group becomes the most highly VALUED member of the group.

Ways you can provide social value:

• Make well-timed, amusing jokes
• Tell engaging stories that people enjoy
• Lead the group when it’s what the group wants and needs
  
• Bring good emotions and positive energy to the group
• If you ask for value, provide equal or superior value in return
• Instead of tearing others down, build up their value and grant social status
• Any time you can’t provide value, just stay quiet and wait until you can
  

The overall rule that all extremely cool people obey:

Make EVERY action a VALUE-GIVING one.

Every time a cool person interacts with other people, his aim is to provide value.

Even if he’s asking for investment – he does it in a way that still provides value.

If you listen to the voice tone used when making requests and commands, you will notice that the tone itself does not come across as if it’s much asking for or trying to get something from the other person, unlike the “neutral” or “normal” tone people ask for things in – instead, the communication is, “If you’d like to provide this to me, I am a high value person and you will have my gratitude.”

(now, if she doesn’t genuinely see you as high value, this comes off annoying / uncool / an attempt to siphon off value anyway; if she does, then this comes across exactly as you intend it to. So, the perception of the individual remains crucial to how his actions are interpreted – don’t go demanding compliance before she views you as a high value / high status male and you can make the request seem value-giving instead of value-taking)

The gist of it is, people want to be around people who constantly provide value, and they don’t want to be around people who take it.

If you work hard at being someone who is just a bottomless well of infinite value in every interaction you participate in, people will seek you out as someone they simply must have around... because they want access to all that value (and at that point, you’re responsible for selecting as friends and associates those people who “get it” and provide value back to you, and screening out the vampires who only want to suck you dry).

Note that there is a learning curve to this, and you will spend time putting yourself out there and trying to be valuable and having some of your attempts fall flat and make you look tryhard or even value-taking. That’s okay. If you keep the focus on refining your actions and presentation to make everything you do net positive in social value for all involved, you will develop this ability rapidly and get there sooner rather than later.

As discussed in “Sprezzatura”, you must spend some time as Jester before you become King.

Simply be mindful of that as you do, and keep in mind that the King is the end destination with the Jester a mere pit stop on the road to there; do this, and you will hone your capacity to provide value in all situations to a razor’s edge.

Cool Factor #2: Be Unflappable at All Times

This is the one that seems to trip people’s kneejerk reactions most often: “Why should I have to be calm and controlled all the time? Sometimes life is unpredictable! This is a completely unreasonable expectation!”

Here’s the thing though: how cool does anybody reacting that way appear to you to be?

The man who knows how to be cool knows how to stay in control. He’s the one on top of the ball in all situations, and no matter how insane things get, they’re either playing into his hands, or will be shortly.

Why is this “cool”? Because all “cool” is, ultimately, is a signal of social preeminence, and the man who knows how to pull out a win out of even the most dire situations is inevitably the man we look to in those and other situations. He is the truest, most reliable, and most admirable kind of man: he’s the kind we’d all secretly (or not so secretly) like to be.

Before you say, “But I have emotions!” keep in mind that “unflappable” doesn’t mean you never show any emotion ever.

The cool man gets angry when the situation calls for it; and he shows passion when the time comes.

However, even in these moments of emotion, he remains in control – of his surroundings, and himself. His passions are directed passions, and at no point does he relinquish control of the moment.

The cool man’s anger is never an impotent cry of, “Why? It’s not fair!” but rather a powerful one of, “This is an outrage – and you will pay.”

The cool man’s passion is never a pleading one of, “I’ll do anything to be with you!” but rather a mighty one of, “I will ravish you; I will give you the experience of a lifetime.”

Here are some of the mistakes individuals make along these lines that make them look patently uncool:

• Begging or pleading. Nothing says, “I have no control over my life or person,” like begging or pleading. “Please! I need your help! I’ll do anything!” Subtract 50 cool points then and there. Not only does this make you look the polar opposite of unflappable and in-control, but it also makes you an instant social burden – here is this person who’s so low value socially that he can’t offer you anything for your help... all he can do is beg it. Makes one wonder what all those men are thinking who write songs for the radio begging women to give them a second chance... because if she was ambivalent about them before, one spin of that song on the radio and she will despise them after.
  

