I walked onto the patio that extended from the top floor of Kelly’s house. Like the patio on the floor below, and the floor below that, it had a giant living space with comfy chairs and sofas. The dramatic view of Mexico’s Lake Chapala extended east and west, as far as I could see. Kelly also had a private swimming pool.
I didn’t want to be rude, but I had one burning question. “What do you pay for this place?”
Kelly smiled. “Nothing.”
In 2010, Kelly Hayes-Raiit joined trustedhousesitters.com. It helps homeowners or house sitters find a perfect match. In some cases, a homeowner may want to take a holiday. They just want someone to tend to Buster the cat… or the family python.
There are also thousands of wealthy people who own multiple homes—occupying each during different times of the year. They might spend winter in Asia, spring in Argentina and summer in the south of France. Many refuse to rent out their properties. Instead, they want a trustworthy person to live in their homes. In most cases, they’re asked to care for a pet.
Some people, like Kelly, housesit full time. She used to work as a political consultant. “I was a spokesperson to protect women's rights, consumers' rights and the environment. I loved it! I ran for elected office myself in 2006, got my ass kicked and decided to take a break from politics.”
She took two trips to the Middle East. The first was 5 weeks before the US-led invasion of Baghdad. She took a second trip to understand the affects of the war on Iraqi refugees. With a burning story to tell, Kelly couldn’t go back to work. She wanted to write a book instead. Housesitting offered the perfect solution, slashing her cost of living. She now rents out her Santa Monica home. Kelly lives off the rental proceeds, along with money she earns from her column with the Argonaut News.
You can see multiple housesitting sites online. They includemindmyhouse.com, housecarers.com and caretaker.org. But trustedhousesitters.com is the biggest. Laurence Bresh is the company’s chief marketing officer. He says they match roughly 20,000 homes with sitters each year. They have about 60,000 members. More than 5000 homeowners have properties posted.
I paid the annual subscription of $95.88. Then I signed up for their email alerts. Housesitters can specify where and when they’ll be available. I kept my dates and destinations flexible. Postings from all over the world began to flood my inbox.
The latest says, “URGENT! House sitters cancelled at last minute: 3 dogs, 3 weeks in Seychelles.” It gives dates (May 22nd to June 17th) and describes expectations.“Three lovely dogs need lots of love…they need a walk of at least an hour a day, feeding, cuddling, playing and grooming.”
Housesitting assignments can be as short as a week, or longer than a year. Kelly found a sweet spot in 2010. “I fell into a housesit [in Lake Chapala] that became a recurring sit every spring and fall. I've been with this family, house and dog for 5 years now.” She has also stayed in the US, the UK and Copenhagen, Denmark. This summer, she’ll be in Malaysia and Singapore.
The lifestyle, however, does have its drawbacks. “I live my life around other people's schedule, other people's routines, even other people's stuff,” says Kelly. I always assume I'll spend about $100 of my own money to purchase things that make my life easier. For example, I can't count the number of coffeemakers I've purchased and left behind!”
If you’re wondering whether you might like to housesit, take Kelly’s questionnaire at trustedhousesitters.com. If the lifestyle suits you, your score will be low. If your scores are high, you had better book a hotel.
Dalene and Pete Heck are also veteran house sitters. Their travel blog at heckticktravels.com is one of the best I've ever seen. National Geographic named them 2014 Travelers of The Year. Before leaving their corporate jobs to travel full-time, they met an elderly couple in Ecuador. “They had been house-sitting for a staggering 16 years! Six years had been spent in Costa Rica alone, where they bounced around from house-sit to house-sit, but accepting only those jobs that were at least 6 months in duration.”
Dalene and Pete wrote an eBook, How To Become A Housesitter And See The World. They explain the perks of housesitting, where to find homes, and how to attract homeowners. They list 18 websites from which homeowners or housesitters can find suitable matches.
These sites are shifting paradigms. Those who couldn’t afford to travel may now find that they can. For others, they're tickets to a life of luxury on somebody else’s dime.
Andrew Hallam is a Digital Nomad. He’s the author of the bestseller, Millionaire Teacher and The Global Expatriate's Guide to Investing: From Millionaire Teacher to Millionaire Expat.