Chicago: A Dark Soul at Peace

I found Chicago on an impossibly sunny winter weekend, right on the cusp of spring. Since I’d first heard of

I found Chicago on an impossibly sunny winter weekend, right on the cusp of spring. Since I’d first heard of the city years ago, I’d felt inexplicably drawn to it; something about its reputation ensnared me, carrying with it a delicious allure of prohibition and bright city lights. Which is why, when I received an email with last minute deals to Chicago, my heart beat before I was able to think. Within ten minutes, an e-ticket was patiently nestled in my inbox.

As my plane descended over Chicago’s night sky, I was captivated by an eerily alien yet enchanting view of perfectly symmetrical, brightly lit city quadrants stretching infinitely into the flat Midwestern terrain. Driving through street after desolate street, I became increasingly enamored by the mixed feelings of unease and admiration that this city ignited within me. A sweet melancholy saturated the thick, inky air. Chicago felt like a dark, tired place, exhausted from years of wear and tear. But, though it was dark, it wasn’t sad. This was a complex darkness, whose layers spoke volumes about its history and really – in a way – radiated Chicago’s uniquely brilliant charm.

I discovered myself in Chicago’s courage to bear its soul for all to see, with little regrets or apologies. Chicago is a city that commands attention. One that is unafraid of progress, and does not allow its somber past to define the brightness of its future. I have yet to see an American city that presents itself with such ruthless tenaciousness and poise. It is my favorite city in the U.S. because it embodies the best of what this country can be: an intricate crochet of historical struggle carefully knitted with yearning for culture, a hunger for change through even the worst of times, and an unabashed persistence to be who it really is.

To say Chicago’s dark, looming architecture is attractive would be a vast understatement.This city is downright sexy, and laden with architectural gems. The famous Wrigley and neo-gothic Tribune Tower paint shapely silhouettes across the iconic Chicago skyline, rivaled only by the bold, black skyscrapers that are plotted throughout the city. My absolute favorite was 300 S. Wacker Drive: an otherwise forgettable modernist building that was rendered remarkable by a 400 feet tall mural map of the Chicago River and a playful pop of a bright red rectangle etched onto its black façade. Other powerful structures include the undulating exterior of the Aqua building, two matching towers that resembled honeycombs, and Gothic-style churches plucked right out of Western Europe. The Chicago River, marbled and slinky like reptile skin, slithers its way around these impressive works of modern architecture.

What I admired most about Chicago was its ability to rebuild itself so magnificently after being completely incinerated to the ground in the Great Chicago Fire of 1871. The fire irreparably obliterated roughly 3.3 square miles of the city, killing 300 people and leaving over 100,000 homeless. The Chicago Water Tower, one of the few architectural survivors located along the Magnificent Mile shopping district, is the ultimate symbol of the city’s endurance through one of the largest U.S. disasters of the 19th century. After this traumatic accident, Chicago was left with the option to either surrender itself to circumstance, or rebuild. Luckily for all of us, Chicago chose the latter, gracefully rising from its ashes like a Phoenix. The city reconstructed itself so well after the great fire that it quickly earned the title of America’s architecture capital. I found solace and solidarity in Chicago’s ability to leverage a misfortune to become not just better, but extraordinary.

Chicago is a city of reflections, whose architecture is harmoniously arranged to mirror its dark, beautiful soul. This soul houses a powerful mélange of grit, resilience, and perseverance. The city reminded me of a reformed bad boy, who decided to break free from the chains of his dark, tough past and instead channel his struggles to become a man, strong and respected. I’d like to think that it is no coincidence that in this metamorphosis, the city has armored itself with metallic buildings whose façades reflect one another like a phalanx of shields. Just as we must face ourselves in the mirror every time the sun rises, Chicago’s infrastructure seems to serve as a consistent reminder of what the city has become and what its people have built for themselves.



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Perhaps the most symbolic of these reflections comes from Cloud Gate (famously known as “The Bean”), a 100-ton elliptical sculpture reminiscent of liquid mercury. The highly polished stainless steel splendidly reflects the city’s stunning skyline, rendering it difficult to decide which is more beautiful: the reflection or reality. Unlike its outer shell, the sculpture’s underbelly creates layers of optical illusions, twisting and misshaping the image of anyone who walks through it. I found this to be a poetic ode to the city’s persona, which on the surface appears curated and polished – albeit slightly warped – yet internally is multifaceted and consistently mutating.

Chicago is composed of an eccentric palette of hues and colors. I’ve never experienced a city that was paradoxically bright in its darkness, yet I instantly identified with it. Everything about Chicago’s aesthetic should feel gothic and gloomy, but somehow, the city has leveraged this darkness to paint a masterpiece whose beauty transcends expectations. Chicago’s unconventional use of bold shades gave it a brilliant intensity, from the singular vermillion building contrasted against its black counterparts to the shiny steel skyscrapers lapping sunlight into the streets. The brightest light shines on the beloved Millennium Park, where rows of crisp silver towers encase the area like a metallic ribcage of the city’s heart.

Chicago embraces the darkness that resides within all of us. I understand it, because I myself bear this darkness. Chicago is testimony to the invalidity of the social assumption that equates dark to bad and light to good. Chicago reminded me that it’s okay to be dark without being bad. In fact, it further defined for me just the sort of beauty and delicateness that darkness can embody. It is a darkness not rooted in negativity, but rather in resolution and a proud reconciliation of everything we’ve had to overcome to bring us to where we are. Our past, the darkness that we’ve had to face in our existence, can be the primary driver in our strive towards betterment and change. Without this stark contrast, our virtues could not shine as vibrantly, nor be appreciated as as such.


I'm a self-actualization coach and brand growth expert for CEOs, executives, and leaders. My work has been featured internationally, including Forbes, Entrepreneur, Business Insider, and TEDx. I've helped thousands of visionary leaders worldwide to unlock their most powerful story from within and grow their influence, income, and impact while staying aligned to their true soul's purpose.


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