What I’ve Learned in 10 Years of Collecting Points and Miles

Jason SteeleDecember 19, 2019
On a similar note...
On a similar note...

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It was around 2009 that something in my head just clicked. I’d been reading about credit cards and the best ways to earn and spend points and miles. All of a sudden, I finally put all the pieces together in my mind — it felt like I’d cracked a secret code.

I recall my excitement when I realized that I would now be able to go anywhere with my points and miles. If I really put my mind to it, I’d never have to pay for travel again. By 2013, I’d become good enough at both earning and spending rewards that I’ve hardly paid for a flight or a hotel night in over 100 trips since then, often including my wife and our three kids.

So how did I do it? There’s no single, simple secret formula to award travel. I love the elegance of E = mc2, but I’m no Einstein and I can’t offer you anything like that. Instead, I can distill my success into the following tips, which I hope will help you get started too.

Earn your points and miles from as many different sources as possible

This includes credit cards, shopping portals and of course any travel that you pay for (hopefully reimbursed by your employer or client). And when it comes to credit cards, you should be regularly earning sign-up bonuses, and always using the card that offers you the best rewards for each kind of purchase.

At the same time, I’m always looking out for the promotions offered by airlines, hotels and credit card issuers. Over the years, I’ve received bonus points and miles for doing all sorts of things — from adding additional authorized cardholders to completing spending challenges.

Invest as much time in spending your points as you did earning them

I know too many people who just look at their points and miles as free money to be spent as quickly as possible on whatever appeals to them at the moment.

But I’ve learned to treat spending my points and miles just as seriously as I do earning them. For example, let’s say I have Chase Ultimate Rewards® points that I want to use for an award flight. Before I spend any of them, I first consider the award prices and availability of all 10 airline transfer partners offered.

If you think you can skip checking out many of the foreign carriers that don’t offer domestic service, think again — they likely have domestic partners. For example, British Airways Avios can be redeemed for flights on American Airlines, and Virgin Atlantic points are great for booking flights on Delta.

Finally, I check whether I can get a better deal redeeming my points through Chase’s Ultimate Rewards® travel portal, which offers 1.5 cents per point in redemption value to Chase Sapphire Reserve® cardholders, and 1.25 cents per point to those with a Chase Sapphire Preferred® Card or Ink Business Preferred® Credit Card.

Plan your award travel far in advance

While I just started to fully grasp the concept of award travel in 2009, it still took me until about 2013 to save up enough points and miles to pay for nearly all of my future airline tickets and hotel stays. That’s because award travel can take time.

For example, you can strategize about how many points or miles you might be able to earn in the next year and what you can redeem them for. Once you have those points, you’ll need to plan to book that trip for travel perhaps six to 10 months ahead of time. In total, it can often be two years between when I set out to take a great award trip and when I actually leave home.

Earn ‘em and burn ‘em

While you need to plan your award trips in advance, don’t take that advice too far to the extreme. Several times I’ve heard tragic tales of dedicated and persistent travelers who’ve spent years saving up their rewards for a dream trip, only to find that the airlines and hotels they planned on using raised award prices in the meantime, and their dreams were now out of reach.

These travelers learned the hard way that airlines and hotels are always devaluing their points and miles. Unlike investing your money, it’s not a great idea to accumulate huge stashes of points and miles over several years. Instead, you need to create short-term award travel goals that you can meet within a year or two, before travel companies have a chance to move the goal posts too far ahead.

Be flexible

I used to imagine that I’d earn my reward and then simply redeem them for the flights and hotels that I wanted. But that only led to disappointment, as I was rarely able to find exactly what I wanted.

Now, my family and I have readjusted our expectations. For example, if nonstop service exists to our destination, we’re still OK making a stop to get there if it means flying for nearly free. And even if it is possible to fly overseas with a single stop, we’re fine making two (again, considering we’re traveling for next to nothing ... and often in business class).

When planning an award trip, we also try to be flexible with our dates and destinations. That’s why I might plan a winter vacation by first looking for a hotel that offers a great redemption deal for our points. And my motto for a summer vacation is as long as we’re having fun in the sun, it doesn’t matter too much which beach we’re on.

Always be learning

Award travel isn’t like riding a bicycle; it’s not a skill you can just pick up and keep forever. Instead, it’s more like following your favorite celebrity or sports team. You have to constantly be looking for the latest information in order to stay current.

To do so, I read my favorite blogs and scan online travel forums. Even more importantly, I attend points and miles meetups where I’ve made friends who share my hobby. That way, we can help each other out and swap techniques that might not be published online.

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