Reminder Of The Day

“Sweet merciful sleep!”, I exclaimed upon waking this morning. The AutoSleep app reported that I had crushed it with over eight hours of uninterrupted slumber but I already knew this from the delightfully tingly feeling of a well rested brain in the wake of an anomalously bad patch of nights.

I rolled over, pulled my phone off the night stand, and called up the recent wind data for Point Of The Mountain’s southside…

“Nooooooo! ARGH!“, I thus registered my visceral disappointment upon seeing wind far in excess of sensible.

Shortly thereafter a friend would report that he had injured his ankle yesterday and thus today’s posited outdoor climbing activity, a soon to be off-the-table modality until the spring, was not in the cards.

Of note — this confluence of Saturday morning parameters arrives after a four day streak of dumpster fire-esque sleep quality of the kind where I would give up in the middle of the night and perform some mindless task in search of tranquility, sullenly accepting that the subsequent day would likely be long on fatigue and stupid while short on productivity and enjoyment.

During that four day window I consistently declined opportunities to fly while my messaging and social media feeds burst with people plotting outings and having a rocking good time. Paragliding represents one of the most enjoyable things I do and yet also offers the highest complexity and consequentiality. If my brain feels like sludge then I steadfastly decline opportunities to get my feet off the ground. There are many contexts where “power through the pain” or “fake it til you make it” is the right approach but becoming airborne is not among them.

Of further note, however — frustrations such as the foregoing are now the outlier instead of a regular affair; in just over a year in the sport my paragliding journal records 142 days strapped to a wing while last winter afforded me over fifty days clipped into skis.

What better intro, then, to the topic I wish now to explore?

Life Reimagined

Fairly early in my reality I established an appreciation for the value of time as a quantity. Perhaps, more than anything, having available to me more hourly consulting side hustle opportunity than a full time job and social life would allow me to exploit drove home the need to think ruthlessly about opportunity cost in the context of choosing whether to perform or outsource a task.

Only much later in life would I really come to fully appreciate the enhanced value of time when you can tap that resource with flexibility. For that I would need to decide “enough is enough”, crash unexpectedly into a global pandemic, pivot from the upended idea of “sabbatical year” to “accidental consultant”, execute on a long-held dream of moving out west to live and work in the place I wanted to play, and finally start to tackle the challenges with insomnia that had been plaguing me for years.

The Various Systems

To do that would require a more conscious effort to bring various facets of my reality into harmony, each exhibiting their own amounts of randomness, degree of controllability, and expected periodicity:

1. Global Sociological Phenomena
2. Current Life Configuration
3. Present Mind/Body State
4. Imminent Meteorological Conditions

As I have discussed at great length elsewhere, by the beginning of 2020 I had a long overdue moment of reckoning with my personal “weather” and began navigating myself to a different reality to facillitate a healing process. Along the way my professional network would present an assortment of opportunities that could either accelerate or short-circuit this journey — in addition to various consulting gigs, many folks also made full-time job offers, all tempting in their own ways, but I have politely and resolutely declined all of them.

These various full-time opportunities earnestly promised all manner of flexibility, but to live the life you want in a given moment you must understand the precise manner of flexibility required. I have loved, and perhaps when the time is right will love again, the experience of being a full-time executive-level engineering manager, but that substantive responsibility comes with myriad constraints which one ought not accept carelessly.

There seemed in this moment a perfect and rare confluence of available options for key parameters. Seizing upon this highly unique opportunity, I scrupulously avoided accepting any unduly encumbering arrangement and set about assembling the puzzle pieces — COVID rendered remote tech work ubiquitous, my professional network concretized such opportunities, personal savings let me accept increased financial risk, an unencumbered social reality let me uproot to move across the country, a depressurized professional cadence has allowed me to process grief and anxiety while repairing sleep habits, and a truly flexible work schedule has allowed me to fully exploit opportunities to engage in highly weather sensitive activities.

A Former Golden Age

All that said — I find myself pondering with some regularity an earlier arrangement, glorious in its own right and much missed, a slice of several extremely intense but highly rewarding years working in the government.

I lived in a city, worked in an office, maintained a manic focus, ate lunch with colleagues daily, and built software that still makes the world turn. I took full advantage of a perhaps once-in-lifetime confluence of mission, mandate, technology, and people. I also got fat, became sick, neglected relationships, lived with stress as my constant companion, and continually accepted an increasingly self-destructive amount of responsibility.

