30 Lessons from Life on the Road

“I can tell you’ve been traveling for a long time,” not one, but three strangers have said after talking to me for a few minutes over the last month.

“Really?” I’ve asked each of them. “How’s that?”

“You just seem really… I dunno. Relaxed. Easy-going. Zen.”

At that last part I always have to laugh. Six months ago, three months ago, no one in their right mind would have used the z-word in reference to yours truly. But as I sit here and realize, with no small amount of shock, that six months have already passed since I first started my adventure, I can’t help but believe there might be a grain of truth in these strangers’ unusual choice of adjective.

I don’t have it all figured out by any means. I still have isolated days when I wake up and wonder where this is all going, how I’m going to replenish the bank account I drained traveling Asia, and what it would be like waking up in a double-bed in my own room instead of a top bunk in a room full of strangers. But even if I don’t have this whole thing down to a science just yet (and, hey, why would I want to?), It’s getting easier to go with the flow the more I learn. And I’ve definitely learned a thing or two. Or 30.

On Travel

1. Don’t skip the places you’re unsure about. Sometimes, the destinations you can’t get excited about pre-departure turn out to be your new favorites.

2. The journey can be just as important as the destination. So don’t forget to look out the windows, take your time, and mix it up.

Village life on the Mekong as seen from the open-sided slow boat into Laos.

On Backpacking

3. Any backpacker with a ukulele or guitar will inevitably play Jason Mraz’s “I’m Yours” before the night is through. They will not know all the words — and even after countless late-night singalongs around fireplaces, beers, or open-mic-night stages, neither will you.

4. A hostel is only as clean as you think it is. Sometimes, the people cleaning and washing the laundry have no idea what they’re doing.

5. An organized tour bus is a great way to meet people. It’s also a great thing to move on from.

6. Packing cubes are a game-changer.

7. After a while, you start conversing with your backpack as though it were a living, breathing person — specifically a disobedient child. “Why won’t you close? You closed yesterday and I haven’t added anything new!” “Do you really need to keep hitting me on the leg, strap? Really?” “I swear you’re heavier than you were last week. How is that even possible?”

Hayley illustrating the typical size ratio of backpack-to-backpacker. I’m pretty sure if she were sitting beside me right now, she’d want me to point out that her tan improved a bit after this picture was taken.

8. Even your lightweight MacBook Pro feels as if it weighs a metric ton after you’ve schlepped it across eight countries.

9. Finding a truly great hostel is like being a crack addict who’s been saved by the Church: you’ll tell anyone who will listen about how this place will change his or her life. Hyperbolic hand gestures and solemn testimonials will follow.

On People

10. It’s much easier to talk to strangers than you think.

11. The first question people ask a new acquaintance back home is always “What do you do for work?” On the road, you ask “Where are you from?” “Where have you been?” “Where are you headed?” and “How long are you traveling for?” The question “What did you do back home before you came traveling?” is an afterthought, if it’s posed at all.

12. Even when you’re traveling solo, you’re never really alone. You meet new people, you run into them again, you part ways, you make new friends. The social possibilities of the backpacker are fluid and endless.

Instant buddies in the back of a jumbo tuk-tuk. I can’t take credit for this picture — some new friends took it and posted it to Facebook. So, thanks, girls!

13. Still, moving around so much makes you miss your old friends like never before.

14. Be nice to the girl at the pastry shop. She’s probably sick of serving yahoos like you all day.

15. It’s refreshing being surrounded by other backpackers, if only because none of them have any idea what they’re doing, either. And they’re just as happy about it as you are.

16. Compared to other nationalities, there are not a lot of Americans out there traveling the world. And I don’t have a great answer when people ask me why.

17. There’s something very cool about entering a room full of people from Germany, France, Sweden, Taiwan, and hearing them all converse with each other in comfortable and fluent English. Other backpackers often ask me why more Americans don’t learn a second language. Again, I don’t have a good answer for them.

18. Native English speakers pretty much won the travel lottery. People from non-English-speaking countries have to learn English just to have a few mutually understood words traveling not just Anglophone destinations but in places like Vietnam or Laos. Seriously — why don’t more Americans take advantage of this?

On Fashion

19. Flip-flops are surprisingly versatile — if you’re not at all self-conscious.

20. When choosing outfits, I used to strive for matching, venue-appropriate, occasionally even slightly on-trend. These days, I strive for “borderline clean.” It usually doesn’t bother me. But some days, I think I’d trade my backpack in a heartbeat for a flowing dress and a pair of heels.

When did “sneans” become an acceptable wardrobe choice? About two months into my trip.

On Food

21. The food that people can and will make in hostel kitchens is truly astounding. I’ve seen full-lattice-top cherry pies, foccacia and challah, bagels from scratch, fresh stir-fries, Asian noodles and soups and salads nailed down precisely to the last spice and sauce. I’ve tasted homemade cookies, quiches with rolled-out crusts, hand-made springrolls, fried rice, and yes, even Yorkshire pudding. If you want to see young people who don’t just cook for themselves but take pleasure in doing it, go traveling.

22. You can get some amazing, exotic, exciting food when visiting other countries. But damn it if the sight of a humble Subway sandwich shop can’t make my face light up after weeks on end of fried noodles and curries.

23. A 50-cent meal purchased from a street cart, packed up in styrofoam or newspaper or cellophane, and eaten with chopsticks in the back of a tuk-tuk is often a more delicious and transcendent experience than eating a fancy meal in a restaurant.

Many thanks to my good friend Eli for demonstrating the proper way to eat and run.

On Life

24. There are few bad days that can’t be improved with a cheap bottle of red wine and a big ol’ block of chocolate. If that doesn’t work, try buying plane tickets.

25. Itineraries are only rough sketches. Plans are just ideas. Commitments are overrated. The best moments are often born of spontaneity and irresponsibility.

26. I’ve barely watched any TV in six months (the occasional NZ news segment notwithstanding). I wonder sometimes what Sally Draper’s up to or if Ted Mosbey’s met his wife yet, but other than that, it’s kind of nice being out of touch, forgetting the stuff I used to rush home to be on time for…

27. …but I’m still composing a mental Instant Netflix queue for my eventual return to the States.

28. I still can’t decide if settling in one place long enough to unpack, buy full-sized toiletries, and develop a routine is the light at the end of the tunnel or my worst nightmare.

29. There are adrenaline-fueled activities you know you want no part of, and there are new experiences you dream about but don’t think you’re brave enough to try. Don’t get them confused.

30. I’ve been extremely fortunate so far in my travels: I’ve made some incredible new friends, traveled with relative ease to places I’d never dreamed possible, and had work just fall into my lap. But the more I think about it, the less I believe it’s all been thanks to dumb luck. I’m starting to think serendipity is the good stuff that happens when you finally just get out of your own way.

Impulsively purchased plane ticket + perfect timing = happiness.

What are your favorite lessons learned from travel?