Circa ~2015, when beginning to fool around in airplanes, I experienced a troubling revelation — I had shit-for-brains when it came to reading maps.

The pervasive availability of real-time turn-by-turn directions on pocket-sized super computers had over many years inexorably atrophied the portion of my brain that twenty years earlier served me well as a pizza delivery boy finding houses in the dark with a paper map. I likewise realized that a lifetime of driving automatic transmission cars had deprived me of a certain practice that would provide the feather touch required to finesse operating the rudder pedals with my feet.

And so I embarked on some cross-training that would benefit both my life generally and this flavor of aviation specifically — I switched to driving a manual transmission car and resolved never again to embark on a road trip of any variety without a clear mental map on how I would get where I was going. I still use and appreciate Google Maps, for sure, but I endeavor to employ it more as a congestion-based routing optimizer than as a mission critical navigation director.

But instead of fast-forwarding to a world where autonomous cars yield an environment where most humans lack the basic skills to operate even terrestrial vehicles never mind airborne ones, let’s go backward…

The Creeping Prevalence Of AI

I could almost laugh, if our gerontocracy weren’t driving a looming crisis, about the degree to which many of our politicians even as late as the latter part of the 2010s held the belief that powerful AIs still existed only in the realms of science fiction and pitch decks. In some cases this obliviousness may have stemmed from a disconnectedness — how many of them eschewed even email as long as they could manage, never mind social media? In other cases, ones where they had direct interactions, the progress proved more subtle and gradual — over a span of fifty years cars evolved from including perhaps a few tens of thousands of of lines of code to likely hundreds of millions, all the while the Machine Learning algorithms powering autonomous vehicles rendering that metric decreasingly meaningful.

Sometimes events dropped like bombshells, as when Deep Blue defeated Kasparov at chess in 1997 or Watson bested Jennings at Jeopardy in 2011, and probably nobody needs reminding of how ChatGPT burst onto the scene earlier this year. More generally, though, a natural reaction to the emergence of various technologies was likely a subtler “ooh — that’s neat” or “huh — I wonder how they do that?”, not “it’s the end of the world as we know it”. Even those subtler moments, though, often presented sea change level demarcations in the progression, most notably when the AI snake began eating its own tail, exemplified by a few moments in particular — the advent of Google Suggest in 2004, the appearance of Facebook’s “Like” button in 2009, and GMail’s integration of Smart Compose in 2019.

Awakening of the general public to the threats that had gradually woven themselves through the fabric of our society would require the weaponization of social media by domestic and foreign powers alike in ways too obvious to ignore as they spilled over into real world consequences. My only hope for any kind of sanity in the upcoming 2024 presidential election centers on LLMs having made Deep Fakery so accessible that people will stop believing anything they read on the Internet.

No, Really, This Time Actually Is Different

In earlier epochs one could readily wave away advances as not representing existential crises for most professionals. In the realms of gaming the majority of us could rest easy on the basis of not having our livelihoods and identities wrapped up in the games of Chess, Jeopardy, Go, Poker, or StarCraft (while still being able to glean useful brain calisthenics from them as hobbies as AI eclipses our abilities in them). In the realms of non-gaming professions the advances generally looked like drudgery eliminating technologies that freed up more time for the main body of work, such as with speech-to-text software liberating medical professionals from laboriously transcribing their notes (though I’m told that it took a while for mainstream systems to stop mis-transcribing “the patient was prepped and draped in the usual fashion” as “the patient was stripped and raped in the usual fashion”).

The emergence of Generative Artificial Intelligences, however, stands poised to upend this order, and the follow-on acts of Artificial General Intelligences further still. “Come now”, we professionals might defensively say, “we’re just going to see things like call centers get automated”, imagining our own disciplines somehow impervious. Well, sure, at first, but with some of the AI craze leveling off almost a year after the release of ChatGPT we would do well do remember a recurring property of our perceptions — we reliably over-estimate progress in the short-term owing to an under-estimation of implementation complexity while simultaneously under-estimating progress in the long-term owing to a failure to comprehend the power of compounding. Today’s call center employees may be next year’s lawyers, the following year’s radiologists, and the subsequent year’s rank-and-file programmers. Meanwhile tomorrow’s AIs will increasingly run atop compute substrates and training sets generated by their cyber-ancestors.

I have been playing with ChatGPT extensively for programming tasks this year in an evolving attempt to ascertain where its strengths and weaknesses lie, both to estimate its impact on our ecosystem generally and to tune my ability to employ it usefully specifically, not just today but also with an eye toward imagining how its technical progression and ecosystem interactions will shape our future. The pithiest way I can summarize its present capabilities in my domain may be that of a high-output yet very high-maintenance junior programmer mashed up with a forgetful and schizophrenic idiot savant from each and every specialty area. Its ability to take highly nuanced and idiomatic conversational language and emit useful chunks of code does truly amaze but it nonetheless increasingly struggles the more integration intensive, architecturally focused, or bleeding edge my areas of exploration and the longer a session continues. For now…

The more I have used the system, though, the more juice I have found I can squeeze out of it already. I am not sure to what degree that apparent improvement over time stems from my own improved prompt engineering (topic selection, chunk sizing, question phrasing), or its improved handling capabilities (richer model, better heuristics, more resources), but I am increasingly finding ways to make this tool work for someone of my archetype (principal/generalist/inventor/integrator), and the implications of this are by turns empowering, fascinating, and terrifying. For my stage and specialization I often find that the reality summarizes as “I know what I want to build, I know the shape and componentry needed, and I’ve even built something vaguely like this before, but I could use just a little bit of help with certain fiddly details to make things happen a faster”, and that last bit is where ChatGPT is saying “I can help, at least a lot of the time, at least enough to be worth the trouble, if only you’re a little bit clever in the way you learned to be with Google twenty years ago”.

That really speaks to the theory that we will see a near-future bifurcation wherein some people attain superpowers while others risk being left behind. Meanwhile we are fostering an unpredictable and potentially soul destroying long-term situation where Generative AI’s output becomes the next iteration of training data for the same kind of systems, a feedback loop in which we lose not just control of our species’ destiny but also our sense of being and purpose. We need to think hard about that. We probably can’t stop AI’s ascendancy but we might find clever ways to ensure that it elevates most people instead of it fomenting our accidentally either committing species-level genocide against ourselves or handing unprecedentedly concentrated power to people whose goals may not align with humanity’s generally.

On The Cultivation Of The Future’s Humans

I feel rather blessed by the timing of my landing in the tech ecosystem. I began programming at a moment when much of what constituted a product or system ran on a single desktop, server, or some combination thereof, with any intervening networking simple enough as (usually) to prove transparent. As we progressed toward and through the knee of the exponential curve of technological development I enjoyed sufficient neuroplasticity to revel in the luxury of absorbing the concepts as they came into existence. How lucky I have been to start with a strong classical grounding in computer science and systems programing (and a love of Emacs) followed by the as-it-emerged gradual and incremental metabolism of such diverse and powerful technologies as…

1. The Internet
2. Version Control (that didn’t suck)
3. Relational Databases (that didn’t blow)
4. Object/Relational Mappers (that I didn’t write myself)
5. Rich Web Applications (that didn’t involve my simulating a Canvas element)
6. Database Migrations As Code
7. Pervasive Cryptography
8. Containerized Application Deployment
9. Microservice Architectures
10. Observability Tooling
11. Software Defined Data Centers
12. Infrastructure As Code
13. Elastically Scalable Systems
14. Public Compute Clouds
15. Machine Learning
16. Skynet Large Language Models

I had already been thinking, before the emergence of ChatGPT, something like — “well, damn yo, but don’t today’s college CS grads have a bewilderingly broad and deep stack to learn, so no wonder they are tempted to be specialists and gravitate toward something as focused as UX or ML…”

Now it’s even worse for today’s junior programmers. ChatGPT is nowhere near being able to construct, debug, and evolve complex systems, but it is quite capable of answering requests like “please generate a snippet of code that solves such-and-such a narrow sub-problem for me”, the result of which I can then massage into a larger context. That is good for Today Me, it’s quite bad for Today Grads, and zooming out I perceive the severing of a clear path from Today’s Grads to Tomorrow’s Seniors that makes me fret for Tomorrow Me specifically and even Today Humanity generally. Waxing ever so slightly hyperbolic — the only people I envy less than the people trying to pick a college major today are the ones who picked a college major four years ago. The road to being an expert is long and we have suddenly knocked out a bridge for many people to get there.

How strange a contrast to a world that existed not so long ago wherein most people could easily spend a whole life working in, if not a single company, then certainly a single career. How bizarre that just thousands of years ago we could expect thousands of years between successive technological ages but now major revolutions are arriving every year or arguably even more frequently as we enter the age of Generative AI.

As a society we need urgently to think hard about labor force participation and the domain of humans. I shudder to think of a future where humans have lost the ability to write, never mind program, for this seems a path where we lose the ability to think. My formative professional years took place at a federal agency that had experienced a sustained hiring freeze between the end of The Cold War and the events of 9/11, the consequence of which (I can see with hindsight) was an irrecoverable loss of continuity which harmed both the mission and the participants. I foresee a looming analogous crisis for our workforce generally if we fail to recognize the risks and act accordingly. The time for proactive remedies is now but the touch must be light, nuanced, open-minded, and far-sighted.

I imagined writing this after finally managing a good night’s sleep upon returning to Utah but now, after failing to materially sleep for five consecutive days, I find myself concluding that the catharsis of writing must precede the release of sleeping. The perfectionist in me will need to accept a reduced scope and quality in the knowledge that I will be returning to this matter for years to come.

Prologue

Saturday 13 May held the promise of a good day. In Utah I was tidying up the garage in preparation for assembling a workbench intended to home my new 3D printer, a project spurred by a desire to print auxiliary parts for my paragliding setup but which I also imagined encouraging me to dabble in robotics again. In Maryland my brother Benjamin was suiting up for a friend’s wedding, an outing with his wife that would be their first recreational adulting in too long amidst the maelstrom of start-up life, dual careers, and raising their young daughter. Our brother James, however, would call us each in turn to deliver dark news that derailed any possibility of normalcy — our sister Jennifer had killed herself.

Jennifer had dropped her dog off with my parents on Thursday, something she had done on many previous occasions when she “needed a break”, but then entered comms blackout all Friday in a way that troubled my mother, and so my parents traveled to her apartment to do a wellness check on Saturday morning. Unable to raise her upon arrival they summoned the police who after entering the apartment did my parents the mercy of not allowing them to enter. Knowing what I do now I shudder at the thought of the un-unsee-able horror my parents would have witnessed had they had a key and entered unilaterally.

The Unfolding Ordeal

On Sunday I booked airfare to Maryland via a Monday/Tuesday redeye flight, imagining an excruciating but logical and incremental procession of ordeals — the clearing of her apartment, a family-only viewing, a public viewing, a funeral, and then a gathering at my parents’ house. That would have followed a logical if agonizing script with which I had been brutally familiarized with the passing of my brother John in late 2019.

