Olivia: Alright Jackson, I'm going to give you the name of a 2,000-year-old leadership guide. Give me your best, most brutally honest, one-liner review. Jackson: Lay it on me. Olivia: How to Be a Leader by Plutarch. Jackson: Okay... 'Step 1: Own a toga. Step 2: Don't get stabbed. Step 3: Profit?' Olivia: (Laughing) Close! Minus the profit part, maybe. But you're not totally wrong about the stabbing. Today we are diving into How to Be a Leader: An Ancient Guide to Wise Leadership by Plutarch. Jackson: A name I definitely know, but I always picture him just writing about famous battles and the grand lives of Roman emperors. Olivia: And that's what's so fascinating! He wasn't just a historian. For decades, Plutarch was a priest at the Temple of Apollo in Delphi—the most sacred site in ancient Greece. So when he writes about leadership, it's not just political strategy; it's a form of moral philosophy. Jackson: Whoa, hold on. A priest at Delphi? That’s the place with the Oracle, right? The center of the world, according to the Greeks. That changes things. So this is less The Art of War and more... The Art of Not Being a Terrible Person in Power? Olivia: That is the perfect way to put it. For Plutarch, the two were inseparable. You couldn't be a good leader if you weren't first a good person. And his central, guiding principle for all of it is a simple, powerful phrase: "City before self." Jackson: 'City before self.' It sounds great on a poster. But what does it actually mean in practice? It feels like a slogan that’s easy to say and almost impossible to do. Olivia: I think Plutarch would agree it's difficult, but he'd say that's the entire point of leadership. And he didn't just preach it; he lived it. There’s this wonderful little story about him in his own small hometown of Chaeronea. He was this world-famous intellectual, friends with Roman elites, a big deal. But someone saw him personally supervising a local construction project—measuring tiles, checking cement work, really mundane stuff. Jackson: Like a celebrity CEO personally checking the office plumbing. Why was he doing that? Olivia: That's exactly what they asked him! They were basically saying, "Aren't you a little too important for this?" And Plutarch’s reply is the perfect summary of his entire philosophy. He said, "I’m not building these things for myself, but for my native city." He believed that no task was too humble if it served the community. True leadership wasn't about the glory of the position; it was about the good of the people. Jackson: Okay, I can see the appeal. It's about service, not status. But overseeing a local building project is one thing. What about when the stakes are higher? When you're dealing with real power, real enemies? That's where the 'city before self' idea usually falls apart. Olivia: He has an answer for that, and it's one of the most powerful stories in the book. It involves two of the most famous figures in Athenian history: Themistocles and Aristides.

Jackson: Ah, now we're getting into the big leagues. Weren't those two famous for hating each other's guts? Olivia: Viciously. They were the ultimate political rivals in Athens. They clashed on every single policy, they competed for every scrap of influence. Their animosity was legendary. Think of any two modern politicians who are polar opposites and despise each other—that was them. Jackson: I have a few pairs in mind. So what happened? Olivia: A crisis, of course. Athens needed to send a delegation abroad on a critical mission. The city's fate depended on it. And who do they choose to lead it? Themistocles and Aristides. Together. Jackson: That sounds like a recipe for absolute disaster. You're putting two people who can't stand each other in charge of a mission that requires total unity. Olivia: It should have been. But according to Plutarch, as they were about to cross the border out of Athenian territory, they stopped. And they made a pact. They agreed to "set aside their partisan rivalry" right there at the border. They decided that once they were representing Athens, they were no longer rivals. They were colleagues. Their personal hatred was left behind, and the only thing that mattered was the welfare of their city. Jackson: Wow. They literally checked their baggage at the door. Did it work? Olivia: It worked perfectly. They presented a completely unified front, advanced Athens's interests, and were incredibly successful. The moment they crossed back into Athens, they picked up their rivalry right where they left off. But when it mattered most, the city came first. For Plutarch, this was the gold standard of leadership. It’s the ability to subordinate your own ego, your own ambition, even your own very real personal animosity, to the greater good. Jackson: That's an incredible story. But it also feels like a political fairytale. It highlights a tension in Plutarch's own thinking, doesn't it? He also compared politics to the athletic arena, a place of intense competition