I would take skiing vacations, sure, but maybe for a total of 10-15 days per year if I were lucky. When I showed up at the mountains sometimes it would be for amazing powder and others for a disappointing snow drought. I would generally be too tired from everyday life to catch first chair. Sometimes I would make the trip only to get sick in the middle of it. Other times plaintive co-workers would be pleading for help with problems at the office. Getting all of the “weather” systems to align was an incredibly unlikely event.

I don’t regret configuring my life thus for a time. Most people spend a whole career never once getting to do things as cool and impactful as I did in that era. And the spoils of those trials and tribulations in many ways laid the groundwork for my present reality. But boy did it come at a high cost and you can bet I will be careful going forward about how I navigate my way back into a similar arrangement in the future.

An Interlude For Empathy

My struggle to make sensible decisions around whether to fly in a given moment has engendered a deeper respect for the challenge that many professionals navigate as a matter of course day in and day out.

For the most part today I have total autonomy to make a sensible “no fly” decision as a paraglider. If I wrangle my own logistics, listen attentively to how my body and brain are feeling, and stubbornly refuse to let FOMO govern my behavior, then there is no reason I should find myself in the air when weather conditions either meteorological or neurological are anything other than highly advantageous.

When I find myself, say, in a paragliding clinic where both a narrow band of opportunity exists and I have made non-reversible commitments of both time and money, then I exploit the flexibility I have elsewhere to aggressively protect sleep hygiene and discharge obligations while simultaneously repeating to myself the wisdom of ignoring sunk costs.

I shudder to think, meanwhile, how ill-advised many of my flights may have been during instructor guided training in pursuit of a private pilot license of the PP-ASEL variety — I was reserving time by the hour of both a rented plane and a hired instructor; my then work schedule was theoretically somewhat flexible but overall extremely onerous; and consequently the pressure to go through with plans was enormous. I am haunted by the thought of what distractions one of my instructors must have been navigating when pilot error got him killed while training with another student on a day between my scheduled lessons. What part of the IMSAFE Checklist did he ignore on that day because, perhaps, he had bills to pay, a reputation to protect, or a relationship on the rocks? I will never know but I can guess.

Over time I have come to reason in terms of two collections of Four Layers about whether I am up for a given task…

Firstly there is the collection of questions I ought be asking myself:

1. Do I have the ability to perform this task well under any circumstances?
2. Do I have the focus and stamina to perform this task well in the moment?
3. Do I have the awareness when degradations to (2) have compromised performance?
4. Do I understand the risks in a given moment if I come up short on any of the former?

The last item of this first list expands into a collection of four risk strata explored in detail elsewhere but excerpted here (and left with descriptions somewhat specific to Software Engineering yet I think nonetheless readily generalizable):

1. Photons: you botched the code that does final rendering for a feature that is of low impact and/or is tolerant of moderate latency and you need only ship a new version of that code to return to full capability
2. Electrons: you corrupted data and need not only ship new application code but also create and run data repair code that may take a while to execute during which period there may be material delays incurred by time critical business functions
3. Atoms: your system gave (or failed to give) instructions such that there were substantial bad outcomes in the physical world, perhaps damaging, degradrading, losing, or misrouting physical items that will be costly to recover or replace
4. Meat: your system gave (or failed to give) instructions such that people were traumatized, maimed, or killed, consequences for which no amount of engineering work can compensate, generally limited to areas such as Transportation, Medicine, Industrial Control Systems, Command-and-Control Systems, Fire Control Systems, Law Enforcement, and Intelligence

Which finally brings me around to the point of this section…

With Paragliding — every time I strap into a wing I am taking on a Meat-level series of decisions, but this is just a hobby, I have accumulated at least some experience about what is sensible, and I always have the right to say “NOOOOP!”.

With Software Engineering — I find myself with some regularity navigating risks at the Meat level, and one of the really confounding problems is the ambiguity about which layer you are navigating in a given moment, but generally I have the luxuries of time and triangulation to crank up the deliberations accordingly.

Many professionals, however — medical personnel of all stripes, commercial pilots/captains/drivers, combat soldiers/sailors/airmen, police officers, industrial operators… the list goes on — are navigating Meat-level decisions every day, seldom have time on their side, and rarely have the option to say “uh, yeah, I’m gonna sit this one out”.

Often the accidents and attrocities we observe appear to manifest from poor individual decision making and boy do we love some good armchair quarterbacking. But hot damn do we create some dubious systems-of-systems that leave individuals straining under unreasonable circumstances, carrying unreasonable amounts of risk, and bearing the brunt of the consequences.

