What's Your Worst Work Travel Experience?

I'm on my 3rd week with a new company and they sent over travel expense report templates to be used for the future, I've only known the remote life (graduated school in 2020 so was professionally born into virtual world) but they've mentioned that we will be travelling again at some point.


With that in mind, what's your worst travel experience for work? What was the trip from hell that you went on for your company to sell your heart out

🏰 War Stories
🏙 Corporate Experiences
16
poweredbycaffeine
WR Lieutenant
8
☕️
Traveled with my boss from hell. Too cheap to get his own room, so forced me into booking a double queen (this was somehow not against corporate policy)--he ended up bringing a girl back to our room 2 of the 3 nights (on the 3rd night he got too drunk at a client diner and I poured him into a cab home). I was so fed up that I had to report to upper management. He didn't get fired, and I still don't know how he got out of it.

The second worst was staying out until 3 am in SF with my CSO and had to catch a 7 am flight to LA that morning. Luckily I stopped drinking around 11, but the hangover still persisted due to lack of sleep. I think I drank a gallon of Gatorade while driving around Orange County doing site visits.
funcoupons
WR Officer
12
👑
Sharing a hotel room with your boss is the shit nightmares are made of. 
the_sonk_master
Opinionated
1
Account Manager
holy shit, these are wild hahaha
BillyHoyle
Tycoon
8
Senior Account Executive
I once had to spend every Monday and Tuesday night in Omaha for 3 months. No horror stories, just Omaha on Monday and Tuesday nights.
Enrossie
Opinionated
0
Inside Sales Manager
While not an exciting place there are a couple of good bars and restaurants downtown Omaha. Probably a lot of them closed on Monday night now that I think about it. Epley Field is a very easy airport to get in and out of at least!
the_sonk_master
Opinionated
0
Account Manager
hahaha 😂
InQ5WeTrust
Arsonist
7
No marketing, mayo isn't an MQL
Sharing a double bed with my CEO in a room that had no division with the bathroom just a privacy curtain. 

Too cheap to buy a second room, yet he thought I took a 70 quid Uber and offered to expense it (I took a 4 quid bus).

First job out of college in a 15 person startup. 
saygrace
Valued Contributor
1
Sales Executive
I’m pretty sure that goes against labor laws lol
InQ5WeTrust
Arsonist
1
No marketing, mayo isn't an MQL
Oh I wouldn't be surprised. 
the_sonk_master
Opinionated
0
Account Manager
hahahaha incredible
InQ5WeTrust
Arsonist
2
No marketing, mayo isn't an MQL
He meditated in the morning while I took a shower... so it was all ok. 
nomdeguerre
Executive
6
Account executive
Two stories come to mind:
1. my extremely cheap douche boss made me share an extra smelly airbnb in Chicago for a conference. We had separate rooms but we were there for 4 days and it was so painful that I could never get a break from him.
2. covering sales in the Nordics, I one time did 4 meetings in 4 different countries (Denmark, Sweden, Finland and Norway) in one day - brutal.
the_sonk_master
Opinionated
1
Account Manager
holy shit that is brutal and what a hike that must've been good lord
nomdeguerre
Executive
0
Account executive
Yeah, was pretty brutal. I think I left the house at like 4am in the morning and got back around 2am the following morning... craziness!
LordOfWar
Tycoon
5
Blow it up
Flying all the way to Bangladesh for a field demo which took about 20 hours over the weekend. Sat in the hotel for 2 days waiting for the customer, testing the product, polishing my presentation, etc. 

Meet the customer, they test it and the product breaks immediately with no chance of repair or fix outside of carrying it back to the factory. The next plane home was 5 days later, again over the weekend. Took about 24 hours to get home, economy class both ways.

Boss expected me to be in the office on Monday explaining what happened even though we were in communication the entire time. Lost 2 weekends, a week of work, got jet lag and the stomach flu all because they wouldn't accept they made a sub-par product which with minor costs would have been 1000x better.

They were SHOCKED when I finally quit for a better opportunity with less international travel.
the_sonk_master
Opinionated
1
Account Manager
hahaha oh man, that is bruuuutal
exec
Acclaimed Answer
4
Account Executive
flight from philly to SF... guy in front of me projectile vomits onto the woman's hair sitting in front of him AT TAKEOFF. Meaning, nobody can get out of their seat AND the plane is picking up speed so the dripping fluid is rolling back into my area. 

