The Syntax of Self
On language, confidence, and the true self
We learn language the way we learn to breathe: without thinking about it.
First comes the babble, the instinctive reaching toward sound and meaning. Then words. Then sentences. Then, somewhere along the way, the rules arrive. We learn there are right ways and wrong ways to construct a thought, proper forms and improper ones, acceptable arrangements and those that mark us as uneducated, unpolished, other.
What begins as pure expression becomes, over time, an elaborate system of conformity.
This isn’t just about grammar.
It’s about belonging.
I’ve been noticing a spectrum. On one end sits the person who has never internalized the rules at all, who speaks and writes from a place of raw confidence, unbothered by whether their construction is “correct.” On the other end sits the true master, who has so thoroughly absorbed every convention that they can break them deliberately, with precision, knowing exactly which rule they’re bending and why.
Both positions share something essential: freedom.
The vast middle ground is where most of us live. We’ve learned the rules well enough to follow them, but not well enough to transcend them. We construct our sentences, our emails, our presentations, our texts with an invisible audience in mind. Not the person we’re actually speaking to, but the internalized judge who whispers: Is this acceptable? Will they think I’m smart? Will they take me seriously?
This is language in service of survival, not expression.
What I’ve come to understand is that true mastery of any craft, including the craft of communication, involves knowing the rules so intimately that you earn the right to break them. The jazz musician who can improvise has first spent thousands of hours on scales. The poet who shatters syntax has first understood why syntax exists. The leader whose unconventional communication moves people has first grasped what convention was designed to do.
But here’s what makes this interesting: the breakthrough doesn’t come from the mastery itself.
It comes from the confidence underneath.
The musician can improvise not merely because they know the scales, but because they trust their ear. The poet breaks form not because they’ve studied prosody, but because something true is pushing to emerge. The leader speaks plainly, not because they’ve analyzed rhetoric, but because they know who they are and what they’re here to say.
Awareness and confidence meet in that intersection. And from that meeting, authentic expression becomes possible.
I think about how many of us use language to stay small.
We hedge. We over-qualify. We bury our actual point beneath layers of softening phrases designed to make our communication palatable, unthreatening, easy to dismiss. We write the way we think we should write rather than the way we actually think. We speak in the cadence of what’s expected rather than the rhythm that’s ours.
This isn’t a failure of skill. It’s a failure of permission.
Somewhere along the way, we learned that belonging required conformity. That acceptance meant shaping ourselves to fit the container rather than discovering what shape we actually are. Language became the performance of belonging rather than the vehicle for truth.
And so we stay small. Not because we don’t have something to say, but because saying it fully, saying it ouuuur way, feels like TOO great a risk.
What would it mean to speak from the underbelly?
I keep returning to this word: underbelly. It suggests something underneath the surface presentation, something more vulnerable and more vital. The artist knows this place. It’s where play lives, where carefree lives, where the dance happens before the choreography gets imposed.
From a business frame, we ask: What am I saying, and how is it structured as a vehicle to move me toward my goals?
From an artist's frame, we ask: What is authentically arising and wanting to be expressed?
The magic happens when these two questions stop being separate. When language becomes both the vehicle for evolution and the vehicle for expression.
This requires that underbelly of confidence. That settled sense of self that doesn’t need external validation to know its own worth. From that place, language stops being armor and rather becomes an instrument.
I think about the baby learning to speak. No self-consciousness yet. No inner critic evaluating each utterance. Just the pure reaching toward connection, toward meaning, toward being understood.
We spend decades layering rules on top of that original impulse. And then, if we’re lucky, we circle back. Not to ignore the rules, but to play with them. To let language move through us rather than being produced by us.
The question isn’t whether you know the rules.
The question is whether you know yourself well enough to dance with them.
Emergence with Rachel Weissman is a weekly exploration of the interconnections between consciousness, technology, and planetary flourishing.
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