“Compassionate Listening” With Candice Georgiadis & Kelly Hayes-Raitt

Compassionate Listening is a fabulous training that teaches people to listen for and appreciate the underlying values of someone’s message, rather than concentrating on formulating your next point. As part of my series about “exciting developments in the travel industry over the next five years”, I had the pleasure of interviewing Kelly Hayes-Raitt. Kelly has […]

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Compassionate Listening is a fabulous training that teaches people to listen for and appreciate the underlying values of someone’s message, rather than concentrating on formulating your next point.

As part of my series about “exciting developments in the travel industry over the next five years”, I had the pleasure of interviewing Kelly Hayes-Raitt.

Kelly has been traveling full-time for the past decade as an international housesitter where she lives in strangers’ homes and cares for their pets while they go on vacation. She’s housesat throughout Europe, North America, SE Asia and Africa and has written How to Become a Housesitter: Insider Tips from the HouseSit Diva.

Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

I didn’t wake up one morning and declare, “I’m going to be a housesitter!” My current traveling/housesitting lifestyle evolved. During a mid-life career change where I decided to write a book about my experiences working in the Middle East with refugees, I realized I could create a positive income stream by renting out my home and living elsewhere rent-free.

Initially, I applied for (and won) free residencies at writing colonies, but those are competitive and expensive to apply for. After I housesat for a few friends and relatives, I realized housesitting was more flexible and offered a wider range of opportunities.

I don’t get paid for housesitting. I live in other people’s homes and care for their pets, gardens and homes while they vacation. I don’t pay any expenses either, so it’s a quid pro quo. I enjoy living like a local in a neighborhood that’s not in a tourist area. I enjoy secure wifi, a clothes washer, a kitchen, usually good cable, free parking, privacy, (usually) a garden and sometimes a pool…and a furry friend or two!

My first international housesit was in east London during the Olympics! Every time I rode the Tube, I went past the Olympic Village. The city was alive, and I was there on-the-ground experiencing it like a local. I was hooked!

Can you share the most interesting story that happened to you since you started your career?

Just one story? While housesitting in Berlin at the height of the Syrian refugee crisis, I volunteered at a registration center and interviewed newly arrived refugees. I attended the 70th commemorations of the bombings of Hiroshima and Nagasaki while housesitting in Osaka. I snorkeled with mama and baby humpback whales while spoiling pets in Réunion (a French island east of Madagascar). I launched my housesitting book at an event while housesitting in Mexico, and raised money for a shelter helping Central American refugees.

I’ve made lifelong friends with other housesitters and with the homeowners whose homes and pets I’ve cared for.

I joke I sleep around — usually with pets. The truth is, I’ve created a whole new life for myself that is remarkably soul-fulfilling.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

At that glorious east London housesit during the Olympics, the cat brought in a late-night gift: An eviscerated mouse she lovingly left in the doorway to the bedroom. I nearly stepped on it in the middle of the night when I got up to use the bathroom! Lesson learned? Wear sandals — always!

What do you think makes your book stand out? Can you share a story?

I wrote How to Become a Housesitter because I realized too many people were glorifying the lifestyle — myself included! I love housesitting, and I love giving pet owners the opportunity to travel knowing their pets are loved and their homes are secure.

But, it’s not for everyone. I include a quiz “Is Housesitting Right for Me?” right in the beginning. After buying my book, an acquaintance insisted on buying me dinner.

“Please don’t take this the wrong way,” she said, “but I’m not meant for housesitting and you just saved me a bundle!”

I present housesitting honestly — the responsibility, the insecurity, the uncertainty, the just plain nuttiness that can sometimes be involved when dealing with strangers.

I also write about the unexpected joys and about the nuts-and-bolts: how to get started, how to evaluate housesitting assignments, how to break through the competition, how to get asked back.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Housesitting is work and a huge responsibility. In ten years, I’ve encountered all types of situations: Something goes wrong with the house, or the pets, or the travel plans…

Constantly putting myself in new situations, while exciting, takes a lot of energy. Even “new” gets old! I avoid “burn out” by keeping up the relationships I have with homeowners of my favorite housesits so I can be first in line when they travel again. Repeat assignments remove a lot of the unknown factors that can be stressful and the familiarity feels like I’m coming “home.”

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

It’s a cliché to thank your mother, but all the necessary traits I draw on to be a conscientious housesitter were instilled by my mom: a love of travel and adventure, the gift of flexibility, a sense of humor, orderliness, and gratitude. I never thought I’d thank my mom for insisting I make my bed every morning!

