Life Less Ordinary: Caretaking 101: 5 Tips for Becoming a Professional Nomad

And even though it’s only been 4 years and we still have a lot to learn, we’ve come a long way from where we started. We’ve managed a hiker hostel, managed a restaurant/bed and breakfast, were innkeepers for a remote, off-the-grid lodge and currently we are property caretakers a private island. We thrive on collecting these varied experiences, and each one helps us grow and learn as a team (and learn to pack lighter and lighter).

Everyone wants to know how we do it and where do you find these jobs … so we thought we’d share 5 tips, plus the best resources, for anyone thinking about stepping outside the box and into a nontraditional, nomadic life.

Housesitting is the best place to start. We started as cat sitters for our landlords. Think it’s not much? It is; if you do a good job, you’ve gotten yourself your first reference. And having good references is imperative. Don’t be afraid to put the word out to friends and family to gain “experience.” We did that right after the Appalachian Trail and ended up with a few housesitting gigs. This is also something you can do even while working your “real job.” We have a few sets of friends who have full-time jobs, but never pay rent whenever they are because of housesitting gigs.

Most housesitting gigs do not pay. It is merely an exchange for accommodation. But, any time you add in other duties—cleaning toilets, milking cows, etc.—that’s when you start to make money. Depending on the scope of your duties, the pay could actually reach triple digits, but I’m pretty sure that involves wiping someone’s butt, and I’m not talking about a baby. For us, we know these jobs are more about the lifestyle and flexibility. Our goal is always to make enough to pay our bills (obviously), but other perks—like when the job includes Internet and food—allow us to tuck away a few bucks here and there. We do occasionally make extra money (i.e., my freelance writing), but it's not even necessary. So, we may not make a lot of money, but we are also not spending any. While many ads target and expect retired folks because of the low pay, J & I continually surprise people when they find out we are in our 30s.

The interview isn’t only about them getting to know you, it’s about you getting to know them. We’ve interviewed for a few positions and turned them down. We’ve also interviewed for a few positions and should have turned them down. Go with your gut … my dad always says, “if it doesn’t feel right, it ain’t right.” Step up your communication and ask applicable questions, like how long was your previous person in place or how do they get along with the community, especially in the case of lodge management. More often than not, J & I are accepting jobs site unseen. Usually it’s just a matter of difficult logistics since we are all over the country, but it’s part of our chosen adventure. We do as much research as we can in advance, googling the name of the business/place, reading Trip Advisor reviews and asking to speak to former employees. Oddly enough, it is sometimes helpful to pay attention to the ads in Caretaker Gazette. Seeing an ad repeatedly could be a red flag for high turnover, for example.

We learned our lesson the hard way on this one. If anything, it will establish clear expectations on both sides. These are not jobs, but lifestyles. A lot of times, the duties are unsaid. But, they are better off in writing. You need to set your limits and parameters as much as the other parties.

J & I are passionate people who like to take ownership of the task at hand. But, everyone works for someone. And even when someone might want you to give the business a fresh look over, it’s important to remember that said business is that person’s baby. Don’t go reinventing the wheel. There are probably methods in place for a reason. Ease your way in, learn the business, learn the style of the owners and find a middle ground.

We almost solely rely on Caretaker Gazette because it’s so good. You have to subscribe and a huge newsletter worth of jobs (for both singles and couples) comes out every other month. But there are also occasional e-mails with last-minute and immediate job opportunities. I think the subscription is $29.95/year, and it is well worth every penny. Every job we’ve gotten has come from there and the newsletters are chock full of a wide gamut of opportunities. Sometimes the ads are downright entertaining, not to mention the variety of animals that make an appearance in petsitting/farmhand ads, everything from laying hens to bobcats. Here’s another piece of an ad that gave me a chuckle: “smokers, substance abuses, Mountain Dew addicts, people needing psychiatric medications and compulsively reckless people should not apply.” Well, okay then.