Learning to Fly

In late 2013, a glitch on United Airlines’ website allowed anyone to purchase free airline tickets. They were canceled shortly thereafter and given almost no press coverage, but I felt there was a lesson many could benefit from. Here it is below:

Learning to Fly: The Secret Joys of Finding (and Losing) Unlimited Free Airline Tickets

by Max Brawer

It’s a common bit of advice to live every day as though it were your last. Seize the moment. YOLO as hard as possible. Find your passion by imagining that money was no object.

Well, last Monday, www.United.com let me live that fantasy.

I dug the secret out of a quietly excited co-worker at about 2PM Pacific. A certain order of operations on the United Airlines website was allowing users to book flights for only the mileage fees of $5 to $50 dollars. His friend, early to this finding, had already built the itinerary of a retired billionaire and/or international criminal: Brazil for the World Cup, Japan for the hell of it, a few casual hops between New York and California — all in first class. I almost never book a trip anywhere, but could I be that guy, too?

This unholy power was then bestowed unto me via a quick email explanation. And so it began: I could book anything in the entire world for a few dollars. Damn. Where to begin?

Racing against the impending bug fix, I became anxious and greedy. Flight home for the holidays would be good. Savings: $300. No. Got to think big. The destination came easily: for years I’ve wanted nothing more than to go to Japan. “SFO to NRT, round trip.” But I wasn’t dreaming big enough, was I? As a simple and frugal traveler I hadn’t even considered first class. But there it was, for free.

I panicked at the seat selection screen, seeing no seats available to click. Busted. Dream deferred. But then I realized: years of looking around rows 20-24 for a window seat had trained my brain to ignore the front of the plane. Those big orange candy cone-shaped icons in rows 1-5 were seats. Damn. I booked two tickets, figuring I’d sort out the details later, and made it to the checkout screen: $92 for my dream vacation.

But this isn’t a story about how I got lucky and scored a deal…because I didn’t. United has officially declared that they won’t honor these tickets. What I did score, upon reflection, was a very real exercise in “who am I and what do I want?” The high-stakes ticking-clock experience forced many an internal preference into the light.

I had two tickets to Japan and didn’t want to get greedy (at the time) and change the number. It hit me that I needed to give ticket number two a non-transferrable name. Damn. After years of planning, who would be the first person I’d bring along with me? I bit off a few nails and decided on my brother. And it worked. One life lesson and one trip down. Now what?

The difficulty of picking what next on this supermarket spree made me realize how little insight I had into times of year in which I could even travel. I had no more college breaks to rely on and, having only one or two vacation days after my “Japan Trip” was a sad reminder of working life as a United States citizen.

Okay, family first as Walter White would say. I flew my mom cross-country to visit me. Realize I picked a bad weekend, crap. So I “bought” another itinerary. All first class. Now onto me. Where do I want to go? It can be anywhere Max. What about Austin, Texas? Why not. Booked it.

What about something luxurious that I would never pay full price for? Easy: Hawaii. I have a close friend to see AND I can bring a date along. I booked two tickets to Hawaii and forwarded the itinerary with the message “If you’re down…” to a lady-friend, thus becoming that wannabe debonair man of mystery who flies women around the world without notice. Breaking that character I squawked, “booked us two to Hawaii!” A nearby friend lit up: “Us?!”

“Sorry, different us,” I replied.

I was too full of adrenaline and needed to step away from the computer. I began to
reflect and wonder where that adrenaline might have taken others. How many friendships were won and lost in that hour? How many could-be couples took the plunge and proposed an adventure together? How many families booked that one trip that dreamt of for years but never could afford?

One of my favorite expressions is this: the value of flipping a coin to aid a tough decision is not seeing where the coin lands, but realizing what you really wanted as the coin is spinning. Even though the free flights were ultimately invalid, the intensity this experience brought showed us our true colors. Some friends acted altruistically and booked important flights for friends and lovers. Some immediately grabbed a Thanksgiving visit with family. Others told me they didn’t even participate because they just didn’t really feel strongly about seeing any one place.

My reservations may be canceled but my will to travel is emboldened. I never could have told you this before but it looks like I really do want to go to Austin. So I will. And the Japan trip I’ve procrastinated on for so long? I’ve realized how much it means to me and with whom I need to book it. And so I will.

In the future, one can’t simply dream up another United glitch to send them on a spirit quest such as this. However, there are still ways to get the same value. Try going onto Google Maps and saving a road trip. I’m giving you twenty minutes to plan it. Or try going to a site like Kayak and save any one trip into “My Trips.” See what flows. While you’re at it, tell someone that you really want to take an adventure with them. It may not be two first-class tickets to Italy, but acting on a trip that is meaningful to you is worth all the imaginary MileagePlus miles in the world (plus taxes and fees, of course).