Recently, my wife and I were booking a trip. While it was within our budget, it was definitely pushing it, and I started experiencing discouragement. Then, my brain suggested one option that I’d learned a few months ago: the best way to save money on a trip is to be flexible in timing or in location.

I learned this from skimming Take More Vacations by Scott Keyes, the founder of Going (formerly known as Scott’s Cheap Flights—more on the rebrand, there’s a post on naming worth having here, as I’ve noticed with Joe’s Pizza and John’s Pizza here in NYC). 

I’d subscribed to Scott’s Cheap Flights for years, and I was interested in learning more about how he thought about the process. Scott’s actual words were:

There are dozens of variables one could consider essential or flexible when looking at flights, but for most people it boils down to three primary factors: 

• Where to fly? 
• When to go? 
• When to book?

While my wife and I had a location in mind, we could be flexible with timing, so we started futzing around on Google Flights and for lodging, and after half an hour—voila!—we found some dates that saved us a lot of money. Same places, similar flights, for much less. We also took advantage of a longer stay option that bundled in a free night.

One thing I learned this year, which Shane Parrish made very clear in Clear Thinking, was the power of not asking people what they think, but how they think. In other words, you don’t want to just abdicate your thinking to them and have them recommend what to do—but how they thought about it. It definitely takes more effort and intentionality; sometimes, this will be very expensive if you need to pay an expert to ask them directly. You’ll also probably be doing more of the execution work yourself; but your results will turn out better. (In his example, Shane gives it ten-to-one odds that your execution turns out better if you figure out how somebody else thinks about a problem and apply the principles yourself, than simply to do what somebody else recommends.)

But sometimes, like this one, this can be relatively cheap, especially if the expert has written a book on it. You might skim it like I did, or you might be willing to pay with your time to read the book (or listen to the audiobook) multiple times.