How many of our actions are driven by fear of appearing uncool? What immeasurable damage has been wrought on the unsuspecting populace by the insecurities of the powerful few? Our collective quest for coolness, for the perfect at the expense of the good, for victory drives many into unmanageable situations. It’s hard to quantify, but we should at least attempt to examine the dynamic behind it.

What is cool according to current popular culture? It is the ability to win battles and arguments, to demonstrate your professional prowess with ease, to make money, to accumulate followers and admirers, to be full of potential. In our competition obsessed society the greatest sin one can commit is to be considered a loser.  And what is lame, what is loserville? It is to be average, to be comfortable with what one has, to be static, to not seek the levers of power.

It is a sad paradox that the most ambitious and driven among us reach the positions of power in politics, finance, academia – industries that require the best and the brightest – and then something happens to them once they are there: they turn into insecure narcissists. Those that spent a lot of energy getting to the top, once there, spend a lot of energy on maintaining the image of success. It’s a draining, tiresome task. Daily focus is shifted from concentrating on task at hand to watching others watch you. One begins to develop delusions of threat around every corner and assumes a defensive posture as a default attitude. Every human encounter is seen as a potential minefield, every incoming query is interpreted not as a bid for information but as a test of competency, a personal attack, a scheme to undermine. “Why are you adding on your position?” – an uninitiated intern might innocuously and not without a reason ask  a trader whose position is losing money. “He’s questioning my expertise!” – an insecure trader will think to himself. “It’s a dynamic hedge, kid, go get me some coffee” – the trader will say aloud with the hope of putting the matter to rest by way of using industry jargon. With such entrenched mindset any retreat in any argument or discussion is out of the question, because that would require an acknowledgement of a flaw in one’s skillset or premise, and thus be damaging to the image of success. Search for rationalizations, excuses, assigning blame consume even more time and resources that could be spent productively.

When one has achieved some level of expertise and power, the same amount of effort as before fails to bring about the same results; the career trajectory that has been steep in the early years begins to flatten. Daily routine becomes an exercise of pushing against the ceiling: your success will fail to impress, and if you fail – all hell will break lose. To use industry lingo, their situation is becoming negatively convex, a limited upside/unlimited downside kind of scenario. Just look at Rogoff/Reinhart fiasco: if they haven’t made a mistake no one would have heard of them outside their skull and bones society (academia and a few politicians); one mistake – and that’s what they will be remembered for by the entire world for the rest of their careers. But for a driven and ambitious personality it’s tough to switch gears: he keeps doing what he’s always been doing but with no result, and unable to sense a shift in balance. That’s when apathy and resignation kick in; and bad but manageable position/situation deteriorates into a disaster.

But let’s now examine pockets of society where there are secure enough personalities. Those would include people capable of projecting realistic expectations for themselves: Lower class, illegal immigrants, athletes, most of retirees, sport handicappers. Good poker players are another subgroup of those with secure egos, “good” being a key word. The paragons of security are the ones who are not a part of a professional or academic group, everyone who is not employed in a high-pressure, high-pay (or both) environment. Those who do not belong to any exclusive club, any skull and bones society, those uninitiated are not burdened with the constant struggle to maintain good standing of membership, to prove one’s worth, to impress. The only person they have to impress is themselves.

Sir Richard Branson recently gave us all a demonstration of a cool secure personality: dressing in drag and serving passengers of a rival airline after losing a bet. Such ability to acknowledge and accept defeat and to move on is the foundation of a correct play. To harness such skill requires complete negation of self-importance. A guy at the poker table mindful of his appearance and protective of his image, constantly excusing and justifying his strategy to his table neighbors is a bad player. But beware of a 400-pound guy with body odors, receding hairline and a pony tail – he has long given up caring about what you think about him. Guys like him have nothing to prove and no one to impress. Those guys are paragons of security, of mental fortitude. They are there for the game and for the game only. Their only display of vanity is the size of the stack in front of them. By virtue of not giving a damn they free themselves from having to worry about what others think of their game. That’s coolness.