On Monday my parents and brother James went to the funeral home to make arrangements. There the director noted that this had proven one of the more difficult cases he had navigated in decades of work and strongly encouraged my family not to view the body. My parents thus made the decision to send Jennifer directly to cremation without viewing her and to have only a funeral with her ashes in an urn on Friday.

Attending to her apartment, meanwhile, kept getting delayed. Tuesday turned into Wednesday and then Thursday. I began to form a clearer picture of her last moments when I was told that the biohazard team needed, among other things, to remove drywall. It would not be until a full week after her funeral that the fully detailed reality crystallized with the confluence of a coroner’s report, a police report, and a bank statement — Jennifer had impulse-purchased a Remington 12 gauge shotgun for a singular purpose on Thursday and then made her dramatic exit with it on Friday.

And so I just stewed for three days until the funeral with no intermediary outlet for my grief. For various reasons I was processing the experience differently than the period between learning of my brother’s death and his funeral — “grief stacking” from the temporal proximity of losing Jennifer to losing John; “grief constipation” from the mechanism of her death robbing me of the ability to process in stages with the facilitating contexts; and a toxic cocktail of confusion and anger owing to the senselessness of it all.

Also, the universe is not above a wholly gratuitous “fuck you” for the lulz, which it saw fit to remind me when I was walking my old neighborhood in Baltimore’s Federal Hill during this stewing period. I snapped a photo that had my 2008-2011 era apartment in view to the left and the Ropewalk Tavern to the right. On a whim I sent the photo to Jim, a kind soul of a bartender I had met there who had since moved to Detroit and with whom I had kept in sporadic contact, receiving a reply the next day.

You always think there will be another chance to see someone until there isn’t.

I saw my sister in person for the last time at my brother’s funeral. I had imagined seeing her over the summer during a happier kind of Maryland sojourn. Fortune favors the proactive, I missed that shot, and there are no do-overs.

At the funeral a long-time family friend and in particular a close friend of Jennifer, Heather Brown, gave the eulogy. This proved the best and, arguably, the only good part of the ceremonial send-off of Jennifer. I’m not sure which matters owed to an explicit decision versus a ball being dropped because it was all too overwhelming but the elements present in John’s funeral were in large measure missing from Jennifer’s. Not only was her body not fit to be viewed but for some reason there wasn’t even a picture at the ceremony. There was just an urn and three vases of flowers. No symbolic closing of a coffin, no symbolic lifting of a coffin by the remaining siblings into a hearse as we had done with John, no group embrace by those siblings at a central and logical moment, nothing of the sort, some of which seemed unavoidable, some of which seemed an oversight…

The most surreal fail came at the end. When I asked my parents what they wanted done with the flowers and in which car the urn should go the funeral director interceded to note that in fact the urn was only a temporary one for the funeral. He then proceeded to take a coffee-grounds sized bag containing my sisters ashes out of the urn, place it in a slightly larger cloth one that resembled a miniature version of a reusable grocery bag, and then look at my family expectantly. Everyone had a deer-in-headlights moment and then turned wordlessly to look beseechingly at me. And so I picked up the bag, carefully cradled it to my sternum, and took it out to my parents’ car, noting that the heft of what remained of Jennifer’s 32-year-old corporeal existence must have matched almost exactly what I felt when I carried her similarly as a baby eleven years my junior.

I’m not a religious person but I can appreciate how the institutions thereof have over millennia tuned the rituals around saying a final goodbye to someone. I could have used some of that on that day. Sadly, though, the only thing on offer from the religious officiants present was the tiresome reminder that they believe that anyone who doesn’t accept Jesus during their tenure on this planet has the eternal torture of the fires of hell as their next and only waypoint. Read the room, bro — anyone who made their exit in this manner was already somehow experiencing hell on earth.

In addition to blocking on the biohazard team completing their work, our entry of Jennifer’s apartment also hinged on sorting through an executorship establishment workflow, finally culminating in my father entering her place on the Monday after her funeral to do a survey with the idea being that the moving work would happen on Tuesday. I had intended to help but on Monday evening James called me to let me know that my presence would be redundant as there would be no heavy-lifting to be done and really pretty minimal stuff to take altogether owing to the cleaning team having unilaterally thrown away so much of her stuff. I could imagine it having been meaningful and cathartic to pack up her books, maybe to keep a few… but all of them were gone, casualties of the huge blast radius she managed with her final act.

It seemed the universe didn’t want to grant me any manner of meaningful closure with Jennifer in this moment. Finding that will be a long and winding process with no prospect of real completion. I take solace, however, in the silver lining of the trip having included playing chess with my seven year old nephew Joey (son of the late John), employing my juggling skills to make my three year old niece Elli giggle uncontrollably, and getting to spend material time with friends and family I had not seen in too long, even though by the end I was running on adrenaline and fumes with a hard and painful crash imminent (“Introvert’s Death March” I only half-jokingly call such a socialization marathon).

About twenty minutes after greeting this strange Viking she had not seen in ~ 2 years by hiding behind Ben’s legs as if I were the most terrifying thing she had seen in recent memory…

Laura to Dave: “Dave, you have food in your beard again and you really don’t have the excuse that Andrew does.”

An Ominous Background

Thirty two appears statistically to be an inauspicious age for my sibling cohort. It was at that age that I, the eldest of five, had a rock climbing fall…

… whose follow-on MRIs would reveal that my near future would include radiation…

… and surgery…

… and being given a month’s worth of Dilaudid, a drug that Matthew Perry described as his favorite in his recent auto-biography, and one that I am pretty sure permanently rewired my brain, making my (wholly successful!) quest never to relapse a daily project wherein I must fill my life to the brim with other things to give such lingering addiction no quarter.

I was lucky to have so much structure, support, and drive that I could always keep those demons at bay but sadly my brother John was not so fortunate. He never quite attained reliable traction in adult life and spent 15 years in an episodic and gradually worsening death spiral of drug addiction that culminated in his 2019 passing with the fentanyl he bought off the street leaving him dead in his car on the side of a city road. When my favorite rock climbing partner passed he was thirty two.

In 2011 I found myself sitting in a locked down unit of a mental hospital, visiting my sister in the aftermath of her first suicide attempt, trying in vain to understand what had sent her down that path. She would make a series of such attempts, some seemingly more serious than others, progressing over the years from swallowing pills, to cutting wrists, to finally shooting herself in the head. She had tattoos reading “Never Again” inked over her shredded wrists but then ignored the memory device and slashed through them during her penultimate episode. Along the way, however, she would also receive an undergraduate degree in psychology, a master’s degree in social work, and just a few months before killing herself a certification in the state of Maryland. They say that nearly all social workers go into the field half to help others and half to figure themselves out. She seemed to be on that path and doing really well in recent times which makes this most recent turn of events all the more shocking and perplexing. When my baby sister passed, so full of promise, she was also thirty two.

Making Sense Of The Senseless

When pondering a death we might more easily end up with feelings of anger in the case of suicide because there appears to be a certain intentionality to it that we may reflexively ascribe to some manner of weakness, selfishness, delusionality, or other flaw.

Worth remembering, though, is that we are meat machines consisting of various organs all of which are prone to numerous faults of mechanical, electrical, or chemical flavors. Would you get angry at someone with a congenital lung or heart defect? Why, then, deem the brain so special, ye Cartesian Dualists?

And we are incredibly stateful machines. How easy it is to protect our egos by looking down on others without understanding all the nuances of the history that brought them to where they are. I, myself, am prone to anxiety and depression, have suffered various outrageous slings and arrows, but somehow have channeled those characteristics and experiences into a career and hobbies that either benefit from them, damp them, or both, and yet I don’t pretend to understand why I managed to be more functional.

Our proclivity toward tidy categories also drives us to take a binary view toward “suicide”. I think, rather, we ought reason in terms of a continuum. Perhaps pulling the trigger of a gun represents a greater intentionality than getting poisoned by badly cut street drugs, but by how much? And how might we differently reason about two brains that each made a decision to pull the trigger of a gun, one with a functional composition of neurotransmitters in place and another with a temporarily horrific imbalance? Who is the “I” or “you” of which we so casually speak?

I personally can’t fathom what people mean when they speak of “free will”. It doesn’t help that when I ask them to define what it means they can’t even do that. After many years of pondering this topic I’m left only with a concept that I will call Locality Of Agency and that exists on a continuum.

Imagine two scenarios involving a spaceship within the gravitational pull of a sun such that no action by the ship causes it to fall into the sun and the crew to perish but in the different scenarios the ship variously does or does not have the fuel to escape the gravity well. In the scenario of inadequate fuel there does not exist Locality Of Agency at the ship and the crew is doomed because the sun is inescapably in charge. In the scenario of adequate fuel there does exist Locality Of Agency at the ship, perhaps even at the captain of the ship, but the captain either does or does not have the skill and/or will to take advantage of that. How do we judge “them”, an amalgam of deterministic particles, when they either succeed or fail? Will we say that they were heroic in one scenario and disgraceful in another?

Perhaps all outcomes in life are just a matter of luck in a game where the die was cast 13.7 billion years ago and we have to wait for this massive and irreducible computer to run its course to know the ending to each story even though every one of them was always going to end the way it did. There is possibly a deep truth to the aphorism that “existence is a prison”. And maybe in that knowledge we can at least have more empathy for others even if we can’t as a practical matter bring ourselves to forgive them.

But don’t worry about me. “Free Will” is my personal favorite delusion. It sure feels like I have it and frankly I don’t have anything better to do with my time than to live life to its fullest. Perhaps the whole conscious experience is essentially like the sensorial smorgasbord of being strapped into a rollercoaster. Good thing I fucking love rollercoasters.

Everything Is Harder Than Anyone Admits

To “Settlers Of Catan” someone will forever be a transitive verb phrase with a very specific meaning in Gibbs family parlance.

I liked the Internet a lot more before Surveillance Capitalism ruined it, turning it into an advertising revenue driven hellscape where we are all obliged to continually publish a self-aggrandizing highlights reel, and where to the extent that we eschew such a lopsided portrayal of our realities The Algorithm will still find a way to weaponize and monetize our content in a manner that fuels record levels of depression, addiction, alienation, and partisanship. I don’t know what complex confluence of factors caused my sister to effect a permanent solution to a temporary problem but it does feel like we have manufactured a world where there is lead in the water, we are all getting slowly poisoned by it in a variety of ways, and probably this was at least part of her story.

So as an exercise in psychological countermeasures and personal integrity I made a video for her, alas crafted too late to help her specifically but nonetheless maybe an example of a way we may at least occasionally engage to inoculate ourselves and others against the worst of the filter-warped cyber-sphere we inhabit…

On the sixth of January in 2022, with a couple of simple sledders at Point Of The Mountain’s southside, I broke an unintended weather-driven one month flying slump that had been increasingly stressing me out but which with the benefit of hindsight I can now see as a blessing in disguise.

I had, you see, found out on the first of January that I had nabbed a slot in a Colombia paragliding tour a couple of weeks hence to which my succession of reactions approximated “yay!” (I get to go!) quickly followed by “fuhhhhhk!” (I haven’t flown in forever!).

I didn’t yet appreciate that a month-long break was just what I needed, a respite from continually rubbing at the wound of a festering fear injury, and I couldn’t yet know that the tour would throughly rekindle a joy I had cruelly lost nine months earlier.

