When the Fun Stops

If you've ever visited Las Vegas, you've no doubt seen the constant parade of advertisements run by the Nevada Council on Problem Gambling, with the campaign slogan "When the Fun Stops."

I've persisted, in the face of pressure from Rolling Stone, in calling travel hacking "the game," which makes us players, and which usefully raises the specter of problem gaming. In general, I think there are three ways a healthy attitude towards travel hacking can become problematic.

Getting stuck on the status treadmill

One of the great intellectual triumphs of the loyalty industry was making it difficult — but just easy enough — to qualify for elite status. Hotel loyalty programs offer three good examples:

  • The Hilton HHonors Surpass American Express and Citi Hilton HHonors Reserve give top-tier Diamond elite status after spending $40,000 on either card;
  • The Starwood Preferred Guest American Express gives 5 nights and 2 stays towards SPG elite status just for being a cardmember;
  • The Chase Hyatt Gold Passport credit card gives 2 stays and 5 nights towards elite status after spending $20,000 with the card, and 3 stays and 5 nights towards elite status after spending a total of $40,000 with the card each calendar year.

Likewise the Delta Platinum and Reserve business and personal American Express cards each offer Medallion Qualification Miles towards elite status at certain spend thresholds, the Citi / AAdvantage Executive World Elite MasterCard offers 10,000 Elite Qualifying Miles after $40,000 in calendar year spend, and the Barclaycard AAdvantage Aviator Silver World Elite MasterCard gives 5,000 Elite Qualifying Miles after spending each of $20,000 and $40,000 on the card per calendar year.

For an experienced travel hacker those thresholds are easy to meet, which is easy to confuse with being worth meeting.

But if you'll enjoy few or any of the benefits of elite status, you shouldn't be going out of your way to earn — or even think about earning — elite status in programs you don't actually take advantage of!

Losing track of point values

The Chase Marriott Rewards credit card has earned 1 Marriott Rewards points per dollar spent everywhere, well, forever.

But the Marriott Rewards program has undergone a series of horrific devaluations since the credit card was introduced!

The same card that would have earned you three free nights at the JW Marriott in Washington DC for $50,000 in spend will now barely earn you one night for the same spend (the property now costs 40,000 Marriott Rewards points per night).

If you got on board early, you could have powered your way through a series of devaluations and suddenly find yourself earning far fewer stays for the same amount of spend.

Losing track of costs

This is a story I've told before, but I think it's still illustrative. I was introducing a friend to travel hacking right about the time when Vanilla Reload Network cards stopped being sold to credit card users at national pharmacy outlets.

I broke the news to my friend and explained that only cash was now accepted for the reload cards. And my friend, who was eager to earn as many United MileagePlus miles as possible for an upcoming trip, asked me, "well, what if I take out a cash advance from my card and use the cash to buy a Vanilla Reload card?"

It's a funny story, but it illustrates an actual problem I see all too often: once folks are stuck in a groove, they'll do anything to stay in that groove, even when the costs slowly (or rapidly!) start to outweigh the rewards they were initially earning.


At the end of the day, I'm a travel hacking enthusiast. I think this game, in the huge variety of forms it takes, will be around for a long, long time to come.

But that general relaxation about the bigger picture shouldn't be treated as an invitation to take your eye off the particular credit cards, programs, and techniques you use!

A relentless focus is the only way to make sure you're getting the most value out of every second you spend playing this game.

And if you don't have that focus? Well, there's always tennis.