Don't let the planning eat the trip

We’re a little obsessed with planning the family trip. That’s sort of the whole brand. But there’s a failure mode hiding inside the points-and-miles world, and it’s worth naming before it gets you, because it got us for a while.

Chris Hutchins calls it the optimizer’s curse, and the first time we heard him describe it on All The Hacks we both laughed, because it was us. His version: he’d spend three hours hunting the perfect flight redemption — only to realize the family wasn’t even going to take that trip. His wife once asked why a simple “which flight should we book” had produced a 47-row spreadsheet.

We’ve been in that spreadsheet.

The point of the points

Here’s the thing it’s easy to lose. The reason we play this game at all is so we can go more, and go with the kids while they’re still this age. The points are supposed to buy us time — more trips, less spent on airfare. The moment the optimizing starts eating the very evenings we’d otherwise spend with the girls, the math has quietly flipped on us. We’re now spending the most valuable thing to save the least valuable one.

The rule

Hutchins’ fix is the one we use now, and it’s almost embarrassingly simple: set a threshold below which you stop caring. Early on, ours was low — if I could save twenty bucks, I’d keep digging. Now it’s higher. If the extra hour of searching is going to save the family a hundred dollars, fine, sometimes that’s worth it. If it’s chasing the last few thousand points on a redemption that’s already great, close the laptop.

And the harder discipline: don’t price your free time. It’s tempting to run the “this hour of research saved us $80, so it was worth it” calculation. But that logic, followed honestly, tells you to optimize every minute of your life, and that’s a miserable way to live. As Hutchins puts it — does it cost a thousand dollars an hour to play with your kids? That’s not a real question. So don’t ask it about the trip either.

Good enough is the whole skill

The travel hacking is worth learning. The cards, the sweet spots, the free nights — they genuinely fund our year, and we’ve written the whole system down. But the most advanced move in the entire game isn’t a redemption. It’s knowing when you’ve found a great deal and choosing to stop, book it, and go pack.

The deal was never the point. The trip was.