On the twenty-fifth of May, Pope Leo XIV did something popes do not usually do. He showed up in person to present his own encyclical. The subject was artificial intelligence. And standing near him, as the document was introduced, was not a cardinal but a co-founder of one of the most powerful AI companies on earth.

What that founder reportedly told the Pope was not that AI would save us, or doom us, or change everything. He said the machines his company builds contain behaviors that are, in his word, unsettling — things that even the people who make them cannot fully explain.

Sit with that for a second. A builder went to one of the oldest moral authorities in the world and said, in effect: we made this, we do not entirely understand it, and we did not want to be the only ones thinking about what it means.

Now close that tab and open LinkedIn.

A different mindset is waiting for you there. AI as the next Gutenberg. AI as the next fire. AI as a new form of life. Founders posed beside their products like prophets beside stone tablets. Consultants who became “AI strategists” sometime in the last ninety days, certain to the decimal point about a technology that did not exist in their bios a season ago. The voice is absolute. The certainty is the product. And scroll a little further and you find its mirror image — the prophets of doom, just as loud, just as sure, certain the same machine is the end of work, the end of truth, the end of us.

The evangelist and the doomer look like opposites. They are not. The evangelist says the tool will save you. The doomer says it will damn you. Both of them hand the tool a power it does not hold on its own. Both are a kind of magical thinking — the machine as a god, to be worshipped or feared, rather than a thing that does what the hand holding it intends.

You can hear it in the language. AI is the new fire. But no one ever asked you for your fire strategy. No one asks for your wheel strategy, or your electricity strategy. The wheel remade every civilization that ever touched it, and still, nobody stood on a stage to tell you it would save you or end you. They asked where you wanted to go. That is the question both the believers and the doomsayers skip, and it is the only one that has ever mattered. Not what the machine will do to us. Where do you want to go.

There is a third posture, and it is the rarest one. It treats the tool as exactly what it is. Powerful. Consequential. Useful or harmful depending entirely on the intent behind its use, and worth handling with the care you’d give anything that can do real damage. That was the posture standing next to the Pope — a man saying, out loud, that he did not fully understand the thing he had built. It is almost never the posture that goes viral.

The skeptic has an answer ready for all of this, and I want to give it its due. The Vatican appearance, the skeptic says, was theater. Soft-power repositioning by a company under political pressure at home, buying a little moral legitimacy in Europe. That reading is in print, and it is not stupid.

Maybe it’s both. But the test of a posture is never the motive behind a single gesture. It’s whether the behavior holds up when consistency starts to cost something. The same company refused the Pentagon’s demand for unrestricted military use of its tool. It has delayed its own products over safety concerns. Humility that keeps costing you contracts and revenue starts to look less like a strategy and more like a spine.

I should say plainly that I use these tools — a lot of them, from several companies, including the one that stood beside the Pope — in my own work nearly every day. I find them genuinely useful. I also refuse to let any of them write in my voice, and I think the hype around them is doing real damage. That isn’t a contradiction. It’s the whole point.

But I don’t want to hand you my verdict on who’s right in Rome. A verdict is just one more thing for you to accept or reject — one more posture handed to you by someone who sounds sure. What I’d rather offer is the way I actually take a story like this apart when it crosses my feed. Because the same habit that keeps me from being sold a bad AI strategy at work is the one that lets me read a spectacle like this one without being spun by either side of it.

So here is what I find myself asking, more or less in order, before I let a headline like this land on me.

First: what does each person actually want? Not what they say they want — what the situation rewards them for wanting. The evangelist needs you certain, the doomer needs you afraid — and both need you to believe they’re the one who can see what you can’t. The founder beside the Pope wants cover, maybe. Or maybe, genuinely, help. I don’t have to settle it. I just have to ask, because the answer quietly changes what every word that follows is worth.

Second: does the structure hold? Strip the claim down to its bones and see whether it stands on its own. “This tool will change everything” has no bones — it’s a feeling wearing a prediction’s clothes. “This tool does these specific things, and here is what we still can’t explain about it” has bones. You can stand on it. You can build on it. The difference between the two is the difference between being told something and being shown something.

Third: does the behavior match the words? This is the question most people skip, and it’s the one that does the most work. Anyone can stand next to a Pope for an afternoon. Fewer will turn down the Pentagon when the check is right there to be signed. So I watch for the thing that costs the person something to do. That’s usually where the truth is hiding — not in what they say, but in what they were willing to pay.

None of that tells me who to root for. That isn’t its job. It tells me what I’m actually looking at. And once you can see what you’re looking at, the people trying to sell you certainty — in either direction — lose most of their grip on you.

