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The South Indian Monkey Trap is an age-old trick for catching monkeys who raid village food stores. I first learned about it through Robert Pirsig in Zen and the Art of Motorcycle Maintenance.
“The trap consists of a hollowed-out coconut chained to a stake. The coconut has some rice inside which can be grabbed through a small hole. The hole is big enough so that the monkey’s hand can go in, but too small for his fist with rice in it to come out. The monkey reaches in and is suddenly trapped—by nothing more than his own value rigidity. He can’t revalue the rice. He cannot see that freedom without rice is more valuable than capture with it.”
This monkey shares more DNA with us than we’d like to admit. He isn’t choosing rice over freedom, not exactly—he’s choosing this rice over freedom. The rice he found. The rice he earned. The rice he holds.
It’s sunk-cost rice, the most expensive and least valuable rice of them all.
As Pirsig puts it—speaking only of the monkey, of course—“he should somehow try to slow down deliberately and go over ground he has been over before and see if things he thought were important really were important.”
What you want, what you’ve worked for, might be what’s trapping you. The treasure chest you discovered may be the weight that pulls you under.
All you need to do is let go—but you can’t.
Corporate America is littered with rice. Stock options, titles, promotions, that corner office with the nice view. We clutch them like monkeys; fist balled inside the coconut.
Worse, we can’t even eat the rice.
It’s Schrödinger’s rice—we both have it and don’t have it. It’s ours in theory, but our hand is stuck.
Compensation we never cash. Time traded for titles. Rewards that never redeem.
Corporate systems are built on value rigidity—defend the door long enough and you forget it’s an exit as well. And that’s the point. They keep you busy. They want your head down. They want you buried deep in the machinery where you can’t see the horizon, the alternatives.
The equity vests eventually—but by then your dreams can no longer fog a mirror.
Warren Buffett once said, “Working with people you don’t like in business is like marrying for money. It’s probably a bad idea under any circumstance, but it’s crazy if you’re already rich.”
“Rich,” here, is all of us. Most people simply can’t revalue freedom above rice.
Let It Go
“I can get it. I can almost reach it, Dad.”
“Indiana. Indiana. Let it go.”
Even after Indiana Jones saved his father and drank from the cup of everlasting life, he struggled to let it go.
Why?
He wanted that cup in a museum—and he wanted to be the one who put it there. Maybe it was ego. Maybe it was his father’s approval. Maybe it was both.
It’s not just the prize that traps and confuses—it’s the sunk cost. The tests he passed. The time invested. The identity built on the quest.
Leaving it didn’t erase the journey. But he’d have nothing for the trophy case.
Pics or it didn’t happen!
He walked away with his father and friends instead—rich relationships that beat any treasure.
He had to let go. He had to have value elasticity: the ability to reassess worth when the environment changes.
Your money or your life?
The job title, the vesting schedule, the illusion of purpose—they’re all golden chalices in a collapsing cave.
But, I Love My Job!
“We have free snacks!”
“Casual Fridays!”
“My team is like family!”
“Ping pong!”
“Unlimited PTO!”
“We’re changing the world by optimizing ad click-through rates!”
We bond with our corporate captors, defending them online, wearing the company hoodie on weekends, putting the logo in our LinkedIn banner.
Enter Stockholm Syndrome: the corporate mind-meld where hostages bond with their captors out of survival.
Unlimited PTO? Sure—except you work on commission and you’re behind your runline.
No, but really, the coffee is terrific!
Free lunch, free childcare, free laundry. It took years for people to admit the obvious. If the product is free, you’re the product.
After I left my corporate job, people would ask what I did all day. The real answer—reading, writing, coaching my sons’ teams—felt embarrassingly small compared to some high-powered role.
But I had it backwards. The job was small. What I do now is so much bigger.
Still, it feels odd to tell someone, “The kids had a half day, so we baked a cake,” instead of “I was preparing some slides for the board meeting.”
It only feels odd because we’ve been indoctrinated to think this way.
Charlie Munger joked, “I play golf with a man who says, ‘What good is health? You can’t buy money with it.’”
I think I’ve golfed with the same guy, and I’m not taking any career advice from him.
There comes a moment when you realize what you’ve been working on—and working for—is not what you thought. And yet you’ll still be hesitant to leave.
You’ll read books like FISH! or The Energy Bus and think maybe you’re just in a slump. You’ll try like hell to “choose your attitude.” You’ll muddle through. Another quarter, another year, another bonus.
More rice.
The Edge
“I want to stay as close to the edge as I can without going over. Out on the edge you see all kinds of things you can’t see from the center… Big, undreamed-of things—the people on the edge see them first.”
— Player Piano, Kurt Vonnegut
The edge isn’t exile. It’s perspective—the place you can see the game while still choosing how to play. From the edge, you see where you stood yesterday, looking around with clear eyes, and realizing the walls were imagined.
Most people don’t get there. The familiar feels safe. Improvising feels dangerous.
My hope for you? That one morning they’ll wake up and realize you’ve gone. It’ll feel instantaneous, abrupt, but the truth is you’ve been making your way out for a long time.
And the real ones will see why you had to.
“Some birds are not meant to be caged… their songs too sweet and wild. So you let them go… and the place where you live is that much more drab and empty for their departure.”
When Andy crawled through that pipe, no one was waiting on the other side. No promotions. No applause.
Real freedom isn’t going off-grid or quitting in a blaze of glory. It’s quieter. More grounded. More durable.
Freedom is when your identity isn’t hostage to the role you play, when your worth isn’t pegged to what someone else needs from you.
You don’t need permission or applause, you’re not that rigid. It’s value elasticity: the willingness to reprice the rice, the title, the ladder—today, in this environment.
Stay or go—but choose. Open your hand.
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