Retire Early Using Secrets From a Housesitting Diva
October 31, 2017

Retire Early Using Secrets From a Housesitting Diva

When I first met Kelly Hayes-Raitt, there were a few things that didn’t quite add up. We had met at a writer’s group in Ajijic, Mexico. Kelly was writing a book about her experience in the Middle East. She had been working with refugees. But when we met in 2014, she didn’t appear to have a job. Like most of the expats in the Lake Chapala region, Kelly seemed to be retired.

I learned that she rented out a home in Santa Monica, California. Kelly’s renters provided enough revenue for her to pay the mortgage. She had a decent-sized investment portfolio. But it wasn’t large enough to service even a modest retirement. What’s more, Kelly didn’t appear to be anywhere near retirement age. She was still years away from collecting Social Security payments.

After the writer’s meeting, she offered to drive me home. “Do you want to see where I live?” she asked. “It’s on the way.” She turned onto a steep road that climbed above the town of San Antonio. We passed some of the region’s biggest houses before Kelly stopped the car.

Kelly’s home had three massive patios. Each provided a breathtaking view of Lake Chapala below. She had a pool and a full-time gardener. “What do you pay for this place?” I asked. “Nothing,” she replied. Kelly joked about being a “housesitting diva.” She spent four months a year in the same home, caring for a dog she had grown to love.

She spent the rest of the year housesitting around the world. That’s when it dawned on me. You might not need a pension, a large investment portfolio, or even a mortgage-free home to retire in luxury. Housesitting could offer a great retirement on somebody else’s dime.

Plenty of housesitting websites exist. They include and But finding a great place to stay isn’t always easy. It can be competitive. And some of the gigs look better (and cleaner!) online than they look when you arrive.

That’s why I recommend Kelly’s new book, How to Become A Housesitter: Inside Tips From The Housesit Diva. It offers tips to finding fabulous gigs, whether you’re looking for a short holiday abroad, or whether you’re seeking a new, full-time lifestyle. The book’s first few pages include a questionnaire: Is Housesitting Right For Me? After all, it isn’t a lifestyle that’s going to suit everyone.

Her second chapter, “The Bitch & The Chow,” tells an honest account of how things can go sideways. Plenty of Kelly’s tips explain her mistakes–so you don’t have to make them.

Some of her suggestions include finding hosts with shared interests, building a solid resume that includes a short video, and starting out locally. It’s often easier to find a housesitting gig near your current home. It doesn’t require a cultural transition. You’ll know where to purchase local amenities. And, most importantly, you’ll start to build your online resume with (let’s hope!) a fabulous recommendation.

People offering their homes often insist on an interview. Kelly lists common questions and how to best respond to them. Her thorough guide is also laugh-out-loud funny. It weaves personal anecdotes with practical explanations of what to be wary of, how to deal with emergencies, how to get repeat customers and how to deal with home maintenance issues.

I’m writing this from inside a 21-foot class B motorhome in Nelson, British Columbia. I’ve been on the road for a week. In a couple of days, my wife and I will head into the United States and (if we have the guts) drive as far south as Argentina. But housesitting sounds intriguing. That’s why we’ve registered for We could drive to a location, stay for a few days, a week or a month, and build a solid resume. We could park our van and housesit in Idaho, Utah, California, Mexico, Belize, Chile, or anywhere in between.

Whether you’re trying to lower the cost of travel or slash retirement costs, housesitting might offer a road less traveled.

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