In August of 2013, I did the scariest and best thing I’ve ever done in my life: I quit my corporate job of three years, broke my lease on my apartment in Brooklyn, packed my bags, and booked a one-way ticket to the South of France.
For the people who know me, the decision to pick up and travel was one that seemed out-of-character. I had always been a rule follower—done the things that society dictated: school then college then job then promotion, etc.
Most of my life, following the rules had paid off. I was three years into a stint at a big corporate talent agency, working in the industry I wanted to be in. I enjoyed most of my colleagues and clients (<– rare) and was effectively on a career path that was “leading somewhere.” I also had a thriving side gig—freelance writing as a ghost blogger—and I lived in a beautiful apartment in Brooklyn with my girlfriend, who I loved. (Note: still love.)
From the outside, it looked just like what I thought a mid-20s life was supposed to look like.
From the inside, however, it was a life that felt like a waste.
The impetus behind quitting my job to travel was twofold:
First: I have always been somewhat of a nomad. That is, I have always felt called to move. I distinctly remember the moment in Mrs. Balogh’s first grade class at Solomon Schechter Memphis when it dawned on me that I was now confined to a single classroom, and that meant that there were always going to be an infinite number of people in an infinite number of places doing an infinite number of things that I was never going to get to be a part of.
That moment was heartbreaking and overwhelming, but also defining; it turned me into a person who never really sat still, who spent 12 chaotic school-age years running from tennis to ballet to soccer to student council to prom committee to play rehearsal to Jewish BBYO gatherings to Christian Young Life events (really). My life was a constant state of YOLO (or was it FOMO?) as I tried to not get to the end of it all and discover that I hadn’t lived (as the Thoreau cliché would have it).
Second: I’ll admit something maybe embarrassing which is that I was actually convinced to travel by the wonderful and evil and soul-sucking and life-affirming power of my favorite social media platform, Instagram.
Around 2013, there was a growing community of people on Instagram who’d labeled themselves “digital nomads.” They were people who held remote jobs and had no homes, who connected to the world and mysteriously made an income via their computers and their smartphones. I developed a habit: watching them from the screen of my own phone, silently pining for their lives.
Their “happy hour with colleagues” was sipping rosé on a balcony overlooking the Mediterranean—not drinking cheap beer at Judge Roy Bean, the dive bar next to work. Their “today at the office” was a Macbook on a mountaintop picnic table in the rolling green Austrian Alps where Maria twirled in The Sound of Music—not a desk in a windowless cubicle littered with post-it notes and Styrofoam coffee cups. Their “daily commute” was a catamaran bringing them out to their ocean bungalow in Bali—not a two-hour subway ride in the dark, spent dodging rats and roaches and people shouting profanities and prophecies way too close to your face.
And so, with the siren song of the Digital Nomads, and the cubicle walls slowly closing in on me, I did the thing that I’d never planned to: looked at my savings and side income, calculated how much room I had left on my credit cards, figured out how I could comfortably support myself with my content writing business—then quit my job.
Since then, I’ve reallocated that monthly $2500 once spent on Brooklyn rent to living in eight countries, 12 states, and countless cities. I couldn’t even begin to tell you how many miles I’ve flown or driven, how many people I’ve met through Airbnb, or how many hotel rooms I’ve fallen asleep in at night over the past four years.
What I can tell you is this: My life as a digital nomad has undoubtedly contained its fair share of rosés on mountaintops and workdays on seaside terraces and boat trips to beautiful places. But, it’s also been a much more complex, challenging, and nuanced experience than an Instagram page could prepare anyone for.
Don’t get me wrong: I cannot begin to complain about the life that I live, and I am completely aware of how blessed and lucky I am to be in the position that I am in. I also acknowledge that it is rare to have the freedom to leave your job, and I feel grateful that my skillset aligned with a life situation and opportunity that allowed me to go.
But in retrospect, before quitting my job and jumping into nomadic life, I wish someone had been able to prepare me for the full picture of what happens when you give up your home and constantly move.
So, if you’re someone considering quitting your job and packing your bags, or simply wondering what’s really going on behind the iPhone cameras of all of those “bent-legs-on-beach-chair” photos, here are some of the surprising lessons I learned along the way.
1. You’ll realize you don’t need stuff.
When I left Brooklyn, I put all of the stuff I couldn’t bring with me in a storage unit. I didn’t actually return to the storage unit for over two years, and when I did, I discovered that every single thing in it had been decimated by mice. Cool.
