Long Reads

How to be freelance: this is the reality of living the ‘dream’ Instagram lifestyle

Looking for advice on how to be freelance? There are nearly 3 million #digitalnomad posts on Instagram, following the envy-inducing lives of remote workers across the globe. But it’s not all coconuts and sunsets, as seasoned freelancer Elly Earls knows all too well.

I know you’ve seen the pictures. The bikini-clad woman sat on the edge of an infinity pool with her laptop, effortlessly earning a six-figure income with a coconut held aloft in her hand. 

You’ve probably spent many a dreary commute fantasising about jacking it all in to join her before reluctantly admitting to yourself that the #digitalnomadlife we see on Instagram can’t possibly be reality.

You’d be correct. And yet recent research from social media management company Buffer found that 99% of remote workers would like to continue working remotely at least part of the time for the rest of their careers, while 95% would recommend it to others.

hotel pool
How to be freelance: fancy making this your office?

We don’t yet know how many remote workers are digital nomads – defined as those of us who can work from anywhere and have no fixed abode. But there are nearly 3 millions posts tagged with #digitalnomad on Instagram. And I can tell you from experience that there are many more of us now then there were when I quit my job as an editor in the UK to go freelance and start working remotely at the end of 2011. 

At the time, I was 25. My boyfriend had just read Tim Ferriss’s New York Times bestselling book, The Four-Hour Work Week, a guide to “escape the nine to five, live anywhere and join the new rich”, and he convinced me that I could work from anywhere in the world. I quickly devoured the book – in a completely non-clichéd fashion – on my bus commutes to and from my nine to five. 

Within months, we’d paid the final month’s rent on our three-bed house, sold everything we owned and booked our tickets to south-east Asia. 

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Feelings I remember from those first few months were an equal mixture of excitement (we were pioneers! Our friends and family might think we were crazy but it really felt like we were getting in on the ground floor of something special!), stress (internet speeds that would make the 20-somethings of today weep meant that Skype calls with important execs would drop out on a far too regular basis), and loneliness

While we may have been one of what felt like a handful of people blazing the digital nomad trail, that also meant there was hardly anyone around to talk to about what we were experiencing. In Bali, where we spent a lot of our time, there certainly wasn’t a coworking space in sight. 

Today, it’s a different world. Right now, I’m back in Bali for a few months and writing this article from one of dozens of coworking spaces that have popped up on this one tropical island alone. Other digital nomad hotspots such Chiang Mai, Medellin and Lisbon have seen similar growth. 

One report by MBO Partners says that nearly 5 million Americans now identify with the term digital nomad, while in the UK, the ONS reports that 2.6 million people work from different places with their home as a base. Coworking company WeWork currently has 848 locations in 123 cities worldwide, despite being founded just 10 years ago. And the trend is only going one way. 

work in sri lanka
How to be freelance: Elly working remotely from Sri Lanka in 2019.

Digital nomad life: the best bits

If it’s not all coconuts and infinity pools, why are so many of us leaving everything we know behind to hit the road, with no return ticket?

Freelance operations manager Becky Wong will celebrate her three-year digital nomad anniversary this spring, during which time she’s lived and worked in Thailand, Hong Kong, Italy and Bulgaria, among many other countries. She says the best bits about being a digital nomad are the freedom and the flexibility.

“It’s amazing to be in a country or city for a while and really absorb and embrace it, but at the same time have the freedom to up and leave at the drop of a hat and bring your laptop with you,” she tells me over Skype. It’s 7pm for me in Bali and noon in Sofia, Bulgaria, where she’s basing herself for the next month or so.

“Sometimes I still have to pinch myself and think: a month ago I was in Koh Phangan in Thailand, then Switzerland, then in the UK looking after two cats and now I’m in Bulgaria where I work during the week in different cafes or coworking spaces before going skiing at the weekend. My boyfriend and I often just say to each other, ‘what are we doing?!’” 

Like me, Wong works for herself, but these days that’s not the only option for digital nomads. When I was in New Zealand to attend 7in7, a digital nomad conference, in October last year – a pinch myself moment if I ever had one – I met Ali Greene, who is director of people operations at search engine DuckDuckGo.

The company is fully remote so there’s no central office. Employees work however suits them, whether that’s at home, in a coworking space or, in Greene’s case, from whichever country she happens to be in at the time. She’s both a full-time employee and a digital nomad, and she had come to New Zealand following a few weeks in Brussels with her boyfriend. Her next stop is coliving space Sun and Co in Spain and I’ll probably catch up with her again in Capetown in October.

how-to-be-a-freelancer
How to be freelance: "I’m not in that bubble of waking up, going to the office, doing my work, coming home, and watching the same news channel."

