Leadership Lessons from Odysseus

A man wandering a beach collecting driftwood with someone watching him in the distance. Bronze age imagery.
Odysseus on the beach with some company. Image from Midjourney v8.2

Art has a funny way of capturing life's moments. Great art lingers long after you experience it and offers valuable lessons. This week, I finally left the house and saw Christopher Nolan's retelling of Homer's The Odyssey. While critics argue over Nolan's casting choices, the film's real pulse lies in its portrait of leadership.  

The story of the Odyssey follows the aftermath of the Trojan War and Odysseus's quest to return to his family. Half a world away and beset by angry gods, Odysseus uses his intelligence to find his way home and eventually reclaim his kingdom.

Flotsam on the Shore

Nolan takes a few liberties with the story but stays true to the overall arc of Homer's epic poem. The movie opens with Odysseus puttering on the beach almost in a narcotic fog. He collects driftwood washed ashore and stacks it into a raft. It is a half-hearted effort, and he is not sure why. He is alone except for a woman named Calypso. Over the first two-thirds of the movie, the fog lifts, and he remembers the Trojan War and his attempt to return home before he washed ashore on Calypso's beach.

Earlier this year, I wrote about the Odysseus myth and how sometimes you must tie yourself to the mast and trust your crew to get you out of trouble, but Nolan's retelling focuses on the guilt and loneliness that come with leadership. Odysseus is consumed by guilt, feeling responsible for the deaths of his soldiers, the destruction of Troy, and, finally, for abandoning his family to fight the war. The loneliness comes from the eventual loss of his companions. At every stop along the journey, Odysseus and his crew face natural and supernatural obstacles that whittle them down. Eventually, Odysseus is trapped on an island with Calypso, questioning every choice he has made and feeling responsible for the deaths of everyone who trusted his leadership.

The Isolation of Leadership

As a leader, I have felt that unusual combination of guilt and loneliness. It happens when I enforce policies that keep the project moving forward but often require the team to change direction or make sacrifices. I know leadership often requires making people angry, but the isolation it creates with your team is still a struggle.

Guilt comes when you must make hard choices that directly disrupt the lives of the people you lead.  A budget cut might require staffing cutbacks. A security breach means holding someone accountable. Leaders must take swift, even cruel, actions to keep things moving forward. I do not take pleasure in doing those things, but sometimes I feel a twinge of guilt. Maybe the situation could have been different.

The business world is full of people who lack that kind of self-awareness. To them, people are just data points with no flesh, bone, or feeling to accommodate. Being a servant leader is different. You have to do hard and necessary things while treating others with a measure of dignity.

Lessons in the Wreckage

Sometimes, I am like Odysseus, wandering the office in a fog as I reconcile my emotions and responsibilities. Eventually, the duty to build and support my team breaks through the fog, giving that pile of driftwood real purpose. The pile of metaphorical driftwood is the lessons I have learned that keep me afloat as I attempt to sail the stormy seas of modern tech. Not a bad insight from an ancient epic poem and a summer blockbuster.

 Until next time.


Edward J Wisniowski

Edward J Wisniowski

Ed Wisniowski is a software development veteran. He specializes in improving organization product ownership, helping developers become better artisans, and attempting to scale agile in organizations.
Sugar Grove, IL