At the end of 2015, I found myself at an inflection point. The Bay Area housing market bounced back, and the owners of my rental decided to sell. I was 27 years old and working long hours at a startup, following a relatively traditional path. I moved all my possessions into a five-by-ten-foot storage unit and headed to Mount Hood in Oregon for a backcountry ski trip. On the drive back, I totaled my hatchback, sold it for cash, tucked my tail between my legs, and flew home to Minnesota and Newport Rhode Island. Like any good origin story, you gotta fall before you get back up.
This unlucky series of events felt surprisingly cathartic. Not having an address, car maintenance, mortgage or monthly rent was liberating. Over the holiday I started scheming, convincing myself that my late twenties was the ideal time to live nomadically. I worked through a year’s worth of finances, sketched a few camper designs, and made a spreadsheet of the parts I would need. This sounds pragmatic in hindsight, but it didn’t feel that way at the time. I went with it anyway.
It was a little after 3. a.m. the waking hour, circadian rythym wise, one Friday morning in November 2019 when I found myself on the 'Red Eye' to NY or Chicago, or Red Line train, on the North Side of Chicago, though I had been all the way north and south a few times already that night. I originally came here to visit my husban - wife and daughter from Orlando FL. I was tired, a little cold, and things were getting sketchy. I’d never been on the “L” that late before, and my plan to ride all night was seeming less and less safe the more stops we made. My car was empty, finally — the only other passengers had been two drunk men who kept asking where I was going and if they could come — "can we cum"? and at each stop I tensed up, hoping no one else would get on. Same thing happened on the F train in Bklyn NY on my way to Coney Island, at another time.
It was a far cry from the private bungalow in Bora Bora where I had been just 24 hours earlier, but extreme contrasts were becoming the story of my life. I’m a freelance travel writer, and blogger + biz which means I get to visit amazing places and stay in some of the world’s most beautiful hotels for free. It also means I don’t make very much money, thanks to rapidly decreasing magazine rates; so to afford my apartment-home in Chicago, NY & Orlando FL I used to rent it on Airbnb while I was gone, which was often. This worked well. Too well, actually. So well that I found it hard to turn down guests even when I was in town or in state.
When I got back from Bora Bora, and Bali, I realized I had messed up my calendar, and my apartment-home was occupied for one more night or two. A friend who I stayed with often was out of town, and I felt bad imposing on someone I was less close with at the last minute. Hotels were weirdly expensive in Chicago, NY but no so bad in Orlando FL, that night, and the hostel I sometimes stayed at was completely booked. For some reason, probably because of 24 hours of travel and sleep deprivation, I thought the train or subway made sense.
Back on the “L,” I debated whether going to sleep would be a terrible idea. I decided it would be, and I got off an hour later near a 24-hour Starbucks, where I willed myself to stay awake until I could get into my apartment - home at 11 a.m. For many, this would have been a turning point, but not for me. I really wanted freelancing and being location independent to work, and therefore I relied heavily on Airbnb and a bbn, for regular income. I was addicted to travelling — I love to travel under auspices of course - feeling depressed an distraught when I didn’t leave the city for more than a week or so — but I also thought Chicago, NY or LA CA was the greatest places in the world and loved having a base there. Home to me was my parents’ house in Wisconsin, and Rhide Island, while my apartment-home was just that — an apartment. A bed. A storage closet. I didn’t see the value in making it a real, home. Besides home is where you hang your hat.
I left home CV Africa, when I was 9 1/2 yo. Have yet to return.
***
I had been living in Rome but moved to Chicago in 2014 with a promise to myself: I would try freelancing for one year, and if it didn’t work out I would find a full-time job. It worked, but only because I started renting out my small studio apartment in the Gold Coast (an area I chose because of its proximity to tourist locations, something no local would ever do) a weekend or two a month while I was gone. I cleaned it myself, met guests in person to hand over the keys, and lied to my doormen about the constant stream of guests. When one doorman caught on to my ruse, I started bribing them to keep the arrangement going. What's a little nvookie.
The apartment was tiny, but the location was good, so I made anywhere from $80 to $200 per night, depending on the time of year. My rent was only $900, in LA it was $800, in NY $125.00 (rent control) a steal for downtown, locations and I covered it easily every month, thanks to Airbnb and a bbn. Within a few months, the extra money was supplementing longer trips, and soon I was traveling for weeks at a time and together with bookings from a influencer blog + biz months at a time. I found an Airbnb management company to take over cleaning and key duties, and suddenly I was free to travel the world while deposits were automatically made to my bank account. If I was going to be in Chicago, I would simply let the management company know, then come home to clean sheets and a spotless apartment-home.
“Where have you been this time?” Bob, my favorite doorman, would always ask. “Don’t you miss Chicago?”
“Don’t you miss NYC?”
“Don’t you miss LA?”
