THE BIGGEST BLUFF
How I Learned to Pay Attention, Master Myself, and Win
Maria Konnikova

Copyright

4th Estate

An imprint of HarperCollinsPublishers

1 London Bridge Street

London SE1 9GF

www.4thEstate.co.uk

This eBook first published in Great Britain by 4th Estate in 2020

Copyright © Maria Konnikova 2020

Cover design by Luke Bird

Illustrations © Geo Images/Alamy; © Anton Shaparenko/Alamy

Maria Konnikova asserts the moral right to be identified as the author of this work

A catalogue record for this book is available from the British Library

Information on previously published material appears here.

All rights reserved under International and Pan-American Copyright Conventions. By payment of the required fees, you have been granted the non-exclusive, non-transferable right to access and read the text of this e-book on-screen. No part of this text may be reproduced, transmitted, down-loaded, decompiled, reverse engineered, or stored in or introduced into any information storage and retrieval system, in any form or by any means, whether electronic or mechanical, now known or hereinafter invented, without the express written permission of HarperCollins

Source ISBN: 9780008270834

Ebook Edition © June 2020 ISBN: 9780008270841

Version: 2020-05-23

Dedication

In memory of Walter Mischel.

I still haven’t published my dissertation,

as I promised you I would, but at least there is this.

May we always have the clarity to know

what we can control

and what we can’t.

And to my family,

for being there

no matter what.

Пусть все будут здоровы.

Epigraph

“Life’s single lesson: that there is more accident to it than a man can ever admit to in a lifetime and stay sane.”

FAUSTO MAIJSTRAL, IN THOMAS PYNCHON’S V.

“I wish you luck, because what lies ahead is no picnic for the prepared and the unprepared alike, and you’ll need luck. Still, I believe you’ll manage.”

JOSEPH BRODSKY, “SPEECH AT THE STADIUM”

“But once in a while the odd thing happens,

Once in a while the dream comes true,

And the whole pattern of life is altered,

Once in a while the Moon turns Blue.”

W. H. AUDEN, LIBRETTO FOR PAUL BUNYAN

Contents

Cover

Title Page

Copyright

Dedication

Epigraph

A Prelude • Las Vegas, July 2017

Ante Up • New York, Late Summer 2016

The Birth of a Gambler • Boston, Fall 2016

The Art of Losing • New York, Fall 2017

The Mind of a Strategist • New York, Late Fall 2016

A Man’s World • New York, Winter 2016

No Bad Beats • Las Vegas, Winter 2017

Texting Your Way out of Millions • Las Vegas, Winter 2017

A Storytelling Business • Las Vegas, March 2017

The Gambler and the Nerd • Monte Carlo, April 2017

The Art of the Tell • New York, May 2017

Reading Myself • New York, May–June 2017

Full Tilt • Las Vegas, June–July 2017

Glory Days • The Bahamas, January 2018

The Heart of the Gambling Beast • Macau, March 2018

The Ludic Fallacy • Las Vegas, June 2019

Glossary of Poker Terms

Footnotes

Acknowledgments

Index

About the Author

Also by Maria Konnikova

About the Publisher

A Prelude
Las Vegas, July 2017

The room is a sea of people. Bent heads, pensive faces, many obscured by sunglasses, hats, hoodies, massive headphones. It’s difficult to discern where the bodies end and the green of the card tables begins. Thousands of bodies sit in seeming disarray on chairs straight out of a seventies dining room catalogue—orange-and-mustard patterned upholstery, gold legs, vaguely square frame. Garish neon lights suspended on makeshift beams make the place look like the inside of a hospital that’s trying a bit too hard to appear festive. Everything is a bit worn, a bit out‑of‑date, a bit frayed. The only hints of deeper purpose are the color-coded numbers hanging on strings from the ceiling. There’s the orange group, the yellow group, the white group. Each placard has a number and, beneath it, a picture of a single poker chip. The smell of stale casino air fills the room—old carpet; powder; a sweet, faintly sickly perfume; cold fried food and flat beer; and the unmistakable metallic tang of several thousand exhausted bodies that have been sharing the same space since morning.

Amid the sensory assault, it’s hard at first to pinpoint why something seems off. And then it comes to you: it is eerily quiet. If this was a real party, you would expect the din of countless voices, shifting chairs, echoing footsteps. But all there is is nervous energy. You can smell, hear, taste, the tension. And you can certainly feel it making a nest in your stomach. There’s just one sound left in the room, reminiscent of a full-throated courting ritual of summer cicadas. It’s the sound of poker chips.

It’s the first day of the biggest poker tournament of the year, the Main Event of the World Series of Poker. This is the World Cup, the Masters, the Super Bowl—except you don’t need to be a superhero athlete to compete. This championship is open to the everyman. For a neat ten grand, anyone in the world can enter and take their shot at poker glory: the title of world champion and a prize that has been known to top $9 million. If you happen to be British or Australian, you even get it tax-free. For professional poker players and amateurs alike, this is the career pinnacle. If you can win the Main Event, you have guaranteed yourself a place in poker history. Sit down with the best and have a chance at the most prestigious, richest prize in the poker world. Some people in the room have been saving for years to take their one shot.

It’s near the end of the day. Of the several thousand people who’ve entered today’s starting flight—so many want to play that starting days have to be staggered into flights to accommodate everyone; the dream is expensive, but it’s awfully alluring—many are now out, having gone bust, in poker speak. The ones who remain are concentrated on making it through to the second day. You don’t want to play the whole day only to find yourself walking out with minutes until the end and nothing to show for it. Everyone is gunning for the magic bag, a clear plastic glorified ziplock into which those lucky enough to have made the next day of a multiday tournament can place their chips. You write your name, country of origin, and chip count in excited capitals on the outside before tugging on the dubiously functioning adhesive strip to seal the damn thing up. You then take the requisite photograph for social media with the requisite chip count and add the #WSOP hashtag. And then you collapse, exhausted, into some anonymous hotel bed.

But we’re not yet at the bagging and tagging stage of the day. There are still two more hours to go. Two whole hours. A lot can happen in two hours. Which is why one table stands out from the rest. Eight players are sitting as players should, receiving their cards and doing whatever it is poker players do with them. But one lone chair in the middle of the table, seat six, remains empty. That wouldn’t be remarkable in the least under normal circumstances—empty chairs are what happens when a player busts out and no new player has yet arrived to take their place. Except in this case, there has been no bust-out. On the green felt in front of the empty chair sit several neat piles of chips, arranged from highest to lowest denomination, color-coded from left to right. And with each hand dealt, the dealer reaches over to take a precious ante—the forced amount that everyone at the table must pay each hand to see the cards—before depositing two cards that are then unceremoniously placed into the muck, or discard pile, seeing as there’s no one there to play them. With each round, the neat piles of chips grow slightly smaller. And still the chair remains empty. What kind of an idiot pays $10,000 to enter the most prestigious poker event in the world and then fails to show up to play? What kind of a dunce do you have to be to let yourself blind down (the term for letting your chips dwindle by not playing any hands) in the middle of the Main Event?

The genius, I regret to say, was your author. While everyone at the table idly speculated about my likely fate, I was huddled in fetal position on the bathroom floor of the Rio Hotel and Casino and, for lack of a more refined term, barfing my brains out. Could it have been food poisoning from the guacamole I knew I shouldn’t have eaten at the Mexican place just down the hallway during dinner break? A bad stress reaction? Delayed onset of stomach flu? Who knows. But my money was on migraine.

I had prepped endlessly. I had planned for all the contingencies—including, of course, migraine. I’m a lifelong sufferer, and I wasn’t about to leave anything to chance. I’d taken preventive Advil. I’d done yoga in the morning for relaxation. I’d meditated. I’d slept a full nine hours. I’d even eaten over dinner break, even though my nerves were telling me to avoid all sustenance. And still here it was.

That’s the thing about life: You can do what you do but in the end, some things remain stubbornly outside your control. You can’t calculate for dumb bad luck. As they say, man plans, God laughs. I could definitely detect a slight cackle.

My reasons for getting into poker in the first place were to better understand that line between skill and luck, to learn what I could control and what I couldn’t, and here was a strongly-worded lesson if ever there were: you can’t bluff chance. Poker didn’t care about my reasons for being on the floor. There was no one to whom I could direct a complaint, a plaintive “But it’s the Main Event!” The why didn’t matter. Nerves or stress, migraine or food poisoning, the cards would keep getting dealt. The message was clear. I could plan all I wanted, but the X factor could still always get me. The outcome would be what it would be. All I could do was my best with what I could control—and the rest, well, the rest wasn’t up to me.

As I contemplated the merits of dying right there versus first mustering the energy to bribe someone to bag up what measly chips I had left for me, before crawling off to die somewhere a bit less sticky and odiferous than this stall, I heard the telltale sound of my phone’s text message alert. It was my coach, Erik Seidel. “How’s it going?” the message read. Simple enough. He wanted to see how his student was faring in this, her biggest quest. The cackling from above was definitely growing stronger. I gathered my remaining willpower to text back.

“Fine. A little below average in chips.” Which was true as far as I knew. “Hanging in there.” Slightly less true, but hey, I’m ever the optimist.

“k, good luck” came the reply. Oh, Erik, you have no idea how much I need exactly that. A good infusion of old-fashioned luck.

Ante Up
New York, Late Summer 2016

“But for its costliness and dangers, no better education for life among men could be devised than the gambling table—especially the poker table.”

CLEMENS FRANCE, THE GAMBLING IMPULSE, 1902

From across the room, I see Erik Seidel’s signature baseball cap lying on the banquette by his side. I know it’s his signature because I’ve been studying him carefully from afar. I’ve charted his personality—or at least what seems like his personality—from the sidelines. He isn’t like most of the limelight-seeking top professionals, the players who love the camera, love the audience, love their shtick, whatever that shtick happens to be—temper tantrums, crazy aggression, incessant table chatter. He is quiet. Reserved. Determinedly attentive. He seems to play with deliberation and precision. And he is a winner: multiple World Series of Poker bracelets, the World Poker Tour title, tens of millions in winnings. I have chosen with care. I am, after all, about to ask him to spend the next year of his life with me—a marriage proposal, if you will, right off a first date. It was crucial I do my research well.

For the first time in a while, I’m nervous—really nervous. I chose my outfit with care—sophisticated but not stuffy, serious but not overly so. The kind of person you could trust and depend on, but who would also be fun to hang around with over drinks. It’s going to be a complicated seduction.

We’re meeting at a Hollywood version of what a French café should rightly look like. I’m early, but he’s even earlier. There he is, in the far right corner of the room, folded into a bistro table that seems too small for his lanky limbs and six-and‑a‑half-foot body. He’s wearing a dark T‑shirt that offsets a pale, intent face, and is reading a magazine. To my great relief, it looks like a New Yorker, the late August edition—the one with the muted watercolors of Sempé’s ocean landscape. A poker player who reads the New Yorker is my kind of poker player. Gingerly, a hound on the scent, afraid to scare off the prey in its sights, I approach the table.

ERIK SEIDEL IS SURELY the most self-effacing poker champion in the world. Apart from his poker accolades, he stands out from other players for his longevity: he still contends for number one, as he has since his career first started, in the late eighties. That takes some doing: the game has changed a lot in the last thirty years. As with so many facets of modern life, the qualitative elements of poker have been passed over in favor of the quantitative. Measurement presides over intuition. Statistics over observation. Game theory over “feel.” We’ve seen the trend play out in areas as far afield as psychology—social psychology giving way to neuroscience—and music, with algorithms and experts quantifying not just what we listen to but how, to the fraction of a second, a song should be structured for maximum pop. Poker is no different. Caltech PhDs line the tables. Printouts of stats columns are a common sight. A conversation rarely goes for more than a beat without the offhand dropping of GTO (game theory optimal) or +EV (positive expected value). Talk of frequencies trumps talk of feelings. But despite predictions that his style of play—a psychological one, based less on mathematical outputs and more on understanding the human element—would render him a dinosaur, Erik stays on top. In the bombastic, testosterone- and expletive-filled, ego-driven world of professional poker, Erik is atypical in more than his unassuming manner. He may be the only poker pro to boast a membership to the Brooklyn Academy of Music, a willingness to fly cross-country to see Dave Chappelle do stand‑up, or a near encyclopedic knowledge of the latest in the culinary scene from Los Angeles to Manila. He’s certainly the only pro who prefers New York to Vegas—and has a part-time residence on the Upper West Side of Manhattan, the same area where he grew up, and not just the usual Vegas abode. His curiosity is genuine and boundless, his enthusiasm for life entirely contagious.

