Frances Cook: How to make your house-sitting, digital nomad dream a reality

Travelling to exotic places and living rent-free while still earning a crust in your chosen field sounds fantastic – but there are a few things you need to know first. Finance writer Frances Cook talks to marketing expert and digital nomad Sarah Kelsey about how she made the dream a reality.

Travelling the world, getting free accommodation in return for alpaca cuddles, and building your dream marketing career while working remotely, might sound glamorous, but it nearly didn’t work out for Sarah Kelsey.

In fact, it took two attempts at the digital nomad life for the 25-year-old to make it work.

Two years ago she decided to pack up her laptop and work from Bali. The plan was to mix business and pleasure, traveling to nearby countries when possible.

But when Kelsey started what was supposed to be the adventure of a lifetime, she found herself unexpectedly hit by culture shock and loneliness.

“I hadn’t done much travel by myself, I’d done no travel by myself, really,” she said. "I just decided, yep I’m quitting my job, I’m moving to Bali, I know that that’s the place I want to be, cool, bought the flight, gone.

“I wasn’t really nervous, fearful, apprehensive at all, not even on the flight there."

But that soon changed. “It was the moment I stepped foot in a place that was completely different to anywhere I’d ever been before... that I thought, ‘oh my God, what have I done?’”

Kelsey warns that while the pictures of working from the beach can look glamorous, constantly moving and travelling can be unsettling.

There can also be an unexpected conflict between the travel and the work, with a struggle to make time for both and feel as though you’re "making the most" of the opportunity.

An uncertain living situation, less stable work contracts, and being in a new country away from friends and family, created a level of stress Kelsey says digital nomads don’t always talk about openly.

“I instantly felt a lot of feelings of isolation and loneliness, because I was by myself. I couldn’t really share those feelings with anyone," says Kelsey. "But then at the same time, I felt a huge sense of guilt to be feeling any other way than extremely positive, because I had this opportunity that not many other people get. So it was a very intense emotional journey for me to move through, travelling solo and navigating how I felt.”

After a few months, Kelsey decided to come back to New Zealand for a reset.

Rather than giving up on the dream of working remotely while seeing the world, Sarah Kelsey decided to give it a more informed shot, using what she’d learned from the first attempt.

This time, she made a plan for how she would balance work and travel, while also managing loneliness.

She’s combined deliberately hunting out meaningful work, with budget hacks like house-sitting.

Kelsey tested out house-sitting within New Zealand first, building up experience while also saving money for her next attempt at the digital nomad life.

She teamed up with a friend to house-sit as a duo, partly to beat back the loneliness, and partly to offer a wider range of skills for potential house sits.

“The first one we applied for was in a very, very, very small town near Taupo.

“It was a small petting zoo, with alpacas, chickens, two dogs, six cats, I’m not even kidding you,” she laughs.

“Alpacas are great, they’re so chill. They’re quite curious, they’ll come up to you and sniff around. Quite reserved, but also quite chill creatures, super easy to look after as well.”

The house-sitting world can be competitive, so Kelsey put her marketing skills to use to craft the perfect profile to land accommodation.

If you don’t yet have house sitting references, she recommends having multiple personal references instead, to show that you can be trusted with people's homes and pets.

The fact that the duo would be working remotely was another plus that they put high in the profile, to show potential house sits that they would be home often, giving the pets more company.

The plan worked, and after building up experience and reviews on a house-sitting network, Kelsey felt ready to jump into international house-sitting.

Then it was time to organise the work side of things.

Instead of "diving in head first" again, Kelsey made a plan for how she would balance the work and travel.

She recommends other hopeful digital nomads plan how long they’ll be in each destination, so that they have time to settle, and feel more grounded.

This time around, she’s decided to make remote work her priority, with travel slotted in around that – rather than the other way around.

“This time I’m more at peace with being here, why I’m here, how things work," she says. "Just like anything, the more times you do it, the more comfortable you become.”

Work is a mixture of her OneUp Project – a podcast focusing on money, career and lifestyle – and freelance marketing.

Even though she’s travelling, Kelsey’s decided to carefully choose the marketing projects she takes on, aiming to work for companies that she feels are making an impact on the world.

It may sound idealistic, but she says it’s possible to keep the meaningful work flowing, if you’re willing to be loud about your goals.

Kelsey uses LinkedIn to let people know about the work she’s looking for, as well as good old-fashioned word of mouth, telling people she’s worked for previously that she’s looking for a new project. “It’s a lot of luck, but also a lot of openness about what I want to do,” Kelsey says.

“It’s initially just being honest about what it is you want and what you’re looking for, and loud.

“It’s, ‘I’m looking for remote work, I want my life to look like this, who can provide me the opportunity to do that?’ Putting that out to your own network, or LinkedIn, or whatever it is. Being loud and proud about what it is you actually want.

“I think that clarity can be very endearing for a lot of people, because they think ‘well this person knows what they want, how can I help them get there?’

“It can be inspiring for a lot of people to hear that clarity of direction.”

You can listen to Frances Cook's full interview with Sarah Kelsey on Cook's new podcast Making Cents.

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