I was raised to understand adulthood to mean a traditional path of college (I was the first in my family to graduate with a degree), job, marriage, house and then, children. I spent a semester abroad while attending a university, then went to work in very corporate environments in marketing and public relations in Boston, where I became a pro at hoarding vacation days to fit in trips to destinations such as Morocco and India ― places that require far more than four or five vacation days.
I spent my 20s and 30s straddling a life of traditional work while still daydreaming of adventure. I was miserable going to an office every day, but I ignored my desire to pursue non-traditional options because it seemed terrifying and irresponsible.
Fast forward to 2014, single with no children, I celebrated my 40th birthday blissfully alone hiking at Joshua Tree National Park in California. That’s the week I formally started the journey of transitioning from a stationary life to a nomadic one. I saved a nest egg of $25,000 in just over two years by living on a very tight budget and put together a plan on how to freelance while traveling.
Given years in the corporate world, I’m extremely organized. When I hit my savings goal in early 2017 and gave my notice at work, I was confident I had considered just about every situation of life on the road. I had a monthly travel budget, a spreadsheet of desired locations across Europe and India, and bookmarked countless resources and expert tips to help along the way.
If you Google “how to quit your job to travel,” more than 110 million sites appear to be a treasure trove of information. However, now that I’ve been on the road for the last year-and-a-half, I realize that the majority of bloggers who travel long-term or leave the U.S. to be digital nomads talk a lot about the technical aspects of the lifestyle, like how to find fast Wi-Fi, while leaving out much of the nuanced day-to-day struggles, like how to make friends when you are 43 and living out of a suitcase.
My plan was to travel slowly across Eastern and Western Europe and later India, choosing a new home-base city every month or so where I hoped I would feel settled while also soaking up authentic experiences in locales that rarely make top-10 lists. I thought I could meet up with other remote workers in gorgeous coffee shops or co-working spaces and find a community.
I eased into my travels, joining a group tour to lesser known parts of Eastern Europe. After the trip I felt good about truly setting out on my own and was off to Riga in Latvia for two weeks. That’s where I ran into my first snafu. The hostel I booked seemed more like a men’s prison — I was the only woman in a place that stank of stale cigarettes in the dark stairways littered with empty vodka bottles. But how could so many five-star Trip Advisor reviews be wrong? This was my first lesson in detouring off-the-beaten path — never believe the glowing reviews.
The next lesson in traversing the globe was what another long-term traveler I met calls “admin-time” ― the stuff that ranges from booking flights to deciphering train schedules in a foreign language. After locking myself in my Riga hostel for the first two days, I spent the next two tearing up my spreadsheet, changing my plans and booking flights, trains and accommodations through Central Europe down to the Balkans, a region that hadn’t even been on my radar until the folks I met on my tour raved about Bosnia, Serbia, Kosovo and Montenegro.
I clicked with this area and felt a kinship with those I met. However, when everything is always new, it takes a lot of time to accomplish unremarkable things such as finding a grocery store, doing laundry (there are no laundromats on every corner) or visiting a long list of coffee shops to test out which ones have delicious coffee and speedy Wi-Fi. This all amounts to several hours of admin time each day. And spoiler alert, aside from a few hidden gems, by far the most reliable and speedy Wi-Fi is available at chains like McDonald’s, where I spent countless hours camped out in cities from Bucharest to Belgrade.
By far the most reliable and speedy Wi-Fi is available at chains like McDonald's, where I spent countless hours camped out in cities from Bucharest to Belgrade.
After several rewarding but somewhat lonely months in Eastern Europe I had a month planned in Paris — it’s always been a dream to call the city ‘home,’ even for short amount of time. It had been harder to make friends than I expected, and here, for some reason, I thought it might be easier.
In an effort to be more social I decided to give Tinder a try. Fine, if I’m being honest, I was looking for something between a date, or at least someone to chat with while I drank a glass of red wine, and a cute guy to take me back to his tiny Haussmann apartment building. My dating life stalled when I lived in Boston. Add to that the difficulty of meeting anyone when you move around every few weeks like I’ve been since early 2017 and, well, Barack Obama was still in the White House the last time anyone saw me naked. Paris was the place to change that, right? Wrong.
Turns out French men aren’t all that different from Americans when it comes to swiping. Most responded with just a word or two. If they couldn’t be bothered to put in any effort, I certainly wasn’t. I once again deleted Tinder.
Back home I would have spent a night out with the ladies commiserating our singledom status, but thousands of miles away I used my dating failures as an excuse to get out of my comfort zone. Instead of sitting home watching Netflix I searched out free events and gatherings for expat crowds where I could speak English for a few hours without feeling guilty and meet up with other adventure-minded people.
It wasn’t until my time in India that I fully understood the isolation of being on assignment thousands of miles away from friends, family and the comforts of home. In May and June of 2018, I traveled through Rajasthan, India, working on a guidebook. It coincided with some of the hottest temperatures ever recorded in the region. It was normal to reach 110 degrees by 10 a.m. Not all rooms are air-conditioned. My trip to Southern India for a blogging project overlapped with monsoon season where daily power outages are the norm.
When I wasn’t fretting over deadlines, I needed to ensure I had a well-stocked supply of water and snacks instead of relying on overpriced hotel or tourist restaurants. I was, after all, still trying to stick to a budget. Even in larger cities in India, this isn’t easy. There are few corner stores, and when you do go out, you need to consider the noisy streets full of zigzagging cars, motorbikes, Tuk-Tuks and cows, which feels you’re living a real-life game of Frogger. With no stop signs and few traffic lights, the act of walking three or four blocks for a bottle of water, a soda and street food can easily take 45 minutes to an hour — more admin time.
This adventure, while absolutely amazing, is rarely the glossy experience portrayed on Instagram feeds the feature young women frolicking in floppy hats and flowing dresses. Because many falsely assume I’m having an epic Indiana Jones-style adventure (he may have battled snakes, but I’m guessing he never had to crouch in a corner swarming with ants in a cheap hotel because that was the only place the Wi-Fi worked), I don’t feel comfortable complaining to the majority of friends and family back home.
There are days when clients are difficult, the weather is challenging in biblical proportions, I can’t find Diet Coke (my one vice) and I just want a sympathetic ear. The same kind of venting that happens daily in cities across the U.S. over $15 cocktails or $2 happy-hour beers feels dirty, reeking of arrogant privilege if I do it while living overseas. I’ve developed stronger friendships with others who travel frequently because they understand that it’s a largely unglamorous lifestyle full of normal demands that just happen to be taking place in, say, Belgrade instead of a beige office in Boston. I’ve also turned online friendships with other travelers and freelancers into real-life meetups with like-minded curious souls who choose a backpack over a two-bedroom condo.
I’m not sure when this journey will end, but 18 months into this life and I’m still discovering new challenges that are ultimately making me a much stronger and more independent person. If I can stare down an angry cow in India, I’m certainly not going to balk at those that shove for a spot in a crowded subway stateside.
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