1: “There was little evidence that Demosthenes was destined to become the greatest orator of Athens, let alone all of history,” Ryan Holiday writes in The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph.

The boy was born weak and feeble with a severe speech impediment. His father died when he was seven.  

And then things got worse.

“The large inheritance left to him—intended to pay for tutors and the best schools—was stolen by the guardians entrusted to protect him,” writes Ryan

2: Yet, as a child, Demosthenes witnessed a great orator speaking at the court in Athens. “This lone individual, so skilled and powerful, had held the admiration of the crowd, who hung on his every word for hours—subduing all opposition with no more than the sound of his voice and the strength of his ideas.”

The image of this orator stuck in Demosthenes’s mind. He decided one day this would be him.  

“To conquer his speech impediment, he devised his own strange exercises,” notes Ryan.

“He would fill his mouth with pebbles and practice speaking. He rehearsed full speeches into the wind or while running up steep inclines. He learned to give entire speeches with a single breath.”

In time, his once weak voice boomed with power and clarity.

“Demosthenes locked himself away underground—literally—in a dugout he’d had built in which to study and educate himself. To ensure he wouldn’t indulge in outside distractions, he shaved half his head so he’d be too embarrassed to go outside,” writes Ryan.

Each day he would descend into his study to practice his voice, his facial expressions, and his ability to make strong arguments.

“When he did venture out, it was to learn even more,” Ryan recounts. “Every moment, every conversation, every transaction, was an opportunity for him to improve his art.”

His initial goal was to face his enemies in court and win back the inheritance that had been stolen. Which he did, notes Ryan. 

Most of the original inheritance had been spent, but it was no longer about the money. “Demosthenes’s reputation as an orator, ability to command a crowd and his peerless knowledge of the intricacies of the law, was worth more than whatever remained of a once-great fortune,” Ryan writes.  

“Demosthenes found his true calling: He would be the voice of Athens, its great speaker and conscience.” 

Yes, Demosthenes lost most of his inheritance. Yes, this was unfortunate. But in facing this reality, “he created a far better one—one that could never be taken from him,” writes Ryan. “He had channeled his rage and pain into his training, and then later into his speeches, fueling it all with a kind of fierceness and power that could be neither matched nor resisted.”

3: But, what about us? Ryan asks. How do we respond when we’re dealt a bad hand? Do we fold? Or, do we play it with everything we’ve got? When there’s an explosion, do we run toward it? Or are we the person running away from it? Or, worse, are we paralyzed and do nothing? 

“This little test of character says everything about us,” writes Ryan.

At one time or another, we’ve all said: “I am so overwhelmed, tired, stressed, busy, blocked, outmatched,” Ryan observes. What do we do then? “Go out and party. Or treat ourselves. Or sleep in,” he observes. “Or wait. It feels better to ignore or pretend. But [we] know deep down that that isn’t going to make it any better.”

What do we need to do? We must act. Take action. Do something. 

“Action, Action, Action!” was Demosthenes’s response when asked what the three most important traits of a speechmaker were.  

And, we must take “right action,” writes Ryan. “As a discipline, it’s not any kind of action that will do, but directed action,” Ryan writes. “Action requires courage, not brashness—creative application and not brute force.”  

Because life isn’t about what happens to us. Or where we start. It’s what we do with what we’re given.  

“People turn sh** into sugar all the time—sh** that’s a lot worse than whatever we’re dealing with,” writes Ryan. “We’re talking physical disabilities, racial discrimination, battles against overwhelmingly superior armies. 

“But those people didn’t quit. They didn’t feel sorry for themselves. They didn’t delude themselves with fantasies about easy solutions,” Ryan observes. “They focused on the one thing that mattered: applying themselves with gusto and creativity.” 

All they knew was what was in front of them. Instead of complaining, “they worked with it. They made the best of it. Because they had to, because they didn’t have a choice,” he writes.

“No one wants to be born weak or to be victimized. No one wants to be down to their last dollar. No one wants to be stuck behind an obstacle, blocked from where we need to go.” Of course not.

“But . . . No,” writes Ryan: “No excuses. No exceptions. No way around it: It’s on us.” 

There is only one path forward. The obstacle is the way.  

Ryan implores us to meet our problems… With the right action. With energy. With persistence. With a coherent and deliberate process. With iteration and resilience. With pragmatism. With strategic vision. With craftiness and savvy. And with an eye for opportunity and pivotal moments.

More tomorrow!


Reflection: Consider a current challenge in my life. What action can I take now to address the obstacle? 

Action: Do it. Today.

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