Of Wisdom & Wingsuits

Oh hey... yup, it's me again—here to reflect on the past year (which consists of ~15k words since May 2023) where we unpacked how Deep Dialectics, Cliodynamics, Infinite Games, Pascal's Wager, Ockham's Razor, and Bayesian Probability all go a long way to helping us stay oriented and moored as we navigate the wildly uneven terrain of modernity.

And it's through these cathartic strings of words (call them tokens in 2024) that I'm able to feel remotely grounded as the world goes exponential... from genAI and geopolitics, to the madness of Terrence Howard and tesseracts, to non-ordinary states of consciousness and existential risk. All in the midst of a meaning metacrisis, where formerly trustworthy institutions have cracked or collapsed, and we’re more or less building a full fleet of untested aircraft as we fly them. 

Rather than simply thinking of things as always true or obviously false, we ought to quickly get in the habit of treating things as hypotheses that over time become more or less trustable theorems that, if we're so fortunate, become reliable laws we can collectively count on.

So while we're at it, why not add another analogy to navigate the liberating free-fall that often arises when we delay certainty in favor of Bayesian provisionality–i.e. what it’s actually like to steer through this shaky terrain without losing our minds (or our lives). Perhaps the most familiar example of this kind of deliberately delayed certainty is explored in Alan Watt’s story of the Chinese Farmer (*I highly suggest you invest the 2 minutes before venturing forth).

From losing his horse to then finding a herd of mustangs, to his son breaking his leg that then saves him from an army draft, to his house burning down, only to be rebuilt on higher ground safe from a flood, the simple farmer’s conclusion at each step is always, “good luck, bad luck, who knows?” And at least for me, that's some super resonant territory as we enter Q3 2024.

What's truly worth internalizing? While the internal debate rages on, he keeps on living––unwilling to collapse the world into binary false opposites of good or bad, right or wrong, true or false. Sure, Watts inhabits a unique and unsettling philosophical wilderness, but it’s damn good advice imho!

And unless you’re a Taoist farmer sage yourself, it can be hard to stick with such uncertainty when the going gets tough. We’re reflexively prone to labeling things as good or bad, and spinning up fabulous stories that help to explain exactly why the world is the way it is, or life has happened the way it has. Avoid being the victim, for it its allure will surely signal the end.

We are little more than sophisticated storytelling monkeys. 

But that sentiment, of delaying judgment as long as possible to see how things turn out, is an essential part of learning to “go with the flow,” especially as the ground appears to be shifting under our feet. So let’s build on the parable of the Chinese Farmer and explore what navigating varying degrees of Bayesian uncertainty might look like in a real and practical sense.

We can picture it like jumping out of a plane with a parachute. The free-fall part is the scary but exhilarating stage of Bayesian uncertainty. It's the unnerving stage of "who the fuck knows." Throwing the parachute represents choosing one possibility or the other, and committing to a specific narrative and likely outcome.

In this analogy, we can explore different levels of certainty, from super safe to unreasonably risky. The longer we delay throwing our parachute, the more fun (and dangerous) the experience of surfing the liminal edge of reality becomes. How much of the Chinese Farmer are you willing to embrace when your ass is on the line? We all grapple with this question. Often unconsciously, but make no mistake, it's deeply embedded into the background hum of our daily lives.

Level One: The Tandem Dive

For the tandem dive, we get curious enough about that whole free-thinking Jonathan Livingston Seagull thing, that we decide we'd like to experience flight for ourselves. We question our reliance on familiarity and comfort often enough to leave the solid ground of consensus reality behind, but we're not ready to trust ourselves with pulling it off solo and without support.

This might be akin to asking edgy questions in high school (or Sunday school as it were)... testing the boundaries by questioning authority (e.g. weren’t these so-called noble Founding Fathers hypocrites to preach freedom while owning slaves?). You want to test the boundaries of consensus reality a little, but not enough to shatter your (or your parent's, or preacher's, or peer's) worldview. And crucially, you tend to trust your existing teachers to sort things out for you and get you back to terra firma when footing gets uneasy.

So when it’s finally time to leap, what's there to do?
Not much, really.

Your trusted instructor is strapped to you like a life vest. When you fall out of the plane (i.e. confront consensus reality) it’s equally terrifying and exhilarating. You're instantly forced to consider your own mortality, and the only thing you care about is making sure that instructor throws that damn chute and gets you back to safety as soon as possible.

That’s level one of surfing on reality's edge. You crave freedom but remain terrified of falling...or failing.

And once you’re back on solid ground, you flip through the GoPro pics and search for anyone willing to hear about the adrenaline rush of your courageous leap. Against better judgment, you begin to wonder what it would be like to go back up and do it again...by yourself.

So you log the classroom hours for a solo jump and hop back in the plane. This time, no humiliating trembles of uncertainty. You’re untethered and free as a bird!

Sort of... but not really.

No way a skydive school would stay in business if they relied on folks not choking during their first solo dive. As a deeply ironic Navy SEAL skydiving joke goes, “don’t worry, you’ve got the rest of your life to figure it out!”

This stage of flirting with free-fall might be akin to the kid who studies existential philosophy and decolonial Marxism in college. Grows his hair long. Gets a few tattoos. Dresses in black. Tacks the obligatory Che Guevara poster up on his bedroom wall.

