Travel Lightly (Premium)

My trip to Seattle for Microsoft Ignite is interesting on a few different levels, but I’m particularly stuck by the unfamiliar travel experience: I had to do things differently to make this trip happen, and it’s been a good reminder of why I’m so particular about travel.

And because I’ve traveled so much, I do everything I can to make what is usually an arduous experience as comfortable and trouble-free as possible. This involves adopting and honing habits over many years, too many flights to count, and a growing amount of time spent outside the United States each year. And while it’s interesting how much has changed since our first international trip 30 years ago, one thing has never changed, and it’s my key takeaway from a life spent on the road: Always travel as lightly as possible.

Long-time readers likely know the basics of my travel experiences. I traveled regularly for work for over 20 years. My family spent three weeks in Europe every summer. When the pandemic changed everything, my wife and I purchased an apartment in Mexico City with the goal of splitting our time between there and the U.S. And I write about these experiences in What I Use articles that, among other things, describe the technology products and services I bring with me for personal and work-related reasons.

But there’s more to it than all that.

For example, you may assume that I enjoy traveling. But I do not: Traveling is a terrible, stressful, physically uncomfortable, tiring, and grueling experience, and the pain starts the moment you start trying to book a trip and lasts until a few days after you’ve returned. What I do enjoy is being in other places, meeting the people there, and experiencing new things. Sadly, one must travel to accomplish that. And so I do. And I hate it.

Flying is the worst part of traveling. It’s an experience that you can’t fully control no matter how much money you have, and it can be unpredictable. Short of an actual plane crash, I’ve pretty much experienced everything that flying has to offer. I’ve sat in the best seats on a plane, and the worst seats. I’ve flown great distances with a lay-flat bed, and great distances in coach seats that weren’t quite wide enough for my hips. My wife and I were on a flight that dropped out of the sky, hurtling a flight attendant into the ceiling and raining the contents of her drink cart all over everybody nearby (she was OK). I’ve experienced extreme turbulence, have flown in blizzards that tossed my plane around like a child’s toy, and have held the hand of a terrified seatmate and stranger.

Many years ago, I was flying out of TF Green in Providence, Rhode Island because of the Big Dig disruptions in Boston. It was a night flight, it was pouring outside, and I had a window seat. Our plane taxied out to the runway and was poised to take off when the roar of the engines died down and we limped back to the terminal. The pilot explained that he wasn’t getting a reading he wanted to see, and that it was probably nothing, but he wanted to be safe and so some technicians would check it out. And so we all sat there in the plane in the rainy dark for about 30 minutes. I was reading a book on my Kindle when the pilot finally came back on the intercom and said it was just like he expected: Everything was fine, it was just a stuck gauge, and we could now leave. As the plane began taxiing back to the runway, the guy next to me spoke for the first time.

“What do you think?” he asked me.

“About what?”

“The plane. Are you worried about it?”

“No, I’m not worried,” I replied. “I have to believe that the people working on this thing know what they’re doing.”

And then I thought about it for a second and added, “But I will tell you this. If this thing goes down, I’m going to be hugging you and crying like a baby.”

To ease the terrible process of flying, I have a set of rituals, almost, that I always follow.

I time my arrival at the airport to occur one hour before boarding time, or maybe 90 minutes if it’s an international flight. Knowing the airport helps: We have flown out of Newark and Mexico City so many times in the past two years that we don’t sweat our departures at all now (and we can cut it much closer in Mexico City, something we keep experimenting with because the process is so quick).

I fly as early in the day as possible because flight issues exacerbate over the course of a day and trickle throughout the system.

I fly non-stop as much as possible, almost exclusively, because a flight delay on the first leg could cause you to miss a connection.

I am a member of TSA Pre and Global Entry so I can get through security and customs as quickly as possible and, in many cases, without needing to take certain items out of my bags. Coming home from an international trip used to be among the worst travel experiences I’ve had, but now it is among the best, and quickest: There are no lines, a device scans your face, and you walk out. Incredible.

I fly on the same airline as much as possible, United, and use a rewards credit card tied to that airline as much as possible, because flying is now our biggest travel cost: We own a place in Mexico City, so we no longer worry about hotel rewards.