“Do you know Julia and Angus Stone?” he asks offhand the first time we meet.

Who? I don’t even know which bucket those names fit into. Authors I’ve never heard of? Actors I’m woefully unaware of? Random New Yorkers Erik thinks I should know? Musicians, it turns out. I hope I am not losing his interest, that I’m sophisticated enough to pass his litmus test. My nervousness is going nowhere fast.

“They’re really something special. A brother-sister duo from Australia. I’ve heard them play many times.”

“Something special” is a phrase I’ll come to know well. Birbigs: something special. The new production of Othello: something special. An offbeat, tiny sushi bar tucked far from the strip in Vegas, where we go for dinner during my first trip out to the city of sin: something special. A professional poker player named LuckyChewy: something special. I’m his junior by a quarter century, but I realize talking to him that I’ve forgotten what it feels like to enjoy new experiences. I get lazy. I feel jaded. I want to curl up and stay in rather than see the latest talk at the 92Y or an obscure musical act from Canada playing at Joe’s Pub. (Erik drags me to both, and each time, he is right. Over the coming months, my playlist will be overhauled with his recommendations, much like my stand‑up predilections, Netflix queue, and list of theater shows that I “absolutely have to see” that I will of course never make it to. He’s a one-man Goings On About Town.) My ideal evening: dinner at home, some wine, some tea, a book or a movie in bed. His reply: You’re in New York City, the greatest city in the world! Look at what you’re missing.

He approaches poker with the same passion and constant inquisitiveness. He loves to follow the up‑and-coming players, is hip to the latest apps and programs, never assumes that he’s learned all there is. He refuses to plateau. If I had to assign him a life motto, it would be this: life is too short for complacency. Indeed, when I inevitably ask him the question he gets asked most frequently—what his single piece of advice would be to aspiring poker players—his answer is two words long: pay attention. Two simple words that we simply ignore more often than not. Presence is far more difficult than the path of least resistance.

I first encountered Erik the way I imagine most poker newbies do: in the 1998 movie Rounders. In many ways, Rounders brought poker to the masses—a story of a brilliant law student (Matt Damon) who pays his way through school with his poker prowess, in the end quitting law altogether to play full-time. And the one game that most inspires Damon’s character, playing in the background and analyzed ad infinitum throughout the film, is the 1988 WSOP final table showdown, between Erik Seidel and Johnny Chan. Johnny fuckin’ Chan, the master, the commentators repeat over and over. And Erik Seidel—the kid doesn’t know what hit him. The most famous poker match in the non-poker world. Seidel’s queens falling to Chan’s straight—an expert trap for an unwitting victim.

Chan was the reigning world champion. Seidel was at his first ever major tournament. He’d made it past 165 other contenders to be there, at the final table, the last man standing save one. It was an incredible feat, and the start of an incredible career.

The movie was a hit on college campuses. It came out in the late nineties, and by the early aughts, every kid was contemplating a life of paying their way through school by poker prowess. I didn’t care about poker at the time—I had no idea what a straight was, or why Chan had “trapped” Seidel with it, or any of it; it was a foreign language I had little interest in learning. But when I finally watched the film, some years later, a line uttered by Matt Damon as he contemplated Seidel and Chan’s matchup struck me: It wasn’t about playing the cards. It was about playing the man. A cliché, true—but one that got to the heart of my interests, that captured much of what I’d been thinking about the world. Psychology. Self-control. Being willing to check your straight all the way to the end, as Chan did—sitting on the best hand possible so stealthily that you rope along your opponents, tricking them into thinking they are winning when you’ve had them beat the whole time. You didn’t have to know what a straight was to see the appeal and the strategic beauty.

And here was the man himself: the kid turned master. One of the walking legends of the poker world. And I was here to persuade him to take me on as a student of poker for the next year of his life—even though, as far as I knew, he’d never taken a student in the past, and I had never even played a single game of poker. I wanted Erik to teach me—to train me for the ultimate poker championship, the World Series of Poker, or WSOP. The one that, so many years ago, had first made him an unwitting poker legend. Through that journey, I hoped to learn how to make the best decisions I possibly could, not just at the card table but in the world. Through poker, I wanted to tame luck—to learn to make a difference even when the deck seemed stacked against me.

IT WAS SUPPOSED TO be a year. Neat. Controllable. Digestible. I had a plan. I’d approach Erik, we’d team up, I’d play the Main Event at the World Series of Poker. And I’d live to tell the tale.

Coming up with a time limit was the easy part. A year is definable. It’s finite. It sells—because everyone can imagine doing something for a year. My year of this, my year of that, my year of trying on a new role that has a definite expiration date. No one wants to hear about my three and a half years of not-quite-making-it. Who has that kind of time? A year is manageable, pretty. A year is a neat antidote to the messiness of life.

But life had other ideas. A plan shifted. A framework disappeared and was replaced by something unforeseen. Man plans, God laughs, indeed. Whatever I may think about God, I believe in randomness. In the noise of the universe that chugs along caring nothing about us, our plans, our desires, our motivations, our actions. The noise that will be there regardless of what we choose or don’t choose to do. Variance. Chance. That thing we can’t control no matter how we may try. But can you really blame us for trying?

THE STRUGGLE FOR BALANCE on the spectrum of luck and control in the lives we lead, and the decisions we make, is one I have been grappling with for many years. As a child, I had perhaps the greatest luck of my life: my parents left the Soviet Union, opening to me a world of opportunity I would never otherwise have had. As a teen, I used every ounce of skill I had to excel academically and become part of the first generation in my family to make it to college in the United States. As an adult, I wanted to disentangle just how much of where I’d ended up had been my own doing as opposed to a twist of fate—like so many before me, I wanted to know how much of my life I could take credit for and how much was just stupid luck. In All Said and Done, Simone de Beauvoir says of her life that the “penetration of that particular ovum by that particular spermatozoon, with its implications of the meeting of my parents and before that of their birth and the births of all their forebears, had not one chance in hundreds of millions of coming about.” Such was the role that chance had played in the whole trajectory of her existence. “And it was chance, a chance quite unpredictable in the present state of science, that caused me to be born a woman. From that point on, it seems to me that a thousand different futures might have stemmed from every single movement of my past: I might have fallen ill and broken off my studies; I might not have met Sartre; anything at all might have happened.” How could you ever hope to separate the random from the intentional?

It was a philosophical query as much as anything else. And I tried to pursue it in the best way I knew how. I went to grad school. I posed the question. I developed some studies. How often are we actually in control, I wondered? And how does the perception of being in control in situations where luck is queen actually play out in our decision making? How do people respond when placed in uncertain situations, with incomplete information?

Over the course of five years, as part of my doctoral research at Columbia, I asked thousands of people to play a simulated stock market game, under time pressure. They would have to “invest” a certain amount of their money—real money; how they performed would translate directly into how much they were paid, and the range was vast, from one dollar to over seventy-five dollars—in one of two stocks, or in a bond, and do so over hundreds of trials. The bond always paid safely, and it always paid little—one dollar, to be exact. The stocks, however, mimicked the behavior of actual stocks in the market. They might earn you far more money—up to ten dollars a turn. But they could also be losers, wiping out ten dollars from your gains in the click of a mouse. In each round of the game, the two stocks (creatively titled “A” and “B”) were randomly assigned to be either “good” or “bad.” Choose the good stock, and you’d have a 50 percent chance of getting ten dollars, a quarter chance of making nothing, and a quarter chance of losing ten dollars. Choose the bad one, and your winning chances fell to 25 percent, while your losing chances jumped to 50. Here’s what I was interested in: What strategy would people follow in their choices—and how quickly would they learn which of the stocks was the winning one? (Optimal investment strategy would have you quickly gravitate to the good stock, as your overall earnings would be highest despite the intermittent losses.)

What I found was something completely unexpected. Over and over, people would overestimate the degree of control they had over events—smart people, people who excelled at many things, people who should have known better. Not only would they decide ahead of time how they were going to divide their investments, but they would decide based on incredibly limited information which stock was “good” and stick to their guns—even as they started losing money. The more they overestimated their own skill relative to luck, the less they learned from what the environment was trying to tell them, and the worse their decisions became: the participants grew increasingly less likely to switch to winning stocks, instead doubling down on losers or gravitating entirely toward bonds. Because they thought they knew more than they did, they ignored any signs to the contrary—especially when, as inevitably happens in real stock markets, winners became losers and vice versa. In other words, the illusion of control is what prevented real control over the game from emerging—and before long, the quality of people’s decisions deteriorated. They did what worked in the past, or what they had decided would work—and failed to grasp that the circumstances had shifted so that a previously successful strategy was no longer so. People failed to see what the world was telling them when that message wasn’t one they wanted to hear. They liked being the rulers of their environment. When the environment knew more than they did—well, that was no good at all. Here was the cruel truth: we humans too often think ourselves in firm control when we are really playing by the rules of chance.

The problem stayed with me. But what was its solution? How could you use that theoretical knowledge to make better choices, practically speaking?

It’s a tough ask, for one main reason: the equation of luck and skill is, at its heart, probabilistic. And a basic shortcoming of our neural wiring is that we can’t quite grasp probabilities. Statistics are completely counterintuitive: our brains are simply not cut out, evolutionarily, to understand that inherent uncertainty. There were no numbers or calculations in our early environment—just personal experience and anecdote. We didn’t learn to deal with information presented in an abstract fashion, such as tigers are incredibly rare in this part of the country, and you have a 2 percent chance of encountering one, and an even lower chance of being attacked; we learned instead to deal with brute emotions such as last night there was a tiger here and it looked pretty damn scary.

Millennia later, the shortcoming persists. It’s called the description-experience gap. In study after study, people fail to internalize numeric rules, making decisions based on things like “gut feeling” and “intuition” and “what feels right” rather than based on the data they are shown. We need to train ourselves to see the world in a probabilistic light—and even then, we often ignore the numbers in favor of our own experience. We believe what we want to see, not what research shows. Take something that’s on plenty of minds in recent times: disaster preparedness. What do you do to prepare for the extreme weather events—hurricanes, floods, earthquakes—that are increasing in frequency as the earth warms? What about nuclear war or a terrorist attack—do you need to worry about that? There are statistics to help you reach an answer, like whether you need special insurance for your home or if you should even be buying property in certain areas—just like there are probability charts that inform you of the risk of your being the victim of terrorism as opposed to, say, slipping in your shower and suffering a fatal or debilitating fall. But here’s what psychologists find, over and over: you can show people all the charts you want, but that won’t change their perceptions of the risks or their resulting decisions. What will change their minds? Going through an event themselves, or knowing someone who has. If you were in New York City during Hurricane Sandy, for instance, you are far more likely to purchase flood insurance. If you weren’t, you may invest in a beachfront property in Malibu even though the numbers say your beach will be gone soon, and your house along with it. If you lived through 9/11, your fear of terrorism will be vastly overblown. In all cases, the reaction isn’t in line with the statistics. Not every house in New York needs flood insurance—you’ve overcompensated because you went through a bad experience. Beachfront properties are an awful long-term investment—you’ve undercompensated because the statistics haven’t ever affected you personally. Your likelihood of slipping in a shower is orders of magnitude larger than your likelihood of being in a terrorist attack—but just try convincing someone of that, especially if they knew someone who died in the Twin Towers.

Our experiences trump everything else, but mostly, those experiences are incredibly skewed: they teach us, but they don’t teach us well. It’s why disentangling chance from skill is so difficult in everyday decisions: it’s a statistical undertaking, and one we are not normally equipped to deal with. Which brings me to poker: Used in the right way, experience can be a powerful ally in helping to understand probabilistic scenarios. The experience just can’t be a one-off, haphazard event. It has to be a systematic learning process—much like the environment you encounter at the table. And the correct systematic learning process can help you unravel chance from everything else in a way that no amount of cramming numbers or studying theory ever will.