• Complaining, bitterness, and victim mentality. Next in line is complaining, bitterness, and victim mentality. Why do people do / become these things? People complain when they want something and can’t get it. People become bitter when they want something and can’t get it repeatedly. And people descend into victim mentality when they want something and can’t get it over the long-term with just about everything in their lives. Now which of these communicates power, control, efficacy, and capability? None of ‘em. And they’re among the most off-putting behaviors you can put on display.

• Being a sore loser. Everyone loses, quits, and fails at things. Cool people probably do more than most, actually – because, very often, they have more active lives with more experiences, and try many new things. Failure is an inescapable part of this. There are many ways to handle failure gracefully that actually enhance your cool and cause others to admire you more – but uncool people don’t do these. If they fail at something, they go whine, pout, and mope around. They blame others for their failure. They dismiss the thing they failed at as “a waste of time” or “beneath them” or “not worth it anyway.” But everyone who hears someone say something like this knows what it really means; it isn’t an accurate judgment of the worth of the thing being assessed, but rather a mark of the proclaimer’s inability to control his outcome and get the result he so very much desired. Not cool.

• Indecision. “Let’s go here... no wait, let’s go there.” “Why don’t you pick... no, I don’t like that choice of yours. Nah, that one’s no good either. What, ME pick? No, I don’t really have an opinion...” “Wait, so should I do this? Or the other one? How to choose...” Indecision due to lack of information is understandable – but what a cool person does in this case is to decisively pursue the required information. Don’t know what’s behind Door #1 or Door #2? “So, before I choose one of these, what’s behind Door #1 and Door #2?” They won’t tell you and there’s no way to get that information? Then just pick one. Unless you’re telepathic, the answer won’t just “come” to you. It’s not hard to be decisive – but many people aren’t, and it’s major negative cool points when you can’t make up your mind.
  

The uncool person appears weak and impotent to the outside observer because he follows a set of rules whereby he strips himself (or, as he would see it, is stripped by unbeatable outside forces) of all his power:

1. If other people have things he wants, all he can do is hope they’ll share
2. When life goes awry, he complains, hoping others will hear and help him
3. When he loses, he pouts, hoping others will give him consolation
4. When it’s time to decide, he puts it off, not wanting to risk being wrong
   

... meanwhile, the cool person does and thinks the opposite of these:

1. If others have things he wants, he just needs to find out what THEY want
2. When life goes awry, he grabs his balls and gets back out there to fix it
3. When he loses, he accepts this graciously, and resolves to do better next time
4. When it’s time to decide, he simply decides; if he’s wrong, no big deal
   

In this case, there are two (2) key mindset differences between the cool vs. the uncool approach to “control” over one’s own life and sphere (and, to a degree, all the people and situations within it).

The first of these, related to personal power and effectiveness, is:

• The uncool person sees himself as a recipient of the effects of life
• The cool person operates as an actor who causes life’s effects

The second of these, related to the “seriousness” of life, is:

• The uncool person takes everything VERY seriously – it’s all a big deal
• The cool person takes everything in stride – if it doesn’t work out, I’ll try again
  

These two little differences lead to an ENORMOUSLY different way of dealing with the world, with opportunities, with risks, and with hardship.

Where the uncool person tosses up his hands in the face of adversity and says, “See? More proof that it’s utterly futile!” the cool person only smiles, squints, and says, “You want to play hard, life? Well, I play harder.”

The latter – the man with grit – is the kind of man we admire and respect.

These are all mentalities you can develop, and to some extent are a lifelong endeavor. The things you have the least experience with (and the least success with) you will always tend to blow up into the biggest deals and view as the most life-or-death issues around you. The more experienced and the more successful you become, the less of a big deal they are.

Which is another reason that very calm, cool, “devil may care”, unflappable men seem so damn powerful – the implication is that they’ve been there, done that, and succeeded in all manner of arenas.

They are life’s winners. They are the victors.

