Last week, Esther and I were trying to figure out the best use of our points for an upcoming trip to Australia, New Zealand, and Fiji. I had initially covered four nights in Sydney with my IHG balance (140,000 points for 4 nights at the Holiday Inn Old Sydney), and we planned on redeeming Orbucks for our stay in New Zealand, so we were left trying to figure out what to do about Fiji.

After some research, Esther settled on the Intercontinental Fiji, and it’s not too hard to see why:

Source: ihg.com/intercontinental

Source: ihg.com/intercontinental

However, we were faced with a complication: having redeemed 120,000 points for Sydney, I was out of IHG points, and Esther had no balance to begin with. So even though 30,000 points/night is a great deal for what would have otherwise been a $500/night hotel, we didn’t really have a way to make the redemption.

Luckily, Esther has gobs of Ultimate Rewards (UR), so she suggested transferring them to IHG so that she would have enough of a balance to make the redemption we wanted. That seemed reasonable to me, too.

Except….Nominally, UR transfer to IHG at a ratio of 1:1. I say nominally because that’s only what Chase tells you. In actuality, you can get 1.43 IHG points for every UR you’re willing to part with.

I’m not going to go into the mechanics of the hack (you can see posts here and here if you want to learn more), but suffice it to say that at any point in time, you can buy 10,000 IHG points at a cost of $70, which is 0.7 cents per point. How does this help us? Well, if we redeem, say 7,000 of our UR points as cash, we can then go buy 10,000 IHG points. Working out the math, 10,000/7,000 = 1.43, giving us the ‘transfer’ ratio I promised.

But you knew this. It’s just a reformulation of a hack that you’ve already seen, with a photo of a nice hotel thrown it. What’s the point?

An Ultimate Rewards point is strictly better than a penny.

The point has nothing really to do with IHG. The example above was just a conceit to show how one thing (UR) could be strictly better than another (cash). It is strictly better because all of the advantages of a penny can be had by an Ultimate Reward point, and an Ultimate Reward point has advantages that a penny does not, namely, the ability to get outsized value for nice hotels (Hyatt) or flights (Singapore first class suites).

Can we think of other examples? Here are a few.

  • An Apple gift card is strictly better than an iTunes gift card, since you can buy an iTunes gift card with an Apple gift card, but you can also buy an iPad with the Apple gift card but not with an iTunes gift card.
  • A Membership Rewards point (MR) is strictly better than a Singapore KrisFlyer mile, since the MR can be converted to a KrisFlyer mile while also being redeemable for 0.5 cents or transferrable to another airline partner.
  • The Yankees are strictly better than the Red Sox because, well….26 rings.

What are situations in which something is NOT strictly better than an alternative?

  • A grocery store gift card is not strictly better than a gas station gift card if that grocery store card can’t be used to buy other gift cards.
  • A Starwood (SPG) point is not strictly better than cash because while you can redeem SPG points for hotels or flights at greater than 1 cent per point, those points offer you no value at IHG hotels, whereas cash can buy you the points for a discounted stay at the Intercontinental.

Now that you’ve gotten the hang of it, let’s try to articulate what makes one thing ‘strictly better’ than another. The better-ness has to do with opportunity. What things or experiences are we afforded by having one point/mile/widget/currency over another? If the answer is, “all, and then some”, then you’ve found something that’s strictly better.

‘Strictly better’ is a framework for making decisions.

The formal term for the property we’re describing is total order. A set of things are said to have a total ordering if you can arrange them in such a way that each successive item is provably ‘better’ than the previous one. Therefore, since a penny is strictly better than an IHG point, and a UR point is strictly better than a penny, the set of IHG points, cash, and UR have a total ordering.

What this means is that when faced with two alternatives, like using a 2% cash back card at a restaurant or your Chase Sapphire Preferred which earns 2 UR per dollar spent, you should never opt for an alternative that is strictly worse than the other. In other words, you should always use your Chase Sapphire Preferred (at restaurants).

When two things don’t have a strict ordering, the decision-making becomes less cut-and-dry. For us, these sorts of decisions take the form of deciding which of two currencies we’d prefer–for example, 5 Club Carlson points per dollar at a grocery store or 6 Hilton points–the answers to which can only be supplied on a person-by-person, case-by-case basis. Clearly, Hilton points have no use at Club Carlson hotels, and Club Carlson points have no use at Hilton properties, so you’re forced into a different question. What’s a Club Carlson point ‘worth’ to you? A Hilton point? Only after a long inner dialogue can you make this important decision.

To be clear, I don’t think you should spend hours, minutes, or even seconds agonizing over each and every decision in your life, because for the purposes of most of us, a 1% difference in return is completely inconsequential. But the next time you get offered an option of $100 cash or 20,000 IHG points as I was two weeks ago, at least you’ll know where to start (hint: $100 cash is only strictly better than 14,285 IHG points).

Happy hacking!