I landed at Newark Liberty just after nine o’clock. The red-eye had felt endless—flashing cabin lights, the hum of the engine, someone across the aisle clicking relentlessly on his laptop. I didn’t sleep; I watched clouds morph into darkness over the Hudson, then watched the platform lights of the airport grow closer until we touched down. I remember brushing aside the fatigue and reminding myself this was the beginning of something. My first big move: I’d finally joined that startup in New York. Packed a suitcase, left a small-town job behind, and now I was stepping into possibility.
I dragged my roller bag out of the terminal and headed for the shuttle that would get me to the rental car lot. Rain had started—just a light mist—but enough to blur the lights and make the pavement glossy. Under the fluorescent canopy I noticed another person waiting alone: a woman in her late twenties, wearing a leather jacket over a bright yellow dress, umbrella tucked under her arm. She was looking at her phone, head slightly tilted. She glanced up at the shuttle arriving, then back to her screen, then back at the shuttle again. Our eyes met for a split second—I nodded, she offered a shy half-smile.
The shuttle doors opened, and I took a seat near the back. The woman walked down the aisle and sat two rows ahead. I studied her profile: dark hair curled at the ends, lips pressed together like she was thinking something important. I thought about saying something—just an “Are you headed into the city?” or “New rental car line too far,” something casual. But I didn’t. I stayed silent. I knew this moment was opening a door and I didn’t walk through it.
When the shuttle pulled away I felt the weight of that missed connection. A tiny flicker of regret bloomed inside me. What if she was someone who could challenge me, someone I’d bump into again? Or perhaps I’d never see her. I shoved the thought aside, told myself I’d be home before midnight, I’d unpack and crash. New job tomorrow morning. Big meeting. No time for distractions.
The rental car desk was slow. I fumed through the paperwork, watched the minutes tick away. By the time I left the lot the rain was heavier. I zipped down the highway into Manhattan, headlights trailing ahead like fireflies. I reached my tiny Manhattan apartment just after midnight. I unpacked one suitcase, hung my jacket, left the yellow dress outfit in the corner of the bed—not mine—just the image of it. And I slept.
The next morning I stepped into a frenzy. My desk, remote team, Slack messages, design files—everything lived in flow. I dialed in from Boston, had a coffee—ok, there’s the coffee—and tried not to let the anxiety overtake me. I answered questions, offered roadmaps, sent deliverables. All of it felt right. Like I’d stepped into the life I’d been thinking about for years. But scattered across that day, a sense of something unsettled lingered. Not from work. From the airport memory. From the woman in yellow.
By late afternoon I realized I’d never asked her name. Never asked where she was going. Never even gave her my number. I caught myself picture-imagining who she might be. Maybe a fellow creative heading downtown to some gallery. Maybe an urban planner on her way to meeting a client. Maybe someone about to do something bold and I’d let her walk away. The much-talked-about “what if.”
That evening I walked through the West Village after work. Rain had stopped but the sidewalks still glistened. Cars parked slick. Steam rising from manholes. I kept thinking of her, as if she might pop into view behind some corner café. I didn’t stop at any café. I just wandered, letting the streetlights feel like a soft spotlight on the side of the building. It occurred to me that opportunity is often disguised as a small opening—a chance glance, a follow-up conversation, a shared umbrella ride. And when we don’t take it, we’re left carrying the heavier weight of the “could have.”
The next day I was scheduled to present to investors. Big. I rehearsed, paced my tiny living room, rehearsed again. During the ride to the office I reflashed the terminal moment in my mind: the mist, the half-smile, the yellow dress. And I realized something: the missed connection wasn’t only about that woman. It was about a pattern in my life: I see something promising, something vibrant, and I hesitate. I design backup plans and “what ifs” instead of leaning in. And that hesitation turns rich possibility into a quiet regret.
After the presentation—grueling but successful—I escaped to Central Park for a walk. The sun was setting early now, autumn biting at the breeze. I passed joggers, dogs pulling leashes, a couple arguing softly on a bench. And I asked myself: when am I going to stop letting life walk on by while I wait for the “perfect” setup? When am I going to say “hi”? When am I going to risk sounding awkward or being turned down?
By the time I got home I’d decided something. I’d go back to the airport next weekend. I’d sit in the terminal and watch for the yellow dress. Maybe she won’t be there. Maybe someone else will. Maybe I’ll just chat with a stranger and say something like: “You look like you’ve flown many miles—what’s the best layover you’ve ever had?” and see where that takes me. Maybe I’ll just refuse to let that moment slip past unnoticed.
Later that night I journaled. I wrote: “Missed opportunities don’t just vanish. They shadow us. They remind us of the road not taken, the smile not returned, the question not asked. But every day is littered with little doorways. I want to walk through them.”
Two weeks later I found my old boarding pass in the pocket of a jacket. Terminal C, 9:10 pm arrival. I put it in a drawer and promised myself: the next time a glimmer catches my eye, I’ll answer it. I’ll lean in. I’ll ask for the name, offer my own. Because what I don’t want is to look back ten years from now and see a roadmap of “what ifs,” each one a filed-away memory of someone I didn’t say hello to, someone I didn’t sit next to, someone I let drift.
Opportunities will always slip—traveling through airport terminals, crossing paths on subways, chance meetings at gallery openings, on rooftops at sunset. They’re fleeting. But when a door opens, even if it’s just for a moment, leaning into that door might lead you down a corridor you didn’t even dream existed.
So here’s to the next yellow-dressed stranger in the terminal, whoever she is. Here’s to the bold question, the shared umbrella, the “hello, where are you headed tonight?” And here’s to not waiting anymore. Missed opportunities sting less when we acknowledge them and move on—but they sting the most when we ignore them and pretend they don’t matter.
Because in the end, life is made of brief connections. The ones we catch… and the ones we didn’t try to catch. Let’s try.
