There’s Nothing Cheap About Loyalty

Up In The Air is about a man who spends his entire life traveling for business. In the film there’s a scene where George Clooney’s character, Ryan Bingham, is discussing all of the hotel, rental car, and airline loyalty programs he is a member of. He explains that there’s nothing cheap about loyalty.

Until a few months ago I was a member of two loyalty programs just by happenstance. By joining the Hilton Honors free loyalty program while booking a hotel room, I was able to get a later checkout time and free Wi-Fi. I fly American Airlines once a year for work, so I joined their AAdvantage program to hopefully one day get a free flight or upgrade. But I figured I’d have to be an actual frequenttraveler to make any of these points count for something.

My loyalty was very cheap.

But today I’m a member of eight different rewards programs, two of which I’ve earned elite status that merit even more rewards and perks. I’ve acquired over 250,000 AAdvantage miles, 75,000 HHonors points, and nearly $500 in cash back — all of this since March. All of this with zero debt. And all of this with a credit score of over 800. Today I realize that collecting loyalty points has developed into a full blown obsession.

Okay, you got to fill me in on the miles thing.

Ryan Bingham’s whole existence is dedicated to accruing as many American Airlines miles as possible. His goal is ten million for no reason other than the status that it will bring him. Bingham explains that the miles are the goal. Anna Kendrick’s character, Natalie Keener, tells him with that many miles she’d show up at an airport, look at the board, and make a decision where to go. But for Bingham, it’s not about the destination at all, it’s really an obsession that has caused him to live an extremely isolated and lonely life.

In the film you learn that Bingham’s only real possessions are contained in his suitcase. He has no real friends and very limited connection with his family. Bingham’s obsession over miles eventually has very severe consequences.

You might say that I tend to have an obsessive personality. My obsessions don’t lie in anything destructive, but tend to center around accumulating things. In middle school I obsessively collected CDs through Columbia House. In high school I obsessed over Blockbuster’s pre-owned DVDs. In college I obsessively curated an enormous iTunes collection by taking advantage of every open computer on the dorm network. The thing is, with all of these obsessive collections, I barely touched a small percentage of the things I obtained. It was the hunt that was exciting — the possibility of capturing a bigger and better collection drove the obsession.

I can relate to Ryan Bingham.

The rewards points game has become my current collection obsession. I’ve read hundreds of forum threads, blog posts, and Reddit comments trying to understand strategy. I’ve figured out what programs can link together and ways to try to mimic Bingham’s miles obsession.

Loyalty points have replaced CDs, DVDs, and digital music to become the latest thing I obsessively collect. Unlike the others, however, loyalty points are a lucrative obsession. After all, as Bingham states, “there’s nothing cheap about loyalty.”

I don’t spend a nickel, if I can help it, unless it somehow profits my mileage account.

I’ve never been a fan of credit cards. I don’t like owing anyone anything, let alone money. And the idea of interest — of paying the credit card company more money because I spent more than I should have — I’m not into it. My wife and I lived frugally for the last two years in order to pay off the credit card debt we acquired after getting married and buying a house. Since then, we’ve avoided credit cards like the plague. Then my brother explained that he and his girlfriend would be spending a month in Europe with most of the trip paid for by credit card loyalty points. My interest was piqued. I started playing the game.

In the last few months I’ve opened eight different credit cards and one checking account to take advantage of their sign up bonuses. These bonuses typically come in the form of a certain amount of free miles for spending a certain dollar amount in a three month period. Some come with annual fees that are waived for a year, some are free, and others you have to pay for right away.

In the few months I’ve been playing the game, I’ve accrued enough miles for my wife and I to travel business class round-trip to Tokyo — a trip we’re planning for next year. The airfare alone for that flight would be well over $10,000 if we were paying for it, an amount of money we would never be able to afford. But with the points we’ve already earned, the trip will only cost around $100 (there’s a slight fee for redeeming the points).

I’m now turning my attention to cards that will provide hotel stays. The goal is to earn enough points and free night certificates that by the time the trip rolls around, that will also be free. But in order to do this, I have to get even more obsessed. I have to go further down the rabbit hole and make sure every purchase is mapped to the right card using very detailed spreadsheets — different cards provide different bonuses depending on the merchant. I have to open even more cards, link even more loyalty programs, and dive into a deeper level of the loyalty points game.

And herein lies the problem with any obsession: the hunt begins to outweigh the satisfaction.

Earning the points and booking free travel is highly satisfying, but will it be enough? After we visit Tokyo (hopefully for free, hopefully aboard the new 787 Dreamliner) will I be satisfied or will my obsession lead me to wanting more? More points? More cards? I don’t know the answer to these questions. But I do know that at some point every obsession comes with a sense of fatigue.

You know how many times I thought about this moment?

Towards the end of Up In The Air, Ryan Bingham achieves his goal of ten million miles. It’s a moment he’s been looking forward to for a very long time but brings almost no excitement. Instead of satisfaction, Bingham realizes what he gave up in his chase of the goal and finds he is tired of the whole thing.

Again, I can relate.

The prior obsessive collections all ended because they became too much of a burden. All those CDs and DVDs needed a place to live and eventually were replaced by digital files that too became quite unruly in their own right. I imagine at some point obsessively collecting loyalty points will become more of a burden than a hobby. But until then, I’m going to continue to obsess over the process. I’m going to continue to soak up as much information as possible and continue to collect as many points as possible.

Tokyo, here we come.

Update: 5 Months Later (November 27, 2015)

After plenty of research the obsession has paid off. My wife and I now have two business class tickets booked in Japan Airline’s 787 Sky Suite for next year. The cost of these tickets, had we been paying cash, would have been $20,474. We paid a total of $98.20 to the airline and $198.00 in annual fees to the credit card company. We also have enough hotel points to cover our rooms for all eight-nights we’ll be in Japan.

I can safely say that when the moment of booking arrived, unlike Ryan Bingham in Up In The Air, I was exuberant. The thrill of getting something extremely valuable for almost nothing brought a tremendous amount of satisfaction, but securing a dream I’ve had for years brought a level of excitement that is hard to describe. Less than a year from now, we’ll be exploring Japan.

Tokyo, here we come indeed!