The Art of Failure

I play a lot of poker. I write about poker. I also think a lot about poker. When I watch a movie, I’ll often think about some of its situations in poker terms. Isn’t that guy bluffing in a bad spot? Doesn’t he realize that his girlfriend is sure to call his bluff! Even when I am reading a book about something else, I often ponder whether some of the things the author is discussing have parallels in poker. If you have never read anything by Malcolm Gladwell, you should. His two best books are Blink and The Tipping Point. His most recent book is a collection of essays, most of which were previously published in The New Yorker magazine. He draws on modern research and thinking from a number of disciplines, including psychology, medicine, mathematics, and finance. The first part of this column is based on a distinction that he makes in an essay titled “The Art of Failure.” While he makes no mention of poker, many of his insights can explain some of the worst mistakes that players make under pressure.

Learning a new skill is a slow process. In the beginning, you carefully think through each step consciously. Soon, your unconscious thinking starts to assume command. You no longer have to think about each step of the process. An experienced driver, golfer, or poker player performs most of his tasks automatically. Gladwell distinguishes between two types of mistakes that can be made under pressure: choking and panicking. When a player chokes, he reverts to the earliest stages of learning. He tries to think through each step of the process as if he were just learning it, and this is fatal to his performance. Someone whose unconscious thinking could enable him to function on an expert level is now thinking through each step of the process like a total beginner. Gladwell cites the collapses of Jana Novotna at Wimbledon and Greg Norman at the Masters as examples. We all have seen players under pressure respond with total ineptitude. They completely fail in attempts to execute something that should be automatic for them. All-star basketball players miss everything on a key foul shot, and all-pro receivers drop wide-open passes in the end zone. We’ve all seen superstar poker players call off all of their chips in situations in which it is obvious to everyone else at the table that their opponent has the nuts.

Panicking is very different from choking. Choking is a phenomenon that paralyzes experienced players. Panic is the affliction of the inexperienced. Panic happens when you know that some important action is called for, but in your desperate search through a limited repertoire of behaviors, you can’t find the appropriate response. Gladwell cites the death of John F. Kennedy Jr. as an example of an inexperienced pilot panicking under adverse conditions.

A novice no-limit hold’em player once described the following deep-stack situation to me: She raised from early position with the A Q, and got two callers. The flop came J 10 4. She bet, and got raised. She knew that she had a crucial decision to make in what might be a big pot. She said, “I thought and thought, trying to decide if I should call or fold. I finally decided that it was right to call. The turn was the 3. So, I checked, and he went all in for a lot of chips, and I folded. I’m sure that it was right to fold, but I’m not sure that I should have called the raise on the flop.” I would consider this to be a case of “poker panic.” Her choices should have included reraising
all in herself on the flop. This was almost certainly the best play, yet she didn’t even consider it.

In a group of essays labeled “Theories, Predictions and Diagnoses,” there are two, “Open Secrets” and “Connect the Dots,” in which he discusses the failures of various intelligence-gathering services. Shouldn’t they have been able to predict the Japanese attack on Pearl Harbor, or the World Trade Center attack on 9/11? Shouldn’t the financial gurus have been able to foresee the Enron disaster? Here again, there are several parallels to poker. Much of what we do at the poker table is intelligence gathering. Why is it that we so often fail to do a good job of determining when our opponents are bluffing and when they have big hands?

Gladwell cites national security expert Gregory Treverton, who distinguishes between puzzles and mysteries. A puzzle is a problem that can’t be solved without more information. Each piece of information brings us closer to solving the puzzle. A mystery, on the other hand, is a problem that can be solved with the information that we already have. Its solution, however, requires that we correctly analyze the data that we already have. In some cases, we may have so much information that it is important to sift through it to key in on what is essential for the solution. Figuring out whether or not an opponent is bluffing is sometimes a puzzle and sometimes a mystery.

You are moved to a new table in a tournament. You flop top pair with top kicker. There are two of a suit on the board. You bet nearly the size of the pot, and an opponent you’ve never seen before makes a big raise. Is he bluffing or semibluffing? This is clearly a puzzle. You need more information to make a decision. Perhaps you can draw some inferences from his age or demeanor. Perhaps you can ask him a question, and his answer will reveal something about his hand. Now, suppose that it’s the same situation and your opponent is someone you know very well. You know that he bluffs frequently, and that this is the type of spot in which he likes to bluff. He knows that you are a conservative player who is capable of making a big laydown. But he also knows that you know him, and might be suspicious. Plus, you know that he has been running badly lately, and you are pretty sure that he really wants to finish in the money, and so on. This case is a mystery, not a puzzle. You have to search through all of the things that you know about him, and find the ones that apply to this situation. If you can align several crucial pieces of information, you will make the right decision.

In conclusion, I want to emphasize my recommendation that you read some of Gladwell’s works. He is a good writer with interesting ideas. I also want to urge you to find and think about the parallels to poker that occur in many diverse areas.

Steve “Zee” Zolotow, aka The Bald Eagle, is a successful games player. He currently devotes most of his time to poker. He can be found at many major tournaments and playing on Full Tilt, as one of its pros. When escaping from poker, he hangs out in his bars on Avenue A — Nice Guy Eddie’s at Houston and Doc Holliday’s at 9th Street — in New York City.