The Wayfarer's Book

20 Life Lessons from a Year Traveling the World

20 Life Lessons from a Year Traveling the World

This is one of those “do what I say, not what I do” kinda posts.

October 6, 2015, and I was thousands of miles above Canada en route to Singapore. I had just pulled my eye mask down, put my earplugs in, and settled in to try to sleep, despite the adrenaline of embarking on a year traveling the world. Then I heard the muffled voice of the captain over the intercom and a dozen seatbelt unbuckling. Drowsy but curious, I peeked out from my eye mask. The other passengers were peering out the windows, so I turned to look.

And caught the faintest ethereal wisp of the Northern Lights.

At the time I was sure it meant my adventures were blessed by the travel gods. (And, in contrast, I also started weeping uncontrollably, because we’re basically programmed to cry on planes.) Now, after one year of life abroad, I can tell you it sure wasn’t blessed – but in all its crazy, messy tangledness, it’s still been hella amazing.

A Year of Traveling_Time to Go

Monumentous selfie, taken just minutes before my plane pulled away from the gate at JFK. Also clearly one of the most amazing pictures ever taken of me.

It’s tough to sum up a year traveling the world, twelve months that has included everything from sweating out visa applications en route to Cambodia to sipping fancy cocktails in Kiev. I survived three weeks solo in Mexico, attempted the life of a digital nomad in Serbia, and found the secret places where Americans can teach legally in Europe. I wandered around sixteen countries, hopped around three continents, traveled with a partner, family, friends, and solo — then gave up nomadic life to delve deeper into Ukraine.

They say travel is the best teacher, and since I have a terrible memory I started taking notes on the bits of wisdom I was picking up. Since it’s also better to learn from others’ mistakes rather than your own, here are twenty travel lessons I learned from one year of life abroad.

A Year Traveling the World_All Packed

There was plenty of foolishness too, as you’ll soon see.

1. Throw out ‘coulda, shoulda, woulda.”

I was traveling in Istanbul and Greece with my then-boyfriend, and as experienced travelers, we had started overanalyzing our trip. We were saying things like “We should have done this” or “It would have been better if we could have done that” – when he pointed out that we were self-sabotaging.

I learned this lesson a year and a half ago, to be honest, but I really learned it this year. Living nomadically, my life went by so fast. There’s no time to spend it in the past. And you can’t change that shit anyway. Don’t let living in the past cast shadows on your present.

A Year of Traveling the World_Athens

But on the flip side – I’m not saying “no regrets!” For me, personally, sensible regret is not a damaging emotion. For me, it’s very healthy to look back and say, “I made a bad choice there.” I know some people look at bad choices not as regrets but as learning opportunities – and I do too. Healthy regret helps me be the person I want to be.

But spoiling an evening because you “should have” made a reservation and are now unable to have dinner at the trendiest restaurant in town? So not worth it.

2. Bring your own corkscrew.

NEVER assume that your accommodation will provide a corkscrew. What I thought was a basic human right is not guaranteed when you’re living abroad. And if you’re corkscrewless and you go looking for one, don’t buy the $3 option from a lady in a Kiev underpass. That dodginess is going to break while you’re trying to screw it into the cork.

A Year Traveling the World_Cheap Corkscrew    A Year Traveling the World_Bad Corkscrew

Invest in a nice, real metal (you think the ‘real’ would be obvious, but there are some very clever fakes), travel corkscrew. Life’s too short to be trying to find corkscrew-free how-to videos on YouTube.

3. Carry a scarf for modesty moments.

Women’s hair is scandalous all over the world. I started tying a lightweight scarf to my bag so that I could throw it over my head or shoulders whenever needed. Even in Ukraine, women still cover their heads when they enter the Orthodox churches. I’m not sure it’s required, but it seems like the respectful thing to do.

Don’t get me started on our knees. Gotta keep that sexiness under wraps.

A Year Traveling the World_Modesty in Bali

Scarves and shawls can also make good souvenirs of patriarchy all around the world.

4. Change yo’ money before you leave.

Twenty-four hours before I left Kiev the first time, my manager casually mentioned I wouldn’t be able to change my Ukrainian money.

“You need to have a residency permit,” she said. “Just get one of us to do it for you.”

Instead, because there was too much going on in my life and also I am a travel genius, I decided to wait until I got to Budapest to change my money. With several hundred dollars in Ukrainian hryvnia, I got on the overnight train and swept out of the city.

Turns out no one else in the world wants Ukrainian hryvnia. The only places that I could find to change my money had such terrible exchange rates that I would pay $70 to change $100! My carefully laid plans of surviving off my Ukrainian savings fell apart, as I carried that selectively valuable currency around Europe all summer. Needless to say, I lived it up like a rich lady once I got back to Kiev.

