1: The year was 1863. General Ulysses S. Grant was stuck.

For a year, he and his troops had tried to crack the defenses of Vicksburg. The city sat high on the cliffs of the Mississippi, providing a “stranglehold on the most important river in the country,” writes Ryan Holiday in The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph.

Ulysses had attacked Vicksburg head-on. Failure.  

He tried to go around it. Failure.

“He spent months digging a new canal,” writes Ryan, “that would change the course of the river.” Failure.  

“He blew the levees upstream,” he notes, “and literally tried to float boats down into the city over flooded land.” Failure.

The situation appeared grim. “All the while, the newspapers chattered. It’d been months without progress,” Ryan writes. “Lincoln had sent a replacement, and the man was waiting in the wings.  

“But Grant refused to be rattled, refused to rush or cease. He knew there was a weak spot somewhere. He’d find it or he’d make one,” Ryan writes.

2: Which is what he did. Ulysses next decided to move his boats past the Confederate gun batteries protecting the river—”a considerable risk, because once down, they could not come back up.”

A fierce nighttime battle ensued. When the sun came up, almost all Union boats had successfully made the run. Several days later, Ulysses and his army crossed the Mississippi thirty miles downstream “at the appropriately named Hard Times, Louisiana,” notes Ryan.  

His plan was bold: “Leaving most of their supplies behind, his troops had to live off the land and make their way up the river, taking town after town along the way.”

The message was clear to all: Ulysses would never give up. He was confident that somehow, someway, the defenses would eventually break. However long it took, he was determined to prevail.  

This mindset makes all the difference. “If we’re to overcome our obstacles, this is the message to broadcast—internally and externally,” writes Ryan. “We will not be stopped by failure, we will not be rushed or distracted by external noise. We will chisel and peg away at the obstacle until it is gone. Resistance is futile.”

During the battle of Vicksburg, Ulysses learned two things, Ryan writes. “First, persistence and pertinacity were incredible assets and probably his main assets as a leader.  

“Second, in exhausting all the other traditional options, he’d been forced to try something new,” Ryan observes, “In persistence, he’d not only broken through: In trying it all the wrong ways, Grant discovered a totally new way–the way that would eventually win the war.”

When we encounter obstacles and challenges, we can think of Ulysses. A cigar gripped in his mouth. “The thing standing in our way isn’t going anywhere,” Ryan surmises. We are “not going to out-think it or out-create it with some world-changing epiphany.” Instead, we have to “look at it and the people around us, who have begun their inevitable chorus of doubts and excuses, and say, as Margaret Thatcher famously did: ‘You turn if you want to. The lady’s not turning.'”

3: We think great victories like Ulysses ultimately won at Vicksburg come from a flash of insight or genius. “In fact, it was the slow pressure, repeated from many different angles, the elimination of so many other more promising options, that slowly and surely churned the solution to the top of the pile,” writes Ryan.  

“For most of what we attempt in life, chops are not the issue. We’re usually skilled and knowledgeable and capable enough. But do we have the patience to refine our idea? The energy to beat on enough doors until we find investors or supporters? The persistence to slog through the politics and drama of working with a group?”

“Persist and resist,” wrote the Stoic philosopher Epictetus: “Persist in our efforts. Resist giving in to distraction, discouragement, or disorder,” Ryan writes.  

No need to get upset. No need to despair. We’re not going anywhere. We’re not going to be counted out. We are in this for the long haul. “Never in a hurry, never worried, never desperate, never stopping short,” Ryan suggests.

What is persistence? It’s deciding: once we begin attacking an obstacle, “quitting is not an option. It cannot enter our head. Abandoning one path for another that might be more promising? Sure, but that’s a far cry from giving up,” writes Ryan.

“Temporary setbacks aren’t discouraging. They are just bumps along a long road that we intend to travel all the way down.”

Because when we do anything new, we can count on obstacles. “A new path is, by definition, uncleared,” writes Ryan. “Only with persistence and time can we cut away debris and remove impediments. Only in struggling with the impediments that made others quit can we find ourselves on untrodden territory—only by persisting and resisting can we learn what others were too impatient to be taught.”

More tomorrow!


Reflection: Think back on a time when I overcame many obstacles on my way to achieving a meaningful goal. What was it that allowed me to persist?

Action: Discuss with a friend or colleague.

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