Work Trip Blunders

I don’t remember too much about my first business trip, but I do remember making a fool out of myself, twice. Once in a funny kind of way that actually earned me some points as the cool new kid on the block who could hang with the boys, and once in a, “what the hell were you thinking you naive child?” kind of way that did just the opposite. A few months after graduating from college I joined the Corporate Strategy and Development department of a financial services firm in New York where I was specifically focused on our firm’s mergers and acquisitions activities. When I joined in 2016 our team was predominantly made up of former Wall Street Investment Bankers. All of them were men. I remember trying hard to fit in and keep up with the sports talk that dominated our area of the office. Baseball was never my forte so I often nodded along, pretending to know way more than I did about the Yankees. I didn’t need to know the exact details of the prior night’s game but I did need to know who won and I did need to know the names of the main players, or at least that’s the standard I tried to hold myself to. When the conversation turned towards our personal experiences with sports I’d always capitalize on the opportunity to chime in with a story of my time as an athlete in college to prove that I could talk the talk. ‘See, I was an athlete. I like sports, just like you,’ I hoped to convey. Whether my sports talk had anything to do with it or not, I was quickly accepted as one of their posse. Over time the pressure to put on the sports prowess cool girl charade wore away but at first it was very much there. 

Just a week before my first day of work, our firm bought another company called MyVest, a Silicon Valley Tech firm whose technology would power our firm’s Robo-advice offering. One of my first assignments was to support the initial integration of this firm into our s, ensuring a smooth handoff from the team that helped execute the deal to the individuals who would be running the business going forward. As part of this hand-off, I helped organize a kick-off meeting in MyVest’s office in San Francisco. It was a nice feel-good session to get everyone aligned and excited about the direction we would be headed in as one unified team. After the meeting we continued the camaraderie we had built during the day over dinner at a nearby restaurant that offered a carefully curated blend of expensive, farm-to-table, chic dining all in one package whose slogan might read, “eat, relax, experience: the simple way”. It was the classic upscale San Francisco restaurant that tried hard to seem like it wasn’t trying hard. Cocktails were ordered all around, followed by wine for the table and a few more rounds of cocktails. I made conversation with the individuals I was sitting near and felt like I was on a roll, coming across as sophisticated yet personable and even holding my own talking business, though fortunately for me this group seemed interested in not talking about work. One woman I met was both a software engineer and a winery owner so we talked about her wine business for much of the night. Another individual was from South Africa and told me all about his recent surfing endeavors there.  

After dinner, a few members of our firm including an individual on my team decided they didn’t want the night to end and that we should grab after dinner drinks at the bar in our hotel, the famed Palace Hotel. At this point I was pretty tired and starting to feel a headache coming on from the four drinks I’d already had, but again, I was young and wanted to prove that I could hang with the boys, so I rallied. When the bartender came around and asked what I wanted to drink I froze. There was no drink menu for me to point to and order some fancy cocktail off of. Wine and beer didn’t seem appropriate because who has wine or beer as an after dinner drink? Nor did my go to simple mixed drink orders of rum and coke or a vodka soda. From the depths of my buzzed brain I tried to beckon the name of a classy cocktail. I knew there was a whisky drink whose name had something to do with New York. I was sure of it.

“I’ll have a Long Island please,” I said with confidence, proud that I’d recalled the drink without too long of a pause. Only, I hadn’t. I’d meant to say a Manhattan and I should have known better because my friends and I used to order Long Islands from Lonski’s, the local bar in our college’s town, and we were not classy in college. 

“Wow, you’re really taking a trip around the bar, aren’t you,” my coworker said.

“Am I?” I asked. I could already feel my cheeks starting to flush. Luckily it was dark in the bar and my face was probably already somewhat flushed from all the other drinks I’d had throughout the night.

“Umm, yeah. I’d say so,” he said.

“Wait, what’s in a Long Island?” I asked, suddenly realizing I must have blundered, but not yet understanding how bad of a blunder we were talking about.

“Well a little bit of everything really. Vodka, tequila, gin, some rum I think. Maybe something else too.”

‘Shit’, I thought to myself, unable to decide whether I was more embarrassed about my drink order or more annoyed that I’d have to drink it and accept the inevitable hangover that would be there to greet me in the morning.

“Oh, I didn’t realize that. Well, I guess I’m in for quite the nightcap.”

“Damn,” he said. “I was hoping you had meant to order that.”

