Flight Attendant to Nomad Caretaker: How One Woman is Creating Her Dream Travel Lifestyle

I’ve had the travel bug for most of my life. For childhood vacations, my parents, who were on a tight budget, often took my sister and I camping at the many state parks in the Tennessee area, along with an annual extended family trip to Panama City Beach in Florida. But I think I really caught the vagabond fever during junior high during a whirlwind one-week tour of France, Switzerland, & Italy in 1990 with a small group of kids from my high school. In 1991, I lived with a family in the suburbs of Paris for three weeks. My family even hosted an exchange student from The Netherlands during my entire senior year of high school.

 

But it wasn’t until I had graduated from college (with a French degree no less) and after a divorce and several demanding jobs, that I decided to take some time off for a more thorough exploration of Western Europe. So in the fall of 1998, I set out for two months of solo backpacking & train travel in The Netherlands, Belgium, France, Spain, Italy, Switzerland, Germany & Austria.

 

That trip changed my life — I returned to Tennessee and immediately got a job, but I kept looking for an opportunity that would involve traveling (and getting paid for it)! As luck would have it, Delta Air Lines ran an ad in the local paper, specifically looking for foreign language speakers. I secured an in-person interview at their headquarters in Atlanta, GA and was hired on the spot. I graduated from flight attendant training on May 28, 1999 and immediately transferred to New York City, where I was based for the entire 6+ years I flew for Delta.

 

For the most part, I took full advantage of the free flight perks during those years, and often say I spent more time exploring the world than at home. My most frequent layover destinations were Paris and Brussels, but I was always swapping for something different: Istanbul, Athens, Rome, etc., as well as places in the U.S. that I may have never visited otherwise: Whitefish, MT, San Antonio, TX, Milwaukee, WI., In addition, my independent travels during that time led me to places like India, China, and South Korea. I had actually made a pact with myself that I would not fly for more than 10 years and, after almost 7, I gave it up to live and work full time in New York City.

 

Believe it or not, not once did I ever miss being a flight attendant after I quit. I segued into the 8-to-5 routine fairly effortlessly (in my default career of Executive Assistant). When I was able to take time off, I traveled to islands in the Caribbean, as well as Costa Rica, more of Europe, and even places in the U.S. (Hawaii, Alaska, and the Grand Canyon to name a few). After a couple of years working many long and mentally draining hours at the office and spending a lot of money just to live in NYC, I realized I needed to rethink my life and refocus my priorities. I started saving as much money as I could and getting rid of all of my material possessions with the goal of being able to take at least a year off to travel around the world.

 

As I was nearing my financial goals and starting to wrap up my life in New York, I reconnected with a childhood friend, Greg LaRowe, who was still living in Nashville where we grew up. While I certainly wasn’t looking for a relationship, because I was convinced that if I dated anyone that would end up delaying or even cancelling my travel plans and I told Greg as much in one of our first phone conversations, you can’t deny the power of love!

 

It took me the better part of a year to convince Greg that he should also quit his job and travel around the world. In the meantime, we conducted a “living experiment” and traveled around the U.S. testing out different cities where we might want to live in the future. Note that we were both still working initially; his IT job and my administrative job were compatible with the work-from-home set-up.

 

Sadly, this is before I discovered Modern-Day Nomads, so I never considered the possibility of housesitting. We primarily searched on VRBO and Craigslist until we found suitable furnished apartments and ended up spending one month in Seattle, WA; two months in Honolulu, HI; and two months in Portland, OR. We had planned to try a few places on the East Coast (Washington, DC in particular), but fell in love with Portland and decided to extend our stay there to a total of five months.

 

By then, I had quit my job and was focusing all of my time and energy on researching and planning our round-the-world trip. Greg did not resign until two weeks before our departure! We returned to Nashville and spent one month on final preparations for the trip and said goodbye to our friends and family. I had already sold pretty much everything I owned and Greg had done a great job of not accumulating a bunch of excess stuff over the years. We had no debt, no bills, nothing to worry about while we were gone. We left the country on July 31, 2010 and did not return to the U.S. until May 4, 2011. During those nine months, we visited 22 countries on 4 continents. Greg and I both blogged about the trip and you can read about our adventures here: Alethea’s Excellent Adventures + Greg’s Adventures.

 

Even before we came home, we knew we weren’t finished with our travels. We just needed some time to rest and re-energize and decided that it would be easier and cheaper to do that at home. So much for resting; Greg proposed on May 30th and we got married on July 29, 2011! After many celebrations with our friends and family in various states, we left the U.S. again on what we were now calling our honeymoon (but it really was just a continuation of our round-the-world trip) on September 4th. We traveled to another 23 countries in 92 days, returning to Nashville on December 4, 2011.

 

We already knew after our previous travels (the so-called living experiment) that we were going to relocate to Portland, OR. So on January 25, 2012 we brought eight suitcases, two backpacks, and one small safe with us on our flight to PDX. I had also packed three large boxes which we had shipped to us a few weeks later. We had rented a fully furnished one-bedroom apartment and thus had no need to buy a bunch of stuff.

 

We took our time settling in to our new surroundings and rediscovering the city we had come to love two years before. Greg eventually found a suitable job in IT and we decided my time would be best spent filling our social calendar and doing part-time work (primarily as an extra on locally-filmed TV shows). We took some closer-to-home trips (Bend, OR; Los Angeles, CA), our families visited, I flew back to Nashville once, and we volunteered at a lot of beer festivals.

