The Best Tip to Remember for Business Travelers

My partners and I just completed a two-day marketing trip to the East Coast to meet with prospective investors in New York City and Boston. The meetings went well, however what I want to write about is not the meetings but about some of the travel obstacles we encountered on this particular trip.

I am a very positive person, but when it comes to travel I always have very low expectations. To ease my tension when I travel I like to have as much information about everything  going on around me. If I’m flying I want to know what model of plane I’m on, how fast it’s going, how long the flight is going to be, etc. When taking cabs I want to know if we’re taking the right route, how fast we’re going, and whether or not we’ll encounter traffic on the way. I like knowing all these things because it helps me feel like I’m kind of in control and it calms my nerves. Ironically, one of the key aspects I love about my profession is the work that comes along with trying to figure out the unknowns and push through the unexpected. It’s both exciting and challenging at the same time.

To start our trip we planned to fly to New York City a day early, attend our meetings the following day and take a commuter flight to Boston later that evening. A commuter flight is a flight that makes the same (usually short) flight between two cities numerous times a day. It is most often taken by business travelers who will leave from one city, fly to and work in another city, and be back home for dinner that same day.

We were scheduled to be on the 5pm commuter flight from NYC and arrive in Boston around 6ish. Well, that didn’t happen. Almost immediately after our morning meeting in NYC concluded we received a text alert from the airline that our flight was cancelled. We were told it was because there was a massive thunderstorm in the area and they grounded several of the planes headed to Boston from LaGuardia Airport. This struck me as a bit odd because we were in Lower Manhattan right across the street from the Freedom Tower and there wasn’t a cloud in the sky.

The airline gave us the option to either accept the new flight times we were given or choose from a list of other available flights. Of course, the new flight times were terrible so we called the airline directly to see if there were any other options. There were a handful of earlier flights available, but those seats were filling up fast. After going back and forth over the phone with the airline agent, each of us was able to get rescheduled but on a different flights. But that now meant we had to hustle like crazy out of Lower Manhattan to get to the airport with less than two hours to spare before departure! To make things harder, we didn’t have our bags with us so we had to go back to the hotel (which was not on the way to the airport) and pray that traffic wasn’t too bad on the way there.

Traffic in New York is a disaster. Every time I visit New York it seems like every other street is under construction and no matter where you go (at any time of day) there is bumper to bumper traffic. Have you ever tried to make a right turn in NYC? If so, you know that you have to wait for almost a full minute for all the pedestrians to walk by first, which just makes the traffic even worse. It seems impossible. I feel sorry for all of the emergency vehicles that need to get through traffic and can’t because there is literally no path through. On one part of this trip I was sitting in the back seat of a cab and there was an ambulance right behind me, sirens blazing, probably with a sick patient in transport, just sitting there stuck in traffic waiting on the light to turn green. God forbid there was somewhere in there that needed to get to the hospital!

When we arrived at the hotel I stayed in the cab and asked the cab driver to wait while my colleagues went inside and picked up their luggage. I actually had to take a later flight out of NYC because it was the only remaining flight available. However, by taking a later flight it allowed us to keep one member of the team in NYC for one remaining meeting that afternoon that we otherwise would have had to cancel.

As I watched my colleagues drive off to the airport I took my suit coat off and went back into the hotel lobby to regroup and figure out where the next meeting was. Fortunately, the meeting location wasn’t very far from the hotel, but it was so hot and humid outside that I decided to request an Uber. I don’t know what was happening with all the Uber drivers in that area, but none of the several drivers I requested could ever find where I was located after I submitted the pickup request. After walking repeatedly back and forth up and down Broadway between 52nd and 54th street talking on the phone with Uber drivers to tell them where I was, I decided to give up on Uber and retreat into a small pizza shop just to get some relief from the heat. I wasn’t particularly hungry, but I ordered a personal pizza hoping they wouldn’t throw me out of the place for loitering.

I found a picture online of the restaurant and the exact margherita pizza I ordered. Weird!

After inhaling the pizza I went outside and hailed a cab. I just want to say Thank You to all the New York City cab drivers for being everywhere, all the time, despite the constant competition from all of the on-demand, ride-hailing companies that have flooded the market! I get in the cab and realize that I have about 30 minutes to get to the meeting.  About halfway through the cab ride it starts pouring rain unlike anything I’ve ever seen in New York. I didn’t have an umbrella, so I was hoping I wouldn’t get soaked when I got out of the cab. I did get a little wet but luckily I had about 15 minutes to dry off before the meeting started.