the guy wasn't hammered or anything so not sure what happened, but they moved us all to different seats, but this was easily the worst thing that's ever happened to me on a flight 
the_sonk_master
Opinionated
1
Account Manager
holy shit this one might take the cake, that's a long ass flight to have that happen too
NateDogg9500
Good Citizen
0
Account Executive
Beautiful 
Enrossie
Opinionated
4
Inside Sales Manager
Had a 1 night trip from Omaha to Albuquerque. Flight was delayed multiple times and meant I arrived after the car rental place was closed. Hotel's booking system was down so they had no idea what rooms were empty. The night manager and I walked in on at least 2 already occupied rooms when he said "There is always one we usually do not rent out because it is located directly above the boiler room and is always very hot". Of course that room's number was "666". It was below freezing outside but I slept for a few hours with all of the windows open because it was so hot.
the_sonk_master
Opinionated
1
Account Manager
this might fit the parameter for "trip from hell" perfectly hahaha
GetAHobby
Arsonist
4
RVP Sales
Traveling with a co worker from Tampa to St Louis, to make a meeting that day and turn right back around and fly home. Somewhere in the state the oxygen bags deploy, we ended up landing in Jax to have the issue looked at. By the time we were let off the plane to look at rebooking there was nothing available, they offered to fly us to St Louis (we missed the meeting) just to jump back on a plane and fly back to Tampa. So we look at flights from Jax to Tampa that day which there were no flights available. So being its only about a 4.5 hour drive I figure we can grab a car. Our company has a policy with Hertz so we went to rent a car to drive it back, the only car available was a Porsche for $400 something a day. I make the call to rent the Porsche rather than taking all the extra flights. All good and we get back into Tampa around 11PM after starting the day at like 4AM to make the flight. Fast forward a few weeks to submitting my expense report and the company keeps rejecting it because of the rental limit I have, I ended up eating $300 from the rental. Never got the meeting and never won the business. 
1nbatopshotfan
Politicker
0
Sales
O god that’s brutal. 
the_sonk_master
Opinionated
0
Account Manager
oh no 😭
sketchysales
Politicker
4
Sales Manager
18 years old, first week in a new job.  Go on a trip with douche bag boss to seem clients.  


Said boss has a personal vendetta against a family member and is shouting to me over the noise of a taking off turbo prop threatening to fire me on my first week unless i do something against that family member (i didnt do it, fortunately someone intervened after).  On top of this the guy has dog breath out of hell.

Then on the return, he suddenly remembers the flight is in half an hour when we are still at the hotel a good 20 minutes away from the airport.  We go back at literally 100 mph.  Barge through security and im legging it for the plane.  He gets pulled at security and misses the flight but i get it (just)  We had kept the plane waiting 15 minutes and im getting on with my shoes and belt in my hand and my seat is at the back.  The walk of shame.  One benefit, peace on the way home.

I get back to the airport, I dont have a mobile phone at this point and I live 2 hours from the airport and a taxi fare starts at around £100 so i dont know what the hell im going to do because i dont know where my boss is, what his number is or how im getting home.  I have literally 3 pound coins with me so i pay phone my mom who phones the bosses wife (on another phone) who phones the boss and finds out that hes on another flight an hour later.

2 hours of more dog shit breath in the back of a taxi. 

man it was bad but i can laugh now.

This believe it or not, is real and actually happened.  I still cant believe it.
the_sonk_master
Opinionated
0
Account Manager
holy shit hahaha
Accidental_Sales_Guy
Politicker
3
Account Executive
Arrived at my hotel at 1am after a day of traveling, and there was no one at the front desk to check me in. My colleagues and I called the hotel company from their desk phone, knocked on "Employee Only" doors, and didn't get a response for over an hour. Finally, some random employee waltzed in from the back and pretended like nothing happened.
the_sonk_master
Opinionated
1
Account Manager
I mean, at least they stayed consistent 😂
saygrace
Valued Contributor
3
Sales Executive
I was traveling from LA to Brunswick, GA missed my early morning flight and had to get on standby, made it to Atlanta, was on standby for the flight to Brunswick, I couldn’t get on the last flight so I was left with 2 choices, either stay a night in Atlanta and miss the important trade show I was supposed to open or drive 4 hours to Brunswick at 9pm at night. I powered up on Red Bull and drove. Made it into my hotel around 1am. Miserable experience considering it was my fault for missing my original flight. I actually have a worse experience that I may share later. It’s just very long and I’ll need to type it up on my computer.
the_sonk_master
Opinionated
0
Account Manager
*grabs popcorn in anticipation for the story of the worse experience*
DadFather
Politicker
3
Enterprise Account Executive
I can’t wait to travel again. The horror stories post covid will be elite 
the_sonk_master
Opinionated
0
Account Manager
☝☝
LostAngeleno33
Old School Bravo
3
VP Sales
Beijing, China. Hotel was 4 miles from the customers office and it took 60+ minutes to get there in a car. On one particular morning we (along with many others) were stuck on an 8 lane highway and jumped out of the car, over the guard wall, ran downstairs and hailed another cab. I was there for 7 days and for 4 of them we were told to not go outside because the pollution was too high. Oh, and the sale didn't close. 
the_sonk_master
Opinionated
0
Account Manager
man this sounds like hell
Madnessandsadness
Good Citizen
2
Strategic Account Manager
In 2019 I was flying from Vancouver to DC for a week trip - big conference and client meetings with my CEO and Director of Content.  Flight lands in Toronto, as there are no direct flights to DC.  Once we land and are half way through our layover (I think it was about 3 hours), we all get the notification that our flight was cancelled - and so was everything else due to a huge thunderstorm.  Nothing flying in or out of New York, DC, Philly etc.