I certainly had my #questionauthority phase of punk rock, free-falls, and grilling my parents at Christmas about their capitulation to the capitalist (and catholic) machine. But fear not, after a few aimless years following Phish (or ski bumming in Vail) after graduation, the rebel gets his haircut, tries on a suit, and lands a job selling insurance. 

So while you, the college radical, might’ve thought you were fully independent, in reality there was a static line connecting the plane to your backpack the whole time. All you had to do was fall out, and that line made damn sure your chute ripped out above you and carried you back to safety.

Level Two: The Solo Dive

You might have imagined you were flying free, but the tether of student debt, a soul-sucking desk job, and a mortgage payment was waiting for you all along.

First challenge is to jump, but if you resent that leash and crave even more raw reality, you can push further into the unknown.

You learn to do away with the static line, throw your own chute, and stick your own landings. You might even abandon the safety of 10k feet to figure it out, and start jumping from bluffs and bridges. This phase would be akin to radical religious/philosophical inquiry. Almost no one gets to this level casually, or without serious commitment to extended mentorship and risk management.

Taking monastic vows and going into a retreat, diving deep into float tanks and psychedelics (a la John C. Lilly), charting weird and wild transhumanist possibilities in the realm of the AI Singularity. Yup, that's all a likely analogous version of the solo, detethered dive. 

Level Three: Reality's Edge

No instructor to strap yourself to; no static line or rip cord to pull if you get too nervous. You’re 100% responsible for keeping your wits and living another day to tell the tale. Serious shit, but surely exhilarating if you can put in the training and pull it off. And to be clear, level 3 and beyond is uncharted territory for me and most of the people I know. I assume it VERY unlikely, but please lmk if you feel you've ventured into these un(der)chartered waters.

Until one day, even that gets less interesting and you find yourself sliding into a wingsuit (an experience confined to elite athletes who happened to lock up a Red Bull sponsorship back when they literally and figuratively gave you wings). 

This isn't a linear jump from level 3 to 4. This is some level 10+ shit. The whole calculus gets turned upside down. Rather than trying to throw your parachute to return to the safety of consensus reality, you delay that fateful moment as long as possible. This is 100% taking the Red Pill and jumping into the TAZ. If this reality is true, then nothing else before it was as real or has meaning; a full and committed step into the untethered multiverse. 

You surf the literal and metaphoric edge of mountains and forests, skimming the world as it rushes past you. (what’s known as “proximity flying”). This, by all accounts of those who partake, is the heroin of action sports and liminality surfing.

Such a pure rush, so raw, so real that nothing else feels remotely interesting once you’ve tried it. Unfortunately, it has a less than appealing survival rate for even the best who attempt it. Less than 1% of 1% of humans ever make it here. Few of those who do die of old age. Look no further than Dean Potter, one of the preeminent extreme athletes of his generation who ultimately clipped a wing in Yosemite. 

And many more have rolled those dice and come up snake eyes before and since.

In the ontological version, this is where you’ve taken that Chinese farmer’s “good luck, bad luck, who knows?” to the extreme. It’s the community and terrain the McKenna's so aptly termed, The Brotherhood of the Screaming Abyss.

Few who peer over the edge make it back unchanged.

It's what Robert Anton Wilson called, the place where nothing is true, and everything is permitted––the Chapel Perilous, which has since become a meme in the psychonaut tribe to reflect the infinite hall of mirrors of hyperspace.

“One who has entered the Chapel Perilous,” Wilson warns, “returns one of two things: insane, or agnostic!”

It’s encapsulated in the final, near perfect ending to one of the greatest albums of all time, Dark Side of the Moon:

All that you touch
And all that you see
All that you taste
All you feel
And all that you love
And all that you hate
All you distrust
All you save
And all that you give
And all that you deal
And all that you buy
Beg, borrow or steal
And all you create
And all you destroy
And all that you do
And all that you say
And all that you eat
And everyone you meet 
And all that you slight
And everyone you fight
And all that is now
And all that is gone
And all that's to come
And everything under the sun is in tune
But the sun is eclipsed by the moon

Not at all surprising how things went for their lead guitarist, Syd Barrett who reached for the deep dark secret a bit too soon. Barrett, by all accounts, was an ontological wingsuiter to the bitter end.

Which is how we land at Level Four: True Uncertainty

Staying in the wild and wonderful world of not knowing as long as possible before finally throwing your parachute and touching back down (or not). 

Every survival instinct in your mammalian brain screaming at you to flinch, to cling, to clutch at safety, security, familiarity. But at this stage of the infinite game, you know that to succumb to instinct will be your undoing. It's a full Hunter S.Thompson exploration of the mirrorverse. 

But if you can avoid the flinch, not clutch, then you can do something that mere mortals have only dreamed of. You too can fly. Not like a lycra squirrel in a wingsuit, or even an enlightened seagull, but like a god.

Gaining full witness to the frothy edge of the quantum foam we all know to be unfolding at the far edge of reality.
A wave? A particle?
Good? Evil?
Right? Wrong?
Out there, beyond the mere binary is a field where a Sufi in a wingsuit once said... I’ll gladly meet you there!

Ok, on to the good stuff...

Taykentots I'm currently snacking on:

• Read: Plurality: The Future of Collaborative Technology & Democracy ⿻ 數位

• Read: Gitcoin 2.0 Whitepaper (Rainbowpaper to come)

• Read: My Lunch with the Prophet (Playerzer0x)

• Watch: Finding The Money (Lightworks)