A Comedy of Errors: My Misadventure in Business Travel
The Setup
The plan was simple: fly in, work hard, fly out. A neat little three-day jaunt into the belly of corporate America, wrapped in efficiency and purpose. But the universe cackled in the background, cracking its knuckles, ready to turn my Type A itinerary into a surrealist performance piece.
At home, the real concerns were less about work and more about whether my absence would cause domestic anarchy. The girls were used to a well-oiled, two-parent household machine. When I told Anna about my impending departure, she blinked, considered, and then casually shrugged, “Oh, I will be sad, but then we will get a new dad.”
Well. That was unsettling. But at least I knew she was resilient.
The Visa Fiasco
A visa, in theory, is a straightforward transaction. You show up, present paperwork, and they give you permission to work in another country for a bit. In practice, my visa process was a Kafkaesque journey into bureaucratic absurdity.I arrived at the airport four hours early, brimming with optimism. Five hours later, I was still there, now a husk of a man, staring vacantly at the fluorescent lights. Meanwhile, the guy ahead of me, who arrived late and clutched a diploma the size of a doorframe, encased in a giant, ornate frame that looked like it belonged above a grand fireplace rather than in an airport security zone, breezed through. Did he know something I didn’t? Was I on a hidden camera show?
I inched forward, dared to ask about my flight. “Oh, don’t worry,” the attendant chirped, “We’ll take care of you. There are plenty of flights.”
There were not.
Eventually, my passport was stamped, my dignity reduced to crumbs, and I was spat out into the cold embrace of Air Canada customer service.
The Air Canada Ordeal
If there’s a corporate hierarchy of entities that break human spirits, Air Canada is in the upper echelons. My itinerary, I was told, was salvageable. This was a lie. Every flight was booked, my options reduced to shrugging employees and the endless purgatory of an airport terminal.I had a morning deadline: 8:00 a.m., a whole agenda that required me to physically exist in an office. My director, unfazed by my plight, insisted I make it work. Eventually, they put me on a flight to Chicago the next day, after working hours [6pm]. Chicago. That was it. No way to Indianapolis and Richmond. No plan. Just “you’re someone else’s problem now.”
The Chicago Detour
The new plan was bleak: work all day, fly to Chicago, then undergo a five-hour rental car pilgrimage to Richmond. But at this point, I had transcended emotion. I was a man of action, fueled by exhaustion and the shattered remains of my faith in humanity.The next morning, still determined to avoid the hellscape of Midwest highway driving, I called Air Canada again. Miraculously, someone competent answered. I was rebooked onto my original Chicago-to-Indianapolis flight. The sheer simplicity of it made me want to weep.
Upon landing in Chicago, I thought, what the hell, let’s try my luck. I strolled up to the check-in desk for an earlier flight and, without fuss, was handed a boarding pass. Was… was this what good customer service felt like? I boarded, smug, victorious. Surely, now, things would go smoothly.
They did not.
The Rental Car Disaster
Indianapolis greeted me with yet another setback: my reserved rental car was an imaginary construct. “No cars available. We’re really sorry.” No other agency would take walk-ins. It was like Seinfeld’s infamous reservation scene—”You know how to take the reservation, you just don’t know how to hold the reservation!” Except I wasn’t laughing.
After futile calls to Expedia, I at least wrestled a $145 refund for my inevitable Uber ride.
The Uber Ride of Doom
It was nearly midnight when my last-ditch Uber arrived. My driver exuded an energy best described as “true crime documentary waiting to happen.” He drove as if auditioning for a role in Fast & Furious: The Indiana Drift, peppering our dark, f-bomb-infused drive with grandiose hand gestures, sweeping declarations about brotherhood, and an unwavering devotion to an America soaked in motor oil and unbound confidence.
I stayed chatty, friendly, dropped subtle mentions of my loving wife and adorable children, the ones who were waiting for me, who would definitely notice if I disappeared. Inside, I was praying. Outside, I was counting the minutes to safety.
When I finally stumbled out of that car, I felt like I had survived a psychological thriller.
The Work and Camaraderie
The actual work? A breeze. My colleagues, whom I had only known in pixelated Zoom squares, were thrilled to learn I was real. We bonded over long hours, exhaustion, and my growing reputation as “the guy who barely made it here alive.” I was starting to feel like some kind of folk hero.
Before I left, I heard that the CIO had wanted to meet me but, alas, schedules didn’t align. Probably for the best—after all, how does one even begin explaining this odyssey?
The Aftermath
Despite everything, the trip was technically a success. I had bested Air Canada, outmaneuvered the rental car gods, and survived an Uber ride that will one day make an excellent therapy anecdote.
Most importantly, when I arrived home, my family was waiting for me, arms open, relieved. I scanned the room quickly—no replacement dads lurking in the shadows. My position remained intact.
Was the trip worth it? Probably not. But did I survive? Barely. And honestly, that’s a win.