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Why is Stoicism worth listening to? Because it's battle tested. What good are theories about the world that are just that, theories? Philosophy from the ivory tower might be good for blowing minds, but as far as solving problems in the real world? Much less so.
Even in Marcus Aurelius' day, there was a suspicion of pen-and-ink philosophers. That is to say, thinkers who had never done anything but think.
We listen to Epictetus when he talks about finding freedom in the worst circumstances, because we know he did that. He survived the worst circumstances. Marcus Aurelius didn't get to theorize about Plato's Republic. He was trying to apply philosophy to Rome's empire. Seneca had no cushy tenure. He had a real job working for one of the most capricious and unstable rulers in ancient history.
In short, all these thinkers had what Nassim Taleb, a great Stoic writer and do himself, calls skin in the game. Skin in the game is not some mythical status either. People other than emperors and slaves and senators have it. Skin in the game is about being in the arena, about actually doing stuff, testing your ideas and your virtues in the fire of real life. This email, for instance, is not written by someone who has stared down Nero, of course. Who, besides Thrasea, has done that? But it is at least from someone who has run his own business, taken real risks, made it to the top of a few different fields, gotten married, started a family, worked on important projects, gotten his hands dirty, et cetera.
Advice without that perspective, advice from someone who just wants to give advice, philosophy from someone who sits protected from the reality of the world, cushioned from consequence in charge of nothing but pens and papers—it's worthless.
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