Eat, Pray, Know When to Hold ’Em: A Profile of Annie Duke

This article is a preview of The LARB Quarterly, no. 36: “Are you content?” Coming soon to the LARB shop.

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IN 2004, Annie Duke won the first televised world championship in poker. She would later say that, even though she had been playing for a decade at that point, she felt like an imposter when she arrived as the only woman in the arena. Something like three percent of professional poker players were women when she started, and the numbers have never shifted all that much. The 2004 ESPN event was poker’s coming-out party to national audiences. The game looked like it might have a future as a legitimate, professionalized pursuit, and the pressure on Duke was immense. On live television, lipstick cameras would display each player’s hand to the audience. “[M]y mistakes were no longer going to be private to me,” Duke worried on a 2015 podcast appearance. She felt like she might be exposed, “that everybody was right and I was actually a terrible player. […] I was bad and I had just gotten lucky and now everybody was going to know it and what they were saying was true.” She had bangs and wore a black UltimateBet hoodie, but not sunglasses or a hat. You could see her pale face, tense but serious, through every hand.

Early in the tournament, Phil Hellmuth, then and now a feared champion, berated Duke for folding on a pair of 10s. She had studied the other players, and she thought she had caught one of their tells, a physical tic that gave away his hand. In the moment, Duke felt she had made the right decision. But Hellmuth’s dressing-down got to her. She started tilting, the term in poker for an emotional state where players stop being able to step back from the game and start making bad decisions. She already felt like she had been invited as a token girl, like she was out of her league. And when Hellmuth questioned her, she started to question herself. On break, she tried to pull herself together.

And she did. Duke was able to turn stereotype threat into what NPR’s Hidden Brain called a “stereotype tax.” She took the chauvinistic idea that a girl can’t bluff and leveraged it against the men at her table. During the final hands, when it was just her against Hellmuth, Duke turned on the charm. You can hear it even in the timbre of her voice, when she tells him how well he’s playing, or when she says she feels so lucky to be there.

Hellmuth didn’t think she could bluff him. So he went in hard, and he let the charm offensive throw him off. After Duke’s victory, the camera followed him down a dark hallway as he muttered and cussed to himself in disbelief. He says, “She fucking check-raised me six times, I know she didn’t have it all six times.” This is intercut with Duke laughing and saying, “Oh, my god! I won!” and calling her brother. Hellmuth still can’t believe she beat him. “She had to be fucking 30 to one to win this. I love Annie but …” and more bleeped-out cussing.

Hellmuth got played.

When Duke appeared on The Celebrity Apprentice in 2009, she was widely considered to be the smartest and most ruthless person in the room. She beat Joan Rivers by every metric, but lost the competition on the final task. This was despite — or perhaps due to — the judges siding with Rivers in her startling outburst against Duke, where Rivers yelled about knowing that poker players were white trash with “no last names” and that Duke was a manipulative “whore pit viper” akin to Adolf Hitler.

In 2018, when The New Yorker attempted to profile her, Duke played a game of cat-and-mouse with the reporter, never really letting her in. The headline read: “Annie Duke Will Beat You at Your Own Game.”

Here’s what I can say for sure: Duke stopped playing cards professionally in 2012, but she still talks about it, still seems ready to spar with anyone who tries to impose a narrative on her, and still applies wisdom from poker to life writ large. She has transitioned into a career where she puts her reputation as a particular kind of badass to work as an author, a public poker intellectual, and a financial advisor. Her books and her brand of economic advice have been shaped by the idea that strategies from gambling can be applied to everything. Her 2018 book Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts was cited in The New York Times as “a big favorite among investors,” and Duke now seems to work primarily with behavioral economists and venture capitalists. Her website advertises her as an author, speaker, and “decision strategist.” When she agreed to talk to me, it was to promote her latest book, Quit: The Power of Knowing When to Walk Away.

Duke draws on the ways that poker, unlike chess, involves hidden information, in the cards that are face down and in the luck of the draw — a level of uncertainty that chess doesn’t reach. Chess can be reduced to a finite computation, at which supercomputers excel. Poker’s odds can be calculated, but the game is played, on its fundamental level, against the players at the table. This, according to Duke, makes it more like life.