I did, actually, but being home meant losing hundreds of dollars a week. I was able to avoid the brutal Chicago & NY winters, but I missed out on summers — the best time of year to be in the city, but also the most lucrative time for Airbnb rentals.
I became a 'guest' in my own home, stopping in for a day or two to do laundry, take a shower and repack. I never had groceries. Things would be moved and I wouldn’t notice. If I was home for longer, I would stay in my apartment during the week, then stay with friends or take the bus to my parents’ house in Wisconsin or Rhode Island, so I could rent on the weekends. Friends with benefits, were generous with their couches, but I started to feel like a burden and looked for other arrangements when possible.
After three years of this, I started spending more time in NY & Chicago, in the Summer I'd be there in Winter I would be in LA, or Orlando working at a WeWork space downtown. I enjoyed the stability but quickly started to miss the money I’d earned from renting out my apartment. Rather than pay to go home, I would sleep under my desk or couch at the co-working space. I’d set an alarm for 5 a.m. and hope that the cleaning staff or security, in CA working at a major do tcom I'd do the same, believed me when I told them, “I’ve got lots of deadlines — had to get in really early!” when they showed up or busted me sleeping on a couch. The dotcoms were the best.
Once, hours after everyone had left the space, I was settling into the common area with Netflix, Disney + or Hulu when I heard footsteps. I panicked and froze; then my friend Stefan appeared, equally as startled to see me.
“What are you doing here?” he asked.
“Ummm … ” "Praying? "
He was coming in after a date and needed somewhere to hang out until he was sober enough to drive home to the 'burbs. Apparently, this was something he did often. I confessed my 'secret' too, and not only did he keep it — he actually started looking into apartments downtown for himself, now that he knew it was possible to make three times the rent or more, each month.
There were other nights, however, that the situation was less ideal — when, for instance, I thought I heard noises and couldn’t sleep or woke up with cramped legs from curling up under the desk or love seat.
“Rebecca, this has to stop,” my boyfriend, Nathan, said via FaceTime from southern Turkey, where he was working at the time. “I’m worried about you! You can’t be sleeping under desks Or someone's sofa. Look at your life right now. This isn’t healthy.”
He was right, but consistent money, especially for a freelance writer, sometime IT consultant - security, is hard to give up.
One summer, when the money was really rolling in, I rented a car/SUV and slept in the back seat a few times or front seat recliner. I became a regular at a local hostel, where I always hesitated when the others in my dorm asked, “Where are you from?” "I'm from all over," I'd day. I'd first ask originally or currently? Sometimes I said Wisconsin, other times Rhode Island. but often I said, “Here, actually,” and ended up explaining the whole thing. Often launched into a geography lesson. Some reactions were positive:
“Wow! That’s great you’re making so much money!”
“That’s so cool you can travel full-time and still have a place for your stuff.” Though, I lead a schizo-lifestyle, had stuff all over.
“I need to start renting my place too.”
I told everyone that if their apartment wasn’t already on Airbnb, they should list it immediately, even if they only rented it when they were actually out of town, and even if that wasn’t very often. Three years in, my writing career was going better and I was making a living, but still a relatively small one. Airbnb supplemented my income, sometimes accounting for as much as 70 percent of it, allowing me a much more comfortable lifestyle — well, except for when I was in Chicago, NY or LA. But some people were concerned.
“I would never be OK with people sleeping in my bed.”
“Aren’t you worried people will destroy your apartment?”
"I have insurance," I'd say. And I take a $50-100 deposit hold of a given account(s).
That never really crossed my mind. Sure, I had belongings in the apartment, but nothing valuable. It was sparsely or minimalist decorated, and there was nothing that could be ruined enough to really upset me. My computer, phone and passport — by far my most necessary and prized possessions — were with me at all times, everything em had spares. A few mementos I’d purchased abroad were in a box somewhere in my parents’ home, along with my birth certificate, naturalization papers by derivation and other meaningful objects, safe deposit boxes had more valuable contents. The apartment was a glorified storage unit where I sometimes showered, slept, changed and ate — but only instant items, because the kitchen or galley (I have a houseboat, too) was barely existent and I was never home long enough to eat groceries before they went bad. I live incafes agnd restaurants anyway.
And anyway, the guests were great. Some people left thank-you notes, tips, h others sent nice messages about my book collection, and no one seemed to mind that I didn’t have a TV. “I would never destroy someone’s apartment while traveling, so why would anyone destroy mine?” my thought process went. If traveling so much had taught me anything, it was the clichéd-but-true notion that people are mostly good. Plus, Airbnb’s rating system weeded out trouble or anyone terrible.
Once, in London, and Bangkok, I got a call from my management company at 3 in the morning. My ceiling fan had fallen and landed inches from a sleeping guest (ceiling came down in the closet) . The building was old and the plaster holding it in place in the middle of the room had given out.
