Disclaimer: this post contains spoilers for Christopher Nolan’s 2026 depiction of The Odyssey. If you are planning to watch the movie, I would recommend 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 Golioth prior to our acquisition by Canonical. Over the years I’ve tried to commit a significant portion of my time to listening to feedback from individuals on those teams, reflecting on my own decisions and motivations, and seeking advice and guidance from those who have been successful leaders.
I am also a diehard Christopher Nolan fan, with four of my top five favorite movies being Nolan films (and yes, one of them is Tenet). I’ve been looking forward to The Odyssey since the announcement of its release date, and I finally got the opportunity to go and see it in all of its IMAX glory.
Well, most of its IMAX glory; we don’t have a 70mm IMAX theater anywhere in 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 away new lessons from the experience. After all, the story has been retold for more than 2,500 years. Nevertheless, the choices in Nolan’s screenplay, combined with encountering it as my 30-year-old self rather than my 16 year-old-self, left me pondering the story’s concepts in a new light over the following days. While Odysseus is many things, perhaps his most defining trait is his leadership. Throughout the Odyssey, he is constantly making decisions that have a profound direct impact on the soldiers he is leading, but also indirectly impact his family, country, and all of society.
In many ways, Odysseus plays a sort of CTO role. He both devises technical plans and implements them alongside his men, but ultimately answers to Agamemnon, his hot-headed CEO. In other words, he leads from the front. However, like many hand-on leaders when faced with constraints, he can fall into the trap of thinking that he can overcome obstacles through sheer will or his own cleverness. This manifests as both acts of hubris and an inability to accept hard truths at various points throughout the story.
Odysseus’s successes and failures highlight a few leadership lessons that I have learned throughout my own journey, many times through painful failures.
Respect is Earned, Continually Link to heading
Odysseus: “Is this a mutiny?”
Eurylochus: “It’s up to you.”
After the victory in the Trojan War, Odysseus has undoubtedly cemented his legacy with the success of the Trojan Horse scheme. You would think that there is nothing that he could do to lose respect, especially from the men who witnessed his exploits in person. However, in a moment of pride, Odysseus fires an arrow at Poseidon’s son, Polyphemus, after he and his men had already escaped entrapment in the giant’s cave.
Note that Nolan chooses this act of hubris rather than having Odysseus disclose his name, as is the case in the original poem).
A chase back to the boats ensues, and the men come to believe that their subsequent misfortune is a result of Odysseus offending Poseidon. Whether this is true or not, it eventually outweighs Odysseus’s prior legendary feats, and results in the exchange about mutiny and the men requesting that he remain at shore when they arrive at Aeaea. It is a visceral illustration of the fact that a leader can never rest on their laurels. Their team will and should demand that they demonstrate poise and composure at all times. Failure to do so comes with consequences.
Let Your Team Make Mistakes Link to heading
Circe: “Leave your weapons outside.”
Following the subdued mutiny on the beach of Aeaea, Odysseus does not impede his men’s trek up the hill as he goes off to hunt for food. Along the way, the men encounter some very out of place animals, such as a lion and a jaguar, that foreshadow the events that readers of The Odyssey already know are about to transpire. Upon reaching a clearly inhabited hut, the men encounter Circe, who acts frightened by their arrival. Nevertheless, she agrees to feed them as long as they remove their armor and weapons and place them behind the hut.
In their hunger, the men look past the pile of rusting armor evidently belonging to previous soldiers who had been presented with the same prompt. The subsequent scene is by far the most disturbing in the movie, as Circe takes a very… hands on approach in transforming the men into pigs. When Odysseus later makes his way to the hut, he notices all of the signals that his men so conveniently overlooked. He shrewdly identifies Circe’s bird as someone she cares about in animal form, and uses it as leverage to have her transform the pigs back into his men.
We also get one of the quotes of the movie when Circe yells “Back into your disguises!” as the pigs retake the shape of the men.
It is not a stretch to think that Odysseus could have saved his men from this dreadful experience had he insisted on accompanying them initially. Had he known the pain they were destined to experience, he may have been more persistent. However, there is value in not standing in the way of individuals who wish to assume more responsibility. They may demonstrate the ability to lead, to both others and themselves, or they may learn a valuable lesson that shapes how they approach future leadership opportunities. Too much protection at best slows their growth, and at worst stunts it.