where everyone is trying to win. How do you reconcile that competitive drive with this selfless ideal? Olivia: You've hit on the central challenge. Plutarch absolutely recognized that politics is a brutal, competitive sport. He knew that leaders are ambitious and want to win. But he believed that an educated leader—and by that, he meant morally educated—uses reason to control that impulse. Jackson: So what does 'moral education' even mean here? Is he saying leaders need to go back to school and read Plato? Olivia: In a way, yes! He tells a story about Plato himself. The people of Cyrene, a very prosperous and successful city, invited Plato to come and write laws for them. They wanted his wisdom to perfect their constitution. Jackson: That's like a country today inviting a Nobel laureate to rewrite their laws. It's a huge honor. Olivia: And Plato refused. He told them it would be impossible to legislate for them. When they asked why, he said it was precisely because they were so successful. He said, "For nothing is so naturally haughty and harsh and hard to govern as a man who has acquired a reputation for success." He knew their prosperity had made them arrogant and resistant to being governed, even by reason. Jackson: That is a serious burn. He's saying they're too successful to be told what to do. So an uneducated leader, in Plutarch's view, is one who is drunk on their own success and power? Olivia: Exactly. They're driven by insecurity and greed. He tells these chilling stories of tyrants like Clearchus, who was so paranoid he slept curled up in a box, or Aristodemus, who slept in a room only accessible by a trapdoor and a ladder his wife would remove every night. They had all the power in the world, but they were prisoners of their own fear. Jackson: Because they ruled by force, not by earning trust. Olivia: Precisely. For Plutarch, an educated leader cultivates what he calls Logos, or Reason. It's this internal force that governs your emotions and impulses. It's the voice that tells you to put the city first, to share credit, to listen to advice. A leader who can't govern themselves with reason will inevitably bring chaos and fear to their people. Your inner state becomes the state of the city. Jackson: It’s a powerful idea. The idea that a leader's character is their most important policy. It's not about the 10-point plan; it's about the person executing it. But this brings us back to the arena. How does this philosophical ideal actually survive contact with the enemy? With the messy reality of day-to-day politics? Olivia: And that's the perfect transition to the second big idea: how to actually behave in that arena. It's not enough to have a good heart; you need a playbook. And a big part of Plutarch's playbook is about handling power, especially as you get older.

Jackson: Okay, so we've established the internal philosophy. Now for the external strategy. What does Plutarch's playbook for the political arena look like? Olivia: One of his most surprising pieces of advice is about giving up power. It runs completely counter to how we think about leadership today, which is often about accumulating as much influence as possible. He tells the story of Theopompus, a king of Sparta. Jackson: Sparta, the ultimate military state. I imagine their kings weren't big on surrendering authority. Olivia: You would think so. But Theopompus saw that the absolute power of the monarchy was making it unstable and creating resentment. So he voluntarily gave some of his power away, creating a council of magistrates, the Ephors, to share in governing. His wife was furious. Jackson: I can imagine. She probably saw her family's legacy being diminished. Olivia: She confronted him, saying he was a disgrace for leaving his children a weaker kingdom than the one he inherited. And his response is just brilliant. He told her, "Actually it will be stronger, to the same degree that it is more stable." He understood that true strength isn't in absolute authority, but in stability and consent. By sharing power, he made the throne more secure, not less. Jackson: That is so counterintuitive. He strengthened his position by weakening it. It’s a lesson I think a lot of modern leaders, in corporations and in countries, could learn from. They cling to power so tightly they end up breaking the very thing they're trying to control. Olivia: And this idea connects directly to another one of Plutarch's key themes for the political arena: the role of experienced, older leaders. In our world, there's often a push for older leaders to step aside and make way for the new generation. Plutarch would have found that idea baffling. Jackson: Right, the book has that whole chapter, "Should an Old Man Engage in Politics?" which I assume is a rhetorical question for him. He's arguing that experience is an invaluable asset. Olivia: Invaluable. But not in the way you might think. He doesn't just say older leaders are wiser. He says their primary role is to mentor and protect the