Have You Written Your "Trip Goals"?

Let me ask you a question: when you go on vacation, do you plan out each day, hour-by-hour? Or do you fly by the seat of your pants, letting chance and emotion guide you?

Surely those are the ends of the spectrum, but their gravity is strong; the middle of the spectrum is largely unpopulated. People tend toward regimented planning or they tend toward the complete absence of forethought. It needn’t be that way.

Out of great fear for offending (or enraging) someone I know, I will resist the urge to dive into a deeply amateur psychoanalytical exploration of the two camps. You know who you are, and you probably also know why.

When I travel, I try to establish myself in that elusive middle ground.

For those of you wed to one extreme or the other, you might be more apt to call my method “controlled chaos.”

The cornerstone of my approach is a clear set of Trip Goals. Sounds banal enough, but it’s more powerful than you might think.

Goals might consist of
a.) places to see
b.) things to do
c.) people to meet
d.) food to eat
e.) photographs to take
f.) paths to walk.

One can surely devise additional categories, but you get my idea plainly enough without the exhaustive list.

Now here’s the tricky part: for any given trip, no matter the destination, you must define a set of goals that do not exceed twice the number of days you’ll be in the place (round up: partial days count as full days—there’s no need to get into fractions). For a three-day trip you cannot have more than six goals. Emphasis on CANNOT.

Let’s say that you’re going to visit Boston for three days. Your goals might look something like:

1.) Chant Yankees Suck at the Red Sox – Orioles game
2.) Scout obese squirrels during a tour of Harvard Yard
3.) Throw back a beer at “Cheers”
4.) Chow cannoli from Mike’s Pastry in the North End
5.) Dine on the tasting menu (with caviar add-on) at L’Espalier
6.) Watch as Normal Guy and Girl kick the hell out of you and your significant other at Jillian’s on Lansdowne

Not a bad set of goals, really. Does it mean that you can’t stop in for a cup of chowder at Legal’s or walk the Freedom Trail or go shopping around Faneuil Hall? Of course not.

But it does mean—and this is important—you can’t get upset (at anyone, including yourself) because you didn’t have that cup of chowder. It wasn’t on your list, and anything you do above and beyond the list is whipped cream on your three-day sundae.

For many years, I created such lists in my head and executed this approach without formalizing it. I found that my days were freer, and I accomplished more. I felt less pressure to wake to an alarm, except where I wanted to. On more structured trips earlier in my life, the rigor of schedule dictated rising at the buzzing of an alarm, showering and dressing in a hurried flash, and arriving someplace super early…only to find I was completely useless before three o’clock.

And then I found myself in the throes of the vacation death spiral: the exhaustion of day one spilling over into day two, the exhaustion of day two carrying into day three, and so on, until the last day you actually look forward to getting on the plane home. What kind of vacation is that? None I want to take.

Now I put those goals on paper and enjoy myself… The anal retentive part of me smiles each time I can cross an item off my list, while my Bohemian side revels at sometimes sitting an extra hour in a random café that I had never heard of before bumbling onto it.

In coming weeks, I will be logging my Trip Goals for each trip Normal Girl and I take…

Maybe it’s a crazy idea. Or maybe you think it’s lame and obvious. Let me know…

- Normal Guy