Does It Pay to Be Ambiguous?

How to Confound Your Adversaries While Redefining Yourself

There’s a strange power that comes from being unpredictable, like showing up to a funeral in yellow, or meditating in a nightclub.

It’s not about being rebellious for rebellion’s sake. It’s about staying slippery in a world hellbent on pinning you down.

Whether your “enemy” is a toxic boss, algorithmic conformity, emotional burnout, an inner critic, or the tyrannical ghost of who you used to be, ambiguity is your cloak, your smokescreen, your secret weapon.

Let me say it plain…..

….if they can’t read your next move, they can’t control you.

We live in a time where identity is currency as well as a cage. There’s a market for every brand of human being: the wellness guru, the startup bro, the activist, the empath, the disruptor, the sage on Instagram. You find your lane, you stay in it, and God forbid you zig when the world expects a zag.

But I say, swerve baby swerve

Zhuangzi, that wild cuckoo Taoist sage with a grin full of riddles, reminds us that the “usefulness of a cup is in its emptiness.” Translation? It’s the space you leave undefined, unshaped, and unknown that becomes your greatest utility. When you’re predictable, your enemies—internal and external—can game you like a tired algorithm. When you’re mysterious, you become ungovernable.

Zhuangzi once dreamt he was a butterfly. Or maybe the butterfly dreamt it was him. Either way, he obliterated the border between categories. That’s the gift of ambiguity, namely, it shreds the map. It lets you shape-shift. You become both wave and particle. Nobody knows if you’re mourning or dancing. Plotting revenge or plotting a novel. That’s your power.

Wang Bi, the wunderkind Confucian-turned-Taoist philosopher, built an entire system of metaphysical juju on the idea of wu—nonbeing. He said it’s not the things themselves that shape reality, but the spaces between. The unseen logic. The reversal. If that sounds cryptic, good. It should.

Because sometimes the best way to win a game is to walk off the board. Or flip it. Or turn it into a hat.

In times like these—uncertain, upside down, run through with paradox and surveillance—you don’t want to be a stable, static, indexed entity. You want to be a question mark in a trench coat. You want to dance with ambiguity like it’s your long-lost twin.

Here’s some truth from the Taoist underground: nothing is more threatening to control than someone who won’t play the same role twice.

Shake things up. One week, be the monk. The next, the provocateur. Eat silence for breakfast, then roar at the moon by night. It’s not about being flaky—it’s about being alive. Evolution wasn’t built on sameness. It was built on adaptation, variation, and chaos theory with a side of divine comedy.

The Greek trickster Odysseus knew this. He faked madness, cross-dressed, and devised that big wooden horse stunt that punked an entire city. He didn’t defeat his enemies by brute force. He beat them with unpredictability.

So here’s some of my practical Tao-Greek advice for surviving, thriving, and utterly discombobulating your foes (and yourself):

🥸 Do the opposite. If your habit is to people-please, try being blunt. If you’re the planner, try winging it. Break your own expectations. It resets the nervous system. It sends a shockwave into stale routines.

🥸 Freshen the brand. Yes, you are a brand whether you admit it or not. But instead of locking into a singular narrative, become the remix. Switch aesthetics, tweak your tagline, wear something outrageous. It keeps you agile. And more importantly, it confuses anyone trying to put you in a box.

🥸 Speak in riddles when you’re cornered. This isn’t just poetic—it’s tactical. Clarity can be a trap. Let your intentions breathe in metaphor. Be the river, not the rock. Belt out “The Rapper’s Delight”. They can’t hit what they can’t name.

🥸 Leave room for reversal. Don’t tattoo your beliefs in permanent ink. Life is a flux game. Declare today’s truth with conviction, and be willing to un-declare it tomorrow if new insight emerges. Certainty is brittle. Flexibility is divine.

🥸 Curate mystery. You don’t owe the world full access. Hold something back. Cultivate the sacred unknown. It creates gravity. People chase what they can’t predict.

Ambiguity is not a flaw. It’s a feature of higher awareness. When you flirt with the edges, you stop being a puppet of external scripts. You become the playwright.

Zhuangzi would laugh at the idea of becoming your “best self.” He’d probably say, “Why not be a fish, or a cloud, or a whiff of breeze through a bamboo grove?” His point? You’re not a noun. You’re a verb. A shifting, spinning, dazzling becoming.

So go ahead and confound the expectations. Change your rhythm. Reverse the narrative. Be that beautiful anomaly in a world obsessed with knowing what comes next.

Because the most dangerous thing you can be in a predictable world… is mysterious.

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Diamond Michael Scott

aka The Chocolate Taoist