Let’s jump to the core of our discussion. Can you share with our readers about the innovations that you are bringing to the travel and hospitality industries?

Housesitting is a relatively new component to the travel industry. For years, friends or friends of friends may have stayed at pet owners’ homes while they were away — or popped in to walk the dog or feed the kitty.

One of the earliest web sites that posted pet owners’ pet sitting needs and profiles of housesitters willing to care for pets is, which has now expanded into the world’s only bilingual housesitting web site.

Now, there are 50 housesitting platforms where homeowners and housesitters can peruse each other’s profiles to see if there’s a match. Some of the platforms are country-specific, such as Others are international, such The largest (and most expensive and most competitive) is

As a new kid on the “sharing economy” block, housesitting is such a game-changer for travelers — and for pet owners who would otherwise be tied to their homes by their pets’ needs.

Which “pain point” are you trying to address by introducing this innovation?

Housesitting is a true win/win. Pet owners who otherwise might not travel can do so without expensive (or dangerous) pet boarding, and travelers can travel more authentically. As a digital nomad who can work from any place where there’s wifi, I love the amenities a home offers (as opposed to a hotel room), the variety of locations available to me, and the huge cost savings.

How do you envision that this might disrupt the status quo?

Well, I don’t get many invitations to stay at chain hotels!

Can you share 5 examples of how travel and hospitality companies will be adjusting over the next five years to the new ways that consumers like to travel?

International and domestic housesitting continues to grow, just as the type of travelers who are attracted to housesitting continues to grow. I believe that trend will continue. Here’s why:

1. More retirees are exploring living overseas in countries where their dollar stretches further. In fact, during the decade ending in 2017, the number of American retirees living abroad leapt by 40%, according to the U.S. Social Security Administration. Housesitting provides an on-the-ground opportunity to experience day-to-day living in a foreign country before making a major move. It’s a great solution for retirees.

2. Last year, 32 million American women traveled alone. Housesitting provides a safer experience for all travelers, but particularly for women. Individual homes are generally in neighborhoods away from the “touristy” areas that attract scammers and pickpockets and they have better security than typical hotel rooms — and they may come with a watchdog!

3. In the U.S., 4.8 million workers describe themselves as digital nomads. Housesitting provides them with a better travel/work experience: faster, more secure wifi; dedicated, private work space; and more control over their work environment than a hotel or hostel provides.

4. Increasingly, travelers are seeking “authentic” experiences. A recent Trip Advisor study reports that experiences such as cooking classes and culinary tours each increased by 57% among international tourists. Housesitting is just about the most genuine way to explore a new destination!

5. As I write this, much of the world is emerging from COVID-19 lockdowns. Since staying in someone’s home — that has been thoroughly cleaned — can be far less germy than staying in a hotel or hostel where there‘s more exposure to and turnover of customers and personnel, travelers who might not have considered housesitting in the past might see it as a safer option for travelling in the future.

You are a “travel insider”. How would you describe your “perfect vacation experience”?

My perfect vacation experience is the magical combination of great digs in a fabulous location that involves rolling out of bed and finding coffee, opportunities to engage with local people, a day (or more!) of scuba diving, visits to great art museums and a feeling that I’m contributing to the community I’m living in.

Can you share with our readers how have you used your success to bring goodness to the world?

I don’t know that I’ve brought “goodness” to the world, but I have given pet owners peace of mind when they travel. I think travel is transformative. Any way I can encourage or inspire people to travel — either by reading my book or by trusting me to care for their pets — is a “win” from my perspective. And I’ve certainly scratched a lot of furry tummies!

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Compassionate Listening is a fabulous training that teaches people to listen for and appreciate the underlying values of someone’s message, rather than concentrating on formulating your next point.

How can our readers follow you on social media?

I share tips on how to get started in housesitting on I also post fun interviews that I hope inspire travelers to try this option! My book How to Become a Housesitter: Insider Tips from the HouseSit Diva is also available on my site as an ebook.

Many housesitters are bloggers and writers. I share many tips for overcoming writer’s block (or, really, any creative blocks) at My eBook Jump Start Your Book: Practical Tips for Harnessing Cutting-Edge Brain Science to Beat Your Writing Blocks and Unleash Your Creativityis also available.

Happy travels!

This was very inspiring. Thank you so much for joining us!

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