Tied to that, we now fly business class as much as possible, and for multiple reasons. We get priority boarding, another key advantage that ensures your bags get a spot, and you can relax while everyone else boards. I’m often the first person on a flight and because we sit in the front, often in the first row, I’m also often the first person off a flight, also key: We can get through customs before the crowd or just exit as quickly as possible. And it’s most comfortable, obviously: As I get older, I find cramped coach seats less and less bearable. It can be expensive, of course, but the Mexico flights are usually reasonable, and we usually have enough points that one of our trips is free. And we only flew to Mexico three times this year: We’re trying to fly less and stay longer on each trip.

I never, never, never check bags. Never. I carry everything on the plane. And though I constantly reassess what it is I need on trips, I always come home with items I never needed or used. Having a place in Mexico makes this semi-comical: I struggled to fill my bag with enough clothes on the last trip there because we have so much there waiting for us.

(The always carry-on rule is controversial in some circles because different people value different things. But baggage claim delays are among the worst one can experience on any flight, and I am not putting myself through that. No one who travels a lot would: Baggage claim is for tourists and other inexperienced travelers.)

My carry-on luggage meets the sizing standards for European airlines, not U.S. airlines, because they are smaller. This ensures that my bag will always fit in an overhead bin no matter what kind of plane it is.

Speaking of which, I put my bags in the bin across from me, not the bin above me. This is a key tip, but it confuses people, even frequent travelers, until you explain it to them. In one recent case, the guy across from me was quite upset to discover my stuff in “his” bin. But when the bag is across from me, I can see it. And that means I can see if some idiot decides to start moving things around to better suit his needs. (It’s always a guy.) On a recent flight, I had to put my bag in sideways because the bin was too small to do it correctly, with the end towards the front, and someone of course tried to “fix” that so his bag could fit there too. I stopped him and explained that the bin wouldn’t close with my bag in the other orientation, and that’s why it was sideways. Problem solved. (My problem, not his problem.)

I have a CPAP, which is horrible to travel with. But because we travel so light to Mexico especially, I have been able to put it in my luggage with my clothes and not worry about carrying a third bag. And it’s about to get even better: I just got a new CPAP via my health insurance, but I am buying a second one to bring to and leave in Mexico. So I won’t even have to carry one on most trips going forward. This is huge.

And then this trip happened. As I write this, I’m in Seattle for Microsoft Ignite. And the weird and last-minute nature of this trip has made for an unusual experience.

We usually fly out of Newark, which is an almost 90-minute drive, but because this trip was sandwiched between my last Mexico Trip and us moving this coming weekend, I wanted to take the long drive to and from Newark out of the equation. And so I violated my nonstop flight rule: I flew out of Lehigh Valley International Airport, which is about as podunk as you can get, because it’s just 20 minutes from our home, and I had a 5-hour layover in Chicago. Which was fine: As part of my status on United, I have free lounge access, so I had a comfortable place to relax and work.

I had just gotten that new CPAP, and I ended up carrying it in its own bag, which is more stuff than I like carrying around, but it worked out. (And airlines have to let you carry it on, it’s medical equipment.)

I stripped down my gadget bag to the bare minimum, and there I lucked out: All my mobile podcasting gear was left behind in Mexico, but the podcast studio at the show had everything I needed. And between that and my CPAP not being in my luggage, I had plenty of room for the work clothes I needed for this trip.

But I perhaps got a little too comfortable in Chicago, an airport I had not flown to, or through, in years. I waited until 20 minutes before boarding time to walk over to the gate, which was nearby, and was surprised to see very long lines of people in the boarding group 1 and 2 areas. I’m so used to our business class accommodations and short group 1 boarding lines to/from Mexico that I had forgotten how bad this could be. I ended up lucking out: By the time I got back to my row 21 seat, there was still plenty of bin space for my luggage and CPAP bag.

But my seat wasn’t so great: I had upgraded to an exit row window seat, but the curved side of the plane intruded into my shoulder space. I was at least able to write on my laptop with no worries: The row in front of an exit row cannot recline, so the guy in front of me couldn’t suddenly jack his seat back and potentially damage the machine. (This is also true of the bulkhead seats I also prefer, in particularly the first row in business class.) But when the flight ended, the couple next to me was in no particular hurry to stand up let alone get into the aisle. When I arrive, I want to stand up and go.

The flight home will be interesting. I have the same basic seat on the flight from Seattle to Chicago tomorrow, and there’s no way to change it: The business class upgrades were too expensive when I booked the trip, and they are no longer offered, and the flight is basically full. And my layover in Chicago is just 45 minutes, so any delay—or any slow-moving seatmates—could really screw things up. I’ll be vocal about deplaning if necessary.

Wish me luck.