It was a little after 2. a.m. one Friday morning in November 2016 when I found myself on the 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 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 — and at each stop I tensed up, hoping no one else would get on.
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, which means I get to visit amazing places and stay in some of the world’s most beautiful hotels. It also means I don’t make very much money, thanks to rapidly decreasing magazine rates; so to afford my apartment in Chicago, 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.
When I got back from Bora Bora, I realized I had messed up my calendar, and my apartment was occupied for one more night. 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 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 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 at 11 a.m. For many, this would have been a turning point, but not for me. I really wanted freelancing to work, and therefore I relied heavily on Airbnb for regular income. I was addicted to travel — feeling depressed when I didn’t leave the city for more than a week or so — but I also thought Chicago was the greatest place in the world and loved having a base there. Home to me was my parents’ house in Wisconsin, while my apartment was just that — an apartment. A bed. A storage closet. I didn’t see the value in making it a home.
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.
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, a steal for downtown, and I covered it easily every month, thanks to Airbnb. Within a few months, the extra money was supplementing longer trips, and soon I was traveling for weeks 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.
“Where have you been this time?” Bob, my favorite doorman, would always ask. “Don’t you miss Chicago?”
I did, actually, but being home meant losing hundreds of dollars a week. I was able to avoid the brutal Chicago 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 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 so I could rent on the weekends. Friends 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 Chicago, 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 at the co-working space. I’d set an alarm for 5 a.m. and hope that the cleaning staff believed me when I told them, “I’ve got lots of deadlines — had to get in really early!” when they showed up.
Once, hours after everyone had left the space, I was settling into the common area with Netflix 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 … ”
He was coming in after a date and needed somewhere to hang out until he was sober enough to drive home to the suburbs. 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 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.
“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. Look at your life right now. This isn’t healthy.”
He was right, but consistent money, especially for a freelance writer, is hard to give up.
One summer, when the money was really rolling in, I rented a car and slept in the back seat a few times. I became a regular at a local hostel, where I always hesitated when the others in my dorm asked, “Where are you from?” Sometimes I said Wisconsin, but often I said, “Here, actually,” and ended up explaining the whole thing. 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.”
“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. 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?”
That never really crossed my mind. Sure, I had belongings in the apartment, but nothing valuable. It was sparsely 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. A few mementos I’d purchased abroad were in a box somewhere in my parents’ home, along with my birth certificate and other meaningful objects. The apartment was a glorified storage unit where I sometimes showered, slept and ate — but only instant items, because the kitchen was barely existent and I was never home long enough to eat groceries before they went bad.
And anyway, the guests were great. Some people left thank-you notes, 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 anyone terrible.
Once, in London, 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. The building was old and the plaster holding it in place in the middle of the room had given out. Three inches closer and it could have been a medical emergency. 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 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,” I wrote back, annoyed. She gave me a one-star review and said the apartment wasn’t suitable for children.
In 2017, Nathan and I moved in together, sort of. He had a job offer in Iraq, somewhere I had been thinking about trying to work as a journalist, so we packed up and moved to Erbil. 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 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 — 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, and we laughed in bed at the creaky, rumbling noise it made each time. We joked that it was worse than having a newborn and spent weeks happily sleep deprived.
We had an in-unit washing machine — a real novelty after years of coin laundry — and hung our clothes in a sunny room with a breeze from the porch, 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. It wasn’t especially nice, and it was only temporary, but it felt like a home.
When I returned to Chicago, I tried to slip back into my old nomadic habits, but something had changed. I was sleeping under my desk again one night when Nathan’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 Michigan, where Nathan was now in grad school. My landlords had been getting suspicious anyway. Over the last few months, they had put up signs warning against Airbnb rentals, and a few guests had messaged with concerns 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. 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” is not worth $150 if you can help it. But it was back then, 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, and having a side hustle that made it all work.
Now, Nathan and I live in a two-bedroom apartment that would do well on Airbnb, thanks to limited hotel options in Ann Arbor and a steady stream of 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. 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. The refrigerator is full of homemade leftovers. We’ve printed photos and invested in artwork. I’m currently knitting a blanket for our bed. I still travel often, but much less — and looking back, I realize I spent so much of the last five years exhausted. It’s nice to just be. It’s especially nice to be home.
Rebecca Holland is a freelance writer based in Michigan, where she writes about travel, food and other topics. You can find her work in AFAR, Saveur, The New York Times, and elsewhere. She’s also the founder of Curiosity Magazine, a magazine for socially conscious travelers.