A Year Traveling the World_Budapest

Thanks, Budapest, for being so credit card friendly!

5. You can win big at the credit card points game.

When you live nomadically you fly a lot. I strategically opened up two credit cards right to take advantage of major sign-up bonuses. I used the Chase Sapphire card for a $500 trip from New York to St. Petersburg, Oslo to New York, as well as shaving several hundred dollars off my round trip ticket to Singapore. I’m about to book my round trip ticket home to New York from Kiev, and I’ll again be able to apply $200 worth of points to the ticket.

My Southwest Rapid Rewards card, which I adored, also saved me hundreds of dollars. I flew round trip New York to Memphis, bought two round trip tickets from New York to Austin, then flew Tampa to Mexico City and back Belize City to New York via Memphis. All on points.

A Year Traveling the World_Tacos in Mexico City

Miles have gotten me to so many tacos, for which I am eternally grateful.

Granted, I have used my credit cards a lot too. You must be smart with plastic. But play the game carefully and you could find you’ve made a smart investment.

6. Think before you open your mouth.

Sometimes I feel talking is just an exercise of how much of my foot I can fit in my mouth. To be honest, it happens so often I don’t remember the exact situation that caused me to write this note down.

But I’m pretty sure it was when I was living in Serbia. I was having dinner with my Airbnb host and her boyfriend when they asked about the election. I bemoaned our terrible position, throwing both candidates under the bus.

“Well, we don’t like Clinton,” her boyfriend said.

Intrigued by his immediate response, I asked, “Why not?”

And in the half-second it took for the two of them to exchange looks, I wanted to sweep the words under the carpet. I knew why.

“Because Clinton bombed us,” he said.

“Different Clinton,” I mumbled, but yeah I could see how that would put a damper on the family name.

So think first. While you’re traveling the world, don’t forget the cultural and historical mindset of the people around you. Go to those difficult conversations – but maybe craft your sentences before you let them just fall out your mouth.

7. The sharing economy can be good for travelers. It can also be awkward.

This year was my first foray into Couchsurfing, BlaBla Car, and renting just a room in someone’s house through Airbnb. For the most part, it worked out really well for me. I saved a bundle on accommodation in Budapest and Paris (where two nights in a hostel was going to cost me more than six nights in Belgrade). I’ve only used BlaBla Car once so far, to get from the border of Ukraine to Budapest, but my driver was a friendly older man who bought me a chocolate roll.

A Year Traveling the World_Austin Airbnb

How rad is this?! We stayed in a renovated schoolbus in Austin because AUSTIN. New to Airbnb? Use my Airbnb sign-up code and we both get credit towards our next reservation.

However, the sharing economy can have its downsides. I looked only at female hosts in Paris because one of my hosts in Budapest asked me on a date. And I’m an extrovert, but even I was a little bit weary after spending so much time in other people’s space, whether it was their car or their house. Still, there’re a lot of benefits for travelers in the sharing economies, and I’ll definitely keep using them.

8. Communicate with your bank.

You should always set travel alerts on your debit and credit cards before you take a trip. It’s annoying, because they often only let you schedule a month or so in advance and when you’re spending a year traveling the world these travel notifications can become a gotch-ya game. You should also pay attention to your card expiration dates. Otherwise, you might find your joy at finally getting paid dissipating into misery when the ATM eats your debit card.

I was in Novi Sad, scraping by on the last of my US dollars after my hryvnia were refused, and I was thrilled to finally have money in the bank. I was already mentally spending my dinars when I slipped my card into the ATM – and it promptly ingested my card.

Long, sad story short, the tech in my card was outdated. When I finally got in touch with Chase directly, I was told they had shipped me a new card – to my New Jersey address.

“When will you be back?” the nice customer service lady asked me.

“Christmas,” I said grimly.


My parents were able to bring me my new card when we met up for our family vacation a month later, but until then the only way I could access my money was through expensive wire transfers. Puts a damper on pay day.

9. You can call domestic 1-800 numbers through Skype.

Maybe this seems like a no brainer to everyone else, but I struggled for three days trying to contact my bank with their international toll free number. As I didn’t have a SIM card, I tried to hunt down a phone. I even tried using the payphone in the middle of the town square to no avail.

And then I realized I could call them domestically through Skype. And while my bank couldn’t call me back still, it was a game changer.

10. Everyone’s definition of affordable is different.

Traveling with people can be a lot of fun, but you do have to negotiate a lot. You have to negotiate time, dinner choices, and budget. Not discussing budgets enough causes a lot of tension between travel buddies, so make sure you do it early and clearly.

