Can you win playing by the rules?

Last month I spent a lovely Saturday afternoon in the Minneapolis-Saint Paul International Airport conference center for the long, long, long-delayed Milenomics Second Planned (MSP, get it?) Meetup. Sam and Robert, the brainiacs over there, did a lovely job and I got to kick back and relax all day with a few dozen members of their Patreon community, and see some old friends from all around the country for the first time in much too long.

Over the years I’ve attended quite a few gatherings like this (and hosted a fair share of my own), and my overwhelming impression is simply how different they all are. All the way back in 2014 I covered the gauzy Frequent Traveler University event in Seattle and came away equal parts bored and annoyed. When Saverocity was more active, I found their Phoenix and Charlotte events were well-run and great opportunities to meet more like-minded members of the community. I haven’t made it to the Chicago Seminars or Ann Arbor Art Fair meetups, but have heard rave reviews of them from their own diehard fans.

The point of all this is not to recommend or even criticize one sliver of the travel hacking community over another, but rather to point out that different slivers are different! If you don’t fit in in the first group you join, that doesn’t mean everybody else in the community is a boring loser and you’re the only one who really gets it. It means you had bad luck — that group wasn’t right for you, but it might be perfect for people who aren’t like you.

What I found most interesting about the Milenomics meetup was not how similar everyone was, but how different they were, and I’ve been turning over how to express what, if anything, passionate travel hackers have in common.

The rules describe everything that has already been thought of

Like lots of kids, I grew up playing the board game “Monopoly,” with its iconic instructions:

“GO TO JAIL.
“Go Directly to Jail
”DO NOT PASS GO
“DO NOT COLLECT $200.”

This is a wonderful manifestation of the general principle that you can only write rules around situations that have already occurred to you. Monopoly is a game of randomized clockwise movement around a rectangular board. If the Jail square is between your token and the GO square, there’s no question that you have to move your token there without passing GO. But if the GO square is between your token and Jail, what are you to do? You are to go “directly” to Jail, without passing GO, violating the game’s main rule of one-directional, clockwise movement.

Playing by, around, and against the rules

The question, then, is do the rules describe every possible situation? Of course not. A few years back IHG Rewards ran a promotion that allowed you to enter into a sweepstakes up to 94 times by mailing hand-printed pieces of paper to some P.O. Box in Kalamazoo. But the rules didn’t say who had to hand-print the pieces of paper, so there was nothing in the rules against enlisting some kids with neat penmanship to fill out your 94 entries for you.

And this, I think, constitutes one of the many divides in the travel hacking community:

• Should you play by the rules, and only do the things explicitly laid out by the companies we interact with;

• Should you play around the rules, identifying the “Air Bud” holes where some action is neither explicitly permitted nor explicitly prohibited;

• Or should you break the rules, counting on sloppy implementation or enforcement?

Most people do some of each, and that goes beyond the specific domain of travel hacking. Take the case of vaccine mandates:

• the overwhelming majority of people subject to vaccine mandates simply comply and receive the mandated vaccines;

• some people observe the possibility of “religious exemptions” or “conscientious objection” to vaccine mandates and fabricate those exemptions or objections;

• and some people go further and fabricate the documents themselves in order to violate vaccination requirements.

The scarcest resource is not time, but focus and attention

One of the strangest arguments in the travel hacking community is about the “value” of your “time.” It’s certainly true that hourly workers are compensated for their time on an hourly basis, and that a small subset of salaried workers are paid overtime when they work more than 40 hours per week, but my extremely literal viewpoint is that when you’re not being paid for your time, it’s yours. It’s free, God-given, to do with what you please.

The manufactured spending I don’t do online, I do on foot. In other words, I go for a walk. In every other context, “going for a walk” is treated as a leisure activity. In my case, I also make money doing it. But the time is free: I exchange pleasantries with my neighbors, breathe fresh air, and enjoy all the benefits of daily light cardiovascular exercise.

Where I see the biggest divide between affiliate bloggers and travel hackers is in how seriously they take the shortage of focus and attention, not time. Participating in a buyers group doesn’t take much time at all, compared to going for a long walk. But keeping track of shipments, deliveries, and payments requires focus and attention that could be used elsewhere, even if it consumes just a minute or two per day. This is not a criticism: if you find participating in buyers groups fun, then that’s what you should do. But don’t make the mistake of thinking the resource you’re expending is your time.

If you want to play by the rules you have to stay even more focused

The error I see affiliate bloggers promoting most consistently is that it’s worth playing by the rules (the only rules affiliate bloggers are allowed to tell you about) and getting dragged deeper and deeper into the travel hacking community. To me, that’s an either/or proposition.

A perfectly reasonable way to go through life is to sign up for a Chase Sapphire Preferred card, put all your purchases on it, and each month transfer your entire balance of Ultimate Rewards points to World of Hyatt. Then whenever you need a hotel stay, see if there’s Hyatt award availability. If there is, book the Hyatt. If not, pay cash. The same logic applies to an American Express Gold card with transfers to Delta.

Likewise, I’ve happily written about a basic credit card strategy consisting exclusively of cards with annual companion tickets (Alaska and Delta) and hotel nights (Hilton and Hyatt).

But if that’s your strategy then you need to log off, not read any blogs at all, not follow any travel hackers on Twitter, and not listen to any travel hacking podcasts. Not because they’re a waste of time, but because they’re a waste of focus and attention.

The reason to get engaged in the community is to find out what rules can be bent and broken

The rewards of getting involved in the travel hacking community can be enormous, but they’re not free. Learning how to search for partner award availability across multiple airline alliances is a huge undertaking. Tracking signup bonuses and transfer partners isn’t particularly time-consuming, but it does consume focus and attention that you’re otherwise free to expend elsewhere.

Fortunately, travel hacking has the same safety valve built into it that all hobbies do: if you don’t find it fun, you don’t have to do it! Whenever my friends or family approach me to ask how to get started I tell them the same thing: do one thing, anything, and see if you enjoy it. See if it captures your imagination. See if you want to do more, faster, more aggressively. And the simple fact is, no one has ever taken me up on it, because the overwhelming majority of people find it mind-bendingly boring.