Travel Like A Pro


We are what we repeatedly do. Excellence, then, is not an act, but a habit.

Aristotle

Welcome to the first installment of Travel Like A Pro. The focus of this column is on how professional travelers deal with “the stuff” that most normal people just accept as part of the deal. In this first column, we’ll discuss things that can make your airplane experience better. (And in future columns I’ll cover how professionals handle hotels, communication and more.)

As you read this column you might think it has a “duh” factor to it, or perhaps you’ll realize that some of these tips are things you already do. But if so, you’re already thinking like a pro traveler. And if not, try it for a while and see if it doesn’t make travel more enjoyable for you.*

There are plenty of books to tell you how to travel like a pro. I’m going to tell you what it’s really like, because the pros make it look easy and it isn’t.

To be a pro you have to be able to do a lot of things at once: read on the plane, work on the plane, sleep on the plane, entertain yourself for hours at a time with nothing but a book, ignore both conversation and other distractions, and so on.

I’m going to give you some tips here. But first I want to warn you: none of these tips are easy. They are hard. You will have to practice them over and over again before they become natural. Most of them require a lot of self-knowledge: knowing what kind of environment you need in order to do them well. And some are simply not available to most people until they’ve had enough practice at traveling that they know what works for them.

You’ve seen them before. Even if you’ve never flown in one of the airlines’ premium cabins, you’ve probably encountered those travelers who seem to always be on their way to somewhere else, who manage to get on and off the plane with a minimum of fuss and stress (while looking like they just walked out of a salon or a spa), who read a book or magazine for hours without even losing their place, and who somehow seem to be at home in the airport lounge.

Well, here’s the good news: there’s nothing mysterious about how they do it. They’re not smarter than you are, nor do they have more money or better connections. They just know some tricks that make traveling easier and less stressful. And now you can learn those tricks too…

When I first started traveling for business, I was a mess. I would get to the airport and not know how to check in or where to go. When it came time to board, I wouldn’t know what group I was in. I would be sitting on the plane sweating, hoping that the person next to me didn’t hate me too much.

Today, I get on planes with ease, and as someone who travels frequently, I have become more efficient at the process. Here are my tips and tricks:

1. Know your airline. Each airline has its own quirks. On American Airlines, you can use their website or mobile app to view your boarding pass right on your phone. This saves paper and it’s convenient! But on other airlines, this isn’t possible (yet). Knowing which airlines allow you to board with a mobile pass will save you time during check-in – no need to stand in line if you don’t have to! If you travel often, it may be worth having two different credit cards – one for domestic travel and another for international flights – just so you can rack up frequent flier miles with multiple airlines.

2. Check the weather ahead of time. Professional business travelers do not show up at an airport without

Airlines have a bunch of tricks to get you on the plane. If you don’t want to be fooled, and you don’t want to pay more than necessary, here’s what you need to know.

You probably already know that airlines price tickets based on how likely they are to sell. The higher the demand, the more they charge. This is one reason why it’s so important to buy your tickets as far in advance as possible: fares often go up as the flight date approaches, and eventually they might even sell out. But there are other ways airlines try to get as much money out of each seat as possible—and not just by making an extra $20 for a window vs. aisle seat. They also change their prices based on where you’re searching from, what kind of device you’re using, and even how many times you’ve searched for flights recently.

How do airlines make this happen? By using cookies! (Not those cookies.) Cookies are small pieces of data that websites store on your computer so they can remember things about you later—like whether or not you’ve been to the site before or if you’re logged in at the moment—and tailor your experience accordingly. If an airline sees that you’re visiting its website with a cookie

When I was in my early twenties, I flew a lot. My first job out of college was a consulting gig that required traveling every week. I’d buy flights on the web, renting cars and hotel rooms, too. After the consulting stint ended, I took a job at a startup. The company had an office in New York and most of the team lived there, but because I had no ties to the city, I stayed in Boston and commuted every week.

I remember spending hours online booking flights for my consulting gig: comparing airlines, flight times, and routes. Once I settled on a flight, I would research hotels nearby. If there was more than one option nearby, I’d compare prices and amenities to find the best deal. If it was an overnight trip, I’d book a car as well. Finally, if it was an early morning flight or late-night return, I’d look up airport parking options so that my car wouldn’t be towed while away.

It took hours to plan each trip — sometimes more time than the actual trip itself.

Traveling for work has become easier over the years thanks to technology: online travel agencies like Expedia; Uber and Lyft; Airbnb; hotel apps like HotelTonight; and Google Flights have

By Chris Guillebeau, author of The $100 Startup

You know that feeling when you’re midway through doing something — maybe listening to a nostalgic song, maybe dancing — and some fundamentally huge penny drops in your head?

Well, I just had one of those moments.

I was getting ready to board my flight from Las Vegas back to Portland a couple of weeks ago. I’d been at an event and had been lucky enough to be upgraded to first class. This is a nice thing that happens sometimes in our business, but it’s not something I expect or even take for granted.

As I was walking down the jetway, I realized something: “Wow, this is incredible. Every single time I fly somewhere, someone gives me their seat.”


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