Several years after I left academia, the problem of skill versus chance became more personally pressing. 2015 was not a good year for the Konnikova clan. The first week of January, my mother—my role model in most every way—lost her job of almost twenty years, summarily downsized in a private equity acquisition. Her coworkers cried. Her boss cried. They petitioned to hire her back. She was good at what she did: computer programming. I thought she’d be back on her feet in no time. Instead, she hit upon a harsh reality of Silicon Valley: ageism is alive and thriving, especially for women. She’s in her fifties—too old for the young set, not old enough to retire. A year later, she was still jobless. Life is so unfair was my first thought—but if there’s anything Mom taught me, it’s that life has no concept of fairness. It’s just tough luck. Deal with it.

A few months later, my vivacious, healthy, living‑on‑her-own grandmother slipped in the night. The edge of a metal bed frame. Hard linoleum floor. No extra pair of ears to hear anything amiss. The neighbors found her in the morning, alerted by a light that shouldn’t have been turned on. Two days later, she was dead. We never said goodbye. I don’t even remember our last conversation—it was that banal, the same phrases, the same intonations, no, nothing new to report on either end. She probably asked when the first copies of my new book would be ready. She wouldn’t be able to read it—she’d have to wait for the Russian translation—but she couldn’t wait to hold it. It’s a safe bet that question came up. She asked me that every time we spoke. And every time, I’d berate her: stop asking; I’ll let you know when. I’d grow frustrated. She’d raise her voice and inform me that she was never going to ask me anything about anything ever again. I should have been kinder. But hindsight always sees most clearly. To the end, she signed off her voicemails to me with a short phrase: “This is Grandma.” As if there could be some confusion. And to the end, I never called back quite quickly enough. She’d been through World War II, survived Stalin, Khrushchev, Gorbachev, and was defeated by a slippery floor and one misplaced foot. Unfair. Or rather, unlucky. One surer step and she’d still be here.

My husband lost his job next. The startup he’d joined failed to start up as planned, and with that, I momentarily found myself in a position I hadn’t been in for years: supporting my family on a freelance writer’s income. We left our beautiful West Village apartment. We changed our habits. We did our best to adjust. And on top of it all, I found my health suddenly failing. I’d recently been diagnosed with a bizarre autoimmune condition. No one knew quite what it was, but my hormone levels had declared insanity, and I was suddenly allergic to just about everything. Sometimes, I couldn’t even leave the apartment: my skin broke out in hives whenever anything touched it, and it was winter outside. I sat huddled with my laptop, draped in an old, loose T‑shirt, hoping for the best. I went from expert to expert, steroid regime to steroid regime, only to be told the same thing: idiopathic. Doctor speak for “We don’t have a clue.” That idiopathy (root word: idiocy) was expensive. Unfair. Bum luck. But was it? Maybe it had been my fault for failing to listen to my mother and sneaking out to play on the balcony so many years ago. I was born in Russia, after all, and was there for Chernobyl; her admonition to stay inside had its reasons. Maybe my two-year-old self was to blame. I sat reading James Salter—“We cannot imagine these diseases, they are called idiopathic, spontaneous in origin, but we know instinctively there must be something more, some invisible weakness they are exploiting. It is impossible to think they fall at random, it is unbearable to think it”—and I found myself nodding in recognition. Whether it was pure chance or not, it sucked.

It’s a familiar pattern of thought. Luck surrounds us, everywhere—from something as mundane as walking to work and getting there safely to the other extreme, like surviving a war or a terrorist attack when others mere inches away weren’t as fortunate. But we only notice it when things don’t go our way. We don’t often question the role of chance in the moments it protects us from others and ourselves. When chance is on our side, we disregard it: it is invisible. But when it breaks against us, we wake to its power. We begin to reason about its whys and hows.

Some of us find comfort in pure numbers. We call it what it is: pure, high-school-math chance. As Sir Ronald Aylmer Fisher, a twentieth-century statistician and geneticist, pointed out in 1966, “The ‘one chance in a million’ will undoubtedly occur with no less and no more than its appropriate frequency, however surprised we may be that it should occur to us.” Consider the 7.5 billion people who currently make up the world’s population and you can be sure that the highly improbable is happening with regular frequency. The “one chance in a million” takes place every second. Someone close to you will die in a freak accident. Someone will lose a job. Someone will fall ill with a mysterious disease. Someone will win the lottery. It is probability, it is pure statistics, and it is part of life, neither good nor bad. If bizarre coincidences and one-off events didn’t happen—well, that would be the truly remarkable thing.

Some of us imbue probability with emotion. It becomes luck: chance that has suddenly acquired a valence, positive or negative, fortuitous or unfortunate. Good or bad luck. A lucky or unlucky break. Some of us invest luck with meaning, direction, and intent. It becomes fate, karma, kismet—chance with an agenda. It was meant to be. Some even go a step further: predestination. It was always meant to be, and any sense of control or free will we may think we have is pure illusion.

So how exactly does poker fit into all this? Until I began this journey, I’d never been a card player. I’d never played poker in my life. I’d never even seen a real game. Poker was a nonentity in my mind. But faced with event after event breaking the wrong way, I did what I always do when I try to understand something. I read. Anything that could help shed light on what was happening, that would allow me to regain some semblance of control. And in my reading frenzy, I came across John von Neumann’s Theory of Games and Economic Behavior.

Von Neumann was one of the greatest mathematical and strategic minds of the twentieth century: he invented that little machine we all carry around with us, the computer (back then, it wasn’t so little), crafted the technology behind the hydrogen bomb, and is the father of game theory. Theory of Games is his foundational text, and here’s what I learned within its pages: the entire theory was inspired by a single game—poker. “Real life consists of bluffing, of little tactics of deception, of asking yourself what is the other man going to think I mean to do,” von Neumann wrote. “And that is what games are about in my theory.”

Von Neumann did not care for most card games. They were, he thought, as boring as the people who wasted their lives playing them, trying to coax mastery—impossibly—out of pure chance. Games of pure chance, though, were to his mind not much worse than those at the opposite end: games like chess, where all the information could theoretically be gleaned, where every move could be mathematically accounted for in advance. There was one exception to his distrust of gaming: poker. He loved it. To him, it represented that ineffable balance between skill and chance that governs life—enough skill to make playing worthwhile, enough chance that the challenge was there for the taking. He was a god-awful player by every account, but that never stopped him. Poker was the ultimate puzzle: he wanted to understand it, to unravel it—to, in the end, beat it. If he could figure out how to disentangle the chance from the skill, how to maximize the role of the latter and learn to minimize the malice of the former, he believed he would hold the solution to some of life’s greatest decision challenges.

For poker, unlike quite any other game, mirrors life. It isn’t the roulette wheel of pure chance, nor is it the chess of mathematical elegance and perfect information. Like the world we inhabit, it consists of an inextricable joining of the two. Poker stands at the fulcrum that balances two oppositional forces in our lives—chance and control. Anyone can get lucky—or unlucky—at a single hand, a single game, a single tournament. One turn and you’re on top of the world—another, you are cast out, no matter your skill, training, preparation, aptitude. In the end, though, luck is a short-term friend or foe. Skill shines through over the longer time horizon.

Poker has a mathematical foundation, but with a dose of human intention, interaction, psychology—nuance, deception, little tricks that don’t quite reflect reality but help you gain an edge over others. Humans aren’t rational. Information isn’t open to all. There are no “rules” of behavior, only norms and suggestions—and within certain broad constraints, anyone might break those norms at any point. The games that interested von Neumann are the ones that, like life, can’t ever be mapped cleanly. Real life is based on making the best decisions you can from information that can never be complete: you never know someone else’s mind, just like you can never know any poker hand but your own. Real life is not just about modeling the mathematically optimal decisions. It’s about discerning the hidden, the uniquely human. It’s about realizing that no amount of formal modeling will ever be able to capture the vagaries and surprises of human nature.

When I read von Neumann’s rationale for choosing poker above all else to explore the most important strategic decisions in the world—he was advising the US military, after all—something clicked. Poker wasn’t theoretical, the way the research I’d done and the studies I’d run had been. Poker was practical. Poker was experiential. Poker embodied the way the human mind learns best, and it wasn’t a one-off event: it was a systematic process. It was, in other words, perfect for what I had in mind.

Poker isn’t a homogeneous game; there are multiple varieties of play, with names like Stud, Omaha, Razz, Badugi, and HORSE. Each has its own unique set of rules, but in any style of poker, the basic parameters are essentially the same: Some cards are dealt faceup, visible to all—these are the community cards—and some facedown, so that only the person to whom they are dealt can see them. You make bets based on how strong your hand is and how strong you think others’ hands are. Because the only other cards you know for sure are your own, you are in a game of incomplete information: you must make the best decision you can, given the little you know. The last player left standing at the end of the final round of betting takes the pot, or the sum of money that has been bet up to now.

But the style I’ve chosen to pursue is one particular variant of the game, which happens to be the most popular. No Limit Texas Hold’em. How no limit hold’em differs from other forms of poker is twofold. The first is in the precise amount of information that is held in common versus in private. Each player is dealt two cards facedown: the hole cards. This is privileged information. I can try to guess what you have based on how you act, but I can’t know for sure. The only information I’ll have is your betting patterns once the public information—the cards dealt to the middle of the table, faceup—is known. In hold’em, there are three stages of dealing the middle cards: the first three cards, called the “flop,” are dealt at the same time; the fourth card, the “turn,” is dealt after another round of betting; and the fifth, the “river,” is dealt after yet another round. In total, then, you have two cards in your hand, known only to you, five cards in the middle, known to everyone, and four “streets,” or betting rounds, in which to make your best guess as to how the cards you can’t see stack up against your own.

Where some forms of poker assume too many unknown variables (one form gives each player five cards facedown, for instance), making skill less of a factor, and others leave too little unknown (one hole card), reducing the guesswork too greatly, the amount of incomplete information in Texas hold’em creates a particularly useful balance between skill and chance. Two hole cards is just about as practical a ratio as you can have: enough unknown to make the game a good simulation of life, but not so much that it becomes a total crapshoot.

The second thing that distinguishes this particular playing style is the concept of no limit—von Neumann’s own preferred style. “The power of the pure bluff is restricted in a game of limit,” explains Amarillo Slim, one of the best poker players of his day, who, in 1972, won the third ever WSOP title. When there’s a limit, it means that the exact amount you bet has a ceiling on it. Sometimes, the ceiling is set by the house rules—an arbitrary number above which you can’t go. Sometimes, in what’s known as “pot limit,” it’s set by the total amount in play: your bet cannot exceed what’s in the pot. Either way, your range of action is artificially restricted. In no limit, you can bet everything you have, at any point. You can “shove” or “jam”—that is, make an all‑in bet, placing every chip you have into the pot. And that’s when the game gets really interesting. Limit is for people who have “the guts of an earthworm or make [their] living as an accountant,” Slim says. “If you can’t ‘move in’ on someone—meaning bet everything you’ve got in front of you—then it’s not real poker.”

And that’s what makes this game a particularly strong metaphor for our daily decision making. Because in life, there is never a limit: there’s no external restriction to betting everything you have on any given decision. What’s to stop you from risking all your money, your reputation, your heart, even your life at any point you choose? Nothing. There are no rules, at the end of the day, save some internal calculus that only you are privy to. And everyone around you has to know that when they make their decisions: knowing you can go all the way, how much should they themselves invest? It’s the endless game of brinkmanship, popularized by another giant of game theory, the Nobel-winning economist Thomas Schelling, that plays out everywhere in our lives. Who will say “I love you” first, moving “all in” in the relationship—and if you say it, will you be left out, so to speak? Who will walk away from the business negotiation? Who will wage war? The ability to go all in—and the knowledge that going all in is an option for everyone around us—is the crucial variable that makes so many decisions so very difficult.

And, of course, there’s the emotional element. Be it at the poker table or out in the real world, there is no risk quite like the risk of the shove: at its best, it can let you “double through”—that is, win the maximum amount possible, doubling your stack—but it can also end your game. You can emerge with the deal of a lifetime, or a life partner—or you can find yourself bankrupt or emotionally devastated. Like life, no limit poker is high risk and high reward. It’s no coincidence that the WSOP champion is determined by No Limit Texas Hold’em. And it’s no coincidence that that is the style of play I have chosen to learn. If you’re trying to make the best decisions, you might as well go with the best proxy.