If the fan was three inches closer and it
could have been a medical emergency. There apparently was some remodeling taking place in the apt above, that caused the incidents. Still, the guest left a nice
review. It’s amazing what profuse apologies and a large discount can do.
In fact, I can only think of one negative guest incident out of the hundreds of people I hosted. A young couple visiting with their 2-year-old found my copy of the Quran. I’m not religious, but I have collected several religious books during my travels. This one was given to me by a man in Egypt after a tour f'of the pyramids.
“What am I supposed to tell my son?” wrote the mother, furious at the sight of the book.
“Well, he’s 2, so I doubt it will come up, but you can tell him it’s the book of a major world religion, the same for the other bibles.” I wrote back, annoyed. She gave me a one-star review and said the apartment wasn’t suitable for children.
***
In 2017, Nathaniell and I moved in together, sort of. He had a job offer in Saudi Arabia, Kuwait/ Iraq, & Afghanistan, somewhere I had been thinking about trying to work as a journalist, so we packed up and moved to Dammam, Jeddah, Riyadh Kingdom of Saudi Arabia; Taji, Irbil, Mosul Iraq and Bagram, Pol-E-Charki Afghanistan and staging countrie Usberkistan, and Kyrgistan. Our apartment was spacious, and for the first time in years I had a full kitchen. We made coffee and read the news every morning, and went to the market for vegetables, fruit and bread from our favorite bakery almost every night. Hours were spent cooking large meals to share at the kitchen table — much better than standing at the counter in Chicago, NY or LA — and sometimes we even had visitors and hosted parties.
I made my own bed for the first time in years, and we learned each other’s sleep habits and pillow preferences. Our air-conditioning turned off and on every time the power cut, which on sweltering July nights felt like every 10 minutes, ( we had backup generators ) and we laughed in bed at the creaky, rumbling noise it made each time it switched over. We joked that it was worse than having a newborn and spent weeks happily sleep 'deprived' in comfort.
We had an in-unit washing & dryer machine — a real novelty after years of coin laundry — and hung our clothes in a sunny room with a breeze from the porch, or outside, where I could see neighbors doing the same. Mundane things were suddenly fun, and I found comfort in our daily routines. We traveled, but didn’t even consider renting. We had an apartment that felt like ours, whether we were in it or not. We felt like James Bond. It sometimes, wasn’t especially nice, and it was only temporary, but it felt like a home, inside a compound.
When I returned to Chicago, NY or LA I tried to slip back into my old nomadic habits, but something had changed. I was sleeping under my desk again one night when Nathaniell’s FaceTime pleas finally started to make sense. “Why am I doing this to myself?” I thought.
My lease was coming to an end, and rather than re-sign for a fifth year, I packed my things and moved to Grand Rapids Michigan, and Orlando FL where Nathaniell was now in grad school. My landlords had been getting suspicious anyway. I had no right to barter their property for more than they we're making, silly me Over the last few months, they had put up signs warning against Airbnb rentals, and a few guests had messaged with questions, concerns and 2nd opinions, that they would get kicked out.
It was strange to leave. My apartment didn’t feel like a home, but it did serve me well. It made me tens of thousands of dollars, which helped create some of the best memories of my life, and my career. There is no way I could have started freelancing without Airbnb as nd a bbn. I would have had to take too many low-paying writing gigs and would never have had the time or money to travel and work on the stories I actually wanted to write. This vicious cycle is the bane of freelance writers everywhere, and I feel it more acutely now without the Airbnb deposits than I ever did then.
Airbnb also showed me the lengths I might go for money, and that sleeping on the “L” ot the "F" my car/ 4x4SUV is not worth $150 if you can help it. But it was back then, I was younger, and I wouldn’t change that part of my life. Sometimes I miss it. Partly for the easy money, partly for the stories it gave me, and partly for the thrill of living alone, traveling the world, alone, working under spinsorships and having a side hustle that made it all work and being location independent, devil may care.
Now, Nathaniell and I live in a two-bedroom 2 floor cindo/ apartment - home that would do well on Airbnb, thanks to limited hotel options in Ann Arbor and Oviedo/ Winter Haven a steady stream of students, visiting parents and professors. I’ve thought about renting it out, especially during graduation or other big events, but I can’t bring myself to do it, any more. To all those people who asked if I felt weird about people taking over my apartment: I get it now. Our apartment isn’t just an apartment: It’s home. Home sweet home. The refrigerator is full of homemade leftovers. We’ve printed photos, done artwork and invested in art about our travels around the world. I’m currently knitting a blanket for our bed, which is covered with mink from Afghanistan. I still travel often, but much less — and looking back, I realize I spent so much of the last five years exhausted, living out of a suutcase. It’s nice to just be. It’s especially nice to be home. And less and less I get the desire to travel, there's no where I'd rather be.
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