Quit Planning & Just Do It!

For as much as a planner as I am, I’m currently en-route to Montego Bay, Jamaica with absolutely no idea where I’ll sleep, eat, or how to get from one place to the next.

I travel a lot, but almost always at least somewhat planned. I’ll at least purchase plane tickets more than 3 days ahead or book a hotel or hostel room for a night or two (or know which friend’s couch I’m crashing on). Sometimes I go all out get guide books ahead of time and make a list of all the places I want to see with an hour-by-hour itinerary. Most of the time, however I’m visiting friends and just let them lead the way.

I thought about planning a relaxing week-long Caribbean vacation a month or two in advance, bringing friends nd family, and just having an all-around chill time on the beach. But planning is harder than you think. You have to coordinate with everyone else’s schedules (“Oh, that week won’t work: I have an assignment due the day after” or “Well I’d rather go in off-season than high season”). You’re constantly searching for a better deal (“Yea that’s a nice beach house but I think we could get a better one for cheaper, let’s wait”). There’s often a sense of “analysis paralysis” (thinking about doing something and analyzing all the options so much that you end up doing nothing at all).

A few weeks ago I gave up on the search for a Caribbean destination vacation. So when a friend who I just recently volunteered at Bonnaroo with said he booked a flight to Jamaica for 5 nights and asked if I wanted to come, I thought about it for about 2 minutes and blew it off as too impulsive or crazy. Then he said he was serious and gave me his flight itinerary.

Hmmm. I checked my calendar: just work. Work will go on without me. I could actually go if I wanted to. I threw the question out to the twitterverse and got a resounding, “Just go! You’re only young once!”

Analysis paralysis could have set in but in didn’t let it this time. I booked the flight. And THEN I started asking my friend questions like “where are we staying?” and “what should I bring?” to which he responded “I don’t know” and “a little bit of everything, but small enough to carry on your back”.

So here I am trying a new type of travel. Not exactly the relaxing, reading on the beach all day trip that I imagined, but as long as I don’t die I hope I learn something. Again.

So your turn. Have you ever just booked a flight without any other plans? Have you tried a new kind of travel experience that you wouldn’t normally try? And what did you learn about yourself from it?

See you all in a week!