What is “coolness”?
Words are tricky. This philosopher guy, Derrida, once pointed out that words and ideas are all attached to one another like a big web or network, but the web itself is attached to nothing. The word/idea “rock” has nothing do with an actual lump of minerals, except in our collective memory. The whole mass of meaning floats. There’s no anchor.
So when I say “coolness,” we’ll have to at least take a second to figure out what I might mean.
No culture worships this quality more ardently than ours in the US. The vast majority of our cultural icons embody it – figures emblematic of wild West lore, gangster lore, entertainment industry lore, and so on. John Wayne. Al Capone. Drake? We foist coolness on famous figures who eschewed it in real life, like Einstein or Lincoln, and even on certain animals like panthers or falcons.
Coolness is an aura of infallibility that rebuffs any weakness – including 
insecurity, confusion, or dependence that makes one vulnerable. Coolness implies the individual is a source, a sun of personal charisma. Even alienated characters, if they’re cool, attract the audience who “gets” them, just as each peer group defines its own style of cool. Across the board, though, cool figures exude confidence – an immunity to bungling, embarrassment, and indecision that elevates them in the eyes of others.
But because words float around, we sometimes conflate coolness with positivity. In conversation, we use “cool!” as a synonym for laudable, so we might potentially mix it up with goodness. However, there’s a world of difference. Take Mother Teresa for instance: what she did in Calcutta was “really cool,” but did she embody any of the “coolness” described above? Would Kanye West rap about her? Not exactly.
Alcoholics often drink to feel cool. At least, as a practicing alcoholic, I did. And you know what? I succeeded with flying colors – again, and again, and again – in my own mind. Of the thousands of drinks I took, the only one that failed to cool-ify me… was my last.
Today, when I try to go back mentally and recreate that sense of “coolness,” what I arrive at is a sense of a force field, a glow of indifference highlighting me as subtly superior. Louisa with a few drinks in her was undaunted by whatever (imagined) disapproval mainstream dolts cast her way. Fuck ’em! Some part of me watched myself and approved, finding ways to make you think I didn’t care what you thought.
Shitfaced, I was even cooler. I became a rugged individual, a Rambo against social decorum, yet slinky and wily, sorta like Catwoman. Your cool may differ. Yet whether boisterous or aloof, we all seek the same sense of impervious, indifferent badassery – a condescending dismissal of the humanity around us. We’re keen. We’re cocky. We know shit.
But all we’ve done, in reality, is swallow some liquid.
Sobriety, on the other hand, demands rigorous honesty. People who cannot recover are “constitutionally incapable of being honest with themselves.” In my eyes, coolness comes down to a form of inner dishonesty which, for us, can be lethal. The friends I see struggling most in AA – the ones who keep relapsing, almost dying, or who eventually do die – are the ones I sense still worshipping this false god.
As hard as it may seem, rigorous honesty means giving up the illusion of coolness. It means ceasing to worship at that altar, unmasking that ideal as empty and pointless. It means grasping and accepting that everyone – not just us, but everyone – is fallible, vulnerable, incomplete, and often scared. Sure, some people with emotional defenses close their minds to these flaws, but they still suffer them, and to the degree that they deny them, they will never find peace.
To be human is to not know what the fuck you’re doing at least half the time. It’s struggling with worry and insecurity, wanting to be liked even when you don’t want to. It’s meaning well, but having stuff not work out, and looking stupid. We’re vulnerable, fragile, and frequently lost. Coolness pretends to banish all this – but it lies.
To be human, fundamentally, is to be incomplete. We are each of us a tiny bubble of life, 
broken off from a greater source that is living-ness, the whole of god. Being isolated is painful. It’s hard to be sealed off in our yardage of skin, encapsulated in our lonely skulls – because our true essence is we. God is we – the manifold of all beings. For this reason, what fuels us most is connection to others – compassion, collaboration, love – not in our glory, but in our humbleness – our simplest human state.
Those who can’t stay sober – many are trying to worship both gods: the god of love and the god of “fuck off, bitches.” Some are addicted to imagined admiration, but most are simply grasping for a life-ring. A few still glorify partying as a form of rebellion: “Fuck, yeah, we gonna rip it up tonight!” (meaning they’re going to ingest things). Others retreat into the cool of morose isolation, of just not giving a shit.
The antithesis of coolness is caring deeply. That means we do give a shit about what matters, including others’ welfare. We’re forever working toward something constructive, remaining true even when the going gets tough. For me, the source that loans me the power to care passionately is god. I have enough; I can take a risk and reach toward you. Ironically, the more we renounce coolness, the greater our capacity to generate acts of goodness that could be deemed “cool.”
Only when I acknowledge that I’m not an island, when I admit to god all the weaknesses and wounds my ego denies, do I open myself to a loving power that completes me, rather than the drink that only seems to. Love – that energy we can pass on in a thousand forms, not of coolness, but of warmth – is ultimately the power that keeps us sober.
A Spiritual Evolution 