Stacking The Deck

If you’re not cheating then you’re not trying hard enough.

As I gaze forward and imagine how I might shape what feels like a new epoch in my life so do I feel compelled to look backward to glean wisdom from fifteen years of big projects since leaving school. Success inevitably involves substantial luck but many ways to stack the deck exist.

The Takeaways

In performing this retrospective several themes emerge from professional and hobbyist contexts alike:

  1. Energy
  2. Focus
  3. Pacing
  4. Mentorship
  5. Championship
  6. Talent Density
  7. Team Composition
  8. Problem Visibility
  9. Chaos Exploitability
  10. Data Accessibility
  11. Outcome Measurability
  12. Solution Flexibility
  13. Artifact Compoundability
  14. Power User Engagement
  15. Downside Risk Management
  16. Feedback Loop Latency and Integrity

The Odyssey

When I left Hopkins in 2005 to begin what would prove an eleven year odyssey at the Defense Department I stayed put in my Charles Village apartment in Baltimore, landed in the middle of a re-org, slotted into a “Concept Development Group” tiger team, pounced on an opportunity to flesh out a piece of demoware a colleague had dreamed up, found myself too broke for a personal life and glad for overtime pay, and lucked out in finding a few people who each served as combo mentor-and-champion. This checked many of the aforementioned boxes and I managed to make a pretty big debut splash, quickly rack up a couple of promotions, and grow a sizable team around the nascent product.

Over time, however, a variety of headwinds became evident. After the dissolution of the CDG I found myself in a fractally matrixed organization. Top level offices partitioned along the lines of engineering, analysis, operations, and legal/compliance. Engineering further broke down along the lines of software development, systems integration, and systems administration. I was building a platform that was chasing applications while sitting on the opposite side of a large campus from the analysts who were excited to use my product but hadn’t yet figure out how to make it real. For various legal and compliance reasons getting API access to SIGINT databases proved laborious. The non-availability of modern Cloud and DevOps tools and techniques made fielding infrastructure and releasing software increasingly slow and messy as the team’s size and the system’s complexity grew. Lastly, the lack of end-user customization/scripting faculties compounded the pain of the slow release cycle to which only formal software engineers could contribute. In the end the product did not have quite the level of impact and longevity I had hoped, perhaps the largest long term value being its cannibalized DNA that informed the direction of other products.

In 2009 I decided to stay at the Defense Department but move to another office where I would take over the productization of a prototype collection system. The first year proved fairly messy and tumultuous, owing both to my having a lot of new knowledge to take on as well the larger ecosystem being somewhat roiled with present day goings on, but I learned a lot and established some key relationships, and then a pretty magical re-org happened wherein a few elite people from each of my parent office’s sub-offices were handpicked to form a new office that would be housed in a nearby satellite campus. And just like that I found myself on a small but highly cross-functional team with great access to data, a close proximity to real mission, and a mandate to operate in Mythbusters fashion by modernizing tradecraft. Unlike most other places we had incredible unilateral ability to develop, deploy, and operate tech which gave us deep insight into concrete problems and an awesomely tight feedback loop.

Not only did the environment in which I was operating confer enormous advantages but also the general approach to the technology proved far more effective. First and foremost the arc played out as a tangible application that evolved into a flexible platform, ensuring that we were always taking a practical approach to solving important problems. Secondly we designed, warehoused, and analyzed high quality telemetry that gave us clear visibility into system behavior, user engagement, and mission effectiveness. Thirdly we created open APIs that empowered analysts and operators alike to play in our ecosystem in an experimental and decoupled fashion that, bolstered by our telemetry faculties, informed future formal development activities. Fourthly we carefully established abstraction boundaries that optimized for the flexibility and longevity of the component technology of the ecosystem. By the time I was leaving in 2016 the originating application of 2009 had long since ceased to be and yet the general utility of the system was so great that in 2020, over four years after my departure, the system lives on.

I should also note here that from winter 2014 through spring 2015 I made an interesting yet ultimately abortive attempt at powered flight training at the nearby Tipton airport through the Fort Meade Flight Activity club. I learned a lot but for a variety of reasons, spanning my own personal reality and the club’s present state, the experience proved deeply frustrating. In the realm of my personal life, my extended family found itself roiled by end-of-life care drama which provided unpredictable and gut wrenching distractions on a regular basis. In the realm of my professional life, my project was presently experiencing “catastrophic success” which made for an incredibly intense and unpredictable work schedule. In the realm of the flight training experience itself, many factors aligned against me: the time of year I started made for irregularly flyable weather, my size limited the aircraft and instructors available to me, one of the three aircraft that fit me went out of service when an instructor rolled it on an inclement day, another one became unusable for me when the seats were replaced with non-adjustable ones that left me without adequate headroom, the Chief Maintenance Officer quit in frustration for want of resources shortly after I joined, the airport existed in both a cut-out of BWI’s class B airspace and the DC Special Flight Rules Area which created a lot of lesson setup overhead, and frankly I had a pretty sub-optimal relationship with my instructor. Eventually I realized that what I thought meritorious persistence was in fact dangerous stubbornness and I bookmarked this life project for a later date.