Fast forward to November of 2022. I buy a new wing (Gin Fuse 3 37m) and harness (Advance Impress 4 L). That act feels like a huge milestone, a concrete recommitment to the sport of paragliding, and I’m stoked to take my flying to the next level with fresh gear. Annnnnd then I don’t fly at all in either November or December because the weather was garbage (unless you like skiing!) and a zany end-of-year push with work projects eclipsed what few opportunities to fly existed…

Fast forward to yesterday, the seventh of January in 2023, and I find myself in a different yet all too familiar situation, wondering if I’m going to be headed back to Colombia not just really rusty but also with a bunch of untested gear. The forecast had seemed ideal but after a very brief window first thing in the morning (that I missed!) a thick fog rolled over the hill and then the winds got very strong. As the day played out the conditions stayed crack-a-lackin’ and so when I realized my window was closing I made my way to the bottom of POTM-SS with the thought I would kite up from there and at least get in a simple sledder that would, if nothing else, let me test out basic gear geometry and wing-feel. And so I slogged across a mud and water filled lower parking lot and setup for the slip-and-slide of an only slightly less gross “Training Hill” kite-and-fly.

Eventually, growing weary of the mud-and-slush fest and sensing a continually weakening wind, with low expectations I made one final reverse inflation and went for a launch, with the succession of thought bubbles looking roughly like…

“Man, it would be great to finally get a first flight on my Fuse before leaving for Colombia in a week.”

“Ugh, so much water, slush, and mud.”

“Well, here we go, at least a sledder will let me test some things.”

“Hrm, maybe this will at least be an extended sledder.”

“BWAHAHAHA! Look at all those people down below me.”

“Ok, don’t be an idiot and get blown over the back because your wing has a sink rate to make others jealous.”

“Ok, my wing wants to stay up forever, but I’m getting cold and it would be nice to still feel my feet and hands when I am trying to land.”

There were a few interesting moments…

I recall being toward the west end, staring off into the setting sunset, blurting out “ohhhhhh myyyyy gawwwwwwd” while laughing like an idiot and adopting a stupid grin, followed by an admonition from some part of my brain that felt like “enjoy yourself but don’t bliss out”. In general aviation good practice stipulates “sterile cockpit procedures” when below a certain altitude and/or within a certain distance of an airport. When engaged in “ridge soaring” in free flight you are spending that entire experience within the danger zone and are well advised to be game-face-on the whole time.

On maybe three or four occasions, riding 100′ or more above the next closest pilot, I got slapped by substantial turbulence, punctuation marks amongst what was otherwise butter smooth air. First you feel it, then you hear it, then (if you’re doing it right) you see it. On each such occasion I felt my neck snap backward and my eyes swivel upward, my hands and hips responding before I could consider things consciously and then evolving the approach as I received visual data. On one such occasion I perceived that I had caught my wing wanting to frontal and then saw it snap backward in my field of view. I responded by throwing my hands upward instantly to prevent oscillatory drama. How wonderful to feel that your body and mind are seeking the right data and responding judiciously in a timely fashion.

I never felt fear, per se, just a deep and undivided focus on the task at hand. I know of no other activity so fully absorbing. To fear flying while your feet are on the ground is healthy. To fear it while in the air, though, is debilitating and dangerous, a sign that you need to fix something.

Last year, as I prepared to go to Colombia for the first time, I was full of dread, wondering how I would roll a giant boulder over a hill, wondering if it was even possible. Today I am focused instead on fine tuning an assortment of details. What a difference a year can make.

In times not so long ago, on my Nova Bion 2, I struggled with kite-and-fly scenarios such as the one described. With some regularity I would feel my toes getting tugged off the ground in a not entirely voluntary transition to flight and then I would fail to insinuate myself into the lift band. Yesterday, however, everything just flowed naturally and played awesomely.

What made the difference? Was it a more skilled pilot? A pilot in a better head space? Better gear? Newer gear? Just dumb luck? We don’t get to know. We never get to know. We tell ourselves stories about why things played the way they did but in the end it’s likely all just Narrative Fallacy. Thus ever we struggle in ignorance in all of life’s matters.

Press on anyway…

Today started by aggressively carpe diem’ing the opportunity to catch up with an old friend and intermittent colleague when he reached out in the latest iteration of our playing scheduling tag over the last month.

I claim no rhyme or reason to the exact timing of our our chats but we manage to arrange them roughly every three to six months and today’s rambling and revelatory ninety minutes on the phone while I tidied the house whilst amused by the cats who were amused by the birds who were delighted by the proffered buffet serves as an exemplar of why we keep making the effort.

At some point thereafter I got the idea into my head I ought go play at Alta in the recent dump and found myself with the challenge that the HOA’s plows had not yet reached the driveways of my street. Fuhhhhhhhk… I didn’t imagine that trying to reverse launch my WRX out of the garage directly into a foot of snow qualified as brilliant so had to choose between bailing on skiing or solving the problem myself.

Then, as I’m preparing myself to venture out for some DIY driveway clearing, I have a mild freakout at the thought that maybe someone had been thinking about breaking into my house by way of the sliding glass door in the back…

As it turns out it was just neighborhood friends who do triple duty as cat sitters and paragliding partners in crime doing exactly what I had suggested a couple of days ago when they were going stir crazy while similarly trapped indoors for a blizzard. They had come to my backdoor to see if I wanted to come outside and join them in the frivolity…

Something I had suggested on the basis of having scouted the opportunity a couple of years ago when I was being tortured by snow too plentiful to travel to enjoy…

So now it was decision time and daylight was burning. If there was any chance I might have been tempted to bail out of laziness that was countered by a need to get some exercise, shit any exercise at all, as a marathon EOY push on a contract followed by a blizzard trapping me in the house was causing me to go FUCKING CRAZY, and so…

Keeping an arctic battle tank as a housemate is a bit of a commitment but anybody who has ever said “all good things come to those who wait” never found themselves at risk of missing a skiing day because the contracted snow clearing folks were behind the curve. I love this Honda as much as I loved my last Honda (Accord). After a quick victory lap with The Beast to help a neighbor finish the swing on their own DIY driveway clearing adventure I hopped in my car and sped away…

I’d be lying if I said the skiing conditions were objectively great today. The “powder” on offer reminded me of the wet stuff you get from a fresh dump at Whistler/Blackcomb and the visibility was terrible.

But that’s beside the point even if you account for my being desperate for some outdoor exercise and frivolity. Skiing, much like flying, varies greatly from day to day in its quality and character on the basis of weather conditions. On marginal days you can either stay home and lament that conditions aren’t ideal or you can “go to know” and treat it as an opportunity, among other things, to find some way, by hook or by crook, to grow your library of experiences and repertoire of techniques. Today variously offered “skiing by braille” where you’re ripping over moguls quasi-blindfolded while relying on spinal-cord optimized reflexes (at one point I started singing ominously to keep people away) or “mashed potatoes delight” where you’re managing the competing tensions of “will I make this turn?”, “will viscosity variance make me superman?”, and “will I get marooned in this gully because I chickened out?”. In all cases I strove to recast the experience from an unglamorous suffer-fest to a game of “can I ski this?”.

Maybe one day I’ll get stuck in a Type-III adventure where I have to ski a thing and this deep bedrock of practice, akin to paragliding’s SIV, will save my ass. That seems all the more probable of late as I just purchased my first set of alpine touring gear.

Better to make your mistakes when your life is not (as thoroughly) on the line so that when it is you’ve already practiced the shit out of things…

Unloading at the top of my final chair ride which I boarded just two minutes before last call I heard one hardcore person look at the following chairs and be like — “What is up with all these empty chairs behind us? Do people hate skiing?”. Turning around to see the speaker I saw some badass wearing a full body pink suit whom I don’t know but certainly recognized. “Whoah, people aren’t gonna miss you” some other rando remarked to him regarding his apparel. “Gotta dress like that or have a beard like this if you want to be recognized”, I chimed in.

“So many people posting on Instagram about today but where the fuck are they?” pink suit guy observed. “Coming out just long enough for one shot that they go post from the lodge”, I replied. “Fuckin-A”, pink suit guy agreed as he slid past and fist-bumped me. “You, sir, have the best beard I have seen in all five of the days I have been skiing here” replied the other guy before we all parted ways and I closed out the day with a final High-T run.

Finishing up, sampling the best of “skiing by braille” Alta had to offer, I almost ate it right before getting out of my skis thanks to a large mogul operating in stealth mode just dozens of feet before the parking lot. “What the actual fuck?“, my L5-S1 disc bemoaned in the wake of the bouncy flailing violence.

Then, just as I’m about to leave, some guy, I think his name was “Justin”, be like “whoah, the beard, man I gotta get a picture of that! No, wait, now I gotta get a selfie with it!”

“OK, now make a silly face!”, Justin said. “I’m always making a silly face when I look like this!”, I replied.

Then, just as I think my day is now finally at an end, some random woman walks past and is like “What is going on here? I want in!”…

“OK, now make a silly face!”, Justin said. “We’ve been over this! I’m always making a silly face when I look like this.”, I replied.

As the woman walks away Justin realizes, to his horror, that he didn’t have her AirDrop him the shots she got on her phone that she had AirDrop’d to me, and then when I try to AirDrop them to him my phone can’t see his, so now I find myself doing mountain-side tech support on his phone as he is panicking over the possibility of losing out on the souvenirs of a lifetime…

My quads burning, not just from an afternoon playing in the heavy stuff but exacerbated by having to adopt a “deep lunge” posture just to fit in the group selfies, I made my way back to my car, highly amused by the evolving beard-feel I was experiencing as I progressed through altitude-driven climate variations…

The most extreme of which was the transition to sitting in a car…

What a day bursting full of unexpected joys!

Nothing compares with the tired-but-happy sensation of ending a day like this when your blood feels as if it were infused with warm honey…

I thought today was just Monday but instead it was full of magic and wonders that made me feel connected to the universe.

“Energy management is king.”

At the start of 2021 I tried an approach of enumerating an assortment of focus areas. That had some interesting outcomes and I still keep the list tacked to my refrigerator as a reminder but overall I ended the year disappointed with the strategy. At least I’m reliably eating more vegetables.

At the start of 2022 I opted instead for a single unifying theme captured in a simple phrase: “I will live with fear without living in fear”. Overall, as someone who started the year riddled with doubt and at risk of being scared out of paragliding, I ended up pretty happy with the results. All of the photos in this section would have failed to exist without that commitment to myself and the help of a handful of amazing friends, instructors, and mentors who created opportunities, offered feedback, and graciously tolerated my jitters. Year-ago-Andrew probably didn’t believe that any of this was possible but took a leap of faith anyway and doggedly chased a simple theme.

On the heels of what feels like a successful 2022 I incline toward repeating last year’s approach and so here we go: “Energy management is king”.

I love this approach for two reasons.

Firstly, it provides me something I can easily repeat every day while anchoring my behaviors around it and continually assessing whether I am being honest with myself.

Secondly, it offers me the ability to evolve its focus as the year plays out and I build on earlier successes.