And everybody wants to be friends with the winner.

Cool Factor #3: Stick to the Law of Least Effort

While it isn’t something most people talk about, it is something that every cool-looking, socially powerful, and masterfully experienced person does: he adheres very closely to the Law of Least Effort.

Whether you watch a master fly fisher effortlessly cast his line, then smoothly reel in and yank back up a giant fish before you know it, only to wonder to yourself, “How on Earth did he do that? I can leave a hook out there all day and catch nothing!”... or you watch a beautiful woman slink through a crowd in a nightclub commanding the attention of everyone around her despite her slow movements and statue-like poise... that’s the Law in action.

All this is is the outward appearance of minimal visible effort, coupled with the achievement of maximum, and often outsize, results.

Place a novice piano player next to a master pianist. The novice works very noticeably diligently, but his playing sounds rough and his songs are basic. The master plays effortlessly (unless he’s on a very dramatic piece and putting on a good show), but his playing is beautiful and his songs are complex. We immediately hold the master in far more esteem than the novice, and the relationship of effort to outcome is why.

Every cool person you will ever meet instinctively knows this, and constantly and very often consciously works to minimize the apparent effort he puts out while maximizing his apparent effectiveness.

Most “regular” people do not understand this aspect of social power, however, and focus more on gaining equivalency of effort to outcome – I should be able to put effort in and get an equal amount of outcome back out, they think.

You wouldn’t pull ten all nighters in a row just to pass a 10-question quiz responsible for 5% of your grade in school, for instance. You want to balance out the effort you put into it with the outcome.

But people who are neither focused on how to be cool nor on how to master anything usually do not strive to go beyond a net neutral effort-to-outcome ratio in their lives. Going one more than this takes a level of expertise and dedication that most people simply don’t want to put the energy into acquiring.

Here’s what the uncool get all wrong about the Law of Least Effort:

• Chasing with little thought to image. These are the guys who just dump epic loads of highly visible effort into chasing vigorously after whatever they’re trying to get. If that makes them look pathetically desperate in the meanwhile... so be it! While persistence is good, it’s a very different thing from chasing. You must be able to set your ego aside to get good at anything and let people watch you persist and fail and try again, but the folks who are uncool are the ones who set ego so far to the side that they will relentlessly hound people far past the point of any normal persistence and far outside their own skill levels, making them look both inelegant and incapable.

• Results are consistently poor. The cool individual gets consistently great results for (apparently, though not always actually) little effort. The uncool individual gets consistently negligible results for consistently Herculean effort. This is the guy who is practicing the same exact tennis serve every time you walk by the tennis court and he never gets any better. This is almost always a failure of identifying what his weak points are and fixing them, and/or of seeking out a mentor who can do this for him... so he just repeats the same actions again and again without ever getting better, like one of those wind-up toys that walks around and around in a circle, forever destined to repeat itself. To anyone paying attention, this looks distinctly uncool.

• Doesn’t play down effort. Talk to an uncool person about something he’s working on, and the first thing you will usually hear from him is how hard he’s working. The next thing you will hear is how meager his results are. This is opposite what you’ll hear from a cool person, who will imply he’s done little to no work, while reaping great rewards. The reality is that somewhere along the line the cool person has done a lot of work to reach the point where he can reap those rewards, but he knows it makes him look a lot more powerful if he can represent himself as mysterious and naturally just “falling into” his returns. The uncool person doesn’t get this, and instead tries to glorify himself by pointing to how hard he’s working despite the lack of result... which only makes him seem ineffectual.

• Failure to casually advertise results. Just as the uncool person plays up his effort, he also typically either plays down his results, or goes too far in promoting them. When playing them down, this can be because he’s unhappy with his performance, compared to other people he’s aspiring to match or surpass, and he communicates this disappointment loudly and clearly; when playing them up to far it may be because he thinks if he beats his chest loudly he can willpower others into amazement and awe. Typically, both leave observers feeling like his results are paltry... especially next to the massive effort he’s apparently had to put in to get them.
  