Once you’ve chosen your game, there’s one more choice to make: cash or tournament? In a cash game, every chip has a cash value. You buy in to a game for a certain amount, say, $100, and you get that exact amount in chips placed in front of you. At any point, you can choose to add more money to your stack by paying the requisite amount in cash. At any point, you can get up and walk away. And if you ever go bust, you can always choose to rebuy and start over for another shot. What’s more, the structure will remain constant. If you bought in to a $1/$2 game—a game where the blinds, or forced bets that you have to post into the pot before seeing your cards, are one dollar for the small blind and two dollars for the big blind—it will always be a $1/$2 game. You won’t turn around and find you’re suddenly forced to pay five dollars when it’s your turn in the big blind.

In a tournament, chips have value only relative to other players’: they are a way of keeping score. A $100 buy‑in might get you ten thousand chips or two hundred; it doesn’t really matter. Everyone gets the same amount, and your goal is to accumulate as many of them as possible, with the eventual winner holding all the chips. If you start losing, that’s too bad; there’s no option to call someone over and pay another $100 for another stack of chips. And once you bust, you’re out of there. You’re playing for your tournament life. As for the blinds, those go up on a predetermined schedule. So, while you might start at 1/2, you will find that in a half hour or forty-five minutes or whatever the structure says, they rise to 2/4, 4/8, and so on. Suddenly, your chips aren’t worth as much as they were and the pressure is on to start winning more pots. Otherwise, in short order you’ll blind out—that is, spend all your chips paying the forced bets, or blinds—and find yourself with nothing.

Those two setups create rather different dynamics. Cash games are War and Peace. You’re a thousand pages in and still no closer to finding out how the battle resolved itself. You can try to flip ahead, but events will unfold at whatever pace they choose. Tournaments are far more Shakespearean in nature. You’ve barely hit act three and half the cast is already dead. If you want an overview of life at warp speed, tournament poker is the way to go. That’s what I choose.

After spending the several months following my von Neumann revelation poring over books on poker, watching videos of the best pros playing and listening to the commentary, I began to genuinely wonder if, in poker, I could finally find a way to overcome my all-too-human inability to disentangle chance from skill in the morass of daily life, and instead learn to master it. Could poker help my husband figure out his next career move, and when it was right to just start playing again as opposed to waiting for the perfect cards? Could it help me think through when to give up with the medical consultations, or how to deal with the fallout of the bills in planning our financial future? Could it help my mother leverage an unfavorable table environment, so to speak, in her favor? Could it help me plan my own career moves in a way that would maximize my wins and minimize the losses? I decided to try my hand at finding out.

WHICH BRINGS US BACK to my meeting with Erik Seidel, for whom the challenge of poker is slightly different. For over three decades, he has led the poker world. He holds eight WSOP bracelets (only five players in the tournament’s history have more) and a World Poker Tour title. He is in the Poker Hall of Fame, one of just thirty-two living members. He boasts the fourth-highest tournament career winnings in the entire history of the game (for many years he was number one), and is fourth in the number of times he cashed in the WSOP (114). Over the years, he has spent fifteen weeks ranked first in the Global Poker Index, and many consider him the GOAT—the greatest of all time.

Why on earth would a professional poker player—the professional poker player—agree to let a random journalist follow him around like an overeager toddler, asking the most basic questions about how the world works? He doesn’t care for fame, so I can’t play the journalism card all that well. He doesn’t like to share his tactics. He’s notoriously reticent.

“I wouldn’t actually be in the book, would I?” Erik asks back at the West Village bistro as I lay out my proposal. He shifts around on the bench and hunches over a little more, as if deflecting attention from his presence as much as he possibly can.

“Well …” This isn’t going quite as anticipated.

“I don’t know if I can take anything on. You know I’ve never coached anyone. And my travel schedule …”

I cut him off. This is going nowhere fast. “I may not know how many cards are in a deck—”

“Wait, you’re serious?” He cuts me off. His eyebrows have shot up. At least I’ve managed to surprise him.

“Absolutely. I’m not going to be the typical student.”

What I do have, I continue, is my background.

“I have a PhD in psychology. I studied decision making—the sort of stuff you do every day, but from a theoretical perspective.”

“A psychologist. Now that’s interesting. That could be really helpful in poker.” He leans over the table, lanky elbows framing his egg-white omelet. “I think you’re approaching it from the area of most value, especially of most differentiated value. All the other guys are very math-based, very data-based. This area is way more open. Actually, of the great players, the ones who are some of the most exploitable are the ones who are really into math.”

“Oh, good.” I’m happy to have struck a chord after the false start. “I haven’t done any math since high school,” I admit.

“My math skills are not particularly great, either, and that’s not unusual,” Erik says, putting me at ease. “It doesn’t hurt, but it’s no barrier to playing well. The basic math is so basic that a six-year-old could do it.”

I’m relieved. But I should probably omit the part where I tell him that I usually count on my fingers.

“It’s all about thinking well. The real question is, can good thinking and hard work get you there? And I think it can,” Erik says. In a way it’s good, he goes on, that I’m an outsider. I can bring fresh eyes, perspective—and some of the skills players don’t typically have. I might not have the narrow expertise of knowing what a “range” is or why I’d want one that’s polarized or merged, but I do have the broad expertise of knowing how to learn, how to think, how people work. In Range, David Epstein reflects on the nature of the outsider: “Switchers are winners,” he writes. Perhaps, as a switcher, I’ll be able to get beyond the myopia that often comes with an insider’s perspective, bring what psychologist Jonathan Baron calls “active open-mindedness.” Not all experience is created equal, of course, but mine might be particularly well suited here.

Erik is especially intrigued by my language ability.

“You can speak how many languages?” he asks.

“Well, only two completely fluently, English and Russian. But I’ve been fluent in French and Spanish in the past, and pretty good in Italian,” I continue. “I used to take Persian, but I’ve really forgotten all of it.”

“I think that’s going to be really helpful,” Erik says. “Do you know Phil Ivey?”

I nod. He’s one of the only poker names that is on my radar.

“There was an argument for him being the best at all of these different poker games at one point,” he explains. I can think of each game like a different language that needs to be mastered. “And what’s extra fascinating about that to me is that his sister is a linguist. And she speaks fifteen languages or something.”

I’m impressed. My abilities look meager in comparison.

“How many people do you get that have that kind of a brain or interests?” Erik continues. “It seems as if Phil and his sister have a very similar brain that functions in a way that they pick up languages in some incredible way. It’s nice to hear that you do have obviously some abilities to pick up languages quickly or to adapt to different languages, because that’s essentially what the challenge is.”

It makes a certain amount of sense. In many ways, poker does resemble language learning. After all, there is a new grammar, a new vocabulary, a new way of relating to the world. But there is one big difference that I can see. Humans have built‑in language-learning ability. Some are better at it than others, true, but we all learn our native language fairly effortlessly—the brain seems to come equipped with a road map for discerning meaning out of sounds and figuring out rules without ever being taught them explicitly. Not so poker: no matter how psychologically you want to play, much of the game is about statistics. You need to understand odds, how good your hand is, how good it is relative to others’, how likely it is to improve, and so on. Each of these requires a certain amount of statistical calculation. How well I’ll fare there is another story.

“You know, psychology really is the most fascinating part of the game,” Erik says, interrupting my thought process. “What specifically about decision making did you study? Like Kahneman?”

“Actually, my graduate adviser was Walter Mischel—you know, the marshmallow guy?”

“Oh wow. That’s exciting. Self-control is huge in the game.”

So Mr. Seidel knows the marshmallow guy, too. I seem to have picked well.

“I figured it might be,” I reply. “I mean, I’ve obviously never played. But here’s what I can tell you: I’m willing to bet I’ve read more about all of this than anyone else at the poker table. I’ve done studies on stress and decision making. Emotional stuff. Time pressure stuff. All sorts of things that I think are going to be super relevant. And—and …” I’m on a roll and don’t want him to interrupt. I need him to agree to take me on. “Look at this paper I found.” I fish out my ace in the hole—a paper I’ve tracked down on poker tells that, as far as I know, never made it out of academia. And it’s based on a WSOP final table analysis. The real deal.

Erik reads carefully. He’s all concentration. And then he starts laughing.

“Wow. OK. Just don’t show this to anyone else.”

I promise him I won’t. And with that, a partnership is born.

I HAVE A RARE opportunity here: hardly ever do we have a chance to learn an entirely new skill, to immerse ourselves in novicedom, not only with the guidance of the best expert in the world but in an area, where the skill-chance continuum is so balanced, so redolent of life, as poker. Erik Seidel doesn’t actually care about whether I win any given game. He just wants to see how far we can go—how far psychology, people reading, and emotional nuance can get me. If you are starting from scratch, can a deep understanding of the human mind win out over the mathematics and statistical wunderkinds of the poker table? In a way, it’s as much a test of life philosophy as anything else. The qualitative side of things versus the measurable. The human versus the algorithmic. I will be on one extreme of a dynamic that is at the center of a paradigm shift in this country. And the ultimate test will be the World Series Main Event. The tournament has never in its history had a female champion—and only one woman has ever made the final table. Erik isn’t just training me to play. He’s training me to win: that’s how much he believes that this way of doing things can ultimately succeed. And I will do everything I can to make the journey count.

For me, this isn’t just a test of a philosophy—though that is central. It’s also personal. I don’t want to let Erik down. His faith is, in part, confidence in my ability and his approach, but is also an expression of boundless generosity: to his friends and the people he trusts or respects, Erik is the most giving person I have encountered in a long time. He isn’t just giving me his time. He is giving me his trust, his energy, his mind, his reputation. All I can think is, I better not fuck this up.

IT WAS SUPPOSED TO be a year. It became a new life. From novice, I turned champion. From amateur, I went pro. And all along the way, I watched with a mix of wonder and pride as my life changed for the better. This book is the result of that journey. It is not an exhaustive exploration of the game, how to play it, how to win at it, how to excel. It is no guide. That has been covered by experts far greater than I. It is a picking up of von Neumann’s challenge: poker as a lens into the most difficult and important life decisions we have to make, an exploration of chance and skill in life—and an attempt to learn to navigate it and optimize it to the best of our potential.

What I will offer throughout is insight into decision making far removed from poker, a translation of what I’m learning in the casino to the decisions I make on a daily basis—and the crucial decisions that I make only rarely, but that carry particular import. From managing emotion, to reading other people, to cutting your losses and maximizing your gains, to psyching yourself up into the best version of yourself so that you can not only catch the bluffs of others but bluff successfully yourself, poker is endlessly applicable and revelatory. The mixture of chance and skill at the table is a mirror to that same mixture in our daily lives—and a way of learning to play within those parameters in superior fashion. Poker teaches you how and when you can take true control—and how you can deal with the elements of pure luck—in a way no other environment I’ve encountered has quite been able to do. What’s more, in an age of omnipresent distraction, poker reminds us just how critical close observation and presence are to achievement and success. How important it is to immerse yourself and to learn new things, truly. As Erik told me that first day, lesson one: pay attention. This book isn’t about how to play poker. It’s about how to play the world.

The Birth of a Gambler
Boston, Fall 2016

“If we consider games of chance immoral, then every pursuit of human industry is immoral; for there is not a single one that is not subject to chance, not one wherein you do not risk a loss for the chance of some gain.”

THOMAS JEFFERSON, “THOUGHTS ON LOTTERIES,” 1826

You are going to be a gambler?”

That’s my grandmother Baba Anya speaking. My other grandmother, my last living grandparent. I’ve come to Boston for a family visit, nearly bouncing with excitement at my new project, and she is not impressed. To call her lukewarm would be the understatement of the hour. She has a way of setting her jaw that makes it jut out like it’s about to slice through stone. The chiseled expression of a conquering hero atop a pedestaled horse. A conquering hero—or an angry general. I can feel the full brunt of grandmotherly disappointment gather on my shoulders. She’s almost (though not quite) come to forgive me for not wanting kids after over a decade of my persistent explanations, but this—this is a new low. If you think you know the kind of disappointment a five-foot-some-odd ninety-two-year-old is capable of, think again. She was a Soviet-era schoolteacher. She’s had more practice than an army drill sergeant.

She shakes her head.

