There’s a moment in Don Quixote that no one talks about.
It’s not the windmills.
Not Sancho and his island. Not the barber’s basin.
It’s… stranger than all of that.
Don Quixote finds a cave. A deep, dark cave that supposedly contains ancient secrets.
He asks to be lowered down by rope.
They lower him into the darkness.
He’s down there for about an hour.
When they pull him up, he’s pale. Shaking. Disoriented.
And he tells them an incredible story:
He was in an enchanted palace. For three days. He met legendary knights turned into stone.
He saw magical maidens.
He witnessed impossible wonders.
Sancho says: “Master, you were down there for an hour. Maybe less.”
Don Quixote looks at him, and for the first time in the entire novel… he seems uncertain.
“I know what I saw,” he says.
But his voice wavers.
[Pause]
“God knows the truth.”
[Beat]
This is “The Cave of Montesinos.”
And it’s about what happens when you can’t tell if your vision is real… or if you’re just making it all up.
Let me set this up for you.
This happens in Part 2 of Don Quixote - after he’s already famous, after people have read about his adventures in Part 1.
He’s traveling with Sancho when they meet a guide who tells them about the Cave of Montesinos.
It’s a legendary cave. Deep. Dark.
Supposedly connected to ancient Spanish myths about enchanted knights and magical kingdoms hidden underground.
Don Quixote’s eyes light up.
“I must descend,” he says.
Sancho begs him not to. “Master, this is dangerous. What if the rope breaks? What if there are monsters?”
But Don Quixote insists.
So they tie a rope around him. And they lower him down into the cave.
Into the darkness.
[Pause - let them feel the descent]
Now here’s what you need to understand:
Up until this point in the novel, Don Quixote’s delusions have been external.
He sees windmills and calls them giants. He sees a barber’s basin and calls it a helmet. He sees prostitutes and calls them noble ladies.
We - the readers - can see what’s real and what’s his delusion.
But the cave is different.
Because Don Quixote goes down there alone.
Into the darkness.
And when he comes back up, he tells a story that no one can verify or disprove.
[Shift tone - more direct]
Have you ever had that experience?
Where you saw something, felt something, experienced something so clearly, so vividly…
But you couldn’t prove it to anyone else?
And part of you started wondering: “Did that actually happen? Or did I make it up?”
That’s the cave.
Let me read you what Don Quixote says when they pull him up. Part 2, Chapter 23:
[Read slowly, with wonder and uncertainty]
“Don Quixote asked for something to eat, for he was very hungry. They spread out Sancho’s sackcloth, and seating themselves on the green grass, they ate in peace and good fellowship, and when they had finished lunch,
Don Quixote said:
‘Do not move from here, any of you. Listen, all of you, to what I have to tell you.’
And then he began to relate what he had seen in the Cave of Montesinos, saying:
‘At a depth of some twelve or fourteen fathoms, on the right-hand side, there is a space wide enough to contain a large cart… And in this space I saw a palace built of crystal and precious stones… And there I saw things… things I can barely describe… But I know what I saw. I was there for three days.’”
[Pause]
“But Don Quixote,” someone says, “you were only down there for an hour.”
And Don Quixote responds:
[Read this line with weight]
“That cannot be. I ate there, I slept there, I saw the dawn break three times while I was there. God knows the truth.”
[Let that sit]
“God knows the truth.”
Not “I know the truth.”
God knows.
Because Don Quixote himself isn’t sure anymore.
Okay, let me tell you about my cave.
My cave is the 860 conversations I’ve had.
I go into those conversations - into the darkness of other people’s stories, their struggles, their passions, their unrealized potential.
And I come back up and I tell people:
“I saw something down there. I saw genius. I saw that ember burning in everyone. I saw how the system is rigged against them. I saw how credentialism is gatekeeping. I saw how passion is being crushed by extraction.”
And people look at me and say:
“Are you sure? Or are you just seeing what you want to see?”
And that’s when I start to wonder:
Am I Don Quixote in the cave?
Did I actually see something real? Or did I descend into the darkness with my own expectations, my own biases, my own need to believe in something…
And come back up with a story that sounds true but might just be… fantasy?
[Pause - let that breathe]
Because here’s what’s terrifying about the cave:
There’s no way to know for sure.
When you have a vision - a real, powerful vision of how things could be different, should be different, ARE different if people could just see it -
How do you know if that vision is:
∙ A true perception of hidden reality
∙ OR a beautiful delusion you’ve constructed because reality is unbearable
[Shift - more vulnerable]
Let me give you the specifics of what I think I saw:
Vision #1: Most people have unrealized genius that never gets validated because they lack credentials, connections, or luck.
The doubt: Or am I just being nice?
Maybe most people are actually pretty average and I’m romanticizing them because I want to believe in human potential?
Vision #2: The fight itself - demanding meaning, refusing soul death, tilting at windmills - keeps the spirit alive even when you lose.
The doubt: Or am I just justifying futile resistance? Maybe my friend was right - maybe I’m confusing ambition with delusion, and I’m selling people a story that’ll break them?
