When You Work From Home, But Have No Home: Here's What It Looks Like
From the top of a Colombian mountain to a Parisian bar to a Amsterdam ferry - an uprooted remote working life is a strange one
A few months ago, I was lounging in my old college roommate’s home in Dallas. There were five of us—ex-roommates from the angsty uni years—reuniting like we do every year. The agenda? Rehashing blurry, booze-soaked memories while catching up on our more respectable life since.
Of the five us - I am naturally now the only unmarried, childless, and rootless one of the group.
I could wax poetic about that psychological Rubik’s Cube, but that’s not the point of this post.
The real moment worth sharing came when one of them, wine glass in hand, declared:
“Alright, Linds.”
We were gathered in a circle in her immaculate Dallas living room—complete with a Pinterest-worthy aesthetic, three little girls running around, and her husband presumably somewhere nearby in the neighborhood with friends. Meanwhile, I was discreetly side-eyeing the 50-foot chimney and wondering two things: 1. What’s it like to own this much house? and 2. How much does it cost to keep that chimney clean?
“I’m speaking for the group here,” she continued, “when I ask: What the hell do you do for work? Like, we’re confused. Do you work? Did you inherit millions? Hit the lottery? How are you traveling so often?”
As the rest nodded in agreement, it dawned how even those who know me intimately have no bloody idea how I live the lifestyle I have or what I do to have it.
After rest assuring that I definitely did not win the golden ticket, nor did Mee-Maw leave an amassed inheritance, I explained how I work freelance under a LLC with several different clients as a copywriter and Publicist and I - simply put - have opted out of a place to call home. Sans the 6 months I lived with my ex in a Montreal apartment (and lost thousands of dollars in that soul-crushing breakup), I’ve been rootless for nearly 4 years.
What began as a 'one summer in a van' dream from early 2021 subsequently turned into years of roaming campgrounds to countries: working any and everywhere from airport lounges, gas stations, cafes, forests, hotel lobbies, the back seat of cabs, mountain tops, and yes, of course, even a wine bar or two.
It’s glamorous. It’s tiring. It’s lonely. It’s vibrant. It all just depends on the day.
I get asked about this lifestyle fairly often. So I thought for this post I’d share five aspects about nomad life that are hard to manage (yes, of course it’s not as glamorous as IG leads us to believe) —and the one reason I wouldn’t trade it for the world.
As always, feel free to chime in! My experience of course being unique to me alone.
Tax Season: A Freelancers’ Annual Hunger Games
The most terrorizing few weeks of every year.
With double digit W-9s and no extended period of time in one state or country (I leave religiously before I have to go through the confusing hell of paying other country taxes), I’m never really quite sure where to file from or what to file exactly. Top it off with self-employed retirement and other investments, and you’re looking at mounds of numbers and documents attached to ten different email accounts and bank statements.
I finally got an accountant in 2022. After our first fruitful year together, and many, many phone calls spent hearing him try to withhold sighs, he upped his fees significantly.
I pay them without question.
When Your Office is Everywhere, But Your Wi-Fi is Nowhere
WiFi: the bane of my existence.
Finding consistent internet is a daily conundrum, and laughably it’s always at the times you least assume, and never more than when you need it the most.
It doesn’t matter if I’m in sprawling Paris, a USA campground, or wilderness Colombia, WiFi is consistently the cold-sore-inducing stress of my work life.
And I can almost daily be found darting about a mountain ridge searching for a third bar, running down a side street looking for another coffee shop to pop into, or in my van watching as my WiFi connects and disconnects in a location assured by the campground owner as “reliable.”
I’m considering Starlink this year. I’ve also began to thoroughly check Airbnbs and hotel reviews and even email management before booking. One too many dropped calls has left me traumatized.
When Your Calendar Has No Clue Where You Are
One lesson I learned far too late, and at the bitter expense of my pride, was for how smart our gadgets are — my oh my these little suckers can have a lofty time figuring out what timezone they’re in.
I cannot count how many times I dutifully memorized my calendar for the day only to end up one hour behind because my Outlook or Gmail calendars didn’t re-sync to the timezone and I failed to doublecheck.
The consequential chaos that ensues briefly as I scramble to a video call woefully unprepared or frantically cross traffic lanes to pull the van into the nearest gas station is enough to think I’d only allow it to happen once. But, alas, I am human and this has occurred more times than I care to admit (for the sake of my business reputation).
Dating People Just Like You Is Exactly What You’d Think
After my mess of heartache this year, I took a break from dating. In that break, I reconnected with a guy I had dated prior to my most recent ex. Though, when I say ‘dated’, I more mean “nomad situationshipped” because when you’re dating someone just like you — neither of you really has any idea where you’ll be.
We met at a finca in the Colombian countryside in early 2022, a week or two before he was moving to Mexico City. Over the next year, we met up in Italy, Amsterdam, Paris, Colombia, and Austin (where I’m from) and Chicago (where he’s from). It was tender, long weekends and a month of European dates following by a million WhatsApp messages and logistics of when to meet next and where.
Unsurprisingly, it didn’t work. I want kids. I want the nomad partnership. And I’m 35. Tik tok tik tok. He wasn’t really ready for the commitment yet, and while I respected that - I also couldn’t wait.
Time can of course make the heart grow fonder, but it can also stall growth in a relationship. And that’s what I felt then.
And who knows — maybe all those times we met up, all those texts, did actually bond us more come to think of it. Just in a slow-build way. Because two years later, here we are.
This time we’re actually giving it a go, we’re on the same page, and perhaps its been the years we’ve had to get to know and understand each other that led us back to one another. Time will tell.