“Masha,” she says—my Russian nickname. “Masha.” The word is laden with so much sadness, so much regret for the life I’m about to throw away. In a single word, she has managed to convey that I’m on the brink of ruin, about to make a decision so momentously bad that it is beyond comprehension.

I can see the visions of Dostoyevsky’s gambler dancing through Baba Anya’s head, throwing away his life in the fictional Roulettenburg. Dostoyevsky knew of what he wrote. On a trip to Baden-Baden with his twenty-two-year-old lover, Polina Suslova, he developed a passion for roulette and “lost absolutely everything.” That didn’t stop him from wanting more: even though the game would eventually lead to the end of his affair, the near-end of his second marriage, and financial ruin, the tables held an irresistible draw. “I go to the bottom line in everything,” he wrote in one of his letters, “and throughout my entire life, I have crossed this bottom line.”

This is the fate I can clearly see written all over my grandmother’s face. A Harvard education and this, this, is what I’m choosing to do?

“Masha,” she repeats. “You are going to be a gambler?”

My grandmother’s reaction may be extreme—nothing is quite as personal as your grandchildren heading out to ruin on your watch; you have to throw your body in the breach—but it is far from atypical. In the coming months, I’ll be accused of being responsible for a society-wide “sin slide” for advocating for poker as a teaching tool. I’ll be called a moral degenerate by strangers. A group of highly intelligent people at a retreat will tell me playing poker is all well and good, but how do I feel about encouraging people—children even!—to lie?

The world of poker is laden with misconceptions. And first among them is the very one I’m seeing from a stricken Baba Anya: equating poker with gambling. I’d been ready to go, gearing up to get started. To my mind, the journey was well motivated as it was: of course people would understand that poker was an important way to learn about decision making. I mean, think of von Neumann! Let’s get to the tables! But looking at Baba Anya, I realize that the battle for support—and the justification for poker as not just a learning tool, but as one of the best tools there is for making decisions that have nothing to do with the game itself—is going to take a bit more fighting. I’m going to be explaining this over and over, so I may as well get it right.

POKER, TO THE UNTRAINED eye, is easy. Just like everyone who meets me seems to have “a book in them,” which they’ll write just as soon as they get a chance—everyone can use words, after all—so everyone who meets Erik thinks they are just a hop away from becoming a poker pro or, at the very least, a badass poker bro. Most of us underestimate the skill involved. It just seems so simple: get good cards and rake in the dough. Or bluff everyone blind and rake in the dough once more. Either way, you’re raking it in. It seems like every time I talk to Erik he has a new story of a bartender or server or Uber driver who recognizes him and offers up the wisdom that he could play just as well; he’s just never gotten the chance to do so. That “lucky break” simply hasn’t manifested itself. But maybe if Erik just stakes him for that big game …

And poker does have an element of chance, to be sure—but what doesn’t? Are poker professionals “gamblers” any more than the man signing away his life on a professional football contract, who may or may not be injured the next week, or find himself summarily dropped from the team in a year because he failed to live up to his promise? We judge the poker player for gambling; we respect the stockbroker for doing the same thing with far less information. In some ways, poker players gamble less than most. After all, even if they lose an arm, they can still play.

But the misperception is ingrained in the popular mind for one simple reason. Unlike, say, Go or chess, poker involves betting. And betting involves money. And as soon as that enters the picture, you might as well be playing craps or baccarat—games that truly are gambling. And so I tell my grandmother the words that I’ve come to repeat so often they are like my own private mantra: in poker, you can win with the worst hand and you can lose with the best hand. In every other game in a casino—and in games of perfect information like chess and Go—you simply must have the best of it to win. No other way is possible. And that, in a nutshell, is why poker is a skilled endeavor rather than a gambling one.

Imagine two players at a table. The cards are dealt. Each player must look at her cards and decide whether or not the cards on their own are good enough to bet. If she wishes to play, she must at minimum “call” the big blind—that is, place as much into the pot as the highest bet that already exists. She may also choose to fold (throw out her cards and sit this hand out) or raise (bet more than the big blind). But who knows what factors she’s using to make her decision? Maybe she has a premium hand. Maybe she has a mediocre hand but thinks she can outplay her opponent and so chooses to engage anyway. Maybe she has observed that the other player views her as conservative because she doesn’t play many hands, and she’s taking advantage of that image by opening up with worse cards than normal. Or maybe she’s just bored out of her mind. Her reasoning, like her cards, is known only to her.

The other player observes the action and reacts accordingly: if she bets big, she may have a great hand—or be bluffing with a bad one. If she simply calls, is it because her hand is mediocre, or because she’s a generally passive player, or because she wants to do what’s known as “slow playing”—masking an excellent hand by playing it in a restrained fashion, as Johnny Chan did in that 1988 WSOP matchup with Erik Seidel? Each decision throws off signals, and the good player must learn to read them. It’s a constant back-and-forth interpretive dance: How do I react to you? How do you react to me? More often than not, it’s not the best hand that wins. It’s the best player. This nuance, this back-and-forth: this is why von Neumann saw the answer to military strategy in the cards. Not because everyone is a gambler, but because to be a winning player, you have to have superior skill, in a very human sense.

Indeed, when the economist Ingo Fiedler analyzed hundreds of thousands of hands played on several online poker sites over a six-month period, he found that the actual best hand won, on average, only 12 percent of the time and that less than a third of hands went to showdown (meaning that players were skillful enough to persuade others to let go of their cards prior to the end of the hand). In mid-stakes games, with blinds of 1/2 and 5/10, there were some players who were consistent winners, and as stakes went to nosebleed—50/100 and up—the variability in skill went down significantly. That is, the higher the amount of money for which people played, the greater their actual skill edge. When Chicago economists Steven Levitt and Thomas Miles looked at live play and compared the ROI, or return on investment, for two groups of players at the 2010 WSOP, they found that recreational players lost, on average, over 15 percent of their buy-ins (roughly $400), while professionals won over 30 percent (roughly $1,200). They write, “The observed differences in ROIs are highly statistically significant and far larger in magnitude than those observed in financial markets where fees charged by the money managers viewed as being most talented can run as high as three percent of assets under management and thirty percent of annual returns.” Success in poker, in other words, implies far more skill than success in that far more respectable profession, investing.

Of course, the rationale goes much deeper. Betting—that bête noire that seems to be such a stumbling block for even rational minds when you try to explain the skilled nature of poker—is actually at the heart of what makes it superior to almost any other game of skill: betting on uncertainty is one of the best ways of understanding it. And it is one of the best ways of conquering the pitfalls of our decision processes in just about any endeavor. It doesn’t take a gambler to understand why. In his Critique of Pure Reason, the German philosopher Immanuel Kant proposes betting as an antidote to one of the great ills of society: false confidence bred from an ignorance of the probabilistic nature of the world, from a desire to see black and white where we should rightly see gray. From a misplaced faith in certainty, the fact that to our minds, 99 percent, even 90 percent, basically means 100 percent—even though it doesn’t, not really. Kant offers the example of a doctor asked to make a diagnosis. The doctor reaches a verdict on the patient’s malady to the best of his knowledge—but that conclusion isn’t necessarily correct. It’s just the best he can do given the information he has and his experience in this particular area. But will he tell the patient he’s unsure? Maybe. But more likely, if his certainty reaches a specific threshold—a different one for different doctors, to be sure—he will just state his diagnosis as fact.

But what if he had to bet on it? “It frequently happens that a man delivers his opinions with such boldness and assurance that he appears to be under no apprehension as to the possibility of his being in error,” Kant writes. “The offer of a bet startles him, and makes him pause.” Now that he has something real at stake, he has to reevaluate just how sure of a sure thing his opinion really is. “Sometimes it turns out that his persuasion may be valued at a ducat, but not at ten,” Kant continues. “If it is proposed to stake ten, he immediately becomes aware of the possibility of his being mistaken.”

And what if the bet is even higher? Suddenly, we have a corrective for many of the follies of human reason. “If we imagine to ourselves that we have to stake the happiness of our whole life on the truth of any proposition, our judgment drops its air of triumph, we take the alarm, and discover the actual strength of our belief,” says Kant. Would you bet your entire net worth on an opinion that you’ve just spent hours confidently offering on social media, broaching no possibility of being mistaken? Would you bet your marriage? Your health? Even our deep convictions suddenly seem a lot less certain when put in that light.

Of course, it’s a long way between betting on your own opinions and judging someone else. When we err, we are much more tolerant than when we think someone else has gone astray. Think of the 2016 presidential election. Every media source had polls showing Hillary Clinton winning—and every media source was wrong. No one was on the receiving end of the subsequent ire more than Nate Silver. He had done such an accurate job forecasting past elections that he was practically pilloried for being so “wrong” this time around. But what exactly did Silver say? In his final poll, on November 8, 2016, he gave Clinton a 71 percent chance of winning—and Trump a 29 percent chance. Twenty-nine percent. That’s a whole lot of percent. That’s nearly a third. And yet most people saw the 71 and read it as certain. The complexity of the alternative is just too taxing to take into account every time we make a judgment. To the vast majority, 71 is synonymous with 100. Clinton is winning.

But what if you had to bet, given Silver’s estimates? Would you bet on a 71 percent certainty the same way as if it were 100 percent, place the same amount of money on each proposition? Or would you then realize that there was a more than notable margin of error? It turns out that the odds of Trump winning are roughly the same as the odds of flopping a pair in hold’em—and you only have to play once or twice to realize that the odds of flopping a pair are a far cry from zero.

Nate Silver is a poker player. In fact, once upon a time he made quite a tidy living playing online. And poker has taught him something fundamental about the nature of the world that most of us simply never bother to grasp. Poker is such a powerful window into probabilistic thinking not in spite of, but because of, the betting involved: the betting in poker isn’t incidental. It’s integral to the learning process. Our minds learn when we have a stake, a real stake, in the outcome of our learning. It’s why kids learn so much better—and remember what they’ve learned—if they know exactly how or when they’ll apply the knowledge. This is the partner element to learning probabilities from experience: not only do we understand what 29 percent feels like; we now retain that knowledge because if we don’t learn, it hurts us. If we keep betting the wrong amount, we will be punished. If we keep saying “I think I’m good here” without quantifying how often we’re actually good, we’ll lose all our money.

But in life, we normally do just that without a single thought. Why did I buy that stock? Another investor said it was good over lunch. Why did I sell that? Well, he shorted that one and that sounds right to me. We react emotionally rather than looking at the statistics: traders sell winning stocks to lock in the wins—it feels good, even though the numbers say that winners continue to go up in the short term; they hold on to losers to avoid locking in the losses—that would feel bad, even though the numbers say you should cut and run. In fact, numerous studies show that professional investors have a remarkable ability to ignore statistical information for their own gut and intuition—and that they’d often be better served not trading at all as a result.

“For a large majority of fund managers, the selection of stocks is more like rolling dice than like playing poker,” says Daniel Kahneman, the Nobel-winning economist. Not only do most funds underperform the market, but the correlation in year‑to‑year performance is incredibly low. Kahneman continues, “The successful funds in any given year are mostly lucky; they have a good roll of the dice. There is general agreement among researchers that nearly all stock pickers, whether they know it or not—and few of them do—are playing a game of chance.”

It’s a difficult lesson to internalize outside the poker table. Even people who seem like they suffer consequences, like stock traders, are often loath to admit that they were wrong in their certainties. Because the world is much messier than the poker table, it’s far easier to blame something else. It’s easy to have an illusion of skill when you’re not immediately called out on it through feedback. Poker rids you of the habit in a way nothing else quite does—and in so doing, it improves decisions far afield from the game itself.

When I’d just started dating my husband, he would often fact-check me mid-conversation. I’ve never invested anything in my life, but I did in the past have a habit of investing my statements with perhaps a bit more certainty than they warranted. “Are you sure?” he’d ask, endearingly. “I think I might want to check that.” And he would pull out his phone or a book to do just that. I got better, but I could never quite kick it. It wasn’t until I entered the world of poker that the process really sank in. I hadn’t been playing long before I found myself saying things like “Well, I’m about seventy-five percent sure.” I’d experienced the consequences of improper certainty a few too many times in my bank account—and knew that I had been the only one to blame for my bad play.

