I Travel 365 Days A Year: 5 Bizarre Things You Learn

The typical American flies maybe once or twice a year. Greg averages two round-trip flights a week. In 18 months, he's worn through five suitcases and three laptop bags -- the things just fall apart. He sleeps at home maybe four days a month.

His company sends him traveling around the country, pretty much nonstop. It's the sort of lifestyle we associate with a very specific kind of businessperson that most of us thought went extinct back in the '60s. But as Greg explained to us, life in the jet set isn't all it's cracked up to be.

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5
Everywhere Is Where Everybody Knows Your Name

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Greg installs point-of-sale terminals in restaurants and bars. It doesn't seem like a glamorous "travel the world" kind of job, but Greg's is a unique position: He got this opportunity largely thanks to a reality TV show. We're not going to specify which, other than to say it had something to do with giving restaurants makeovers. He installed his company's equipment in a bar on this show and taught the owner how to use it, and the exposure led to an insane amount of extra work for Greg. And all that travel led to a unique form of paranoia.

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It's called "travelnoia," by no one.

"You're going to Chicago again, Greg?" says the man behind the check-in desk, as soon as he approaches. "So soon, after last month?"

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The intimacy rattles him, as it always does. He doesn't get how these people seem to know him. He'd swear the staff at this airport is different every time. And they find it a hundred times harder to recognize him, right? They deal with thousands of people every day, and he's just one in the crowd. And yet they seem to remember this one nondescript guy and greet him like a friend.

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The guard groping him always maintains eye contact and smiles.

"Glad to see you again," says the flight attendant once he's boarded.

"Welcome to the windy city, Greg," says the pilot, after landing.

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"We all know you," says a homeless woman, once he's out on the road. Ravens gather at her feet, and she throws crumbs to them.

"We have our eyes on you," says a nearby man next. He's wearing a Civil War uniform, and he's slightly transparent. "You'll always be safe, so long as we're watching."

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"Weird. That's not the usual ghost-soldier pedestrian."

OK, maybe it doesn't play out exactly like that, but the point is that it all gets kind of eerie to Greg. Some of these people in the industry see him regularly, but others know him only as the most prolific frequent flier, and still others behind the scenes must hear about him secondhand. The end effect is less like being George Clooney in Up In The Air and more like being Ed Norton in Fight Club -- constantly greeted by grinning strangers who seem to know his every move ...

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4
Life On The Road Means Driving The Dildo Van

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When the install site is far enough away, Greg flies, but when it isn't, he gets behind the wheel of the company vehicle. The van's a garish monstrosity, painted screaming purple and bedecked in '50s pop art. Sprayed on one side are a man and woman kissing. On the hood, it's a woman in a green polka-dot dress, her mouth a stunned O. You don't look at the van and think, "Of course, point-of-sale systems!" You think, "God, I hope my daughter doesn't wind up in that van someday."

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Sometimes when he's stopped at a red light, a pedestrian approaches him. The man (it's always a man) motions for Greg to lower a window. Then he leans his head in and asks, his voice a whisper, "So ... you got any dildos?"

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"Oh, sorry, how rude of me. You got any dildos, please."

It must have something to do with the van's design. Some dildos are purple, Greg concedes, but he still doesn't really understand the mistake. He must have stumbled into a secret underground violet van mobile dildo delivery network. But lacking any of the desired wares, he just rolls the window back up, makes sure the door is locked, and tries his best not to look like the door-to-door dildo-delivery dude.

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Step 1: No goatees.

3
It Really Sucks Being Sick When You Travel, And When You Always Travel, You're Always Getting Sick

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Greg knows about crowded aisles and crying babies, and don't even ask him about airline food. (We didn't ask him about airline food.) He also knows all about travel illnesses. When Greg gets sick, he's usually hundreds of miles from home and in the middle of a 12-plus hour workday. One time, those sniffles lasted three weeks, but he kept telling himself it was a cold. Then one day, while setting up a new system, he collapsed in the restaurant's dining room. They drove him to the hospital in a delivery truck. All throughout the ride, he stayed on the phone with the manager, walking him through further steps of installing the equipment.