Had a client meeting at 10am the next day, so we rented a car and drove from Toronto to DC and got there at 3am.  We usually go for quite nice dinners - had a reservation at Le Diplomate which we obviously missed - and got McDonalds instead.

The car rental return wasn't 24 hours (we didn't know this) but we left the car there anyways since we had already called an Uber and didn't want to pay for parking at the hotel, so I had to go back in between meetings to drop off the keys and sign the return paperwork.  
the_sonk_master
Opinionated
0
Account Manager
holy hell, nothing more of a metaphorical kick to the balls like getting your connection flight cancelled, mid layover
wheremydawgs
Executive
2
Sr. Enterprise Sales Executive
We had a sales conference in Orlando and I flew in from SF. Meeting at the Marriott was good, private company rented Sea World, and Epcot, balled out. Flight from Orlando to Dallas I got the squirts and wasn't feeling well in Dallas. In the bathroom till flight time. Got on the plane and all hell broke loose, both ends, in the bathroom for 4 hours, finally someone knocks on the door and the stewardess is asking if I'm ok. The call a Nurse, blood pressure is super low, severe dehydration, the Nurse taps my vein while I'm sitting in the bathroom, pants were on. :) Hook me up to heart monitor, heart attack machine to monitor BP. Plane lands and I'm the guy where they hold up the whole plane exiting because the fire dept. comes and wheels me off the plane. Had to call my GF to drive me home, I was f'd up for three days. 
Turns out 70 people got food poisoned. Marriott took no blame said it could have been a virus and didn't even apologize or comp a room, nothing. If I get on a plan that has a blue air freshener I puke in my mouth, scarred for life. 
the_sonk_master
Opinionated
0
Account Manager
holy shit; this is chaotic
Theblob900
Good Citizen
2
Presales Consultant
I flew to Indianapolis, but the job was in Fort Wayne. It was over three hours away, and there wasn't much to see on that trip besides flat farmland and the occasional cow. I bought a razor and barbasol and shaved in the Target bathroom minutes before the meeting and we had horrible subway sandwiches for lunch. The client buidling was so dark, depressing and dated - it was like something out of a Coen brothers movie looking back on it. I only spent two nights, but it felt much longer. 
the_sonk_master
Opinionated
0
Account Manager
hahaha 
TheRealTommyCallahan
Arsonist
2
President of Callahan Auto
Had to go to a Stanley Steemer Convention in Columbus, OH. I have nothing bad to say about Ohio but we went during the Polar Vortex back in 2019. It was so cold. 
the_sonk_master
Opinionated
1
Account Manager
brutal!
TheRealTommyCallahan
Arsonist
0
President of Callahan Auto
Luckily I went to President's club the week after that was in Hawaii. That definitely made up for it haha
Ace
Arsonist
1
CEO
My worst travel experience involves a very bad turbulence. Fortunately, it has nothing to do with sales
the_sonk_master
Opinionated
0
Account Manager
for sure, nothing worse than the split second "oh shit" moment while in the air and hitting turbulence lol
Ace
Arsonist
3
CEO
Ikr, it was so bad that my bloody mary hit the ceiling of the plane and spilled everywhere. Same with the person's coke next to me lol. I will never forget that
the_sonk_master
Opinionated
0
Account Manager
😂😂
Salespreuner
Big Shot
1
Regional Sales Director
Bad road for 300+ kms from an early morning 4 a.m ride
With boss on my side 🙈