Be Tactful with Information Link to heading
Eurylochus: “Why didn’t you tell us?!?”
After the encounter with Circe at Aeaea, Odysseus and his men sail to Hades, where Odysseus has a private conversation with Tiresias. Tiresias informs Odysseus that they will have to choose between sailing into a whirlpool (Charybdis) or by a six-headed monster (Scylla). The former would result in the entire crew being lost, whereas the latter would mean that six men would die.
As they leave Hades, Odysseus wrestles with the decision whether to tell his men of the prophecy or not. He eventually decides not to, and even goes one step further to command them to sail into the whirlpool, an order he knows they will defy, resulting in passing by Scylla and losing six crew members. Odysseus not only withholds the information for his men, but manipulates them into making the decision that he believes to be correct. In doing so, he implicitly makes the decision for them, while avoiding taking ownership of doing so.
Though withholding for the purpose of manipulation is a fairly obvious negative leadership trait, choosing when and how to disclose information is a decision that leaders are confronted with on a daily basis. Early on in my career I would characterize myself as an “information transparency maximalist”, opting to frequently share virtually all information I received with all members of the team. Some of this was likely borne out of personal insecurity, or perhaps even a lack of accountability (i.e. telling everyone everything can act as a diffusion of responsibility). I would still consider myself as a leader that biases towards transparency, but I have learned more about the value of compressing or synthesizing information. After all, if you act as a strict passthrough, you are introducing communication overhead without adding value.
Setting aside the manipulation of his crew, perhaps Odysseus can reconcile the decision to sail by Scylla by saying that he was optimizing for the best outcome for the greatest number of people. In all organizational structures, there is an exchanging of personal agency for efficiency. It is important that there is explicit alignment on the amount of agency that is being surrendered to the leader. The leader is entrusted to not overstep that agreement.
I won’t pretend to understand the contract between Achaean soldiers and their generals. I think it is safe to assume that they are surrendering more agency than most of us would ever be comfortable with. Nevertheless, I wouldn’t be surprised if Odysseus felt some regret in how transparent he was about the prophecy. There is some evidence that this event caused him to recalibrate, as he later informs the crew of the part of the prophecy that states that if they eat the cattle of the sun god they will all be killed by Zeus.
Most of the vast majority of decisions that leaders make are not as consequential as Odysseus’s predicament. However, his scenario provides a useful test for whether it is better to share information with a team or not: how would they react if they were to learn of the information later? This typically has a high correlation to the personal impact that the information has on each team member. In this case, the impact was death for some of the crew, and extreme guilt for the remaining members. I’d say that is pretty significant!
Continue to Refine Yourself Link to heading
Odysseus: “Put the wax in the men’s ears. None for me. Tie me to the mast.”
In one of the most famous stories from The Odyssey, Odysseus, on the advice of Circe, instructs his men to fill their ears with wax as they sail by the Sirens, so as not to be drawn in by their intoxicating song. However, he refuses the wax for himself, instead requesting that the men bind him to the mast so that he can hear the song of the Sirens, but not fall into the trap of pursuing them. This category of directive has become known in modern times as a Ulysses pact.
The men don’t directly gain anything from Odysseus hearing the song of the Sirens, and at first it may seem like an ego-driven decision. If he truly prioritized the crew, would he incur the risk of either being driven mad by the song, or somehow breaking free from the mast and sailing into their trap? Perhaps, but the fact that Odysseus survives suggests that he has a strong grasp of his own limitations and believes that the wisdom he will gain from the experience far outweighs the risk. Or maybe he just couldn’t pass up the opportunity to be the first person who heard the Sirens and lived. We can never know for sure.
What we do know, and what is depicted so vividly in Nolan’s rendition, is the extreme torment that Odysseus underwent in hearing the song while being restrained. We also know what the song was about, courtesy of Eurylochus’s inquiry.
