I saw The Odyssey yesterday (you know I’m an ancient history nerd) and walked out thinking about both ancient Greece and its implications for today.

Along with its companion, The Iliad, the Homeric epics wrestle with life and leadership questions as relevant as they were in 800 BC. Here are five that jumped out at me.

1. Can we, or should we?

Homer refers to Odysseus as “clever.” His ingenious ideas (the Trojan Horse, fooling the Cyclops, and tying himself to the mast to hear the Sirens) accomplished their goal but created larger complications.

Through his trials, Odysseus develops wisdom. He shifts from “can we accomplish this?” to “should we?” and “how to address the risks this might set in motion?“

A company today can use AI to monitor every employee interaction, measure productivity, and identify potential underperformance. The technology might improve efficiency, but might also create a culture where people feel watched rather than trusted.

Sometimes the actions you take to save a nickel cost the company a dime (thank you, Coach Tim Neiman, for this idea).

2. What is the value of sacrifice, and when is it justified?

Lacking favorable winds to sail for Troy, Agamemnon sacrificed his own daughter. The winds changed. The value of making a sacrifice, Odysseus noted, lies in the cost to the one sacrificing. Virtue signaling is the illusion of sacrifice without the cost to the signaler.

A company faces a serious downturn. The executive team eliminates 10% of the workforce to protect the business. The remaining employees absorb the work while senior leaders retain their bonuses.

Layoffs may be necessary, but who bears the sacrifice? Are the decision-makers sharing the burden or spending other people’s livelihoods?

Real sacrifice costs the one making it. Everything else is theater.

3. Where is the line we will not cross?

The Greeks left the Trojan Horse as a “gift” on the beach. When the Trojans brought it inside the city, the Greeks crept out at night and opened Troy’s gates. The Greek army destroyed the city and killed or enslaved every person inside. The gods were upset and punished the transgressors. The war exhausted the victors. Greek civilization declined until the 5th century BC.

A salesperson is one contract away from hitting their annual target. The customer asks whether the product can perform a function still under development. Saying “yes” will probably close the deal.

Under what circumstances is that reasonable confidence versus deliberate deception?

What happens when “fake it until you make it” becomes an accepted way to make the number (et tu, Theranos?)?

4. Am I creating dependency or building capacity?

Odysseus was extraordinarily resourceful, but his crew often depended on his ingenuity to survive.

In Homer’s story, Odysseus personally steered the ship for nine straight days while guarding a bag containing the dangerous winds. He told no one what was inside. With Ithaca finally in sight, exhaustion overcame him. While he slept, his suspicious crew opened the bag, releasing the winds and blowing the ship far from home.

Odysseus had gotten them within sight of their destination. But had he created the team-powered momentum to reach it?

A CEO discovers that personally intervening in troubled projects gets fast results. Each rescue confirms the leader’s value. Meanwhile, the organization learns to wait. People know the leader has the answer, so they stop developing their own.

How do you become the right kind of indispensable?

5. What do we owe those who helped us reach the destination?

After returning home, Odysseus and Penelope went into voluntary exile, sailing west to honor the service and sacrifice of the people he had led. Leaders are often remembered by name for achievements made possible by many, including some who paid a far greater price.

After a successful acquisition, the CEO and senior team receive recognition and significant financial rewards. Meanwhile, employees who built the company endure restructuring, relocation, or job losses.

A contractual obligation may have ended, but has the moral obligation?

As Odysseus said in the movie, “The clearest view of a person is from below.”

Which of these questions resonates most with a challenge you’re facing right now?

Comment below. I read every response.

If this made you think of a colleague, a peer, or someone navigating a tough leadership moment, share it. The best conversations start with a question worth asking.

And if someone shared this with you and you’d like to receive future letters, subscribe here. I’d love to have you along.

The gates of Mycenae, where Agamemnon launched the Trojan War.