My worst reporting trip of 2023
Ahead of my first dispatch of the year, a look at 2023's biggest flop.
Warning: this post mentions bizarro sexual comments made by an Uber driver.
Later this week I’ll be embarking on my first reporting trip of 2024. No spoilers, but it’s a weird one. (Not “staying the night in a haunted prison” weird — more like … zany.) And seeing as this is the season for reflecting, I’ve been thinking about last year’s work trips, what I can learn from their highs and their lows.
Which brings me to the lowest low: my most embarrassing reporting trip of 2023.
It was supposed to be a midwest one-two punch. I’d start in St. Louis, Missouri, spending a day shadowing the brave souls who drive the Oscar Mayer Wienermobile full-time (Hotdoggers, they’re called). Then I’d road trip up to Iowa to spend another day at the “world’s biggest” truck stop, Iowa-80. Both assignments focused on people who drive for a living, so I thought a frigid February 250-mile haul of my own might inspire some scene-setting for the stories.
Part one went great. The Hotdoggers — recent college grads full of enthusiasm and deli meat puns — were sweet and accommodating. I worked with a talented photographer and stayed in an odd but cute Airbnb for the night.
Then, disaster.
The morning of my big drive, I got an Uber to the rental car office only to realize I left my driver’s license at the Airbnb — the Airbnb where I already checked out. That meant Ubering back, getting in touch with the owner who was not yet awake, who then had to ask an elderly neighbor to open the apartment for me.
Another Uber back to the rental car spot. The employee-in-training and his manager hovering behind asked for the credit card I used to book the sedan. I did not have it on me; I’d “retired it” for a card with better perks. No problem, they said, we can take another card!
But I didn’t have the other card. I’d lost my Chase Sapphire Preferred and the replacement was in the mail. Would they take Apple Pay? No. Would they take a card over the phone? Also no. Maybe a debit card?
However, I am terrible with money. Don’t tell anybody, especially not Michelle Singletary, but I’ve had a 10-year habit of charging purchases galore and not paying the whole balance every month. I’ve never been in a hole I couldn’t get out of, and don’t make late payments or anything; my credit’s actually great! But I’m not clearing the deck.
That means balances roll over for eternities, racking up the dumbest interest, just lighting money on fire. Because when I want to take a trip, I book the flight regardless of what’s in the bank. When I want to shop at the cutie grocery store in my neighborhood with the best cheeses, I shop there. When I want to send flowers to my friends, I order them. And when I’m lusting for a deeply mediocre $12,234.72 airport sandwich, I buy it. Whoops!!!!!!!!!!!!!!
This YOLO financial philosophy means while I have an abundance of pleasure and joy in my life, I also have no emergency fund. I’m teetering on the edge, baby!! So at crunch time, I — a then-32-years-old, gainfully employed adult — probably had $200 cash to my name. Not enough to cover whatever hold charge the rental car company would need.
I asked the counter guy anyway, hoping Dan could venmo me a loan to cover the difference. But no, many rental car companies won’t take debit cards for reservations even if you do have enough cash in the bank to destroy a car.
Out of options, my eyes started to fill up like the office was slowly sinking under water. The guy and his manager went blurry. I said thanks and left, walking into a nearby hotel lobby to cry for real and figure out how to get to Iowa. What was I going to tell my boss? “Hey, I fucked up and also I have questionable financial habits.”
I looked up every last-minute bus, train and plane option that wouldn’t cost my employer a fortune, and miraculously found a flight for about $100 more than the rental car would have cost.
First I called Dan to weep, then I told my boss. She approved the flight and I rushed to the airport with a face swollen from sobbing.
In transit, I worried I’d have the same problem at the hotel I’d booked in Iowa, so I called and learned indeed they would need to run a physical card. I canceled the reservation and booked a cheap motel instead.
Which leads me to the next big hitch.
Iowa 80 is in a sea of fields roughly 20 miles from downtown Davenport. My motel was only a half mile from Iowa 80; that’s a three minute drive if you have a rental car. I’d have to walk, but there were no sidewalks. Apparently no one had considered a person might travel to the truck stop on foot.
Google Maps recommended a 6.5-mile walk along country roads. My plan had been to document the truck stop from dusk ‘til dawn, so I didn’t want to tromp two hours and 22 minutes on either end in the dark.
With no access to Uber out in the boonies, my alternatives were to hitchhike or make a run for it across the freeway overpass.
So at 7-something-in-the-morning, I waited for the titanic trucks to roar pass in each direction, then sprinted for my life. And 10 hours, a haircut and truck stop shower later, as the sun began to set, I did the same in reverse.
My final penance came the next morning.
No rental car and no Uber made getting to the airport more difficult. I found a taxi service online with worrisome reviews and booked a ride. Would anyone come? I had no idea.
But at 8 a.m. as scheduled, a maroon GMC appeared in the parking lot.
“What time’s your flight?” the driver asked when I got in the car.
“It’s at 10:30.”
“Ok.”
We turned onto the road toward the freeway, then turned again for the parking lot next to the motel with a McDonald’s and Pilot gas station. He pulled into the drive thru, ordered a number 7, and asked if I wanted anything as he was already rolling up his window.
Once he got his food and a caramel macchiato, he started telling me about his romantic escapades, and the friend he had who preferred to date older women for their money. (“What’s that, a gigolo? A Juggalo?”).
He told me about an ex 20 years his senior who tried to hit him with her car while her daughter watched, and cheated on him and loved him too much. He said she was a “porn star” who allegedly had “part of her rectum removed” to accommodate her colleagues whose dicks, he claimed, were the size of the driver’s arm. They were blessed, he said. He accused his ex of faking it in bed with him — how could he make an impact compared to those giant men?
“Why do you think you have problems with your relationships?” I asked against anyone’s better judgement. I was trying to get away from the sexual shortcomings and get back to an earlier comment he made. Plus we had 20 minutes stuck together.
Shoving fries into his mouth, he rambled for a few sentences until the crux revealed itself: his mom played favorites, he said. She loved her other kids more. Having women cheat on him didn’t help. Not that he was setting himself up for success by “leaving them on read — not on purpose, I just don’t want to talk.”
As he launched into another tale of the married woman he was seeing who was trying to trap him (“good pussy though”), I felt nauseous and regretted helping the conversation along. But I offered my best advice: be yourself; be honest about what you want with people from the start, yadayada.
“You’re sharp — are you a therapist? I never talk about this stuff to anyone,” he said.
This is what I get, I figured, for being an impulsive spender, for not knowing about rental car company credit card policies, for talking to sleazy cab drivers, for blowing it. It was my comeuppance for being me.
But 2024 is a clean slate. My new year’s resolution is to be better with money (and also take salsa dancing and French classes, and run a half marathon if my achilles tendons ever heal, and play more tennis, and plan a fantastic wedding, and put The Four Agreements into practice).
To nurture that goal in earnest, I paid off my credit card balances this week by selling a quarter of the few stocks I had (another embarrassing financial move I should keep to myself!!) and have avoided buying some frivolous trinkets I can’t afford. It’s a strong start.
As for that first work trip, you can follow along here.
Safe travels! Love, Nat
Ran across a freeway?!!!!! I was nervous what was going to happen next.
This had me on the edge of my SEAT. So, so relatable (I've accidentally traveled to foreign countries without any cash or means of getting it a few times, not good!!)