A Year Traveling the World_Angkor Wat

And it’s not enough to just say “let’s keep it affordable.” Different incomes, different priorities, makes ‘affordable’ different for everyone. Give ‘affordable’ a number and make it easier for you and your travel partner.

11. The best moments aren’t at tourist sites.

Watching the sunrise over the Thai countryside from our bunks on the overnight train. Having a whole fancy restaurant in Bali to ourselves because everyone was flocking to sunset spots. Making friends with the master brewers of Serbia’s craft beer scene and drinking for free at their bars. Rocking out at a hip hop/jazz jam session on a boat on the Danube. Sipping mojitos and listening to the bartender at a tiny Cuban hotel share his concerns about their modernizing country. Breakfasting on croissants and fresh orange juice in our friends’ Parisian courtyard. Motorbiking anywhere and everywhere.

A Year Traveling the World_Star Wars in Bangkok

One of my only requirements in Bangkok was seeing Star Wars at one of the VIP theatres. And yes, it was amazing, and no, movies are never going to be the same for me.

My favorite memories don’t include the Eiffel Tower, the Marina Bay Sands hotel rooftop, or 12th century churches. They’re on speedboats in Malaysia, paladares in Cuba, and VIP movie theatres in Bangkok. Breakaway from the guidebooks, and you’ll discover something wonderful.

12. But you have to work for them, too.

You have to earn these unique moments. You have to do your research, you have to say yes to opportunities, you have to be open to other people.

A Year Traveling the World_Thai Sunrise

Golden Thai sunrise en route to Laos.

13. You don’t choose which monkey to feed. The monkey chooses you.

If you go to the Sacred Monkey Forest in Bali and buy bananas to feed to those little twerps, believe me when I say you have about 8.2 seconds to get rid of the goods. Do not, under any circumstances, try to deny a big monkey a banana that you wanted to give to the baby monkey.

I don’t even have any pictures of this because it all happened so fast.

A Year Traveling the World_Sacred Monkey Forest

Do not let that innocent face fool you. Wild creatures, they are.

14. Get a local grocery store.

One of the most stressful things about expat life is grocery shopping. The first time I tried to cook a proper dinner in Kiev I went to the grocery store three times. Trying to navigate the different labels, packaging, and ingredients can be overwhelming. Having a ‘local’ means that you get used to knowing where your go-to ingredients are and that the staff starts to get to know you as that perpetually confused American girl who is helpless to an infantile level – and they start treating you much more kindly.

Seriously, having a local grocery store has been one of the biggest stress-alleviators in my life abroad.

15. Learn how to communicate with non-native speakers.

You would think pantomiming would be universal, until you’re trying to buy contact solution in Ukraine.

However, it’s been fairly easy for me to get what I need, from Singapore to Serbia. I’m incredibly lucky to speak English as my first language, totally pampered by the fact that most others also speak at least a few words.

A Year Traveling the World_Mexico

I was thrilled that after three weeks in Mexico I could hold rudimentary conversations — as long as the person spoke slowly and with expressive hand gestures.

I’ve noticed some of my other English-speaking friends struggle, though, with communicating, and I end up acting as an English-to-English translator. When speaking with a non-native speaker (of any language), speak slowly, eliminate unnecessary words, and avoid phrasal verbs (er, or whatever the equivalent is in your language). “I called ahead to book a table” is way more confusing than “We have a reservation.”

16. Found an English speaker? Ask them all your questions.

My friend and I were castle hunting in western Ukraine when we rolled in late to our hotel one evening. We had questions about our adventures the next day but were too tired to bother – even though the receptionist we had already pestered that day smiled at us friendly.

“We’ll ask in the morning?” my friend suggested, to which I readily agreed.

A Year Traveling the World_Kamyanets-Podilsky

Except the next morning, the woman at reception spoke half the amount of English the woman the night before had. Our questions were small, and we managed on our own anyway, but lesson learned.

17. Communicate with your bus driver.

Ah, the lesson I never seem to learn. A year traveling the world, and still I’ve made this mistake everywhere from Mexico to Romania. These shuttle buses that zip from city to city don’t have the clearest itineraries. Getting on the “Cancun-Tulum” bus doesn’t mean you’re going to get door-to-door delivery. I literally sat quietly as every other passenger told the driver where to stop, until it was just me, and the driver turned to look at me inquisitively.

What was I still doing there?

A Year Traveling the World_Tulum

I stammered and stuttered and used what little Spanish I knew and my iPhone to show him my hostel. We had passed it ages ago, and I had to turn around and walk twenty minutes back the way we had come. Lesson not learned, I pulled a similar stunt in Romania, having to book it three miles from where I finally got off the bus to the salt mines before they closed.

