The Day I Tripped on the Subway (And Into a New Client’s Life)

There are days you wake up and you just know. You know today is the day something goes spectacularly wrong. Usually, it’s on a Monday when the world collectively decides to remind you that happiness is a fragile illusion.

So, I had this big meeting lined up—a potential new client, very high-profile, like the kind of high-profile where they probably have their groceries delivered by someone in a tuxedo. If I landed this client, it would be like winning the freelancer lottery. You’d think I’d take extra care getting ready, right? Set five alarms, shine my shoes, maybe sacrifice a small animal to the gods of productivity?

No. I overslept.

By the time I stumbled out the door, my shirt was only half-buttoned, and I was chewing on a granola bar like it was a life preserver. Of course, the subway was packed, because in New York, there’s an unwritten rule that if you’re running late, the entire city must also conspire to ruin your life.

I made it onto the train, and that’s when things went south. Like, really south.

The subway lurched forward, and in some kind of slow-motion horror show, I tripped. My foot caught on something—I swear, a demon subway rat—and I went down. Hard. Now, normally, this would be bad enough. But no. In true New York fashion, I didn’t just trip. I stumbled straight into a woman, knocking her coffee into the air like it was some kind of tragic, caffeinated confetti. The entire car went silent, except for the faint sound of her latte hitting the floor, a $7 casualty.

Me: “Oh my god, I’m so sorry, I—”
Woman: “You’re joking.”

She looked at me like I had just personally insulted her ancestors. Then, as if summoned by fate’s cruel sense of humor, the train jolted again, and my briefcase—because yes, I was trying to look professional today—flew open, scattering papers everywhere.

Me, scrambling to pick them up: “Oh, this is perfect. No, really, couldn’t have planned this better.”

A few people were snickering. Others gave me that pitying look you give to someone who just lost their dignity on public transport. But the woman I spilled coffee on? She was glaring at me, her fancy scarf now decorated with an abstract splash of soy milk and foam. At that point, I was just trying to collect the remains of my dignity, when she says:

Woman: “I hope you’re not in a rush because I’m late to a very important meeting.”

Of course she had an important meeting. New York subway law, subsection 3B: When someone spills your coffee, they must also ruin your entire day.

Me: “Uh, yeah, actually… me too.”

And then, because the universe has a sick sense of humor, she asks: “Who’s your meeting with?”

Here’s the thing. I didn’t want to say. Something told me to just lie. But my brain, already in panic mode, decided to go on autopilot.

Me: “Oh, uh… Jackson & Greene? They’re, uh, potential clients.”

Her eyes widened, and for a moment, I thought, “Okay, maybe I didn’t completely destroy this moment.”

Woman: “No way. I’m Emily Greene.”

And that’s when I realized I had just spilled coffee on my potential new client. Because why not, right? Why not literally trip into the woman who held my future in her very coffee-stained hands?

Later that evening me standing in front of the whole gang at the bar, shaking my head.

Chaz: “Dude. So, did you still go to the meeting?”

Me: “Well, I had two options. I could slink away in shame and cancel the meeting… or I could show up with my head held high, like a guy who doesn’t look like he’s been dragged through the New York City subway system.”

Mark: “And?”

Me: “I showed up. Sat down. Apologized profusely. And you know what she said?”

Tessa: “That it’s a metaphor for how chaotic your business will be?”

Me: “Close. She said, ‘Well, at least you’ve already made a lasting impression.’”

Sophie: “That’s… positive?”

Me: “It’s client-speak for ‘You’re on thin ice, but I’ll throw you a bone.’”

Chaz: “Bro, this is awesome! You just, like, incepted yourself into her memory! Genius.”

Me: “Yeah, because nothing screams professionalism like tripping into your future client’s lap.”

Mark: “At least you didn’t spill anything on her a second time at the meeting.”

I give Mark a flat look.

Me: “You really think I’d make it out without one final disaster? Of course I spilled water during the meeting. Only this time, it went all over myself. A nice, self-contained disaster.”

Tessa: “Well, at least now she knows what to expect.”

Sophie, with a smirk: “Maybe the new brand is ‘chaotic but competent.’”

Me: “That’s the motto of my life. Might as well apply it to work.”

So, lesson learned: if you’re going to make a first impression, go all in. Sure, I might be known as the guy who trips into clients and spills coffee on their designer scarves, but hey—at least I’m memorable.

And if this whole freelancer thing doesn’t work out, maybe I can take up slapstick comedy.

Mark: “You’d be amazing at it. 🤷‍♂️”

Me: “Oh, shut up.”