6 things no one tells you about earning points and miles

Jul 4, 2020

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I can still remember the adrenaline coursing through my veins while I waited for Chase to finish processing my application for the Chase Sapphire Preferred® Card, my first real travel rewards card. I didn’t know it at the time, but my life was forever changed when the “congratulations, you’ve been approved” message popped up on my screen. I was officially an award traveler, and the world was about to get a lot smaller.

Since that day I’ve earned and redeemed over 5 million points and miles. I’ve flown first class with some of the world’s best airlines and stayed in some of the most expensive hotel suites and villas on the planet. I’ve also had my fair share of mistakes, disappointments, and stressful situations. Here are 6 things no one tells you about points and miles that I’ve learned along the way.

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In This Post

Your 5/24 slots will be gone in the blink of an eye

When you’re new to the world of points and miles, and perhaps new to credit cards entirely, it can be easy to look at Chase’s 5/24 rule and assume it doesn’t apply to you. The rule says that you’ll automatically be rejected when applying for Chase cards if you’ve opened five or more cards across all issuers in the last 24 months (excluding most business cards). I can tell you this: those five slots will go quicker than you can possibly imagine.

It took me just four months to use up my five slots, and from that point on I was locked out of applying for more Chase cards. While that’s certainly on the fast side, many people will blow through their five slots in the first 10-15 months. What this means is that early on, you can’t afford to deviate and apply for non-Chase cards, no matter how tempting the offer. I made that mistake by opening a Citi college card, and to this day that decision still haunts me. I still haven’t been able to slow down enough to get approved for a Chase Ink Business Preferred® Credit Card, which tops my wishlist thanks to its 100,000-point bonus after spending $15,000 on purchases in the first 3 months from account opening.

Related: The best ways to use your Chase 5/24 slots

Analysis paralysis is real — and can cost you your dream vacation

At the beginning, it might take you months or even a year to save up all the points you need for your dream vacation. When you’ve put in so much time and work to build up your points balance, redeeming them for anything less than perfection can be difficult. Analysis paralysis is quite real, and while you’re debating whether to fly EVA business class or United Polaris, both awards may well disappear. I know too many people who’ve let a Maldivian vacation slip through their hands because they were holding out for the St. Regis, even though the W, JW Marriott and Westin all had plentiful award availability.

Related: 6 reasons to pick the W Maldives over The St. Regis

I’m certainly not advocating that you redeem your points randomly without paying attention to the value you’re getting, but know when to settle for good (or even great) instead of chasing after the elusive perfect redemption. If you’ve never flown in a premium cabin before, maybe settle for business class instead of first class. Book the second or third nicest hotel in the city if the first one doesn’t have award availability. At the end of the day, it’s hard to go wrong getting a free luxury vacation. A friend of mine once put it quite well: “The least valuable point is the one you never redeem.”

(Photo by Ethan Steinberg/The Points Guy)
While most people would consider the St. Regis to be the most luxurious property in the Maldives, I found that I enjoyed my stay at the W much more. (Photo by Ethan Steinberg / The Points Guy)

You’ll become the travel agent for your friends and family

When I started opening dozens of credit cards during my sophomore year of college, most of my friends thought I was crazy. Some thought I was a criminal. Even my dad, who’d leveraged travel rewards throughout his long career as a lawyer, didn’t understand when I explained that I had enough points to fly around the world in first class several times over.

Expect some confusion and resistance when you try and explain your new hobby to friends and family. But once that wears off, expect to be bombarded with requests every time they need help booking travel. Hopefully you can teach them a thing or two about the world of points and miles and even rack up a few credit card referral bonuses in the process to reward you for your time. But one thing’s for sure: once your friends start to see the incredible trips you’re taking for free, they’re going to want a piece of the action.

Don’t get caught up chasing elite status

Credit card rewards are the great equalizer. Anyone with a good enough credit score can earn points and book a $20,000 first class ticket for free, no matter how much money is in their bank account or how often they travel. But beware the siren song of elite status.

Of course everyone wants to be treated like a valued elite member, to say nothing of the perks like complimentary upgrades, bonus points and free food and drink that come with status. There are plenty of ways you can use credit cards to qualify for status faster, but these programs are well designed so that only frequent travelers (and in many cases high spenders) qualify.

