- Tommy Obenchain
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- The Biggest Mistake I See People Make with Points
The Biggest Mistake I See People Make with Points
(TLDR: go somewheređđź)

Friends,
Tonightâs post is short and sweet, but if youâre sitting on a pile of points, I hope itâs helpful.
Hereâs the biggest mistake I see people make with points and miles:
They donât use them.
It sounds obvious, but itâs true. Points are a currencyâexcept unlike dollars, they lose value over time. Airline programs devalue, hotel award charts change, and sweet spots quietly disappear. Waiting for the "perfect" redemption can turn great opportunities into wishful thinking.
In my view, points are meant to be tools â not trophies.
When you use points wisely, you unlock experiences you might not otherwise justify. Business class to Europe. A beautiful hotel in Hawaii. An upgraded weekend getaway with your family. Youâre taking something virtual (a number in a loyalty account) and turning it into something tangible: real memories & experiences.
And yesâthere are times when itâs smart to save points for a larger trip. Iâm not advocating reckless redemptions. But perfect is the enemy of great. A good use of points now almost always beats a theoretically better use years from now.
I recently booked an economy flight to Washington on points that âwasnât the best redemptionâ according to some calculators. But it saved me cash, simplified my trip, and freed up margin for what matters more to me: time with my family. Thatâs a win every time.
Big Picture: Points are meant to be used. Donât let perfectionism (or hesitating for âone dayâ) rob you of real experiences.
Turn those numbers into momentsâand enjoy the trip.
Fly well.
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Links
Ryanairâs social media team ⌠makes me want to fly Ryanair.
Tariffs (evidently) delay Deltaâs new business class bedding.
New points platform with no travel company attached: I am skeptical.
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.

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