The Joys of Planning

To the surprise of absolutely no one who knows me, I love to plan trips. Planning scratches a persistently itchy part of my brain. I’m a project manager both by profession and by personality. If a thing needs to be researched, organized, and executed, all my friends need to do is mention it in my presence and they can consider it done. A coworker once said, “On my lawnmower back home, there are two speeds: turtle and jackrabbit. You’re stuck on jackrabbit.” Folksy, no? In short: Type A, as pop-psych-silly as such things are, pretty well covers it.

But beyond my general love of reading, comparing, and putting the pieces together, I enjoy planning trips specifically because it’s almost like starting the trip early. I may be sitting on my couch in Chicago as the days get shorter and colder and grayer, for example, but on my computer screen are photo after glorious photo of Caribbean beaches and pastel-colored hotels. It gives me something to look forward to and get excited about, especially if other people are going on the trip with me. We send links back and forth about possible excursions to go on, see which bands are playing while we’re in town, and keep a close eye on the weather as the trip gets closer to figure out which is the right day for a ramble through the park and which is the right day for museums. Every conversation about what we’re going to be doing in x number of days gives me a little spike of happiness, a teaser for what’s about to come and a little carrot dangling just in front of my nose to urge me on through the grind of work and chores and boring home-bound obligations.

Too much planning can be dangerous, of course. It’s so easy now to get the crowdsourced opinion on where we can order the best pesto in the Cinque Terre or see 360-degree video tours of the rooms we might eventually sleep in. But seeing every view and menu online means less delight and surprise when you actually show up and see it in real life. And having every moment planned out means less room for the spontaneous adventure of wandering down that side street just to see what might be there.

But if you can restrain yourself from digging down into every last detail and can limit yourself to daydreaming only an hour or two a day (I find 10-11 and 2-3 are the best times for this, while staring at a flowchart that I’ve refined past the point of usefulness), then some smart planning both improves and extends your vacation. And if someone tells you you’re stuck on jackrabbit just because you’ve looked up a few good options for breakfast and dinner every day, just nod and smile and picture yourself sitting on that cafe’s rooftop deck enjoying their signature French toast, secure in the knowledge that your planning will pay off.


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  1. Pingback: How To: Judge People Based on Their Travels | Go Go Go

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