>  Flight Attendant Life   >  Getting Grounded: Homeless to Homeowner

Long before I became I flight attendant, I considered myself “flighty”.

I’ve always dreamt of far-off places. Felt restless, unsettled. Got itchy when relationships became serious, when routines stretched beyond months and into years. The thought of signing my name to a 30-year commitment gave me heartburn, just like the thought of walking down an aisle in a white dress did.

But a lot changed during 2020, including some of my ideas on “Settling down”.

On December 15, despite my chronic commitment-phobia, I managed to twist my shaking hand around the pen to sign on the dotted line. I closed on my very first home.

It still makes me woozey to think about the 30 years tucked into my mortgage agreement, or about the amount of money I’ve promised to pay. But here we are, doing it. The road to this place was winding, serendipitous, and may not have happened at all were it not for 2020’s sneaky surprises.

Read on for the story of how this free-spirited flight attendant went from homeless to homeowner in 2020. And check out this post’s companion piece: Shut The F*$# Up! The Greatest Christmas Surprise to bear witness to one of the most epic Christmas surprises of all time. (At least of my life.)

Flying High

I spent a quarter of 2019 outside of the U.S., starting with a seven-week stay in Colombia, where I immersed myself in the Spanish language and the joys of solo travel.

In October of last year I gave up my place just north of Boston and set off for Mexico City. For the next three months, I lived in a guest apartment by a lush green park on the outskirts of one of the most desirable neighborhoods in the city. I took Spanish classes at a school Monday through Friday and I explored as much as possible in my down time. I still worked in Boston, flying in every few weeks to work my trips for the month and then disappear once more into the hectic, homey streets of CDMX.

No longer having a place in Boston, when I was back for work I simply “crashed” between trips. Staying sometimes with my sister-in-law, sometimes with a guy I was dating. Occasionally I stayed at an official “Crashpad” (a shared apartment that flight attendants pay to use in between trips.) I kept warm jackets and a few changes of clothes in my trunk, so that I could be completely mobile. When coworkers asked, I joked that I lived in my car. (A joke that turned out to be not-so-funny when, in February, a rat moved into my trunk. Presumably, he thought it seemed homey too.)

From chilling in Colombia,

In early February I packed my bags, left my apartment in Mexico City to head back to Boston. But I wasn’t done yet. I wasn’t ready to give up my dreams of improving my Spanish or living abroad.

This course I was on, of living “on the go”, keeping only what I could carry and taking things in short, months-long intervals, was exactly what I’d wanted. It never bothered me to be untethered. Quite the opposite, I felt like my truest, free-est self.

I arrived in Boston with the intention of working as much as possible for two months and then setting off for a different Spanish-speaking country—the Dominican Republic—in April. The cost of living is cheap, my airline has daily flights, and I figured if I could get comfortable with the head-spinning pace of Dominican Spanish, I would be well on my way to fluency.

Unexpected Turbulence

Unexpected turbulence—an apt title if 2020 were a soundtrack—forced me to tuck my iPad away before I could click “submit”, confirming the apartment I’d selected in Santo Domingo. And by the time we landed, everything had changed.

This was early March of 2020. We received word that flight schedules would shift to match falling demand as people cancelled their bookings. COVID-19 had arrived.

A sinking, hectic feeling settled in. Of knowing change was coming but having no idea what it would look like.

We all know the story of what happened. We got scared, stayed in our homes. Restaurants closed and flights cancelled. We wore gloves and masks. We started telecommuting or we lost our jobs entirely. While healthcare workers and grocery store workers pushed on and meat packers were forced to continue showing up, even as the virus tore through their plants. And teachers and parents struggled in an unexpected new landscape of education. People worried about losing their health, their homes, and their loved ones.

And for me? The nomad living day-to-day out of a suitcase?

I had my own issues to grapple with.

toni from awheelinthesky, Mexico, teotihuacan, pyramids, mexico, pyramid, teotihuacan, mexico travel, pyramids in mexico, things to do in mexico

To making merry in Mexico...

The phrase “stay at home orders” holds a particular kind of weight when you don’t have one of those.

I stared, unnerved, at the perilous position I’d put myself in. Examining each step taken to create this life, so rife with vulnerability. I couldn’t help thinking—over and over—about the possibility that I’d done it all wrong.

