Can Bad Odds Make You More Likely to Succeed?

“Do not pray for an easy life. Pray for the strength to endure a difficult one.” —Bruce Lee

At one point in the American Civil War, General Ulysses S. Grant needed to capture the city of Vicksburg, Miss., a cliffside city overlooking the Mississippi River that the Confederate Army used to prevent Union troops and supplies from floating south. Grant tried everything: He tried marching around; he blew up dams upstream to flood the area; he dug canals to re-channel the river and avoid the guns at Vicksburg. Nothing worked.

As a last resort, Grant did something crazy. He floated downstream, past the Confederate gun batteries, then marched up to Vicksburg to begin a ground siege from the south. To make it safely, Grant’s men had to travel without supplies. It was a one-way trip. By the time they reached Vickburg, the troops were so determined and so desperate—with no food and no option for retreat—that their attack surprised and overwhelmed the confident Confederate troops into surrender.

Grant is one of many bold figures that bestselling author and business strategist Ryan Holiday profiles in his new book, The Obstacle Is the Way: The Timeless Art of Turning Trials Into Triumph, released this week. Obstacle is a 21st century handbook on Stoicism, an ancient Greek philosophy for overcoming destructive emotions, made particularly famous by the Roman emperor Marcus Aurelius.

In the book, Holiday argues that obstacles in work and life aren’t speed bumps on the road to success; they create success. Ulysses S. Grant, he says, wasn’t a great general because he was blessed with opportunities to learn and climb through ranks and fight easy battles; Grant became great because everything he had to do was incredibly hard. And his men succeeded because he made them face problems head-on, rather than retreat or resort to tricks.

I’ve always personally had beef with the saying, “What doesn’t kill you makes you stronger.” (A stroke that doesn’t kill you rarely makes you stronger, at least physically. Research from Harvard University shows that entrepreneurs who fail in one business are not really more likely to succeed in a second business, when you adjust the stats for margin of error.) But Stoicism suggests a rather empowering alternate view: “What doesn’t kill you can make you stronger, if you follow the right framework.”

This idea has been supported in my own business experience by the observation that my biggest role models have endured the most brutal trials. In the early 2000s, NextJump CEO Charlie Kim (whom I’ve written about before), had to lay off 150 people during the dot-com crash, bringing his company headcount down to four. Over the next decade, he built the company back up to 200+ employees and a work environment that any business owner would envy. His employee retention is nearly 100 percent, and his customers and employees love his company more than any company should be loved. Other excellent examples of this can be found in Ben Horowitz’s recent book, The Hard Thing About Hard Things, which with painful candor documents the misery of running a startup and shows how those setbacks help build great businesses. Horowitz’s story will make you not want to complain about your job again.

New Yorker writer Malcolm Gladwell adds color to this concept in his latest bestseller, David and Goliathin which he explores the nuances between disadvantages in life that lead to greater success and disadvantages that set us back. Gladwell writes about a theory of return on effort called the “inverted U”, which, for example, explains how disorders like dyslexia lead certain people to work harder in ways that help them become great entrepreneurs—but says that at a certain point the benefits of such things cease. (E.g., developmental disorders can reach a severity where they start to make business success near impossible.) The point is that although challenges and obstacles in life and work—setbacks, bad bosses, personal failures—can make us stronger, past a certain point, hardship just does damage. There’s a zone where difficulties propel us to huge personal growth over those with an easy path:

Holiday argues that if we want to become better workers, we should deliberately and stoically ride out conflict, instead of seeking to avoid it.

That’s easier said than done. But a study of Stoics like Aurelius and Grant indicates that the threshold for what will make us stronger without killing us is surprisingly high.

“Stoicism is a framework that makes us particularly resilient and adapt for all types of problems whether it’s a co-worker or an economic collapse, a war, or car trouble,” Holiday says. “The Stoics saw every obstacle, every situation as a kind of fuel.”

The Odds Don’t Matter—We Only Make Them Matter

Science has shown that we humans have a tendency to make life harder because we think things are going to be hard.

In 2009, behavioral psychologists Stephen M. Garcia and Avishalom Tor ran a series of experiments in which they had students take competitive academic tests in various group settings. They discovered that the smaller the groups of students taking a test, the better students performed (the harder they tried). A student in a room with 10 other test takers would on average score higher than the same caliber student in a room of 100 students—because the odds of being the best were higher. But at a certain point, the inverted U happened: More test takers stopped mattering (1,000 versus 2,000 competing students didn’t make a test taker feel more or less hopeful about her odds of coming out on top). According to this and subsequent research on competitive performance, our human nature makes us try less hard at things when our odds are worse.

Those students weren’t taking more difficult tests. They just subconsciously lost a little hope. Holiday argues that merely thinking about the obstacles in front of us in an objective way (the test isn’t any different just because there are more people) helps us beat the average when others subconsciously give up. The trouble is that we tend to approach problems with our hearts and not our heads. Our hearts are better used for motivating and relating and inspiring and loving other people, he argues, but are best left out of problem-solving.

A Stoic Framework

In 1864, Ulysses S. Grant fought a series of battles against Robert E. Lee in Virginia, known as the Overland Campaign. One day during this campaign, General Grant was surveying the battlefield through field glasses when a Confederate shell exploded next to him, killing a horse a few feet away. Grant didn’t even flinch.

On another occasion, a steamboat in the James River exploded near Grant and his men on the shore. As Holiday writes in Obstacle, “Everyone hit the dirt, except Grant, who was seen running toward the scene of the explosion as debris and shells and even bodies rained down.”

How did Grant develop this cool under such terrifying circumstances? Through a lifetime of practice shelving emotion during “problem-solving time.” When the bombs rained down on him, Grant was able to turn his heart off, so to speak, and use only his head.

“What’s so wonderful about Stoicism is that the actual people who used it have passed along their records,” Holiday says. “From Marcus Aurelius, the most powerful man in the world in his time, we have his personal thoughts and reminders. From Epictetus, a former slave, we have the actual lecture notes from one of his students. From Seneca, one of the most successful business men and advisors in Rome, we have the letters he wrote his friends. We can study from them—see them face the same problems we face—and apply the same logic, the same framework, the same operating system and watch it dissolve our own obstacles.”

Holiday breaks Marcus Aurelius’s teachings—which have been remarkably preserved over the millennia—into three overarching Stoic steps: perception, action, and will. At the heart of Stoicism is the idea of changing the way we see challenges. Next, Stoics take deliberate action (or deliberately take no action). And, finally, they persevere and gather support and eventually excel through sheer force of will.

These seem like obvious ideas, but when broken down into the small, practicable mental disciplines like recognizing your power, steadying your nerves, channelling energy, contemplating mortality, and more, a surprisingly nuanced and difficult roadmap unfolds—a roadmap that clearly takes time to master, but appears altogether worth it.

Obstacles Provide A Choice

“Everything that happens to us provides us with a choice: Are we going to face this and get better because of it? Or are we going to allow this to derail and frustrate us?” Holiday says. “Most people don’t tend to see obstacles this way.”

Facing down hard things like the great Stoics in Holiday’s book doesn’t increase our odds of good luck, per se. “What Stoicism says is that we don’t control what happens to us; we control how we respond—even if that response is just endurance, or acceptance or humility,” Holiday says. “We always have this choice.”

Holiday is hoping to bring Stoic philosophy to modern business culture. Could such mental discipline lead to fewer knee-jerk reactions in public markets and social media, and more thoughtful entrepreneurship in the Valley and on Wall Street? Twenty-three hundred years of history suggest it might.

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