Head in the Clouds | Why the Digital Nomad Dream is a Lie

Remote working is on the rise among millennials. But is it what it's cracked up to be?

by Tabi Jackson Gee; illustrated by Bode Burnout
Sep 24 2018, 9:14pm

Ditching the nine to five, working remotely – and travelling the world at the same time? Sounds liberating. Revolutionary, even. Or does it? Tabi Jackson Gee imagines the ups and downs of the life of a wandering digital nomad.

Daisy felt alive as she walked through departures at Terminal Five. She was excited. Elated.

But also extremely, heart-stoppingly anxious. Neither Calm, Headspace, or being ‘Happy Not Perfect’ could help her now. She tried to pull herself together as she walked up to the check-in queue. I’m young, cool and people want to be me, she reminded herself.

A bit of nerves and the odd panic attack were perfectly normal. What was that Dolly Parton quote she shared on Stories the other day? “If you want the rainbow, you have to put up with the rain. #Preach” Yeah. It’s all going to be fine. Absolutely fine. Better than fine! She was going to LA to work as a part time freelancer at an insanely cool fashion start up. She was actually living her best life.

“What did she have to worry about? She was fucking winning at life. She was pursuing the digital nomad dream”

As she queued for security, Daisy took a selfie, made a few quick edits and posted: “Over and out LDN – coming to get yaaaa LA” to Facebook. 250 Likes at least for that, she thought, flicking through Instagram and eyeing up the suited guy in front of her. She was always getting teased for posting so much on social media but she didn’t let it get to her. She flicked her hair behind her shoulders with a well-practiced je ne sais quois and reminded herself; everyone else is just jealous.


They were the ones who had to sit in the same boring office every day. What would they even have to post about? Looking at the same view, listening to the same inane drivel. She, on the other hand, was an adventurer, she was one of life’s winners. Yeah.

Or maybe she wasn’t. Fuck. The nerves set in again. But then, she thought, anxiety is so in at the moment. I should capitalise on this too. She made a mental note to write a long-winded emotional post about it at the weekend. Maybe with a no makeup selfie for added impact.

She did some fire-breathing as she put her bags through the scanner, and reminded herself for the fiftieth time that morning that she was a total baller with a great job, an Instagram-perfect life and so much ahead of her. Warehouse party invitations. Long weekends in Mexico. Burning Man. Wait, maybe not that last one actually, it’s a bit passé. She made another mental note: must find out what the new Burning Man is.

“She made a mental note: must find out what the new Burning Man is”

In short, the anxiety could do one. She needed to focus on the important things. She was a thriving millennial specimen. She had freed herself from the tethers of the nine to five. No more commuting, get in! What did she have to worry about? She was fucking winning at life. She was pursuing the digital nomad dream. And she was goddamn FREE.

Free from the morning rush hour. Free from post-weekend small talk. Free from listening to the same music in a dull, overly-lit office where no one could ever agree on what temperature the air-con should be. Free from pretending to like people. Free from pointless meetings. Master of her own frickin’ destiny.

But also, she suddenly realised, free from the chance to make actual friends with people at work. Free from exchanging gossipy emails and knowing looks with her office wifey. Free from working with a team of people who cared about each other. Free from any kind of job security. Free from anything comforting, really. The kind of thing that helps most people sleep at night. Fuck.

She snapped open her laptop as soon as she found somewhere to sit. A message from her mum “Good luck Daisy darling, don’t forget to call me when you land!” and ten Skype notifications. Her new boss asking why she hadn’t replied to an email he’d sent five minutes earlier. Jesus, this guy was hard work. She was only supposed to be working two hours a day for him. He was only paying her for that. She really needed to figure out how best to manage him. That chest-clutching, lung-tightening claustrophobia came over her again. Eugh.

“She was free from any kind of job security. The kind of thing that helps most people sleep at night. F*ck”

She found a quiet corner of the lounge and tried to remember what her life coach had said about being present. Hmm. Deep breathing. Focus on your diaphragm. Watch your thoughts pass… Bullshit. She reached into her handbag for a Xanax. Whoever came up with this mindfulness shit had never had a panic attack in the middle of Terminal Five.


The day before wasn’t much better. The co-working space she’d been in was bustling with activity – mainly people strolling around and pretending they were working when actually they were on Instagram. Way more than she was. She’d spent six hours worrying about where to charge her phones if they ran out and trying to figure out if the hot guy in the corner was eyeing up her, or the irritating girl next to her. It was so distracting.

She hoped the co-working spaces in LA were better. The whole remote working thing had sounded fun at the beginning. In reality, it just meant sitting in a slightly comfier chair (which had definitely contributed to her getting Repetitive Strain Injury) while everyone around pretended they were, like, super important and were going to be the next Natalie Massenet.

The only time anyone spoke was if they making loud, self-important phone calls. “Oh hi Marcus, mate, yeah just give me two secs mate I’m just filing something to our massive new client, it’s like super hush hush, I’ll tell about it later, can I call you back? Thanks mate, that’s great, yeah, bye.” Her overly-subscribed London members’ club wasn’t much better. Eighteen silent freelancers to every big table, sat silently bashing away on their keyboards. Even the waiters were unfriendly.

“Whoever came up with this mindfulness shit had never had a panic attack in the middle of Terminal Five”

Ping ping. A string of Skype notifications from her boss brought her back into the room. God she hoped he wasn’t yet another arsehole. Why the constant micro-managing? Is that an American thing? Or is he just super intense? Screw positive thinking she thought with a returning sense of self-sabotage, and started to slowly list the amount of people she’d come across in the last two years who she had seriously fucking disliked.

It was always the clients that sounded cool initially that ended up screwing her over. The festival startup who didn’t pay for ten months. The fintech guys who had promised shares in exchange for work, then ghosted her. And not forgetting the misogynistic megalomaniac who she nearly had to take to court. Yay. Freelancing.


She sank further into the hole. What happens if it all goes tits up in LA too? Shut up, she told herself. You just need to get there and spend a bit of time in the sunshine. This job’s great, who cares if you don’t love the people you’re working with. You’re bloody lucky to have this kind of opportunity. And anyway, you can always moonlight as an Uber driver if you need more money. Like, loads of people do it. It would be fine.

Twenty minutes later she’d answered all her emails and her boss had gone quiet. She headed towards duty free to pick up some new perfume she couldn’t afford – that’s what credit cards are for, amiright?! Before she knew it she was sitting on her flight, ordering two Merlots – sod looking normal, she needed something to relax – and scrolling through the movie options. She glanced down at her phone to check it one more time before take off: 15 missed calls from her boss. Holy shit. Her chest seized up. What now.

She inhaled half of her first wine and opened the team WhatsApp group (so much for work-life separation) to see what was going on. And there it was: a screenshot of the company’s Facebook page, featuring a picture of her waving like an idiot and the words “Over and out LDN – coming to get yaaaa LA.”

It was going to be a long flight.

Tabi Jackson Gee is a freelance writer based in London, with first-hand experience of working remotely. Her first book What Would de Beauvoir Do? is out now on Octopus Books.

Bode Burnout is a London-based illustrator. You can follow Bode on Instagram and order prints, tees and other merch at bodeburnout.com