“Maybe not,” I said, “but I’ll finish it.” And I did but it tasted awful, like a mix of seltzer, cough syrup, and straight fire. I drank it so quickly, in part because I wanted to get out of there and go to bed before the alcohol hit me,and in part to just get it over with and get that awful taste out of my mouth. I’ve since learned that Long Islands are supposed to taste good, so not only did I mess up the drink order but I definitely got a messed up drink. I remember feeling the effects of the alcohol come on as soon as we all got up from the bar to head toward the elevator and go to our respective rooms for the night. All I could think was, ‘Just put one foot in front of the other’ and ‘Damn you heels, damn you!’

As soon as I made it to my room I collapsed on the bed and called my brother, Dylan. I probably woke him up but he didn’t seem to mind. That’s who he is, there for me at any hour with no complaints. I told him the story and explained how I either made a massive mistake or turned a mistake into a move that made me seem like a total baller. My words started to slur as the story went on and all the shots in the drink hit me harder. He laughed so hard, and said to me, “Maddie, you’re fine. If someone on my team did that on her first work trip I would be like, damn this girl is cool. She can hang.” And that’s exactly what happened. The next morning my coworkers asked me how I was feeling as we met up in the lobby. I was feeling surprisingly okay. I chugged water and ate a granola bar after getting off the phone with Dylan, per his instructions. It worked wonders! The hangover was minimal. 

“Fine, why?” I asked casually, pretending like the night before was no big deal, putting on my cool girl charade.

“Ughh, I wish I had the liver of a twenty something year old,” my coworker said, shaking his head. 

“I’m impressed,” the other one added.

And so that’s how the first blunder of my first work trip earned me some points along with a good story. The next blunder only earned me a good story and probably lost me any points I’d gained.

The day after the Long Island Incident we had a few meetings, followed by a late afternoon flight from San Francisco to New York that got us into JFK airport just after midnight. The other individuals I was traveling with had ordered cars to the airport via Uber or Lyft but I decided I’d just take a taxi since I didn’t yet have my corporate credit card info in my Uber app and didn’t feel like going through the hassle of adding it right then.

I said goodnight to my coworkers and headed towards the taxi cab line. A big international flight must have recently landed because the line was snaking through the baggage claim area. It looked like what you’d expect to see outside a crowded sporting event or concert. They even had someone standing at the end of the line with a sign indicating how long the wait would be. The sign read, Current wait time: 60 minutes. I looked down at my phone. It was close to 12:30 AM and the last thing I wanted to do was wait an hour and then spend another 45 minutes in a car. When I looked up from my phone, a man approached me wearing an Uber t-shirt. 

“Hi Miss,” he said. “I’m with Uber. Given how long the lines are we have Uber vehicles here waiting, just like a taxi service line but much shorter. Do you want to avoid the line?”

“Yes” I said. This is great. Dealing with the credit card in the Uber app is way better than waiting an hour, I thought. 

“Follow me,” he said, ushering me towards the sliding glass doors that opened to the passenger pickup area. Sure enough there was a queue of black vehicles waiting there. These must be the Ubers, I thought to myself. 

The man grabbed my navy carry-on suitcase, put it in the trunk, and opened the backseat door for me. I hopped in and we were on our way. 

“Where to, miss?” the drive asked. 

“72nd and,” I started to say before he cut me off. 

“No, just which borough,” he asked. 

“Oh, Manhattan,” I said. “Also, don’t I need to plug your info into the app somehow?” I asked pointing to the Uber application I had open on my phone screen. 

“No, it’s fine” he said.

I quickly understood that this was not an Uber and I started to look around for signs of some kind of taxi driver registration but saw none. ‘Great’, I thought to myself. ‘This is how I get kidnaped and die.’

As we drove along I pulled open Google Maps on my phone to make sure we were actually heading towards Manhattan. We were, so that gave me some peace of mind. As soon as we got on the main highway the driver’s phone started to ring and he picked it up and proceeded to carry on a conversation in Spanish. Unfortunately I was never very good at Spanish so I couldn’t make out too much of what he was saying. At one point he stopped his conversation and asked, “Miss, where in Manhattan are you headed?” 

I told him the cross streets of my apartment on the Upper West Side and breathed a sigh of relief. We weren’t out of the woods yet but this was a good sign.

