You Have No Idea What You Did Last Summer

I take a guarded approach with my personally owned work laptop. The base OS X system sees little direct use and frequent patching. Most of the actual activity occurs within a contained Windows or Linux virtual machine which I subject to an amnesiac’s regime.

Few factors contribute more strongly to an operating environment’s security health than its longevity. The greater its age, the more temporal attack surface it has accumulated, and thus the more likely something sneaky and malicious has burrowed into it.

Thus with some regularity I reset each virtual machine to its latest snapshot, apply all of the security patches that arrived in the interim, and then take a fresh snapshot before using it, repeating this cycle in perpetuity. In doing so I rewind its subjective experience of time to a state of relative purity, wiping away all of the foolish indiscretions and callous victimizations, and then imbue it with the collective wisdom distilled from the planet’s countless intervening cyber atrocities.

How simultaneously beautiful and horrific an act of brain surgery — the stuff of fantasy and horror alike given one’s mood in the moment. How surreal and inhuman to navigate the world with so much accumulated knowledge and yet so little baggage.

Somebody Set Us Up The Blank Slate

We cannot as yet quite do this as humans but there exist some variations on the theme…

Genetic Heritage

Here we each receive a hodgepodge of not just “lessons” but also “theories” that we are to treat as truth.

The “lessons” represent an unbroken chain of billions of years of ancestors who successfully navigated myriad trials, tribulations, and traumas. We benefit from all these teachings, assuming their continued pertinence, without the torment of nightmares about murder, rape, plunder, torture, exploitation, starvation, and betrayal.

The “theories”, meanwhile, represent time-inverted lessons, the confluence of semi-random recombinations and mutations, tweaks to code books that our ribosome factories blindly accept as truth when actually they represent mere guesses. Any of them may prove innovative stroke of genius, suicidally careless blunder, or pointless but amusing variation. Only time will tell.

In one particularly brutal sense a central purpose of each of our lives, as both individuals and within multiple tiers and kinds of social constructs, is to test a collection of hypotheses — some ancient for ongoing relevance and others new for useful innovation.

Artifacts and Mentorship

We have a couple of other ways to glean knowledge without the requisite baggage. As much value as they provide, however, they also carry a great risk of tampering and misinterpretation.

Everything is connected and our memetic heritage shapes our reality as much or more as our genetic one. We can engage in this economy through the creation and absorption of artifacts and mentorship. These two avenues differ in their directness and scalability but both offer a means for integrating knowledge with greater efficiency and less baggage than direct experience.

Of course there is no free lunch — the producers are doubtless providing these gifts at least in part as ego-serving signaling, the consumers may fail to operationalize the knowledge for want of context, and the authenticity and correctness may be difficult to validate.

A Tale Of Two Buckets

You will often hear pilots speak of two buckets — a skill bucket and a luck bucket. The former starts out relatively empty and the latter contains a mysterious quantity. In every challenging moment we find ourselves tapping the two, the former being finite in the moment but regenerative and growing over time, the latter having random contents at a given moment and a quasi-finite nature over time (what analysts of all stripes would cast in terms of cumulative risk).

The job of every pilot, and presumably every professional, is to continually navigate the education maze in a risk calibrated manner that strikes the balance between accumulating capability and avoiding unduly life altering mistakes. In paragliding, as with most anything else, there exist means for rapidly accumulating skill while holding accumulated risk at bay — specifically ground handling which you can readily do on your own and SIV which you should do over water under the guidance of a master instructor with a rescue boat at the ready.

Thoughtful and comprehensive training notwithstanding, you will nonetheless find yourself embroiled in weird and (personally) unprecedented situations within non-contrived contexts. To maintain one’s progression in aviation, it seems, is to think with some regularity “wheeeeelllllp — didn’t know that could happen!”. Hopefully in any such situation you are carrying margins wide enough that the incident proves merely an eye-opening scare as opposed to an expensive object lesson.

And yet even when a dust-up proves physically inexpensive the psychological wounds may prove subtly costly. You will thus also hear pilots, especially paraglider pilots, speak of “fear injuries”. There exist precious few activities so intensely psychological and it takes only a single severe loss of control to profoundly rewire your brain in a way that transforms your relationship with the sport.

My first six months in the sport included three serious incidents and one shockingly cheap accident. And yet for reasons not entirely clear to me not all brushes with catastrophe are created equal.

For some reason nearly getting dragged off a cliff after a forced landing last November or having a tumultuous tumble down a hill during a botched launch in January didn’t really phase me. They were terrifying in the moment but I gleaned what knowledge I could, vowed never to repeat such a mistake, boxed the experience up, and moved on.

My March incident, in which a large asymmetric deflation progressed into a violent spiral and from there to (I guess) a haphazard wingover to (I presume) a partial stall and (I gather) enormous subsequent surge and epic brake check and then a desperate steep turn to avoid pancaking on a berm, was somehow different. Even though I somehow managed to hold things together well enough to get my ass out of the fire unburnt physically I can now, with the benefit of hindsight, see I had sustained a serious fear injury.

And zooming farther out I can see how that fear injury played into over-compensation that led to my April accident in which getting boosted by a strong thermal triggered an overly aggressive brake input which led to a low altitude stall and subsequent ground strike. The concussion I sustained was relatively trivial in the grand scheme of things, mild enough that it had sorted itself out in a few weeks. The resultant fear injury, however, still profoundly shapes my aviation reality.

