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Welcome

Friends,

It is April fools day, but this message is serious.

Or at least as serious as you can be when writing about a fiat currency airlines, hotels, and banks make up to incentivize us all to spend money with them.

455 words—let’s get going.

Links

The new British Airways Club went live today; I wish that was an April fools joke.

Twelve hour flight from New York to Tokyo Dallas.

This article is a little gimmicky, but I am eager to try PS.

New SkyTeam domestic lounge access policy is live.

Story

I may never say this out loud, but it is true: points are like bananas—they don’t get more valuable over time.

Airlines and hotel programs devalue.

Award charts change or disappear. Availability goes away. And what feels like “saving up” can easily turn into “I should’ve used those months ago.”

So, when I’m thinking about booking a trip with points, here are the three questions I like to ask:

1. Would I pay cash for this?
If the answer is “no,” that’s not always a dealbreaker—but it helps frame the value. If I’m about to drop 180k points for something I wouldn’t pay $2,000 for in cash, I pause. But if the cash price is $6,000? Easy choice.

2. Is this a good use of points—or just an option?
Availability doesn’t always equal value. I check award rates, compare cash fares, and aim for that sweet spot between practicality and stretch. No need to “maximize” every cent, but don’t throw points at a bad redemption just because you can.

3. Does this make the trip more possible—or more fun?
That’s the big one. Points that unlock a trip—or turn a good one into a great one—are points well spent. Especially if it means we get to go, stay, or fly in a way we wouldn’t otherwise.

Sometimes I burn points just to avoid a $700 charge. That’s okay too. They’re meant to be used.

Big Picture: Points are tools, not trophies. The best use is the one that works for you, and the wisest move is to use them well—before they lose value.

Happy flying.

Remember, this life you are living has meaning. Thank you for reading. I am grateful you are here and would love to hear from you. If you'd like to write me a note, simply reply to this email. Otherwise I'll see you in the next one.

Be well today. -Tommy

P.S. If I can ever help you plan your next travel adventure (slash help make your points go farther), I’d be delighted. You can schedule time together here.