As we approached East Harlem, one of the more crime ridden neighborhoods in Manhattan, my nerves picked up a bit. If this guy were to be kidnapping me this could be a good place to do it, I thought. Then the threat level felt suddenly real as we stopped at a red light and the driver started to roll down his window. Following his gaze, I noticed that he was staring down an empty dark alleyway butting up against a vacant looking graffitied building with boarded up windows and an open doorway. Then his phone rang and he answered it, keeping his eyes fixed on the alley. I gripped my fingers around the door handle, while keeping my eyes fixed in the direction the driver was looking. I was fully prepared to jump out of the car and run if I saw someone come out of that alleyway. I even slid my feet out of my heels because god knows I wouldn’t get far in those ankle breakers. Then the light turned green and the driver put his foot back on the gas. I breathed out, not realizing I had been holding my breath the whole time we were stopped.

As we got closer to my apartment I felt more and more at ease. Okay, everything is fine, I reassured myself as the driver pulled up to the awning in front of my building. But the excitement of the evening hadn’t ended yet. I handed the driver my corporate credit card and he said, “No credit card. Machine is broken. Cash only.”

I opened my wallet, if only to show him that I didn’t have much cash, not to actually check how much cash was there.

“I only have twenty dollars,” I said, pulling out the lone bill. 

“In there, ATM” he said pointing at the bodega on the corner, the one I never shopped at because of the absurd markups.

“You want me to go get cash?” I asked, dumbfounded. 

“Yes. I stay here. No cash, no bag” he said glancing back toward the trunk of the car where we both knew my suitcase and backpack were sitting. 

“Okay, I’ll be right back,” I said uneasily as I hopped out and jogged towards the bodega. I opened the door to the shop, hearing the familiar jingle of bells I always heard when walking by in the daytime. The tired woman behind the counter stopped her game of Solitaire and looked up at me curiously. I suspected that a twenty-something year old woman wearing a gray dress, a blazer, and pumps was not her usual clientele at 1:30 in the morning. I walked up to the ATM and saw a sheet of lined loose leaf paper taped to it that read: Out of Service.

My heart raced. I’m going to have to tell this guy that the ATM machine is broken and he’s not going to believe me, I thought as I walked back toward the car and knocked on the window. The driver rolled it down.

“I swear to god, their ATM is out of service,” I said trying to mask my fear and vulnerability with an aura of annoyed confidence.

“It’s okay,” he said, motioning for me to get back in. “There’s another one around the corner.” 

Why I got back into that car and didn’t just say screw my laptop and suitcase is beyond me, but I did and we drove around the block to a Chase Bank that had a 24/7 ATM. I hopped out and walked to the ATM, my heart racing as I put my debit card into the card slot only to realize that I didn’t know how much the cab fare was. The driver had never told me. Based on prior experience I knew it shouldn’t be more than about 75 dollars, but prior experience wasn’t exactly the best proxy given the experience I’d just had. I took out 150 dollars to be safe. 

I got back in the car and told the driver I had cash and he drove me back to my apartment. 

“How much?” I asked.

“How much did you take out?” he replied, clearly hustling. This is such BS I thought to myself, trying to decide whether to lie or just give him the 150 dollars I’d just taken out. 

“100,” I said, full knowing that was less than I actually had but still well over market.

“120 then,” he said with a smirk, remembering my other twenty dollar bill. 

“Could you give me a receipt?” I asked before handing him the money. I needed a receipt to submit my expenses to work, not that we were supposed to submit reimbursements for cash expenses of that amount.

He fumbled around and grabbed a pen and a piece of paper and wrote on it: Cab Fare: JFK to UWS, $120 

I grabbed this sham of a “receipt” and got out of the car as quickly as I could, slamming the door behind me in pathetic protest. I spent some time over the next week trying to decide whether or not to include the cab fare in my expense report. The main consideration was not whether or not the value of recouping my 120 dollar expense was worth the cost of admitting to my lack of good judgement and street smarts. The individual who reviewed and approved our expenses at work was a hawk. If I didn’t include an expense for my ride home from the airport she would notice and ask me about it. I was sure of it, convinced that she carefully reviewed every receipt and detail of our expense reports. I didn’t want to be forced to admit to being too embarrassed to submit my cab fare, which would in itself be embarrassing, so I opted to send in the copy of the joke of a receipt and wait for questions. I did add a qualifying note that said: receipt machine was broken, hence the paper receipt. This wasn’t completely untrue. The machine that was this guy’s system of handwritten receipts was flawed and therefore broken in a way, I justified to myself. 

To my surprise, no questions ever came. But, I didn’t hide the story from my coworkers. It was too funny and absurd not to share. They definitely thought I was a naive idiot for what I did, and to their credit, I was. But I learned my lesson and I’m way more street smart in the city than I was when I first arrived. And, and this is a big and, no one got hurt so all’s well that ends well I guess. I still haven’t told my mom this story. My dad told me not to.