Eight months, three SIV clinics, 100+ hours of ground handling, and a handful of mountain flights later, I have experienced zero additional serious events and feel like a dramatically more competent and safe pilot. My decision making around when, where, and how to fly is far more judicious, I have a much deeper foundation of skills on which to rely when the universe throws me a curveball, and I sport a far richer collection of regular activities that provide alternatives to how I might spend my time when the aviation stars are inadequately aligned.

At least that’s how things look objectively… And yet, weirdly enough, I am arguably a less confident pilot this November than last. Maybe that’s healthy? Hard to say… My log book shows ~80 days of paragliding in the first six months and ~50 in the subsequent six. Is that choosiness being smarter or more timid? To what degree are those the same thing? To what extent does my clean record sheet of late stem from being better at flying versus being “better” at choosing when not to fly?

From Leeroy Jenkins To Grizzled Veteran

All of which has me thinking about my professional trajectory over a quarter century…

Ah, to be the blissfully naive budding programmer, with visions of algorithms and data structures dancing in your head, ensconced in a quiet room and engaged in a solitary battle of wits against some abstract problem armed with a trusty text editor and cantankerous compiler… No customers, colleagues, vendors, managers, or competitors vying to thwart your attempts to stay focused and build something beautiful… Oh how poorly this bears any resemblance to an actual career in Software Engineering, however necessary a foundation it may be.

Or to be the first-pass entrepreneur/intrapreneur fired with the zeal of a grand vision and delightfully unencumbered with the knowledge of all the things that can and will go wrong… I am thinking of the first of my two DoD projects, one I spent over three years building, a system that many described as well ahead of its time and that earned me many accolades. It accomplished some really cool things and inspired others to adopt a similar approach. It also struggled under the weight of every bureaucratic dysfunction you could imagine occurring in a large government agency and suffered from my naivety and impracticality, never really achieving its full potential.

Or to be the engineer slightly older and wiser yet still bursting with energy and optimism… I am thinking of the second of my two DoD projects, a system that after many early struggles eventually got traction, then kept accelerating, in time profoundly transformed a whole way of doing business, and has exhibited enough staying power to still be making a dent in history. Buhhhhhht also one that consumed over seven years of my life, doubtless took a serious toll on my wellbeing, and saw many comrades fall along the way. Success can be sweet and glorious, but also grinding, violent, and costly, requiring years and years of blood, iron, and mud to come to fruition.

Or to be the engineer older still and yet, continually hungry for personal growth, deciding to leave public service for the self-delusion destroying Bridgewater Associates brand vat of acid… I am hard pressed to think of another period in my career when I received more valuable mentorship in service to a bevy of soft skills. Or more painful. I stewed agonizingly in hard realizations about synthesis, practicality, prioritization, escalation, and composure. I wrestled mightily with how to improve where I could and guardrail where I could not. I got multiple chances to pick myself up, dust myself off, and try again. I learned so much about myself specifically and management generally. I cherish the personalized note I received from Ray Dalio in reply to my departing email to the bw_public_goodbyes alias in which he expressed gratitude for how I seemed to have understood the value on offer in the place and made a point of capturing it (as well as playfully ribbed me for my email’s length).

Then there was my adventure in joining a very early stage SecTech start-up as its Chief Architect. If you have any idea what you are signing up to do, you go to a tech start-up with the baseline expectation that you will condense your rate of learning by roughly a factor of 5:1 compared to a typical 8-6 job by working zany hours and observing the company blaze through countless mistakes on fast-forward. Of course, that’s just the average expectation… Sometimes you might even hit the jackpot and pick a start-up that manages to cram five years of start-up into one when all the while your personal life looks like a comet trail of flaming wreckage. Oh boy. The fraction of problems faced by a technology company that are actually technology problems can be shockingly small and it can be extremely difficult to adequately appreciate what those problems are until you’re up to your armpits in swamp sludge.

Lastly there has been the 18 month chapter of contracting with an assortment of start-ups as a solopreneur consultant. This has been incredibly fun and valuable for an assortment of reasons, not least of which is how instructive it has been, especially in the realm of understanding the classes of challenges that are timeless and universal for all nascent businesses. What better way to round out my education before one day taking the plunge of being a co-founder of my own technology product company?

But… I do sometimes wonder about what we give up when we shed our self-delusions. Are we more likely to achieve greatness owing to an ignorance of how long the odds are? Or do you have to understand all the ways things can go wrong and yet be crazy enough to try anyway? I’m not sure what gets you better odds.

Sober Confidence

I find myself presently pondering a comment attached to a recent post in the Paragliding Incident Discussions group on Facebook. Sometimes ignorance and innocence provide us a certain strength and boldness. And yet that obliviousness doubtless also comes at the cost of courting disaster. Experience, meanwhile, can regularly prove a sufficiently cruel teacher that the student feels compelled to give up, and they aren’t necessarily wrong to do so.

And yet I persist, both in aviation and career, in attempting to find a middle path, one optimistic about the boundless possibilities yet tempered by many hard lessons.

I can’t quite get behind aphorisms to the effect of “live as if you were going to die tomorrow”. That sounds a little too non-nuanced for my tastes, a great way to be a failed entrepreneur or a pilot that actually is dead by tomorrow. How about “live like there is a twenty percent chance you’ll be dead in fifteen years”?

I think I might like that as a life philosophy. I’m planning on having a richly rewarding 2022 while accepting that that may include a healthy dose of drama and setbacks.

Life is too short to be cowardly and too precious to be reckless. Finding the balance is left as an exercise to the reader.