You CAN be a digital nomad, and an HR high flier: Here’s how

At the age of 24, Vanesa Cotlar was living in Toronto, working as a senior consultant at Deloitte and traveling frequently for business. She loved her job – particularly the travel aspect – but couldn’t shake the desire for more.

“It was this feeling of seeing people wait until they’re retired to experience the life they want, and I had this thought that there has to be something that enables me to have the life I want, at this age,” Cotlar told UNLEASH.

In 2018, Cotlar found what enabled her to do just that. From thousands of applicants to a programme called Remote Year, she secured one of 35 spots in one of the first 20 cohorts to spend a year traveling and working from 12 cities across four continents.

Not only did she fill her appetite for travel, but she secured some private consulting clients along the way, and even co-founded a HR tech start up with a fellow participant.

That set the direction for Cotlar’s working life today, resuming travel after the Covid pandemic. From mid-last year, she became a digital nomad again, planning locations to work from in three month chunks, while maintaining a base in Canada.

She became Head of People at digital insurance company PolicyMe, aligning with the founders on a shared vision of remote work giving employees greater flexibility, which has become an embedded part of company culture.

As part of PolicyMe’s leadership team, and now VP of People and Culture, Cotlar has since worked from France, the UK, Argentina, Peru, Colombia, Mexico and most recently, Latvia. She’ll be spending July to October working across Canada before traveling internationally again, this time to the Canary Islands, and again to Argentina, where she was born and grew up before moving to Canada at age nine.

The way Cotlar combines travel with a full-time role adds an extra dimension to the digital nomad narrative, which usually centers around solo workers – usually content creators, consultants and entrepreneurs.

Despite the growing calls back to the office from more companies, those who remain remote-friendly – even remote-first – are able to attract and retain talent like Cotlar, who are dedicated to their work but passionate about flexibility. ‘Remote HR jobs’ became one of the most popular Google searches this year, with data from remote marketing agency Enflow Digital revealing that HR was the sixth most searched for remote role in March this year, behind marketing and finance and ahead of IT and accounting – all functions in the top 10 searches for remote roles.

Overall, the search for ‘remote jobs’ grew by 58% when compared with the same period last year. 

Rule number one – work comes first

Yet company U-turns on remote work – most recently and notably Google and Meta – make Cotlar determined to continue her lifestyle in a way that prioritizes work. 

“My number one thing has always been, work comes first,” Cotlar emphasizes. “I used to have a fear of missing out – there’d be all these things going on, and I wanted to do them all. Then when I started traveling while working, I realized there will always be more things.

“Now, I just feel gratitude for the experience, because I have a job that gives me flexibility. That mindset – and creating structure and internal processes to make your life doable wherever you are – is what enables everything else for me – then you get to reap the rewards.”

Cotlar largely works PolicyMe’s Toronto hours regardless of where she is, to offer seamless collaboration and communication for her colleagues. She leans on Notion, Slack and Zoom to stay on top of tasks and priorities, which include regular updates with the leadership team and managing a team of two.

To avoid distraction, she’s devised a departure and arrival routine which involves flying on Saturdays, spending Sundays confirming her nearby co-working space, food store and gym, to be good to log into work on Monday. Tours, restaurants, bars, beaches and anything else that falls into the travel camp is saved for non-working hours.

Rule number two – you can’t do it all

This approach rings true for Jessie Danyi, previously head of people at business expenses platform Pleo, and now belonging and impact lead. Having joined Pleo in 2018, like Cotlar, she helped shape the company’s remote-first structure. She became a digital nomad in 2020, committed to living on one continent per year in search of a potential forever destination.

She’s worked from countries including Egypt, Senegal, Morocco, Mauritius, Kenya, Hungary, Croatia, Mexico, the US and Denmark, where Pleo is headquartered. She’s currently back in her native South Africa, before spending the summer in Greece. She uses a website called NomadList, which helps her track the amount of time she stays in each country and helps keep her on the right side of visa regulations.

Like Cotlar, Danyi has a departure and arrival formula, and thrives on a routine which includes daily exercise, typically surfing or yoga. Most important is that strong work ethic to ensure being a digital nomad never becomes a pain point for anyone else. 

“You need to understand you can’t do it all. So you need to be upfront with yourself on where you’re willing to compromise. Some digital nomads, like freelancers, are optimizing for travel, and their work is providing them the ability to do that. I optimize for work, and travel is a bonus,” says Danyi.

“My heart wants to go to Madagascar and be on an open beach by myself, but I’m not going to do that, because that’s going to be unreliable for work, and threatens my career. And I take a lot of pride in that.”

It’s not always been smooth sailing and Danyi has plenty of experiences she’s learnt from. She found trying to keep European hours from Mexico unsustainable. A co-working space she’d booked in Senegal didn’t seem to actually exist, meaning she worked largely from her apartment.

Danyi also began to find managing a team of 55 challenging, so was able to evolve her role into an ‘individual contributor’. It’s still a senior position, but one that’s more autonomous, working directly with key stakeholders, and more amenable to travel. 

Rule number three – over communicate with colleagues

Finding compromises between work and travel rings even truer when you have children, as recruiter, and father of two, Luke Haynie, has discovered. Growing up in a small town in Texas, he loved hearing about the adventures of his many aunts and uncles who had lived and traveled all over the country, and wanted to live those experiences himself.

With two young sons, though, living as a digital nomad isn’t always straightforward. But discovering and becoming investors in the program Boundless Life, which offers family workation packages including accommodation, co-working space, and schooling for under 12s, opened this door for Haynie and his family.

The Haynies trialed their digital nomad experience with a one month family ‘workation’ in Sintra, Portugal last year with Boundless Life, followed by two weeks in Spain independently. Like Cotlar and Danyi, Haynie shifted his working hours to align with colleagues in the US at staffing company Stone Resource Group, while also working on his own recruitment consultancy, Qualified and Co.

On workation, Haynie felt more focused and connected with his team, conducting video calls with all 50 of his reports over two weeks, using Microsoft Office tools to collaborate, and a Bullet Journal to stay productive. He made sure to communicate clearly with senior execs, adding extra documentation to his regular reports, ensuring nothing would get lost despite his virtual presence. 

“It’s like you’re living two lives, because you’re really having the time of your life, and then you’re also downplaying it to the people that you probably spend the majority of your waking hours with,” Haynie recalls. “I had to work a bit more, timewise, because I needed to over communicate.”

Satisfied that he, his family, and his business are all able to thrive while working from abroad, the Haynies are happy to commit to a yearly workation, continuing with Boundless Life for the schooling aspect. Next time, they can choose from destinations like Italy, Greece and Bali.

“I come from being a people leader in the staffing business where my whole career is moving people between jobs, so encouraging birds to leave the nest is my default mode, right. So my message to employees underneath me, is that you need to get out there and explore, and find something that’s going to make your life worth living.

“If I have a bunch of employees who are living a life worth living, then I know my team is going to exceed expectations,” says Haynie.

Above all – seize the opportunity

While Cotlar, Danyi and Haynie all have different motivations for wanting to combine work and travel, a deep appreciation of the privilege of being a digital nomad, while maintaining a full-time corporate role, is what unites them.

“I see this as a wonderful opportunity I’ve been given – so I take my responsibility in that seriously. I’ve put it on myself to be a good colleague, and to prove this type of lifestyle is sustainable. I’m very grateful.”