Five Travel Mistakes I Never Should Have Made

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As anyone who knows me is already aware, and anyone else reading this sentence is about to be, I travel a lot for work. Not nearly as much as some in my industry, but for seven or eight months out of the year I’m on a plane multiple weeks per month. August is the only month of the year in which I absolutely do not fly under any circumstances (unless those circumstances include seeing Pearl Jam play in Montana with my best friend).

Not only do I travel far more than I would like for work, I’ve been doing it for a long time. I won’t say exactly how long because it makes me feel old, but trust me, it’s been a while. Long enough, in fact, that I remember the days when you could waltz through security in 15 minutes with your belt on and laptop and liquids in your bag. And not because of Pre-check, because there was no Pre-check.

While I’ve traveled more than my fair share, however, I haven’t always been smart about how I did it. In spite of all of that time on planes and asleep on airport bench seats, it took me far, far too long to learn the lessons below. Which is why I offer them certainly for those who travel for work, but even for those who don’t and may find a tip or two to make their lives easier on the road. As an aside, here are 35 prior tips for those interested in such things.

One quick caveat, most if not all of these recommendations come with some cost attached, and the cost in a few cases is high. The costs are justifiable for our business because of the amount we travel, but we also have the privilege of having some wiggle room to make our lives on the road marginally easier. That isn’t true for everyone, obviously, so your mileage may vary with these suggestions.

Still, they may be of use to some of you, so enjoy.

Not Optimizing for Lounge Access

These suggestions are listed in no particular order, but if I had to pick the biggest mistake I made this would probably have been it. With the exception of my time as a systems integrator when I was largely an American Airlines customer, I’ve spent the bulk of my career traveling on JetBlue. In general, JetBlue is an exceptional airline with much to recommend it, which is why I spent well over a decade giving them thousands and thousands of dollars of my business annually.

There are two big problems with JetBlue for the business traveler, however. First, their loyalty program doesn’t show much loyalty to the frequent traveler – which is why I dropped them for Delta. Second, JetBlue has no network of lounges (technically, there was one they didn’t run at their fancy T5 terminal, but, well, things didn’t go well). This didn’t seem like a major issue until I switched to an airline in Delta that has an excellent network of lounges.

There are far, far too many benefits to lounges to document them all here. The free food can be nice. The free drinks, even better (with self-serve taps, even). But then there is comfortable, nicer seating – seating that invariably has power outlets. Regionally available full shower access. Bartenders that will set up TV’s for you during the Red Sox World Series run. Staff that will help you rebook when you unexpectedly get stranded in NYC during a surprise snowstorm. Some even have conference room space for meetings.

Even if you’re not like me and you don’t get to the airport two hours early – minimum, at some point if you travel a lot you’re going to get stuck at an airport for a while. At which point your choices are uncomfortable seating near a gate or an overcrowded and overpriced airport bar or restaurant. Unless you prioritize lounge access, that is.

I didn’t for years. We got AMEX Platinum cards for everyone who travels years ago, and the AMEX Centurion lounges they maintain are incredibly nice. Unfortunately they are less than common, and even some airports that have them (looking at you, SFO) they’re in the wrong terminal for me. It wasn’t until I switched to Delta this fall that I got the full experience, and it is legitimately life changing.

If you travel and don’t have lounge access, then, I’d find a way to make that happen. It’s completely worth it.

Not Prioritizing Loyalty Programs

I didn’t make this mistake for nearly as long, thankfully, but in the early days of RedMonk I was optimizing for route efficiency rather than loyalty programs and thus ended up with either a wide distribution of my business that afforded no status anywhere, or elite status on an airline (JetBlue) that didn’t offer much in the way of tangible returns.

After years of flying, however, I eventually realized that thanks to delays and the other vagaries of air travel, route efficiency was more of a theoretical advantage for me. In practical terms, the difference for me in a one hop flight to SFO out of my home airport in Portland versus a direct route out of Boston was negligible. Door to door, my actual elapsed travel time was similar enough, and breaking up a transcontinental flight into two shorter segments isn’t all bad.

When you start planning itineraries, then, think carefully about your strategy. Most of the people I know who travel a lot will take zig-zaging routes over direct alternatives if necessary in order to build up status, because that status is worth more to them over time than the perceived or even actual benefit of a direct shorter flight.

If you’re flying once a year, always take the direct flight. But if you’re traveling regularly for work, odds are loyalty will be worth some less optimal routes.

Not Optimizing for the Least Weight Possible

The single biggest difference between how I travel today and when I started is my bags. As something of a worst case thinker and occasional reader of apocalyptic fiction, my luggage would be packed full of redundancies: extra clothes, extra cables, extra chargers and a choice of computing devices. And those computing devices would, once upon a time, have been the most powerful I could get, weight be damned.