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Meanwhile, a healthy you always ends up "going through a tunnel" three minutes
into helping your parents set-up their WiFi.

He had viral tonsillitis on top of the flu, and the doctor ordered bed rest, which for Greg meant "think about how nice it would be to rest in a bed while you're finishing the install at the restaurant." A week and a half later, he was in New York, in a store still under construction. He collapsed again. The tonsillitis was still there, and he'd also caught himself a fresh batch of pneumonia for his trouble. Remember: This isn't a guy experimenting with the limits of the human body for the CDC. He plugs in computers that show little pictures of food.

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Twenty technicians died to reduce the wait for your pumpkin spice latte.

2
You Go Everywhere But See Nothing

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"Oh man, you get to travel for work?" says the average person, on hearing what Greg does. "You must have seen everything!"

Nope. He's been to New York a bunch of times, but he's never seen the Statue of Liberty. He's been to St. Louis a dozen times without approaching the Gateway Arch and Philadelphia repeatedly without seeing the Liberty Bell. Twenty times through San Francisco, he's yet to cross the Golden Gate Bridge. "Basically, if there's a city that has a famous landmark," he says, "and I've been there (and I've been to most of them), I haven't seen it."

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"You're working Seattle! Keep your back to the Needle at all times."

All Greg really sees when he travels is the airport, the rental car place, the hotel, the worksite, and the roads between them. This has led him to the dubious conclusion that every American city looks exactly the same -- there's a skyline, there are streets, there's the downtown area, there's the freeway. It all just blends in.

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"One time, I went to Disneyland ... or maybe it was Newark. There were buildings of some kind."

When he's in the dildo van, he can't drive anywhere besides the assigned locations, according to company rules. And anyway, he just has no energy to, not after pulling a 15-hour workday. When he's not working, he's in the hotel, eating, sleeping, or half-heartedly masturbating.

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1
Your Personal Life Is A Muddy Tornado

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"Personal life?" jokes Greg. "I don't know what that is."

Greg has seen his best friend a handful of times since 2013. He's been in three failed relationships since joining the company. The longest one was with a woman who worked next door to the pizzeria he was servicing. This was hundreds of miles from where he lived. He should have known they were doomed.

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Precious few pizza-themed pornos follow up on the challenges
of long-term relationships.

But he still loves the point-of-sale systems themselves, and he recently had a wonderful conversation about the subject with an old co-worker from an earlier job:

"You know," she said, "I saw this place that's still using a coin till from the '50s."

"It's crazy!" he said. "People just hate change. They think 'POS' stands for 'piece of shit'!"

"And switching to a proper POS removes virtually all non-fraud credit card errors," she said. (We may be taking some artistic license here, and with all the dialog in this article.)

"That's so true. Not to mention cutting out employee theft!"

"So," she said. "Are you seeing anyone?"

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"Like a therapist? I'm never in one place long enough to ... oh, you mean ... Oh."
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In April, he flew in from a job in Minneapolis and went to sleep in their apartment. At 5 a.m., she shook him awake, repeating something he couldn't understand. "Proposed," she said. "You -- proposed. Wait, no. It was a dream."

"Go back to sleep," he said. Then, at 9 a.m., he retrieved the ring he'd bought two months ago, got down on one knee, and woke her up.

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"Shhhh. If they find out I drove the dildo mobile to Zales, I'm fired."

His exact words were, "I do, in fact, want to wake up with you every morning." That'll be a tall order, since that very night, he was off on a flight to Georgia. But they set a date for next year, determined to make it work. With the amount of time he's out of town, at least they'll never have a chance to get sick of each other.

Ryan Menezes is an editor and interviewer here at Cracked. Follow him on Twitter for bits cut from articles and other stuff no one should see.

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