And I had a mobile review🤭
the_sonk_master
Opinionated
1
Account Manager
woof that would be brutal, small talk for an hour then "so, how's the pipeline looking??" 😂
Salespreuner
Big Shot
1
Regional Sales Director
My pipe got choked😂🙏
Chep
WR Officer
1
Bitcoin Adoption Specialist
Fellow 2020 grad as well and very ready to start traveling for work and sharing my stories when I do
the_sonk_master
Opinionated
0
Account Manager
for sure, I'm trying my best to get mentally prepared for it all 😂
mcsalesperson1
Politicker
1
Account Executive
Sharing hotel rooms for sales meetings in Holiday Inn Expresses. 
the_sonk_master
Opinionated
0
Account Manager
brutal!
mcsalesperson1
Politicker
0
Account Executive
Happened twice a year and always dreaded it. It was terrible!
BenitoBlanco_
Opinionated
1
Regional Account Executive
Holy shit, just here to say these stories are amazing, this is the content I joined for.
SalesPharaoh
Big Shot
1
Senior Account Executive
Travelled with my bosses and colleagues from hell to another city was an overall shitty experience a lot of work during Ramadan the guy was not a muslim and didn't care, the team expected me to understand what the hell i was supposed to do even though i was newely hired.
the_sonk_master
Opinionated
1
Account Manager
literally thrown to the wolves, brutal
AinslieStreet
Politicker
1
Sales Consultant
Spending two weeks per year in Akron, OH. I don’t think I need to say more.
the_sonk_master
Opinionated
1
Account Manager
been to Akron, can confirm it is from hell
TheHypnotist
Executive
1
Sales Manager
I foolishly agreed to share a room with another rep. This guy probably weighed at least 330 lbs (150 kg). I asked him if he snored, he said "just a little".
That night I experienced first hand the snoring that I later learned was capable of waking up his DEAF daughter whilst she slept in the room BESIDE his room in their home. The vibrations of his snoring were able to wake her up.
Since then I always take ear plugs with me. I don't share rooms any more but I go prepared incase someone like him is in the room next to mine in whatever hotel I am staying in.
the_sonk_master
Opinionated
1
Account Manager
Had a teammate in college who would make the room shake when he slept from the snoring; arguably nothing worse than that
QuesoBlanco
Opinionated
1
Enterprise Account Executive
Mine was totally self inflicted. It was in 2005 when I was still a young one. I was lucky enough to get tickets to opening day at Fenway against the Yankees. It also was the day they received their world series rings after their 86 year drought. Was a day game so needless to say there was a lot alcohol drank over a LONG period of time. Had a 6:00 AM flight to Phoenix the next day for a conference. Went straight from airport to the conference center to go work our booth in the exhibit hall. Walked in and my boss took one luck at me and was like you need to go to the hotel and pull yourself together as you look like a disaster. It also was typical Phoenix heat outside which didn't help. I went back to room and showered, took a nap, and pulled myself together. Rest of the trip went fine but the first 10-12 hours were rough. Was totally worth it though!!!!

the_sonk_master
Opinionated
0
Account Manager
100000000% nothing trumps going to an opening day game, let along at Fenway, against the Yankees and right after the Sox won the World Series
Allisce
Tycoon
1
Account Executive
my boss and I flew seperately. he got in earlier and realized he forgot his corporate card and couldn't get the rental car. Had to cancel our first client meeting the next day while he figured everything out and could get us a car. Luckily I closed them later that year but it was a BAD look. 

Also we were a bit contentious and he decided we could drive from Dallas to Houston. It wasn't as bad as I expected, actual hell,  but it certainly wasn't fun
the_sonk_master
Opinionated
0
Account Manager
oh man, that's bruuuutal
Lumbergh
Politicker
1
Sr Account Exec
East coast to SF flight always sucks, no matter what, but I had 'status' with JetBlue so I picked an exit row seat with more legroom.  I always sit window when I can so that I can rest my head on plastic instead of accidentally on a stranger's shoulder.

Check in and the middle seat is empty on the computer in terminal--many of them are, which bodes well for the hellishly long flight that lands in the same country as it took off in.

Basically everyone is onboard, when I see a [no joke] 6'5 at least guy lumbering down the aisle.  There are fewer and fewer seats, and he stops at my row...somehow he folds himself into the middle seat and even though he is trying, this dude just is way too big to physically exist in the space available.

Super nice guy, he looks and says "sorry I'll try to be as small as possible" - I almost feel worse for him until I find out he's flying free since his aunt is a JetBlue employee and he was a free standby.  

The woman in the aisle seat decides to chat this guy up for the. entire. flight...I'm talking not more than maybe 5 minutes of silence--at first it was kind of adorable since she was 65 and he was probably in his late 30s but we had a decent headwind, so it took 7 hours 22 minutes...after wheels up.  

When I got to the hotel they didn't have my reservation even though I had the confirmation number and I had to go to 2 different sister properties before finding a room.

SF was ok though that trip
the_sonk_master
Opinionated
0
Account Manager
oh man, the talking on the flight was bad enough but the fact the hotel didn't have the reservation is the cherry on top
overheard_sales
Politicker
0
CEO - Overheard_Sales
I had 2 ear infections (a real pain when you only have 2 ears) and got stuck at Newark in a blizzard. Closed the deal tho
the_sonk_master
Opinionated
0
Account Manager
helz yeah
braintank
Politicker
0
Enterprise Account Executive
Realized I left my Mac laptop charger at a client office about an hour away from my hotel. Had a meeting with another client early the next morning. Felt like an action movie to get to the one Apple store in town before it closed in 10 minutes or else I'd f-d.
the_sonk_master
Opinionated
0
Account Manager
hahaha that's awesome
9

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