Becoming
This is the introduction to my book, How Hard Could It Be? How AI Compounds the Experience You Already Have, Available now in paperback, hardcover, and Kindle from Amazon.
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Let me tell you about two military officers.
The first wanted to see combat during a war. Instead, he was assigned to coach football, because he happened to be good at it. He spent the years after his country’s first major war of the century training other men to fight while never deploying himself. He graduated 61st in his class at the military academy, known more for mischief and demerits than academic distinction. The cadets liked him. The military wasn’t sure what to do with him.
When the coaching ended, he was shuffled into staff work: administrative roles, logistics planning, the kind of assignments ambitious officers avoided because they led nowhere. He was good at them. That was part of the problem. He kept getting assigned to more.
He was sent to a remote posting under a brilliant but eccentric superior who saw something in him that the Army’s bureaucracy didn’t. For three years, this mentor conducted what amounted to a private graduate education: assigning readings in military history and philosophy, testing his protégé daily, re-fighting the great battles of the past to study what went wrong and why. The mentor could feel a future conflict coming, embedded in the very treaty that had ended the last one. Rather than pull up the ladder behind him, he decided to prepare this young officer for the thing he could sense but not name.
After that posting, things didn’t improve. The officer was assigned to serve under one of the most difficult personalities in the military, a man of enormous ego who would later dismiss him as his “clerk.” He spent seven years under this superior, in a remote assignment far from the centers of power, working on problems that seemed peripheral and thankless. Building an army for a country that didn’t have the budget, the equipment, or the institutional knowledge to support one.
Over the course of his career, he had spent 16 years at the rank of major. His classmates had advanced steadily through combat postings and prestigious commands. He had coached football, clerked for generals, and built someone else’s army on the other side of the world. His résumé looked, to anyone scanning it quickly, like a career that had stalled.
He couldn’t articulate what made him valuable. Nobody around him could, either.
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The second officer designed something that had never existed before.
Not a weapon. An architecture: a framework for coordinating the military forces of multiple nations, across multiple branches of service, under a single strategic direction. The forces he orchestrated spoke different languages, followed different doctrines, answered to different governments, and in several cases openly despised each other. The political leaders he answered to had competing agendas. The generals under his command included some of the most brilliant and most volatile personalities of the century.
On the evening of June 4, 1944, that architecture faced its ultimate test.
The original invasion date had been June 5. That morning, the weather over the English Channel was so violent that the officer had already postponed the operation once, recalling 5,000 ships that were already at sea. That postponement was itself an enormous decision. You can’t hold an invasion force in suspended animation indefinitely. Across the staging areas, 160,000 troops were packed into ships, seasick, anxious, waiting for an order that hadn’t come.
That evening, his commanders gathered in the library of a country house near Portsmouth. They sat in easy chairs and on sofas, which gave the room a surreal, almost domestic quality for what was about to become the most consequential military decision of the century. Rain lashed the windows. The chief meteorologist delivered a slightly improved forecast: a possible window on June 6, maybe 36 hours of manageable weather before conditions deteriorated again. Not good weather. Manageable weather. The distinction between those two words was 160,000 lives.
The officer made a preliminary decision to go. Then he tried to sleep. He didn’t sleep well. He was a chain smoker, and the accounts from that night suggest he was going through cigarettes constantly.
At 3:30 in the morning on June 5, he returned to the same library. Same commanders. Same easy chairs. The meteorologist confirmed the narrow window was still holding.
The room was quiet. The officer paced, hands clasped behind his back. His ground commander wanted to go. His air commander warned that conditions were marginal for the bomber and fighter support the landing needed. His naval commander needed a decision immediately; the ships required lead time that was running out.
Everyone in the room watched one man pace.
The silence lasted what multiple witnesses later described as minutes. Not seconds. Minutes.
He had already written a letter taking full responsibility for the failure. “Our landings have failed to gain a satisfactory foothold and I have withdrawn the troops. My decision to attack at this time and place was based upon the best information available. The troops, the air and the Navy did all that bravery and devotion to duty could do. If any blame or fault attaches to the attempt it is mine alone.” He had folded the letter and put it in his jacket pocket. He misdated it July 5 instead of June 5. A man under enough pressure to accept total responsibility for the largest military operation in history, and his hand wrote the wrong month.
He stopped pacing. He looked up.
“Okay, we’ll go.”
That decision wasn’t tactical brilliance. It was the product of everything those decades had built: the ability to hold military, political, and logistical dimensions simultaneously, synthesize competing inputs from people who disagreed with each other and with him, and translate strategic intent into a decision clear enough that people were willing to stake their lives on it. He didn’t execute the plan. He specified what needed to happen with enough precision and conviction that an operation involving 160,000 people across five beaches could execute it without him weighing in on a single tactical decision once it began.
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Both officers graduated from West Point in the class of 1915, later called “the class the stars fell on.” Of the 164 graduates, 59 eventually became generals. Two earned five-star rank. One became president.
The second officer was Dwight D. Eisenhower. Supreme Allied Commander. Architect of Operation Overlord. Later, president of Columbia University, Supreme Commander of NATO, and the 34th President of the United States.
The first officer was also Dwight D. Eisenhower.
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If you caught that before the reveal, if you started connecting details across two seemingly separate stories and recognized they fit together, pay attention to how you did it. You made a connection that wasn’t stated, using partial information from different contexts.
That’s the skill this book is about. You just don’t usually apply it to military history.
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Have you ever had an idea you could see so clearly it felt like it already existed?