We still prefer to nomad - only now, we’re “slow-nomadding,” with his apartment in Chicago as our base to build on. (P.S. we’re headed to Medellin in January! And hopefully Spain/Scotland in April or May! Let me know if you want to visit!)
Speaking of Kids —
I’d have 50 of them if they weren’t so expensive. That’s a lie — I’m too selfish now. But, I would ideally love to have a couple.
The issue of how and where to raise them though when you live in this way has caused me a lot more turmoil than you’d think. When you’re rooted, you get this general picture/idea of your life with kids. What school they’ll go to, the neighborhoods, the culture you’ll raise them in and around. If your parents will be close by or not.
Naturally, I want it all. But, I’ve been on the go for so long it’s hard to really know how I’ll raise my kids which leaves a weird, foggy image of the future.
I want them to speak Spanish, learn French, absorb culture, get a good education, have solid friends, stability, play music, play sports, partake in the beauty of life, hang with their grandparents.
I want them to have it all and it’s hard to know where to do that. It’s a constant conversation I have with my current partner — where do we raise them?
Again, I suppose time will tell.
At the end of the day, nomading and van life (don’t those terms make you ill?) has been a maddening, chaotic upheaval - but I’d do it no different. When I made the shift from rooted to unrooted I knew there’d be changes I couldn’t foresee.
Of the microcosm evolutions since I went effectively rootless, the one that has ultimately caught me completely off guard, but is perhaps my biggest achievement, has been the developed, almost-preferred fondness for being alone.
I feel more at peace alone than I ever have in any other partnered state. I do not mind traveling alone, eating alone, walking alone — there’s nothing I won’t do alone. Because for quite some time, I have had no responsibility to anyone except clients. And my cat.
The downside is I now act like the cat.
The jury is still out on whether that’s been a good by-product or a consequential one to partnership (being like a cat now does come with some hyper-independence tendencies I’ve needed to face while partnered again). But either way, I feel a confidence I really never had prior to this lifestyle, a trust in myself that I am capable of doing anything I want to without a partner if I want.
I remember writing at the beginning about how loneliness was causing me to self-destruct into my eating disorder (for those who don’t know me, I had anorexia for a decade and went to rehab. That’s how my writing career started with a blog.) After having been in multiple relationships back-to-back since I was 14, I found being lonely at 31 unbearable and heavily resorted back to starvation as a way to distract the lonely.
It took me a whole summer and fall to snap out of it and evolve my relationship to the loneliness. For that, I’m proud as hell. I finally understand how anorexia is a symptom, an addiction, covering discomforts in this life. Fully understanding that has helped my recovery beyond what I can put into words.
After years of anorexia, I no longer feel that intensity to use it. I’ve been lonely often, only I welcome the calmness of it rather than reject it entirely. I am comfortable hanging with myself (and usually my computer).
Whether I’m sitting in an airport terminal alone writing a SubStack post or dragging the dirty water tank from under the sink in my van to pour it into the grass and shooing Smudge from her instinctive curiosity to be in, apart, and on everything: the swat of her defiant paw to my head when I tell her “no” — I’m ultimately content with the life I’ve created. And confident that I built it without needing to insecurely duck behind the help of a partner.
Where I used to rely on partners to do anything adventurous or travel-related, I will happily go on my own now. My current partner admires this about me, though like I mentioned above — he would like me to reel it in a bit over the next couple years as we think about kids and marriage.
The steps that come after all of this free wheeling and roaming. I wonder how that will be.
As I end this post, I think about how when I was 21 I studied abroad in Galway, Ireland when I met and momentarily fell madly in love with a boy on the remote, black-rock beach island of Inishbofin (because, of course I did).
He was a local to the 300 person no-car island (only reached by ferry!) which naturally made the whole ordeal even more romantic in my young, bright-eyed brain. In the whirlwind two weeks, we spent every night at the one (and only) island pub with his family and friends and my three American girlfriends, who naturally also embarked on their own love affairs with his friends. Together, we’d doll ourselves up in our dorms and trek over to the pub to watch he and his family play music together on the rickety wooden stage while the locals welcomed us with Guinness and cards.
Afterward, on the beach at midnight, a bottle of wine at our side, we’d end the nights well into the early morning talking about everything and anything — what did we have to lose? The temporary at times the deepest connection.
I confessed my dreams for the future — of the travel I hoped to do, the history I wanted to see, the confusion I wanted to experience. Giddy and optimistic and full of hope, I’d ramble while he fingered my hair and smiled quietly.
On the final night — my girlfriends and I crammed into the pub — he got on stage with his father and sister, and as they warmed up while I settled into my chair by the hearth, he leaned over to the microphone and caught my eye with a grin: “this one’s for the American lady over there, I think she’ll favor it.”
As he winked in my direction, his friends and mine hollered and rolled their eyes playfully while I grinned foolishly like a school girl.
Blushing deeper than I ever had and likely ever will again — I listened as he and his family filled the pub room with a song I’ve never stopped playing since, no matter where I roam:
“Oh she was a rare thing, fine as a bee’s wing
So fine that I might crush her where she lay
She was a lost child, oh she was running wild
She said “as long as there’s no price on love, I’ll stay
And you wouldn’t want me any other way”
Even now, I like to think however I end up in this life — I’d look at me as a 21-year old and think: Well, I wouldn’t want her any other way.
And I’ll view that as success 💛
You live life the way that works for you Linds. You have proven to many you are smart and successful and some of us are envious of how comfortable you are when you are alone. Keep doing what brings you joy.
I’ve just found you, Lindsey, but you’re terrific, and I just subscribed. The pics in this post are wonderful - I got both my reading and art fix today through you!