Our Decision-Making Process Is Broken. Math Tells Us Why.

What is the math telling you?

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I first met Rob Ristagno in 2016 at a Niche Media event. We’ve chatted a couple times on the phone since then, but I hear from Rob mostly when he responds to my newsletter.

Last week I mentioned something in Random #18 newsletter about standardized scores. Rob followed up and told me I HAD to listen to Revisionist History by Malcolm Gladwell, Season 4, Episode 1 and Episode 2, a two-part series on the failures of the LSAT test (they were mind blowing…please listen…but…if you can’t…Gladwell finds that the best lawyers in the world DO NOT go to the top 14 law schools and generally DO NOT do well on the LSAT). Mind blown.

After listening, I became hooked on Gladwell’s Podcast. I’ve devoured seasons three and four. All the episodes are good, but it was Season 3, Episode 7 where I learned to “Pull the Goalie.”

Malcolm Gladwell, author of The Tipping PointOutliers and a number of others, never had a rule for living until he read a review paper by Clifford Asness and Aaron Brown entitled “Pulling the Goalie: Hockey and Investment Implications.”

NOTE: If you made it this far and don’t know where I’m going, please hang in there. I promise it will be worth it. And yes, I did read the entire review paper.

Pulling the goalie is a hockey reference. In a 1931 hockey match, Boston Bruins coach Art Ross trailed the Montreal Canadians 1-0. With a minute to play, Ross pulled his goalie out of the game and inserted an extra attacker. The game ended without any additional goals scored, but Art Ross is given credit for the aggressive coaching move. Today, the move is used all the time, but generally with just a minute or less left in a match.

Well, Asness and Brown did the math on the maneuver. They found that pulling the goalie was indeed the proper move, but coaches weren’t nearly aggressive enough. They found that, in actuality, if a team is down by one goal, the coach should pull the goalie at the six minute mark. If a team is down by two, it should be the 11 minute mark.

Crazy? Perhaps. Pulling the goalie increases the odds that the other team could score by four times! But (and this is a big but) the team only loses a little when the other team scores. They were already losing. Losing by two or three or four is still a loss. So, not much lost.

But at the same time, we’ve almost doubled our chance of scoring because of the extra attacker. The math says it’s the right decision. The math says that hockey coaches are way too conservative.

The paper goes into detail about why this is. Their findings?

“First, coaches are not actually rewarded for winning. They are rewarded for being perceived as good coaches. Obviously, the two are closely related but not exactly the same thing. If a basketball coach gets his team to execute crisp offensive plays with few turnovers that lead to two point baskets on 50% of possessions, he’s deemed an excellent coach. If his team still loses 100 – 102, well, his players just weren’t quite good enough. If the same coach encourages his team to “run and gun” threes, with lots of turnovers and misses, but scoring on 35% of possessions, he’s clearly lost control of his team. If they win 105 – 102 it’s perceived as just luck as everyone knows three point shots are risky. Essentially winning ugly is undervalued versus losing elegantly; and losing ugly can be career suicide.

The second reason coaches shy away from actions with short-term risk is that sins of commission are far more obvious than sins of omission.”

Math (the correct decision) takes a back seat to how our actions look…how others perceive them.

Please just pause here for a second to take all this in. Breathe in and out a few times.


This is exactly the reason we fail to reach our goals.

We keep the goalie in the net for extra defense. For safety. Because, according to the people you hang out with, it’s the right thing to do.

Take the job with benefits. Select the college major that could get you a job versus something you truly love. Never launch the business because people will call you crazy.

We are making decisions based on what we think will be socially acceptable or offer the least amount of risk. This is bad math.

I left an executive media position in 2007. It was a great job. I was making six figures. Had benefits. When I left that job to start a business, you can imagine the scrutiny. My friends and family thought I was crazy. They thought I was risking so much. And they said this to my face. I can only imagine what they said when I wasn’t around.

My belief was (and still is) that there is way more risk working for a company. Where you don’t have control over what the company does. Or how and when they give out benefits. Working for someone else almost always puts a cap on your earning potential and overall freedom.

So, I did the math. The math said leave, while every “sensible” person said stay.

By the way, if you don’t know my story, the math worked out really, really well for me.

What is the math telling you? Is it about a job? About your significant other? About where and how you live? About the creative project you will or won’t do? About what you will and won’t say to your boss?

The worst case? People will think you are crazy. People may look down on you. They may talk about you behind your back.

The best case? You fulfill every single one of your dreams. You win and keep winning until you’ve won everything.

The risks you think are the riskiest aren’t really risky (say that five times). The safe bets are the riskiest of all.

Time to pull the goalie.

And finally, back to Gladwell. If you’d like to know why you do or don’t make the right decisions, listen to “The Big Man Can’t Shoot,” which is Season 1, Episode 3 of Revisionist History. This will be the best 30 minutes of your day.


A portion of this article previously ran in Joe Pulizzi’s Random Newsletter. Joe is the author of The Will to Die, his debut novel.

Originally published on

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