 

After a great first year in our new hometown, I was starting to feel like I should be making more of a financial contribution in 2013. I didn’t start looking for work until halfway through the year though, as I had to have surgery on my hip in January and rehab lasted six months. We also had booked a big vacation (two weeks in Alaska) and I didn’t want a new job to interfere with our plans. Even then, we also decided that we would be better off if I didn’t work full time so I could still focus on my other endeavors like assisting Cindy Anderson with research for the Portland Happy Hour Guidebook, my TV work, and generally keeping up our home, planning trips and social activities, etc.

 

After meeting Tiffany Owens through an acting gig in April 2012, I started following the Modern-Day Nomads website and was intrigued by all of the job postings she shares on the Modern-Day Nomads Facebook page. I often read the descriptions and think what a perfect fit I would be, but many of the jobs aren’t very compatible with married life. I had also seen several housesitting postings in the past, just not many that were local.

 

On July 23, 2013, Modern-Day Nomads shared a job posting for a “Caretaker in Irvington.” I quickly realized that, on the surface, the position sounded like an excellent opportunity and it generally met all of our requirements (in inner Portland, nice apartment in a great neighborhood, income potential, etc.). I dashed off an introductory email to the homeowner and he replied in less than an hour saying he wanted to meet me. I would later find out that he received more than 100 responses in less than 24 hours (of which mine was one of only dozen he seriously considered) and he took the posting down the next day. After three in-person interviews spread out over two weeks (the final one was conducted at a fancy restaurant over dinner), Mark, the owner, told me that he had made his choice.

 

Our lives changed drastically almost overnight. I found out I got the job on August 9th and started working at Irvington House on August 18th. We moved into our onsite apartment on August 31st, but slept here on an air mattress some nights prior to that depending on my work schedule.

 

As the caretaker at Irvington House, a fully licensed bed & breakfast which is operated as a vacation rental, I am responsible for all of the general upkeep of the property as well as taking care of the guests who stay in the other two fully furnished apartments, which are listed on VRBO, airbnb, HomeAway, etc. Every time someone checks out, I have to clean that apartment. The 1,350 sq ft upstairs unit sleeps seven; the 550 sq ft garden unit beneath us sleeps four. So essentially, a lot of my work is as a maid, along with a fair amount of maintenance work on this built-in-1908 home. The owner, who lives in Arizona, handles all of the bookings (which I have access to via a shared calendar) and finances. I have company-issued credit cards for purchasing supplies and the use of the owner’s 2003 Nissan Xterra for running household errands. I get paid a set fee each time I clean the rental units and an hourly wage for anything else I do related to helping guests, working on the house, running errands, etc. This offsets our market rate monthly rent (which includes all utilities and cable).

 

Now that we have been here over four months, I can honestly tell you what I like most and least about working as a caretaker/property manager:

 

• Living onsite – This is both a pro and a con. Positive for the obvious reason of not having to commute to work. Negative because it’s harder to escape the job. The house isn’t exactly soundproof so we hear all the comings and goings of the guests, including heavy footsteps and loud voices on the floor directly above us. If something goes wrong, they’re knocking on our door and/or calling (at all hours). My phone has to be on 24 hours a day when we have guests.

   

• I have to work on weekends – Con. We often have checkouts on Saturdays or Sundays, and usually have guests checking in the same day. Even if no one is scheduled to check in, I still have to clean because we could always get a last-minute booking. The window for cleaning is between 11AM-4PM. We essentially have to plan our days, especially mine, around what needs to be done at the house.

   

• The unexpected – This house is over 100 years old. Things break, often. The owner spares no expense, which is a blessing. But that doesn’t prevent the inevitable clogged toilet, shorted electrical outlet, furnace malfunction, etc. Just when I think everything is under control and I’m making progress on my lengthy To Do list, something else happens.

   

• It’s a lot of work for one person, especially if you have other responsibilities. Greg usually helps out with the weekend cleanings and we do have a backup cleaning company that we can use if necessary. I spend a lot of time corresponding with guests, purchasing supplies, keeping things neat and orderly, and fixing problems. It averages out to about 40 hours per month for administrative and maintenance work with cleanings adding another 40 hours. But I work, in some form or another, for Irvington House every single day!

   

• A big plus: the living quarters. Our apartment is beautiful! Huge windows in the main living and dining areas, built-ins, high ceilings, upgraded kitchen appliances including a dishwasher (Greg’s favorite amenity since this would be his job otherwise). We also have shared use (with our guests) of the spacious back patio and outdoor grill and a garage where we can store and work on our bikes.

   

• The opportunity to meet nice people – The rental units are truly self sufficient with lockboxes so the guests can check in and out on their own. There have been plenty of guests that I didn’t meet or even see; our paths never crossed. It’s not like a B&B where the innkeepers make a point to greet the guests and then are serving them breakfast every morning and tea or sherry and cookies in the afternoon. But I have enjoyed the interactions I’ve had with our guests and would probably prefer an environment that was more conducive to socializing.

   

One other issue: Our almost 1,000sq ft apartment came completely unfurnished and we still had very little more than what we brought to Portland in suitcases! We didn’t want to spend a lot of money unnecessarily, so I immediately started scouring Craigslist for as much used stuff as possible. As it turned out, there were a lot of moving sales in Portland in late August and we were able to buy about 70% of our furnishings secondhand. We managed to get everything we could possibly need for under $2,000.

 

Greg and I both agree that, while we love Portland, we want to keep our lives as simple and untethered as possible. Having to furnish an apartment was not in our plans but we decided it was worth the experience of living and working at Irvington House. Besides, we have no attachment to our new used possessions and can easily sell it all when necessary.

 

Our one-year contract expires at the end of August. While neither of us is ready to move on just yet, our experience here has made us more aware of the possibilities of other jobs as caretakers, property managers, house sitters, etc. We’ll be watching Modern-Day Nomads closely, of course!

 

~Alethea Smartt LaRowe