The South Indian Monkey Trap
And why we, CEOs, often end up in it.
There’s something about Joan Westenberg’s writing that always gets under my skin — in the best way. It doesn’t just make me think; it makes me notice where I’ve been standing still.
Her recent piece, The Map Is Not the Territory (and It’s Definitely Not Progress), made me confront how much time I spend thinking about doing instead of actually doing. In it, she mentions the South Indian monkey trap from Zen and the Art of Motorcycle Maintenance by Robert M. Pirsig:
You drill a hole in a coconut, put rice inside, and wait. The monkey reaches in, grabs the rice, but then can’t pull its fist back out through the hole. The monkey could escape by letting go of the rice, but it won’t. It’ll sit there, trapped by its own grip, while the hunters approach.
Joan uses this image to describe how we get stuck in analysis — mistaking understanding for progress. She writes that our brains even reward both with the same dopamine hits.
That hit of “I’m working on it” is seductive — and it’s often my trap as a first-time CEO. I can spend hours building strategies inside my head, convincing myself I’ve moved mountains, when in reality, nothing tangible has changed. The illusion of busyness is exhausting.
Can you relate?
What’s Trapping You?
I’ve learned that first-time CEOs don’t get trapped by bad ideas — we get trapped by almost actions. The pitch deck we keep tweaking. The new feature we keep “refining.” The hire we’ll make “once things settle.”
“Understanding is clean and controllable and it happens entirely in your head (where you’re safe.) Action is messy. Action = other people and uncontrollable variables and the possibility of looking stupid. Of course your brain would rather stay in theory mode,” says Joan.
It’s the same monkey trap in a different form. We grip our rice — our plans, our control, our imagined perfection — and wonder why we can’t move forward. But progress doesn’t come from understanding. It comes from release. From trying, testing, risking embarrassment. From stepping into the territory where things are alive, unpredictable, and uncomfortable.
The growth hides in the mess.
For me, that meant finally letting go of my own handful of rice: the need to have every chapter, every interview, every plan perfectly mapped before I started. I stopped waiting for clarity and just began.
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Meanwhile, I’m editing Episode 1 of Season 2 of The First-Time CEO podcast with not one, but two guests! It turned out epic. Stay tuned, it’s coming out next week!
If you’ve been caught in your own version of the monkey trap — stuck planning instead of building — maybe this is your nudge to move. Not when you’re ready. Now.
Three takeaways for first-time CEOs:
Beware of “productive paralysis.” Thinking feels safe — but it’s often a disguise for fear.
Perfection is a trap. You don’t need a better plan; you need a smaller first step.
Momentum creates clarity, not the other way around. Action is the only honest map.
#GoldenFindings on Letting Go, Progress, and Building in Motion
The Map Is Not the Territory (and It’s Definitely Not Progress)
— Joan Westenberg’s piercing essay on how we confuse motion for meaning — and how understanding can masquerade as progress. A reminder that thinking is not doing.
🔗 Read hereInside the Monkey Trap
— Economist Bryan Caplan revisits the parable that inspired so many metaphors for human behavior: how holding on to what we want can be what keeps us stuck.
🔗 Read hereThe Overthinking Trap: How to Stop Planning and Start Living
— Explores how planning can become paralysis and why taking imperfect action often beats perfect preparation.
🔗 Read here
#CEOCheck
What “rice” are you holding onto that’s keeping you from building what really matters?
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