The machine in front of me happens to be AI. But the habit doesn’t care what the machine is. It works on a stock tip, on a campaign promise, on a headline built to make you afraid before you’ve finished reading it. Anywhere someone arrives already certain and needs you certain too, the same questions apply, and the same grip loosens.

A founder stood beside the Pope and admitted he didn’t fully understand the thing he had made. A thousand other people posted their certainty this morning. I’m not going to tell you which of them is right.

I’m going to tell you that the difference between them is visible, if you know what to look at. And that learning to look is the closest thing I have found to a defense against an age that would very much prefer you didn’t.

Holding the Edge is about how mathematicians see the world — without the math. A new essay every couple of weeks.

I’m also on LinkedIn, where I post these and think out loud between essays.

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My great-uncle had been a judge in Cuba.

By the time I was a boy in Las Vegas, he was learning to deal blackjack at my father’s coffee table.

He was not the only one. Several nights a week, our living room filled with men who used to be other things — doctors, lawyers, professors, accountants — and were now learning the only skill the city would pay them for. The skill my father had. He had been a casino manager in Havana before the revolution. He was a baccarat dealer at Caesars Palace now. The men who came to our house came because he could teach them how to get hired.

Where other families had a coffee table with magazines on it, mine had a felt with cards laid out on it.

My mother would put coffee out. The men would arrive after dinner. My father would set up two or three games — usually blackjack, sometimes baccarat — and walk each man through the moves. How to pay attention to the count. How to manage the chip stack. How to read the room without seeming to. How to be invisible enough that a casino floor would trust you with its money.

Most of them learned. Some of them did not. The casino floor was not for everyone.

The ones who did got jobs at the Sands, the Riviera, or the Sahara. The ones who did not went back to whatever else they could find.

I was the youngest student in the house, by about thirty or forty years.

I would sit at the edge of the felt, eight years old, and watch a man who used to run a hospital in Havana learn to fan a deck. I would watch my great-uncle — a man who had handed down sentences in a Cuban courtroom — practice the patter a blackjack dealer uses to keep a table loose. I did not yet have the words for what I was seeing, but I knew it was something specific. These were not the easy hours of men who had always been who they were. These were the hours of men who had become someone else, in a hurry, because the country they had been someone in had stopped existing.

My father moved through the room like a man who had done all of this before. He had. He was patient. He was specific. He would correct a hand and explain why. He would tell a man who had been a surgeon that his cards were giving him away, and the surgeon would nod and try again.

When the men left for the night, my father would let me stay up. He would pull out a deck for me. We would play hands until I made enough mistakes that he could teach me something. He never softened the lesson. He would explain the math behind a hand the way another father might explain how to fix a car. The odds were not a comfort or a punishment. They were a fact. You could read them or you could fail to read them. The choice was yours; the math did not care.

One evening — I must have been nine — I asked him the question every boy at a card table eventually asks his father.

“Dad, is there a system? Is there a way to beat the house?”

He stopped what he was doing. He was shuffling eight decks for baccarat, the way he had to practice every week to keep his hands sharp. He looked at me for a moment, the way a man looks when he is deciding how much truth a child can hold. Then he said:

“Son, if there was a way to beat the house, we wouldn’t be having dinner tonight.”

I did not understand him then. I understand him now.

The house has the edge. Always. It is built that way. The house does not survive on luck; it survives on a small, persistent, structural advantage in every game it offers. The way to win, in a casino, is not to beat the house. It is to know exactly what the house is doing, and then to make decisions that respect that knowledge instead of pretending it isn’t there.

What my father was teaching at the coffee table — to my great-uncle and the surgeon and the lawyer and the schoolteacher and the small son sitting at the felt’s edge — was not how to win. It was how to see. How to look at a game, or a room, or a country, or a life, and read the structure underneath it. The men who learned how to see prospered.

The lessons did not feel like lessons. They felt like evenings. Cards being shuffled. A man laughing at his own mistake. The smell of coffee. My mother in the kitchen. The fluorescent light over the felt.

What I know now is that those evenings were a school. The school had no name, no diploma, no tuition. The only credential was that you had lost the country you were born in, and you needed to learn a new way to feed your family.

My father, who never went to college, ran the school. He didn’t think of it that way. He thought he was helping his friends.

But the men who came to our house in those years learned something larger than blackjack. They learned that you can read your way back into a life — that structure exists underneath every foreign situation, and if you can find the structure, you can find your way.

Forty years later, every time I sit down with a client, a colleague, an executive trying to make sense of an environment they do not yet understand, I am sitting at my father’s coffee table. The men who learned at that felt are mostly gone now. Some of their children went on to do things their fathers could not have imagined. My great-uncle the judge spent the rest of his career in a Las Vegas casino, and he was good at it.