That personal accountability, without the possibility of deflecting onto someone else, is key. One specific class of lawyer, in fact, actually fares far better at probabilistic thinking than financial professionals whose jobs are more explicitly tied to probabilities: the lawyers who take cases for a percentage of the eventual settlement. You have a far higher personal stake in calibrating correctly, and so you learn to do just that. Likewise, meteorologists and horse-race handicappers: their calibration of risk is accurate because they not only deal explicitly in percentages but have immediate feedback on their performance—and no one else to blame if their estimate is incorrect.

Outside the realm of games, accurate probabilistic thinking is a rare skill. Dan Harrington, one of the greats of the poker world, left poker some years ago to start a real estate business that has performed very well. He told me the story of one hire that hadn’t gone according to plan. He’d seemed nice and qualified, but his judgment ended up leaving something to be desired; it wasn’t nearly as sharp as it had seemed during the interview process. There was a key difference between him and other employees: he had a traditional finance background; the others were connections from the poker and backgammon worlds. “My partner said to me, ‘Dan, in the future if we hire a nonprofessional gambler, just give me a swift kick in the ass,’” Dan remembers. “The successful hires understood equity and they understood the decision tree matrix that that involves, and they don’t get involved in it personally. And that comes from gambling. It’s invaluable for life.” They never hired someone who hadn’t spent some time in the world of gaming ever again.

I’d wager it’s no coincidence that the father of probability—the first person who we know of to go beyond a vision of chance as some sort of unknowable goddess, or otherwise in the purview of the supernatural—was a gambler. Girolamo Cardano was a doctor, a mathematician, a philosopher. He was part of the group responsible for the advent of higher algebra and was known for his thought-provoking prose (Shakespeare, it seems, was a fan, and it has been claimed that Cardano’s Consolation was the book originally held by Hamlet in the “To be or not to be?” scene). He also made much of his money through gambling—but gambling in a way that was foreign to his contemporaries.

Cardano had little patience for the prevailing divination methods of the day. Astrologers may claim to see the future in the stars, but, Cardano wrote, “I have never seen an astrologer who was lucky at gambling, nor were those lucky who took their advice.” Likewise, geomancy, which he called “an unstable vanity and dangerous.” (I had to look up the meaning of “geomancy.” It is divination from markings on the ground or soil.) In 1526 this was quite the outlier opinion. Remember, we’re talking about a time when people were sometimes burned to death for saying that the earth wasn’t the center of the universe. Astrology seemed like cutting-edge science.

Trusting in luck as a vague sort of higher power, Cardano realized, was a losing enterprise. It was pointless to try to divine whether there was a god or spirit or other guiding force at play. He offered another way: prediction through probabilities. He remembers the moment he realized he could make certain plays based on specific frequencies being in his favor. He’d lost a lot of money to a man who had lured him into a game with marked cards. In contemplating how to regain his belongings (he’d also lost many of his clothes and personal effects), a more mathematically minded approach came to him. He not only won back his opponent’s ill-gotten bounty but published his thoughts in the first known book on probability, The Book on Games of Chance. (It was published in 1663, long after his death.)

It just so happens that, in musing on the ways to calculate dice throws and card distributions, Cardano also wrote a description of what many take to be the earliest form of poker, primero. It wasn’t played with a full deck, and the rules of betting were somewhat convoluted, but the essence was similar to the games we have now: some cards private, some in common, and a complex interplay between representing the hand you may or may not have and interpreting the signals of your fellow card players. Primero traveled across Europe, variably termed primiera, la prime, and eventually pochen, a German name derived from the verb “to bluff.” The French took pochen and made it poqué—and soon, the game would morph into a new form.

No one knows quite when it made its way across the ocean, but it seems to have taken root, as so many national pastimes, in the muggy heat of a boring summer. It was 1803, and some Frenchmen in Louisiana had grown listless aboard a slow-moving steamship bound for New Orleans. They started up a game of poqué, which would soon spread gradually by steamboat throughout the new country, eventually becoming poker. And in a sense the theory of probability traveled apace with the game.

Cardano lamented one thing, though. Understanding probability wasn’t enough to tame the luck factor. Unless you cheated—and he spent quite some time describing how that would be possible, with crooked dice and marked cards—you had no way of winning consistently. His findings “contribute a great deal to understanding but hardly anything to practical play,” he reflected. Not entirely true, but you can see the sentiment: if you want to improve your odds, understand probabilities; if you want a sure thing, rig the deck.

Poker isn’t just about calibrating the strength of your beliefs. It’s also about becoming comfortable with the fact that there’s no such thing as a sure thing—ever. You will never have all the information you want, and you will have to act all the same. Leave your certainty at the door.

BABA ANYA IS NOT convinced. Poker may teach you that nothing is certain, but she is still positive I’m going over to the dark side. I realize that nothing I say will change her mind. She waves away all my talk of skill with a dismissive hand. She has more arguments in mind.

“But this isn’t serious,” she says. Skill or no skill, there is one other element of this whole thing that bothers her. “It’s only a game. How can you be serious about a game?” She wants me to be a professor—now that’s serious business. A real job. A skilled job.

Until it isn’t. The more I think about it, the more I start doubting just how much of a gamble-free endeavor it could be. Imagine me going down the academic path. What did I choose to study? Social psychology. Ah, but neuroscience is having a moment. I may have followed my interest, but not the job market. With whom did I study? Good luck to me getting a job in any psychology department where the Big Five personality traits are still big—I studied with Walter Mischel, and he and the Big Five are not on speaking terms. What about academic publications? Who might get assigned to review my manuscript—someone with a sympathetic ear or someone who thought my research was so much hogwash? I’m not going to get kicked out of a poker tournament for choosing a style of play that goes counter to the strategy of the bigwigs of the day and may challenge their ascendance. But if I were to go against the head of a department or hiring committee—or even one of the celebrity hotshot professors? Bye-bye, job prospects.

In many ways, poker is the skilled endeavor. The job market is the gamble. How did my job talk go? Where did I go to college? To grad school? Did I rub someone the wrong way in an interview? These details, all subject to a big dose of chance, can make or break me. At the table, I play how I play. And I rise or fall on my own merits.

“BUT WHY COULDN’T YOU have maybe played chess instead?” My grandmother talking again. “Now that’s a respectable game.”

I let out a final sigh. How I wish I could take her on a walk to Washington Square Park so she can see the actual chess players. Between the hustle and the side hustle, it’s some of the most intense betting I’ve ever witnessed. “I feel a connection to these people,” Erik tells me once, during a walk in Washington Square. “Because they’re games players. They hang out, play chess, sometimes backgammon. They get it.”

But I’m out of energy. I don’t dive into my lecture about chess being a game of perfect information and life being a game of uncertainty. And I don’t mention Washington Square. I’ll just have to get on with it and hope to prove myself along the way.

The Art of Losing
New York, Fall 2017

“If you can make one heap of all your winnings

And risk it on one turn of pitch and toss,

And lose, and start again at your beginnings

And never breathe a word about your loss …”

RUDYARD KIPLING, “IF—,” 1943

I wake up bleary-eyed, my tail decidedly un‑bushy, to the sound of the harp alarm on my phone. It was chosen to be less jarring than the alternatives; instead, it makes me hate harps with unhealthy fervor. It’s six in the morning—not a time a self-employed writer usually sees unless she has stayed up all night writing. But I need to get from Brooklyn to the Upper West Side by eight. Erik, it turns out, is an early bird. Eight was the compromise time, not the opening bid.

The lesson begins, as all New York lessons must, with lox and bagels. We’re sitting at the Fairway Market Café, and Erik is eager to hear about my progress, which has, thus far, been admittedly theoretical.

“How was the meeting with Dan?” he asks.

Dan is Dan Harrington, or Action Dan as he’s often called with a wink, for his seemingly conservative playing style. He and Erik go way back, to the days when Erik still played backgammon and the Mayfair Club was still a private poker club in New York where many of the future greats cut their teeth. It was 1979, and Erik had come up to Boston, across the river from Harrington’s hometown, for a backgammon tournament. Dan had been around the backgammon scene for some time; Erik was the newcomer, “this nineteen-year-old whiz kid,” Dan recalls. They made it to the end of the tournament: it was down to the old stalwart and the young whiz.

Dan won. “I played well,” he tells me, “and Erik just said, ‘Who the hell are you? I never heard of you before.’ Because he’s from New York, and New Yorkers have this attitude that nothing exists outside of New York.”

Erik figured out who the hell Dan was, Dan became interested in poker, and six years later they met a second time, at the Mayfair. It was the start of a lifelong friendship. Dan is now retired from the poker world—“I got too old,” he says. “This is a young person’s game, believe it or not. A miracle is someone like Erik. The fact that he continues to do this at this age is just absolutely astounding. I did it at his age, but it was a much weaker field.” But his accomplishments include the one thing everyone covets, the title of World Series of Poker Main Event champion. He can also boast a record four Main Event final tables, including a third-place finish in the year made famous by an accountant, Chris Moneymaker, winning the top prize and starting the modern poker boom, the so‑called Moneymaker effect.

Finding a good mentor is crucial to learning any new skill—and one of the things the best mentors do well is know when to delegate. It’s been decades since Erik opened David Sklansky’s The Theory of Poker, the book that first propelled him into the poker world when he picked it up on a whim in a used-book shop. And he isn’t used to taking on students, let alone those who know nothing about the game. So for the basics, he’d sent me to the person who wrote the textbook—literally. Harrington on Hold’em is a classic. Erik may not have given the basics much thought since Sklansky, but Dan Harrington had distilled them for thousands. And luckily for me, he happened to be in New York.

“I think it went really well,” I tell Erik. “I learned how to beat roulette.”

DAN AND I MEET at the Midtown hotel where he’s staying on his visit from the West Coast. I’m not sure what to expect but am pleased when he greets me wearing a white baseball cap—in all the photos I’ve seen of him, he has on one hat or another. I’ve read his books and can’t quite believe he’s willing to go through the nitty-gritty of poker with me.

We bond immediately as we head to the café for some breakfast. We both grew up without much money, it turns out. I tell him how lucky I am that my parents are supportive of this latest adventure, cheering me on despite the financial risks, but confide that my grandmother has slightly different views.

And he tells me that those views may never change, no matter what I do. He recalls the moment he told his mother he won the World Series of Poker. “Well, what do you think, Mom? I won a million dollars. I’m world champion of poker!” he remembers telling her. And she replies, “Oh, that’s great, Danny. You know, we have a cousin, Pádraig Harrington. He’s a golfer, and he just won eighty thousand dollars over in the Spanish Open.” Dan persists. “Mom, I won a million dollars. I’m world champion.” And she has one answer. “Listen, Danny, he’s doing well on the European tour.”

“So what do you want to know?” he asks me, between sips on a morning coffee.

Everything, I tell him. I want to know everything.

I’m expecting a lesson in beating the odds, in calculations, in the power of position and optimal strategy. And I do get some of that—but what I mostly get instead is a crash session on the importance of failure.

“Look, you’ve read my books,” Dan says. And I have. It was the first step in Erik’s lesson plan for me, what he called the foundational element of my journey. Before I did anything else, I went out and bought copies of Dan’s books—and read them, pen in hand, cover to cover. Let me tell you, my margin notes would make a literature grad student pale with envy. I’ve meticulously gone through each section, highlighting, underlining, filling up pages with marginalia. I may not have known how many cards are in a deck until a few weeks ago, but this I was born for.

Erik has never taught anyone before, and his own early experience is not particularly applicable to me—I don’t have any current plans to stop everything and start spending all my time at the modern equivalent of the Mayfair Club, butting heads with the best players in the world for days on end. What’s more, the world of poker has changed a great deal since he came up. For one thing, there’s online poker, which means you can get more experience in less time than ever before. For another, there are powerful computer algorithms that help you work out strategies and run millions of simulations in seconds to answer strategic questions that used to be approached by the brunt of sheer repetition and experience. Dan’s books are the closest thing he can think of as a primer to everything—a way of setting up the basis of my journey without overwhelming me from the beginning.

“At least I think they’ll be OK for you,” he says at first. “Let me know how it’s going. If it’s too hard, we’ll think of something else.”

