New York Rain, and Reflections on Halloween Eve
- Jenna Ryan

- Oct 29
- 2 min read
Updated: Oct 30

The rain outside taps softly against the window, blurring the New York skyline into a river of lights. I’ve always loved rainy nights; they give this fast-paced city a reason to slow down, even if just for a moment. The air feels fresh, almost as if it’s washing away the day’s restlessness.
Tomorrow is Halloween. Pumpkin lanterns are already peeking out from the storefronts on the corner. Kids are probably buzzing about which superhero or fairytale princess they’ll dress up as. It reminds me of a "mask"—something we all wear as adults, often without realizing it.
During my years on Wall Street, I wore an invisible mask. This mask, made of success, numbers, and society’s expectations, was hard and shiny, but also cold. It isolated me from the warmth of reality. We’re all so good at playing our roles—decisive decision-makers, flawless professionals, tireless leaders. But beneath the mask, does the real us—the one who gets tired, confused, and craves simplicity—still get to breathe?
The most fun part of Halloween is "Trick or Treat." It’s a game, but also a powerful metaphor for life. I used to chase the "candy" that the world handed me—billions of dollars in deals, record-breaking performance stats. The sweetness was always so fleeting, yet irresistible, pushing me to always seek more. But that sweetness never truly nourished my soul.
The true "reward" came when I took off the mask and started being honest with myself. It’s the peace I found in deciding to live not just for numbers and balance sheets, but for people, for beliefs, and for those who need a "new language" to bridge their understanding.
Just now, I had a conversation that left me feeling truly inspired. The sparks of thought were like a long-lost feeling of joy—pure, born from intellectual exchange. That, too, is a kind of "sweetness" that life offers. It even made me laugh—at this moment, realizing I’m still single feels oddly fulfilling. Maybe when you find inner peace and purpose, emotional companionship becomes a beautiful addition, rather than a void you need to fill.
The rain feels like a soft reckoning. It reminds me of what really needs to be "washed away" from our lives. Perhaps it's the labels we wear that no longer serve us, the masks we put on to please others, or the shallow desires that make us lose our way in the noise.
I often say that clarity isn’t about how far you can see in broad daylight. It’s about being able to navigate the path ahead, even in the middle of a storm. True growth is about returning to your authentic self—clearly understanding who you are, why you’re here, and where you’re going. Tomorrow, as children across the city slip into all sorts of costumes and revel in the festivities, I hope we, as adults, can also take a moment to shed our masks. Maybe the real Halloween isn’t about who you dress up as, but about finally being able to stop dressing up altogether.
In this rain-soaked New York, may we all find the courage to live without masks.
Goodnight.



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