Why Odysseus Lost All His Men: Leadership, Failure, and Responsibility

Christopher Nolan’s film has brought Homer’s 『The Odyssey』 back to the center of popular attention. But when the original voyage is converted into an organizational scorecard, the results are difficult to explain as merely a heroic tale. Odysseus departed Troy with 12 ships, lost all his companions, and returned to Ithaca alone with the help of other people’s ships.

This fact does not immediately establish him as the “worst leader.” Conversely, he cannot be called a successful leader merely because he endured uncertainty and ultimately reached his destination. 『The Odyssey』 is useful to today’s leaders not because it provides a model answer, but because it presents a complex case in which performance, responsibility, luck, authority, and trust collide.

The First Fact to Check: Did Every Member Really Die?

In 『The Odyssey』, all the companions who sailed with Odysseus die before returning home. The opening of the work also summarizes that although he tried to save his companions, he ultimately failed to do so. However, not every death resulted from a single decision or the same cause.

Therefore, the claim that “Odysseus killed every one of his subordinates” is overly simplistic. A more accurate statement is: “Every companion on the return voyage under his command died, and the outcome resulted from a combination of his companions’ choices, the leader’s decisions, and intervention by nature and the gods.”

Are an Individual’s Return and an Organization’s Success the Same?

To evaluate a leader’s performance, the unit of success must first be defined.

• Personal objective: Odysseus survived, returned to Ithaca, and reclaimed his throne and family.
• Mission objective: He failed to bring the fleet and his companions home.
• Organizational preservation: He lost all 12 ships and every companion.
• Time and resources: After the Trojan War ended, the return journey took another 10 years.
• Ethical outcome: Some companions died from unavoidable threats, but reckless exploration and ostentatious behavior contributed to some of the losses.

This distinction also applies to modern organizations. Even if a founder receives a large personal reward by selling a company, the project cannot be called a success for every stakeholder if employees and customers are left with severe harm. We must ask not only whether the objective was achieved, but whose objective it was and who bore the cost.

Assessments Favorable to Odysseus

Odysseus’s leadership has genuine strengths. Denying them would mean overlooking the complexity of crisis response depicted in the work.

He Made Decisions Even Under Uncertainty

As in the escape from the Cyclops’ cave, he devised a workable plan under conditions of limited time and incomplete information. The process of intoxicating and blinding the monster, then escaping by tying themselves beneath the sheep, is an example of problem-solving that combined observation, deception, and resourcefulness.

He Never Lost Sight of His Destination

Despite repeated temptation and frustration, Odysseus did not abandon his goal of returning to Ithaca. In a long-term project, persistence of purpose can give an organization the strength to endure short-term turmoil.

He Shared the Risks Himself

He was not someone who merely issued orders while remaining in a safe place. He personally participated in reconnaissance and combat and confronted Circe to save his companions. When those in charge share the risks, the legitimacy of their orders and the trust of their members can increase.

Not Every Failure Was Controllable

Storms, monsters, and the hostility of the gods lay beyond human prediction and control. In modern terms, they correspond to external shocks that leaders cannot eliminate, such as sudden market shifts, war, disasters, and regulatory changes. The mere fact that the outcome was bad does not automatically make the decision made at the time a bad one.

Assessments Unfavorable to Odysseus

It is also dangerous to read him only as a responsible hero. The work repeatedly depicts losses that could have been avoided or reduced.

Curiosity and Vanity Turned into Organizational Risk

In the Cyclops’ cave, Odysseus’s companions propose taking the food and livestock and leaving quickly. Odysseus stays because he expects to meet the owner and receive a gift. After escaping, he reveals his name and taunts Polyphemus, provoking Poseidon’s retaliation.

This can be read as a case in which an individual’s desire for honor imposed the cost of risk on the entire organization. A leader’s boldness and vanity can look similar until the results appear, so a process for reviewing opposing views is necessary.

He Monopolized Even Necessary Information

Odysseus is warned that Scylla will kill six men, but he does not tell the sailors about the specific danger. Even if this was intended to prevent them from dropping their oars in terror, the ethical problem remains that he withheld information from people who might be sacrificed.

There are cases in organizations where confidentiality is necessary. But the discomfort of disclosing information must be distinguished from an operational need to restrict it. Decisions that deprive members of the opportunity to understand and prepare for danger carry a greater obligation to explain.

Repeating Orders Could Not Replace Trust

In the episodes involving the bag of winds and the cattle of the sun god, his companions disobey orders. This could simply be viewed as a problem caused by incompetent and greedy subordinates. But it is also important that they were not told what was inside the bag and came to suspect that Odysseus was monopolizing the rewards.

