Sisyphus & The Boulder

Illustrates Burnout, False Progress, Systemic Loops, Illusion of Effort

In Agile work, teams often feel busy but not productive. They roll initiatives forward, Sprint after Sprint, but still feel stuck. Progress is an illusion. Value remains just out of reach. This parable invites us to ask whether we are pushing the right things, and whether the system itself is keeping us from moving forward.

Sisyphus & The Boulder

Long ago, the gods punished Sisyphus, a clever mortal who had cheated death more than once. His sentence was simple and cruel: push a heavy boulder up a steep mountain. Every time he neared the top, the rock would slip from his grasp and tumble back to the bottom. Day after day, he returned to the base of the mountain, placed his shoulder against the stone, and pushed again. And again. And again.

Some say the gods laughed, thinking this was the worst fate of all: endless labor with no success. But others say that over time, Sisyphus changed. He stopped hoping for the summit. He stopped resisting the fall. He even began to think of the boulder as his own. And so, he kept pushing, not for freedom, not for progress, but because he had come to believe it was the only thing he could do.

Lessons Learned

Not All Motion Is Progress

Sisyphus is active, but he is not advancing. Agile teams can fall into the same trap, mistaking effort for effectiveness. Just because we have daily standups, deliver stories, and close tickets does not mean we are delivering value. Motion is not the same as momentum.

Beware the Loop That Looks Like Growth

The cycle repeats itself. Teams push initiatives that fail to reach the market. They fix defects that arise from rushed decisions. They attend Retrospectives without meaningful change. The system can trap us in a loop. Breaking free requires stepping back to ask: what is the real goal?

When Teams Normalize Futility, Morale Fades

Sisyphus eventually accepts his fate. He stops resisting. This resignation is familiar in organizations where work is driven by compliance instead of curiosity. When people stop believing change is possible, they disengage. Coaching must intervene before effort becomes empty ritual.

The System Shapes the Outcome

The mountain is not optional. The boulder is not light. The gods built the system, and Sisyphus lives within it. Agile coaches help teams see the invisible forces at play: incentives, silos, metrics, culture. To change the outcome, we must change the system.

Rebellion Starts With a Question

What if Sisyphus had stepped aside and asked why? What if he had questioned the purpose of his labor, or recruited others to carry the stone in pieces, or simply walked away? Agile invites us to question the work, the structure, and the beliefs we have accepted as immovable.

Coaching Tips
  • Run a “Boulders & Breakthroughs” Retro: Ask your team, “What are we pushing uphill? What rolls back every time?” This can surface systemic blockers or patterns of repeated failure.
  • Use It To Discuss Burnout: Share the story when a team feels worn down by effort without results. Frame the conversation around impact instead of just output.
  • Expose Hidden Loops: Map out recurring cycles with the team. Where do we expend energy but get no closer to our goals? Look for rituals that have lost meaning.
  • Challenge False Goals: Sometimes teams are working hard toward outcomes that are not even necessary. Use this parable to talk about alignment, value, and vision.

Agile is not about heroic effort. It is about meaningful outcomes. Sisyphus teaches us the cost of mindless repetition, of systems that reward labor over learning. Coaches help teams reclaim their agency, step back from the mountain, and ask the question that changes everything:

Is this the right boulder?