Episode 2: “Sancho Panza and the Gig Economy”
There’s a moment early in Don Quixote where the madman convinces his neighbor to come with him on his quest.
The neighbor is a simple farmer. Poor. Uneducated. Works hard, never gets ahead.
And Don Quixote makes him a promise:
“Come with me, and I’ll make you governor of an island.”
The farmer thinks about it for maybe five seconds.
And then he says yes.
He leaves his wife, his kids, his farm - everything - to follow a lunatic into the wilderness.
Because he was promised an island.
This is “Sancho Panza and the Gig Economy.”
Sancho Panza.
That’s the farmer’s name. And he’s one of the greatest characters in all of literature - not because he’s heroic or brilliant, but because he’s us.
He’s the everyman.
He knows Don Quixote is crazy. He’s not delusional like his master. He can see the windmills are windmills, not giants.
But he goes anyway.
Why?
Because Don Quixote promises him an island.
A place where Sancho - poor, illiterate, nobody Sancho - will be governor.
He’ll have power, respect, authority.
All he has to do is follow the madman and endure whatever chaos comes.
Now let me ask you something:
How many jobs have you taken because someone promised you an island?
Not a literal island, obviously. But:
“Work hard here and you’ll make partner.”
“Grind now, equity later.”
“We’re a family here - your loyalty will be rewarded.”
“Disrupt yourself, upskill, adapt - and you’ll thrive in the new economy.”
“Just drive for us nights and weekends - be your own boss, unlimited earning potential.”
We’ve all Sancho Panza.
Following someone else’s quest because we’ve been promised an island.
Let me read you the moment Sancho agrees to go. This is Part 1, Chapter 7:
[Read with intention - Sancho’s voice should feel working-class, practical]
“Don Quixote told him among other things that he ought to be ready to go with him willingly, because at any moment an adventure might occur that might win an island in the twinkling of an eye and leave him governor of it.
On these and the like promises Sancho Panza (for so the labourer was called) left his wife and children and agreed to become squire to his neighbour.”
[Pause]
“On these and the like promises.”
Not a contract. Not a guarantee. Just… promises.
And Sancho leaves everything.
Here’s what happens next in the book:
Sancho follows Don Quixote around Spain. Getting beaten up. Sleeping in fields. Eating whatever they can find.
Watching his master attack windmills and sheep and wineskins.
It’s chaos. It’s humiliating. It’s dangerous.
But Sancho stays.
Because the island is coming.
Any day now.
Don Quixote keeps saying it: “The next adventure, Sancho. The next one will win you your island.”
Sound familiar?
“Just one more quarter of hitting your numbers.”
“Stack your skills, build your personal brand - the breakthrough is coming.”
“The algorithm will favor you eventually if you just keep posting.”
“Drive through the holidays - surge pricing, Sancho! This is when you make it!”
We’re in the gig economy now. All of us.
Even if you have a “real job,” you’re Sancho Panza:
∙ Following someone else’s vision
∙ Enduring the chaos
∙ Taking the beatings
∙ Waiting for the island
And the people promising you the island? The Don Quixotes?
They’re probobly not evil.
They might even believe it themselves.
The startup CEO who promises equity while paying you in pizza and “exposure.”
The influencer guru selling you the course that will “change your life.”
The corporation that says “we’re all in this together” while the C-suite gets bonuses and you get laid off.
They’re all Don Quixote - charging at windmills, convinced they’re fighting giants, dragging you along for the ride.
I’ve talked to over 860 people on my podcast.
You know how many of them are waiting for their island?
Almost all of them.
“Once I get the right credentials…”
“Once my book gets published…”
“Once the algorithm picks me up…”
“Once I save enough to start my own thing…”
“Once, once, once…”
We’re all Sancho. Following the promise. Enduring the grind.
But here’s the question I think the author Cervantes is asking:
What if the island never comes?
Or worse - what if it does, but by the time you get there, you’ve lost everything that mattered?
Now here’s what’s wild about Don Quixote, and why I love it & you all should read it
Sancho actually GETS his island.
I’m not kidding. In Part 2 of the novel, some nobles play an elaborate prank on Don Quixote and Sancho.
They give Sancho a fake “island” (it’s actually just a town) and make him governor as a joke.
And you know what happens?
Sancho is amazing at it.
This illiterate farmer - who everyone assumed was just a foolish sidekick - turns out to be wise, fair, and just.
He makes brilliant decisions. He solves disputes. He governs better than the educated nobles ever did.
The people love him.
[Pause - this is important]
But then - after just a few days - Sancho quits.
He walks away from the island.
Why?
Because he realizes: This isn’t what he actually wanted.
He thought he wanted power, status, recognition. But the job is exhausting, people are constantly demanding things from him, he can’t sleep, he’s miserable.
So he goes back to Don Quixote.
Back to the road.
Back to the chaos.
And he says - and this is one of the most beautiful lines in the whole novel:
[Read this slowly]
“I was not born to be a governor… I’d rather lie under an oak in summer and in winter wrap myself in a sheepskin and be free, than lie under the constraint of government between holland sheets and dress in sables.”
[Let that breathe]
He chose freedom over the island.
So here’s what I can’t stop thinking about:
We’re all chasing islands we don’t actually want.
The corner office we’ll never sit in because we’re always traveling.
The seven-figure exit that leaves us empty and asking “now what?”
The governor position that comes with holland sheets but costs us our freedom.
The “success” that looked so good from a distance but up close is just… constraint.
[Pause]
And meanwhile, we’ve left our families, our health, our actual lives behind.
Like Sancho leaving his wife and kids to follow Don Quixote.
For what?
A promise that might never come, or worse - a promise that comes true and we realize too late we didn’t actually want it.
[Shift - more direct]
The gig economy isn’t just Uber and DoorDash.
It’s all of us, gigging for someone else’s vision.
Waiting for an island that’s either never coming, or coming in a form we won’t even recognize as what we wanted.
Here’s the brilliance the Cervantes understood 400 years ago and still applies today:
The powerful make promises to the powerless.
“Follow me, endure this, and you’ll get your island.”
And most of us - like Sancho - will follow.
Not because we’re stupid.
But because we’re desperate.
Because we’re hopeful.
Because we want to believe that the grind means something.
But Sancho teaches us two things:
First: You might actually be better than the people making you the promises.
That illiterate farmer governed better than the nobles.
Your passion, your insight, your wisdom - it might be more valuable than the credentials of the people gatekeeping you.
Second: When you finally get the island - if you get it - you might realize you never wanted it in the first place.
That what you actually wanted was the freedom you gave up chasing it.
[Pause]
So maybe the question isn’t “How do I get my island?”
Maybe it’s: “Do I even want an island? Or do I want to lie under an oak in summer and wrap myself in a sheepskin in winter and be free?”
[Beat]
Next time: “The Barber’s Basin and the Golden Helmet” - when two people look at the same thing and see completely different realities, who’s right?
