I needed to book two trips for the coming month, one to Europe and one to Mexico. I was concerned about jet fuel prices, and indeed, the airfares were strikingly higher than the last time I looked. I thought about holding off.

That's when I remembered Going.com, a site I'd signed up for a couple of years ago but never used. Formerly Scott's Cheap Flights, Going pings you a few times a day with flight deals. You can tell it where you want to go. It tells you when the fares drop. Historically, I'd ignored the alerts. The deals were always to places I wasn't going, on dates that didn't work, or mistake fares that disappeared when you tried to book.

This time was different. I pulled up the two destinations I planned to visit and found special fares on both routes. Real deals. Business class tickets for a third of the going rate. These weren't the dates I'd originally planned, but the price difference was so substantial that I rethought each trip. The dates worked. The price dropped. It was worth it.

Of course, this kind of flexibility isn't available to everyone. School schedules and work calendars are real constraints. But sometimes the calendar has more give than we assume. It's worth looking.

The travel industry has it backward. Instead of building tools that reward flexibility, it penalizes it. Algorithms push you toward rigid itineraries. Booking sites assume you know when you're going. What if more platforms made flexibility the default? Tell them you can go anytime this month, and let them tell you where the deals are. Going.com does this. Most don't. They could.

Once you arrive, flexibility matters even more. Leaving afternoons open. Finding restaurants instead of researching them in advance. Saying yes to the side road.

This month's trips are booked, but not the same way. The dates are set. Everything else is open. I plan to do more of this.