Leadership Lessons from The Odyssey · Daniel Mangum
Disclaimer: this post contains spoilers for Christopher Nolan’s 2026 depiction<br>of The Odyssey. If you are planning to watch the movie, I would recommend<br>doing so prior to reading, even if you are already familiar with the story.
I’ve spent most of my career leading teams, including serving as CTO at<br>Golioth prior to our acquisition by<br>Canonical. Over the years I’ve tried to commit a<br>significant portion of my time to listening to feedback from individuals on<br>those teams, reflecting on my own decisions and motivations, and seeking advice<br>and guidance from those who have been successful leaders.
I am also a diehard Christopher Nolan fan, with four of my top five favorite<br>movies being Nolan films (and yes, one of them is<br>Tenet). I’ve been looking forward to The<br>Odyssey since the<br>announcement of its release date, and I finally got the opportunity to go and<br>see it in all of its IMAX<br>glory.
Well, most of its IMAX glory; we don’t have a 70mm IMAX theater anywhere in<br>North Carolina so a 1.90:1 aspect ratio had to suffice.
I went into the movie with high expectations, but I wasn’t planning on taking<br>away new lessons from the experience. After all, the story has been retold for<br>more than 2,500 years. Nevertheless, the choices in Nolan’s screenplay, combined<br>with encountering it as my 30-year-old self rather than my 16 year-old-self,<br>left me pondering the story’s concepts in a new light over the following days.<br>While Odysseus is many things, perhaps<br>his most defining trait is his leadership. Throughout the Odyssey, he is<br>constantly making decisions that have a profound direct impact on the soldiers<br>he is leading, but also indirectly impact his family, country, and all of<br>society.
In many ways, Odysseus plays a sort of CTO role. He both devises technical plans<br>and implements them alongside his men, but ultimately answers to<br>Agamemnon, his hot-headed CEO. In<br>other words, he leads from the front. However, like many hand-on leaders when<br>faced with constraints, he can fall into the trap of thinking that he can<br>overcome obstacles through sheer will or his own cleverness. This manifests as<br>both acts of hubris and an inability to accept hard truths at various points<br>throughout the story.
Odysseus’s successes and failures highlight a few leadership lessons that I have<br>learned throughout my own journey, many times through painful failures.
Respect is Earned, Continually
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Odysseus: “Is this a mutiny?”
Eurylochus: “It’s up to you.”
After the victory in the Trojan War, Odysseus has undoubtedly cemented his<br>legacy with the success of the Trojan Horse scheme. You would think that there<br>is nothing that he could do to lose respect, especially from the men who<br>witnessed his exploits in person. However, in a moment of pride, Odysseus fires<br>an arrow at Poseidon’s son, Polyphemus, after he and his men had already escaped<br>entrapment in the giant’s cave.
Note that Nolan chooses this act of hubris rather than having Odysseus<br>disclose his name, as is the case in the original<br>poem).
A chase back to the boats ensues, and the men come to believe that their<br>subsequent misfortune is a result of Odysseus offending Poseidon. Whether this<br>is true or not, it eventually outweighs Odysseus’s prior legendary feats, and<br>results in the exchange about mutiny and the men requesting that he remain at<br>shore when they arrive at Aeaea. It is a<br>visceral illustration of the fact that a leader can never rest on their laurels.<br>Their team will and should demand that they demonstrate poise and composure at<br>all times. Failure to do so comes with consequences.
Let Your Team Make Mistakes
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Circe: “Leave your weapons outside.”
Following the subdued mutiny on the beach of Aeaea, Odysseus does not impede his<br>men’s trek up the hill as he goes off to hunt for food. Along the way, the men<br>encounter some very out of place animals, such as a lion and a jaguar, that<br>foreshadow the events that readers of The Odyssey already know are about to<br>transpire. Upon reaching a clearly inhabited hut, the men encounter<br>Circe, who acts frightened by their<br>arrival. Nevertheless, she agrees to feed them as long as they remove their<br>armor and weapons and place them behind the hut.
In their hunger, the men look past the pile of rusting armor evidently belonging<br>to previous soldiers who had been presented with the same prompt. The subsequent<br>scene is by far the most disturbing in the movie, as Circe takes a very…<br>hands on approach in transforming the men into pigs. When Odysseus later makes<br>his way to the hut, he notices all of the signals that his men so conveniently<br>overlooked. He shrewdly identifies Circe’s bird as someone she cares about in<br>animal form, and uses it as leverage to have her transform the pigs back into<br>his men.
We also get one of the quotes of the movie...