The Risks of Overthinking Your Points

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Ever found yourself staring at a solid points redemption—a free flight, hotel stay, or rental car—only to hesitate? Maybe it’s the voice in your head whispering “Is this really the best use of my points?” Or worse, it’s some self-proclaimed expert online telling you you’re making a mistake.

• “You should save your points!”
• “You’re only getting X cents per mile—it’s not worth it!”
• “You could earn more points if you just paid cash!”

Sound familiar? Yeah, me too. But here’s the thing—miles and points aren’t meant to sit in your account gathering virtual dust. They’re meant to be used. And sometimes, the smartest move isn’t chasing the perfect redemption—it’s booking the trip you need.

Let me share two examples where I almost overthought my redemptions—but ultimately made the right call

1. Delta SkyMiles – A Flight to New York

Delta SkyMiles aren’t exactly the most valuable currency, but they’re easy to earn and use. So when I needed to book flights to New York for an upcoming trip, I turned to my stash of SkyMiles.

Delta offered main cabin tickets for 7,000 SkyMiles + $5.60 in taxes each way. The cash price? About $90 per ticket.

But that’s the Basic Economy price. We’ve flown Basic Economy on Delta, and while it wasn’t bad (Note from Joe’s wife: yes, it was), it’s not for us.

Main cabin seats cost an extra $35, and that’s the price we’ll pay if we pay for seats. Here’s the math:

• Cash price – $124
• Award Price – 10,000 SkyMiles + $5.60
• ($124 / 10000) x 100 = 1.24 cents per Delta SkyMile

1.24 cents per point for SkyMiles isn’t bad—it’s not bad at all. Ben from OMAAT currently pegs Delta miles at 1.1 cents each, so this would be an average redemption. But I hesitated. Why? Because it wasn’t a flashy, aspirational redemption.

Then I reminded myself—SkyMiles are easy to replenish with a Delta Amex sign-up bonus or Amex Membership Rewards transfers. The alternative was to pay cash for a flight I had to take anyway. So I booked the flights, and you know what? I don’t regret it one bit.

2. IHG One Rewards – A No-Brainer Hotel Stay

I’ve long felt that the IHG Rewards Club program matches our travel style better than any other loyalty program out there. My huge stash of Marriott Bonvoy points and my wife’s Platinum status have steered us toward their hotel, but we still stay with IHG when it’s a good option. That’s what happened during our pre-cruise stay in Miami.

The Intercontinental Miami was charging $350 per night for a room, which is more than we’d usually pay. However, award nights were going for 49,000 points.

• Cash price – $350
• Award Price  – 49,000 IHG points
• ($350/49000) x 100 = 0.7 cents per point

IHG frequently sells points at 0.5 cents each, so on paper, I wasn’t getting an amazing deal. But here’s the thing—I bought these points during a recent sale knowing that I’d easily find a use for them. And rather than hoarding them for some hypothetical future trip, I used them for a stay I actually needed. Plus, thanks to my IHG Premier card, I got 4,900 points refunded, making the deal even sweeter.

Final Thoughts – Spend Your Points!

After both redemptions, I didn’t feel a hint of regret. I saved nearly $600 on travel expenses using points just sitting in my accounts. And let’s be honest—what’s the point of collecting miles and points if you never use them?

So the next time you find yourself agonizing over whether to redeem, take a deep breath and just do it. Miles and points are a tool, not a trophy. Don’t let them sit idle while you wait for some mythical perfect redemption. The best use of your points is the one that makes sense for your actual travel plans.

Now, go crush that hesitation and book the trip!

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