I Tried A 'Working Vacation' In Lisbon. Here's How It Went…

Photo: Jerry Hernandez/Outsite.
I’ll be honest, until this month I assumed 'digital nomad' wasn’t a thing real people said. It felt like a marketing term invented exclusively to irritate the over-40s. A vague, pretendy concept made up by influencers to disguise the fact their job is being paid to go on holiday and shill bikinis to teenagers.
'Working vacations', meanwhile, I believed were real, but I couldn’t understand why anyone would want one. My main measure of success for any holiday has always been how little mobile data I spunk on refreshing my emails, and how far from any kind of mental exertion I can possibly get while being alert enough to shovel calamari into my mouth. When friends talked about filing features or diffusing work disasters on their phone from a poolside sun lounger, I only felt sorry for them. A working holiday, surely, was just a bad holiday?
Then I had a go myself. And quickly realised the point of a remote working vacation isn’t about letting work encroach on your holiday time, but rather the opposite: plugging extra holiday experiences in around your deadlines, and feeling inspired by the change of surroundings.
As apparently the only person left on Instagram who hadn’t been to Lisbon, I’d been clamouring to visit the Portuguese capital for ages. But my boyfriend had already been twice and my friends were all booked up or skint from weddings – so when I was invited to stay at a new 'co-working and co-living space' in the city, it presented the perfect compromise. I would go on my own, and try remote working. I would explore the cobbled streets and prettily tiled tavernas with my laptop tucked under my arm, and write whenever the mood struck me. I would be filled with equal parts inspiration and custard tarts. And if I got no work done at all, well, that would only prove my cynicism right.
Outsite is one of a new breed of companies (see also: Remote Year; Terminal 3) hoping to revolutionise the way we work and travel. Offering hip accommodation for remote workers and company retreats, there are 11 Outsite locations in picturesque destinations across the US, Hawaii, Puerto Rico, Costa Rica and Bali, plus three new sites opening soon in Barcelona, the Swiss Alps and Mexico. All promise a quiet, productive environment but with community activities and a house WhatsApp group to foster fun, networking and those all-important creative vibes.
Photo: Jerry Hernandez/Outsite.
More like a luxe halls of residence than a traditional hotel, Outsite Lisbon is a gorgeous Portuguese townhouse with a vast co-working space on the ground floor and four residential floors above it. My room leads off a shared lounge area, with a shared kitchen down the hall. I have visions of being kept awake by banterous brainstorms into the early hours, but the atmosphere is completely serene. Beyond my balcony, life on the lively Rua de São Paulo clangs by, but inside it’s all calming white walls, lush pot plants and the distant tip-tap of other workers on their laptops. A perfect place to work. In theory.
In practice, it takes half my trip to stop feeling guilty when I’m not working and overwhelmed by FOMO when I am. As a freelancer I’m pretty well practised at the main elements of a solo holiday: eating alone, walking around alone, sitting in coffee shops for obnoxious lengths of time, alone – but being in a brand new city affords a million distractions. Everything I see takes on the lustre of the foreign and unknown. Look, a beautiful church! A funny pigeon! A branch of Zara in a rustic old bank! If I don’t Instagram those centuries-old tiles, did they even happen?
Once I relax into it, though, being away from home also makes it easier to block out the everydayness that normally stops me getting stuff done. No washing to hang out, no friends to see, no post office errands to run. You remember how much of the average working day is spent on stuff that isn’t working. Strip away all the extraneous chat and pointless meetings, and three hours of solid work could be enough for a whole day.
Of course, it helps that Lisbon is full of good outlets for digital nomadding. Places like Cafe Tati, a dreamily rustic but freelancer-friendly café tucked away behind the heaving Mercado da Ribeira. I’d like to pretend I stumbled across it rather than typing 'COOL COFFEE SHOPS WIFI LISBON' into Google with one hand while I went through passport control, but either way it was a win. Twinkly music, Wi-Fi as strong as the (80 cents!) espresso and just a smattering of sexy punters, alight with the glow of their Macbook Pros. I sit, I sip, I actually do some work. I wrote this whole paragraph, in fact.
Photo: Jerry Hernandez/Outsite.