But the power of the theme’s simplicity rests on the assumption that I will expand that macro into concrete actions and sub-philosophies, so here we go…

Some Thinking To Shape The Year

I’ve been doing the solopreneur consultant thing for nearly three years now, starting somewhat by accident when COVID blew up my “sabbatical year” plans in March 2020 and continuing somewhat more deliberately when I decided “I guess this is a thing” about a year later.

It has variously proven wonderful and terrible, occasionally at the same time, though it has always been educational.

Central to that education has a been learning how to deal with a loss of structure.

First, let’s enumerate some bad outcomes I am experiencing:

1. Sluggish getting up many mornings
2. Slow getting to the first productive activity of the day
3. Missing out on certain outdoor activities too often
4. Often feel overwhelmed by All The Things
5. Unreliable motivation for Work Stuff
6. Non-contracted projects languishing or abandoned

Second, some diagnosis of contributing factors:

1. High degree of flexibility when I work
2. Unpredictable readiness of clients for me to do work
3. Easy access to lots of digital distractions
4. A personality that is very momentum driven
5. Inadequate regularity around sleep timing
6. Damaging proximity of sleep disruptive activities to sleep time
7. A very “remote-oriented” reality both personally and professionally
8. Many of my favorite things are very timing- and/or weather-sensitive
9. I have no external back pressures on my house getting messy and disorganized
10. The cyclic/unpredictable nature of my life encourages (non-financial) “debt cycles”

I should also step back and note that certain of these challenges aren’t entirely unique to this epoch but rather merely exacerbated by a mix of biological age and life architecture. I used to do classified work in a SCIF where I could not bring a cell phone and access to the public Internet was cumbersome but even there I struggled with a temptation to look at the firehose of email on the classified network. I used to have a work schedule that expected eighty hours per two week pay period but even if I didn’t flex that with COMP time I was still prone to substantial variations in start time, end time, and day duration. I used to be able to eat, drink, and be merry right up until bedtime but now that causes indigestion and insomnia. BLARGH.

So, yes, some of this stuff is situational, but also some of it is innate, and some of that latter is new-innate. In previous lifetimes I had to adopt life hacks like “no email in the mornings” and “write at least some code everyday”. I’ll have to do similar if I want to do better while also adopting new disciplines that a younger Andrew did not require.

What are some things I can do now to start tipping the scale in my favor? A few sub-themes seem like good places to get traction…

1. Have a consistent dinner time
   • Be more planful about shopping and meal planning
   • Cook a fancy dinner if I have time, but…
   • Always have a break glass option for a quick dinner, and…
   • Eat a much smaller dinner if I botch the timing
2. Have a consistent sleep and wake time
   • Be disciplined about last meal timing
   • Be disciplined about last liquids time
   • Be disciplined about last screen time
   • Take a hot shower right before bed
   • Commit to a specific wake-up time and set an alarm
   • Set a corresponding Chilipad Ooler wake-up temperature schedule
   • Get out of bed immediately when alarm goes off
   • Adjust these parameters gradually throughout the seasons
3. Maintain an orderly house
   • Allocate a daily maintenance budget to recurring matters
   • Allocate a weekly budget to strategic matters
   • Take one day per month to focus just on this
4. Maintain a pain free body
   • Be consistent about putting in the maintenance work for strength and flexibility
   • Be conscious about taking breaks when working to move around the house
   • Be willing to proactively take a break from an activity if I have a chronic injury
   • Resist the temptation to eat until I am full and beyond as comfort
5. Maintain a more consistent amount of “Work Time” per day for structure and momentum
   • Cultivate and sustain personal projects that take up the slack of consulting projects
   • Avoid any personal/leisure usage of digital distractions in the morning
   • Keep phone well outside of arm’s length when attempting to maintain a flow state
   • Cull certain apps from my phone during certain windows to reduce temptation
   • Shape higher value “break” activities to fold into the day (e.g. DuoLingo study time)
   • Have a defined junction time where either outdoor play or indoor work begins
   • Have a consistent routine that leads up this junction point
   • Commit to a “write something every day” discipline with my blog
   • Commit to a “write some code every day” discipline with my suite of tech projects
6. Make decisions that accept uncertainty and then put them out of mind for the time
   • Avoid the anxiety of continually re-considering whether to take on a stressful item
   • Avoid the decision fatigue and churn of trying too hard to optimize outcomes
   • Create certainty by committing to activity start times even when none is required
7. Develop mechanisms to track, measure, and manage related outcomes

Why?

Because as Jocko Willink is tirelessly reminding us “Discipline Equals Freedom”, Freedom means having the capacity to do more of the stuff I love, and both time and energy feel scarce and precious…

So in 2023 — Energy management is king.

In which we explore the likelihood of our imminent demise at the hands of a super AI…

Anybody else get forced to agree to a new Terms Of Service for iCloud just now and actually read them? It’s kind of amazing the Orwellian power we have voluntarily ceded to massive corporations to erase our lives when it suits them.

As our digital histories continually lengthen and the local storage of our personal artifacts fails to keep apace we rely ever increasingly on cloud storage. Certain such cloud providers, meanwhile, may see fit to nuke your existence over content unilaterally and opaquely classified as vaguely and subjectively as “obscene”, “vulgar”, “hateful”, “racially offensive”, or “ethnically offensive”, and if that isn’t worrisome enough even the catch-all “otherwise objectionable”. They can even jam you up on vague claims of IP infringement or NDA violations.

Imagine the scope of such powers in the hands of any of the various stripes of religionism, activism, or other authoritarian thuggery.

As certain flavors of compute become as commoditized as any of the clearly recognized necessities of modern civilized life, such as water, electricity, and fuel, they gain the property of being weaponizable against individuals and populations to exert control, and as a society we must be extremely suspicious of such assumption of power.

Never has it felt more visceral to me that who controls the present controls the past and who controls the past controls the future. It’s not just our ability to post contentious content to social media that is under threat but also our ability to maintain our personal, even private, digital legacy in a world of continually churning public opinion and institutional power.

You might say that I didn’t _have_ to agree to the new terms and, in a narrow technical sense, you are right, but perhaps in a sense similar to someone in a secret detention center not having to sign a confession. These matters are not simple or binary but rather many-faceted and taking on a range of values, the salient higher order properties being leverage and symmetry. As a practical matter there isn’t much a single individual can unilaterally do against a multi-national corporation with a multi-trillion-dollar market cap. Individuals must rally to collectively counter-balance such forces.

It is a grave mistake and a huge distraction to be asking our governments to compel large corporations to rein in the free expression of their users. We should be demanding, instead, that entities who have attained the stature of utility providers adhere to certain guarantees of rights, and rather than looking to censor specific content on tenuous grounds of compliance with the orthodoxy of the day instead be taking an increasingly hard look at the _algorithms_ whose virality platform providers have weaponized for profit in a manner akin to drug dealers and that in turn have been weaponized by the PSYOPS practitioners of all stripes.

In a world where corporations have reached, and in some ways exceeded, the powers of national governments, it is toward them that the gaze of a free citizenry must turn when seeking “to be secure in their persons, houses, papers, and effects, against unreasonable searches and seizures”.

My 2021 New Year’s resolutions took the form of a list of focus areas. I still gaze upon it with some regularity and shape my strivings accordingly. The intervening year, however, shook me to the core and consequently this go around I opted for a single anchoring sentence — “I will live with fear without living in fear”.

A Longer Form Backstory

This narrative, while capable of standing on its own, feels like the fourth logical volume in a larger story wherein the first three installments are here, here, and here.

Hanging By A Thread

In April of 2021 I had a scary paragliding crash that obliterated my confidence and placed me at the beginning of a long journey of recovery even though my physical injuries proved implausibly trivial. By December 2021, despite having done tons of training to become an objectively better pilot, to include receiving generous coaching from Chris Santacroce, completing three SIV clinics with Brad Gunnuscio, and devoting a ton of time to ground handling practice on a much loved wing I acquired from Joey Jarrell, a chronic fear injury persisted.

In the eight months since my mishap the longest flight I had sustained lasted about fifteen minutes, and not for want of opportunity, but rather because that represented what my fear budget could support. The trip to Alaska that Ariel Zlatkovski had suggested before my crash now seemed like preposterously wishful thinking. Although I had found the nerve to fly a few times at The V with Joey’s encouragement and coaching the idea of progressing to Grandeur Peak continued to feel extremely intimidating and, when I was flying, the fun too often tilted toward the Type II variety. Time and again I would show up at POTM-SS and manage my anxiety by just ground handling… for two hours.

Riding the high of my third SIV with Brad in October I signed up to go to Roldanillo for his thermaling clinic in February. Navigating “stall exposure therapy” with him had proven invaluable, leaving me able to actually enjoy deliberately doing the maneuver that I had first experienced by accident and nearly to disastrous effect, but even though the moment was cathartic and rationally I knew I was becoming a much more capable pilot, that glow quickly faded, displaced by a residual fear perpetually lurking in the shadows. Some part of my brain kept seeing Roldanillo as an increasingly intimidating and overly ambitious idea.

Joey suggested that I consider Chris Hunlow’s January thermaling clinic in Piedechinche as a less scary incremental step. I subsequently agonized over a “double down or bail out?” decision point. Finally I worked up the nerve to go for the former option and reached out to Chris on December 3rd… only to find that his clinic was already full. He noted, however, that not everyone was as yet fully committed and so I should keep the faith by maintaining readiness to go, indicating that he was trying to add capacity but that a coincident competition was squeezing local resources. A week later, anxious to know if I might join, I pinged him again but he (quite reasonably and honorably) said he needed to give early registrants a fair chance to finalize their plans. At this point I bared my paragliding soul to him to illustrate what I viewed as the stakes for me and then set to patiently waiting.

As the remaining days of the year ticked down I found myself imagining that Piedechinche represented a forlorn hope and began pondering an option space that seemed to have collapsed to “Roldanillo or bail out?”. A few days before the calendar rolled Brad pinged his group to finalize commitments for Roldanillo and by New Year’s Eve I found myself facing an agonizing choice. For days my finger hovered over the “Send” button of a note to the effect of “sorry, bro — can’t do this” but with the buzzer for 2021 about to sound I instead resolved that “I will live with fear without living in fear” and sent Brad the tuition balance. Roughly twenty four hours later I got a note from Chris saying that although his original tour was completely booked he had managed to scrounge up some extra capacity and a slot was a mine if I wanted it. I accepted immediately and began making plans at once. When I thanked him for making it happen he replied simply — “it was because of your push that you got this spot”.

Pushing Through The Pain

My pre-trip anxiety manifested in my sweating every preparatory detail while Chris exhibited the patience of a saint by answering all the questions I asked promptly, thoughtfully, and exhaustively without exception. The man knows customer service presumably because, among other reasons, empathy ranks high among his super powers. Nonetheless by the time my bags hit the floor of a room at Siga La Vaca one might have summarized my general mind state as “holy shit what the actual fuck am I doing here?”. This trip embodied one of the most extreme manifestations of “fake it til you make it” in my life — stacked atop it being a last ditch leap-of-faith to recover my love for the sport, it also represented my first post-pandemic vacation travel, my first time in South America, my first time paragliding outside of Utah, and a clinic focused on a skill area where I had no proven ability.

