The Stressful Skies

Flying is one of the world's most incredible technological feats—a piece of metal that can take you around the world within mere hours!— that, somehow, also creates an equal amount of stress and anxiety.

On a recent trip to New York, Patrick started mulling how he's managed to make that experience slightly less awful: paying his way out of it.

Capitalism!

Patrick: Last week, I pulled off a traveling first, wherein I flew into a city and left that same city in the same day. In this case, it was flying into New York to play a game (more on that soon). Normally, a trip like that would be an excuse to stay overnight and have dinner with a friend, but my wife was flying out the next day, so I needed to be home. The only way to make the math work was being in New York bright and early, which meant spending a loooooong time looking at the booking options for united.com and slowly moving the mouse cursor earlier and earlier. 

The ideal time to leave on a flight is, in my opinion, around 9:00 a.m. O’Hare is about 30 minutes from the house, I rarely fly with a checked bag, and I’ve also got TSA pre-check. That means I can zip to—and through—the airport quickly. I am not a person who likes to spend a lot of time at the airport, so this means I’m usually showing up about 90 minutes before departure, maybe less. Get in, board that plane, and move on with my life. I have never missed a flight!

Crucially, 9:00 a.m. means I could accidentally snooze an alarm and be okay. It means my children would be up and getting ready for school. It creates scenarios where you can accidentally sleep in and still get out the door for the flight, albeit with a little more stress.

That goes out the window once you start moving the time back. In this case, I settled on 7:00 a.m. It gave me plenty of wiggle room in case the flight was delayed a little bit, because even if I landed on time, I’d need about an hour to worm through public transit towards where I was going. If I arrive on time, I can get some lunch and chill. If I’m delayed, I’ve got spare hours.

Once again, I’ve never missed a flight…

Okay there are two asterisks to this claim. One, I was on a work trip and had slightly too much to drink and it caused me to wake up late. I made it in time for the flight…but not in time for my bag to board. Rather than complicate things, I just waited standby for the next flight. Two, I showed up for a flight and realized I had put it in my calendar incorrectly, mixing up CT and PT. I mean, I did miss the flight, but I arrived at the airport at the time I thought I was supposed to?

Anyway, this is distracting from my overall point. A 7:00 a.m. flight stresses me the fuck out. It means I’ll get to my destination on time, but it absolutely ruins my sleep the night before. It gets in my head that I’m going to miss my flight, which means I don’t sleep and stress even more about missing my flight. Even though, asterisks aside, I have not missed a flight! I try to fight this impulse by putting my iPad across the room with its own alarm, meaning I’d have to wake up and walk to the other side of the room to snooze it. By that point, you’d be up and ready to go.

I could have left the night before, but one of the experiments of this travel was trying to drive the price of the trip down. I’ve done versions of this trip before, but the moment you stay at a hotel, the cost goes from hundreds to more than a thousand. It would be less stressful, however.

What are some of your travel strategies? Which ones stress you out the most?

Rob: I basically agree that early flights are terrible… but they're also the ones I tend to prefer. You might get terrible sleep and there's something pretty grim about doing the last of your packing at 445 AM with a car showing up at 5 to take you to the airport, but you also tear the band-aid off. Traffic is usually pretty light, the lines are shorter, and you can usually get a coffee and a sandwich before your flight without too much trouble. The later your flight, the more you are navigating traffic and crowds, which stress me out more.

The thing I basically can't do anymore is the red-eye. In my twenties, it might mean I was exhausted for a half-day before I grabbed some sleep and made a full recovery. Now, if I stack the wear-and-tear of travel on top of a sleepless night (because I cannot sleep on planes at all), it takes me days to dig out of that hole. Maybe it'd be different if I could spring for those fancy "lie flat" seats on inter-continental flights, but I'm not convinced. I'm too keyed-up on a plane and the lack of space to stand up and move around causes everything to stiffen and ache, and nowadays that follows me off the plane and into whatever I'm doing next.

My big travel strategy now is, basically, "just spend more money." Some of this is stuff I would do even when I had way less money to spend as a freelancer. I once booked a room at the Clift hotel in San Francisco on a work trip because I had an event a few blocks away and then a ton of freelance assignments I needed to file. The room cost me as much as one of those assignments paid, but it was worth it for a good desk, internet, bed, and proximity to the other places I needed to be. I filed my last story the next morning before boarding my flight back to Boston, and it was the most I've ever felt like a master business traveler.

The irritating thing now is that the baseline experience is so bad that I've basically surrendered on economizing. I remember back in like 2009, I took a morning coach flight to SF that was half-empty and the attendants let me move to an empty row and sleep on it like a bed for the duration. That would never, ever happen now. If you fly coach, the experience is tuned to inflict maximum physical and psychic damage. You can't "get lucky" with a flight anymore.