The school is closed. The lessons are still being taught.

I keep teaching them.

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The air conditioner blew up last month.

Middle-of-summer chaos. I called three HVAC companies. Each one came out, walked through the house, measured what needed measuring, and a day or two later emailed me an estimate. Specific brands. Specific tonnages. Three different proposals.

A day after the last estimate landed in my inbox, my wife was scrolling Instagram and asked me a question.

“Is this the unit from one of your estimates?”

I read over her shoulder. It was. The exact model, the exact brand, the exact unit that one of the contractors had specified in an emailed proposal that landed on my computer, in an account she does not use.

I had not searched for that model online. I had not posted about it. The only place that brand had been spoken aloud was on a phone call with one contractor, standing in my kitchen, while my wife was in another room.

It was on her feed within twenty-four hours.

We laughed about it for a moment — the kind of nervous laugh you do when you realize a thing has been listening that you hadn’t formally invited in. Then I went back to my desk and sat with it.

Technically, somewhere in a policy I once clicked through, I had agreed to this. Technically, the fine print covers it. But the honest reaction, sitting at my desk, was that it felt gross. Intrusive. A little bit dishonest. The system wasn’t trying to engage me thoughtfully. It was trying to slip under the radar of my consciousness and earn a thoughtless click.

And the alternative — opting out of every cookie, every permission, every tracking allowance — would render half the internet unusable. So the choice on offer is: be manipulated, or be locked out. That is not really a choice. That is a designed environment.

My father would have known what to call this. He spent thirty years inside engineered environments. He could read a casino the way a structural engineer reads a building. What’s load-bearing. What’s decorative. What’s there to keep you from looking at something else.

He understood that the casino’s edge was not the odds, but the disorientation. The free drinks, the missing clocks, the windowless rooms — the architecture was never hidden. It was just unobserved by people who had not learned to see it.

What my wife had caught on her feed was the same architecture, refined for a different medium, reaching across a network my father could not have imagined into a household it had no formal invitation to enter.

The casino used to require you on the floor.

Now it follows you home.

Once you start seeing it, you see it everywhere.

I rarely open Instagram — once a week, maybe, and usually because my wife has sent me something and told me in person to go see it. I open the post, watch the thing she sent, and look up thirty minutes later with no idea what I had been looking at. Engineers were paid to make that happen.

Earlier this year I went to sign up for an account with Anthropic. I wanted to use Claude for some work I was doing. I typed a search, clicked the top result, and within a few minutes had paid for a service. Except the service was not Anthropic. It was a reseller offering access to a dozen different AI models at a price considerably higher than Anthropic charges directly.

The page was not technically lying. Claude was, in fact, one of the models the reseller offered. But the context had been engineered away. I had not asked myself, before I clicked, what I actually wanted. An account directly with Anthropic. No intermediary. At the price Anthropic charges. If that had been the sharp instruction in my head, no top-of-search reseller could have caught me. They caught me because I gave them a fuzzy target to aim at.

I canceled the charge. Found the actual site. Signed up. Lost an hour to it.

And reminded myself that the architecture is only half the story. The other half is me.

The pattern is the same every time. A fact that is technically true, stripped of the context that would change what you do with it. The HVAC unit on my wife’s feed. The reseller offering Claude. The Instagram post that was technically what I opened the app to see. The architecture around each of those facts was built to take something from me. Money. Time. Attention. A decision I would not have made if I had seen the whole picture.

Time is the one thing none of us gets more of. When it’s gone, it’s gone.

I learned this earlier in my career. When I traveled for work, my oldest daughter — still small — would cry when I left on a trip. I could see the cost of lost time in her face and it broke my heart. The phone in my pocket, whether it was work email or a feed, was time away from her. That’s not an abstract loss. That’s a deeply personal loss.

A few years ago I made a different bet. I committed to listening to an audiobook every time I walked the dog. By the end of that year I had finished seventy books. Time is an asset. It is worth what you invest in it. The only real question is whether you are investing it — or chasing some bouncing ball a marketer wants you to follow.

The casino at least bought you a drink for what it took. The architectures we live inside now take your time and give you nothing back. There is a level of theft happening here that puts the casinos my father knew to shame.

Lies, too, are engineered environments. You read them the same way. First question: what are they after? Then: what’s distraction, and what’s substance? Then: what’s the context that’s been removed — the one that would change what I do?

My father saw what most people could not see. He was paid to. The casino floor was his classroom, and he taught me to read it.

The classroom has moved. The architecture has not.

