17 Lessons from 17 Years of Travel & Chasing Dreams
I am about to embark on yet another leg of long-term travel. I felt it only fitting to commemorate 17 years of studying abroad, living abroad, working abroad and working remotely while traveling the world by sharing with you my story and the 17 lessons I have learned along the way.
Here goes.
Starting at age 10, I spent every summer in the north woods of Wisconsin, at Camp Birch Trail. For me, this was the only place in the world where I could be completely me. I was surrounded by laughter, nature, adventures, singalong songs, traditions and rituals. It was f*cking heaven.
At 15 years old, my time as a camper came to an end. My best camp friend Lois and I somehow decided to convince our parents to let us join a teen tour to travel Israel and Poland. For six weeks, we traveled with a mixed blend of Americans and Israelis all over. I was, again, surrounded by laughter, nature, adventures, singalong songs, traditions and rituals. Heaven.
Looking back, it’s pretty clear why camp so easily turned into travel for me. I, to this day, have no idea where I even got the idea to go to Israel for the summer. My parents weren’t big international travelers and I was pretty young to want to hop over to the other side of the world with a group of (mostly) strangers.
That summer in Israel and Poland at 15 turned into a summer in Hungary at 16, turned into a summer in Sevilla at 17, turned into moving to Argentina for a year at 19.
To say I was hooked is an understatement. Travel became who I was. In college, I studied International Studies, Political Science, Latin American Studies, and Spanish. Living abroad, studying the world, experiencing cultures that were different from mine, it was everything. All day long, I dreamt of the possibilities.
That is, when I wasn’t freaking out about what I was going to do with my life. After spending my entire junior year in Buenos Aires, my senior year was spent back in Madison. The big question, “what are you going to do when you graduate” loomed over me.
I had no real fears about getting a job, mostly because I’d worked on and off since I was 15 (13 if you count babysitting) and knew how to find work. My real fears festered about how the hell I was going to be able to live abroad, make enough money to support myself, AND find something prestigious enough to make my father happy.
Turns out, there was one thing that might just check all the boxes: a Fulbright scholarship to teach English in Spain. It was a long-shot. The spots were extremely limited, particularly for the post that I wanted, and I was up against the “best of the best”. But, I knew I had to go for it. I would be able to make money, live abroad, AND land the approval of the outside world. It was just a two-part process: submit the application by October, an interview in February and the final decision would be released right before I graduated…in April.
All year, I imagined my new chapter of drinking sangria and teaching English to little Spanish niños. I couldn’t believe how perfect this would be for me. I was MADE for it. I mean…remember what I studied? When February rolled around, I landed the interview. Hopes up, all I could do was wait for April.
In the mean time, I applied for a Master’s in International Studies, landed a job at Boeing (long story for another time), and was accepted into the 2010 Teach for America Houston Corps. Even my back-up plans had back-up plans.
April came. The decision landed so unassumingly in my inbox. I didn’t get it.
I was devastated. I knew at the time I had to choose something from one of my “back-up” options. I went with Teach for America. For the next two years, I lived in Houston and taught fifth graders in the 5th ward of Houston.
It might not have been abroad, but it felt like living in another country. It was wild and an adventure all it’s own. I helped kids every day get clear on their dreams so they could find the motivation to learn what they needed to learn. I was learning about how powerful dreams are not just to find the inspiration to do hard things, but to find joy in the process.
Even so, my dream of living abroad never died. Just a few months into my first year teaching, I met a man. He had just gotten back from teaching for a year in Italy. Whether it was his man-bun, the 8 years of “wisdom" he had on me or the dream he was representing, I was smitten. He’d shown me another way. I could teach at an international school, make real money, and be an “adult”.
That relationship fizzled and another one quickly began. From the day we met, all I talked about was how badly I wanted to live abroad and to travel the world. I reeled him into my plan to to teach abroad at an international school. We were both ready for a move and began applying for jobs, abroad and across the US.
Shockingly, in the same day, we both got hired to teach at a school in Quito, Ecuador AND for education-related roles in Chicago. There was a decision to make. We sat at a restaurant on Division St., just a couple of blocks from our house. We ran the numbers. We discussed our options.
Quito couldn’t happen for him. The amount of money we’d be making in dollars just didn’t make sense for the pile of student loan debt he was still sitting on. I cried my eyes out at that table and chose to do what I thought was the right thing. We moved to Chicago and promised each other we would take one international trip every year.
Six months into Chicago and I was already itching again. We took that international trip and went to Italy. It was beautiful and I still wear the leather jacket I bought in Florence. Two weeks of wine and pasta and meandering Rome left me wanting so much more. You know how sometimes the appetizer makes you hungrier? Yeah, it was like that. It didn’t quench the thirst.
Six months after that, we went on vacation with my cousins to Costa Rica. At this point, I hadn’t “lived” abroad in nearly five years. Living abroad felt less like a dream and more like a daily tugging at my heart. I was in a serious relationship, living with someone in Chicago. I was losing steam for being in education, but I had a prestigious job, a city full of friends, and everything should have been great. But it wasn’t. I wasn’t happy. I felt stuck and lost. As much as I wanted to travel, I wasn’t ready to blow up the life I had created for myself.
In Costa Rica, I started reading the 4 Hour Work Week by Tim Ferris. Sitting on the edge of an infinity pool overlooking the jungle, reading about these people who were working remotely and traveling the world, I felt my heart start beating. This was it. This is what I’d been looking for. I’d found my people. I’d found a new sense of possibility. I didn’t know how, but this was my path. The light was back on, baby!
