6 Confessions of an Avid Travel Hacker

Hacking your way to nearly-free travel is incredible — and addictive.
Dec 1, 2021

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It starts innocently enough. You open one travel rewards credit card to help subsidize an upcoming trip. While on that trip, the flight attendant announces that you can earn enough miles for two round-trips with a new card, and you jump at the chance to apply in-flight.

From there, you’re hooked. Once you learn how to harness the power of points and miles for travel, you want to do it more and more often. You join the ranks of rewards optimizers and fall down the proverbial rabbit hole. One card leads to another, and before you know it, you’ve amassed a large collection of loyalty accounts, credit cards and free hotel night certificates. You might even wind up with elite status in multiple programs.

From the diary of a self-proclaimed “travel hacker,” here are six realizations you may also have if you fall head-over-heels for points and miles.

1. It's hard to go back

After you've learned how to score lie-flat business class tickets to fly across the world for "free" using your points and miles, it's hard to go back to that cramped coach seat that barely reclines. Once you get accustomed to luxurious hotel suites, that standard room seems sad by comparison.

On those occasions when you can’t score a seat toward the front of the plane, or when you get stuck in a small hotel room with no view, travel disappointment kicks in. If your children are sometimes lucky recipients of the fruits of your travel hacking, their disappointment hits you doubly hard.

“Normal” just doesn’t cut it after you’ve experienced the finer things in life.

2. Trips with non-travel hackers can be tough

When you're flush with points, it's easy to book that expensive hotel without a second thought. For your friends who're shelling out cash, it's a different story. You don’t want to be that friend, so you agree to the modest select-service hotel on your weekend away together. But inside, you suffer. (See point No. 1.)

If a group of friends suggests a ski trip, you shudder at the thought of booking a condo. Sure, you can all enjoy a shared space, but you can't use your hotel points to cover the cost and will — gasp — have to pay in cash. Then, your friends have the nerve to complain when you want to charge everyone's lift passes on your credit card to get the points, and ask them to pay you back in cash.

3. Home life FOMO is inevitable

When you're using your stash of points and miles to take off on weekend adventures, that means you're often not at home. Your neighbors stop inviting you to their BBQs because “you can never come anyway." The kids miss soccer practice, yard work piles up, and your suitcase remains perpetually half-packed on the floor. Your cat gives you “the look” every time she realizes you’re getting ready to leave again.

But all that is forgotten when you spot a wide-open three-day weekend on your calendar. The travel bug strikes and plans are quickly made. After all, who wants to pick weeds when you can check out the Japanese Gardens in Portland or walk through the tulips in Amsterdam?

4. Trip planning can be harder than it needs to be

For non-travel hackers, planning flights and hotels for a trip probably involves light research and a few booking platforms. Non-travel hackers book the cheapest flight, find a reasonable hotel in a good location, and call it a day.

For travel hackers, though, planning a trip comes with endless decisions, like:

  • Do I want to use my free night certificates that expire in a few months, or should I pay cash to earn triple points with the latest promo?

  • Should I use a modest number of Avianca LifeMiles to book a just-OK flight, or should I use a larger number of United miles to book a flight with a better travel time?

  • Should I use my rewards to book through a credit card travel portal, or should I transfer those miles to a partner airline?

  • Should I pay a little bit more to book my room directly through the hotel so I’ll earn my elite night credit?

Whew. Talk about analysis paralysis.

5. Destinations can become secondary to maximizing value

When your cup runneth over with hotel points and certificates, the travel planning process can work backward.

Rather than first thinking about where you'd like to go and then figuring out accommodations, you start with the hotel. Which cities have a nice IHG property where I can get the best value out of my free night certificates? Where are the best Hyatts to use my suite upgrade awards and enjoy my status to the fullest?

And when you have a pile of airline miles, it’s tempting to think first about what routes are best on that airline from your local airport.

You may have thought that you wanted to take a scenic trip to the Scottish Highlands. But now, instead, you really want to head to Chicago to get the best possible hotel experience at the best possible value. Or … do you?

6. You'll have constant travel envy

Enthusiasts of many hobbies are known to seek each other out and build a community, and travel hacking is no different. Once you get hooked on points and miles, you’ll find you have a bunch of new friends to nerd out with.

And no matter how much you travel, someone in your circle is always traveling more. A whole lot more. When you're proud of your week in Hawaii, someone else is doing a month-long round-the-world trip, stopping in England, France, Japan and the Maldives. And they’re plastering pictures all over your social feed. Every. Single. Day.

Then, of course, you're compelled to book more travel for yourself. Ah, the vicious cycle of travel hacking.


How to maximize your rewards

You want a travel credit card that prioritizes what’s important to you. Here are our picks for the best travel credit cards of 2022, including those best for:

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