Compliance with orders is not guaranteed by title alone. When information gaps are wide and doubts about fairness accumulate, members trust rumors more than the leader’s explanations. Psychological safety does not mean only a comfortable atmosphere. It also includes an environment in which people can raise questions, report risks, and verify the basis for decisions.

How Should We Evaluate a Leader Who Chooses the Lesser Evil?

The choice between Scylla and Charybdis is a classic lesser-evil dilemma. On one side, some people are certain to die; on the other, everyone may die. Rather than evaluating such decisions simply by counting the outcome, they should be examined through the following questions.

1. Could the danger have been anticipated in advance?
2. Was there a realistic alternative that would have caused less harm?
3. Did the decision-maker prioritize collective survival over personal benefit?
4. Was as much information as possible provided to the people affected?
5. Were preparations made and resources allocated to reduce the harm?
6. After the outcome, did the decision-maker acknowledge responsibility and review the decision-making process?

The failure to save everyone is not in itself proof of incompetence. But “there was no other choice” cannot automatically be grounds for exemption from responsibility either. Sacrifices that were unavoidable must be distinguished from those caused by inadequate preparation.

Why Is a Failed Commander Remembered as a Hero?

『The Odyssey』 is believed to have taken shape around the late 8th to early 7th century BCE. Thus, saying that it has been “remembered for 3,000 years” is a literary exaggeration, but it is certainly an ancient memory in the sense that the work has been transmitted for approximately 2,700 years or more.

Odysseus remained a hero not merely because he was a successful manager.

• He represents the fear and temptation that humans experience in an uncertain world.
• He embodies a type of hero who solves problems through ingenuity rather than strength.
• He carries the universal desires for homecoming, family, and the restoration of identity.
• He is an imperfect figure with flaws and arrogance, leaving ample room for interpretation.
• He has been continuously reproduced through ancient Greek oral tradition and through education, translation, performance, and publication.

In other words, the fact that he has long been remembered does not justify all his decisions. Cultural influence and ethical exemplarity are separate criteria for evaluation.

An Easily Overlooked Perspective: The Survivor Owns the Story

Some of the central adventures in 『The Odyssey』 are presented as a retrospective account that Odysseus himself gives to the Phaeacians. His dead companions cannot speak about their own judgments, fears, or assessments of their leader. The opening of the work emphasizes the recklessness of the companions who ate the cattle of the sun god, but that does not explain every loss, including those involving the Cyclops and the Laestrygonians.

This structure resembles failure reports in modern organizations. When surviving executives or project managers write retrospectives, the following biases can emerge.

• Successful judgments are explained as the leader’s ability, while failures are attributed to the environment or members’ disobedience.
• Risks that could not have been known in advance become mixed together with warnings that were actually ignored.
• The testimony of members who left or suffered harm is omitted from the record.
• An individual’s survival or promotion is presented as the success of the entire organization.

Therefore, a leader’s retrospective alone is insufficient to turn failure into learning material. Decision-making records, opposing opinions expressed at the time, testimony from frontline members, risk indicators, and outcomes for each stakeholder must all be preserved. This is the difference between a heroic narrative and organizational learning.

Lessons for Modern Leaders

What should be learned from Odysseus is not unconditional decisiveness or the glorification of sacrifice.

• Agree on the scope of performance first. Measure not only personal survival, revenue, and adherence to schedules, but also member safety and harm to customers.
• Review decisions separately from outcomes. A good result does not justify a reckless decision, and a bad result does not immediately invalidate a reasonable one.
• Use dissent as a risk-detection mechanism. Do not treat a colleague’s proposal to withdraw as weakness or a lack of loyalty.
• Set clear standards for restricting information. Distinguish secrecy required for security from concealment intended to evade responsibility.
• Separate the leader’s desires from the organization’s purpose. Examine whether honor, recognition, or a desire for revenge is increasing collective risk.
• Preserve multiple voices in records of failure. Do not conclude a postmortem assessment with only the surviving person in charge’s account.

Conclusion: Is Taking the Helm Again Enough?

Odysseus did not give up, did not avoid making decisions in the face of crisis, and ultimately reached his destination. At the same time, his curiosity and vanity created avoidable dangers, while his monopolization of information and lack of trust reduced his companions’ chances of survival.

True responsibility begins with the willingness to take the helm even after failure, but it does not end there. Leaders must openly examine why the ships were wrecked, whose warnings were ignored, and whether another path could have reduced the sacrifices. The most important lesson Odysseus offers today’s leaders is not “keep going to the end,” but “ask whom you lost while reaching your destination and what responsibility you bear for those losses.”