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5 min readRunning 50 Kilometers Through Rome To Understand Stoicism
Ryan Holiday ran 50 kilometers through Rome, passing the city's most important Stoic sites, and he did it because it was hard. That was the whole point. Drawing on an idea from Jesse Itzler, Holiday explains that you should pick something genuinely difficult to do every year—something so ambitious that no matter how the rest of the year goes, you look back and remember that as the year you did that thing. The value isn't in succeeding or failing; it's in having wrestled with something beyond your normal limits. "If it isn't, you're not gonna remember it, it's not gonna mean anything," he says. "So you want to pick something that's big, that's ambitious, that scares you a little bit. And this thing scares the shit out of me."
The Inner Citadel
Running past Hadrian's tomb—known as Castel Sant'Angelo, the castle that protected Rome from invasion—Holiday draws the connection to one of Stoicism's most powerful images: the inner citadel. The real fortress, he argues, has to be inside. When we do hard things, when we train, when we push ourselves physically, we are reinforcing that inner reservoir of strength. Thomas Paine called it "the cabinet of fortitude" when he wrote to George Washington. That inner citadel is what protects us from external events and what we draw on when things get genuinely hard.
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What you'll learn
- 1 (00:17) **The Challenge: Why Run 50K Through Rome?** - The host announces he will run 50 kilometers through Rome to Stoic sites, framing it as a "hard thing" that is good by Stoic principles.
- 2 (02:42) **The Inner Citadel & The Body's Obedience** - Running past Hadrian's Tomb (Castel Sant'Angelo), he connects the physical fortress to the Stoic concept of the "inner citadel."
- 3 (05:06) **The Futility of Trophies & External Validation** - Standing before Marcus Aurelius' victory column, he reflects on why we do hard things.
- 4 (06:20) **Cold Exposure & The Musonius Rufus Principle** - At the Trevi Fountain, he clarifies his motivation for seeking discomfort like cold exposure.
- 5 (07:18) **Marcus Aurelius: The Ruins & The Fight to Be Good** - At the Capitoline Hill statue of Marcus Aurelius, he reflects on the emperor's humanity.
- 6 (09:04) **Gallows Humor & The Banishment of Musonius Rufus** - Still early in the run, he shares a Stoic anecdote about facing the inevitable with calm.
- 7 (12:16) **Getting Lost: Planning vs. Plans** - He takes a wrong turn and runs an extra mile, using the setback to illustrate a key Stoic principle.
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Show Notes
Come along with Ryan as he sets out to run farther than he ever has before: 50 kilometers through Rome, past some of the most important Stoic sites in the world.
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This experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. Ryan Holiday, who’s a client of Wealthfront, receives cash compensation from Wealthfront Brokerage for paid testimonials in his podcast, creating a conflict of interest. More details available via the referral link. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Account balances (up to an overall boosted rate of 4.30% for a limited time when including the three month 0.75% APY boost for new clients) when you direct deposit $1,000 a month, plus open, fund, and maintain an investing account. Wealthfront may change or end the program at an
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