Travel While You Work: Here’s How

It’s hard not to feel a little envious of digital nomads, showing off their beautiful vistas and laptop-themed flat-lays on Instagram. But for those who work in jobs that don’t exactly scream ‘remote working opportunity’, i.e. most of us, the prospect of picking up your laptop and decamping to a foreign land can seem like a distant, tropical-flavoured dream. Even more so if you’re keen to stay in your job (it turns out millennials aren’t the disloyal job-hopping monsters we’ve been made out to be).

But recently, a growing number of providers – companies like We Roam, Remote Year and The Remote Experience – have started to bring that dream a little closer to reality. Offering a structured globetrotting itinerary and professional development opportunities, these travelling co-working spaces are opening up the digital nomad life to more traditional jobs.

The deal? You bring your job and they’ll sort out the rest – arranging travel, accommodation, workspaces and events as their mobile professional incubator moves to a different city each month. All at a not-insignificant price, however.

For some, this curated experience may do away with the joy (and sorrow) of remote working and it can certainly make sense to go it alone. But for others, the structure and professional development opportunities on offer can make these programs an easier sell to your existing employer.

Sean Harvey, co-founder of We Roam, stresses their focus on these aspects. “There’s no one here who is on vacation,” he says. We Roam filter their applicants through an online questionnaire and interview, looking for “professionally driven people, people that are here to advance their careers, to advance their personal lives culturally” says Sean. And they want to help you make the case to your boss, they’ll even video chat with the CEO to get you across the line.

Before you take the leap and hit the ‘apply’ button, here are a few tips on how to make to make this experience work for you and your employer.


Find the right fit

There are a growing number of companies creating digital nomad experiences, so it’s important to research the best option for you and consider the message it sends. Choosing a professional development-focused provider says one thing. Choosing a retreat for entrepreneurs says quite another.

Know what you’re in for

When thinking about how your job could operate remotely, it’s important to think realistically. These trips take you to amazing locations but it can also mean playing a torturous game of Twister with timezones. Can you work just as effectively while your boss and your clients are sleeping, or will you be bathed in the glow of your laptop at 2am every morning?


Put in the groundwork

Workplaces may be evolving, but asking your employer to let you loose on the world for three, six or even 12 months is still a big deal. So asking in your first week (or even your first year) in a role is probably not the best way to go. Establish yourself, show your employer they don’t want to lose you, then make your case.

Pitch it real good

When it comes to the big ask, be prepared. Many providers will help you with this, but it’s important to think it through: no one knows your job better than you. Sean’s tip for talking to your boss? “Give the right reasons for why you want to do this, not just ‘hey, I want to travel’. You really have to put your reasons for why this is beneficial to you personally, professionally and why this would benefit them.”

Be open to the experience

Your trip is approved and your bag is packed, so how do you make the most of your new nomadic life? “This sound so clichéd, but it really is true, the experience is completely what you make it” says Sean. “I don’t think there’s anything that anyone can do to prepare for a trip like this. There’s ups, there’s downs, you will cry, you will laugh, you will make friends that you will have for the rest of your life.”

Kate is a Melbourne-based writer with a mild podcast obsession. She’s awful at social media, so don’t go looking for her there.