13 Habits of Highly Effective Risk-Takers

I played poker professionally before I wrote about politics or built an electoral model. What really fascinates me about the game is the mindset that drives this behavior – a way of thinking that unites a cohort I call “the River”.

The river is a sprawling ecosystem of like-minded people that includes everyone from low-stakes poker pros to cryptic kings and billionaire VCs. It is a way of thinking – analytical, abstract, competitive, contrarian – and a way of life. Most “Riverians” are not rich and powerful, but rich and powerful people are disproportionately likely to be Riverians.

I call the following “13 Habits of Highly Effective Risk-Takers.” Quantitative risk takers and physical risk takers—astronauts, sea explorers, NFL players—have these characteristics in common. Based on my research, I hold the opinion that there is something hardwired in people who seek risk and encounter it successfully. How much do you share with them?

Successful Risk-Takers are Cool Under Pressure

Being calm when others are losing their shit is a rare quality – and one that is essential to a winning player. No matter how well you perform in everyday situations – you will never reach the top of your craft if you choke when the pressure is on.

They have courage

In poker and sports betting, most players lose money. To be on top requires a careful balance. Overconfidence can be deadly in the game, but playing poker against the best is not for the faint of heart.

They have Strategic Empathy

They put themselves in their opponent’s shoes, but don’t mistake this for the touchy-feely kind of empathy. In psychological studies, there is a negative correlation between systematic thinking – what the Riverians are qualified – and empathic behavior. Strategic empathy comes up a lot in poker, which is very much a math game and a people game.

They are process oriented, not results oriented

They play the long game. “Don’t be results oriented” is a mantra ingrained in many poker players. Yes, in the long run, results are what count, but one good thing about River is that our compensation ultimately depends on objective measures.

They take hits

They are explicitly aware of the risks they are taking – and they are comfortable with failure. In an episode of the American version of The Officethe head imbecile, Michael Scott, misappropriates a quote from hockey player Wayne Gretzky: “I miss 100% of the shots you don’t take.” There is something to be said for that.

They have a Raise-or-Fold attitude

They hate mediocrity, and they know when to quit. The cardinal sin of poker is that most players hold them too often. There are three basic actions in poker: call, fold, raise. People press the call button too. They call because they want to play, but even though the players call when they are going to fold, they also call when they are going to be raised.

They are Prepared

They make good intuitive decisions because they are well trained, not because they “wing it”. What attracted the private equity investor and explorer Victor Vescovo Top Gun: Maverick it was Tom Cruise’s insistence that you should improvise your way out of a hairy situation: “The best military operations are the ones that are very boring, where things go exactly according to plan. Nobody ever put themselves in danger,” he said. “You want to minimize the risks. While Top Gun It looked great on film, that’s not how you try to take that goal away.”

They have great attention to detail

They understand that attention is a scarce resource. In poker, one of the unusual features of the game is that most of the time, you have nothing to do, exactly – there is a lot of waiting. You need to properly calibrate your mental bandwidth, conserve energy, but be prepared to take action.

They are Adaptable

They are good generalists, taking advantage of new opportunities and responding to new threats. I call this personality type Fox. Think of the Greek poet Archilochus who said: “The fox knows many things, but the hedgehog knows one great thing.” Foxes look for opportunities, beware of complacency and get too attached. This is a habit to which there are some exceptions. In particular, startup founders need to be laser-focused on one big thing and be prepared to see it out for a decade or more.

They are good estimators

They are Bayesians, comfortable quantifying their intuitions and working with incomplete information. Does the difference between 90% and 93% really matter?

Try to stand out, not fit

Independence of mind and purpose are hallmarks of high achievement.

They are Wise Contrarians

They have theories about why and when conventional wisdom is wrong. There is a distinction between independence and the opposite. If I pick vanilla and you pick chocolate because you like chocolate better, you are independent. If you choose chocolate because I took vanilla, you are against it. Riverians can be accused of being contrary when they are really independent. If I do the conventional thing 99 percent of the time, and you do it 85 percent of the time, you’ll look like a rebel by comparison – but really you’re still going with the flow.

They are not driven by money

They are not ascetics, but poker players are distinguished for two reasons. First, they are so fiercely competitive that money serves mostly as a way to keep score; and secondly, playing for such high stakes requires some desensitization to them.

Adapted from On the Edge: The Art of Risking Everything, by Nate Silver.