It is tempting to “hold people accountable” but more often than not we ought, at least additionally, be looking at the systems we have wrought, as well as remember that when you force someone to make thousands of snap decisions in high consequence situations under adverse conditions then at least some of the outcomes will inevitably look like mistakes.

I am reminded of this both prior to and during every paragliding flight. Before launch I always have the luxury of saying “pass!”. Between every launch and landing, meanwhile, the universe holds one thing inviolable — no time-outs!

The Inevitable Social Pressures

Paragliding, in one regard, offers a highly paradoxical experience — it is at once intensely isolating while simultaneously extremely social.

Risk management is incredibly personal in that so many decisions in this sport represent a “life choice”. Once strapped into a wing, only your skills, diligence, and decision making separate the good or at least unremarkable days from the scary or downright disastrous ones.

And yet the narrow bands of weather that offer flyable conditions drive us to be out there together and the community offers incredible value in the form of mentorship, camaraderie, and support both emotional and logistical.

This leaves us in a perpetual tension that can prove tricky to navigate.

In a recent UHGPGA group posting on Facebook a pilot asked the community what they thought being a good pilot entailed. I reprint my list here to call out three specific items that feel relevant to the current blog post:

1. continually learning
2. learning across facets
3. patient in progression
4. humble about abilities
5. avoids the scarcity trap
6. avoids the sunk costs fallacy
7. maintains wide margins in all things
8. appreciates the diversity of goals, experience, and personality across pilots
9. generous with perceptions without being pushy
10. creates an environment where people are comfortable sharing their mistakes and fears
11. strikes the balance between positivity and sobriety
12. calm and skilled in the handling of emergency situations in all their forms

I find myself pondering these three items in the context of how they apply to a range of pilots in my social circle: the ones who are insanely badass yet somehow remain reliably accessible to me as aviation buddies, the ones where our default positions were at odds which created some friction but we put in the work to make the relationship work, and the ones that were too “my way or the highway” and thus blew up the relationship.

I think I am open-minded enough to be generally good with (8), I have to consciously work at (9) but I try damned hard, and I recognize that the Security Engineer in me creates potential problems around (11) but diligence with (8) and (9) make it possible to be socially tolerable when observing conditions outside my envelope but acceptable to others.

In any case, all three of these involve complex “weather systems”, each with a different degree of accessibility to us. We can, over time, learn what other pilots are like generally. We can even endeavor to keep abreast of the goings on in their lives. We cannot, however, have any real idea what is going through their head on a given day. This argues strongly for patience, empathy, nuance, and flexibility.

And, paragliding being a mirror held up to our souls, I find myself pondering how the pressure cooker of this sport reveals where I have come up short elsewhere, in relationships both professional and personal. The consequences of being wrong in this game are more obvious and less recoverable than anywhere else in my reality but perhaps their underlying reasons are much the same and their implications nonetheless serious.

Playing The Confidence Game

In navigating some difficult circumstances I have had some pilots say “you’re overthinking it!” but I have personally found that profoundly unhelpful. That might be just what one person wants (wants) to hear in a given moment but the worst thing you can say to another. Remember in particular item (8) from the earlier list. Consider also the possibility that it’s just plain crap advice for a high consequence activity.

I personally strive to adhere to the following approach when navigating adversity in paragliding and hope to increasingly bring same to the rest of my life:

1. Engineer surrounding contexts to provide the “weather” required to put in the work
2. Take the time to step back from unpleasant experiences to assess their root causes
3. Isolate problem areas, recreate triggering situations, and practice practice practice
4. Accumulate a progression of successes to serve as a rational foundation for confidence
5. Continually expand your envelope gradually, methodically, and deliberately

Or, to borrow the words from another pilot, someone who seems in tune with the Security Engineer mentality I inevitably bring to every flight…

Right now in our society there’s this heavy emphasis on the power of positive thinking. Just believe in yourself, dream it, and do it. And I think it’s all bullshit. When it comes to adventure sports it’s just gonna get you killed.

In my view, a useful tool for surviving these sports, or anything risky in life — starting a new business or whatever — is to try to figure out what can go wrong and why. Then when you go out and do something in life, you’ve got justified confidence, not just a sort of “I’ve got this” belief that you can do anything.

Will gadd, excerpted from “the positive power of negative thinking” in gavin Mcclurg’s “ADVANCED paragliding”