Thus Duke separates the evaluation of decisions — like the decision to fold — from the evaluation of their immediate results. Did you make the right decision based on the odds, regardless of whether or not you got lucky? That’s how you determine whether you’re tilting or not. In poker, this separation is vital, because it allows you to plot strategy over the course of many hands. At a talk at UC Berkeley, Duke said that most of life’s results are influenced by mountains of hidden information and uncertainty. Your outcomes are determined by two things: “the quality of your decisions and luck. So you better figure out which is which, and then you have to get really comfortable with the luck element, and not obsess about it, because you have no control over it. And then you have to get really obsessed with, How do I improve the decision-making part of my life? Because that’s the thing I have control over.”

Thinking in Bets opens with an example from football, meant to illustrate the ways that people engage in “resulting,” or the way they judge the wisdom of decisions incorrectly based on the results. But Quit returns to cards for its opener, specifically the 1978 Kenny Rogers song “The Gambler.” Duke points out that in the chorus of that karaoke favorite, three of the four things you gotta know are about quitting. Duke sets this somewhat basic card-shark truism off against our cultural fixation on grit. American society is dominated, she argues, by messages about sticking to your guns, believing in your dreams, and never giving up. Duke’s message is to think more about quitting instead — early and often.

There is, of course, some truth to the idea of an American obsession with persistence. There is cruel optimism in the countless stories we tell ourselves about chasing some of capitalism’s more unattainable dreams. However, I also spend a lot of time writing about behavioral economics, Duke’s current intellectual milieu and the public face of business thinking for the gig economy. In the new platform economy, a fetish for quitting fits in with the new neoliberal conventional wisdom. Duke, after all, isn’t talking about dropping out to get in touch with your values as a beach bum or a guru (unless you’ve figured out a way to monetize that). She’s talking about quitting strategically, in service of finding a better gig. She’s talking about quitting as part of a flexible path toward more valuable human capital.

When Duke joined my video call, I could see white bookshelves and a pale blue couch in the background. She appeared as a well-put-together brunette in business casual. She didn’t seem particularly keen to talk at first, but the space looked inviting, like an attic or a loft turned into a light-filled home office. I wanted to take a screenshot, but I refrained. I wasn’t entirely clear on how much access I could ask for on the call. Duke clearly wanted to be interviewed primarily as an author. I had the sense that if I was too probing, she might show me how it’s done — the hanging up and walking away part.

In the postwar Fordist compromise, employers needed workers to master their jobs and stick around, at predictable rates. The Fordist compromise with labor meant that full-time and long-term contracts were both the ideal and the norm. Since the original dot-com boom and bust in 2001, venture capital and Silicon Valley have been dismantling those norms and ideals. More and more of the economy is moving away from long-term salaried work. In the platform and gig economy, there is an ideological motivation for capital to encourage workers to think of themselves as flexible and creative independent operators or project-based contractors. Employers encourage this because it gives them a fluid workforce and new ways to get out of providing healthcare benefits. Workers like some aspects of this, even as we all wake up to the new shape of exploitation. In many ways, then, “optimal quitting,” as Duke calls it, is an important part of surviving in the era of flexible work.

I figured Duke would have plenty to say about the gig economy. But we never got to it because we couldn’t get past the subject of dating.

The following distinction seemed obvious to me: just as a game of poker is qualitatively different from a game of chess, marriage is qualitatively different from a game, period. A relationship offers no moment in time at which it can be evaluated against an objective ranking. Even after death parts us, the living make meaning through the continuous narrative of our experiences. Our relationships exist only over time; there is no point at which you can tally up a score and say that you won or lost your marriage. The window of evaluation on our commitments to other people is always open.

But in our brief call, Duke wouldn’t budge from the idea that marriage is a quantifiable prospect. “Imagine yourself in a year,” she said. She granted that loyalty might matter to some people, but insisted it was just another factor. “On a scale of one to 10, how fulfilled do you feel, forecast how happy you’ll be — how fulfilled do you think you’ll feel, how much joy, given a sense of partnership and duty? — how in love do you think you’ll be? We shouldn’t be scared of that measurement.” She brought up the example of women who stay in abusive relationships. They needed to learn to quit more optimally, she said, presumably with better forecasting of the odds.