I was homeless. And by choice! What had seemed like joyful, unshackled, soul-filling freedom, had suddenly started to look like a free-fall, no net underneath. I’d thrown stability to the wind in my quest for adventure and now it was backfiring.

Worry stuck to my skin in those early days of the Pandemic.

I couldn’t help thinking- over and over-
I’d done it all wrong.

Thankfully, I had a place to stay. I quarantined with a partner in Boston, and later, with my parents in quaint, beautiful Maine.

I understand that my version of homelessness was not the real deal. That the privilege of choosing to be unhoused is a world away from the reality of what other people experiencing real homelessness go through. This hit more acutely while I slept on the ninth floor of a steel and glass luxury city building. One that sits adjacent to a shelter. Seeing neighbors bundled up looking for a cigarette or spare change, carting their belongings with them. Finding, on our brisk walks through the streets of post-winter Boston, people sleeping in doorways. On the ground.

Please do not mistake this post for a “poor me.” Because the truth is, I am one of the very fortunate ones. I am one of the people whom Coronavirus, its lockdown effects, helped save.

Getting Grounded

Paired down to the essentials—eating, sleeping, exercising my brain, and going for long walks to do the same for my body—things seemed suddenly clearer. I saw a path forward in my creative endeavors. With the gift of time like I’d never had, I leaned in, practiced discipline. I started to settle into lockdown, to enjoy being grounded. I started to crave the feeling of home. An unexpected desire sprouted; to carve out a place for myself in the world.

I began to look at my missteps differently. I felt overwhelming gratitude to have traveled so much in the year before travel ceased. I felt vindicated for keeping my financial obligations light, especially after becoming debt-free for the first time in my adult life. My perspective shifted. Maybe I’d done it all right.

The feeling of settling down was sticky, and I started to look at homeownership in a new way, too. As investing in my financial future, rather than just a choking commitment. I came to crave sanctuary. Home. A place to look forward to after a long work trip or a far-away adventure.

Something I haven’t had in a very long time.

Buying the house

I looked in various cities around the country and ended up, god help me, in Providence, Rhode Island. People keep asking me what brought me there, and I keep giving them the same shrug in response. Who knows.

I was looking in cities like Atlanta and Raleigh, where the property is relatively cheap and snow is not really a thing. Instead, I chose Providence, the capitol of tiny Rhode Island, where I had the pleasure of shoveling out my four-car driveway alone after the Nor’easter that hit two days after my closing. Sweet.

The truth of how I ended up in Rhode Island is pretty simple: affordable multi-family properties. I decided that one way to make a mortgage seem less scary would be to have someone else pay it. And so, I’ll be living in one of the apartments in my home and renting the other out. This will offset my costs, allow me to continue to save and will hopefully be a great investment for future me.

Before you start worrying for me, I know it is not going to be all fun and games and cash flow. I’m going to spend more than I’m planning to, deal with things I have never thought of before, and house a problem tenant at some point. But the opportunity for financial freedom is greater right now than the fear of what headaches will inevitably arise.

Plus, we don’t act out of fear around here. We left that shit in 2018.


And despite my trash-talking the weather, I am very excited to experience my first Rhode Island Summer. It may be the smallest state in the nation, but I hear it packs quite a punch for New England Summer vibes.

To key-holding and shovel-wielding in tiny Rhode Island.


has already had some ups and downs. Shortly after signing documents, I realized that I had squatters—of the furry, bushy-tailed variety. Yep, squirrels in the roof. I hear them frolicking around while I cower in terror, praying they don’t make their way into the living space. This unexpected problem is being taken care of with the utmost urgency.

I’ve also had some incredible surprises, one being my bestie, Rachel’s sneaky Christmas plot that made me rethink this whole “humanity is a dumpster fire” thing. It was so big and kind and blow-your-mind thoughtful that I thought it deserved its own post. (And I make the rules around here.)

So, when you get a chance, if you’d like to have your faith in humanity restored just a little bit, click on to the sister post: Shut the F*$# up! The greatest Christmas Surprise.

Thank you to everyone who cheered me on and to those of you supporting me by reading this post. This year has been a wild ride, and while I’m far from sad to see it go, 2020 will always hold a special little place in my heart.


Merry Christmas, and Cheers—to finding your way home.

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  • Rae

    December 24, 2020

    I am so freaking proud of you Tone. I’m teary reading this.
    Can’t wait for Rhode Island summer!!!


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