Which is how I spent so many years hiking around airports with sore shoulders from lugging around enough infrastructure to power a dozen Apollo missions.

Since then, I have steadily and methodically simplified my approach, stripping my inventory down to only what I’m likely to use on a given trip. With the exception of headphones, where I always carry a backup set, I don’t do backups anymore: no more extra clothes, cables and chargers – I carry only what is needed to charge what I carry. And what I carry is itself optimized for weight. I travel exclusively with an iPad Pro now, for example, because it’s half the weight of even ultralight laptops. Even better, the iPad Pro I carry (this one) charges via USB-C, which means I can carry just a single, small dual-port USB-C charger (this one, specifically) to keep both my tablet and phone charged.

This simplification accomplishes a few things. Most obviously, my bag is a lot lighter than it used to be, which is nice if you need to sprint to make a tight connection. But it also means that I have substantially less gear to wade through to find what I need and to potentially lose, damage or troubleshoot.

Not Getting Pre/Global Entry Sooner

Of all the things I dragged my feet on, this was one of the worst. Part of the issue was that I needed to track down documentation as part of my interview process, which took a while, and part of it was that I hoped against hope that my country would come to its senses about the pointlessness of security theater, but in general I just didn’t prioritize Pre or Global Entry as soon as I should of.

Anyway, a while back I finally got my paperwork in order, applied and was granted access to the Global Entry program. This means that I both have access to Pre domestically and then Global Entry while traveling internationally.

Pre by itself is worth it because you don’t have to be virtually strip searched to board a plane and because you can leave your laptop in your bag, your belt and shoes on, etc. The line is often shorter as well, particularly here in Portland, but that’s not my primary motivation.

Global Entry, meanwhile, is less useful to me because I travel internationally a few times per year max, but when I do the program is amazing. I can get off a full Aer Lingus flight from London, and be one of a handful of people with Global Entry who waltz up to a machine, feed it a passport and fingerprints, take the slip it provides me over to a border customs agent and be on my way. I don’t think it’s ever taken me longer than ten minutes to clear customs coming back into the States from abroad. And on several occasions, this has been the difference between catching an earlier bus home versus an extra hour or two at the airport.

Put those two together, and the benefits are obvious. Or should have been, at least, when I was spending all those years getting gangprobed by the TSA because I declined to go through the porno scanners out of principle.

If you travel only domestically, Pre is all you need. If you are abroad even once, the extra $15 for Global Entry is a no brainer.

One pro tip for scheduling your interview with Global Entry: if your home airport is booked way out – the wait for an interview at Boston was four months when I applied – find an open slot at an airport you’ll be traveling through and book it there. The wait at JFK was three weeks, and I found an opening the overlapped with a planned trip.

Not Getting a Platinum Card Sooner

As a small business, James and I have always tried to run a tight ship. We try to make our employees comfortable while traveling, but we’re not extravagant spenders. Because of this, we had to think long and hard about whether to invest in Platinum cards for our employees because they are not cheap – $475 at the time, and $550 now.

In retrospect, this was silly. We’ve easily recouped the value from these cards, not just in convenience and wear and tear benefits while traveling, but in hard savings as well.

The Platinum card comes with a number of built-in credits: the $100 Global Entry fee, for example, is waived. There’s a $200 Uber credit and a $200 airline fee credit. There’s also a Saks credit, though I admit I haven’t used it. Just between the credits, then, you’re close to offsetting the card’s cost.

Then there are the status benefits. You get Hilton and Marriott Gold status by default, along with entries into the Hertz Gold, Avis Preferred and National Car Rental Emerald programs. This means that I will get room upgrades and late checkouts at hotels (though not the 4 PM checkouts that used to be available from Starwood), and on the few occasions I’ve had to rent a car you get treated…differently.

At one point I missed a flight, and needed to drive from Boston to Portland in time to make a consult. The people at National, thanks to my status, told me to “just pick whichever car I liked.” Which honestly felt like theft, but explains how I ended up making a high speed transit up I-95 in an Audi for the price of an economy rental.

Perhaps best of all given the first item on this list, Platinum cards get you lounge access. Specifically you get free entry to AMEX’s own Centurion lounges (which are incredible), access to Priority Pass’ network of member lounges (though I’ve had mixed experience with that one), and access to Delta’s lounges if you’re flying on Delta.

Honestly, given how valuable lounges have been, the AMEX might have been worth it on that basis alone, but overall the value of the Platinum card is easily justified if you’re a frequent traveler. Our mistake wasn’t getting them, but rather waiting so long to do so.

 

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