Ryan Holiday runs the original Marathon from Marathon to Athens

Executive overview

Doing the right thing is rarely convenient — Grant freed a slave while broke, not because the timing was good, but because it was right. Physical challenges are a Stoic training ground: they reveal what you're capable of and give you evidence you can draw on when life gets hard.

Holiday trained for and ran the original 26-mile Marathon-to-Athens route, motivated by a passage read in 2007. He finished, suffered sunstroke, and reflected on what the race taught him.

Discipline without wisdom is not enough — knowing how to apply effort matters as much as having it.

Doing the right thing regardless of cost

• Grant freed a slave in 1859 while personally broke, having just pawned his watch for Christmas presents
• Marcus Aurelius: just that you do the right thing — the rest doesn't matter, but that doesn't make it painless
• The time to do the right thing is always now, not when it's convenient
• Stoicism doesn't eliminate consequences; it clarifies the choice

The Battle of Marathon and why it matters

• 490 BC: 10,000 Athenian infantry faced a far larger Persian force on the plains of Marathon
• The Athenians charged, pushed the Persians into the marshes, lost fewer than 200 men
• With only hours to spare, they ran 24 miles back to Athens in full armor to defend the city
• The Persian fleet, seeing Athenian soldiers already there, withdrew — Athens was saved
• Stoicism itself is rooted in Marathon: the Stoa Poikile displayed a painting of the victory

Why Holiday ran it

• First encountered the story in 2007 reading Robert Greene's The 33 Strategies of War
• Murakami's What I Talk About When I Talk About Running revealed the route was actually runnable
• The run had been on his mind for at least 15 years before he did it
• He wanted to follow in the footsteps of people who had run that exact distance on that exact ground

Training

• Training ran at 105°F in Palm Springs the day after flying in from Texas
• Did a 19-mile long run on his 38th birthday
• Trained on steep Utah trails, at the Acropolis, in Ithaca, and up Mount Olympus
• Day-before rule: easy swim only — "do you want to be fast now or fast later?"
• Zeno: well-being is realized by small steps, but it's no small thing

Race day and the pain cave

• Started at 6:51 a.m. on July 13th, 2025, from the town of Marathon
• Goal: finish, not time — "no goal, no outcome, just want to finish"
• At 14 miles: focused only on the blue trail line, borrowed Joni Mitchell's image of the white line
• Courtney Dauwalter's framing: pain is the entrance to the "pain cave" — explore it rather than retreat
• Murakami: "the only opponent you have to beat is yourself the way you used to be"
• Hit a wall three miles from the end, suffered sunstroke, vomited in the Olympic stadium — finished anyway

What he learned

• Preparation matters: nutrition and start time could have been managed better
• Discipline must be paired with wisdom — knowing how to apply effort, not just applying it
• Seneca: he pities those who haven't faced adversity because they don't know what they're capable of
• Endurance challenges give you evidence: proof that you don't quit
• The stillness of several hours alone inside your own head is its own reward