Why You’re Not Taking Enough Risks


The third season of Malcolm Gladwell’s brilliant podcast has an episode titled Malcolm Gladwell’s 12 Rules for LifeExcept, we find out a few minutes in, Gladwell doesn’t have 12 bites of wisdom to share, and he even feared he didn’t have any rules for living.

Luckily (for both him and us), he changed his mind after talking to his mathematician friends Clifford Asness and Aaron Brown from NYU.

Gladwell has one principle:

Pull the goalie.

Now, What the Hell Does That Mean?

In hockey, teams may “pull their goalie” and get a sixth attacker in return.Playing with an open goal sounds rather inconvenient, but consider that the losing side gains a lot by scoring, while suffering little if their opponents get one in. Defeat by two goals is no worse than defeat by one.

We happen to live in an awesome world where I can eat Oreo cookies and brilliant number-nerds-who-are-also-hockey-freaks like Asness and Brown can unleash their mathematical abracadabra to take a crack at a related risk-management puzzle just for fun:

What is the turning point, in terms of time left, at which the losing team’s chances of scoring in the few remaining moments, have gotten so low that swapping the goalie gives them a better chance at a result (despite the risks involved), than continuing with five attackers?

Have a cookie while you read the query again.

Failing to Maximize Your Chances of Winning

While there are no rules that forbid this particular substitution earlier in the game, it’s common to wait until there’s one minute or so left to play before resorting to this all-or-nothing move.

Now, using different models and data, all calculations agree goalies should be pulled much earlier than they usually are.

For example, when you’re one goal down, Asness and Brown conclude teams will get the maximum advantage if they pull the goalie with six minutes and 10 seconds left in the game.

Here’s what that means. Assuming both teams are equal and one of them went up 1–0, the odds of the team that’s behind coming back get lower and lower as time goes on. The math has come up with 6:10 minutes as the threshold where the losing team’s chances of tying have gotten so low that pulling the goalie is now their best chance at winning.

If you pull later, you’re shooting yourself in the foot. You’re failing to maximize your chances of getting a result.

Yet, of course, nobody does it that early. It would be weird. The other team would think you went mad.

Using analogous reasoning, when you’re two behind, you ought to pull the goalie with 13 minutes to go. (The bigger the goal difference, the stronger the “safe is death” logic of pulling the goalie is.)

Any hockey coaches who are reading this may be thinking, are you kidding me? Pulling less than halfway through the third period, you must be out of your damn mind. I don’t care about maximizing my chances of winning! It’s just way too early! Unheard of! Not done! No, I don’t want another cookie! I want to keep my job!

Do This if You Don’t Want to Achieve Your Goals

Knee-jerk reactions aside, why do coaches fail to act when it would be best to pull the goalie? After all, their decision-making now actively harms their team’s chances of success.

Asness and Brown offer two explanations.

Their main incentive? Avoiding blame

The first reason: coaches are not actually rewarded for winning. They’rerewarded for being perceived as good coaches.

You may be thinking, “Everybody understands that the coach should try to win the game, not a popularity contest. If his choices reveal he’s optimizing his chances for the latter, not the former, he’s stupid.”

This misunderstands the point entirely.

His incentives are geared toward doing the normal, not toward doing the optimal. He is simply acting in line with those incentives.

People often care primarily about doing that which no one could blame them for.

Blame does happen, and the real incentive is big already. Being ridiculed feels shitty. We have a primal fear of doing anything weird that blows worries of social disapproval way out of proportion. In our heads, it’s the end of the world. Hence something possibly being slightly unusual acts as a veto.

Keeping up appearances

The second reason coaches shy away from actions with short-term risk is that sins of commission (versus the norm) are far more obvious than sins of omission (versus the norm). From the Asness & Brown paper:

“The hockey coach who pulls his goalie down 0–2 with ten minutes to go and loses 0–5 will face harsh criticism from every quarter. A coach who quietly loses 1–2, pulling his goalie only in the final minute, can hold his head up and say his guys played hard but the puck didn’t roll their way tonight; it was a close game, and they’ll work even harder to get the breaks tomorrow (giving 110% of course).”