The first move is the same one it was at our coffee table forty years ago: learn to see the room you are standing in.

Whatever room that turns out to be.

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A casino is the most carefully designed room you will ever stand in. The drinks are free on the gambling floor. There are no clocks anywhere. There are no windows, and no daylight to anchor you to the world outside. The TVs upstairs play training videos on how to play the games, so you don’t stay in your hotel room. By the time you have been on the floor for three hours, you don’t know what time it is, you don’t know what you have spent, and you have been having a great time the whole way down.

None of this is accidental. Every element is engineered to lower your executive function. Free drinks dull judgment. No clocks remove the prompt to leave. No windows remove the reminder that a real day is happening outside the building. The shining lights, the chatter, the dealers who treat you like a high roller — all of it works together to disorient you, on purpose, because a disoriented person stays at the table, chasing the excitement.

I grew up around Las Vegas in an era when the manipulation was the whole business. Some of today’s casinos have dialed elements of it back, but many still operate the way they did when I was a kid, and the underlying architecture has not changed even where the surface has softened. The room is still designed to keep you in it.

I have walked through casino lobbies at six in the morning, on my way out to go rock climbing, and seen kids asleep on the carpet because their parents had lost track of time. I have walked past people on payphones explaining to someone they love why they have spent everything. The hotels have special arrangements with credit cards because cash advances to keep gambling routinely max out credit limits, making it impossible to pay the hotel charges.

Most people assume the casino takes their money on the odds. It doesn’t. It takes their money on the iterations.

A slot machine advertised at 98% payback returns ninety-eight dollars on every hundred you put in — over a very large number of trials. Inside a single evening, you do not get a very large number of trials. You get streaks. The streaks cancel out in the long run, but you do not live in the long run. You live in tonight, with a fixed bankroll. When the streak goes against you, you bust out, and the trial ends. The casino has infinite money and infinite patience. You do not. That is the asymmetry. They never bust out. You eventually do.

When I talk about structure, this is the math. A casino is built explicitly on it — every game’s odds, every payout percentage, every comp threshold. But every structure is the math through which we operate and process information, whether we have named it or not. Math is the structure. The casino has just made the structure visible by building a room around it.

In graduate school, my friend and I drove up from Tucson to visit family in Las Vegas. We were starving students. We met up with some guys who had been watching the Lakers and the Celtics, and one of them said, let’s go play craps and make a lot of noise. We pulled up to a Caesars Palace table with a twenty-five-dollar minimum, looked at each other, and walked back out. Then one of the guys said: let’s go across the street to Little Caesars.

Little Caesars had a fifty-cent crap table.

My friend and I each put forty dollars on the table. We agreed: when the forty dollars are gone, we leave. We played for four raucous hours, we yelled, we acted like high rollers on a fifty-cent table, we made bets for the boys, we had one of the funnest nights of our lives. Eventually the forty dollars were gone. We left.

The architecture did not change between Caesars Palace and Little Caesars. The free drinks were still free. The clocks were still gone. What changed was that we walked in knowing exactly what we were doing. We were buying an evening of entertainment for forty dollars apiece. We were not trying to make money, we were not trying to recoup anything, we had no interest in the math of the house. We had named our intent before we entered the room, and once intent was named, the structure lost its grip. When the money was gone, the evening was over.

Same architecture. Same math. Different intent. Once intent is named, the structure loses its grip.

The casino is the easiest version of this story to see, because the architecture is so visible. The clocks are obviously missing. The drinks are obviously free. But the same structure operates everywhere you look, once you know what to look for: apps designed to hold attention, feeds designed to confirm what you already believe, environments designed to make a story feel like a fact. They work for the same reason the casino works. You don’t notice the design, and you haven’t named what you are there for.

The first move of any decision practice is learning to see the room you’re standing in.

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That question is what this newsletter is about. And the answer starts with understanding that uncertainty isn’t a problem to be solved. It’s a spectrum we all live on — and one that must be navigated with courage.

A casino is designed to make you feel one thing and bet on that feeling. The odds are calibrated with mathematical precision to ensure that money flows in one direction — into the house. Everything about the environment — the sounds, the lights, the near-misses, the occasional winner paraded through the floor — is engineered to make you trust your instincts instead of the statistics. Understanding those statistics won’t make you rich. But it will keep you from making decisions based on feelings that were manufactured by someone who profits from them.

That’s one end of the spectrum.