The uncool individual follows a rule set regarding to effort/results that dictates he:

1. Chase down the things he wants doggedly no matter how it looks
2. Keeping swinging for the fences over and over and over until he gets a hit
3. Discuss his level of effort expended, so everyone knows how hard he works
4. Pan his results, because he’s displeased, or brag about underwhelming results
   

Meanwhile, the cool individual follows a different set of rules:

1. Pursue the things you want, but be mindful of how you’re perceived
2. If something isn’t working, figure out why, and tweak it for effectiveness
3. Play down your level of effort expended – no one cares how hard you worked
   
4. Discuss results casually and gracefully, communicating experience winning
   

The mindsets here that differ are:

• The uncool person wants to be seen as hard-working and just unlucky
  
• The cool person wants to be seen as effortless, effective, and lucky
  

In other words, the uncool person is trying to explain away his lack of success by saying, “Hey, I’m trying!”

Meanwhile, the cool person is just successful.

Because of these mindset differences, the uncool person will go out of his way to show off his mountains of hard work, while also showing off his dissatisfaction with his results. He hopes that you will admire him for his pluck and determination... when oftentimes all that happens is he ends up looking like someone working really hard to push a dump truck by hand to the other side of the street when there’s a tow car just down the block. This only looks like madness and idiocy.

The cool person, on the other hand, is extremely aware how idiotic large amounts of effort without equal or greater returns appear to people, and so conceals his effort to minimize the risk of him being perceived socially as inept or idiotic. When effort is invisible, even small returns look good, and LARGE ones make the cool individual look like a rock star because of the multiplier effect.

Perceived result divided by perceived effort:

• The uncool guy appears to put in 200 effort and gets 5 result. His resulting social power is 2.5%

• The cool guy appears to put in 6 effort and gets 10 result. His resulting social power is 166.7%

Those are made up numbers, but I’m convinced the brain uses a similarly simplistic calculation to determine raw social power – it’s perceived results divided by perceived effort (the reason it doesn’t use “real” results and “real” effort is because these are subjective and unknowable – instead, the brain calculates based on what it perceives a given individual’s results and efforts in a given undertaking seem to be).

Now, there’s another mindset difference between cool people and uncool people when it comes to the Law of Least Effort, too:

• The uncool person avoids getting out of his element because he fears failure
• The cool person seeks to get out of his element to up his experience levels
  

We’ll talk about these more just below in the section on breaking rules. Interestingly, there’s some overlap between these two; rule breaking can also be a far more efficient means of achieving an objective, and, therefore, sometimes the Law of Least Effort will all but require bending or breaking of rules.

Regardless, by increasing his experience in unfamiliar environments, the individual who knows how to be cool knows he can make himself both more unflappable the next time he encounters similar situations, and he can gain experience doing a thing so that he can get better results with less effort the next time around.

The uncool person generally is extremely rigid and does not want to go out of his element, because he already struggles enough in familiar situations, and he reasons that spending a lot of time in unfamiliar situations will just be like this, multiplied a hundredfold. He never realizes that exposure to a wider variety of new situations and experiences will actually make him cooler both in new situations, and in the ones he’s already familiar with right now.

Cool Factor #4: Break the Rules

According to the 2012 paper “Coolness: An empirical investigation”, published in the Journal of Individual Differences, breaking the rules is one of the key elements of being cool... so beyond intuitive correctness, this point now has some empirical research backing it up, too:

“Some people are routinely described as “cool,” but it is unknown whether this descriptor conveys trait-like information beyond mere likability or popularity. This is the first systematic quantitative investigation of coolness from a trait perspective. Three studies of North Americans (N = 918) converged to identify personality markers for coolness. Study 1 participants described coolness largely by referring to socially desirable attributes (e.g., social, popular, talented). Study 2 provided further evidence of the relationship between coolness and social desirability, yet also identified systematic discrepancies between valuations of coolness and social desirability. Factor analyses (Studies 2 and 3) indicated that coolness was primarily conceptualized in terms of active, status-promoting, socially desirable characteristics (“Cachet coolness”), though a second orthogonal factor (“Contrarian coolness”) portrayed cool as rebellious, rough, and emotionally controlled. Study 3, which examined peer valuations of coolness, showed considerable overlap with abstract evaluations of the construct. We conclude that coolness is reducible to two conceptually coherent and distinct personality orientations: one outward focused and attuned to external valuations, the other more independent, rebellious, and countercultural. These results have implications for both basic and applied research and theory in personality and social psychology.”

