For the past three years, she’s been travelling with her son, Will, who has just turned 11, and husband Brendon. Using Mexico as a home base, they’ve spent a few months at a time in Brazil, Indonesia, the United States, Singapore, Europe and Britain.
Being online during New Zealand business hours means Hughes starts work at 5.30am when she’s in Southeast Asia, then has the afternoon and evening free to go exploring. In Mexico, where they have temporary residency, she starts late and works into the night.
All she needs is a Wi-Fi connection – sometimes hotspotting off her phone – but juggling the time differences can be tricky. In Britain and Europe, that was particularly challenging.
“Daylight savings took my small time window to no window,” she says. “My boss told me not to do that again.”
Jen Hughes working at the beach in Cumbuco, a fishing village on the northeast coast of Brazil.
The weather in France was too cold, anyway, for a family who chase summer. Hughes, who speaks Spanish, spent time in Chile as a teenager. She loves the rich culture and unpredictable “craziness” of Mexico, where they have a car and keep some warmer clothes in storage.
The rest of the time, they travel on tourist visas with their lives packed into a handful of suitcases, including a large carry-on bag for Will’s Lego collection. In Brazil, they did a pottery class every week and filled an extra case with all the pieces they’d made.
Brendon, who was a lab technician in New Zealand, has picked up more of the parenting responsibility for Will and is developing a business online. In countries like Mexico, they can manage on a single income.
“I think we’re going to have kittens when we get back to New Zealand and feel the cost of living,” Hughes says.
“The hardest thing for me is when I see the boys going off to do fun things. It’s not like being permanently on holiday because I’m working fulltime.
“But it does feel like I’m on holiday, if I compare it to what everyday life was like in New Zealand. When I finish work, I don’t have jobs to do. Brendon takes care of that, and then we just get family time.”
Will makes friends with an iguana in Yelapa, a small beach town in Mexico.
Wrangling remote teams became part of the landscape for companies during the Covid pandemic. However, Hughes is in a unique position as someone who’s employed on staff in New Zealand while located permanently offshore with no fixed abode.
She’s encountered a few Kiwis on “sabbatical” with their families. However, most of the professionals she’s met who are long-term travellers either run their own business or are digital nomads doing gig work online.
Now in her mid-40s, Hughes joined Rothbury in a broker support role when she was 19 and the company had only eight people on its staff. There are now close to 500 nationwide – and the person who interviewed her for the job, managing director Roger Abel, is still her direct report today.
“It wouldn’t have been possible without him,” she says. “We’re very in sync in the way we work together.”
Over the years, she’s held various roles, from executive assistant for the managing director to IT, due diligence, financials and acquisitions. On her 25th anniversary, she was flown back from Mexico to attend the company’s conference in Australia.
“I’ve got all this knowledge in different areas of the business, so I’m quite useful,” Hughes, whose status as an overseas remote worker is flagged on her email signature, says.
“Even if I’m not around physically, they’d rather have me still working for them than not at all.”
The family in Mérida, the capital of the Mexican state of Yucatán, which has a rich Mayan heritage.
Stepping outside the 9-5 office grind is something Hughes has been working towards for a long time. In 2008, she moved on to a lifestyle block north of Auckland and went hybrid, commuting into the city two or three days a week.
When Will was born, she worked part-time from home and later moved to Nelson, which is where she met Brendon.
“Then Covid happened,” she says. “I was fully remote at that point, so I guess they were getting more and more used to me not coming into the office at all.
“We started looking [offshore] and narrowed it down to Spain and Mexico. I agreed with my boss that we’d try it out for a one-year trial to see how it goes.”
Jen and Will at Foz de Lumbier, a narrow gorge in Spain at the foothills of the Pyrenees.
Three years on, the pros have far outweighed the cons. The hardest aspect of long-term travel as a family is finding enough social time with children of a similar age, says Hughes. Teenagers can find that especially tough.
She thinks Will has thrived on his “real-world learning and experiences”, enrolling at local schools or joining homeschooling collectives in the community. A couple of years ago, he went to a “forest school” in Oaxaca, one of the most biodiverse states in Mexico.
Still, he’s now at a stage where he wants to put down some roots and have a more regular routine. That’s unlikely to involve a return to New Zealand, though.
“My big thing is just go and live,” says Hughes, “because you don’t know how long you’ve got, right? Life can be really cruel where people retire and they’re gone in a year.
“I don’t want to work my whole life for that. Go and live your best life and enjoy the hell out of it.”