On the evening of my arrival the whole group went out for dinner. Chris, perhaps sensing my anxiety, took a seat at the table across from me and provided some extra attention and assurance — “Dude, just have fun; this will be Colombia on easy mode”. He said we would walk the LZ in the morning and that aiming for a simple sledder was a reasonable first-day goal. My nerves were still buzzing but the intensity had dissipated to a manageable level. By force of will I clung to a visualization of what I wanted to be true by trip’s end and kept putting one foot in front of the other.

In Piedechinche your launch faces west which implies a late-ish start to your flying day. Getting to the top of “Seven” after a preliminary walk of the main LZ, I had plenty of time to stew in anxiety. Consequently mindfulness and visualization were key. I set up my gear, dropped my brain into neutral, and waited for my moment. When my turn to setup on launch came I waited for enough of a cycle to reverse inflate and then was off to the races with the expectation of an extended sledder of maybe ten minutes… but that was not to be.

Instead I found the confluence of courage and conditions to have an amazing flight that lasted nearly an hour. Scrounging up the guts to capture thermals by turning 360s close to terrain I found my confidence growing alongside my altitude. The greater my height the less worrisome the turbulence felt. What a moment — that flight would have been magical in its own right but in the larger context of my having spent the preceding nine months too afraid to fly longer than fifteen minutes this represented a joyous conquest of my fears and a renewed sense of hope.

And little did I know that this was just the beginning. I took the next day off because my brain was fried, overwhelmed from the strain of travel, the anxiety of anticipation, the adrenaline of the moment, and the flood of relief having smashed through a barrier. “Don’t be greedy” is a mantra that has served me well.

On the third full day in theater I would strap in again for another flight every bit as excellent as my first one. The jolt I got from this experience was the sense that the first one had not been an irreproducible fluke but rather the first data point that I was onto something — a sense of “I got this” was growing.

The next couple of days proved a rich tapestry of experiences…

On day four I launched either too soon or mistimed to cycles and sunk out with a twelve minute sledder but, seizing the opportunity to exploit the site’s “free refills” I jumped in a truck and immediately returned to the top for another go which proved a hard fight to stay up thirty three minutes in weak and spotty thermals. Reflecting on the second flight later that evening, somewhat down on myself for only flying half as long as as on the previous days, Chris remarked on the adverse conditions of the day and reminded me that it’s not the raw numbers that matter but how well you played the hand you were dealt.

The next day I had a similar quick bomb-out and refill only to find myself seemingly headed for another disappointing sledder, but… I held on by my fingernails and it turned into the best flight of my life thus far. At some point I gave up on milking the weak lift of a ridge and turned toward the LZ, hunting for opportunities but seeing none… until at just about the last possible moment I spied a handful of birds turning together, made it toward them, and then had one of the most focused sustained struggles flying I had ever had. My arms burned as I heard Kevin McGinley shouting over the radio from launch “KEEP WORKING IT!” and I turned and turned and turned, just barely managing to stay in zeroes for what felt like an eternity and then… my dogged persistence paid off when nature delivered, a reminder that 90% of life is just showing up (the “showing up” in 4-D space admittedly being tricky). Perhaps the most magical moment occurred when I realized that other pilots were forming a gaggle around me in the thermal I had figured out in the middle of a flight that broke my records for duration, climb, challenge, and all around fun.

All that aside, a much higher order phenomenon coalesced… At some point during this flight I experienced a feeling akin to the big meaty clunk of a safe’s locking tumblers aligning and the door swinging open. I finally felt awash in a serene joy that had gone completely missing over the previous nine months and at a level perhaps never previously attained. I was flying alongside the clouds above a strange and beautiful land, the thermaling skills letting me get there and the SIV training providing the confidence that with so much altitude I could handle anything nature threw at me. I could relax and drink in the preposterous surreality and beauty. I had burst through the end of one of the longest and darkest tunnels I had ever navigated and the reward tasted incomparably sweet.

The next couple of days offered marginal conditions and I only managed to eke out a simple sledder on each day. I might have tried to fly more but that would have been folly and the terrifying experiences some pilots outside of our group had made me confident in the wisdom of my conservative choices.

On what was to be my last full day in Piedechinche I called the airline and doubled my odds of having another awesome flight by extending by a day. Then I went to the mountains and smashed my personal best for longest flight by a factor of two, flying for just shy of three hours. My log book records only two words for the flight: “holy shit”. The ayvri track would seem to reveal something vaguely resembling an improvised mini-XC triangle. I think the trick to success involved this being the one day on the trip when I forgot to deploy my water tube. In any case, it’s just as well that I wrapped at three hours as my brain was melting and it’s a good idea to have some operable neurons at the LZ.

The next day I had to laugh at the absurdity of my final flight — what now counted as mild disappointment was “only” flying for four times as long as any of my pre-PDC flights over the preceding nine months. What a difference a week can make! My heart left Colombia and flew back to Utah bursting with gratitude and a renewed sense of possibility.

By the time I was returning to Colombia three weeks later for round two in Roldanillo with Brad I felt far better prepared to navigate the attendant challenges and wring optimal value from my time there with him. There the air proved gnarlier, the cloud base more complex, the terrain more committing, and the schedule more stringent… but instead of feeling behind the curve on basic thermaling technique and intimidated by rowdy air and massive power lines I could begin to focus more in earnest on the mechanics of XC flying which were plenty difficult on their own.

All of my landings were “fine” though certainly some were more elegant than others — on my first flight, concluding in a landing immediately adjacent to some towering sugarcane, having an extra tall friend made all the difference; during my most chill landing I didn’t adequately consider how I was going to get out of a fenced in field; on my final flight I partook of a rather more intimate tour of a vineyard than I might have preferred.

This last landing pictured above was from my final flight where perhaps the standout lesson was to be far more certain of having glide to my desired LZ. I hedged my bets in a way where nothing catastrophic was apt to happen but the price of that insurance policy was a sufficiently indirect route that I just missed the subsequent field and nice road I had intended to make my landing spot. Whoops. I landed perpendicular to the vineyard rows, saw my wing fall sideways into the plants, and groaned “argh — not again!”.

Only one of my flights, on the penultimate day, would I file under “arguably a really bad decision” but even that was highly educational in its own right and it proved a “cheap lesson” — ain’t nothing like cramping up from holding in speed bar while listening to your vario’s sink tones for the whole flight as you wonder if you’ll clear the various power lines along the way and make the LZ despite beelining to goal the whole time. Be wary of allowing far off good looking clouds to tempt you into a “Bridge Too Far” kind of ordeal.

The Fickleness Of Recovery

I have been driving for twenty six years and half way through that time I had my first and only at-fault accident. The car in front of me took its crack at the scary launch required to make a right turn from a spur road with a terrible sight line onto a rightward curving state highway so I looked over my shoulder to do the same, let off the brake, and… CRUNCH. Actually the car in front of me had balked at the last possible moment and I rear-ended them at maybe 1MPH. I was mortified. I was also in denial — it felt like the universe had played some horrible cognitive trick on me (probably in the form of leaving me hangry and dehydrated after a vigorous summer volleyball game in a poorly ventilated warehouse). And most interestingly I completely lost confidence in my ability to drive… for about two days. Presumably the extreme brevity of this confidence interlude owed to a huge reservoir of historical positive/unremarkable experiences and a subsequent return to daily driving.

My flying reality has offered a much more challenging progression. About five months into things I had a terrifying experience with a big asymmetric deflation that I just managed to navigate in a way that narrowly avoided it yielding my curtain call by way of high energy pancake. Shaken by this I found myself unknowingly on a deflation-to-stall arc wherein reactive and excessive brake pressure to guard against another deflation put me in the danger zone for a stall just in time for the unfamiliarly strong thermic conditions of Spring in Utah. This time I would prove less lucky, pounding into the ground and taking an ambulance ride to a trauma clinic, though somehow with an unknown combination of mitigating factors limiting my injuries to a mild concussion, a tender upper back and neck, and the jaw pain that probably indicated my helmet strap had done its level best to save my life. The doctors marveled at their inability to find anything at all in my full-body CT scan given the accident reports bystanders had offered. How did I get off so cheaply (at least physically)? Technical skill, physical toughness, sang-froid, or dumb luck, and in what proportions? The concussion wiped most of my memory, witness testimony was inconsistent and incomplete, and there was no video documentation, so it remains forever a mystery. I have had people tell me that that is a gift but given the subsequent journey I’m not entirely sure.

Over-compensation from incident to accident doubtless served as one major factor in ending up in a bad way. A relatively short flying career meant I had a fairly small amount of accumulated positive experiences to damp the negative ones. And a concussion mandated timeout of about a month gave me lots of time to stew in negative thoughts. All in all a perfect storm to engender a crisis of confidence, one whose challenges would take a long time to surmount, and the ghosts of which still haunt me in a way that takes a disciplined approach to overcome…

After returning from Colombia round #2, having handled everything that beautiful country had thrown at me, never suffering more than a tiny tip collapse at any time despite occasionally quite rowdy conditions, I found myself harboring a restored confidence. Again, however, it proved fleeting in the wake of subsequent challenges. Between a couple of bad weeks of weather followed by a mysterious knee injury that left me unable to fly for about six weeks I unexpectedly had two months to lose momentum and confidence.

I knew my subjective reality was ridiculous given what a huge collection of challenges I had navigated successfully in the previous year and yet there it was. I seem to be learning that, for my subjective self anyway, highly negative experiences exhibit a long half-life, highly positive experiences offer a much shorter half-life, and I furthermore (or perhaps consequently?) demonstrate a strong recency bias.

This implies that I must consistently accumulate positive experiences to maintain momentum. When I find myself at the end of a travel paragliding experience I am hungry to fly. If a few weeks pass without any flying my confidence begins to flag and I find myself subconsciously generating excuses why today is not a good day to fly. Notably all of these problems melt away once I am airborne and I dial into that incomparable sense of Flow that aviation brings. The struggle, rather, involves simply showing up.

Finally, after a two month flying drought, and on release from my physical therapist, I had a delightful POTM-SS flight. It was simple but joyous to be back, just a 15 minute ridge soaring session, but just what I needed to get back in the game (a hug from Jimbo and Mark probably didn’t hurt either). I was, mind you, terrified that my knee was going to explode on landing, and I had to yell at myself to stay gentle on the brakes during short final while some of my brain was incorrectly screaming “LET’S SLOW DOWN”, but happily I came in with lots of energy and flared at just the right moment and all was well. Phew.

Then on my next outing, also at POTM-SS, just as I was packing up to leave I witnessed a midair collision and ended up being a first responder. One pilot was fine and another was in very bad shape, face down and not moving when I arrived shortly after other folks. I wasn’t sure how much help I could be with several people already on-site but actually the answer was “quite a lot” because I seem to be much calmer and more rational than the general population when navigating such crises. When I realized that he was still hooked to his wing I designated someone to sit on it lest it repower. When people wanted to roll the pilot over to take off his harness I argued strenuously and successfully that we not do that so as to protect his spine. As the situation developed I asked emergency personnel whether they intended evacuation by ground or air so that if it was the latter we could start to clear the field aggressively. By the end I was glad I had gotten involved but… I was also shaking and having to work hard not to cry or vomit. This pilot’s crash site was almost identical to my own from just a year earlier.