While the researchers concluded that there two different “kinds” of cool, and boxed rebelliousness / rule-breaking in with only one of these, I’ve yet to see anyone considered “cool” who doesn’t liberally break rules in various ways.

And believe it or not, almost any kind of rule-breaking wins you cool points; even going on a rage-fueled, senseless murdering spree, like the one Elliot Rodger went on in Southern California, can turn you from a zero to a hero quite quickly... as evidenced by the sudden surge in female attention and admiration the guy who’d never kissed a girl received following his murderous (and suicidal) spree: “In Death, Girls (and Boys) Swoon Over Santa Barbara Mass Murderer.” You see this same thing with virtually every serial killer or rule breaker of every sort.

It’s also why you getting arrested by the police is undeniably hot to women, and if you’ve never been cuffed and stuffed into the back of a cruiser, well, as someone who’s been in that position several times, I can’t say I’d recommend it, but if it happens to you, don’t forget to thank the officers for keeping you off the streets and in women’s beds. When the police are after you, you ARE a rule breaker, and rule breaking is cool.

The uncool guy, alternately, is the one who doesn’t break the rules. Here’s what he does wrong:

• Tries to go by the book, unfailingly. I was guilty of this as an uptight 19-year-old manager in charge of maintaining order over a group of 30- and 40-something year old auto shop technicians, many of whom had served in the military or done multi-year stints in prison. I feared anarchy in the shop with the far older and more experienced workers if I did anything other than follow company dictates to the letter... and that made me incredibly lame to them. There’s nothing lamer than the tightwad who insists on following the rules – because oftentimes, the rules do not apply to a certain situation (or, occasionally, any situation), and following them makes no sense. If you can’t deviate, you’re not very attuned to what’s needed, or able to adapt – and, thus, not very cool at all.

• Respects authority too much. A healthy respect for authority is good for learning, and necessary for self-preservation. Yet, those who toe the party line aren’t the ones we look to as “leaders”; they don’t think for themselves, don’t act for themselves, and are too afraid of the consequences to do what needs to be done. Hip-Hop became as popular as it did even among suburban whites in the 1990s because its very foundation is the questioning and challenging and skirting of authorities and their rules; because of this, it became the ultimate “cool” music of its generation... just as rock and roll had been in the generation prior to it, and the tango another generation before. Individuals who are too in love with their authority figures invariably seem extremely uncool.

• Treats others’ boundaries as absolutes. Why do women love bad boys and assholes so much? One of the reasons is that these men ignore women’s arbitrary boundaries and pull them along for an adventure, kicking and screaming if necessary. People who are too cautious of others’ boundaries are uncool. Most people are overly cautious, and KNOW they’re overly cautious; they want someone who will come along and override their weak, fearful protests and drag them off to a life of adventure and excitement and fulfillment. Those who can’t do this are just more of the disappointing same, and not the ones to be counted upon to bring energy and electricity to their existences.

• Fears consequences as big and bad. What happens if that girl rejects you? Or you fail that exam? Or try that thing your boss didn’t want you to try and it blows up in your face just like he told you it would? What happens if you leave it all behind and go travel the world? Or start your own company? Or join a friend’s startup? Might you fail? The uncool individual sacrifices success in order to avoid failure. Because he doesn’t want to be rejected... to fail that exam... to fall into his boss’s targets... to face uncertainty on the road and in his career... he doesn’t do these things. And because of that, mounds and mounds of amazing, incredibly, unconventionally good things that he could have in his life he will never have. People want to be around those who are constant sources of fresh inspiration, success, and opportunity – not the ones who stay stagnant in the same stale places day after day, month after month, and year after year. Not remotely cool.
  