While the circumstances that have allowed Hughes to do just that are rare, a growing number of New Zealand organisations are offering more flexible working conditions as part of their company ethos.
Last week, Amy McWhannell was in Buenos Aires visiting her grandmother, Marti, who is in her late 80s.
For a fortnight, their mornings were dedicated to spending time together. Then, while her grandmother was resting, McWhannell’s working day would begin.
Aucklander Amy McWhannell in Buenos Aires with her Argentinian grandmother, Marti.
In Argentina, it was 4pm when Wright Communications – the Auckland public relations agency where she’s on staff as an account director – opened for business at 8am. By the time she clocked off, after an eight-hour shift, it was 1am.
The time difference wasn’t too much of a problem, she says. “South Americans eat late, at around 10pm, which is lunchtime in New Zealand, and Buenos Aires doesn’t sleep.”
Growing up, McWhannell went on family trips to Argentina every year with her mother, who was born in Buenos Aires. Moving into the workforce made that much more difficult, with limited annual leave outside the end-of-year shutdown.
When she joined the PR agency almost five years ago, a flexible office policy, including “work from home Fridays”, was already in place. Then, two weeks into the job, New Zealand went into lockdown.
Moving home to her parents in Hamilton, McWhannell worked remotely until the borders reopened. In early 2024, she relocated to the Bay of Plenty permanently and has recently bought a house with her partner in Pāpāmoa.
Still on the payroll full-time, she commutes to Auckland once a week and spends every Wednesday dialling in remotely from Hamilton, where she teaches a “shapes and core” class at Les Mills gym before and after work.
“It’s all about trust,” she says. “I’m talking to clients every day. If you’re responsive and constantly in communication with your team, they can see you’re still getting the results.”
McWhannell, left, and her sister, Ashley, with cousin Vicente at a football game while the sisters were in Argentina visiting family.
McWhannell’s first long-distance stint, working from Argentina, was a three-week trip with her sister Ashley to spend precious time with their grandmother and wider family there last year.
With New Zealand haemorrhaging talent offshore, she believes companies need to offer more flexible working conditions if they want to stay competitive.
“There’s a stereotype with working remotely that almost makes you work harder, because you don’t want to fall into that trap,” she says. “Like, I’m actually so responsible. I’m always at my desk.”
In a survey of 200 senior managers late last year, 55% said a hybrid working model (a mix of in-office and remote) best described the way their company operated. However, that figure was down from 63% the previous year.
At Unilever, employers in New Zealand and Australia can request to work remotely from overseas or interstate for up to 20 days a year. Recent offshore locations have included India, Argentina and Indonesia.
Yet despite the globalisation of post-Covid workforces, there are some fish-hooks to avoid, as writer Lara Markstein discovered when she moved back home from the United States.
Lara Markstein spent five years working for the University of California from her home in the South Island before she was told to return to the US or forfeit her job. Photo / Anthony Phelps
The assistant director of the Centre for New Media at the University of California, Berkeley, she began working remotely before the pandemic hit, relocating to North Carolina when her American partner, Mike, took a job there.
In 2019, they decided to settle in New Zealand, where Markstein had spent her childhood after migrating with her family from South Africa when she was 7. The couple now live with their toddler in Waikawa, a small settlement near Picton.
Her immediate supervisors were happy for her to continue to work remotely from New Zealand, which she did for the next five years. During that time, she won a staff award and was approved for maternity leave.
Last July, she was sacked when a whistleblower discovered by chance that she was living permanently offshore and informed the “university bureaucracy”. Markstein was slapped with an immediate stop-work order and given two weeks to return to the US to keep her job.
By then, she’d been in the role for 16 years. However, her “at-will employment” conditions meant she had no contract and could be legally terminated without notice at any time, a common scenario among workers in the US.
“That’s not how things work here,” she says. “Essentially, as soon as legal found out, they really had to fire me, because otherwise they would have been subject to New Zealand employment law. So there were no hard feelings. I understood where they were coming from entirely.”
Markstein says the legal and tax implications of working offshore can be complex, and companies offering advisory services aren’t always fully transparent about the potential consequences of that.
Mike, who is an internet business lawyer, is also working remotely but in reverse, running his practice from Waikawa and working with clients in the US.
“If you’re an American citizen, you have to pay tax, no matter where you live in the world, and there’s a very complicated tax treaty with New Zealand that we have to deal with,” Markstein says.
Still, returning to the US wasn’t an option she considered, even at the cost of her job. “I was sad to leave my role, but where we live is a magical, beautiful place.”
Joanna Wane is a senior lifestyle writer with a special interest in social issues and the arts.