The next time I was clipping into my harness, this time at POTM-NS, I witnessed another pilot attempting a top-landing take a massive deflation that set off a cascading series of failures. I held my breath as she proceeded from big asymmetric collapse to spin to stall to surge to re-stall and… I breathed an arguably somewhat premature sigh of relief when she appeared to transition to back-fly (or something similarly forgiving; I was far away) just before impact which meant she hit the ground at maybe the speed of coming down under a reserve parachute. I imagined that this eerily resembled what spectators got to watch during my own stall once upon a time and that my margins between something relatively benign and something horrific were similarly slim. Blergh.

With my confidence taking hit after hit from things that actually had nothing directly to do with my own flying performance I had the sinking feeling that all my hard won successes were slipping between my fingers.

Ever Onward And Upward

I am, however, if nothing else, persistent, and furthermore blessed with some excellent friends that are continually creating opportunities for me to succeed. So when Ariel re-raised the idea of coming to Alaska I jumped at the opportunity. Well, just as soon a I figured wheels to rent that weren’t going to cost ~$6000 for ~2 weeks that is…

With those plans finalized, though, I had three weeks to fill and was hungry for something to boost my aviating spirits. After talking about doing it forever, and with repeated nudges from Joe Hastings to consider it, I finally did my first ever legit hike-and-fly, braving Grandeur Peak in what turned into a race against time to launch before the wind wend katabatic. We started the hike later than ideal, I forgot to grab my trekking poles before we left the LZ for a nearby staging area in Joe’s car, I strained against ~60lbs of gear that had me grinding at target heart rate for the whole ascent, I nearly had my helmet roll down the hill while I was laying out my wing, I squandered precious moments on an ill-fated reverse inflation as the wind was reversing, and by the time I launched from a forward inflation the conditions had become sufficiently marginal that the bottom of my harness just grazed the hill as I built airspeed (I suspect I inflated in low/no-wind but transitioned into sinky/tail-wind). Yikes. But once I was properly off launch I was completely in the zone, the flight went well, the approach was solid, and the feeling afterward was of pure glory. I was so wired from the experience that I could not fall asleep for hours after getting home despite being brain-fried.

Pulling off that hike-and-fly represented a huge milestone for my time in Utah generally and my aviation journey specifically, one whose realization required the confluence of skills development, gear tuning, psychological perseverance, and physical conditioning. This outing provided just the experience I needed to head to Alaska flying high instead of needing to dig out of a hole.

My first flight in Alaska, starting from the “Lake Hill” launch of Hatcher Pass, began with an exasperating wrestling match in high wind on a steep slope that sported incredibly slick plants and gnarly unforgiving boulders, engendering an uncivilized amount of cursing as I internally debated whether I should just shut it down…

Then actually getting off the hill involved being plucked with an unresolved cravat, an experience that was super intense in the moment but in hindsight weirdly gratifying. I calmly handled the situation the way I had drilled in SIV — firstly maintaining a steer-then-clear prioritization, this being important to avoid turning a mild nuisance into a senselessly ground pounding disaster; secondly endeavoring to strike the balance of terrain clearance and airspeed maintenance, a critical matter as such a wing compromise brings you closer to stall speed; and thirdly explicitly refraining from matching brake toggles to one hand before using the other hand to clear the cravat with the stabilo line, a mistake there risking the initiation of a spiral dive as I learned quite explicitly in class. Once I had cleared that hurdle my heart was slamming, my lungs were heaving, and my guts were churning, but I stuck with the program and maintained a ridge soaring pattern until my body and brain could catch up with my wing…

Lord knows I was grateful not to have done an “SIV” in this moment where the “S” stood for “Surprise” or “Stupid” instead of “Simulated”, my “classroom” experience last October having amply demonstrated what a shit show that can potentially be…

In any case — for all that effort the gods rewarded me with a breath taking hour-long aerial tour of one of the coolest flying spots in the world right out of the gate. Wow.

Worth noting is that after one more somewhat albeit less spicy launch…

… I was grateful to figure out a portion of the hill that offered the wind shadow to inflate in better control and only then push out to where the ridge’s main compression zone was, allowing me the ability to get going in a much lower stress fashion while subsequently enjoying nicely supporting conditions…

It was even pretty nifty to test and debug my new radio setup which provides in helmet comms as well as a push-to-talk button mounted to my left rear riser…

So much of Alaska felt like a tangible reward for all of my earlier trials and tribulations, not just in the sense of the universe smiling on me with good fortune after long struggles, but also in the way that various component skills both unlocked opportunities and kept me safe.

Having survived a grueling hike and stressful no-wind launch in a race against time back in Utah at Grandeur Peak I was better prepared to navigate the challenges of the “Marmot” launch at Hatcher Pass on a day with rapidly deteriorating weather. I even remembered to bring my trekking poles!

Having previously braved Grandeur Peak’s LZ back in Utah, the one at Alaska’s Baldy Peak did not feel impossibly intimidating, and having figured out thermaling in Colombia I was able to upgrade what might have been a simple five minute sledder into an incredibly fun and beautiful twenty five minute flight which finished with what a local observing pilot described as a “textbook landing” in an LZ “the size of a postage stamp” (it was a little bigger than that).

On top of my many adventurous landings in Roldanillo, having arguably blown my glide to the V’s LZ a year earlier (thanks for having eyes on me Joey!) which culminated in an unplanned fire road landing on uneven ground and surrounded by grass hiding leg-busting boulders (my first XC-esque landing)…

… it was no big deal when I blew a transition from “Diving Board” to “Back Wall” at Hatcher Pass and had to contrive myself a snowfield landing in a pinch then hike upward to re-launch into light wind on steep and slippery terrain (actually the latter part was kind of a big deal as I found myself in another race-against-dying-wind slog of a hike and consequently I was quite relieved that Ariel had side-hill landed to help me navigate that part!)…

FWIW, that landing actually felt way more chill than some of the planned ones at Lake Hill’s main LZ where you are navigating a sea of dirt mounds sprinkled liberally with boulders, making both path selection and flare timing crucial…

In any case, I would have to say that the standout experience of the trip involved my last flight at Lake Hill when I put together all the pieces I had puzzled out on previous flights which enabled me to fly a deeply satisfying mini-XC triangle that ended with a top-landing right where I started…

I can’t thank Ariel enough for offering such excellent friendship and mentorship over nearly two years and for serving as such an exemplary ambassador and guide for this magical flying area. He always bringing the positive energy and his care for the success, safety, and enjoyment of others is unparalleled.

There were even puppies.

What a complicated, arduous, scary, meandering, and yet profoundly enriching and regularly joyful journey this has all been… I feel worlds apart from my 40th birthday of ~2.5 years ago which looked eerily like this…

And large swaths of the intervening time have certainly felt like this…

… but ultimately, though fear is a regular companion and circumstances occasionally seemed to be conspiring to get me to quit, I have felt blessed not just by the destinations but also the journey. If it were easy then everyone would do it.

Bigger Than Just Paragliding

To paraglide, some will tell you, is to hold a mirror up to your soul — it is like everything else in life only more so. The highs are higher, the lows lower, and the risks far more visceral and consequential. The sport will amplify your personal character attributes to the extreme. To navigate its perils and reap its rewards over the long haul requires serious intentionality, discipline, dedication, resilience, risk awareness, risk tolerance, physical toughness, body awareness, quick thinking, timely reflexes, attention management, and mindfulness as well as a robust social support system.

As I stare at that list and take a tough look at myself a few potential problem areas stand out. And what really intrigues me involves how those weaknesses in paragliding often serve as strengths in other contexts.

As a hyper-lateral thinker I excel at outside-the-box problem solving but this can just as well generate racing thoughts which drive excessive anxiety instead of mindfulness. I am also hyper-analytic which is great for risk awareness but less so, especially in concert with other traits, for risk tolerance. I am also quite good at focused thinking which offers a very complicated set of benefits and drawbacks — first considering actually flying, on the one hand I effectively push out all non-aviation thoughts while I am in the air but on the other hand risking fixation on one aviation sub-problem to the detriment of others; second considering the surrounding activities, on the one hand I can quite readily dig deep to assess a problem and generate solutions but on the other hand I may work myself up to an excessive degree on one narrow problem area which engenders issues around opportunity cost, diminishing returns, and general anxiety. Lastly I suspect that my “dedication” is actually more about momentum — I am slow to get going but once I am rolling you had better not get in the way because I am unstoppable; or, less flatteringly, if I am stopped I may be at risk of getting stuck and languishing.

I have been cultivating an assortment of brain hacks to guardrail various of these issues but they require work and discipline. Those struggles perhaps center more than anything on intentionality, mindfulness, and framing. I am striving to be more clear with myself about what I want out of this sport, as well as life, and to that end am fighting to have my higher order self be more thoroughly in command of all my neural circuitry.

When anxiety starts boiling over on the drive to launch I re-frame from “I’m nervous” to “I’m excited”. When I am debating whether to go to launch I strive to time-box the decision process, commit to a course of action, and then put it out of mind lest second guessing allows convenient rationalizations to convert an exciting day into a safe one. When in a rut I regain momentum by engineering a high-density, high-commitment, highly-social “event” that provides the laser focus, sunk costs, and positive energy to get me rolling again.

Perhaps one of the most salient and transcendent mantras in paragliding reads as “look where you want to go”. This works just as well on the ground as in the air. If we fixate on the impending disaster then so do we the more precipitously plunge toward it, whether it be the hard nearby ground after suffering a big wing deflation or the failed engagement with a critical customer in the course of building a business. Will we misapply the Samurai’s admonition to “keep death in mind at all times” and live our lives as “those cold and timid souls who neither know victory nor defeat” or will we employ it as they intended by leveraging the knowledge of our inevitable death as a spur to work backwards from a good death at the end of a life well spent and then plow forward among the “[hu]man[s] who [are] actually in the arena [and] whose face[s] [are] marred by dust and sweat and blood”?

As I zoom out to my larger life I see a period over the last six years trending toward greater risk and ambiguity. Spanning 2016-2020 I found my feet in four different states — Maryland, Connecticut, Ohio, and Utah. During that same period I repeatedly downshifted my employer size by perhaps as much as 100x at each step — from civilian employee at a massive government agency, to employee at a mid-sized financial company, to a fifteen person start-up company, to solopreneur consultant. Through that lens maybe spending the last ~2 years figuring out paragliding merely represents the latest logical step in accepting risk in exchange for an ever richer collection of life experiences.

From time to time I am tempted by the nostalgia of some earlier era or place but I keep repeating to myself “we move forward” and plow ahead, doing what I can to drive the play instead of just reacting to circumstances. It can prove scary, exhausting, and alienating at times to keep acting like I have over the past six years but it is also exhilarating. Nothing is certain with any of these jumps… nothing except an ever growing curated collection of excellent humans and mind expanding experiences.