Not the outline of an idea. The whole thing: the architecture, the logic, the way the pieces connected. Sitting fully formed in your head. You could describe it to anyone and they’d nod. You could see the problems it solved and the specific way it solved them. And you had absolutely no way to get it out into the world.
Maybe it was a product your company should have built. A business you kept sketching on napkins. A system you knew would work if someone would just build it. The gap between what you could see and what you could make was enormous, and nobody around you seemed to understand why that gap mattered, because they couldn’t see the thing you were seeing.
I’ve had two ideas like that. Let me tell you about the first one.
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Over 10 years ago, I had an idea for a grocery distribution concept that I could see down to the operational details. Neighborhood pickup points instead of expensive retail space or the nightmare of last-mile delivery. A check-in system where you’d pull up in your car the way you do at IKEA for order pickup. Website filters that would let a parent remove every product containing high-fructose corn syrup, or build a curated snack list their kids could choose from without prices. Ad-supported pricing where the marketing revenue went directly to the shopper. I could see the architecture of the whole thing, every layer, every connection.
I couldn’t build any of it.
I didn’t know how to make a website. I didn’t have a developer. I didn’t have capital. The actual thing, the working product, the proof that this wasn’t just a fantasy, required skills and resources I didn’t have. I was staring right at a better approach. And I couldn’t touch it. That was the wall. Not capability. Access.
The idea withered. Not because it was wrong. Because the wall was too high for me to climb.
I filed it away. I moved on. I built a career across law, product management, and compliance sales. I started two restaurants (one failed, one running profitably) and a six-figure Amazon book business. I kept seeing problems and building what I could to solve them. But the grocery concept stayed in my head as a reminder of the category of ideas that required teams and capital. The ideas one person couldn’t will into existence no matter how clearly they could see what needed to be built.
If that feeling is familiar to you, this book is for you.
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Eisenhower graduated 61st at West Point. After his mentor’s three years of private education, he attended the Command and General Staff School at Fort Leavenworth, where most of his classmates had the infantry experience and combat credentials he lacked. He graduated first in a class of 245. By 1943, he’d been chosen over 400 senior officers because his scattered career turned out to be exactly the preparation the moment demanded. The context shift was a world war. The role it created had no precedent. The person who filled it was built by decades of experiences that looked like dead ends while he was living them.
You don’t need a world war for a context shift. You just need the wall between intent and execution to come down far enough that what you already know becomes what you can build.
The context shift happening now is artificial intelligence. And the roles it’s creating don’t have established names, career tracks, or training programs yet. They’re being filled, right now, by people whose careers look random on paper. People who’ve accumulated skills deep in one domain or across domains that don’t obviously connect. Until they do.
You may be one of those people. You may not know it yet, the same way Eisenhower couldn’t have known it during his 16th year at the same rank. I didn’t know it either.
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A decade after the grocery idea died, something had changed. The gap between intent and execution, the gap that killed my concept, had collapsed. Not for everything. A grocery distribution network still requires warehouses, leases, trucks, and labor. AI didn’t change the physics of atoms. But for anything that could be specified in language and built in software (information systems, analysis workflows, coordination tools, digital infrastructure) the wall had become thin enough to push through, if you knew how to push.
And knowing how to push didn’t require knowing how to code. It required knowing how to think.
I built my own AI infrastructure from scratch. A multi-agent system on hardware I controlled, with agents I specified, processing my information, automating my workflows, operating autonomously while I slept. In under two weeks. Part-time. While working my day job. I still can’t write a Python function from scratch.
Last week, I nearly shipped a company-wide pricing model updated by AI to my team that had data that was visibly wrong in a way that I should have caught in thirty seconds. I didn’t catch it because I’d stopped looking. That’s not a beginner’s mistake. That’s a thinking mistake.
That was my second idea: not just the system, but this book. The realization that what made the build possible wasn’t anything technical. It was a career’s worth of seemingly random experience (law, product management, compliance, sales, scuba diving, restaurants, a six-figure side business) that turned out to be exactly the preparation this moment demanded. I wrote this book to show you what I mean.
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What Eisenhower did on the largest stage in human history, you do on yours. Every complicated project, every team you’ve managed through chaos, every time you sat with a problem until the pieces fit: that’s the same skill. The difference between then and now is that for the first time, clear specification can become a working system without a team, a budget, or a decade of institutional support. The wall between intent and execution has come down. What’s on the other side is the subject of this book.
The temptation is to stop at the surface. Download a tool, ask it questions, get faster at the things you’re already doing. Most people do that and never look further. This book is about what’s on the other side.
You have a life’s worth of jobs, experiences, skills, judgment, and pattern recognition that you may think have nothing to do with artificial intelligence. That cross-domain breadth is the raw material. It’s what allows you to see a whole problem, not just the technical dimension but the business dimension, the human dimension, the legal dimension, the operational dimension, the way Eisenhower could hold military, political, logistical, and human factors simultaneously.
The discipline that turns that raw material into capability is precision. Defining what should exist clearly enough that capable agents, human or machine, can execute it without you weighing in on every decision. That discipline has always existed in law, in engineering, in military planning, in product management, in a kitchen where the owner knows what good pizza looks like without ever having stretched the dough. AI just made it the most consequential version of itself.
You already have the hard part. This book is about what to do with it.
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If this introduction resonated, the book goes deeper — through Eisenhower, Bell Labs, Kodak, the Brooklyn Bridge, and my own experience building sovereign AI infrastructure. It’s a thinking framework, not a prompt guide. How Hard Could It Be? How AI Compounds the Experience You Already Have is available now on Amazon in paperback, hardcover, and Kindle.