Through the waning days of summer and into the early fall, the margin notes are my life raft. They are the only thing I have that is concrete—and my only sign that I am learning anything at all. Erik has been clear from the beginning: certain markers have to be met before I can move forward in my poker journey. If I’m to work with him, I can’t skip steps. First I read and watch—read Harrington, watch streams with real hands being played by the best players. (“Sign up for Run It Once,” he tells me early on. I find out it’s a coaching site, and when I start looking at the library of available topics, I suddenly feel very, very lost and very, very small and very, very silly. What was I even thinking? What in the world is a merged three-betting range and why does turn bet sizing on three-flush boards merit multiple hours of conversation?) Then we discuss—I ask questions and Erik determines that I have enough of a theoretical basis to get started playing without completely losing my shirt. Then I begin to play for real—online, for tiny stakes, but for real money, to see how I do in putting the lessons into practice. Play money simply won’t cut it. Plenty of people who kill at Monopoly would make terrible real estate agents. Only after I start consistently winning money online will I get to do the thing I thought I’d be doing right away: going to Vegas to play in real life—somehow, online doesn’t feel like real life even though the money is real enough—in real casinos, at real tables, with real chips. (I’ve already bought my very own chip set in preparation. I’ve seen the videos, after all, and everyone knows how to do that thing where you mix two stacks of chips into one with your hand. Riffling, I find out it’s called. The first time I try it, the chips fly all over the room in a flurry of red and green. I quickly find a YouTube tutorial and start to practice. “Maybe focus on learning to play first,” my husband gently suggests when he happens upon me devoting a little too much attention to my new dexterity challenge.)

Even from Vegas, it’s still a long road to the WSOP. The Main Event is a $10,000 buy‑in. That’s high stakes for an amateur who knows nothing. If I’m not prepared, it will be the rough equivalent of taking the bills and using them as kindling for a really lovely bonfire. A beautiful experience of warmth and color, quickly followed by ash and a slightly unpleasant odor of smoldering wet coals in the air. Erik is nothing if not responsible. And he takes his role as mentor quite seriously. If I want him to be my coach, I have to agree that he will not be letting me anywhere near a $10,000 tournament, book or no book, if he doesn’t feel I at least have an outside chance at success. For that to happen, I have to get to the point where I’m consistently cashing in lower-stakes tournaments, working my way up from the smallest to the bigger ones.

It’s already September. The Main Event will be in July. That’s ten months—a bit under a year. And I’m not even to the point of having played a single hand in an actual game, live or online. So I’m holding on tight to those Harrington books. If I read them closely enough, I’m hoping, they’ll provide enough of a boost that the rest will go quickly and smoothly. It doesn’t bode well that it’s taken me far longer to get through them than I’d planned—it’s a new language for me, just as Erik told me it would be—but I remain the endless optimist. At least when I have a book deadline to hit.

And so before I ever met Dan in the flesh, I not only read his books. I reread his books. I dissected his books. Erik and I have spent multiple sessions, over multiple weeks, going through my notes and questions one by one to develop a working base of how to play. These haven’t been your traditional lessons. We don’t sit and review. There are no lesson plans. There are no specific topics to cover or goals to hit. Instead, we walk. Erik is a big walker. Ever since he got a Fitbit, some years ago, he has been religious in hitting his daily step count, and as I will learn, walking is a big part of his routine, come rain or shine, in New York or Vegas or anywhere else in the world, whether he’s in between playing or in the middle of a tournament. It’s not just for exercise. It’s his way of thinking, his way of reflecting, his way of relating, his way of learning.

We walk, we talk, and we let the pace of the afternoon determine the flow of the conversation. As the majestic Hudson glitters blue on our left and the flowered carpets of Riverside Park open up on the right, I try my best to keep up with his long strides while strategically perching my phone on the side of my bag to record the conversation, alternating between fishing a dog-eared Harrington out of said bag to find the pertinent pages and holding a mini notebook to jot down especially important thoughts that I want to make sure to revisit. It doesn’t help that I’m not the most coordinated person in the world, and I often find myself performing interpretive dance moves to catch a falling phone or pen while trying to not break stride. I’d like to tell Erik that his step count doesn’t care about how quickly those steps were taken, but I don’t quite have the breath left to do so. We must look like a very odd duo.

Our earliest walking conversations are, as you’d expect, among the most basic. I’ve drilled down the super basics—the ground rules, so to speak. You are dealt two cards. You decide whether to play them or to fold. If you do play them, you call or raise. Everyone else follows the same decision process, going in a clockwise direction starting from the player to the left of the big blind, a position called, appropriately enough, under the gun. And then you make that decision again every time new information, in the form of new cards, appears. At the end, if only one person holds cards when the betting is done, she wins the pot. If the hand goes to showdown—that is, the final bet is called—the person holding the best cards will win. In rare cases, the pot can be split if the cards are the same, or if both players are playing the board, or the community cards (that is, when what’s on the board beats the individual hands). But what of the slightly less basic basics?

“Harrington is big on different types of players,” I report to Erik. “Are you a conservative player, an aggressive player, a super-aggressive player, or this or that?”

“I don’t think you need to decide that at this time,” Erik says, laughing. “But I’m glad he’s laying out all those approaches.”

“Well, why would I ever want to be anything other than super aggressive?” I ask. “He basically says that the only players who he can’t ever really predict are the super-aggressive ones, because they’ll play any hand, so it’s impossible to tell what they’re holding at any given point. But if that’s true, why wouldn’t you always want to play like that?”

One of the first things I’ve been learning is starting hand selection: I know you get two cards and have to decide whether to play them or not, but what cards should you be holding, at what position at the table, to decide that your hand is good enough? Erik has explained that the earlier you open, the stronger your hand needs to be, because more players are still to act. That makes sense. In any decision, information is power. The earlier you act, the less information you have. With multiple people still waiting to make their decision, the landscape may well change. He’s talked about the value of various starting possibilities. The pocket pairs—two cards that are the same. The suited connectors—cards of the same suit that are one apart in ranking, like a seven and an eight. The suited one- and two- and even three-gappers—cards of the same suit that are sort of related but not immediately adjacent, like a six and an eight of hearts. The suited wheel aces—an ace with a low second card of the same suit that can make a straight, or a wheel. They all have different strategic value, he’s told me. They all need to be part of a well-rounded arsenal. Some are good on their own. Some are good because they give you board coverage—that is, you can make strong hands in a variety of situations. Some are worthwhile for blocker value—key cards that lower the chance your opponent has a strong hand. Some are powerful because they can make monster hands that will get maximum value from weak opponents. And he’s explained how you can’t play all those cards in the same way all the time, especially given my lack of experience. “Basically, you can’t go too wrong in the beginning if you play good cards” is one of the first concrete pieces of information he ever gave me. But what Harrington seems to be saying makes a lot of sense to me, too: If I suddenly start opening hands that aren’t expected of me, in super-aggressive style, how will people know how to react?

Erik starts laughing. And the way he begins to say, “Well …” sounds an awful lot like the Well … I give to aspiring writers who’ve just read Kerouac for the first time and are having a mind-blowing epiphany that I already know is not going to end the way they think it will. “Well, there’s definitely an appeal to it. Aggressive people are going to get you. They are going to get you in a lot of spots where you’re going to be like, you know, I can’t handle the pressure or whatever. They’re very good at finding that,” he says. “But they also could get themselves in spots where they’re giving away a lot. I agree with Dan that they’re really challenging to play against and you don’t necessarily always want them at your table—but then you’ll get a beautiful gift from them. You can forgive them anything then.” By beautiful gift, Erik means a lot of chips. Hyper-aggressive play, he tells me, can be a short-term boon. But most of the time, those players go broke. And at the highest levels, they don’t last more than a heartbeat.

My enthusiasm for this particular section of Dan’s work, he says, reminds him of poker as it was ten or so years ago. “There was a time when these hyper-aggressive guys could do very well. Some of them were stars. And then the overaggressiveness ironed them out. They’re on the rail now. You have to find the balance, and some of these guys don’t put the brakes on, ever. In the highest buy‑in events, in the hundred‑Ks, you really have to be able to put the brakes on. There’s an entirely different style, winning a two-hundred-dollar online tournament and winning a hundred‑K.”

So what’s the answer? Action Dan and Erik himself actually offer a pretty compelling case study by their success: Be solid, fundamentally. Cultivate the solid image. And then add the hyper-aggression, but at the right place and the right time. Not always, not continuously, but thinkingly.

There’s never a default with anything. It’s always a matter of deliberation. Even seven-deuce—the worst hand, statistically speaking, that you can be dealt—can be playable in the right circumstances. The thing is, the circumstances are usually not right—and the hyper-aggressive player may run over everyone for a while and forget that at some point, it will all come to a screeching halt. Of course, being too conservative is also a liability. You become predictable. And often times, you lose the ability to press the fold button. You’ve been waiting so patiently for a good hand that you won’t let it go. “If you want to be good in big tournaments,” Erik tells me, “like, let’s say you’re playing a field of four hundred people. You have to be involved in many more hands, because just good cards aren’t going to get you there. They’re not going to get you there a high enough percentage of the time.” And so despite knowing fundamentally sound strategy, you have to be willing to part with it. “It turns out that people who are sort of involved and reckless are more likely to go deep.” To go deep means to make it through a large portion of the field. “You just have to be smart about it.”

I nod. It’s not the answer I wanted, but it’s the answer I get. There’s one more question from the Harrington books that I want to ask before this particular walk is done. What exactly is “M” and do I care? It’s a term I’ve circled in red, to make sure to review. It seemed awfully important to be designated with a single letter. M, Erik explains, is a way of thinking about your position in a tournament. “You have to be aware of everyone’s stack size,” he tells me. “When you get to Vegas and start playing, I want you to write down hands for me. And for every hand, you need to tell me how much everyone has behind. You have to always be aware of it.” Normally, people think of stack sizes in terms of big blinds. M takes it one step further, by quantifying your risk of going broke. How many orbits around the table can I sit and not play a hand? Your M is, basically, your cushion for putting in the minimum each orbit. The lower your M, the more in danger you are of busting the tournament sooner. And the letter M itself? It comes from the last name of a player named Paul Magriel. “I want you to meet Paul when you’re in Vegas,” Erik tells me. “You should ask Dan about him. Tell him to tell you how M came about.”

But as it turns out, I forget to ask Dan. Mostly because he cuts off any more technical questions with one thought. “We can go over everything you should be paying attention to, but the truth is, until you start playing a lot, it’s just information overload.”

I nod. I certainly know the dangers of too much information in an experience-free vacuum. And I realize that my piles of margin notes and the barely legible notebook jottings of Seidelian wisdom don’t necessarily need any more friends, at least at present.

“But here’s what I can tell you. The thing you have to conquer most obviously is yourself,” Dan continues. “Mike Tyson said it best. ‘Everyone has a plan until you get punched in the mouth.’ And he’s right. Until you go through a month of everything going wrong, you won’t know whether you have what it takes. You will never learn how to play good poker if you get lucky—it’s as simple as that. You just won’t.”

He’s not talking about hazing. It’s not the attitude of “no pain, no gain.” Nor is he giving me “permission to fail.” Instead, he’s talking about something very different, something so fundamental that we often forget about it whether we’re learning something new or just going about our lives: you need a way of testing your thought process. Before I get fancy with strategy, with the curlicues and trappings of expertise, I need to answer something far more basic: Am I thinking correctly? Before I start experimenting with writing free verse, have I learned how to think through a poem’s basic structure? Before I start adding those exotic spices to my recipe, have I learned how to make a basic white rice?

And the only way to do that is by failing. By writing bad poetry. Burning your food. Turning in shitty first draft after shitty first draft. “You have to suffer defeat,” Dan continues. “As brutal as it sounds, that’s the way it is.”

The benefit of failure is an objectivity that success simply can’t offer. If you win right away—if your first foray into any new area is a runaway success—you’ll have absolutely no way to gauge if you’re really just that brilliant or it was a total fluke and you got incredibly lucky.

The real reason Erik is still around, Dan tells me—I’ll have to see if Erik agrees on this one—is that he can take chances but still retain enough balance to pull back. Action Dan got his nickname because of a conservative image. Erik isn’t always known for running wild bluffs. “There are many great players who play with a lot more courage than Erik or I will ever know. The trouble is, that’s inherent in their personality and that contains the seeds of their destruction.” They go on hot streaks—but they don’t know what it takes to lose with grace and keep going. “You’ll see a whole bunch of superstars from ten years ago, and you’re not going to find any with money today. They were superstars because they were able to bring it to the edge, they had ability, but when things went a little bit wrong they either fell apart or didn’t know what to do with the money and spent it all on drugs and sports betting. So were they actually courageous? No.”