Early this year local legend Richard Webb offered me some very pithy advice over dinner — “fly more sites”. It was great specific guidance on its own but I found myself generalizing to a Data Scientist’s caution to avoid “over-fitting the model”. At the time of that conversation I had flown all of four sites — POTM-SS, POTM-NS, Utah Lake for SIV, and the V. In the intervening months I grew my collection of flown sites by more than double, adding six new ones — a site in Piedechinche, another one in Roldanillo, Grandeur Peak here in Utah, and then three different sites in Alaska. The value has proven enormous, taking shape in obliterated assumptions and consequently the flourishing of more general purpose mental maps about how to fly.

And as I zoom out I can see an evolving way of being wherein I am increasingly waging a war on over-fitted conceptual models. I used to operate in professional contexts with risk guidelines and delivery timelines tuned to government work. Now all these years later I instead dynamically tune my engagement style to the case at hand, having become able to do so as the result of a body of work that now spans both public and private sectors, multiple domains, several employer sizes, and varying contractual arrangements. With every new site I fly, every new place I live, every new friend I make, and every new professional partnership I forge, navigating the next one feels that much less intimidating. This feels like progress.

I think my late maternal grandmother would be mortified in the knowledge that I took up paragliding shortly after she departed this mortal plane, but probably the recent trajectory is at least partly her fault, her refrigerator having always been adorned with the following Hunter S. Thompson quote, so be mindful of the influence you may be having on others…

Life should not be a journey to the grave with the intention of arriving safely in a pretty and well preserved body, but rather to skid in broadside in a cloud of smoke, thoroughly used up, totally worn out, and loudly proclaiming “Holy shit! What a Ride!”

Blood On The Data Center Floor

I put my head in my hands, elbows propped on desk, the realization sinking in what kind of day it would prove — one like far too many around that long-ago time, alas. With some regularity a key processing system operated by a sister office was going into fits of data loss, leaving our operational picture resembling Swiss cheese. How could this happen? How could people let this happen?

In some sense the answer was simple even though the problem was complex. A flow-based programming system born of one domain and built to run on metal had first been ported to a fundamentally different domain and subsequently resettled to a container farm during a fit of irrational and ill-informed “Cloud” and “NoCode” exuberance. Where in another place and time the former experienced low rates of data loss in a context where losing a little data was no big deal we now had a situation where high rates of data loss were occurring in a context where even a little loss was severely damaging.

The slightly more complex answer involved a firehose of data transiting a complex workflow that for any object might take an unpredictably long time to execute. Worse still, the processing of an object entailed invoking an external metadata management service common to all workflows. This external service, notably, was subject to getting overwhelmed and dropping requests, a scenario that API clients managed by implementing retry protocols on their side, often fomenting a flash crash as competing systems raced to the bottom. Thus objects would pile up deep within these workflows for indeterminate amounts of time as the memory usage of an underlying container crept upward until…

*BANG*. All your data are belong to /dev/null.

The historical stability of the underpinning infrastructure led to a software product with systemic fragility that could not withstand a sudden change in circumstances.

The Goad To Reflection

I recently finished reading Taleb’s Anti-Fragile in which he explores the properties of systems that thrive on volatility, randomness, disorder, and stressors. You should read it, too, as well as his other works. Throughout my read I found neural pathways lighting up to situations in my own reality. At the end Taleb exhorts readers to reflect on applications in their own lives. This represents my attempt to do so.

Fractally Distributed Systems

I credit my Distributed Systems professor Yair Amir with stoking a fascination with and passion for understanding how complex systems break and what means we have for dealing with them. Some twenty years later I have memories of profound aphorisms such as “the network is not a disk” and hands-on projects that drove the points home. From his class I gleaned many timeless and universal techniques for fostering resilience in systems. Certain higher order lessons, however, would have to wait for the violence of directing the development of complex systems over the span of years and countless calamities. I would require a many-layered journey to properly become a generator and purveyor of such knowledge myself.

Taleb, meanwhile, begins by explaining to us that not just is our intuition about what “anti-fragile” ought mean wrong but human language has altogether lacked a single word to capture the concept. To be anti-fragile does not mean simply to be “resilient” or “robust” in the face of adversity but rather to gain from it. It implies an ability to evolve which hinges on many things.

To build a robust software system in a complex domain, first you must set out to build an anti-fragile wrapper system, one capable of absorbing and operationalizing myriad hard lessons accumulated over many years wrangling chaotic problems. Notably, that anti-fragile system must be viewed not just through the lens of technology but also culture, with key areas spanning the following…

Humility

We must have a culture that encourages people to own their mistakes, to do so publicly without fear of retribution, and to seek the counsel of others on how to do better. We must likewise encourage people to be humble and explicit about the risks they are assuming, demonstrating a realism about the struggle they may be taking on with a project. Without this people will live in fear and treat their troubles as liabilities instead of assets while behaving in a manner simultaneously secretive and reckless.

Observability

We require the knowledge to understand what triggered a bad outcome. This implies the generation, processing, storage, and analysis of high quality telemetry. If we don’t know what is true then we cannot tackle the problem that exists. In systems engineering, premature optimization is the root of much evil, and without a rich radar picture of where problems lie we will forever find ourselves focused on the wrong problem while laboring under bogus theories.

Agility

We must have the technology and culture to move quickly yet responsibly. This implies not just a mature DevOps toolchain in the realms of CI/CD and infrastructure-as-code but also flexibility in Data Engineering architecture and furthermore a dynamic approach to managing risk that views dangers in strata and makes recommendations accordingly. The more agile a team’s approach the more the more the team can exhibit anti-fragility by quickly codifying lessons learned in its software and organizational DNA.

Accessibility

Critical to our ability to innovate is access to data and systems that allow us to tinker. Empowering people to fashion a bricolage that solves a problem they have, doing so quickly and unilaterally, accelerates the generation of knowledge and capture of value. This entails open access to APIs and data lakes as well as sandboxing mechanisms that enable exploration while avoiding compliance headaches.

Diversity

We often find ourselves locked into rigid hierarchies where bureaucrats assign “lanes” in which subordinates possess the mandate to operate and deviation from which yields punishment. This fosters a toxic ecosystem of turf wars, learned helplessness, and incestuous amplification. Even though a specific group or product may have formal responsibility for a particular area we should encourage tinkerers everywhere to self-actualize.

Transparency

And yet we squander all of this accessibility and diversity if we fail to make it safe for people to be transparent about how they are approaching problems. If officious bureaucrats shout “not your lane!” and seek to quash skunkworks initiatives then they inevitably drive them underground, either destroying them altogether or at least failing to fully capitalize on their innovations by triggering compartmentalization, simultaneously damaging morale and fueling attrition.

Maturity

But if we are to embrace such fluidity then we must also remain clear-eyed about maturity. The hand edited Python script that haphazardly scrapes some APIs while running in someone’s private sandbox lives on a whole other plane of existence from something that is explicitly versioned, cleanly packaged, automatically deployed, robustly monitored, demonstrably scalable, and so on. Far too often stakeholders conflate the potential of a PoC with the sustainability of a productized system. Avoiding such pitfalls requires mutual respect and open dialogue between multiple parties.

Community

As tools and tradecraft that underpin solutions to cross-cutting concerns mature owing to diverse and transparent activities transacting on accessible data and systems we should cautiously and gently act as gardeners who tame and channel such organic growth into lasting solutions while accepting the need for continual change.

Toward Resilient Software Systems

There is a certain beauty inherent in the violence of running an application within containers underpinned by a shared cloud and subject to unruly third party integrations and downright hostile actors. Execution contexts disappear without warning on a regular basis. Latency for all manner of things drifts as a matter of course. Load shocks reliably emerge from nowhere at the most inconvenient times. Deployment of components happens in an utterly asynchronous and parallel fashion. And, always and forever, humans gonna human. Not just is it that “anything that can go wrong will go wrong” but furthermore “all the damn time”. Best to start figuring out solutions as soon as possible and organically instead of trying to become robust one future day all at once and via top-down command-and-control edicts.

A central thesis in Taleb’s work states that local fragility enables systemic anti-fragility which in turn fosters a greater resilience over time. What better ecosystem for this could we imagine than the aforementioned application architecture coupled with a healthy engineering culture? The pervasive and continual unreliability of our componentry serves as an anti-fragility pressure cooker, forcing us to continually work at resilience in a way that proactively builds resistance to mundane mishaps and Black Swans alike. The lessons to be learned span all of the following and more…

Respecting Responsibility

Your compute fabric is going to sporadically disappear out from under you. You had better not claim responsibility for a piece of data before it has made it to its rightful destination. What business have you consuming a message before you have successfully processed it? And wouldn’t it be nice to practice with losing containers before you lose a whole rack of equipment?

Expecting Errors

You are going to ship buggy code. It is going to mis-process data. If you don’t make data replay a first class citizen then you’re gonna have a bad time. And if you don’t ready your processors to consume replayed data you’re going to have an even worse time.

Craving Chaos

No reliable ordering? No exactly-once delivery? No problem! Develop a sequencing protocol, slap timestamps on everything, queue up fragments, and make your processing idempotent. Hard drive failures? No worries! Just stop installing packages on servers, instead building fully self-contained Docker images, and configure your most critical data to replicate across Availablity Zones and maybe even Regions.

Anticipating Assholes

People are going to try to game your system. Consider making your APIs asynchronous, queue based, partitioned, and metered. Hijackers gonna hijack. Build your container images minimally to reduce attack surface and starve them of tools, minimize tasks’ connectivity and permissions to reduce blast radius, make processes and tokens short-lived to reduce the window of compromise, and wall off subsystems with network and account boundaries.

Hating Heroism (in some of its forms)

The greatest fragility of all perhaps resides in the people who build and operate a system. Make them take vacations and see what breaks. Unplug direct administrator access to production systems to see who freaks out and what bursts into flames. Ensure that releases kick off with a single click and have every last configuration parameter tracked in a version control system. When a hero rushes in to save the day, consider asking one simple question — Is this savior not just the solution to but also the cause of my problems? Making people take time off doesn’t just stave off burn-out. It also surfaces critical fragilities that could easily escalate from nuisance to catastrophe.

The Larger World

We are tempted all the damn time to build fragile systems in the name of efficiency, safety, and comfort, but it is a fool’s errand that leaves us complacently sitting on a keg of dynamite in the form of tail risk.

Want social media to regulate content? Sounds nice, but… What entrenched interests will end up deciding what is true and/or palatable? How much power do you want to put in the hands of tech oligarchs? What happens when The Other Guy is in office tomorrow? How do you feel about Big Tech becoming an organ of the state? What unintended consequences will we reap from letting algorithms control our discourse?

Worried about gun violence? Tempted to strip all private citizens of guns? How do you respond when some lunatic, bigot, or terrorist runs amok and mere seconds make the difference between a short-circuited attack and a massacre? What happens when a populist authoritarian thug hijacks a democratic government and begins rounding up an unarmed populace? What timely resistance will you offer if an expansionist neighboring country begins rolling armored vehicles across your border? How will you distinguish yourself as a citizen versus a subject? Some subset of the population will always have arms. Why not everyone within reason?

