Planning and Regret

by Steve Brock on February 1, 2011

If you're going someplace popular or for a special occasion (like our 20th anniversary shown here), without a reservation you might end up with a healthy serving of regret...

The anticipation phase of travel is normally a pleasant, even exciting time of dreaming and imagining what our trips will be like.

But the pre-trip phase also can be stressful, mostly as it relates to planning. Planning often elevates our blood pressure because we have to decide on issues that can potentially make or break our whole travel experience. That puts a lot of pressure on planning which may be why I get as thrilled about the words “planning and reservations” as I do the words “large SUV, soccer mom, cell phone and driving” when used in the same sentence or experienced on the road.

But planning also has its benefits, most notably as an antidote to regret. We’ll get to that momentarily, but let me start by explaining why I believe in making certain kinds of reservations before a trip even though my personal preference would be to book a plane ticket, never deal with other reservations, hit the ground running and figure it out as I go.

First, I usually travel with others who may not have as much of a tolerance for spontaneity. Also, my own tolerance for winging it depends on the location and how easily I feel I can find transportation and places to stay in-country.

Second, I have limited time and a limited budget. Spontaneity and traveling without plans usually require the flexibility provided by time or money…or both.

Third, if we don’t make reservations, when we arrive at our destination, we may not be able to do some of the things we dreamed about because they are booked by others who did make reservations. For example, we’re currently planning a trip to Peru. If we were to go in the high season and wanted to hike the Inca Trail to Machu Picchu, without reservations booked a good six months ahead of time, we likely would not be able to do the hike due the limited number of slots available.

Fourth, planning helps you avoid regret because you’re mentally able to assure yourself that you did all you could ahead of time so that if you miss out on something later on, it wasn’t your fault. That may sound like a mind game…because it is. But it is also a very real phenomenon for many travelers.

Studies show how we repeatedly go to great lengths to avoid regret. But the most interesting thing about regret is that we tend to regret most the things we did NOT do rather than those we did. This is why some of the most common regrets in life are missed job or business opportunities, not going to college or not investing enough time with the people who matter most to us.

With travel, if you make a reservation and the room is bad, you’ll likely regret that far less than if you don’t make a reservation and then arrive to find that the city is holding simultaneous conventions for bipolar clowns and pedigree Whippet owners, all of whom have booked every available room in the area for their pets, costumes and alternative personalities.

So the next time you feel that planning and reservations take all the fun and spontaneity out of a trip, think about how much they can help you. And with the 24-hour or so cancellation policies many hotels and tours offer these days, you can get the best of both worlds: you can lock down a hotel room to avoid regret while still keeping your options somewhat open.

That way, once you arrive at your destination, you might find that quaint little B&B with an available (and affordable) room so you don’t have to stay in that big chain hotel with all those clowns.

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