Odysseus: “All the things you want it to be. Then, all the things you wish you’d never wish for. It was the delicious itch you go to scratch but find it’s under the skin, you can’t reach it. So the delicious itch becomes unbearable. Told you what you most want is what you most can’t have. And what you most can’t have is what you already had and lost. It was the song of all the promises I failed to keep. And it told me I don’t really want to go home.”
As a leader, it can be easy to always see the best option as what prioritizes your team. However, if you do not take the opportunity to also refine yourself, you will be a less effective leader for them in the long run. Odysseus is attentive to the opportunity that he has to refine his understanding of the world they are living in and the role they played in creating it. This moment may be the point at which Odysseus first begins to recognize the irreversible impact of the actions he and his men carried out in Troy. He understands that, though they all long to be home, the home they are returning to will never be the one that they left. This knowledge guides him throughout the remainder of his journey home.
Do Not Win at All Costs Link to heading
Odysseus: “What if when he left the belly of the horse and opened the gates of Troy he saw ten years of rage pour into that city in one night. We left them a gift in offering of peace that they took into their home. We violated all that’s ever sacred between people and turned the fight into a hunt. To burn the walls of Troy was to burn the world entirely, including his home. What if he knew, that very night as he walked through fires of anarchy and pain. And in the days of sweaty celebrations that followed, what if he knew exactly what he’d done?”
Odysseus: “One man’s idea, one man’s trick to break Zeus’s Law forever. We live in a world of palaces, trades, language, blinded with beauty until we broke it.”
Odysseus’s monologue upon being reunited with Penelope codifies the insight that began to take shape when he heard the song of the Sirens. What the world sees as his greatest triumph, he has come to realize is actually his greatest failure. He has destroyed the precedent of treating strangers with respect, which has created a domino effect, causing society as a whole to crumble.
It is possible that Odysseus and his men did not understand the value of the civilization in which they lived, and because of this they were flippant in their protection of it. I think it is more likely that they were blinded by their ten years of suffering and their desire to return home to their families. This led them to adopting an any-means-necessary mindset, where no cost was too great on the way to securing their victory.
The more resources you invest in any effort, whether it be time, energy, or money, the easier it can be to fall prey to tunnel vision. When you lose the ability to step back and look at the big picture, you can end up compromising principles that your past self would have considered non-negotiable. In the end, the cost of the compromise is so great that you look back and wonder how you ever thought that the trade-offs were worth it.
Many of Odysseus’s men end up losing their lives despite their victory in Troy. Agamemnon faces reprocussions of his own brash decision-making. Odysseus and the others who survive are forced to live the rest of their days longing for the thing they most can’t have, the thing they already had and lost.
Though Odysseus does make it back to his wife and son, I don’t think it is a stretch to say that he may have chosen to die in Troy rather than enacting his scheme if he were given the opportunity to do it over again.
Is Odysseus a Good Leader? Link to heading
We’ve established that Odysseus leads, but does he lead well? To address the elephant in the room… his stats are not great. All of the men he is responsible for end up dying, and an uncomfortably straight line can be drawn from his questionable decision-making to their deaths. Many of the leadership lessons described in this post are illustrated using Odysseus as a cautionary tale, rather than an exemplar of best practices. It is frustrating, though perhaps not unfamiliar, for a person to be held up as a hero due to a single act, when in reality that act is surrounded by a litany of failures.
While Odysseus’s recognition of the harm his great triumph set in motion does not negate his short-comings, I do believe that the best leaders are able to identify when the thing that they are praised for is actually something that requires reform. In the startup world, a classic example of this scenario is when a company transitions from a small group acting as heroes to a larger organization where it is optimal for knowledge and workload to be distributed across many individuals. I myself have been guilty of holding too tightly to roles and responsibilities that I needed to surrender.
Ultimately the answer to whether someone is a good leader depends on the attributes that you value most highly. If flaw minimization is your goal, Odysseus does not stack up well. However, if you are looking for someone who will continually examine their own motivations and is willing and able to accept their mistakes, he certainly demonstrates those qualities. Maybe I gravitate towards Odysseus because I know that I am deeply flawed, yet I still believe that I have something to offer as a leader. But perhaps I really just want to be the person that heard the song of the Sirens and lived.