In the early 1600s, Spain was an empire running out of breath—rich in its myths of conquest, short on what it took to sustain them.

And right into that moment rode Don Quixote.

He wasn’t just tilting at windmills. He was acting out a deep confusion that feels familiar to any leader who’s watched an old story lose its power.

Every organization faces a “Quixote moment.”

The moment when the stories that once held things together—growth, control, certainty—start to wobble. When our armor of best practices and KPIs suddenly feels too tight. When the map we’ve been following describes a landscape that’s already gone.

Cervantes gave us a man whose imagination outpaced his era. Quixote’s journey wasn’t about delusion so much as longing—for meaning in a changing world. And when he finally laid down his armor, what he gained was clarity.

That’s the real leadership work: noticing when the old story no longer fits, and staying open long enough for the new one to emerge.

1. Name the myth. What story once made sense for your organization?
2. Notice its cracks. Where is it no longer serving your people or purpose?
3. Invite reinterpretation. Ask, “If this story ended, what might begin?”
4. Hold space for loss. Endings are emotional; name the grief.
5. Author forward. Write the next chapter together—with curiosity, not conquest.

Don Quixote doesn’t end in triumph. It ends in truth. And maybe that’s the transformation we need most.

Taking these steps together creates a path through uncertainty. The point isn’t to replace one rigid story with another, but to find what endures when old certainties fade.

P.S. What story in your leadership might be ready to end—so a truer one can begin?