Sidewalks of Synchronicity

A Taoist’s Love Letter to Chicago and Living With Curiosity

Wanderlust doesn’t always demand a boarding pass. Mine stirs daily. It stirs in the scent of roasted coffee beans escaping a corner café, in the silent poetry of sunlight breaking over a rusty viaduct. It stirs when a stranger offers a story unprompted. What some call “random,” I call sacred—the spiritual breadcrumbs of synchronicity left behind by a mysterious, unseen hand.

My compass? Curiosity. My classroom? The everyday. My spiritual path? Sidewalks and serendipity.

Why Chicago Is My Sacred Geometry

Chicago fuels my curiosity like no other place I’ve known. It isn’t just a city—it’s a cipher. Every block, every mural, every overheard conversation on the “L” offers a thread to pull.

The city invites me to investigate the world, and by extension, the human soul. I’ve walked neighborhoods like Bronzeville and Logan Square not to “sightsee,” but to feel. I let the city’s rhythm attune me to my own inner flow.

Chicago’s complexity mirrors the mechanisms of the universe. Its crumbling factories and glittering high-rises co-exist just like Taoism’s yin and yang—opposite forces that don’t cancel, but complement. It’s all part of the dance. The city teaches me, again and again, that chaos and harmony are never far apart.

Theophrastus, Peripatetic Wisdom & Wandering as Philosophy

In this daily walkabout of ideas, I’ve found kinship with the Peripatetic School—Aristotle’s crew of wandering thinkers. But it’s Theophrastus, Aristotle’s student and the father of botany, who resonates most. He wasn’t just cataloging flora; he was paying attention to how things grow. My version of that? I observe how thoughts, people, places, and memories bloom across the gridlines of a city.

Like Theophrastus, I believe the world reveals itself through patterns. Whether in the migration of birds or the migration of people, curiosity is the act of naming what otherwise might remain invisible.

A Polymath’s Playground

My mind isn’t linear—it’s polymathic. One curiosity leads to five more. I might begin the day reflecting on Zhuangzi’s butterfly dream and end it researching the psychological effects of midwestern skylines.

These rabbit holes feed my writing in The Daily Chocolate Taoist, where I weave together the spiritual and the sensorial, the poetic and the pragmatic, all in the spirit of one simple motto: “Stay curious, stay connected.”

Rather than curse the endless stream of interests that tug at my mind, I embrace it. Curiosity isn't a distraction—it’s design.

The Tao of Curiosity

What anchors me amid this kaleidoscope of thoughts and themes is Taoism. It reminds me that life isn’t meant to be figured out—it’s meant to be felt. Lao Tzu says, “The Tao that can be told is not the eternal Tao.” And yet, I try, daily, to catch glimpses of that unspeakable Way in the random, the beautiful, and the overlooked.

Taoism teaches that meaning isn’t forced—it emerges. In the cracks of sidewalks. In the cadence of city traffic. In the quiet understanding between two strangers on a train. Through the lens of the Tao, I decode the cultural motifs, symbols, and signs that flicker throughout the day like spiritual Morse code.

In the End, I Walk to Remember

So I keep walking. Through neighborhoods and histories. Through ideas and cultures. Through the looping soundtrack of a polymathic mind. I trust that the deeper I wander, the more I uncover—not just about the world, but about myself.

Because sometimes, the Tao isn’t in the mountaintop or the monastery.

Sometimes, it’s on Milwaukee Avenue. Or Sherman Avenue in Evanston.

Under a neon sign.

With a pencil.

And a question.

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