At first, I was sad to lose everything I owned. But, the more I thought about what it meant to lose all those things, I realized I hadn’t used, needed, or thought about any of it in TWO whole years. The tragedy wasn’t that all of that stuff was no longer mine; the tragedy was that I’d thrown money away each month to keep stuff that added no value to my life.
2. You will constantly feel homesick for multiple places.
When I set off on my travels, I was ready for the exhilaration I’d feel when I’d arrive at each new destination, but I wasn’t prepared for actually becoming attached to a place—and finding it difficult to leave.
There are days now when I wake up wishing for the stillness and quiet of the walk to get morning coffee from Peter’s Yard in Edinburgh; the awe-inspiring and humbling views of nature you see when you go on a run in Manoa on Oahu; the cultural stimulation and insightful conversations you overhear at the Laundromat Café in Copenhagen; the warm buzz you get from drinking a sazerac and talking with friends while you listen to jazz at Vaughan’s in New Orleans.
While moving on to a new place is always exciting and invigorating and completely worth it, it also comes along with a bit of melancholy. It’s good to keep in mind that it won’t always feel easy to constantly leave things you love—and that have become part of you—behind.
3. You’ll wear the same pants for weeks straight (or no pants).
This is just a fact.
4. People won’t get it. Don’t let them make you feel judged.
True story: After I left New York, there were friends who tried to have frank discussions with me about “skewed” values; to impart their opinion that I was being irresponsible and should be saving money to buy a house and have a baby, instead of using it to travel the world.
What I learned from years of explaining my lifestyle to people is: Don’t let yourself feel judged. If the nomadic lifestyle works for you, and you can afford and are enjoying your life, there’s nothing else that matters.
5. You may lose some friends.
When you’re constantly traveling, some friends may react strangely to you. Others may simply fade off the map.
Over time, I’ve drifted away from several friends I used to feel close to. Some friendships were totally unaffected by distance, but others just petered out. This helped me realize that some of my relationships were simply built on geographical convenience.
Separate yourself physically from the people you spend time with, and you may notice that the important ones stick around—while the others fall away.
6. But you’ll also make new ones!
If you fear losing friends and feeling lonely when you travel, fear not! You will have the opportunity to make so many new friends when you explore the world.
Over the past few years I’ve met Kevin, a guy that runs a business using beetles to chew the flesh off of cow skulls until they are completely clean so people can display them as art; Micaela and Madeline, a couple of intrepid journalists dedicated to covering tough racial issues in the very-racially-charged city of Memphis; Jason, a clerk at a town general store who gave up his previous life to move to a compound dedicated to the study of American Yoga; and so many more.
Each friend you make on your journeys will bring something new and unique to your life—and you will feel richer because of it.
7. You may gain some weight (or feel out-of-sorts).
It’s only cliché because it’s true: Humans are creatures of habit. And it’s really, truly hard to maintain your daily habits or rituals when you travel.
I have always been a pretty healthy person and somewhat neurotic about my body and weight. So, in the city, I had things I did each day to help me stay fit: a fresh juice every morning, a walk to lunch, a trip to the gym after work.
However, when you wake up in a new city every week, it’s nearly impossible to stick to the same routines day-in and day-out, and this can have a tangible effect.
For me, it meant that I gained about 20 pounds during my first few years of traveling. (Note: part of it was abandoning my routine, but part of it, of course, was also wanting to taste everything everywhere I went! Totally worth it.)
Indulging in the things around you when you travel is key—and so is simply letting yourself go with the flow. But it’s also important to be mindful of the practices you do each day that give your life some order, and that you can depend on. By learning to incorporate some of the healthy habits that I had back home into my life abroad, I have been able to feel more rooted—even while moving—and have made my experience more manageable overall.
8. It will be the best thing you’ve ever done.
Of course, traveling and working remotely has its challenges and drawbacks, but in the end: It has been the most life affirming, invigorating, challenging, and growth-inducing thing I have ever done.
Embracing the nomadic lifestyle has drastically shifted the way I see the world and the way I interact with people. It’s completely changed my understanding of what a “life” is or what trajectory a person “should” take as they grow. (Hint: there is NO trajectory a person “should” take.) Lives and careers come in all shapes and sizes, and you can pick the one that speaks to your soul without worrying what other people think.
So, if you ever have the opportunity to pick up and take off to work from wherever, all I can say is: do it.