We’ve all been there.

Usually sometime in December, you get a piece of mail… that looks like junk at first glance… but then you notice it has a membership number on the front.

You open it up to find it’s about your travel points — usually with an airline or hotel. And those points are expiring!

You can either use them in the next two weeks… or lose them forever.

And that’s how you wound up with that subscription to Men’s Health you never read.

Loyalty reward programs have been around for a long time. And they’ve been screwing customers out of their hard-earned points for just as long.

At least that’s true of a lot of the loyalty rewards programs centered around travel.

Retail stores tend to let loyalty reward points live a long time, if not forever. Same thing for supermarkets.

And of course, any credit card points program worth its salt won’t let your earned reward points expire under your nose, either.

Since so many travel rewards programs are linked up with credit cards, that provides us a nice opening to capitalize on…

You see, you can bank your points on your credit card and then spend them through any linked rewards program.

Which can often make sense. After all, once you get enough points from, say, an airline, you might get a big bump in benefits — benefits you can only get through the airline’s rewards program, instead of your credit card’s.

So there are times when it makes sense to transfer points from your credit card to a loyalty program.

Of course, the benefits programs offer… the cost of anything in points… the exchange rates between different programs… all those things are in constant flux.

Exactly when you should transfer points between your credit card and a loyalty program will be a highly individual decision — based upon what credit card you’re transferring from, what loyalty program it’s going to and what benefits you’re hoping to realize.

With that in mind, you should always do your own homework to ensure you’re using your points to maximum effect.

What follows are the best guidelines to let you know when to pull that trigger.

Wait for the Golden Ratio

Life would be much simpler if everyone used the same point scale and every point in every program were equivalent to all others.

But that’s not how life works.

Some transfers between a credit card and a loyalty program will give you same points — a one-to-one ratio. Others will be two-to-one. Or 10-to-one. You’ve got to check your own credit card to find out (and those ratios can change).

But it’s not as simple as only using one-to-one transfers exclusively…

Maybe that program that transfers at 10-to-one does so because their entire scale is 10 times smaller. So a flight that would cost 10,000 points through your credit card would only cost 1,000 points through the rewards program.

In that case, the 10-to-one ratio is really a disguised one-to-one.

Bottom line — only send your points where they’re worth at least as much as they are if you spent them through your credit card rewards programs.

That will take a little comparison shopping, in addition to knowing the transfer rate, but it’s obviously worth the time.

Hit Your Plateaus

Lots of loyalty rewards programs have added benefits that come when you hit certain thresholds.

For instance — Southwest will give you free companion passes for a year when you get enough rewards points. Delta will let you into their airport lounges and give you free seat upgrades and the like when you reach a certain number of points.

And in many cases, transferred rewards points are just as good as those earned traditionally.

If you’re near hitting a new level of membership in any of these programs — especially a new level with practical benefits you’ll use often — it can be worth it to transfer points to take you over the top.

That’s all the more true if your counter goes back to zero.

Using Southwest as an example again, while your points can stick around for a while, they only count toward extra membership benefits when they’re earned in a single calendar year.

Make It the Last Thing You Do

As I mentioned, loyalty program points don’t last forever. Once you transfer points out of your credit card, you’ve started the clock.

So wait until the last possible moment. You might think you’ll buy that deal on American Airlines down to New Orleans for Jazz Fest… but unless you’re prepared to hit “order,” don’t transfer your points.

Something could come up that keeps you in town… Another airline might lower their prices and suddenly be the preferred option… Your rich cousin might rent a cottage on a ski mountain in Utah and invite you for the week…

Who knows. Plans change. And (loyalty) points expire. Don’t ever transfer your points unless you know what you’re doing with them — and can do it immediately.

Bonus! Double Your Points Everywhere

Here’s a little secret very few people ever talk about. In fact, you’re probably doing it on occasion without even realizing it.

But when you know what you’re doing — and you do it on purpose — you can really maximize your rewards.

Simply double up your rewards points. Everywhere. It’s easy.

All you have to do is sign up for rewards and loyalty programs wherever you shop (excluding programs that charge membership fees or that require exclusive licensed credit cards).

Then make sure you collect rewards for each of your purchases. You just have to be signed into your account when you pay to collect your points from the merchant. And if you make those purchases with your rewards credit card — you’ll get your helping of points there too.

Doubling up can really make a big difference, if you do it all the time.

Here’s an example… Let’s say you’re flying on Delta. For every dollar you spend on Delta, you get five miles.

(Each mile is actually worth more than a dollar if you spend it on Delta flights, but for the sake of simplicity, let’s just say that’s the equivalent of getting 5% back.)

But! You paid for the ticket with your credit card — mine gives 3% back for any money spent on travel.

Now you’re up to 8% cash back. Without any sales. Without having to jump through any extra hoops.

And if you transfer your credit card points to Delta and spend them judiciously, you can easily inflate that to something more like 10% cash back. Plus, you’re getting yourself closer to the Delta Sky Club, with free upgrades and lounge access.

Bottom line — there are plenty of rewards out there.

If you’re smart, you can get a 5–10% discount on all your spending in the form of rewards points. (Picture how nice it would be to get a 10% raise — it’s a lot like that.)

And you can get pampered like the elite at the same time.

It does take a little homework — and a little extra time and effort to figure out when a transfer makes the most sense for you.

But boy, is it worth it.

Unconventionally yours,

Ryan Cole

Ryan Cole
Editor-in-chief, Unconventional Wealth

P.S. Don’t have a great rewards credit card yet? Don’t fret — you can find a list of them from our partners here. Remember that rewards rules and options are always changing, so see what each card will give you today. UCW is not recommending any specific card or bank — especially since their rewards might change before you get this. But we absolutely do recommend you get the right rewards card for you off the comprehensive list here.

Ryan Cole

Ryan Cole is the editor-in-chief of Unconventional Wealth. He’s been covering the alternative investment space for nearly a decade and writing about finance and investment for almost 20 years.

Ryan has walked the walk for years, living a very unconventional life. He’s led snowmobile tours through the mountains of Colorado, settled in Japan for five...

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