As to the value of loyalty, Duke said, “Maybe they never clean a dish; maybe that’s an emotional cost to you. […] On balance, the loyalty is outweighing the cost of doing dishes.” Thus, loyalty is just one yardstick among many.

This just doesn’t quite work. It’s not being scared of measurement to say that you can’t pit loyalty against dishes. They exist on different planes. Loyalty might help you see past the dishes, to something that matters more. But there is no way to measure the ephemeral dividends of commitment and set them against the earthly rewards of youth or beauty. Or chores. Both types of reward are real. But there are real risks to assessing the payoffs of patience or deep intimacy in a cost-benefit analysis that tries to forecast them like financial prospects.

To be fair to Duke, she uses poker-based thinking to encourage a more considered type of probabilistic assessment. In many ways, her advice is fundamentally just this: take a step back and do some critical thinking. Whatever is on the table in front of you, look at it clearly, and you might achieve a certain brand of humility in the face of uncertain realities. Accept what is. Watch for tilt. If you’ve been dealt bad cards, look at them coolly, and fold.

Also to be fair to Duke, there is something about tilt at the poker table that is akin to abusive relationships. When people get hurt, they often spiral and stop thinking clearly. They stop making rational choices, and sometimes they chase their losses with ever more desperate attempts. That’s tilt. We get addicted to outrage and drama, and instead of folding and walking away, we go back spoiling for a bigger fight. Sure.

In her last book, Duke was even more direct about life always being like a game of cards, and she promised that she combined “her experience as a professional poker player with the most advanced thinking on decision making, integrating psychology, economics, game theory, and neuroscience.” She imagines a human subject working to narrow the odds on every outcome, where every grocery line and relationship is an investment of time or money and therefore an investment of personal human capital. She told an audience at Google headquarters that “everything can be quantified” and that these strategies apply to every aspect of her life, from parenting to career choices. She co-founded the Alliance for Decision Education, which supports a national movement “to ensure Decision Education becomes a critical part of every middle and high school student’s learning experience.”

Decision education sounds fine. But who gets to say which decision was correct? Who gets to call it?

I asked Duke if Quit was really a way to get people to meditate on what’s at stake before embarking on their journeys — to get them to look clearly at the possibility of loss, failure, or even death. This was one of the only things I said that she agreed with.

I wanted to press the essentially philosophical point that the game of life is qualitatively different. The cards don’t change, but people change. Life decisions are different not only because of the amount or type of uncertainty, but also because of the way that relationships exist in time. We carry a fundamental ability to redefine what it means to win. Duke wouldn’t cede on this.

As I was pushing Duke on the issue, she told me that she had stayed in poker too long. She mentioned, almost in passing, the end of the boom in the poker economy. So, I took a risk, and asked whether she meant the year 2011. This is a topic she was likely dreading.

In the poker world, the moment that year when US authorities shut down online poker is known as Black Friday. On that day, the Department of Justice went after Duke’s older brother, Howard Lederer. They wanted $40 million.

Lederer taught Duke how to play poker. He was the first person she called when she won the 2004 World Series; he had been knocked out of the tournament earlier on. And she was in business with him through the Costa Rica–based Full Tilt Poker when the DOJ came knocking. As the US Attorney started hunting down Swiss bank accounts, Preet Bharara said that Full Tilt was a Ponzi scheme and that insiders had “lined their own pockets with funds picked from the pockets of their most loyal customers while blithely lying to both players and the public alike about the safety and security of the money deposited with the company.” The government accused Lederer of money laundering and illegal gambling through his online casino in a series of moves that were intended to shut down most offshore operations. Lederer ended up settling. The feds took a set of luxury properties, cars, and a smaller sum from him. But the game had been fundamentally changed. Most of the big money in online poker ground to a halt, and some of the players didn’t get paid. Duke wasn’t directly implicated, but her reputation in the game was wrapped up with Lederer and Full Tilt. These facts are in the public record, but both she and Lederer have avoided discussion of these events. This tricky past clearly motivates part of Duke’s desire to control the narrative. And in her brief conversation with me, she pivoted immediately when 2011 came up.

