Training for Chaos

We don’t rise to the level of our plans. We fall to the level of our preparation.

In the last chapter I talked about training the engine, building general physical and mental capacity rather than just specific skills. That alone isn’t enough, though. What happens when the plan vanishes, when you’re under pressure, short on time, and forced to act without hesitation? That’s when preparation has to become instinct.

I learned this firsthand as a U.S. Army paratrooper. Before you ever board a plane, you train on the ground for weeks, drilling every movement until it’s embedded: how to hook up your static line, how to check your gear, how to exit, how to land. You jump from towers, you simulate the aircraft, and you practice failure, not because you want it, but because it’s coming.

You want to fail when you’re four feet off the ground, not 800.

We don’t take our first flight until the basics are second nature, because stepping out the side door of a C-130 at 800 feet, in pitch black, is against every self-preservation instinct you have. In that moment you don’t want to be thinking through a checklist. You want to be moving. If your main chute doesn’t deploy, you have 9 to 10 seconds to respond before impact, and there is no time to think in that window. You just act.

I still remember my first jump: the roar of the engines, the rush of the open door, and then standing up, hooking up, and waiting for the green light. I didn’t feel fear and I didn’t feel stress. I felt clarity. I knew what to do and I executed, because we had trained for it.

That same mindset exists in the best teams, even in tech. At Netflix, Chaos Monkey was built to deliberately shut down random services in production, so that both the systems and the people would learn to adapt under pressure. They didn’t just hope their systems were resilient, they trained them to be, and the results were measurable. Netflix prevented 80% of potential outages through the learnings surfaced by Chaos Monkey and the broader chaos engineering discipline. These weren’t hypothetical flaws. They were real vulnerabilities, caught early because someone had the courage to test failure on purpose. That wasn’t sabotage, it was preparation. You don’t find out whether you’re ready in the middle of a real incident, you find out beforehand, if you’re willing to simulate the storm.

You see this in sport, too. During the CrossFit Open, athletes receive surprise workouts announced just days before competition. Movement patterns shift, equipment combinations vary, and sometimes it’s a short, explosive sprint while other times it’s a long, grinding engine test. You don’t know what’s coming, and that’s the point. The unpredictability isn’t accidental. It reflects one of CrossFit’s founding principles: prepare for the unknown and the unknowable. In real life, just like in combat, product development, or incident response, you don’t get a playbook with advance notice. You’re asked to perform under pressure, with incomplete information and limited control.

By designing chaos into the format, new standards, awkward movement pairings, strange pacing demands, CrossFit forces athletes to confront not just their physical readiness but their emotional and mental adaptability. The top performers aren’t just strong, and they don’t just move well. They stay composed when the plan disappears. That’s the test, and that’s the transferability. The Open doesn’t only reward fitness. It rewards clarity under fatigue, pacing under uncertainty, and strategy when the rules shift. The chaos is the feature, not a bug, and it reveals what structure alone can’t.

This belongs in the same category as paratrooper training or chaos engineering. You don’t need bullets or breakage for chaos to be real, all you need is volatility, pressure, and a demand for action. When that moment comes, the best don’t panic. They breathe, they move, and they decide.

I want to pause here and share something personal. I’ve never claimed to have done the hardest thing in the military. Many others have faced more direct danger, made life-or-death decisions in the field, and carried far heavier loads, and Nate Fick, whose story I referenced earlier, is one of many. But I’ve also learned that you can’t live your life comparing hardships. Chaos shows up in many forms, and every one of us has moments when our training is tested by stress.

For me, that came during my deployments in support of Operation Enduring Freedom and Operation Iraqi Freedom, where I served as an intelligence analyst in two Combined Air Operations Centers, first at Prince Sultan Air Base in Saudi Arabia and then at Al Udeid Air Base in Qatar. My job was to represent U.S. Army interests in daily joint targeting and mission planning, to advocate for the air support our soldiers needed downrange. That meant walking into rooms where I was often the lowest-ranking person present, trying to secure limited airframes for missions that couldn’t afford to fail. There were more missions than aircraft. Everyone in the room wanted to help, but everyone had missions to support. The real pressure wasn’t the data. It was the conversation, the negotiation, the weight of knowing that if I couldn’t make our case clearly, the soldiers downrange might not get the support they needed.

That stress taught me the true value of clarity, not just in numbers but in stories. It wasn’t the PowerPoint or the packet that made the difference. It was being able to explain why this mattered, what the risk really was, and who would be impacted if we didn’t act. I learned young, and under pressure, how to speak across rank and service, how to translate intelligence into insight, and most importantly, how to give a shit, loudly, clearly, and with purpose.

I didn’t have a name for the motto then. As I shared in the prologue, the words live on the patch of VMM-364, the Purple Foxes, and I would learn the squadron’s history later in my career. But under the load of those rooms in the CAOCs, the principle was already running the work.

One of the awards I received, the Army Commendation Medal, noted that I served in multiple roles normally held by ranks far above mine, including as the BCD Intelligence NCOIC (a Sergeant First Class role) and as an Intelligence Plans Officer, a position typically held by a Major. I don’t say that to boast. I say it to underscore this: you don’t perform under stress unless you care deeply about the mission and the people it impacts.

That lesson stayed with me in uniform, in product, and in leadership. It’s not process that drives you when the pressure hits. It’s principle, it’s preparation, and it’s the ability to act with conviction because you know exactly what’s at stake. You don’t have to be on the front lines to know what chaos feels like. You just have to care enough to move when it matters most.