The Art of Getting Lost

Buckle ups, folks. Grab your notebook and your favorite #2 pencil. It’s time for The World’s Dumbest Traveler to impart some knowledge. You might be thinking, “Why in the world would I take a ‘lesson’ from a guy who calls himself “The World’s Dumbest Traveler?!” And it’s certainly a fair point, but bear with me. We can get lost together…

There is no better feeling in this world than getting lost and discovering something amazing. You could say it’s a lost art, really (my mother calls it a dangerous habit). But there’s a certain unpredictability to the adventure you find when you have absolutely no idea where you’re going.

It could be a hidden park, a beautiful outdoor bar or an unexpected view, but it’s these things you go back home and brag to friends and family about, more than any tourist attraction you’ll ever visit. However, in order to get lost and discover these hidden gems, regardless of the location, there are three distinct things you need. Three earth-shattering secrets I once thought I was going to take to my grave, but now have the sudden urge to share with you good people.

You need:

Willingness to get lost
Irrational confidence in your ability to get where you’re going
Ability to lie directly to the face of friends, family and social media

Let’s go into a bit more detail on each one of these…

Willingness to get lost – It all starts here. Sure, you might have list of places you want to see or an idea of what you want to do, but if you can’t let go of these plans or at least be okay with going off-script you’ll probably be miserable and cranky and die alone end up having a fine time. You’ll see the same sites, visit the same places, take the same pictures as the millions of other tourists who have come before you. If you’re fine with “fine,” then I’m fine with “fine,” but if you’re looking for more you need to be open to getting lost.

Irrational confidence – Maybe this is just a me thing, but you have to truly believe you know where you’re going. Deep down, in places you don’t talk about at parties, you have to believe you’re going the right way. You look at a map or you briefly plug an address into your GPS and you say to yourself with a swagger in your step, “Yup, I’ve got this.” The problem is that 9 out of 10 times you do not, in fact, “have this.” But it’s at that exact moment of the “oh shit, I’m lost” that the fun really starts. Which leads us to step three…

Truth bending – While every step of this journey is crucial, this right here is what separates the men from the boys, the women from the ladies, the sophisticated from the sissymuffins, so I want you to listen closely. You must never admit that you are lost, were lost or ever will be lost. When a friend asks you how you were so lucky to find such a beautiful private beach you say things like, “Oh, I just stumbled upon it,” “It was a recommendation from a local bartender,” “I just followed the sound of the live music…” You deny, deny, deny. You were NOT lost. You were simply enjoying an unpredictable adventure.

This probably isn’t the travel lesson you expected, but it’s the travel lesson you need.