I suck at traveling and I love it

I think one of the reasons why I love traveling so much is because I'm so bad at it.  When I say I'm bad at it, I mean that I hardly ever see everything there is to see, I never have a plan, and I often miss things.  But to me, that's a good thing; to me, traveling is about adventure and discovery.  I love the idea of going some place and having a spontaneous adventure, wandering around with only the vaguest sense of direction and location, and discovering little hideaways along the way.  I like to say that only through getting lost do you really discover yourself, and that's the outlook I have whenever I travel some place new.

So my "plan" is usually to go out to a location, and just sorta go from there.  A few weeks ago I was in New York for the first time in decades.  I just hopped on a subway and rode, all the way to the Metropolitan Museum of Art, which happened to be closed that particular day (like I said, I'm hardly a planner).  I didn't have a plan B, so I just winged it.  I walked around the Upper East Side, called and texted New York friends for cool eats in the area and took pictures in Central Park.

But it's not just about sights, but about the people you meet along the way.  One of my favorite things to do when I'm in Southeast Asia is to go to a local outdoor bar called Cheap Charlie's, buy myself a brew and strike up a conversation with the nearest stranger.  I would go equipped with my wit, brain, and personality and with only one intention: to have one interesting conversation with somebody, anybody.  Some of the people I met were strange and mean, but some of them were interesting and cool.  I had a conversation with a middle-aged Swedish businessman about how toastmasters changed his career and how to project confidence during presentations.  I had a conversation with a British school teacher about "The Wire" through a torrential downpour.

Of course, we all have different personal styles when it comes to experiencing the world.  For me, at least, as with many things in life, it's only when we let go out of the outcome, can we have a truly genuine experience.  I'm looking forward to talking about my adventures in Southeast Asia next month on this blog.