The meeting went well and once it was over I checked my phone to see if my colleagues had made their flight. There was just one text message that read “We’re still at the airport. You may want to take the train (to Boston). Our (3pm) flight is delayed to 5:20pm for now and the 4pm, 5pm, and 6pm flights are cancelled.” I was actually scheduled to be on an 8pm flight, but we all thought that as the weather worsened the 8pm flight was probably going to be cancelled too.

After weighing the pros and cons, I decided to risk it and head to the airport anyway thinking that surely the weather would clear up in the next four hours and the 8pm would fly out as scheduled. It was still raining pretty hard and nearly every cab that drove by was filled with passengers. So, reluctantly, I pulled out my phone and decided to try Uber again. I had forgotten that when it’s raining outside the demand for Uber skyrockets and what normally would have been a $40 trip to LaGuardia now costed $120 bucks! There was no way I was paying that price so I decided to wait to see if the rain would subside and to see if the Uber’s surge pricing would recede to normal levels. They didn’t.

Seeing those crazy Uber prices made me rethink going to airport so I switched gears and started looking at train tickets to Boston. Luckily, I was right next door to Grand Central Station so I went down there to buy a ticket. When I got down there the ticket agent told me that if I wanted to get to Boston I needed to go to Penn Station which was about a mile away. On any other day, I would have walked, but because it was still raining I was forced to take a cab. Upon exiting Grand Central I found an empty cab in front of a nearby hotel and proceeded to Penn Station.

Maybe it was because of the gloomy weather, but the cab driver was yelling and screaming about the traffic for the entire 30-minute journey (Yes – it took 30 minutes to go one mile). At one point I asked him to calm down because I had already purchased my ticket online and had plenty of time to make my train. He replied and told me that he’s usually always frustrated by the traffic and I suggested he find a new career or get over it. It’s New York City – the traffic is always bad!

I arrived at Penn Station around 4pm and the train was scheduled to leave at 5:05pm. While sitting in the waiting area I received a phone call from the airline that my 8pm flight was officially cancelled, and they were putting me on a 1pm flight the following next day. I respectfully declined that option. The train didn’t arrive until almost 5:30pm, I’m assuming because of the weather. After waiting in the queue, I boarded the train and settled in for what was supposed to be a 3 hour and 55 minute trip to Boston.

The train to Boston was completely sold out (likely because of flight cancellations) and everyone was jockeying for seats. Luckily, this was an express train that had very few stops and would put me in Boston nearly around the same time as the 8pm flight would have. As the train slowly creeped out of the station I started to regain hope that maybe, just maybe, I would get to Boston in time to unwind in my hotel room for a couple of hours and prepare for the meetings we had the next day. Unfortunately, due to unusual quantity of rain many of the signals along the tracks were malfunctioning and the conductor had to stop several times while repairmen corrected the issues. This added an additional two hours to what was already a four-hour trip.

On the bright side, the train was very relaxing. It’s well lit, quiet, smooth, and the train crew and passengers were quite pleasant. The conductor provided constant updates about what was happening with the delays and for me, having more information about what is happening always makes the journey easier.

It was about 11pm when the train pulled into Boston. It was raining throughout the entire trip to Boston and it was still raining when we arrived. On the way to Boston I had decided I was going to walk to my hotel from the train station because it was only about a third of a mile away (if that). I reasoned that it’d be easier to buy an umbrella and walk as opposed to waiting in the long queue of Uber riders that had assembled at the train station exit sheltering from the rain.

I went into a nearby CVS (the only store open at the train station at that hour) to buy an umbrella and luckily for me they were sold out. In my head I was yelling “Are you kidding me?!?!” Now I was forced to summon an Uber because I didn’t want to get drenched walking to the hotel in the rain. Ten minutes later the Uber shows up. I hopped in, got to the hotel, brushed my teeth, texted my wife to let her know I made it, and got to bed just before midnight.

I wanted to share this story because I think that most people who travel for business can relate to it in one form or another and it helps to keep a positive mindset. Despite all the issues, there were several positives about this trip. I’ve never taken the train from NYC to Boston and despite the rain, it was a beautiful ride. Being stuck on that train for six hours allowed me to get a lot of meeting prep done and I met a couple of really interesting people. Similarly, the plane ride back home was quite smooth. Neither the captain nor the crew said much during the flight which allowed me to write this blog post uninterrupted. Tip: I’m convinced that learning how to embrace challenges with a positive attitude helps us to grow both personally and professionally. On to the next trip! Cheers – KM

Photo by Olu Eletu on Unsplash

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