There are downsides to all this #blessed remote working – neck strain from lugging a laptop around; having to tinker with your Google settings all the time because everything keeps coming up in Portuguese – but in always-on, digitally primed cities like this one, they’re decreasing every year. European breaks even have the advantage of no extra data roaming charges in EU member states (though who knows how much longer we’ll have that luxury).
I thought the weather would make it harder to work, but actually there’s something about the loose muscles and long evenings in a warm climate that makes it easier to feel creative and spontaneous. On my second night in Lisbon I take myself out in search of midnight snacks and end up in the Time Out market with my notebook and a huge slab of chocolate torte, working on both until 2am. The trick to productivity, for my lazy brain at least, has always been to bribe myself like a wayward toddler, and apparently holidays are no exception.
Of course, living the nomadic dream when you only have yourself to indulge is one thing; it’s a whole different deal when you have other people in tow. But still not impossible. Or so promises Jo Rourke, a content strategist and entrepreneur who just spent a month working remotely from a villa in Lanzarote, with her husband and, impressively, their three children aged five and under. "It certainly isn’t for everyone, but for those who can, a working holiday is an amazing way to see new places and experience different things," she tells me.
Jo’s best advice? Plan it carefully. "Running your own business gives you a lot of freedom, but it also means that if the wheels come off when you’re away, you better be able to fix them remotely," she says. Jo recommends trying an email automation service like Boomerang for Gmail – so your inbox can be firing off replies while you’re sinking Aperol Spritzes – and sorting out templates for your most common communications in advance, to save time. She even launched The Magic Words, a members' club for freelancer email templates, during her remote working break. Digital nomad advanced level: unlocked.
And me? After three days I’ve managed a decent amount of working, but not so much the elusive 'co-' element. So finding another Outsite guest, Omar, typing away at a communal table, I force myself to try a little 'creative collaboration'.
"What are you working on?" I ask, hopeful for screenplays, TED talks, concertos. He looks from me to his screen to me again, frowning, and eventually shrugs. "It’s too boring to explain."
I fare better in the kitchen with Joanna, a mermaid-haired vegan, who is living here for a month. She’s working on a series of 'animated spiritual meditation videos' with her mother, a psychic medium. Okay, sure. Joanna invites me to drinks organised by Lisbon Digital Nomads – with 3,385 members at last count, it’s the second biggest digital nomad group in the world, or so cofounder Rosanna Lopes proudly tells me. She organises weekly meet-ups to give remote workers and travelling freelancers the chance to exchange ideas and make connections, or perhaps just speak to a human in full sentences for the first time in several days. And there’s plenty of demand; currently rated third in the world by NomadList, Lisbon is fast becoming a co-working capital. Second Home opened a plant-filled office here last year, and the ludicrously hip LX Factory quarter is home to massive business and tech hub Coworklisboa.
Photo Courtesy of Second Home.
Second Home Lisboa.
But while the large, buzzy crowd of twenty- and thirtysomethings I find standing round drinking beer in a leafy square would suggest that digital nomads are far from imaginary, everyone is also keen to assure me they’re not really one. "I’m a fake digital nomad," at least five people tell me in conspiratorial whispers. Maybe nobody actually thinks they’re a digital nomad? Perhaps there is one man, somewhere, with a goatee and a Fjallraven Kanken backpack, who called himself a 'digital nomad' one time and it just stuck.
Still, the digital faux-mads are doing a pretty good impression. I meet Chris, a chiselled-jawed photographer from Toronto, who is also scoping out the co-working scene in Colombia and Thailand. I meet Jesse, from Michigan, here for a coding internship. She’s had an idea for a social media food app that I’m pretty sure could make her the Zuckerberg of brunch. I meet Brian, an eco-activist and inventor, and get embroiled in a debate about single-use plastic. For what was supposed to be a solitary holiday, it’s turned into one of the most sociable I’ve ever had.
Later, as I extract myself from a group who have stumbled back to Outsite clutching pint glasses of sangria and are off to continue the party on the fourth floor, I have a small epiphany: being a digital nomad might just be the acceptable face of youth hostelling for the hustle generation. It’s like a gap year, but with invoices. A way to see the world without putting your career on hold. And it might not be for everyone, but it’s certainly nice work if you can get it.

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