Third-Party Services for Buying Trips

#670: As we close out 2025, premium credit cards are more expensive and more complicated than ever. It’s fair to ask whether the points game is still worth the effort.

We sit down with Chris Hutchins, host of All the Hacks, to talk about what’s changed in credit card rewards, and how to decide whether to stick with travel points, switch to cash back, or run a hybrid strategy that keeps your life simple.

We dig into the “value” problem behind all those new credits and perks. Instead of letting a card dictate our spending, we walk through how to price credits based on what we would genuinely pay for them, and when it’s smarter to downgrade, negotiate a retention offer, or product change and keep your credit history intact.

We also get tactical about booking travel in 2026: newer award search tools, how much flexibility matters, and a sneaky alternative most people forget, sometimes you can buy points directly and still get a strong deal without years of “earning.”

If you want to earn more points (or waste less time chasing them), this conversation will help you reset your credit card strategy for 2026 with a clearer definition of what “worth it” even means.

Key Takeaways

• “Credits” are not value unless we were already going to buy the thing, and we’d happily pay close to face value for that discount
• The points game is still powerful, but mostly through welcome offers, not micro-optimizing bonus categories
• Flexibility is the hidden lever in award travel, the best deals often show up when we loosen the date, airport, or destination constraints
• Cash back is having a moment, especially if we want simplicity and fewer mental tabs open.
• Before canceling a fee card, we can often negotiate, downgrade, or product change and keep the credit history we’ve built
• Sometimes the best move is to stop “maximizing,” take the trip, and protect our time for higher-impact work (or actual rest)

Resources and Links

• Chris Hutchins, All the Hacks (https://www.chrishutchins.com)
• Our deep dive on credit reports and scores, Episode 221
• YouTube video mentioned on why airline loyalty programs can be worth more than the airlines themselves
• FlyFlat.com
• Seats.Aero
• Point.me
• Rome Travel
• AwardTool.com
• PointsYeah.com Daydream Explorer

Chapters

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(01:22) The 2025 reset for premium credit cards

(06:18) How the points game actually works in 2025

(10:29) Rethinking economy flights versus business class

(16:37) Managing credit cards during major life transitions

(23:57) Simplicity versus optimization in the points ecosystem

(36:45) Luxury perks, rising fees, and who premium cards serve

(43:34) Buying points directly instead of playing the game

(58:44) Using AI and systems to build better money habits

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