The Year I Gained Enlightenment By Shaving My Head

Back in the summer of '99, I was living in Chicago, a city known for its deep-dish pizza, oppressive humidity, and a certain transformative energy that seeps into your pores. 

That year was a rollercoaster of self-discovery and radical changes for me. But perhaps the most radical change of all was the day I decided to shave my head.

It all started with lunch. I was sitting at a quaint restaurant, enjoying my meal in the Sears Tower (now the Willis Tower), when a waiter caught my eye. 

He wasn’t particularly handsome, but there was something about him—oh, right, his shaved head. This guy was like a magnet for the ladies; they flocked to him like he was the last pair of Jimmy Choos at a clearance sale. 

They giggled, they flirted, and they left him their numbers on napkins. It was like watching a social experiment unfold, and I was utterly fascinated.

There I was, in the midst of my own existential crisis, trying to make sense of life, love, and the pursuit of happiness, when it hit me. Maybe it wasn’t his charming personality or suave demeanor that got him all that attention. Maybe, just maybe, it was the shaved head. 

That bare, smooth scalp seemed to scream confidence, a certain devil-may-care attitude I sorely lacked at that moment. And thus, in a bold, caffeine-fueled epiphany, I decided I would shave my head.

Now, shaving one's head isn't just about grabbing a razor and going to town. It’s a commitment, a statement. For Buddhist monks, it symbolizes the abandonment of vanity and worldly attachments, a ritual act marking their transition into monastic life. 

It’s all about purification, inner growth, and a nod to the Buddha himself, who renounced his royal past by cutting off his hair. Buddhist monks embrace their baldness as a testament to their spiritual journey.

Taoist monks, on the other hand, are a different breed altogether. They typically keep their hair long, reflecting their connection to natural cycles and the elements. 

Taoism is less about overt renunciation and more about internal cultivation and living in harmony with the Tao, the natural order of the universe. 

Long hair in Taoist tradition I’m told symbolizes fluidity, adaptability, and a subtle, internal focus on spiritual growth.

So, as I stood in my bathroom at home, razor in hand, I wasn’t just cutting off hair—I was making a choice. 

Was I embracing the Buddhist ideal of purification and renunciation? Or was I, in some odd twist, aligning myself with the practical yet profoundly philosophical ideals of Taoism, albeit in reverse? To be honest, I didn’t know, and I didn’t care. I was on a mission.

With each pass of the razor, I felt lighter, freer. Gone were the worries about bad hair days and receding hairlines. I was embracing a new version of myself, one that was bold, unburdened, and perhaps a little bit rebellious. I emerged from that bathroom a new person—or at least a person with a new look.

The next week, I strutted into that same restaurant, newly bald and brimming with confidence. The waiter glanced my way, perhaps recognizing a fellow traveler on the road to self-discovery. And while I didn’t exactly become a magnet for flirtatious women, I did get a few curious looks and a newfound sense of self.

Shaving my head didn’t turn me into a monk, Buddhist or Taoist, but it did teach me something about letting go. It was a small but significant step towards understanding the balance between attachment and freedom, between the worldly and the spiritual. 

And in the grand scheme of things, it was a reminder that sometimes, the boldest changes come from the simplest acts.

In the end, whether you’re shaving your head to renounce vanity like a Buddhist monk or growing it long to embrace natural harmony like a Taoist, the key is to find your own path. 

So here’s to 1999, the year I shaved my head and found a bit of myself in the process. It wasn’t just about the attention or the transformation—it was about the journey, the self-discovery, and the realization that sometimes, the best way to find yourself is to lose a little hair.

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