Know When To Hold 'Em, Know When To Fold 'Em

K-Pop and Poker Bloopers

“You can’t lose what you don’t put in the middle. But you can’t win much, either.”

-Matt Damon, Rounders

In college, I played a lot of poker.¹ 

Terribly.

I could never decide if I was bad at poker because I was gullible² or inexperienced with probability, but either way, I was bad.   Eventually, I realized that I valued keeping my money more than losing it, and decided not to make a career as a dice thrower (as the Talmud warns us).   

My wallet thanks me every day.

However, my terrible impression of Chris Moneymaker ignited a lifelong interest in how to make decisions with incomplete information and the promise, and peril, of developing tunnel vision around results.

We assume that effective leaders have good results, and ineffective leaders have bad results.

But what if that assumption is deeply flawed?

Big Idea: Resulting

Annie Duke was one of the world’s best poker players.   Upon retirement, Duke leveraged her poker experience into a second act promoting “decision education,” as any game of poker potentially involves an infinite number of decisions.     

When teaching about the imperfect relationship between decisions and results, Duke asks people to participate in the following visualization: 

1. What was your best decision over the past year?

2. What was your worst decision over the past year?

No matter the specifics, it is almost certain that the best decision you chose was directly connected to a good result, and the worst decision connected to a bad result.  And while this is understandable, Duke argues in Thinking in Bets that it is flawed and illogical, pointing out that she never seems “to come across anyone who identifies a bad decision where they got lucky with the result, or a well-reasoned decision that didn’t pan out” (10).

In essence, this is “resulting,” the tendency to assume that good results only come from good decisions, and bad results only come from bad decisions.    Instead, Duke argues that “What makes a decision great is not that it has a great outcome. A great decision is the result of a good process” (27).  Over time, effective leaders make more good decisions than bad ones.   But there is a danger in assuming that any one decision can be inextricably linked to the result.    

Consider how this can affect Jewish organizations.   

If any organization assumes that only good results come from good decisions, and bad results from bad ones, it can lead that organization to over-correct in a manner that causes them to struggle more, or under-correct in a manner that ignores the weakness of their system.     Bad thinking can lead to bad decisions, which in turn will cause further struggles, leading to new bad decisions, and so on.    

Duke’s book is a fantastic primer on many of the mental shortcuts that lead to poor decision-making, what are often called heuristics.    We will return to heuristics in future issues, but in the meantime, know that Duke’s notion of resulting is a challenge to the simplistic assumption that good results are co-extensive with good decisions.

Book Summary: The Biggest Bluff

While Duke’s book is a practical guide to decision sciences from a professional poker player, Maria Konikova’s The Biggest Bluff is one novice’s attempt to become a master poker player.    Konikova’s sherpa on her journey is Erik Seidel (also in Rounders); Erik has won over $41 million (!) during his poker career.  

After a particularly bad beat in a poker tournament, Konikova is taught a similar lesson by Seidel about not focusing on results.   He tells her:

“...every player is going to want to tell you about the time their aces got cracked. Don’t be that player…Bad beats are a really bad mental habit. You don’t want to ever dwell on them. It doesn’t help you become a better player. It’s like dumping your garbage on someone else’s lawn. It just stinks” (132-133).

Seidel encourages Konikova to “focus on the process, not the luck.”   

I suspect this is why I was lousy at playing poker.    

When I played, I wanted to win the hand; I had no interest in judging whether or not I was “winning” the battle to make the best decisions.   I’m probably better off that I stopped playing poker, but often return to it when I think about whether or not I am making the best possible decisions as a leader.   

Weekly Links

1. The Theology of K-Pop: I don’t get K-Pop.  Again, I’m totally lame.   But Religion Unplugged did a deep dive into the spirituality of BTS, sometimes called the “Bangtan Boys.”  I’m still not a fan, but any band with over 67 million followers on Instagram catches my attention.

2. The Never-ending Hybrid Work Debate: I suspect that it will be years before anyone “solves” the question of whether or not people should return to the office full-time, as returning to the office involves all kinds of complications.  But that’s why you have me to summarize things (you’re welcome!).   Here is a study of 30,000 emails on the value of hybrid work, a Gallup poll on how workers feel about returning to the office, and a reminder that the previously trendy “open office” concept was a horrible idea.

3. Work Is NOT Your Life: If a typical person is alive for 4,000 weeks, the average career makes up only 12% of one’s life.   This is important to put this into perspective in the Jewish organizational world, an activist space that can lead to characteristic burnout and vicarious trauma.

4. DAFs Are For Everyone?: Donor Advised Funds (DAFs) are increasingly common tools for people of means to manage their philanthropic assets.    Here is an intriguing profile of Daffy, an attempt to disrupt the DAF from within the Jewish community.

5. Repentance BOT: My colleague and friend Rabbi Danya Ruttenberg’s newest book On Repentance and Repair is a must-read for the high holiday season, but not half as cool as the repentance bot she created.   Can machines teach us to repent better than other people?   I’m dubious, but I’m sure it will be more effective than 1-800-OOPS-Jew.

Rosh HaShanah

I am going to play around with different times of the week and different times of the day to publish the newsletter.   Given that Rosh HaShanah starts on a Sunday night, the newsletter will not be published that night.   Just wanted to give you a heads-up.

1. I tried to think of an appropriate joke that involved the episode of Seinfeld where Kramer gets addicted to Kenny Rogers’ chicken, or when Kevin from The Office leads the staff in singing “The Gambler” as they travel to the beach. Alas, inspiration escaped me.

2. Rounders begins with a quote often attributed to Amarillo Slim: “If you can’t spot the sucker in your first half-hour at the [poker] table, then you are the sucker.” I was the sucker.