Hey, time. It’s you again. As of this month, we’ve officially been traveling for two whole years. Two. Whole. Years. That’s longer than I was on probation! And much less depressing. We’ve moved from Texas to Costa Rica to Maui, and have more big travel plans in store for 2015.

I always tell people that the first thousand bucks is the hardest to save, and the same goes for the first year of travel. But truth be told, it’s a lot harder to save a thousand bucks than travel. At least for me. And the good news? Two years of travel was a total freakin’ breeze.

Last year I wrote a post about what we learned from our first year of traveling, so this year, as your quick wit and stellar deduction skills might have already decoded, we’re going to share what’s changed, what’s the same, and what else we can tell you about how to travel (and keep traveling) as a mostly broke, mostly planless human being.


Lessons After 2 Years of Traveling


Baby Steps are Overrated

Baby steps are cute and all, and they certainly have their time and place, but sometimes you’ve just got to rip your bra off and jump in. Or for a less confusing example, pour yourself a hefty glass of bourbon and buy the damn plane ticket.

If you’ve wanted to move for half of your life and haven’t done it yet (excusing any serious setbacks), you deserve a swift punch from the nearest a-hole. Retirement is a long way away for the majority of us, and even if it’s not, what the eff are you waiting for! Getting pounded into the shore break when you’re 25 is much more amusing than when you’re 75. Ask a 75 year old. Preferably one that’s recently been pounded into the shore break.

As with most things in life, the sooner the better. Go, do, see, be. Rip the bandaid! And the bra! Get out there before you’ve got to start adding Depends to your grocery list.

lessons after 2 years of traveling

Happiness is a Choice

This goes without saying, but shitty things happen to everyone, everywhere, all the time. Even those who live on stunning little tropical islands in the middle of the Pacific Ocean.

Just because you decide to move somewhere wonderful doesn’t mean unfortunate things won’t still happen to you. They will, and they’ll likely be worse until you get used to the fact that you’re no longer surrounded by a built-in support system of close family and friends.

Remember that you are in charge of your own happiness, and learn to be a boss at solving your own problems.

moving to maui

Bury the Hatchet

I’m a grudge-holder. Always kind of have been, always kind of will be. I don’t believe in making excuses for other people’s uncool behavior. And repeated acts of this type of behavior only means you’re an uncool person, plain and simple. But the thing about constantly meeting new people is that you’re bound to dislike some of them. Hell, I still dislike some people I’ve known my whole life. That’s just human nature.

That being said, I’m trying to be better at letting things go, burying the hatchet, getting over it, whatever you want to call it. Because at some point, especially when you’re living on a relatively small island, you’re going to run into them. Put a timestamp on your grudges, y’all. If I can do it (whilst gritting my teeth and throwing mad shade in the cereal aisle), you can, too.

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Stop Guessing, Start Knowing

Life is based on guessing. I could make the argument that most of my important life decisions have been made by guessing that I’d still be alright with making those same decisions at some point in the future.

But when it comes to me personally, guessing won’t do… I know what I’m good at, what I need help with, what I’m generally capable of, and what kind of person I am. And knowing these things about myself truly does make me a better traveler. For example, I know for a fact that I can meet people and make friends anywhere I go. Even cardboard boxes, if left in the same room with me for long enough, should definitely expect an invite to my next birthday party. I also know for a fact that those skill leads to amazing opportunities, and those opportunities exist all around the world.

Peter, on the other hand, knows that his wide range of impressive man-skills in the ocean (and out of it) can generally land him some kind of job wherever we go.

Learn what your strengths are, have confidence in what that means for your travels, and run with it. Literally (if one of your strengths includes running) and figuratively.

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Take a Big Ass Pill of Chill

Moving takes patience, and the idea of starting from scratch – new home, friends, jobs, hobbies, activities, etc. – scares a lot of people away. Give yourself time to get into the groove of a new place, and don’t beat yourself up if it’s just not your jam.

Traveling is about learning how to handle your shit, and getting better at doing it in extraordinary places. Relax, breathe, make mental notes, puff puff pass, and be thankful that your life is still less dramatic than Days of Our Lives.

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