People will blame you if you try something new and it goes wrong. They won’t blame you if you try conventional wisdom and it goes wrong.

People Care More About Taking the Socially Appropriate Steps Than About Solving the Issue

To sum up: pulling the goalie is traditionallydone with only a few seconds left. Doing it at any other time is considered to be stupid. Since coaches are rewarded for being perceived as good coaches, they make calls serving thatgoal rather than doing everything they can to win.

Some decisions that coaches make are mathematically indefensible, but they make sense when considering the coach’s motivations.

This not to bash on hockey trainers. It applies to everyone.

Often, people don’t care much about maximizing the chance of achieving their goal.

They care about whether they’re responsible.

They care about whether socially appropriate steps have been taken.

With this in mind, let’s look at Malcolm Gladwell’s number one rule for life.


When you gather a trunk of data related to personality, you find that people vary on five different scales (social scientists call this the Five-Factor Model). (Dis)agreeableness is one of these dimensions. Psychologists define being disagreeable, in turn, as the quality of not being dependent on, or particularly interested in, the opinions of others.

To get a sense of what this means in real life, imagine you’re the coach of a hockey team. You’re down three to one with 13 minutes left. You pull your goalie earlier than anyone ever has before in the sport’s entire history.

The other team scores.


It’s four to one with half of the final period left, and now your fans think that you’ve robbed them of what might have been an interesting game.They’ll hate you. And so will your players — it’s more humiliating to lose a lopsided game than a close one.

In the podcast, Gladwell asks and answers:

“Who would try this? Not anyone who has any normal human expectation of being liked and applauded.”

It’s not that pulling the goalie with 13 minutes left is idiotic. It’s that pulling the goalie with 13 minutes left in the game looks idiotic, and you don’t want to appear idiotic, so you don’t pull the goalie. Doing anything other than pulling the goalie in the final seconds would be impossibly disagreeable.

In other words, anyone who cares too much about the opinions of others is likely to choose the strategy that is most likely to lead to being perceived as doing the normal thing.They’ll do this atthe expense of actually getting what they really want.

You’re not taking enough risks because you don’t want to look stupid. You’re not doing what you should do because you’re not willing to disagree.

Can We Become More Disagreeable?

Oh, isn’t this fun, pointing out how dumb some things are? How misguided incentives can lead to systemic incompetence? To an equilibrium of everyoneacting insane that’s secretly a sane response to everyone else acting insane?

What if you wanted to defy the system, stop being a slave to the social norms, and also actually maximize your chances of winning?

I care about the opinions of others. I’m interested in the approval of my fellow human beings. So shoot me.

If you, like me, are an agreeable-natured person, it might take some courage to reverse the order of these priorities. Because here’s the crux:disagreeableness is a matter of choice, not of temperament.

Perhaps you can’t stop fearing rejection, getting these anxieties, having these thoughts. You can, however, block them from contaminating your decision-making process.

How, you want to know?

Ask the right questions.

Asking the Wrong Question

The question we’re answering when drawing our battle plans is too often, “What gives me the highest percentage chance of winning without also giving me a chance of looking stupid?” It should just be: “What gives me the highest percentage chance of winning?

Instead of maximizing the probability of success, we’re maximizing theconditional probability of a successful outcome given that the strategy involved can only lead to socially acceptable outcomes.

Not losing face takes priority over achieving your goal. It’s only when you want, above all else, to actually win the game — without also winning the popularity contest and without consolation prizes just for trying — that you will actually put in the effort to actually maximize the probability of success.

The Takeaway: Maximize Your Chances of Winning

The core question behind Gladwell’s number one rule for life is: how much will you let what others think of you get in the way of doing what you should do?

People make the choices they do because they think these choices are the ones they can’t be blamed for.We’d rather minimize our chances of being blamed than maximize our chances of winning.(Doing the normal — pulling the goalie with a second to go — means no one could blame you.)

Gladwell advises us to do the exact opposite.

Maximize your chances of achieving your goals. Even if doing so means you might not be perceived as a good coach or as having taken the socially appropriate steps. Hell, you might even be blamed for not doing the normal thing.

Ask the right question, ignore potential social costs, and execute the plan most likely to lead to success.

Pull the goalie.

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