“The biggest benefit of remote work is that I’m constantly meeting people that inspire me and make me question my own assumptions of the world,” she tells me as we sip coffees on the Wellington waterfront. 

“I feel like my life is becoming more enriched because I’m learning so much from the world. I’m not in that bubble of waking up, going to the office, doing my work, coming home, and watching the same news channel. I’m constantly having to re-evaluate my own values, ideas and opinions on things and some of that goes back into my work, and some of it makes me a happier person.” 

Digital nomad: the double-edged sword of flexibility

I’d love to tell you that the best bits of digital nomad life are just that – the best bits. But the flexibility that comes with being able to switch locations at a moment’s notice can also be a double-edged sword.

Sonia Jaeger is a psychotherapist and digital nomad who works with clients from all over the world – many of them digital nomads themselves – over Skype. “Many digital nomads struggle due to the constant disruptions of their routines, physical wellbeing and social contacts. Keeping up routines and healthy habits when constantly moving around can be really challenging,” she says.

“Travel fatigue, anxiety and depression, as well as stress-related symptoms, are very common among digital nomads. Sometimes, these existed before they started their nomad journey (trying to get away from something and then realising you can’t run away from yourself) but more often these are results of the lifestyle. Especially for digital nomads who start from scratch. If you’re starting a new lifestyle and a new business at the same time, it can be very hard.” 

Koh Phangan April 2019
How to be freelance: Elly takes in the sunset in Koh Phangan in Thailand, April 2019.

These challenges can be exacerbated, according to Jenny Lachs, who runs online digital nomad community Digital Nomad Girls, if people start out on their journey thinking that being a digital nomad is going to be like backpacking or being on holiday. “You can’t be constantly exploring because you have to work,” she says. “Normal life comes with you; you don’t escape it when you become a digital nomad. You still have to look after yourself and make sure you eat well and exercise. Not every day is a special travel day.”

In fact, far from it. While Wong tries to schedule what she calls her ‘transit days’ on weekends, it doesn’t always work out that way and on more than one occasion she’s found herself firing out emails from the floor of an airport as it’s the only place she can plug in her laptop.

I can relate. I may have had my fair share of infinity pool moments, but I’ve also written an article at 6am on a budget flight from Thailand to Laos, grabbed a few hours of shut-eye on the floor of Kuala Lumpur airport, and found myself stranded in a remote Sri Lankan village with a Skype call scheduled in less than an hour. 

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How to be freelance: on more than one occasion, Becky Wong has found herself firing out emails from the floor of an airport as it’s the only place she can plug in her laptop.

Digital nomad: there is no going back

Yet it’s not the practical difficulties of the lifestyle that digital nomads tend to struggle with the most. The one thing everybody I speak to wishes they’d known earlier on in their journey is that there were other people like them out there. The freedom to move to a new and often exotic location every few months, weeks, or even days is an incredible privilege. But it’s also exhausting to turn up to yet another new place where you don’t know a single person and create a social life from scratch.

This is exactly why Lachs set up Digital Nomad Girls in 2015. It’s since grown to over 20,000 members and offers the structure, accountability and community that can be hard to create for yourself on the road. American Kit Whelan, who’s been a digital nomad for more than a decade, created the 7in7 digital nomad conference for similar reasons. And I’m not exaggerating when I say communities like this are probably the reason thousands of us can thrive as digital nomads.  

solo travel
How to be freelance: half of Brits are said to be working remotely by 2020.

“Without community, [the digital nomad movement] falls apart,” says Whelan. But with it, digital nomads have a safe space to discuss the challenges of the lifestyle, cheer each other on and work together on a sustainable way forward.

With half of Brits said to be working remotely by this year, according to the ONS, there’s no question that these discussions are going to become more important in the months and years to come. In fact, while many digital nomads I’ve met over the years do have plans to hang up their Osprey backpacks at some point and build a ‘home base’ to spend part of the year in, not one of them plans to return to the grind of the nine to five.

As Lachs says: “In the system we have in the world right now and the way the job market works, people are burnt out and terrified of losing their jobs. There’s so much pressure. This isn’t a complete break with the system but it offers a bit of an alternative and gives us a bit more control. I can’t imagine ever going back. Once you start living this way, everything changes.”

As for me, I don’t regret any of my journey – it’s given me strength, resilience and confidence I never knew I had. However, there are a few things I wish I’d known earlier on. My advice for anyone wanting to give the lifestyle a go would be to join the digital nomad communities and try not to travel too fast and burn out before you even get started – although this does tend to be a lesson you have to learn the hard way. 

But most importantly, remember that the beauty of this lifestyle is that you can live it however you choose. Think about why you’re doing this, what you want your life to look like and how the skills and experience you already have can help you achieve that. Happy travels. 

This piece was originally published on 27 January 2020

Images: Getty, Unsplash, courtesy of author