The uncool person is operating from a paradigm of fear and avoidance:

1. I’ll go by the book, and even if something goes wrong it won’t be my fault
2. I’ll respect authority, and thereby not get on their bad side and get hurt
3. I’ll respect others’ boundaries, so as to not invoke their anger and dislike
   
4. I’ll avoid taking risks, because the chance of bad outweighs that of good
   

The cool person, on the other hand, operates from a paradigm of pursuit and endeavor:

1. I’ll do what seems like is needed, and if I’m wrong deal with the consequences
2. If authority is wrong, it does not deserve my respect or submission
   
3. If people are living fearfully, it’s my duty to challenge their boundaries
   
4. I’ll embrace risks, because without these I can’t grow; I can handle setbacks
   

What’s the mindset difference?

• The uncool person avoids responsibility by hiding behind rules, regulations, boundaries, and authority to escape any blame or dislike if things don’t work out

• The cool person accepts responsibility by forging his own path, and disobeying rules, regulations, boundaries, and authorities he thinks are foolish, outmoded, or misguided
  

This is mainly a difference of fear – fear of the consequences if the rules are not stuck to. The uncool person views every potential rule breakage as a VERY SERIOUS, very big, deal.

The cool person views the consequences of rule breakage as “nothing I can’t handle.”

You could boil this down to “confidence”, or perhaps to “competence” – the cool person figures he can deal with whatever the consequences are, and in any event the opportunities far outweigh them – while the uncool person fears those consequences, looks at the potential rewards, and says, “It’s just not worth it.”

Again, very often, this “lack of confidence” or “competence” on the uncool person’s part is simply a lack of realistic assessment of risks vs. rewards – because he’s never tasted the rewards of breaking rules like this, they aren’t “real” to him, and he’s ascribing outsize significance to negative consequences of being caught breaking the rules or breaking them and having things turn out poorly, and not accurately gauging the fruits of the rewards, should he break the rules and meet success.

The only way to get a more accurate gauge is for him to swallow his fear, break the rules, and go after the end goal he desires, and experience what it’s like to get it, and get a taste for what both the punishments and the rewards are for breaking the rules, first hand. The punishments are hardly ever as bad as imagined... while the rewards are frequently far more satisfying than they were imagined to be.

You Are Now a Cool Cat

I’ve just handed you every tool you need to be cool.

You now know that you need to:

1. Always provide value; never only take it

2. Remain cool and unflappable; always in control

3. Stick to the Law of Least Effort religiously

4. Break the rules at least some of the time

The most challenging aspects here will be the mindset shifts. If you can make these, and align your own thoughts with those of “cool” individuals, you will have a pretty straight path to becoming cool.

The good news is, I think these should mostly all be pretty intuitive shifts to make once you have them pointed out to you – they’re things you mostly were somewhat aware you probably should’ve been doing before anyway, but when you see them stated plainly the effect is stronger and more visceral than just a gut-level instinct that you might want to switch things up from how you’ve been doing them.

The really good news is that almost nobody knows this stuff fully and completely consciously... nobody. You will never catch anybody else talking about this. You’ll come across bits and pieces of it here and there, perhaps scattered across the Internet, but these are just various people rubbing away their looking hole into a dust-caked window of the House of Cool. Instead of giving you a peephole to look through, I’ve just unlocked the front door for you so you can walk in and make yourself at home.

What this means, of course, is that you can take “cool” to a level that no one else around you has taken it. Because even among the very cool, these rules and mindset differences are still mostly subconscious, and the subconscious desire to “be cool” is routinely overridden in various situations by various other internal motivations. The only way you become consistently extremely cool is by becoming so completely dedicated to following your gut instincts that you never stray from the course... or, by elevating your understanding of cool to a level of consciousness that allows you to follow it at all times, by implementing rules, and being mindful of what you must do and why you must do it.

It’s not easy being cool.

Once you’ve got it down though, the world is at your feet, because “cool” (trendy as the term itself might be in English right now) is and always has been the very pinnacle of what we admire as men.

Yours,
Chase Amante