I like trying to blend in when I travel, but in this case it’s just better to just out yourself and hope the bus driver remembers you when it’s time for your stop.

A Year Traveling the World_Salina Turda

Salina Turda, where the Romanian government asked, why leave a salt mine empty when you can make it a theme park?

18. Travel doesn’t solve your problems.

Travel doesn’t heal your broken heart. It doesn’t fix your depression. It doesn’t give you purpose.

You do that.

Travel may be part of the solution. It opens your mind, exposes you to new perspectives, takes you away from damaging situations. Leaving New York and its prohibitively expensive lifestyle meant that I could finally have my own apartment, order cocktails without feeling guilty, and integrate travel more easily (and affordably) into my life. Leaving New York was an important part of alleviating stress and sadness in my life. But the act of movement alone doesn’t fix your life. You do that, with thoughtfulness, wisdom, and determination.

A Year Traveling the World_Paris

Qui n’avance pas, recule. (I don’t know French so I Googled until I found something I liked.)

19. Collect wifi passwords.

When I’m staying long-term in a city, I intentionally visit different coffee shops (even if I develop an immediate caffeine-related bond to one) in the first week or so, and I make sure I get the wifi connection for every single restaurant, café, and bar I visit.

This solves the lack of data. Need to connect to the internet? I just loiter outside of one of my makeshift wifi hotspots for a few minutes. Mischief managed.

20. Go.

I’ve wanted to travel like this for years. But even in all my dreaming, I never imagined that I’d spend a whole year traveling through sixteen countries. That I’d solo adventure through Mexico for three weeks. That I’d put down roots in Europe’s eastern edge. It’s not always been graceful or easy or fun. But it’s been wild. Wild, and full. And I’m perfectly content with that.

And now, on to more adventures.

A Year Traveling the World_Living in Ukraine

Get ready.

What are some of the best lessons you’ve learned in your travels?

20 Life Lessons from a Year Traveling the World

Better to learn from others’ mistakes than your own! Pin this for future reference.


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14 thoughts on “20 Life Lessons from a Year Traveling the World

    1. Amy Post author

      I think I’ve finally found my perfect corkscrew! A simple waiter’s corkscrew seems to be the best. :) Glad you enjoyed the lessons, hope they help sometime.

  1. Catherine

    Love it! Especially the part about travel not fixing your problems… Some amazing tips here, thank you for sharing your lessons! I’m terrible at travelling but I’d say just walking around the area when you arrive is really helpful, and marking important places on your map with stickers. You probably won’t remember the names of roads!

    1. Amy Post author

      I also love just walking around! I think you can get a real feel for the place and discover little gems that might not be in the guidebook. Even in Kyiv, when I have the time to walk instead of use public transportation I go for it.

  2. LJ Sedgwick

    I’d love to travel more but I guess I worry about the language barrier. I’m an introvert so it’s difficult enough to speak to people without having to worry about which language to use! You’ve made it sound amazing though.

    1. Amy Post author

      I totally understand what you mean! I worry about annoying people as a ‘dumb American tourist.’ But I’ve found people are in general really helpful, and once you get comfortable with looking a little silly, it’s not so hard.
      But always give yourself plenty of time to figure out directions. :)

  3. Camilla

    Great life lessons. I am so envious of such an epic experience.
    #10 is so true… especially for food choices

    I would like to do the same but I’m quite afraid to be so depressed when coming back
    How did it feel and do you have tips to go back to the “normal life”?

    Camilla |

    1. Amy Post author

      Ah, Camilla, I’m avoiding that dreaded post-trip by just not going back. :) I’ve settled in Kyiv for a year and after that I imagine I’ll spend a few more months in Europe before traveling somewhere new.

      But I did used to get post-trip depression. I came back from trips and would get teary in the elevator at work because I missed being on the road so much. Maybe it’s a case of the grass is always greener on the other side, because I know I’ve had plenty of grumpy/dismal days while traveling too. But I think the key to escaping post-trip depression is to cultivate a life you’re happy to return to. Whether it’s focusing on your friendships and relationships, developing your hobbies, or pouring yourself into a job you love — as long as you have some aspect back in your ‘normal life’ to ground you, transitioning back isn’t so bad.

      And, also, planning your next epic adventure always helps too. :)

  4. Wendy Richards

    This is amazing. I would love to up root and travel, having a dog makes that difficult but I hope to find a way to travel with him in the future. Great tips to keep in mind as I plan.

    1. Amy Post author

      I have the opposite problem as you — I would love to have a dog but my current lifestyle makes it rather impossible. :) Definitely something that attracts me to the ideal of settling down! :)

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