A picture of Sisyphus toiling away, pushing his boulder up the hill.

The myth of Sisyphus and what it teaches about leadership

Dave Labowitz Leadership

A picture of Sisyphus toiling away, pushing his boulder up the hill.

I’ll get to the leadership lesson in a moment, but first let me tell you a story. According to Greek mythology, Sisyphus was the founder and King of Corinth, a city in south-central Greece. Sisyphus was famed for his cleverness, leading Homer to describe him in the Iliad as “the most cunning of men.” Unfortunately for Sisyphus, he was also a selfish and evil person who deserved everything he got.

Sisyphus was clever

Sisyphus first revealed his character to the world when a notorious horse thief, Autolycus, began stealing cattle from Sisyphus’ herd. While everyone knew Autolycus was a horse thief, no one had been able to prove it because he was able to change the appearance of animals: Stolen white cattle became brown, uniformly colored cattle became spotted, and horned cattle lost their horns. Sisyphus, realizing his herd was steadily shrinking while Autolycus’ was growing, secretly marked the inside of his herd’s hooves with the words “Stolen by Autolycus.” Despite Autolycus’ cattle looking nothing like the ones stolen from Sisyphus, when he lifted the hoof of a stolen cow and revealed the words written there the theft was exposed.

Sisyphus the seducer

Catching the thief red-handed would be enough for most people but Sisyphus was enraged. Determined to seek revenge, he seduced Autolycus’ daughter, Anticleia. Afterward, Anticleia married and gave birth to Odysseus, another Greek famous for cleverness. No one knows if Anticleia’s husband or Sisyphus was his real father but you have to wonder where Odysseus’ intelligence came from!

Prophecy, rape, and murder

Sisyphus’ taste for revenge only grew. He had been born into the royal family of Thessaly but his brother, Salmoneus, took the throne. Sisyphus asked the Oracle at Delphi how he could visit revenge upon his brother and was given a prophecy that if he bore children with Salmoneus’ daughter Tyro (his niece!) that they would grow up to murder their father. Believing the prophecy, he raped and impregnated Tyro. Tyro bore two sons but when she learned of the prophecy she killed them both to prevent them from growing up to murder their grandfather (a proper Greek tragedy!)

Sisyphus’ first death

Sisyphus got himself in trouble with the gods for the first time when got in the middle of a dispute between Zeus and Poseidon. Poseidon’s daughter, Asopus, had disappeared. Knowing that she had been seduced by Zeus, Sisyphus sold this information to Poseidon in return for his creating an eternal freshwater spring in Corinth. When Zeus found out Sisyphus had ratted him out he wasn’t amused. He sent Thanatos, the god of death, after Sisyphus to deal with him permanently.

Somehow, Sisyphus tricked Thanatos into demonstrating how a pair of manacles worked. Once he was shackled, Sisyphus imprisoned Thanatos, knowing that as long as he was captive, no one, including Sisyphus himself, could die. This threw the world balance out of order entirely. With Thanatos trapped, not even those mortally wounded could die. After gruesomely wounded warriors began roaming battlefields, unable to find peace in death, Ares, the god of war, intervened by setting Thanatos free. Sisyphus was once more in death’s grasp.

Sisyphus’ second death

This time, however, he instructed his wife, Merope (one of the Pleiades sisters), to prepare his body without any tribute to Hades or Persephone, the god and goddess of the underworld. She prepared his body without a coin under his tongue which was the required toll for crossing the river Styx into Hades. When Sisyphus reached the shores of the river Styx without Charon the boatman’s toll, he blamed his wife for failing to prepare his body properly. He begged Persephone to release him from the underworld for a few days to correct Merope’s error. When Persephone granted his release, Sisyphus returned to the world of the living with no intention of going back to Hades.

Thanks to their prior run-in, Thanatos wasn’t interested in tangling with Sisyphus again. Without the god of death to collect him, Sisyphus led a long life and ultimately died of old age.

Unfortunately for Sisyphus, Zeus had a long memory. During his life, Sisyphus had crossed Zeus, Poseidon, Thanatos, Hades, and Persephone, not to mention brutalizing countless mortals. When he finally died, Zeus decided to make an example of Sisyphus to serve as a warning to others not to interfere with the gods.

Sisyphus’ punishment

Zeus condemned Sisyphus to a never-ending punishment in Tartarus, the lowest level of Hades. Sisyphus was sentenced to spend eternity wrestling a giant boulder up a steep hill. Each time, just as the boulder was to crest the top of the hill, ending his labor, it would slip from his grasp, crashing and rolling back to the bottom. He would need to climb back down, get behind the boulder, and repeat the struggle of pointless, eternal labor.