Want a hyper-efficient economy predicated on globalism, specialization, outsourcing, consolidation, and just-in-time manufacture? Cheap and plentiful products are nice, but… What happens when a country weaponizes its position as an energy provider? How do you fare when a single enormous boat blocks a critical canal? Or when a planetary-scale SaaS provider suffers a class break that compromises all of its customers? What happens when a pandemic spooks people into hoarding staples and countries into nationalizing strategic resources? How do you adhere to your principals when it turns out that the mining and manufacturing in foreign lands that underpin the products to which you have become addicted involve environmental destruction, forced labor, child soldiers, and perhaps even genocide? And such platforms as smart phones are monopolized by just two Big Tech companies? Or public clouds by three? Or the production of your food is run by an ever shrinking number of increasingly massive agribusinesses and food conglomerates who buy politicians, poison people, and commit atrocities against animals while shielded by Ag-Gag laws?

Not sure about climate change? Yes, it is a big messy subject with a lot we don’t yet understand regarding both the structure of causal chains and the efficacy of potential solutions. But don’t get hung up on that. Instead start by simply thinking in terms of Risk Of Ruin and Via Negativa. We have exactly one planet, this planet represents the most complex system we have ever known, we are growing rapidly while tinkering recklessly, and getting things wrong could quite literally foment the extinction of our species. Perhaps some humility is in order? Perhaps the burden of proof should lie on those claiming no harm while profiting from rapidly making large scale and poorly understood changes to a system evolved over billions of years? Perhaps predicating our whole economic reality on perpetual growth to manage extreme indebtedness is a recipe for collapse?

Let us forsake the false idols of global efficiency, local safety, and temporary comfort, replacing them with the hard work and humility required for the anti-fragility we need to survive and thrive.

Lastly

What better way to exhibit personal anti-fragility than to keep cogitating on confusing topics while maintaining the courage to press the “Publish” button and the open-mindedness to hear feedback? I often get to the end of a writing project and find myself tempted to stuff the piece in a private drawer because I feel that the treatment is either too inchoate or too incoherent. Mostly I overcome that cowardice and just push it out to the world in all its imperfect glory, humbly accepting that today’s ruminations represent works in progress that may take decades to reach fruition. How different a world might we inhabit if everyone could feel safe in doing so? How more meaningful a dialogue might we have if the bulk of our discourse were not held hostage to machine learning algorithms implementing Sort-By-Controversial while fostering 15 second and 280 character attention spans?

No perfect person exists for a given role, just the best one at a point in spacetime. So, too, it goes for process, technology, and culture. Thus to successfully steer an ecosystem leaders must emplace the right team at the outset, sense phase transitions proactively, and modify conditions smoothly. They must also reliably recognize when their purview includes activities requiring shrewd partitioning. Act too soon and one creates headwinds that stifle innovation and undermine purpose. Act too late and the enterprise finds itself bogged down in a swamp and breaking promises. Timing is everything.

Navigating The Phases

Engineering activities operating under an iterative delivery model endlessly cycle through a well known set of phases to release new units of functionality, but they also simultaneously progress linearly through a higher order set of phases. We interest ourselves with these latter phases presently, both with regards to their inherent nature and the kind of people and culture that best support them. Note in particular that although an individual may have competency in a range of phases, competency in one typically comes at the expense of competency in another, and yet “Flexers” serve a key role in smoothing phase transitions.

POC: To create a Proof Of Concept, inventors lay out some novel idea and endeavor by hook or by crook to prove vague technical feasibility. We must emphasize creativity and risk taking while shielding the activity from bureaucracy. The outputs of this phase may justify further investment but we must hold them in suspicion as we would scientific research not yet peer reviewed.

MVP: Progressing to a Minimum Viable Product requires enough engineering rigor to avoid squandering the confidence and enthusiasm of initial contacts and yet also a ruthlessness for cutting just the right corners to expedite time to market. We must emphasize practicality and resourcefulness while quashing unduly speculative investments. In reaching this threshold we begin to attract early adopters who will help us shape our product. We also find ourselves increasingly at risk of getting too far out over our skis.

Scaling: To enter the Scaling phase involves a transition from building something people want to building something enough people will purchase at a price that supports operating a sustainable business that can stand up to compliance scrutiny and hostile action. To navigate this phase entails managing the scaling of multiple facets — infrastructure costs, product complexity, team size, and customer composition. We must emphasize prioritization, automation, reliability, security, and unit economics. Increasingly we require the services of technical specialists to navigate arcana and managerial generalists to control complexity.

Sustainment: Often foolishly characterized as the unsexy “Maintenance” portion of the lifecycle, this phase in fact offers the most complexity and peril as burnout, bureaucracy, and complacency enable the competition to eat our lunch. Managed poorly it marks inevitable decline. Should the right people seize the moment, however, the enterprise may evolve to a fractal shape, one effectively consisting of a company of companies. At this point many such “companies” may exist out-of-phase, a substantial amount of politics become inevitable, and a critical personnel archetype must emerge to walk the knife’s edge of stability and relevance.

Managing A Company Of Companies

Having established a viable business model, a company will then find itself contending with the following inextricable challenges:

1. Protecting existing equities
2. Maintaining market relevance
3. Managing cultural conflicts

To borrow the terminology of Safi Bahcall’s Loonshots, we increasingly find ourselves at risk of conflict between the “Soldiers” struggling to operate the business of today and the “Artists” striving to imagine the business of tomorrow. And to manage this challenge we may seek to integrate these disparate groups while creating a single homogeneous culture — a terrible mistake. The Soldiers will experience the Artists as anarchists, the Artists will experience the Soldiers as bureaucrats, productivity across all measures will tank, and attrition will ensue. Far better to recognize the unique values of each, craft an organizational architecture that provides homes for both, and foster Flexer individuals and squads to maintain dynamic equilibrium at the boundaries.

In the context of the aforementioned phases, Artists gravitate toward the POC end of the spectrum and Soldiers toward the Sustainment end, while the ideal Flexer will have the bulk of their skills in the Scaling portion and yet also have at least some competence and inclination in the adjacent MVP and Sustainment realms. Perhaps the most salient challenge herein consists of giving both Soldiers and Artists a home base of compatible individuals while avoiding a toxic antagonism stemming from a “throw it over the wall” approach around transitioning prototype functionality into production systems. Instead of experiencing such an abrupt phase transition we can instead employ Flexers to continually be asking the Soldiers “wouldn’t it be nice if you could do this? and the Artists “have you taken into account these constraints?” so that innovative capabilities have a smooth path to landing in sustainment organizations.

Tangled up in all of this are vexing challenges around the following…

1. Cross-cutting technology and techniques
2. Access to systems, data, and users
3. Respect for process and equities
4. Inertia, complacency, and possessiveness

Separating The Timeless And The Transient

Huge risks exist in nascent enterprises around premature investment in infrastructure and enforcement of rigor. What good are those outlays in comprehensive test suites, hyper-scalable architectures, and bulletproof security when you realize you were building the wrong product and have to pivot hard? And yet, while we ought fold rigor into our applications in a dynamic and phase-aware fashion, we should also view certain certain basic technology and techniques as foundational and universal, shaping them as early and as generically as possible.

We will doubtless discard most of the code written as we navigate the idea maze on our way to a valuable product. The incentives and rationale for a minimalist approach are strong. Nonetheless we would do well to tease out two timeless elements from all that will likely prove transient…

1. Accessible data warehousing
2. Flexible DevOps tradecraft

Why? Two simple needs…

1. Continual reassessment
2. Sustainable velocity

Accessible data warehousing provides the basis for generating intelligence on both how we are performing today and where we may want to be tomorrow as well as the raw material to build new applications. Flexible DevOps tradecraft, meanwhile, allows us to consistently sustain velocity despite shifting requirements and growing complexity. At the outset we will likely have only the crudest idea of what we will ultimately build and so let’s have the humility to stack the deck in our favor with the right foundational investments.

Meanwhile, as a company grows, an interesting question emerges around whether to take a “mission striped” or “function striped” approach to organizational architecture as pertaining to specialists supporting cross-cutting concerns. The correct answer is often “both”, especially when it comes to the realms of DevOps and Data Engineering, but perhaps equally as often with Security Engineering and UX. In particular, an organization and its specialists may benefit from establishing Centers Of Excellence around certain practices, expecting that practitioners will both have long-term assignments with product focused areas as well as participate in and draw on pools of similar specialists. These CoEs ensure that individuals receive appropriate mentorship and peer review, tooling and tradecraft exhibit convergence, and the enterprise reduces risks around knowledge silos, burn-out, and general immaturity.

Safe Spaces

Artists need the flexibility and chaos of a mad scientist’s lab. Soldiers thrive on the order and predictability of a well run factory floor. And each group requires the other to sustain long-term vitality. Instead of glibly and universally promoting a “bias toward action”, organizational architects must visualize risk strata and think in terms of the Fast/Slow Problem which dictates that entities that need to change quickly must not be collocated with entities that need to change slowly.

Matters inevitably become fraught, however, when Artists attempt to gain access to realistic data whose safeguarding lies in the remit of Soldiers. In some cases such data may represent the company’s Crown Jewels and in others pose perilous compliance risks. Various techniques exist to smooth the process while preventing spillage, spanning sanitization, sandboxing, and field-level access control, all aided by elastically scalable data warehouses that are isolated from user-facing production operations and can handle bursty non-quite-planful loads. Mature DevOps processes with fast cycle times further ease the struggle by allowing exploratory analytics a fast path into environments with production-level data controls.

That promotion of code, however, represents the second and previously intimated problem around transition and ownership. Far too easily a “prototype” becomes “mission critical” only to have the Artist progenitors become bored and the inheriting Soldiers behold what the former hath wrought with horror. We might lay the blame squarely on the Artists for taking a “throw it over the wall” attitude around responsibility hand-off to Soldiers but in fact that cultural toxicity often results from and pairs disastrously with the cookie licking and change aversion of the latter which foments a secrecy on the part of the former. In many places “it’s better to ask forgiveness later than permission now” which foments guerrilla engineering, but that is a hallmark of the aforementioned toxicity and indicative of a lack of Flexers that empathize with both groups while gently coordinating their activities.

And all the while the siren’s song of micro-service architecture calls to us, promising us clean boundaries in which small teams can have their own safe spaces to tinker and make technology choices unilaterally. Beware, however, that while such an architecture can serve as a valuable technique for scaling the number of participants building a complex system, it requires a keen understanding of several techniques, demands a certain maturity of DevOps tooling, imposes a per-service tax, and when unmanaged increases the risks of Balkanization. As with all matters, timing is everything, and attempting to adopt a micro-services architecture prematurely nearly always yields instead the dreaded Distributed Big Ball Of Mud.

Conclusions

The growth-oriented organizations that last are the ones that recognize that their internal structure must both continually change and avoid homogeneity. Be sure, however, to file this under “necessary but insufficient”. Far too often, alas, re-orgs result not from a careful consideration of the present context but rather the predilections and politics of the day’s power brokers, yielding violent pendulum swings between the extremes of mission-striped and function-striped architectures. Predecessors are blamed, reshuffles are made, and, finally, three envelopes are prepared…