next generation. He tells the story of Aristides—the same guy who was rivals with Themistocles—and how he supported a young, up-and-coming politician named Cimon. Jackson: What was Cimon like? Olivia: He was brilliant but reckless. The public was critical of him; they thought he was out of control. Instead of seeing him as a threat or joining the criticism, Aristides, the established elder statesman, actively supported him. He saw Cimon's potential and used his own reputation to shield him and help him rise. He wasn't envious; he was a cultivator of talent. Jackson: He was playing the long game for Athens. He knew the city would need leaders like Cimon eventually. Olivia: Exactly. For Plutarch, envy is the most inappropriate emotion for an elder politician. Their job is to foster growth, to bear the brunt of unpopular decisions to shield younger colleagues, and to provide the steady hand of wisdom. He tells another story about an old man comforting a young Demosthenes after he was booed by the assembly. The old man just told him, "You remind me of Pericles," the greatest orator of all. That one piece of encouragement from a respected elder helped Demosthenes become a legend. Jackson: It's a beautiful vision of intergenerational leadership. But it also brings up a point of criticism I've seen about this book. While the wisdom feels timeless, some of the examples and the context are obviously ancient. The book is part of a series called "Ancient Wisdom for Modern Readers," and some reviewers have noted that it can be a challenge to bridge that 2,000-year gap. Plutarch's world was one of male-only politics, slavery, and different social norms. Olivia: That's a very fair point, and the translator, Jeffrey Beneker, addresses it directly. He notes that Plutarch obviously assumed an all-male audience of aristocratic leaders. The translation makes an effort to use more gender-neutral language where possible, to make the principles feel more universal. But Beneker also says he deliberately left in some of the more archaic examples—like references to a man's control over his wife—because, as he puts it, "These are artifacts of Plutarch’s world." Jackson: So he's not trying to hide the historical context. He's letting the ancient world be the ancient world, and asking us, the modern readers, to do the work of extracting the principle from the specific, sometimes dated, example. Olivia: Precisely. The goal isn't to pretend Plutarch is a 21st-century thought leader. It's to engage with a brilliant mind from a different time and see what enduring truths we can find. The principle of mentorship, of putting the city first, of strengthening your position by sharing power—those ideas transcend their original context. Jackson: It's a challenge, then. The book asks you not just to read, but to interpret and translate the wisdom for your own time. Olivia: It does. And it forces you to confront what is truly timeless versus what is just a product of a specific era. That's part of the value. It's not a simple how-to guide; it's an exercise in critical thinking about the very nature of leadership.

Jackson: So after all this—the philosophy, the stories of rivalries and mentorship, the challenge of interpreting ancient wisdom—what's the one thing a modern leader, whether they're running a small team or a whole country, should take from a 2,000-year-old priest from Delphi? Olivia: I think it’s that leadership isn't a title you hold or a role you perform, but a state of being. Plutarch's radical and enduring idea is that your character is your policy. A leader who hasn't mastered themselves—their ego, their greed, their rivalries—will inevitably inflict that internal chaos onto their city or their company. The state, in his view, is just the leader's soul, writ large. Jackson: That's a heavy thought. It puts all the responsibility back on the individual's inner life. It's not about external factors or political maneuvering. It's about your own integrity. Olivia: It is. And it completely reframes the central question of leadership. He tells us that a good leader should constantly be reminding themselves of their duty, just like Pericles, who would whisper to himself every time he put on his general's cloak, "Be mindful, O Pericles, that you are leading free people." It was a constant check on his ego. Jackson: It’s a practice, not a position. Olivia: A continuous practice. So the question Plutarch leaves us with isn't 'What should I do?' but 'Who should I be?' It’s a profound shift from tactics to character. And it's a question that is just as urgent today as it was in ancient Rome or Greece. Jackson: And it makes you look at leaders differently. It’s a powerful lens. We'd love to hear what you all think. Does this ancient wisdom hold up in the modern world? Find us on social media and share one leader—past or present—who you think truly lived by that principle of 'City before self.' We'd love to see your examples. Olivia: This is Aibrary, signing off.