Vision #3: There’s something fundamentally corrupt about systems that extract value from people’s labor and passion while denying them dignity and ownership.
The doubt: Or am I just angry because I’m not winning in the system? Maybe it’s sour grapes dressed up as political analysis?
[Pause]
I don’t know.
And that’s what the cave teaches you:
You can’t know. Not for sure.
Don Quixote was down there.
He experienced something. But he can’t prove it to anyone else.
And eventually, even he starts wondering.
Here’s what makes the Cave of
Montesinos different from every other adventure in Don Quixote:
In every other scene, Don Quixote is CERTAIN.
The windmills are giants. The basin is a helmet. Dulcinea is a noble lady.
He never wavers. Never doubts. That’s his madness - absolute certainty in the face of contrary evidence.
But in the cave, for the first time, he’s uncertain.
Later in the novel, someone asks him:
“Don Quixote, did you really see those things in the cave?”
And he says: “I saw what I saw. But… I cannot say for certain if it was real or a dream.”
[Let that land]
That’s not madness.
That’s wisdom.
The recognition that you can have a powerful, transformative experience… and still not be sure if it was real.
[Direct now - this is about the listener]
So let me ask you:
What’s YOUR cave?
What’s the vision you descended into that you can’t quite prove to anyone else?
Maybe it’s:
∙ “I know I’m meant to do something important, even though I can’t explain what or how”
∙ “I saw a way to fix this broken system, but no one with power will listen”
∙ “I experienced something in that relationship/job/moment that changed me, but people say I’m overthinking it”
∙ “I have a calling, but maybe I’m just making it up because I’m scared of being ordinary”
We all have caves.
Moments where we descended into the dark and came back with a vision.
And we’re trying to figure out: Was it real?
[Pause]
Here’s what I’ve learned from 860 conversations:
Almost everyone has descended into a cave and come back with a vision that other people doubt.
The entrepreneur who “just knows” their idea will work - cave vision.
The artist who “has to create” even if no one buys it - cave vision.
The activist who sees injustice others dismiss - cave vision.
The person who quit everything to find meaning - cave vision.
Every single act of creation, courage, or change starts with someone coming out of a cave and saying: “I saw something down there.”
And everyone else saying: “Are you sure? Or did you make it up?”
So here’s the question the Cave of Montesinos asks:
If you can’t prove your vision is real, should you follow it anyway?
Cervantes never tells us if Don Quixote’s vision was real.
But here’s what he DOES show us:
Don Quixote comes out of that cave changed.
More uncertain. More humble.
More aware of the gap between what he experiences and what he can prove.
He stops being quite so certain about everything.
He starts saying “maybe” more.
He starts admitting he doesn’t know.
And that makes him MORE human, not less.
[Shift - this is the insight]
So here’s what I think the cave teaches us:
You’ll never know for sure if your vision is real.
The genius you see in people? Maybe it’s there. Maybe you’re projecting.
The corruption you see in systems? Maybe it’s real. Maybe it’s confirmation bias.
The fight being worth it? Maybe it keeps the soul alive. Maybe it’s just ego.
You. Will. Never. Know. For. Sure.
But here’s the thing:
You still have to choose.
Don Quixote could have said “I’m not sure what I saw, so I’ll ignore it and go back to my old life.”
He didn’t.
He kept questing.
But with less certainty.
With more questions.
With the understanding that his vision might be partly real and partly dream.
And that made him wiser
So here’s where I land:
I don’t know if what I see in those 860 conversations is real.
I don’t know if the ember of genius is actually there or if I’m romanticizing ordinary people because I need to believe in something.
I don’t know if demanding meaning in a meaningless world is noble resistance or dangerous delusion.
I don’t know if I’m Don Quixote seeing enchanted palaces… or just making it all up in the darkness.
But I know this:
The vision matters.
Not because it’s definitely real.
But because choosing to act on it, even with doubt, is what makes us human.
[Pause]
The cave teaches you this:
Certainty is madness.
Doubt is wisdom.
And acting despite the doubt - that’s courage.
Don Quixote descended into the cave certain he’d find wonders.
He came back up… uncertain.
But he kept going.
Not because he knew he was right.
But because the vision - real or imagined - was the only thing worth following.
There’s a line at the end of the Cave of Montesinos chapter that destroys me every time.
After Don Quixote tells his whole story
- the enchanted palace, the three days, the wonders -
someone asks him:
“Don Quixote, do you really believe all that happened?”
And he says:
[Read this slowly, with weight]
“Time will tell.”
[Pause]
Not “yes, I’m certain.”
Not “no, I made it up.”
“Time will tell.”
That’s the answer.
You descend into your cave - your 860 conversations, your calling, your vision of a better world, your unreasonable hope.
You come back up with a story that might be real or might be fantasy.
You can’t prove it.
You can’t even be sure yourself.
But you act on it anyway.
And time will tell if you saw truth… or if you were just in the dark, dreaming.
[Beat]
“God knows the truth,” Don Quixote said.
Maybe that’s all any of us can say about our visions.
I saw something.
I can’t prove it.
But I’m going to follow it anyway.
And time will tell.