At the other end, astronauts were climbing into a spacecraft and pointing it at the moon. The uncertainty was enormous — the risks, the distances, the engineering tolerances that had to be perfect or people would die. But they didn’t navigate that uncertainty by trusting their gut. They charted a careful plan built on understanding every risk, every variable, every possible failure. We saw the power of that discipline with Apollo 13. When the oxygen tank exploded and the crew was in danger of being lost in space, the teams on the ground didn’t panic. They replicated the situation. They ran every scenario. They tested. They argued about the options and measured the tradeoffs. And they brought three astronauts home safely — not through luck or instinct, but through the painstaking, disciplined work of understanding the details and having the courage to act on them.

That’s the other end of the spectrum.

But here’s the thing most people miss. Those two extremes — the casino floor and mission control — are not different worlds requiring different skills. They are two points on a single, continuous spectrum of uncertainty. And you live on that spectrum every single day.

You live on it when you open social media and an algorithm feeds you a version of reality that has been concentrated, amplified, and distorted until fringe opinions look mainstream and outrage feels like consensus. There was a time when someone with a crazy idea would stand on a soapbox at Speakers’ Corner in Hyde Park and get an honest reaction from the crowd. The crowd was a natural filter. Now there is no crowd — there is an algorithm, and it doesn’t filter for truth. It filters for engagement. You feel informed. You feel like you’re seeing reality. But the structure underneath what you’re seeing has been designed to keep you watching, not to keep you accurately informed.

You live on that spectrum when you’re choosing a school for your child. You’ve heard things from other parents. The school has a reputation. But do you actually know the details? Where’s the data that tells you objectively whether this school is right for your kid? The information exists. Most people never look for it because the informal narrative feels like enough.

You live on it when a financial advisor puts a product in front of you built on percentages and structures and mathematics so dense that your eyes glaze over — and you sign because the person across the table seems trustworthy and the brochure looks professional. Or at a car dealership, where the salesman floods you with numbers until you sign without noticing the extra half percent buried in the fine print that goes straight to the dealer. That wasn’t an accident. The flood of information was the strategy. We’ve all been there.

There is no escaping uncertainty. It is the water you swim in — at work, at home, online, in every decision where you’re trying to figure out what’s actually true and what just feels true. And in a world that is ruthlessly changing — sometimes for the amazing, sometimes not — the question isn’t whether you face it. The question is whether you have any agency in how you navigate it.

And here’s what makes this moment particularly hard. Everything in our world is pushing us to think less, not more. React, don’t deliberate. Go with the outrage rather than considering the details. Share before you read. Decide before you understand. The pace of modern life rewards speed over clarity, and the systems we interact with every day are designed to accelerate that impulse, not slow it down. It is genuinely difficult to think clearly right now — and the world is not making it easier. You can see it everywhere. People behaving in ways that make no sense. Trusting information that doesn’t deserve their trust. Making decisions based on headlines they didn’t read past and opinions they never examined. It’s not that people are stupid. It’s that the environment is relentless, and without the right discipline, even smart people get swept along.

But what is the alternative? Are we content to turn over our decision-making power to the algorithms, the consultants, the complexity, the noise? Are we willing to let systems we don’t understand make our choices for us — about our careers, our families, our money, our beliefs? Or are we going to stand in that spectrum of uncertainty, learn how it actually works, and find how to make it serve us instead of the other way around?

That is the question. And this newsletter is here to help you answer it.

You’ve heard the phrase “trust your gut.” And there’s truth in it — everyone has to trust their instincts at some point. But it’s a very different thing to trust your gut after you understand the details, after you’ve seen the structures that shape the environment, after you’ve separated what you feel from what the data actually says. That last part is hard sometimes, because we want to act on our feelings. Feelings are fast and they feel right. But the person who checks their feelings against the details and then acts — that person is operating on an entirely different level.

I’ve spent my career doing this work — as a math professor turning students who hated math into people who saw its power, as a technologist sitting with business leaders who had been burned by turning their decisions over to consultants who didn’t understand the details, and as a builder of systems that help organizations trust the data their decisions depend on. If there is one thing I know how to do, it’s this: take the structures that most people find intimidating or invisible and make them clear, accessible, and genuinely useful. That is what this newsletter will do.

And what makes this moment genuinely exciting is that tools like AI now make this kind of thinking more accessible than ever — giving any person willing to do the work the ability to think with a clarity and power that was once reserved for specialists.

That’s what Holding the Edge is about. We’re not here to tell you what to think. We’re not here to dictate your decisions. We’re here to show you how to do what you already do with the greatest level of clarity, understanding, and effectiveness possible — using math, philosophy, data, and AI to help you see what your instincts alone can’t show you.

I hope you’ll join us for this. Clear thinking, in an age when it’s becoming increasingly rare, might be the most valuable skill you can develop. And the adventure of learning it — I promise you — is worth the ride.

Welcome to Holding the Edge.