The Legend of Stoicism

You probably know the story of Stoicism.

But what you may not know is the weird coincidence behind it.

Around 300 BC, a wealthy merchant named Zeno, was travelling from Phoenicia to Piraeus, Greece.

He was a rare, purple dye seller.

His ship = his fortune.

Everything looked normal.

Until a storm broke out.

Today, this storm would be a piece of cake for our ships. But Zeno lost it all.

Did he swim to the coast? Was he rescued?

We don’t know.

All we know is he barely survived. But he was now homeless and poor.

The first thing he does—or one of the first things—is to visit a bookstore in Athens.

While skimming the books, one stunned him..

It was Xenophon’s Memorabilia.

In the book, Xenophon talked about Socrates and his ideas.

Namely—that virtue is sufficient for the good life (which the Stoics took as the foundation of the philosophy.)

Zeno liked what he read.

He didn’t know why, but he liked it.

As he held th book in his arms, he went to the bookseller and asked him:

“Where can I find such a man?” showing him to the book cover depicting Socrates.

“Follow this guy,” the bookseller said, pointing to the Cynic philosopher, Crates, who just happened to pass by.

But nothing “just happens.”

And Zeno knew that.

Later, as Zeno began to teach Stoicism—a more “human” approach to Cynicism—one student asked him what he thought of his shipwreck.

He didn’t complain. Nor whine for losing all his money.

Instead, he simply said:

“I made a prosperous voyage when I suffered shipwreck.”

The philosophy that claims that every obstacle is an opportunity began with an obstacle that Zeno turned into an opportunity.

I don’t want to make this email super long, so here are 3 things I learned from the Stoics this week writing the chapter “Problems Will Never Stop“ of my book.

1. Problems never stop.
   Odysseus thought Troy was the end of his troubles—yet every “victory” simply birthed a new struggle. You think love, money, or success will finally free you. They won’t. The truth is brutal: life is a cycle of problems. It just is. Once you accept that, you stop whining and start wrestling.

2. Choose your problems.
   Every path has pain—marriage or singleness, wealth or poverty, entrepreneurship or a job. You don’t escape difficulty; you trade one set for another. The only freedom you have is in deciding which burdens are worth carrying. That choice is everything.

3. Flux is the rule, not the exception.
   Seneca reminded us that anxiety is born in both prosperity and ruin. Triumph flips into trial; trial flips into triumph. Everything shifts—fast. The Stoic move is not to cling, but to treat every obstacle as training, every reversal as raw material.

See you on Monday—where I’ll be sharing the story of Odysseus + how he turned the obstacle (away from his wife and son, fighting monsters, wars, etc.) into courage and strength.

Talk soon,

Said the Stoic/Ioannis Sintoris

PS. Follow me on LinkedIn and ask me anything about Stoicism.