I have to take a moment and thank my partner. As committed as he was to our relationship, he was more committed to me. To letting me be me. To letting my dreams be my dreams. To cheerleading me every step of the way. An angel in human form supporting me, knowing it would likely leave him hurt in the end. Loving me enough to let me chase my dreams, even if they didn’t include him.
The next year was full of experiments on how to work remotely and travel. I put a map of Thailand up on my desk at work and got down to business. I asked my boss if I could work remotely. I started a travel blog. I even went to a conference for travel bloggers. I applied to business school. I threw spaghetti at the g*damn wall and believed so deeply that eventually, something had to stick.
I saved up more money than I ever had ($9,000) and became an expert “travel hacker” stacking up hundreds of thousands of points. Eventually, each of these plans fizzled out. I quit my job and decided that even if I didn’t know what I wanted to do, I knew I wanted to travel. But I didn’t lose hope. Not this time. I booked a one-way ticket to Bangkok and knew I’d figure out a way to make this my career.
Two months into my travels, I called my boyfriend and told him this was the lifestyle I wanted to lead. I wasn’t coming home. Not for good, anyways, for a very long time. I might not have figured out the career piece, but I had found the life piece. A few months later, I flew to Mexico for my best friends wedding. Ending my chapter in Thailand, it kicked off the reality that my time in my Thai bubble was over and I needed to figure out this career thing.
I spent the summer working for my Dad while I applied for remote jobs and made my plans to get abroad again. I finally accepted that traveling, living abroad, was the only option. I didn’t care if I had a prestigious job. I didn’t care if other people approved. Adventuring was where I belonged.
Just a few weeks after I landed back in Chicago for the summer, I saw that a friend of mine had started a company that took people who worked remotely on trips around the world for a year. Just back from Thailand, I reached out to congratulate him and send him some tips as they were heading to the beautiful country that I had fallen in love with. Our conversation very quickly turned to him sharing that he was hiring.
I hadn’t even thought to ask for a job. I hadn’t even considered that maybe this could be my dream job. But as soon as I read that email, I knew. I knew more clearly than anything I’ve ever known in my life that this was my dream job. This was the career I had been waiting for. I was going to get to help people chase their dreams, the same dream I had, while living that same dream. Three weeks later I was on a plane to Istanbul to start working for Remote Year.
The next three years were once again, a wild and crazy ride. But for the first time in my life, I didn’t have one foot out the door. I was two feet in and I was living the dream. My job consisted of talking to people about how to make their dreams a reality, while I was in my bathing suit working from the beach in Thailand. My job consisted of working alongside a bunch of other travel-obsessed humans who were just as carzy as me. The freedom. The travel. The sense of purpose. The community.
Once again, I was surrounded by laughter, nature, adventures, singalong songs, traditions and rituals. It was f*cking heaven.
I could write an entire book about my experience working for Remote Year. But I will save that story for another time. Instead what I will say is that it broke me in the best way possible. Never again would I trap myself. Never again would I let myself believe the illusion of being stuck. Never again would I give up so easily on my dreams, after having tasted the bliss of them coming true. Never again would I live by anyone else’s rules, dreams or desires but my own.
Eventually, the dream ran its course at Remote Year. A new dream was beginning to form. I wanted to build something of my own. I wanted a the “real deal” relationship. I wanted, for the first time in a long time, to ground myself in a place again. Almost four years into my Remote Year experience and five years traveling the world, I received the universal nudge and was laid off. It was time.
Within a month, I started my business. Within six months, I moved back to Chicago to focus on my new dream. A month after I moved back to Chicago I met my life partner. We’ve been together for two years, lived together for one, and survived a global pandemic while truly enjoying each other’s company. While for a minute there, I thought I’d be back in Chicago “forever”, once again that itch returned. Thankfully, he’s got it too. Our lease is up in six weeks and we’re packing a carry-on backpack and heading out to explore the world, together.
17 Lessons from 17 Years of Travel & Chasing Dreams
Dreaming is the ultimate adult playground.
Humans are humans are humans.
Make wish lists. Dream wish lists. Travel wish lists. Life wish lists.
Most places feel safer than Chicago.
Don’t have back-up plans for your dreams—commit to the dream.
Carry-on luggage will teach you to love minimalism.
Open yourself up to the 1000 ways that your dream could become a possibility.
There is no rush. We’re not saving babies here (unless you are).
Fuck what other people want for you.
If society says you “should” do it, you probably shouldn’t.
Thank the people who support you and cheerlead you—they are the angels in human form.
Find ways to enjoy the pursuit of the dream just as much as living it.
Start with the low-hanging fruit—identify the parts that you can make happen now!
There’s no better way to live in the “present”.
You can get a SIM card anywhere in the world.
Take pictures, but don’t get distracted by your phone.
Disconnect (get off grid) to reconnect.
Journal Prompts
Spend a few moments answering these questions for yourself today.
Dream Quiz: Am I a) living my dream b) building my dreams c) getting clear on my dreams d) living someone else’s dream e) waiting for permission?
If I died tomorrow, could I say I lived the way I wanted to? If not, why not?
Make a “wish list” of dreams & post it somewhere (or tag me in it on instagram! @emilyelizamoyer)