1: What do Marcus Aurelius, Cato, Seneca, Thomas Jefferson, James Stockdale, Epictetus, Theodore Roosevelt, and George Washington have in common?  

“They explicitly practiced and studied Stoicism,” writes Ryan Holiday in The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph. “We know this for a fact.” 

What exactly does it mean to be a stoic?

Philosopher and writer Nassim Nicholas Taleb defines a Stoic as someone who “transforms fear into prudence, pain into information, mistakes into initiation and desire into undertaking.”

It is a philosophy and a mindset that has remained relevant for centuries.

“Frederick the Great was said to ride with the works of the Stoics in his saddlebags because they could, in his words, ‘sustain you in misfortune.’ Montaigne, the politician and essayist, had a line from Epictetus carved into the beam above the study in which he spent most of his time. George Washington was introduced to Stoicism by his neighbors at age seventeen, then he put on a play about Cato to inspire his men in that dark winter at Valley Forge.”

It doesn’t stop here. 

“When Thomas Jefferson died, he had a copy of Seneca on his nightstand,” Ryan writes. “The economist Adam Smith’s theories on the interconnectedness of the world—capitalism—were significantly influenced by the Stoicism he’d studied as a schoolboy under a teacher who’d translated the works of Marcus Aurelius. 

“Eugène Delacroix, the renowned French Romantic artist (known best for his painting Liberty Leading the People), was an ardent Stoic, referring to it as his “consoling religion.” Toussaint Louverture, himself a former slave who challenged an emperor, read and was deeply influenced by the works of Epictetus. The political thinker John Stuart Mill wrote of Marcus Aurelius and Stoicism in his famous treatise On Liberty, calling it ‘the highest ethical product of the ancient mind.’ 

“Theodore Roosevelt, after his presidency, spent eight months exploring (and nearly dying in) the unknown jungles of the Amazon, and of the eight books he brought on the journey, two were Marcus Aurelius’s Meditations and Epictetus’s Enchiridion.”

2: We, too, can choose to join these impressive ranks. We, too, can choose to become a Stoic.

But we aren’t “philosophers,” we think. But neither were most of these men and women.  

They were people of action. 

“Philosophy was never what happened in the classroom,” Ryan writes. “It was a set of lessons from the battlefield of life. Not something we read once and put up on a shelf. It was meant, as Marcus once wrote, to make us boxers instead of fencers—to wield our weaponry, we simply need to close our fists.”

Because “the great law of nature is that it never stops,” Ryan notes. “There is no end. Just when we think we’ve successfully navigated one obstacle, another emerges.”

The key? We must keep everything in perspective. “Passing one obstacle simply says we’re worthy of more,” he writes.  

“Behind mountains are more mountains,” the Haitian proverb reads.

Or, as Ryan puts it: “One does not overcome an obstacle to enter the land of no obstacles.”

3: In fact, it’s the reverse. The more we achieve, the more challenges will arise. “There are always more obstacles, bigger challenges. We’re always fighting uphill. Get used to it and train accordingly,” he writes.

We intentionally conserve our energy. We know that each battle is only one of many. We flip each obstacle by learning and improving.  

“Improving in spite of them, because of them,” Ryan writes.  

This is what it means to get better at getting better.

“Life is a process of breaking through these impediments—a series of fortified lines that we must break through,” he writes. “Each time, we’ll learn something. Each time, we’ll develop strength, wisdom, and perspective. Each time, a little more of the competition falls away. 

“Until all that is left is us: the best version of us.”

More tomorrow!


Reflection: Am I a stoic?

Action: Journal about it.

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