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Dear Dan,

I'm shopping for several plane tickets for personal trips over the next couple of months, and I keep running into the same problem: "Current me" wants to pinch pennies by choosing overnight flights, routes with several legs or inconvenient airports that would require me to drive a few hours out of my way. "Future me"—the one that actually has to pick up the rental car at 11 p.m. and drive two hours from Phoenix to Tucson the night before a friend's wedding—sometimes resents that I wouldn't just spend an extra $100 to make an already expensive trip more pleasant. Travel-booking websites are getting better and better at predicting what will happen to flight prices, but I don't seem to have gotten any better at predicting my own preferences.

How can I best determine whether these savings will feel worth it to me in the future? Or, failing that, how can I console myself when I'm pulling into a Tucson motel parking lot at 1 a.m.?

—Ruth

Your framing of the problem is spot on. In your current "cold" state, you focus on the price, which is clear and vivid and easy for you to think about. When you actually take the trip, that version of you will be feeling exhaustion and need for sleep (a "hot" state), which will be very apparent to you at that point—but it is not as vivid right now.

This, by the way, is a common problem that arises every time we make decisions in one state of mind about consumption that will take place in a different state of mind.

Here is what I recommend. In order to make a better decision, tonight at 9 p.m. put in some laundry and spend the next two hours sitting on the washer and dryer (this is to simulate the fun of flight, and if you want to really go all out, supply yourself with a package of peanuts and a ginger ale). When you "land" at 11 p.m., look around for some missing socks (to simulate looking for your luggage) and then, properly conditioned to think about the actual trip, log into the travel website and see what is more important to you: saving a few bucks or getting to bed sooner.

Plus, imagine how you would look in the wedding pictures after a long night of uncomfortable traveling.

Good luck in your decision and "mazel tov" to your friend.

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