In the summer of 2016 I decided to pack up my life in Maryland and head to Connecticut to join Bridgewater Associates in their “Technology Strategy & Incubation” group. My 2.5 years at Bridgewater would provide incredible personal, professional, and technical growth, and I truly cherish having had that opportunity, but also it would prove a period of great turmoil, perhaps owing to a combination of too much coincident change and too little downside risk management on my part. In August I signed a year’s lease on a house in CT whose size I rationalized on the basis of an anticipated engagement and whose location I rationalized on the basis of a Bridgewater renovation-and-relocation project, in December I got engaged over the holiday season, upon returning from vacation my boss/hiring-manager abruptly quit the company, shortly thereafter the TSI group imploded, I then found myself re-org’d into the Security Department which was actively wrestling with what relationship it wanted with inhouse software development, in the spring my fiancée came from out of state to move in with me and take a local job, then I heard that the Bridgewater renovate-and-relocate project was going in a different direction, and by the summer the people who had encouraged me to join Bridgewater had left the company.

Oof. Somehow despite all of this I did manage to build some useful technology that had a meaningful and lasting impact. I also forged many very meaningful friendships that persist to this day. The high integrity and low latency feedback you get at Bridgewater is nothing short of awesome. But hot damn did I do a poor job of rate limiting how many things were simultaneously changing in my life and emplacing escape hatches if things went sideways. In hindsight I ought have evolved both my Bridgewater engagement and romantic engagement in a more gradual and adaptable fashion.

If all that weren’t enough I also attempted to reboot my powered flight training through Arrow Aviation at the Danbury airport in the Spring of 2017. Getting there was roughly an hour’s slog in each direction. Also it was mentally and emotionally taxing when other circumstances in were life were probably adequate to bring me close to a breaking point. And yet it proved a very positive and promising experience, that is right up until it ended in tears, my instructor getting himself killed in an accident while training with another student. Hot DAMN. Some bucket list projects just gonna play hard I guess…

In February 2019 I decided to part ways with Bridgewater and join the Columbus-based tech startup Finite State. And, like a dumbass, I orchestrated my life completely backwards: first I got deeply embroiled with a company that was having an existential crisis, and then I executed an incremental and messy inter-state move, and then I got disengaged. If you’re going to do all three of those things then really you ought do them in exactly the opposite order I did. With the benefit of hindsight I can see clearly that I ought first have come to terms with the struggles my romantic relationship was having, and then I ought have fully set up the basic life infrastructure to navigate my next chapter, and only then ought I have allowed myself to be consumed by the inevitable insanity that any and every startup company will be. Whoops.

And if that weren’t enough I can see now that the company itself was struggling with an order-of-operations inversion problem of its own by investing too much engineering effort into inadequately market tested ideas. Meanwhile, we were also spreading our engineering capacity across too broad a collection of features, many of which lay outside our areas competitive advantage, while furthermore operating with a team of people who were individually awesome but collectively misassembled. And yet, despite all of this, by the fall it felt like we had turned a corner. In reality, however, many people had reached a breaking point. Within a 48 hour period I suffered the one-two punch of having our VP Engineering announce he was quitting and learning that my youngest brother had succumbed to a long and tumultuous battle with drug addiction. I limped along for another four months, long enough to help the company navigate its next funding round, then gave four weeks’ notice and parted ways with the plan being a sabbatical and a relocation out West.

Of course, the universe having a sardonic sense of humor, a couple of weeks into my notice period the COVID-19 pandemic got into full swing and obliterated life as we all knew it. The downtown Columbus life I had come to love vanished over night. Plans for some terminal enjoyment of Ohio evaporated in an instant (nobody at OSU wanted to cram into the cockpit of a 172 with me so I could finish my training). This was kind of maddening and yet over the coming months I had the headspace to navigate the situation gradually, iteratively, adaptively, and rationally. Owing to a mix of proactive self-assessment and decisions to live beneath my means I was long on available brain cycles and financial resources while being short on complicating encumbrances. Although “see the world” had been a bit derailed I found myself readily picking up consulting arrangements that kept me cashflow healthy as well as professionally, socially, and technically engaged. Things were proving shockingly OK in my own microcosm despite the world at large burning. This felt perversely good all things considered. I waited for the tumult to partially abate, began charting my course to Utah in earnest by late July, and then executed a stressful yet survivable RV trip with three cats across six state in four days in September. Oof. Moving to Utah was terrible but being here has been wonderful. Never before have I felt quite so in control of my own environment and destiny.

Knowing that I wanted to make paragliding part of my life I stacked the deck by moving to the Suncrest portion of Draper which puts me a ~10-15 minute drive from the two flight parks of Point Of The Mountain, one of the best places on the planet for a novice paraglider to learn. I also graciously declined an assortment of intriguing full-time job offers with various former colleagues that I love, preferring instead to maintain my part-time remote consultant modality as I reboot and reorient. And then, having taken three weeks to decompress from the move and rig up some basic life infrastructure I began my training. I scarcely could have asked for a better setup: the weather was flyable practically every day for the first month, I had an assortment of wings available to demo any time I wanted them, I established a great relationship with my instructor, my proximity to the training site made for minimal overhead, and my flexible and low-intensity work schedule allowed me to prioritize a high-intensity paragliding schedule that greatly compounded my ability to learn. This is what stacking the deck looks like. I had my P2 rating inside of two months which opens up a world of possibilities to me and furthermore boosts my confidence about completing my PP-ASEL one day.

For the time being I feel like I’m doing just as I ought be. As I look outward to the coming 1-2 years, meanwhile, I find myself wondering how to stack the deck for subsequent phases. There are so many factors to consider and I want every tailwind I can wrangle. It’s hard to know exactly how our post-vaccine world will look but I have accumulated a lot of strategies, tactics, and heuristics to optimize my chances of happy outcomes. I just have to remember to play every facet of the game and sustain my battle rhythms at every level of this fractal reality.

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