Instead, Duke began to tell me a story about running into her former dissertation advisor in a doctor’s office.

Years ago, when Duke was in graduate school for cognitive psychology, she fell seriously ill with a stomach problem. She had been about to defend her dissertation. She already had kids. When she got sick, she had to come off the seasonal academic job market. She took time to heal and started playing cards to pay the bills. When she got better, instead of going back to cognitive psychology (a field that has close ties with behavioral economics), she stayed in professional poker. She said that when she bumped into her dissertation advisor, they hadn’t spoken in years. Duke told me that she had carried an “incredibly deep shame” around for 20 years, until this chance encounter. During all her time away, Duke said she had felt embarrassed, as if she had let her advisor and her mentors down, and so she had never contacted them. She deeply regretted the years of friendship she had missed.

“Even though I was a world champion in the thing I had chosen to do instead, I lost two decades with somebody who was one of the loves of my life, because I felt so bad about quitting. But why did I feel so bad about it?”

It was only at this point that I remembered that I had started the conversation with a brief reference to the fact that after a decade as a professor, I was in the process of stepping away from academia. I hadn’t mentioned my dissertation advisor. But did I have to?

When Duke wanted to move me off of Black Friday, she pivoted to a story about disappointment and redemption with an academic mentor. Perhaps she was simply sharing something about a time when it was hard for her to quit, just as I had asked her to. Or perhaps she had picked up on my somewhat obvious tell, that I was a person who would resonate with the special cocktail of shame and attachment that comes with walking away from this particular game.

It almost felt like Duke had played me.

When I realized this, I tried to get even more honest. That was my only move. I said that in the male-dominated worlds of academia and journalism, I have sometimes quit, while other times I haven’t been able to quit because I needed the paycheck. But usually, the thing that helps me is not a cold assessment of the odds but a focus on the people around me, who are not my opponents. Instead of quitting, I’ve tried to think about changing the nature of the game, maybe making more spaces less hostile to more people.

Duke considered this. And then she said, Look: nobody ever made decisions for me. “In my career … it’s very different if there’s a boss who can not promote you, or [who can] decide if you get extra responsibility.”

“I could sit at any table I wanted,” she told me. “However somebody viewed me could have an emotional impact on me, but they couldn’t not promote me. In a space where there’s very few women, in a workplace … well, I can only tell you so much. I didn’t have a boss.”

In these times of mass resignation and quiet quitting, I realized that this is what Annie Duke is really selling — a chance to spend time with her in a sometimes-useful fantasy, where we all have the freedom to ditch our bosses.

Most of us can’t do that, and the game of jobs is always played against house odds. Our relationships still can’t be quantified like bets. The real friendships that can happen at work mean that there are hidden and often incommensurable costs to quitting and benefits to staying. And while most of us will never amass the kind of capital that would let us start our own offshore shop, above and between the laws of any nation, most of us don’t really feel the need to go that far. The true appeal of quitting in the platform economy and the lure of flexibility are mostly about having more autonomy from work. Duke may have played me, but she also reminded me that I need to know my own worth beyond the approval of any one job or mentor, and that sometimes leaving the game is the right move. Especially for those of us who have had the “labor of love” discourse used against us, who have worked too long and too hard for the privilege of doing more work, to prove that we love it — sometimes it can be helpful to imagine a canny poker player as your quitting coach. Take a step back. If your job is damaging to you, don’t tilt. Maybe quit. Or maybe unionize.

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Correction: This article misstated that Annie Duke had children in graduate school. She did not have her children until after graduate school. It also misstated her relationship to Full Tilt Poker: Annie Duke worked in various capacities for Ultimate Bet, which was involved in separate but related legal issues from Lederer’s Full Tilt Poker. In a 2012 press release about Full Tilt, the Manhattan US Attorney’s Office wrote: “In a related matter, the U.S. Attorney’s Office also filed a motion requesting that the court enter a settlement agreement reached with Absolute Poker/Ultimate Bet that requires the company to forfeit all of its assets in order to fully resolve this action.”

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Michelle Chihara is the editor-in-chief of Los Angeles Review of Books.