Nothing is personal. Everything should be treated like a business. My goals need to be pure: to run the best business I can. “Some of these other people had a goal to become famous, or even more, they just wanted action,” Dan says. And that’s their eventual downfall.

Do I know what I don’t know? Am I thinking well? “As a professional gambler, you have to understand: if you don’t have an objective evaluation of what’s going on, you’re a loser,” he tells me. “This game will beat you—it’s as simple as that. If you don’t understand what’s going on, the game will say, ‘We’re taking your money away from you.’”

What’s crucial, Dan says, is to develop my critical thinking and self-assessment ability well enough that I can constantly reevaluate, objectively, where I am—and whether where I am is good enough to play as I’m playing. It’s not about winning or losing—that’s chance. It’s about thinking—the process. Dan himself is a living illustration of how true this is: he quit not during a downswing but at the top of his game.

“Nine years ago, I’d just won $1.63 million. I’m walking out of the tournament, and I look around, I say, ‘This is it. I can’t take this crap anymore. I win $1.63 million and all I do is feel tired and beaten-down. This is just not worth it.’ I just right then and there decided I wasn’t going to play serious poker anymore. My heart’s not in it.” Most people won’t tell you to quit after the biggest score of your life. But Dan could tell that he was getting weaker, he was getting older, and the field was getting stronger. He’d quit before he had fallen behind.

And thus my first real poker lesson isn’t about winning. It’s about losing.

“You become a big winner when you lose,” Dan says. “Everyone plays well when they’re winning. But can you control yourself and play well when you’re losing? And not by being too conservative, but trying to still be objective as to what your chances are in the hand. If you can do that, then you’ve conquered the game.”

And it resonates. After all, losing is what brought me to the table in the first place. It makes sense that learning to lose in a game—to lose constructively and productively—would help me lose in life, lose and come back, lose and not see it as a personal failure. It resonates—but it’s a tough ask. Dan nods. “It’s still tough to do. Even for me, and I have a lifetime of experience, that’s not an easy thing.”

We say our goodbyes. He missed his morning gym session, but he’s off to enjoy his “quiet retirement.”

Oh, and I did learn how to beat roulette. Turns out all you need is a Department of Defense supercomputer, a software program developed from the work of Claude Shannon and Edward Thorp in the fifties, and an earpiece. Also casinos that don’t know what you’re up to. Get too greedy and you’re out.

“DAN IS GREAT,” ERIK agrees. And, yes, everything he has told me is true: one of the keys to success, Erik says, if not the key, is objectivity. And objectivity is a hard thing to come by.

“It’s good that you’re starting with a rare realistic understanding of what you’re up against,” he says. “You know that these swings happen, that there’s a randomness to the way these swings happen.”

It doesn’t make me feel much better. I’m a writer, I want to remind him. I don’t have much money to lose. It’s easy enough for someone with over $30 million in earnings to say.

But actually that’s unfair. When Erik was just starting out, he had nothing—and he nearly lost it all. He’d dropped out of college to play backgammon—that’s when he first met Dan—but then decided to go back to a more traditional career path. He’d met his future wife, Ruah, and knew he had to get “serious” about life. So he went to Wall Street—just in time for the crash of 1987. He lost his job. And Ruah was now pregnant.

He didn’t take the loss personally. Instead, he reevaluated his options and buckled down on his studying. He was, in essence, “scared into playing well.” And he started winning. Why did he emerge on the other side while so many others didn’t? Obviously, there’s the talent factor—Erik is clearly someone who is very good at the component parts of poker—but there’s a larger skill at play: his absolute lack of ego. His willingness to be objective about himself and his own level of play.

“When things go wrong, other people see it as unfairness that’s always surrounding them,” he tells me. They take it personally. They don’t know how to lose, how to learn from losing. They look for something or someone to blame. They don’t step back to analyze their own decisions, their own play, where they may have gone wrong themselves. “It’s a really big handicap in life to think that way. All of us can step into that sometimes, but it’s important to know the difference. It’s like that great Kipling quote: ‘If you can meet with Triumph and Disaster, and treat those two impostors just the same …’”

I nod. I know the one.

“I love that. This is such a fundamental part of poker. The wins really go to people’s heads. And the losses—they can’t deal. It’s so easy to be delusional in this game,” he tells me.

I jot it down. Understand the dark side of variance first: that’s the only time you’ll actually learn to process your decision making well. Because when you’re winning, it’s just too easy not to stop and analyze your process. Why bother if things are going well? When it comes to learning, Triumph is the real foe; it’s Disaster that’s your teacher. It’s Disaster that brings objectivity. It’s Disaster that’s the antidote to that greatest of delusions, overconfidence. And ultimately, both Triumph and Disaster are impostors. They are results that are subject to chance. One of them just happens to be a better teaching tool than the other.

In the classic demonstration of the illusion of control, the Harvard psychologist Ellen Langer had students guess the outcome of a coin toss, heads or tails. They were then told whether they were correct or not in their guesses. In three separate setups, the outcomes were predetermined in a specific order: they could be distributed in an intuitively random pattern, there could be more correct guesses clustered near the beginning, or there could be more correct guesses clustered near the end. In each case, the absolute numbers were the same. The only difference was the order.

But the results couldn’t have been more different. After the guesses concluded, Langer asked each participant a series of questions: Did they feel they could improve on this task? Did they feel they were particularly talented at it? Did they need more time to get better? Would they be better with limited distraction? And so on. In each case, the obvious answer is no: to answer otherwise is to classify something that is the outcome of chance (a coin toss) as being in the realm of skill. But the obvious answer is not the answer she got. When students had a random progression or one where the accuracy clustered near the end, they did indeed answer in the negative. But when the correct answers were clustered up front, they developed a sudden myopia. Why yes, they said, they are quite good at this, and yes, they would improve with time. Success led to an abject failure of objectivity: suddenly, they were in the throes of the illusion of control. They thought that they could actually predict the results of a coin toss.

If we lose early, we have a shot at objectivity. But when we win at the start, that’s when we see the illusion of control playing out in full swing. As Langer titled her paper: “Tails, I Win. Heads, It’s Chance.” Though Langer’s work is from the seventies, when I was in graduate school, Walter and I replicated the effect precisely with our new subjects: it remains just as strong. The outcome rightly shouldn’t matter. And yet how it does.

“The beauty of poker is generally, delusion is punished,” Erik tells me. You may get away with an illusion of control in the short term, but if you persist, no one will know your name in a few years’ time. In real life, we can remain deluded indefinitely. If we choose delusion over objectivity in poker, we are eventually doomed.

I admit to being nervous. Objectivity at its purest is a big ask. Can I truly hack it?

Erik certainly can. Somehow, even over smoked fish, he manages to demonstrate just how able he is to learn from feedback and to change his actions accordingly.

“Do you not like the way egg yolks taste?” I ask him as our orders hit the table. I’ve ordered the lox and bagel platter. He’s ordered some salmon, too, but also an egg-white omelet, just as he had at our first ever meeting. To me, that seems like cutting out the part that makes eggs eggs, and even though I don’t yet know Erik well, I can’t help but comment.

“No, I like them,” Erik says. “But I read that it’s healthier to only eat egg whites.”

I’ll soon learn that Erik is big on nutrition science—but that he’s always willing to listen if someone points out contradictory evidence. Which is precisely what I now do, even pulling out my phone to punctuate my mini lecture with references to newer work. Nutrition is a tricky beast, and nutrition advice offered in a vacuum, even trickier. Many people will bristle and shut down—who are you to tell them what to eat when they’ve already formed an opinion? Erik listens. He reads. He nods. And the next time we have breakfast, he orders the full egg. I resist asking if it tastes better, but I imagine I see a satisfied look on his face. I take out my phone again, this time with a quote I pulled from one of my favorite Nora Ephron essays. “You can eat all sorts of things that are high in dietary cholesterol (like lobster and avocado and eggs),” she writes, “and they have NO EFFECT WHATSOEVER on your cholesterol count. NONE. WHATSOEVER. DID YOU HEAR ME? I’m sorry to have to resort to capital letters, but what is wrong with you people?” She reserves special pity for the egg-white omelet. “Every time I’m forced to watch [friends] eat egg-white omelets, I feel bad for them. In the first place, egg-white omelets are tasteless. In the second place, the people who eat them think they are doing something virtuous when they are instead merely misinformed.” She goes on to say that no amount of haranguing from her tends to change anyone’s mind—a common enough effect, especially when it comes to nutritional beliefs. Erik laughs and eats his eggs, yolks and all.

AS I RIDE THE subway back to Brooklyn, I realize Erik hasn’t given me much in the way of concrete advice. Our conversations remain more theoretical than I would ideally prefer. It strikes me that the experience feels somehow familiar, this dynamic of back-and-forth with no real answers forthcoming to any of my questions—or, rather, the only answer being one of “Well, it depends; why don’t we think it through for ourselves?” It’s not quite a Socratic dialogue—Erik doesn’t keep me hanging to that extent—but it’s an interaction that focuses more on process than prescription, on exploration rather than destination.

When I complain that it would be helpful to know at least his opinion on how I should play a hand, he gives me a smile and tells me a story. Earlier that year, he says, he was talking to one of the most successful high-stakes players currently on the circuit. That player was offering a very specific opinion on how a certain hand should be played. Erik listened quietly and then told him one phrase: “Less certainty. More inquiry.”

“He didn’t take it well,” he tells me. “He actually got pretty upset.” But Erik wasn’t criticizing. He was offering the approach he’d learned over years of experience. Question more. Stay open-minded.

And then I realize what I’m reminded of: Dante and Virgil. Dante, in a strange place, not knowing what anything is or where it might lead. Virgil, his guide through this infernal landscape, who doesn’t offer directions but rather stands to the side as Dante forges his own path.

When people find out I’m working with Erik, they immediately want to know what he thinks of certain plays and how he himself plays certain spots. Will the elusive champion finally give up his secrets? For Erik, the answer is simple: there is no answer. It’s a constant process of inquiry. A hand can be played any number of ways, as long as the thought process is there. And Erik may himself decide to play the same cards, in the same position, even against the same opponents, in a different fashion from one day to the next. There is no certainty. There is only thought.

And yes, it is frustrating. I do want answers. I do want a guide for what to do with my pocket tens from the small blind following a raise from under the gun and a re‑raise from the hijack. Enough philosophy, I want to yell. Give me certainty! Tell me if I’m supposed to call or shove or fold. Tell me if I’m making a big mistake! But the Virgil buddha will not be shaken. And I’m left with that frustrating not-quite-rage that, weeks later, I miraculously find coalesced into knowledge. Poker is all about comfort with uncertainty, after all. Only I didn’t quite realize it wasn’t just uncertainty about the outcome of the cards. It’s uncertainty about the “right” thing to do. The only certain thing is your thinking.

A number of years ago, Erik heard about a seminar led by Mike Caro. Caro is famous for his book on tells—live, in‑the-moment reads of others at the table. “He’s a pretty eccentric guy,” Erik says. “And he’s walking around the stage and starts off by saying, ‘What is the object of poker?’” I nod in agreement. A question I’ve been asking myself frequently.

Erik continues, “Somebody says, ‘Winning money.’ He says, ‘No.’ Somebody else says, ‘Winning a lot of pots.’ ‘No.’ He says, ‘The object of poker is making good decisions.’ I think that’s a really good way to look at poker.”

He thinks for a bit. “When you lose because of the run of the cards, that feels fine. It’s not a big deal. It’s much more painful if you lose because you made a bad decision or a mistake.”

He won’t tell me how to play a hand not because he’s being mean but because that answer comes at the expense of the ability to make a decision. Of the discipline to think through everything for myself, on my own. All he can give me are the tools. The building blocks of thoughts. I’m the one who has to find the way through.

It may make me frustrated in the short term. But at least I won’t be in any danger of falling into the egg-white trap in an area I know nothing about. If you’re skeptical of any prescriptive advice to begin with, if “less certainty, more inquiry” is your guiding light, not only will you listen; you will adjust. You will grow. And if that’s not self-awareness and self-discipline, I don’t know what is.

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