Related: The best credit cards to jumpstart elite status in 2020

During college, I was blindly loyal to American Airlines which operated nearly a dozen daily flights between Chicago (ORD) where I was in school, and my hometown of DC. AA offered competitive fares, not always the cheapest but usually very reasonable, and I would receive an upgrade to first class roughly one out of every ten flights I took. But in order to lock in that marginally better treatment, I spent hundreds of dollars making sure I only flew American, even if the routing was less convenient or the ticket was more expensive. I had to spend a minimum of $3,000 every year to maintain my lowly AAdvantage Gold status, but once you get on the elite status hamster wheel, it’s quite addicting and thus hard to get off.

This is especially difficult if you primarily use miles to book your flights, as you don’t earn elite qualifying miles on award tickets. That’s why I gave up on earning airline elite status a few years ago (despite flying over 100,000 miles a year) and instead focused my efforts on maintaining my Marriott Titanium elite status. The good news is that Marriott, like most hotel chains, counts award nights towards your status qualification.

Getting upgraded to a suite with a bathtub in the bedroom is a pretty fun feeling, but these perks are reserved for frequent travelers who are able to qualify for elite status. Photo by Ethan Steinberg / The Points Guy

Earning points is easy, redeeming them takes work

When you read a TPG flight review, we focus heavily on the actual experience of the flight. What you don’t always see is the painstaking work it takes to find that one elusive award seat and book it. Anyone with a good enough credit score can open new cards and rack up miles, but knowing where to search for award space and which programs offer the cheapest rates take some serious effort.

Related: From newbie to advanced: 5 ways to up your mileage redemption game

As award travel has exploded in popularity, airlines have devalued their award charts and restricted the number of first and business class seats they make available for award bookings. In addition, frequent flyer programs with confusing IT systems take an advanced degree and a wealth of patience to navigate. As TPG loyalty and engagement editor Richard Kerr so aptly said: “Complexity is an everpresent devaluation.”

At the same time, you have airlines like American Airlines making it easier to book partner awards online. This means that many people might end up booking Qatar Qsuites, the world’s best business class product, without even knowing what a gem they stumbled on. When you add this all up, you’re forced to face the fact that just because you have enough points, doesn’t mean you’ll get to fly the airline/route/cabin/plane you want.

Which leads me to my final point.

You won’t get anywhere without a bit of flexibility

Back in college I moonlighted as an award booking consultant, helping people figure out how to use their points and miles to book the trips they wanted. I had clients come to me insisting on finding nonstop business class awards to Australia for their family of four in December, as well as award space at the Park Hyatt Sydney. Nothing else would work for them, they refused to budge. Of course you’d be lucky to find one business class award seat to Australia during peak times, but more likely than not you’d need to route through Asia to get it. Without flexibility, you’ll get nowhere.

This means you need to decide what matters most to you: the dates, the destination, or the airline/class of service. When I planned my monthlong vacation over Chinese New Year this year, I built the entire trip around the one day of the month that had two Etihad Apartment awards from Seoul (ICN) to Abu Dhabi (AUH). I had a vague idea of where else I wanted to go on the trip, but I didn’t care what order we made our stops in and I had a lot of flexibility with the destinations themselves.

If you’re traveling on a fixed schedule (around school breaks, for example), don’t expect to find multiple business class awards for your entire family. And if you insist on flying in business class, you might have to change your destination to one that’s less popular at that time of year. Points and miles open up a whole new world of travel, but there are limits to what you can do with them. Being realistic with yourself from the start will lead to less frustration and more high-quality redemptions.

Bottom line

The award travel community is a lovely cult family of people who’ve figured out how to travel like billionaires for pennies on the dollar just by optimizing their use of credit cards. I’ve made some lifelong friends through award travel, and had experiences I never would’ve dreamed of (let alone be able to afford) without points and miles. If you’re new to the world of points and miles you have an exciting road ahead of you, but a little bit of patience and flexibility will go quite a long way.

Photo courtesy of Four Seasons.

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