The Battle of Long Island was a disaster for George Washington’s army. His 10,000 troops were crushed by the British and its 400-ship fleet.
But it could have been so much worse. It could have been the end of the Revolutionary War.
All the British had to do was sail up the East River and Washington’s cornered troops would have been wiped out, with Washington captured and executed for treason. That was their plan.
But it never happened, because the wind wasn’t blowing in the right direction.
Historian David McCullough once explained to Charlie Rose:
McCullough: If the wind had been in the other direction on the night of August 28th, I think it would have all been over.
Rose: No United States of America if that had happened.
McCullough: I don’t think so.
Rose: Just because of the wind, history was changed.
We know one version of history – the version that actually happened – but there are infinite alternative versions that were just as likely to come true.
Read enough of these freak events that changed everything and you become less willing to make big predictions.
Early in his career Andrew Carnegie took a train to deliver a bundle of payroll checks to his crew. Riding on an open deck, a bump caused the checks to fly out of his pocket, landing near a river. The train pushed on. The checks were lost.
Carnegie knew this was catastrophic. If unpaid crews quit, you’re finished. “There was no use in disguising the fact that such a failure would ruin me,” he wrote in his autobiography.
At the final destination Carnegie convinced the engineer to drive the train in reverse back to the spot where his checks flew out. He wrote:
I watched the line, and on the very banks of a large stream, within a few feet of the water, I saw that package lying. I could scarcely believe my eyes. I ran down and grasped it. It was all right. The engineer and fireman were the only persons who knew of my carelessness, and I had their assurance that it would not be told.
To Carnegie, the lesson wasn’t tenacity or persuasion or anything like that. It was empathy. He wrote:
I have never since believed in being too hard on a young man, even if he does commit a dreadful mistake or two; and I have always tried in judging such to remember the difference it would have made in my own career but for an accident which restored to me that lost package at the edge of the stream.
Every successful person has a similar story and should heed a similar takeaway.
One of the funniest scenes from Seinfeld is Jerry at the dentist. Before putting the nitrous oxide mask on his patient, the dentist takes a hit of the gas himself and declares, “Yep, it’s good.”
The whole scene was an accident; in the original script Jerry was just supposed to take the gas and pass out. Bryan Cranston, who plays the dentist, later revealed where the joke came from:
As we’re rehearsing I hear someone say, “Hey, you know what would be funny?” And I look around the set and I see a guy adjusting a light. And I said, “What?” And he goes, “It’d be funny if before you gave it to Jerry, you took a hit yourself.”
And I went, “Oh my god, that is funny.”
We had to do that scene about 12 times [because Jerry was laughing so hard.]
Cranston’s takeaway is great:
I think a very smart CEO of any company, big or small, has a policy where they listen to every suggestion and idea — best idea wins. That’s how it should be. Best idea wins. And you never know where it’s gonna come from.
Related: I often wonder how many tens of billions of dollars have been paid to management consultants to solve problems that low-wage line workers had solutions for.
After years of tests, Lockheed engineers finally built a stealth plane. They could fly their prototype without radar picking it up. It was a miracle.
Then one day, it just stopped working.
“You lit up the radar like a goddamn Christmas tree” an engineer tells a test pilot in the book Skunkworks. “They saw him coming from 50 miles away.”
No one could figure it out. They hadn’t made any changes to the plane’s design.
The cause, they eventually discovered, highlighted the complexity of their work.
A screw hadn’t been secured tightly enough during maintenance, its head extending a few millimeters above the plane’s surface. That was maybe half a drill spin less than ideal. It was more than tight enough for the plane to operate. But on radar, it “appeared as big as a barn door.”
There’s a lot of hidden leverage in the world – tiny things that seem inconsequential but operate in a tightly wound system where one flaw can bring everything down.
It also makes me wonder: How much incredible technology has been abandoned in frustration when we were half a drill spin away from success?
Skateboarder Tony Hawk landed a 900 – two and a half spins – at the 1999 X Games. It was the biggest achievement the sport had ever seen, the equivalent of the four-minute mile.
It catapulted Hawk into legend status. His video game came out a year later and sold 30 million copies. Six Flags named a rollercoaster after him.
But here’s the craziest part of this story: fifteen years later, an eight-year-old landed a 900.
Hawk was also the first person to land a 720 (two spins) – a feat later accomplished by a second-grader.
A lot of sports work like that. One person raises the bar over what previously seemed impossible, and that becomes the baseline for a new generation to build upon.
Just qualifying for the Boston Marathon requires a time that, 100 years ago, would put you within nine minutes of a world record.
A gold-medal gymnast 70 years ago would not make the cut in a local competition today.
Same with technology, business, and investment knowledge. One generation builds on the impossible feats of the previous one. It’s like compound interest.
A fifth-grader recently landed a 1080 – three spins, unthinkable in Hawk’s day. Asked what he thought of the achievement, Hawk replied: “It represents everything I love about skateboarding: constant evolution.”
Which is a statement you can apply to just about any field.
Robert McNamara saw the world as a giant math problem.
Henry Ford II hired him to turn Ford Motor around. He needed a “whiz kid” – that’s what Ford called it – who saw running a business as an operations science, driven by the ice-cold truth of statistics.
McNamara took that skill to Washington when he became Secretary of Defense.
Ken Burns’ documentary on the Vietnam War describes its:
Robert McNamara demanded that everything be quantified. Commanders dutifully complied. He and his staff generated mountains of daily, weekly, monthly, and quarterly data on hundreds of separate indicators – far more data than could ever be adequately analyzed.
But the strategy that worked at Ford had a flaw during war.
Rufus Phillips, a former CIA officer, once described how McNamara’s management strategy backfired during Vietnam:
McNamara decided that he would draw a chart to determine whether we were winning or not.
He was using things like the numbers of weapons recovered, numbers of Viet Cong killed, numbers of Viet Cong defectors. Very statistical.
He asked Edward Lansdale, head of special operations at the Pentagon, to come down.
He said, “Look at this [data].”
Lansdale looked, and he said, “There’s something missing here.”
McNamara said, “What?”
Landsdale said, “The feelings of the Vietnamese people.”
You couldn’t reduce that to a statistic.
Some things are immeasurably important, impossible to quantify. But they can make all the difference in the world, often because their lack of quantification causes people to discount their relevance, or even deny their existence.
David Cassidy seemed to have the best life you could imagine. A teenage heartthrob who sold out arenas and was so popular his shows turned into stampede risks.
From the outside it looked like as interesting and lucky a life anyone could hope for. Everyone loved him. He was rich. On top of the world.
But after he died in 2017 Cassidy’s daughter revealed that his last words were, “So much wasted time.”
It’s never as good as it looks.
Artist Damien Hirst once said in an interview:
I’d always made more money the next year than the year before. But it was unsustainable and it bites your arse.
They all love you. The bank loves you, and the accountants love you, because they’re taking your money. Every year you get more and more people as well. One guy is taking 10 percent and then it’s another guy taking 10 percent and another guy taking 10 percent and it’s all a big party.
But before you know it, suddenly you’ve got an overdraft when before you had loads of cash. The people who give you the overdraft are your best mates as well, smiling at you and telling you that you’re amazing so you keep doing it.
A century earlier, Andrew Carnegie was asked for money advice and said: “Even a fool can make a million dollars. But it takes a sage to keep it. Do you hear me?” He knew from experience.