The hell of pointless and eternal labor

Great story, Dave. How does all this relate to leadership? Think about the punishment visited upon Sisyphus for a moment. Disregard that it was well-deserved. The key point is that the worst conceivable punishment, even by the king of the gods, was pointless, eternal labor. Think about the soul-crushing impact of this sentence. The real significance of Sisyphus’ punishment is that it makes his life in the underworld meaningless. It steals all purpose from him. There will be no sense of accomplishment. There will be no sense of progress. His spirit is broken. He is forever stuck in a meaningless loop. When you really think about it, it sounds devastatingly awful.

Pointless labor in the workplace

Pointless labor indeed has this kind of impact on people. It’s crushing. And it’s shockingly common for employees to feel that their work has become pointless. It’s very difficult to bring an employee back to a positive mindset once they reach this point. In the meantime, their productivity will drop to almost zero because they no longer see a reason for their work. Their mindset will shift into full-time negativity, and over time, even their self-esteem will suffer. A team member in this position can have a devastating impact on your team’s culture.

As a leader, it’s incumbent on you to make sure your team members feel their work has value and purpose. So how do you do this? And how do you avoid turning your team members into Sisyphus?

Explain the “why”

As Simon Sinek teaches, Start With Why. It’s imperative you explain why the project matters and how your team’s role contributes to the larger picture when you’re assigning tasks. When you give them context, your team members are able to connect fully to their work; they see how it matters and how it’s valuable. Your team will also be able to make better decisions with less oversight when they understand the “why” of their work as these decisions will be made with the big picture in mind. In contrast, if your team doesn’t understand why they’re working on what they’re working on they won’t care much about the outcome.

Check in on their progress and offer feedback

Have you ever had a boss who never seems to review your work at all? It’s discouraging to feel like your work is being fired off into a void, never to be seen or evaluated! How are you supposed to grow as a professional without feedback from your boss? Without growth, it’s easy to feel like you’re caught in an eternal loop at work. Don’t put your team in this situation! Make sure to check in on them periodically and ask to see some of their work. I know you’re busy, and if you trust them it can seem unnecessary. But there is inherent value in letting them know their work matters enough for you to review it and the feedback you offer will be much appreciated.

Celebrate completions

When your team wraps up a big project or crosses a key milestone, take the time to celebrate the accomplishment with them. Completions are highly validating, but only if we take a moment to acknowledge them. Otherwise, your team will simply glide from one project right into the next. This makes work feel like an eternal grind. Stay mindful of completions and you can break the marathon up into shorter, more palatable sprints.

Always find value, especially in failures

It’s easy for your team to feel good about the value created from their successes: Winning is fun. But they’re not going to win all the time. Sometimes things won’t work out, or you may have to pull the plug on a floundering project. Imagine how it feels for a development team to put weeks or even months into building a module that gets scrubbed rather than released! If you’re not careful, an aborted project can make all the work put into it feel worthless. The more work that went in, the worse this can be. The solution is to make sure your team finds learning amidst the disappointment. If you ever have to abort a project that your team has worked hard on, or a project has failed in another way, make sure to do a post-mortem meeting. Discuss what went right, what went wrong, and capture any lessons learned. Acknowledge the hard work that went into the project and tie it to the learning experience rather than the missed target.

Offer gratitude

Be authentic. Tell your team members you’re grateful for them (and why); it will always boost their morale and build connection. Gratitude is a gift you can give your team and it costs nothing at all except your mindfulness. There’s always an opportunity to express gratitude, no matter what is going on. Things going great? Awesome. Be grateful for the hard work that produced excellent results. Things not going so well? So be it. Be grateful for them hanging in there despite the challenges. I guarantee no one was saying “thank you” to Sisyphus. No one cared about all the effort he was putting in rolling his boulder. Don’t let your team feel that way.

Sisyphus’ harsh punishment of an eternity of fruitless labor was well deserved for his life full of evil and trickery. You can accidentally sentence your team to a similar fate if you’re not mindful as a leader. Your team never deserves to feel that their work is worthless or never-ending! Fortunately, it’s easy to prevent. Take a lesson from Sisyphus’ punishment and why it’s so terrible. If you explain “why,” offer feedback, celebrate completions, learn from failures, and offer gratitude freely and liberally, your team will understand the purpose and value of their work and roles.

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